Sissy's Decline into a Slut

Chapter One: Sissy Crossdressing Play Time.

I'm sitting inside my car, it's late, a faint drizzle falls as the sound of the rain has me fade into a bit of a dream state... My mind is on the type of faggot, sissy slut I truly desire to be. I am in a lucid state of hunger for sissy humiliation and slut duty. It's almost d**g like... But a few hours ago I was merely preparing for where I am at this moment...

Earlier tonight my pathetically horny life of crossdressing as either a faggot sissy slut or a prissy sissy maid saw me dressed with full makeup, wig, under garments, black sheer pantyhose and one of my black satin maids dresses with white lace trim a white satin apron, black satin choker and a maids cap on my head. I stepped into a pair of simple, black smooth leather 5 inch spike heel pumps.

I was prancing around my home, feeling all sissy maid girly, playing with myself, wanting to pull my sissy dick until I cream all over my panty but trying not to. It felt so pathetic but exciting as I walked around in my heels, did a few chores. It's like so many hundreds of times in my past exciting like this. I soon sat and looked at online sissy porn and only wish it was me doing that.

My sissy mind wanted to push my limits but for years and years I was too sheepish and never really did. Tonight was different, I finally decided to push through and soon I grabbed my purse and my car keys. It was late oh a little after 11:00pm and I scanned around as I looked outside my front door. My nerves were all wild, my senses were heightened and I said, "Fuck it, get in your car sissy girl." as I scampered my heels were going click, clock, click, clock as I walked to my car, unlocked it and got inside. My heart was pounding and I was panting a bit. I settled down and soon I'm was driving out of my driveway and on the street, fully clothed as a sissy maid. I felt exhilarated as I drove around. I did not see many other cars on the road, mostly a few taxi cabs.

I drove around the town and soon my mind had me thinking about a 'rest area' about 15 minutes outside the town on a local highway. I decided to drive out to see it and whether it had people there or not at this time of night. My excitement was high as I wanted to see if maybe I could mince around the 'rest area' dressed as sissy maid Chantel.

As I arrived and pulled into the rest area off the highway I soon saw it looked empty of cars. I pulled into a parking spot just off the pathway to the large bathrooms. I sat in my car and soaked up all I have done...

Back now to the current moment in time. Yes, it's lightly raining and I am sitting inside my car, all dark and quiet short of the sound of rain falling on my car's roof with light music playing in background on my car stereo. My right hand does begin to fondle my sissy dick while it still rests inside my black satin, padded panty. Pre cum does wet the front area of the panty's crotch. I sniff my fingers and smell the smell of a male getting sexually aroused.

I'm thinking, 'It's so odd at how each step of my journey tonight soon pushes me to another. I mean hours ago, dressing up inside my house was exciting enough, followed by watching sissy porn on my computer. That only set me up to want to get out of my house and get in my car, which I did. Then I started up my car and began to drive around my town dressed as a sissy maid. This all brought me to this 'rest area'. I'm now feeling the urge even with light rain to step out of my car and walk around, maybe even inside the men's bathroom.'

This thought of pushing myself to areas I have yet to do in all my 40 odd years of living is compelling. The fear of being seen and maybe caught by others scares me but also turns me on.

I have been parked here now for about 15 minutes, playing with my sissy dick but not cumming yet is so exciting to me. I think, 'Do I do it? Or Do I not?' I so want to step out from my car. Soon another 10 minutes pass, it's 11:30pm on my car stereo's clock. I've been here near a half hour and no other car has come by. My courage is building. I decide to pop open my driver side door. The rain has now let up and I sit in the driver's seat just letting the cool damp air swirl inside my car. I feel the sensual coolness of this breeze on my black sheer pantyhose clad legs. It feels so fucking great to me. My head is a buzz with nervous excitement. Before I know it, my feet have swung daintily out and my heels plant on the pavement. I stand up and my dress falls nicely in place. I feel the cool breeze on my made up face, the breeze then blows my auburn and blonde hi-lighted, shoulder length with loose wispy curls wig lightly in my face.

I'm standing by my car and it feels so fucking exciting. Before I know it I have the driver side door closed, keys in hand of course and I make my first steps in my high heels. My senses are high and I feel as if each and every click, clock, of my spike heels reverberate all over the city. But step by step I walk further and further away from my car. I feel so excited and so sissyish. My courage slowly builds but I am scanning around myself, eyes darting left and then right and back to left etc.

I rather enjoy this late evening walk around this dimly lit and dead quiet 'rest area'. The continued breeze on my legs and my face feels so comforting. My breathing now normalizes. Soon I'm walking a good 50-60-70 feet away from my car. I see a covered picnic bench another 10-15 feet away. As I step on the wet grass my heels dig in and almost pull my shoes off my pantyhose clad feet. I then carefully walk to the bench and sit on it, looking back to my now car easily 75-80 feet away in the dim light of the rest area's lamps.

I'm thinking, 'If another car was to come now, I could never rush back fast enough in my heels to reach my parked car. I'd have to crouch and hide, hoping whoever it was would only come to use the bathroom and then leave.' This thought and fear only turns me on so much more. I have my right hand down my panty and play more with my stiff sissy dick. A part of me wants to now quickly jerk off and then go home, but another part of me wants to delay this eventual gratification.

It's now about 11:45pm. I've been here for about 45 minutes. My arousal is very high. I decide to walk to the bathroom. Each step of my spike heels gets me closer and closer. The outside door lighting will clearly show the sissy maid I am to any person who could be near by and see. But I am still alone. I am at the men's side outside door and figure if I step inside this brightly lit bathroom I will not be able to see any car that may come. This scares me but fucking turns me on even more.

Before I know it I'm inside, the door closes behind me. Alone my heels with each step, click and echo on the concrete floor. I love the sound. As I walk in the bathroom I soon see the large mirror on the wall above the counter and five sinks. I see my sissy maid reflection in the mirror and smile. I stand back and practice curtsies over and over and over, saying, "Hello Master, sissy Chantel at your service."

I'm so fucking horny right now. I prance around in my heels. I soon stand by the five urinals thinking if I could only hold a man's cock as he pisses in the urinal to then suck him off afterwards. I have no idea if a car has come or not. Some guy or guys could walk in on sissy me, but my arousal is so high it's as if I'm on a d**g. I now stare into toilet stalls and think, 'Fuck I wish I was being fucked up my sissy ass in one of these toilet stalls, or sucking cock in one.'

It's now after midnight and I can't contain myself anymore. I walk into one of the five toilet stalls, pull down my pantyhose and my panty. I begin stroking my white six inch, normal girth, uncut sissy dick. At this point it does not take long for me to shoot out a good load of my sissy cum. Drip, dribble it all falls into the toilet bowl. It felt fucking incredible. One of the most aroused masturbation sessions of my life. My head is near delirious as my sissy dick shoots out its load of cum. I excitedly stare at the sissy cum floating in the toilet bowl.

But alas as with most male ejaculation, once you blow your wad, the come back down to reality is often hard and fast. Dressed up as a sissy maid exacerbates this. I am soon just sitting on the toilet. The male err, well wannabe man in me has me feeling like shit. I say to myself, "What the fuck is wrong with me?" "Fucking pathetic, you fucking pathetic faggot sissy." "God dammit what a joke of a man you are." "Fucking look at yourself, maids dress, pantyhose, high heels a wig and makeup."

I sit on the toilet and just sigh. Soon I tuck my sissy dick back in my panty, pull my pantyhose back up, fix my dress and step out of the toilet stall. I walk to the door, peek outside to see if another car has come or not. Thankfully for me, I'm still alone. I quickly scamper in my heels back to my car and am inside on the driver's side. I rest for a minute and start up my engine. As I back out from the parking spot I notice headlights and yes another car is entering the 'rest area'. I am safe as I am now driving away but I think, 'Holy Shit, if I spent two more minutes in the men's bathroom I may have been seen and caught. Fuck imagine what may have come of that?

I laugh out loud about this now and think, 'Huh, maybe I'd be sucking cock right now, or being fucked up my sissy ass if I were still there. But maybe too some guy or guys could be beating the shit out of me.' That last thought scares me but the first two are turning me back on. But it's like 12:15am and I decide to drive back home.

I'm home by 12:30am and quickly scamper in my heels back inside my house. Tonight was some of the most exciting stuff I have ever done crossdressed and as a sissy maid. I sit down and relive the night in my mind and soon am playing with my sissy dick again. But I am imagining being caught by some guy or guys from that car that came as I was a leaving. My mind was thinking, 'Fuck that could have been exciting and life changing. I mean what if it was a guy or guys who'd have gotten off on seeing a faggot sissy girl like me. Imagine if I would have for the first time in my sissy life sucked cock or was fucked up my sissy ass by hard cock. DAMMIT! DAMMIT! DAMMIT! I wish I was caught now.'

Yes, I'm horny again and feel the arousal of what could have been. My right hand is stroking my hard sissy dick inside my panty and soon I shoot my night capper wad of sissy cum all over my satiny panty. Another little treat for myself. I am back melted down to feeling blah again.

I get up and go to my bedroom remove my sissy clothes and go to the bathroom and wash the makeup off my face. It's now 1:00am. and I am in bed. My mind wanders I know this, I'm going to do that again, I just know it. Sooner than later I'm going to dress up as a sissy maid or as a sissy slut and late in the night go back out to that 'rest area.' I smile as I drift to sleep wearing a white full slip over a white bra and panty and a pair of white tights that I sleep in.

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Chapter Two: It is Off to Another Play Night at The Rest Area and More.

Well a few days have passed since my first outdoor foray dressed as sissy Chantel, mincing and prancing around the local area rest area. I've been recollecting about that night every day since then. The thrill of it all is very powerful and I know that I'm going to do such stuff again. As I sit with a cup of coffee after dinner I begin getting hot for dressing up again and venturing out to that rest area again. I thought tonight I'm, going to dress up more as a sissy slut.

I took a nice hot shower and once dry I put lotion all over my body. A very close shave and then it's on to my make up. I have become a crossdresser who has been able to do very good makeup applications. I'm lucky being at 5'11" and about 185lbs. I look tall and slim. My face does feminize nicely. I really am a hot looking crossdresser/sissy.

As to clothes I put on a black satin bra and then slip in my breast forms, a matching black satin padded panty gets me going well. Tonight I'm going to pull on a pair of black silky sheer pantyhose and a black denim mini-skirt. A white satin long sleeve blouse finishes off my slutty outfit.

I relax dressed as such until about 10:45pm. Once it is 10:45pm I put on a cropped black, faux leather jacket, put my belongings into a black purse and I slip on my black velvet 5 inch spike heel pumps with cute ankle straps.

My nerves are heightened as I know I plan to venture out and to the rest area again. So as I click clock in my heels to my front door and first sheepishly peek outside to see if any people are around to see femmy me strut to my car. I am satisfied I shall be not seen. I scamper in my heels and soon sit in the driver's seat of my car. Start up the engine, rest and ponder things for a minute, 'Do I want to do this again? What if I get seen, get harassed or worse beat up? But I will have electrifying fun too. Driving to that rest area again will be so intoxicatingly fun.'

Soon I find myself out and about driving in my car. My mind melts into my feminine style and sexy feeling. Being a manual transmission car my mind wanders to my sexy fun high heeled feet manipulating the peddles as I change gears, brake, apply gas and change more gears.

It's cloudy but cool tonight so the rest area short of its few parking lot lamps and security lights outside the bathroom building will be privately dark for me when outside. If or when I walk inside the men's bathroom though it will be brightly lit. I keep on driving towards the rest area.

As I pull into the parking lot off the roadway I soon see two cars parked. My nerves really go wild. I at first park in a space further away from the two cars which are parked near the walkway to the bathroom. I'm scared but excited, I sit in my car and wait for a minute to see if people are coming or going to or from each car. It's too dark for me to see if any person sits inside either car. As I wait I can't help but find my right hand feel my crotch and my hard sissy dick. I feel the silky texture of the black pantyhose and it turns me on. I keep my eyes on the bathroom area.

A couple of minutes pass and I soon see one guy walk out and back down the walkway. I'm sure he does not see or notice me. He is focused on his car and soon he gets inside it and then drives off.

The other car is still parked, again it's too dark for me to see if it's empty or not. A part of me wants to step outside my car and tempt fate if a person or persons are in the bathroom. I think, 'If a guy or guys are still inside the bathroom, I could get out of my car and in the dark quickly scamper towards the bathroom, but off the walkway, staying on the grassy area of the rest area and hide from sight near the bathroom to be turned on by fear of being seen as I wait in hiding to see a guy or guys walk out and back to the car to then leave. I would need to be quick and discrete.'

I am close to popping open my door to do this when I see not the men's bathroom door open but the ladies. I see two ladies walk together down the walk way to the car. I so want to show them femmy me but I just meekly sit in my car. One gal gets in the left back door and the other gal gets in the right front side. I think, 'Shit it's a good thing I did not get out of my car as there was one person in the driver's side of the car.' Soon it too drives off, I am alone at a fun play place for a wannabe sissy slut tonight.

My car clock now shows 11:30pm. I now work the courage to step outside my car. Door open, high heeled feet planted on the pavement and standing feeling so horny and yes sexy, slutty. I close my car door and again I begin to walk. Again like my first time my high heels click clock seemingly so loud in the now still night air. I feel my heart pounding as I make my steps in my heels. The adrenaline rushes through my girly looking body.

The bathroom is about 60-70 feet away and I soon decide to move onto the grassy area and walk not to the bathroom entrance but to the back side of the building away from direct street lights. I lean against the back side wall and gaze at the entrance of the rest area. Soon I reach into my purse and grab my cell phone and set it up in video mode. I turn on the LED video light and start a video of me. I am so excited at this and make sure my selfie video shows my made up face, wig and clothes including my spike heels.

I narrate to my video, " Hi all who may see this video, this is sissy Chantel, out at the rest area off 'Apple Grove Road'. I'm here dressed as a sissy slut, enjoying being in a public place. I'm so nervous but so excited and horny."

I can't help but to touch my crotch. I now add to my video, "Two cars with people were here using the bathroom mere minutes ago. I hid in my car until they left, even though the sissy faggot in me so wanted to show myself to them. So I'm going to stand here in the dark for a bit but then walk into the men's bathroom to play some more."

I let the video run but after I turn off the LED light to help keep me in the dark. It was a good thing as soon a car pulls into the rest area and parks not 40 feet away from me but in front of the bathroom's walk way. I carefully back away and around the corner now behind the back wall. I can now hear the guy walking up the path as he horks out a lugi. I can't see him nor he see me. I hear him walk inside the bathroom. It's so exciting to know a man is so close but so far from sissy slut me. I want to run inside and show him faggot, sissy me, but I'm too scared. I just stand and play with my crotch area. A couple minutes later he steps back out and walks back to his car. Once inside I hear him start it, back up. I so wanted him to find me and fuck me.

He is now gone and I'm so fucking horny now I almost wildly walk up and inside the men's bathroom. my video is running. The heels click loudly on the bathroom's concrete floor. Bright fluorescent lighting shows my sissy slut outfit, my make up and wig as well. Right now a guy or guys could walk in on me and it would be scary.

My video running I narrate, "Here is sissy faggot Chantel and here are the toilet stalls, fuck would it not be a blast to suck cock inside one or Mmmm get my sissy ass fucked bent over the toilet?" I make clear with the camera of the toilet I'd either sit on to suck a guy off or be bent over to be fucked for first time in my pathetic sissy life up my sissy slutty ass.

As I keep video running I pull up my skirt with my right hand, pull down my pantyhose and panty. My six odd inch dick is at attention as my right hand begins to stroke it. I am so horny right now I begin to seriously jerk off standing at the counter and a sink. I hold my phone and video myself, my reflection in the mirror. I start to call myself a slut, a sissy, a sissy slut, a fucking faggot whore over and over as my arousal to cum is so high. Soon I moan and groan as I pant and sigh and just like that my sissy dick shoots out a volley of my sissy jizz into the bowl of the sink. OH MY GOD WHAT A FEELING!

I slow down and come back down. Like most or all guys who cum, I get lost in my declining mood. I say to myself, "Fuck, fuck, fuck, why the fuck do I do this? I feel like shit now, so pathetic."

I stop my video and tuck my dick in my pantyhose and fix my hose and skirt. I now just walk out of bathroom and quickly get back to my car. The drive back home is quiet and melancholic. Once at home I sit for a few minutes dressed en femme and soon then strip off my clothes, wash my face and put on a bra, panty and slip to go to bed.

The morning comes and I am feeling sissy girly as I dress up and watch my video from last night. I lounge around a bit and have a coffee. I look at sex and BDSM stuff online and get ideas. Bondage gear including locking wrist cuffs and a cool self bondage tool. An ice lock. You have this two piece kit where you fill with water and let freeze. Once frozen and with bondage gear one can lock themself up and until the ice melts enough you are locked in whatever way you set up.

Fucking cool way to play self bondage. I also look at dildos. Of course like all sissy sluts we all dream and desire the 12 inch long, thick black ones. But I know being virginal up my sissy ass that would be too big, so I look at other choices. Anyways I get some cool ideas and figure maybe I should buy stuff?

Well it's back in 'regular male world' and off to my regular male life job I go. But all day on my mind is BDSM stuff and dildos. Driving home after work I swing by a local adult sex shop. Nervous I step out of my parked car and then inside this shop.

I wander around, nervously mesmerized at the sex and BDSM stuff. It's quite infatuating. Out from the back walks a young lady, attractive but not stunning, tall for a girl, oh maybe 5'7" but in heels she's over 5'10", a black dress and black hose or maybe stockings on her nice legs. Hard to tell as her dress is covering from her knees up. Her hair is long full, straight and blonde. Her makeup is a bit on the dramatic side with smokey eyes and blood red lips. She says, "Hello! how are you today?"

I choke a swallow and reply, "Hi, Good... I'm good."

"So what brings you by today?"

I am so fucking nervous but I keep composed, "Um I was just curious, ya know just looking at things."

She smiles and says, "Well hun, that's ok, enjoy looking, I'll be right over at the counter if you have any question or needs."

I smile and say, "Oh, ok ma'am."

She turns and walks away wearing a gorgeous pair of oh maybe 4 inch spike heel black patent pumps. The lovely click clock sound of her heels on the floor helps make my cock go hard in my panty as I am wearing a black panty without padding and pair of black sheer pantyhose all under my guy clothes. I'm thinking 'Fuck I wish I was wearing a pair of my high heels here with her.'

I walk around a bit, I see some leather stuff for males and females, some sexy lingerie, make up, some super tall heels, and BDSM stuff. As I walk to the counter near by her I see sex, crossdressing, sissy and BDSM magazines. I stare at the covers of the crossdressing and sissy magazines. The lady sees me and I'm not sure if she picked up on my staring at crossdressing and sissy magazine covers.

She says, "See anything you like hun? Do you have any questions?"

I'm thinking, 'Fuck I did not come here just to look, I want to buy some stuff if the store has it." I ask, "Um... yeah...ahh..D...Dildos...you g..got any I can see?"

She smiles and her girl next door attractiveness and her sexy outfit compels me to listen to her reply, "Dildos, yes, sugar we have very many to choose from, come over here." as she walks to an area behind the counter she asks, "Are you looking for a dildo for your girl friend or wife?"

I want to say yes but ask, "Um does it matter much?"

She says, "Well hun, dildos come in different sizes and girths, some girls like vibrating ones, some girls can handle big, very big ones. Using one vaginally may be different than anally?"

I ask, "Oh.. um.. I... I have to be honest.. it is one for me."

She smiles and says, "No problem dear, we will have a dildo that you will like." Sensing my nervousness she adds, "Darlin, don't worry, many men buy dildos for themselves. it can be quite fun."

I say, "It's just all sort of weird for me, I mean my daily life is rather normal and mundane. Shopping for a dildo to use on my self is so odd."

She smiles, "Darlin, don't worry, sexuality is a most personal thing, learning to understand your own sexuality and accept it will only make it more pleasurable for you. Humans don't just fuck or have a****l sex like other a****ls, we fuck and do other sexual things for pleasure. It could be boy, girl, boy, boy, girl, girl or just by your self exploring your ideals and feelings."

I reply, "Wow ma'am you really do make this seem...well, you know, more normal...more ok."

She adds, "It is, it is more normal than you think. Lots of otherwise typical guys love the feeling of a dildo, maybe in their mouth but for most up their backside. It would blow your mind the cross section of guys, age, race, status, gay, bi or straight who get a kick out of dildos. Not just us gals use em to play with." as she giggles.

"Oh ok then," I say.

She introduces herself, "By the way, my name is Jill, sweetie."

I reply. "Hi... my name is Phil. But if I can be more upfront, I'm a crossdresser too and my feminine name is Chantel, I'd enjoy you calling me that please."

"Chantel is a cute name," she pauses and looks at me."You look like a Chantel," she adds more, "So any idea of the type of dildo you may like Chantel?"

I reply, "Um, ah not sure."

Jill says, "Well let me help, now I know that many guys often think getting one like this." As she reaches for one. "big black, thick job. It's twelve freaking inches long and two or so inches thick." she giggles as I look at this monster. "But honey, unless you have a well used backside it may not be one you will be able to use and enjoy. What type of anal play have you done Chantel?"

I'm so bewildered about what we are talking about, "Um Jill, I... I .. guess I'm a virgin with anal play."

Jill says, "That's good info hun. Here lets look at this dildo." she puts the big black monster back on a shelf and grabs a pinkish/fleshy number. "This one Chantel will be an easier one for you to break your backside into the world of anal play. It's about seven inches long and only a bit over one inch in diameter. It's nicely shaped head is slightly tapered to help an anal virgin get it working well. This would be my choice for you dear."

I am blushing but ask, "Um, ok... how much is it?"

Jill says, "$24.95. But you will need a good lube for anal work, let me suggest a good lube especially for a newbie?"

I say, "Ok Jill."

She brings out a tube of lube that is designed to not only give long lasting and very slick effect but ingredients that help relax the sphincter. This tube is also $24.95. She says if I want to have some simulated cock sucking fun with the dildo get some flavoured lube too and she shows me a few bottles of flavoured lube. I choose the four pack, Cherry, Mint, Chocolate, Fruit Punch. It is $29.95.

I ask about wrist restraints next and mention this thing I saw, an ice lock for self bondage? Jill pulls out a few wrist cuff choices and I choose a cute pink and black leather adjustable wrist cuffs. As to the ice lock, Jill brings out the item, it's cylinder type thing with a piece fitting inside. If you fill it to varying levels with water, freeze it and attach it to the wrist cuffs I'm buying it will keep my hands/wrists bound until the ice melts and I can pull it back apart. Jill tells me depending on how much water I use how long I let it freeze and the temperature it is at where I use it the time of locked up effect can take up to two hours. Less water, warmer ambient temperatures and such and the time for the ice to melt will be quicker. It's all trial and error.

This stuff is making me so fucking hard in my pants. I choose to buy all these items with excitement. Jill senses my thrill.

She says, "Chantel, you look as if you will get some good play out of this stuff, I hope you do. I've been selling in this field and helping, men, women, guy/gal couples, gal/gal couples and guy/guy couples explore their sexuality for a long while. It makes me feel good to know I help people enjoy sexuality and play. You are quite typical even if you feel odd here today hun."

I'm feeling good now and smile as I say, "You have been so open, kind and professional Jill. You do not judge me and even knowing I crossdress and want to play with all this while I crossdress. I look forward to maybe buying other toys and such here later."

I had a desiring thought and had to ask Jill. " Um... ahhh... noo I bet... better not."

Jill asks, "Hun, ask me what you want, it's ok I see and hear a lot of hot, cool, sexy erotic stuff."

I interject, "Oh ok, I don't know why but I so want to drop to my knees and submit to kissing your lovely black patent spike heel shoes and run my hands on your stocking clad legs. It's silly, I'm sorry for even saying this."

Jill laughs, "Why not? I see you have had a hard on in your pants since being here. I obviously excite you. How about you drop your pants so I can see you panty and pantyhose?"

I cough and say, "Re... Really? Oh my God, umm... ok, oh my God I'm horny."

Jill takes me more discretely behind the counter and sits on the high stool, extending her legs and heels out before me and has me stand before her. She actually undoes my belt and pant's fly allowing my pants to drop. My black satiny panty and black silky sheer pantyhose is out in the open to be seen. My hard on is like a tent rod.

Jill says, "My, my the sissy is all excited. You may drop to your knees now."

I state, "Yes ma'am." as I fall to my knees. I look up at her and she says, "Go ahead hun, kiss my shoes."

I begin excitedly kissing her heels and it was so erotic, my sissy dick wanted to explode with cum. My hands now delicately run up and down her stocking clad calves. Jill enjoys seeing this but my one hand soon plays with my dick while it still is encased in my panty and pantyhose. I continue to kiss her shoes and my left hand continues to run up and down her calves. But I can't contain myself and I cum in my panty, soaking it with my sissy jizz. I'm am in ecstasy. Soon I do my pants back up and feel deep shame.

Jill asks, "Did you enjoy that Chantel?"

I say, "Um yeah it was great but I feel like shit now, so fucked up as a guy."

Jill clearly states, "Hun never feel bad about your own sexuality. Have fun, you like crossdressing enjoy it. I enjoyed seeing you have fun kissing my heels and rubbing my stocking clad claves with your hand while you jerked yourself off with your other hand."

Soon I am standing back up, cum has soaked a bit of the front of my pants now, but it's ok, Jill laughs and says, "Enjoy the wetness from your cum in your crotch hun."

I'm embarrassed anyways.

Jill says, "Darlin, I'm glad you are happy and growing in confidence. Stop by any time and tell me how you found using and playing with all these things. In fact come by dressed en femme if you wish anytime."

I say, "Oh, um maybe we will see."

The sale is finished, it's a good chunk of cash but I'm so looking forward to trying all this stuff out dressed up as sissy Chantel and as slut Chantel. I give Jill an $20.00 tip for her professionalism and kindness to let me play as such before her. I also want to try all this stuff out at night at the rest area soon.

The drive home was fun as I was horny and once home I dressed up as Chantel in my pink maids dress, white tights, pink 5 inch spike heel pumps, and a wig and makeup. I did not leave the house but I did get into playing with the dildo and try a freezing of water in the ice lock to see how long it takes to melt. I masturbated in my pink maids dress, handled the dildo and even messed around licking it trying out the flavored lubes. It was very exciting for the sissy in me. Thinking about when I will try it all out at the rest are was. I soon could not contain myself and ejaculated into my panty. Future fun how that will go we should soon see.




Well about a week has gone by since I bought the dildo, wrist cuffs, ice lock and the lubricants at the adult sex shop. Dressing up as a sissy maid or a sissy slut everyday at home and learning how to use the dildo first with my mouth and trying out the flavoured lubes for added pleasure, but mostly getting the hang of fucking my butt hole with the dildo. I mean it has been an incredible sexual pleasure to feel a dildo up my sissy, slutty ass. Getting it to give me a prostate pleasure while I would stroke my sissy dick to orgasm has been fucking incredible. Doing it all dressed up either as a sissy maid or a slut puts me over the top in sexual emotions.

I also tried out the ice lock and found if it is filled full with water, left to fully freeze will take at room temp about 2 hours to melt enough to pull it apart. Outside on a cool evening I found it takes about 2.5 hours. Filling it less than full does shorten the time for it to thaw out. Before I try it out at the rest area on a late night play session I will decide how much to fill it with. The pink and black leather, padded wrist cuffs turn my on too.

Anyways it's a Friday night and after coming home from my rather typical, regular day job, having dinner and then working to get ready. I found with ass plugging if I give myself a good enema first makes my back side cleaner for such play. So I am stripped to the nude I have a enema kit ready with a hot water bottle, hose and a tapered end. Once filled and the tip lubed along with my butt hole I stand in my shower and fix it up my back side, unclip the hose as water flows inside my rectum. What a weird feeling as my rectum fills with water. I take as much as I can stand then clamp off the hose. I stand in my shower bent over and let the water settle in my rectum. After I could not stand it anymore I quickly make my way to the toilet and evacuated the water. My bottom is now fresh and clean.

Back in the shower, then a close shave to then do my makeup and to then dress. Tonight I'm going to dress as a slut. Going through my clothes I select a white satin and lace padded panty with a matching white bra. I put in my breast forms and a white camisole over top. I grab from my femme clothes closet a white satin blouse and put it on. I pick out one of my white lacy garter belts and put it on. I then sensuously pull up each leg white, silky sheer, lace top stockings, clasp the garter straps to each stocking and stand up. Mmmm so sexy, so fine and so sexy.

I then pick out a black faux leather mini-skirt. It really does not cover the lace top of each stocking and makes me look more hot 'n sexy. My auburn with blonde hi-lites wispy, shoulder length wig and its cute bangs frames my quite feminine face nicely. My sissy dick is rock hard in my panty. Some 2 inch diameter hoop earrings and I'm now off to pick out a jacket, black cropped leather jacket will sex my look up even more. Now for my heels. Hmm so many shoes and boots, what is a girl to do. I choose a pair of pink, patent 5 inch spike heel pumps with pink ankle straps. Off to the full length mirror and Yummy I look so girly, so sexy and so slutty.

"Chantel darlin, you look fucking hot. One fucking hot tranny slut."

I put my dildo, lubes, wrist cuffs in my purse and I wait until it's late. My nervous excitement about another venture out to that rest area is so wild. I plan on sucking my dildo, fucking my ass with it and using the ice lock to restrain me via my wrist cuffs somewhere at the rest area. I will then have to wait until the ice melts before I can free myself. Of course I know I will be discrete to only tempt fate of possibly being seen or caught and if that were to happen deal with it. Mmmm, maybe it will mean my slutty self finally sucking cock for the first time or more so having a guy or guys fuck my slutty ass. Who knows, it's all a part of the excitement of fate.

It's about 11:00pm. Friday night. I grab my purse and keys. I like as I always do, open my front door and scan to see if any persons are out and about. Feeling ok I quickly scamper in my heels to my car and get inside. My heart is again racing with adrenaline, I sit inside my car and let it warm up as I try to ease my nerves. Tonight is a crisp but clear night, the 1/2 moon shines bright. I soon back out of the driveway and am on my way to the rest area.

It takes another 15 minutes and once I get there I pull off the road and up the drive way to the fairly large parking lot. As I get in I see two cars parked near the pathway to the bathroom building so I choose again to park a number of spots away, oh maybe 50-60feet away from the next car. The seeing other cars makes me more nervous but also more excited.

Soon I do see one guy walk out from the men's room and to his car get in and then drive off and a minute later I see another guy do the same. It's now about 11:20pm and I am alone in my car here. I pull out my cell phone and turn on video mode to talk about myself as I with the video LED on show my made up face and my clothes. I talk about how I plan to play with my dildo both with my mouth and my ass. I plan on locking my arms via the wrist cuff a long steel cable used from a Kensington lock and the ice lock somewhere at the rest stop. As I make my video I see another car pull up. I quickly end my video and sit in my dark car. I think, 'Damn this place is busier than I thought, fuck it scares me. I guess being Friday night it may just be a busier place.'

I watch this car park near the walk way to the bathroom. Moments later I see a guy and a gal get out and walk hand in hand up the pathway. I next see both of them enter the men's room. I think, 'Huh, hmm I wonder are they going to have sex in the men's room?' I sit a few minutes in my car and realize they must be having sex as doing one's potty business will not take that long. I'm really turned on by it all. I figure, fuck it get out of my car and walk towards the bathroom.

I turn my video back on with no LED light as I step out of my car, stand tall in my heels and close the door, keys in hand. I begin to walk towards the bathroom, but my nerves keeps me out of the light and off the walkway. I venture on to the grassy area and quietly walk to the building. Off to the side and I stand quietly. I listen and I hear what does sound like sex. Mmmmm I love it, I wish it was me having the sex with the guy. It sounds like he is fucking her as she moans loud enough to hear from outside here.

My sissy dick is rock hard as I play with it rubbing my panty with my right hand. God, I so wish it was me being fucked by this guy. I stand and enjoy eves dropping them having a great and taboo sexual time.

Soon I hear him grunting and she is really moaning. I'm thinking, 'Fuck I want to walk in on them and beg him to fuck me next as I'm such a fucking horny slut.' I hear them finishing as he groans and she moans to the sounds of like he is cumming in her. My mind melts with lust.

A couple minutes later they open the door and walk out, I scoot back from the side of the bathroom so they wont see me. I see they get in their car and drive off. Wow, that was fun to hear. The thought of them fucking in a public bathroom was so hot.

It's now about 12:00 midnight, I'm alone, I figure to go inside the men's room to soak up the atmosphere of the sex that a guy and gal just had inside. I step inside and it's brightly lit and I walk around in my heels. I picture the guy and gal using the counter to have sex. I think, 'Mmm would it be fun especially for him as he'd be able to see their reflection in the mirror.' I took a moment to think about it being me the one being fucked. I wonder if they used a condom? I snoop inside the garbage can as I did not hear a toilet flush. Opening the lid of the garbage can and my eyes go wide open. I see a fucking used condom. I reach in and pick it up. I think 'Oh My God,' I hold it in front of my face and see the guy's fucking fresh jizz in the condom. I'm thinking, 'Jeez this condom was on the guys rock hard cock and up his gal's vagina. The nice amount of fresh jizz intoxicates me. I think I should swallow it.' But I wait I get back outside and I walk towards an area of the rest area where there are covered picnic benches. There are two I go to the one a bit further away from the bathroom. It's is also easily 100ft. or more away from my car.

At the picnic table I pull my dildo out from my purse and its suction cup base holds it on the table top. I put on my leather wrist cuffs and a cable that wraps around the base of the table and I secure it with my ice lock. Once all clicked I now know I' m trapped here at this picnic table until the ice melts enough to pull the lock apart. I estimate based on how much water I froze and the fact it has been melting in my purse, I will be trapped hear for at least an hour or more. Next I take that so cool jizz filled condom and pour the jizz over my dildo. I quickly place my mouth over the dildo and slurp the cum as I suck on the dildo. I'm so fucking horny, my sissy dick is rock hard in my panty. I lick out the rest of the jizz from this used condom. I am in sexual arousal heaven.

I now take the tube of butt lube I bought at the adult store and pull my panty down. I finger lube my butt hole and this butt lube has ingredients that are to help relax the sphincter. Now I'm lubed up I begin to work my dildo up my sissy ass. It hurts a bit but it feels so fuckIng good. Here I am out at a public rest area, late at night, locked to a picnic table, dressed as a sissy slut and pounding a dildo up my butt hole. I am stroking my sissy dick with my right hand as I work the dildo up my butt with my left hand. It is such an incredible feeling. A part of me wants to get myself aroused to cum quickly, but knowing the ice lock will keep me here for probably another hour or so I make sure to slow down, enjoy this wild ride of feelings, the joy of being dressed as a feminine, slutty girl, the fear of being caught and the arousal of fucking my ass with a dildo as I stroke my sissy dick.

I am working away when I see headlights, as I watch them I see they slow and pull in the rest area parking lot. I am very nervous now and I crouch to hide behind the picnic table. The car parks near the walkway to the bathroom. I peek to see what is going on. The car is about 70 feet or so away. I see two guys step out and begin to walk to the bathroom. I can hear them faintly talk.

First guy, spits to the ground. "Damn, I got to take a dump."

Second guy, "Yeah and I got to piss like a race horse, all the beer has gone through me."

First guy says, "Well at least you don't have to piss against a wall." as he laughs.

I see both of them enter the bathroom. I remain quiet and hidden as best I can. A few minutes later they step out and walk back down the walk way. They stop and begin to talk.

First guy, "Hey you still got that joint?"

Second guy, "Fuck yeah, you wanna smoke it?"

First guy smiles and says, "Ok, lets sit at a picnic bench over there."

They begin walking my way, I think, 'Oh shit, no, no, no, please not here by me.' I see they come closer and thankfully for me they choose the covered picnic table that is to my right and closer to the parking lot, about 30-35 feet from me. I stay quiet like a mouse, my dildo still up my ass and I crouch low but try not to move or make any noise.

They soon sit on the picnic bench top table, sorta 3/4 turned backs to me. Whew, they will not see me so easily. But I'm scared shitless. They light up the joint and smoke it between them. They chat away.

First guy, "Did ya see the waitress at the bar tonight? Talk about fucking huge tits in her low cut blouse."

Second guy, "Yeah and she had a nice ass in her mini-skirt too. She was pretty hot."

First guy smirks, "Fuck I need a new girl friend. Fuck it sucks since Jenny and I broke up."

Second guy laughs a bit, "Fuckin right, I could use a girlfriend now too, gotta fuck sometimes. But man Jenny was pretty hard ass on you, I mean sorry man but she did try to wrap you around her finger, going all feminazi on you."

First guy grunts, "I dunno, but we had some fun and she was fucking great in bed. I dunno fucking chicks today are all so feminazi."

Second guy, "Tell me about it, I just don't get it, like what the fuck do they want?"

First guy laughs, "Your money and your ability to do things for them or they will hold sex from you."

Second guy, perturbed, "Shit yeah, I dunno sometimes you think a fuck buddy girl is all you as a dude really needs."

First guy laughs again, "A fuckin tranny... Fuckin trannies, I see them as possible fuck buddy chicks."

Second guy, "Whaat! a chick with a dick? Why would you turn faggy gay for one?"

First guy, lightly slugs the second guy on his shoulder, "It's not gay, I mean do you ever see em online, some of them are fucking hotter than real girls. I mean man fuck I have come home after a few beers and watched some tranny porn, I mean fuckin eh! it's a good way to jerk off."

Second guy pauses and then says, "Well yeah you got that right, trannies at least on line look pretty hot. Yeah I've jerked off to them too. It's not all that bad I guess, as long as I can get off when without a girlfriend or real chick to fuck."

First guy, "Well I figure they will probably know what guys want as well ya know they are still dudes even if they look and act as hot chicks."

I remain silent, crouched down and can't believe what I am hearing. A part of me wants to stand up and tell them I'm tranny slut, I look pretty hot and yes, I know what guys want. Another side of me wants to keep quiet. Guys talking shit about messing with trannies is one thing, doing it is another. Well back to listening to their talking.

First guy, "You know all this feminist shit, fuckin girls get mixed up in it and fuck as a dude you just don't know what to say or do at times."

Second guy a bit angry says, "It's those dyke activist, feminists, they fuck up the minds of other girls. Well shit man you and I ain't gonna fix it."

First guy, inquisitively asks, "Would you?"

Second guy, smirks, "Would I what?"

First guy, "Get it on with a hot lookin tranny girl? I mean picture a tranny in a short skirt, tight top, even plump fake boobs or shit maybe one with implants, sexy heels, well made up face and cute hair. Picture her wanting to go down on you, would you?"

Second guy, "Well it's been so long for me sex wise, yeah I'd let such a tranny go down on me. It could be fun."

First guy, "Well you never know. Anyways the joint is done, I feel pretty good, we should go. Maybe check to see if Gary is home."

Second guy, "Yeah it's like after midnight, I feel a bit baked so yeah lets go, but lets get some munchies first."

As they begin to walk away a part of me is so fucking turned on I want to call them and show them I'm a sexy tranny and would go down on them. But I'm too scared so I just quietly watch as they walk to the car, get in and drive off. I'm so fucking horny I begin to now seriously bang my ass with my dildo as I stroke my dick. Soon I groan out loud and standing I see my sissy dick shoot out its wad of cum on top of the picnic bench table.

I say to myself, "Fuckin eh? fuck, fuck, fuck, feels so good."

I come back down and soon rest on the table as I feel a bit blah. I pull the dildo out and I ease myself stress wise. I am though stranded here locked up until my ice lock melts and lets me be free. I try to pull it apart but no dice. I sit and wait, locked up. I think about the talk the guys had. I really see where a good tranny can be a good fuck buddy girl to guys who have needs. About 12:30am finally the ice lock melts enough for me to free my bonds.

I am calm as I put things away. I quickly scamper in my heels back to my car and drive off. What a night! wild ride of emotions. Parked in my car at a rest area I see people come and go, outside and hiding I hear a guy and girl have sex in the men's room. I snag his jizz filled condom from the garbage and swallow it as I play with my dildo. I then fuck my ass with it to then hear two dude chat stuff and about sex.

Good memories from tonight. I know I will do this stuff again and often. Where it goes who knows.



Another week [Friday] goes by since my last visit to my new favourite play area, that rest area. But it's not that I have done nothing. At home after work, dressing as a slut or a sissy maid and pounding my ass with my dildo while jerking off is getting my ass use to being filled with cock. But it's one thing to play in the privacy of my home, it's another to go out even late at night in a public place.

So after an enema, I shave of any new body hair, shower, face shave, apply my make up and toss on my auburn with blonde hi-light wispy shoulder length wig. I'm back into dressing like a slut. Tonight I put on my sexy black garter belt, pull on each leg black silky sheer stocking with sexy lace tops and cute little satin bows. I pull on a green suede mini-skirt and a red satin blouse. I gather up my frozen ice lock, leather wrist cuffs and the long steel cable, put it all in my purse with my dildo and lubricants. Step into a pair of black suede 5 inch spike heel pumps and I put on a black faux leather cropped jacket.

My nerves are high and my excitement is high. It always is as I plan a drive back to the rest area off 'Apple Grove Road'. But like previously I am soon sitting in my car and warming it up. My sissy dick is rock hard in my black satin padded panty. Soon off I drive and about 15 minutes later I am pulling into the parking lot of the rest area. I see a couple of cars parked there again, so I park a bit away from them as I wait to see if I get some privacy.

The other cars are just for guys coming and going to the men's bathroom. Soon they are all gone. I'm very excited now as soon I plan on stepping out of my car and doing play things as a slutty crossdresser. I pull out my cell phone and make another video to hi-light where I am and how I'm dressed, doing so holds me back from stepping out of my car dressed as slutty Chantel. Good thing as a car pulls into the parking lot, so I stop my video and observe it. It parks near the walkway to the bathroom. I see two gals step out and they are dressed in tight pants and heels. They both walk into the ladies bathroom. Oh I so want to walk into the ladies bathroom and let them see slutty me, but I sit in my car and play with my hard dick.

A few minutes later they both walk out, back into their car and soon drive off. I look at the clock in my car and see it's about 11:30pm. I now decide to step out of my car for a night of arousing play for myself. As I plant my high heeled feet on the pavement I feel the rush of cool night air around my stocking clad legs. I grab my purse and keep my keys in hand as I shut my car door. Almost robotically I begin walking to the bathroom. I'm not really sure what I plan I have to do tonight. I decide to bypass the bathroom and walk back to the covered picnic table I was at last Friday.

Once at the table I decide I will lock myself to the table again, but tonight instead of the back side where I can duck and hide from view more easily, I'm going to lock myself to the front side where I will not be able to duck and hide if people see me or walk near by. If I want to tempt being seen and caught I have to push limits.

I pull out from my purse a four foot long vinyl covered steel cable used in Kensington lock for computers. I take my wrist cuffs and strap them on my wrists. I pull out my frozen ice lock and begin my self bondage. I slip the cable through the ice lock after I wrap it around the base of the picnic table. I then run this cable through each wrist cuff's rings and using small padlock lock on my right wrist cuff [keys for the padlocks are still in my car]. I then make my decision, if I click the lock closed I will be bound here until the ice lock melts and then lets me separate this cable from the base of the table. I figure it will take an hour or so to melt enough. So it's time to make my choice, I can back out pack up my stuff and scamper in my heels back to my car, or I can with a click of a lock have me kept here all be it late at night now about 11:45pm. If a car and people come by, they may see me as I will not be able to hide so easily from sight this Friday night. I'm so fucking turned on by this I just go ahead and click the padlock closed.


I think, 'Well it's done, I'm locked in place. No escape until the ice lock melts.' My sissy dick is rock hard. I can move my hands enough to play with my dick. I also am able to pull from my purse my dildo. I suction cup it to the table top. I pour some wild cherry flavoured lube on it and I am now sucking the dildo off. I only wish it was a real man's cock. I am so fucking horny and close to ejaculation, but I stop and ease up. After all I'm hear for about an hour or longer, no sense in rushing.

As I try to balance the ecstasy of jerking myself off until I come from sucking my dildo and trying to just take it easy and enjoy the passive thrill of my bondage until the ice melts enough to allow me to pull it free.

Minutes pass and soon I see car headlights slow and pull into the parking lot I begin to get very nervous and think, 'Oh no, I hope whoever it is does not see me here like this.' as I crouch down into a ball, even though I am out front facing the parking lot and bathroom building. The car parks and I see two guys step out and begin to walk up to the bathroom. They have not seen me, but I reman still, crouched and quiet.

Minutes later they walk out and are talking to each other. I notice something familiar, these are the same two guys who were here last Friday night as I hid from them an eves dropped their conversation.

First guy says, "You wanna smoke another joint here?"

Second guy says, "Ok sounds good. Lets go sit at that picnic table again."

First guy says, "Ok."

They start walking my way, this is it, they will surely see me. I try to be inconspicuous but I'm right out in front, yes it's dark but lighting from the parking lot does shine on me enough to be seen if a person looks my way. I await what may happen.

"Hey man, you see what I see?" First guy asks.

Second guy says, "It looks like a chick, crouching by the table."

They keep walking but now towards me. "Shit man that ain't no gal, it's a tranny slut." First guy says with excitement.

Second guy, "Well shit, look at this, what kind of faggot are you and why are you here dressed like that?"

I nervously reply, "Please I don't want any problems, please don't hurt me ok?"

First guy says, "Hurt you? Nah you look pretty damn cute and sexy, those stockings showing, you in your mini-skirt, make up and heels."

Second guy says, "Look, she has bound herself to the bench, how do you plan to get out sissy?"

I reply, "Um, it...it's an ice lock. When the ice melts I will be able to free myself. It will take about an hour or so."

First guy says, "So what you hoping to get caught or somethin?"

"Um I guess I was playing with the possibility as I jerk off in my panty and stuff. Um but maybe now having you two see me, maybe...um... maybe I can...um... suck you off. After all is that not what you both want?"

Second guy replies, "We want? You sayin we want you to suck us off?"

First guy (clicks fingers) says, "No shit, you must have been here last week, you know when we talked about a tranny going down on us."

I reply, "Um... yes.. I was here at this bench but hiding on the other side, you...you two were talking about it."

First guy, "Hmm man why not, this slut wants to suck some cock, why not give it to her."

Second guy, "Sure lets feed her some cock, I bet she is hungry for some hard cock, right bitch?"

I am nervous and reply, "Um...ok.. but as ..much as I want to... be a slut, I have never sucked cock."

First guy says, "What's your name you faggot slut?"

I reply, "Um it's Chantel."

Laughing he says, "Cute name for a sissy slut, well Chantel, my name is Barry and my bud here is Ralph. It's time for you to learn how to suck cock, ok you slut?"

I'm shaking with nerves and excitement, "Ok I...I will suck your cocks."

Years of fantasy for such for me has finally come to this moment. Dressed as a faggy, sissy slut out at a rest area, in bondage and now about to suck my first cocks.

Barry has me undo his pants and pull them down along with his briefs. Out plops a nice thick 6+ inch cut white cock. Barry fondles it with his right hand making sure it's ready to be sucked. "You like what you see you bitch?"

I look up at him and reply sheepishly, "Uhh...umm, yes... yes sir, you have a lovely cock."

Barry now says excitedly, "Suck it Chantel, show me the sissy slut you are."

So I take his stiff cock in my right hand and with my left hand I cup his balls, this is it, I nervously move forward with my head and open my mouth as his stiff leathery cock slips inside my mouth. The most incredible feeling comes over me as I am doing something I have yet to do but fantasize about most of my life. Barry's cock slips in nice and I try to get a feel for it as well as build up saliva to suck on his engorged cock. I hear Barry moan as he feels his cock in my mouth. I get to work and like a good slut I begin to slurp and head bob. His stiff cock and swelled cock head is intoxicatingly inside my sissy mouth.

I think as I suck, 'Wow what a sight it must be a fag sissy slut like me, bound to a picnic table on my knees and a cock of a man I just met now inside my mouth.'

Barry is groaning and I'm moaning as I continue to take his cock in my mouth. Ralph coaches me on to doing a good job sucking Barry's cock. I really do develop a feeling and desire to please Barry. I want to be a good sissy cock sucker. Barry is working his way to an orgasm I bet he never figured he'd get tonight and by the mouth of a new sissy cock sucking slut. As we both work to bring him to his joy and what will be my prize, I keep head bobbing and sicking his stiff cock.

Ralph adds, "Suck him off well bitch or we may have to beat the shit out of you."

That scares me and has me more want to please Barry.

Barry now panting with growing joy says, "Oh God feels good, Chantel is a good lil slut. You gonna enjoy your turn with her Ralph."

Barry is getting closer and I can sense what will soon be happening, a cum shot inside my mouth and I know Barry will want me to swallow. As he gets closer and closer to cumming inside my sissy mouth my mind wanders for a moment, 'This is what it was like for my now ex-wife as I fed her my cock when I still thought my cock was a cock that belonged to a real man. Huh! funny! I knew my cock was not a man's cock but only a sissy dick.' as I come back from my thoughts I feel hands hold the back of my shoulder length wig covered head and I hear a major grunt and sigh as Barry now fills my mouth with his hot, gooey, lovely cum. For the first time in my life I have a man fill my mouth with his hot, tasty and all domineering jizz. I swallow it up as best I can as Barry slows and then pulls out, his cock flops in front of my sissy face.

Barry now asks as he firmly grasps my chin with his hand, "Did ya swallow bitch?"

I open my mouth and even though it's dark he looks to see his jizz all yummy swallowed by sissy slut me. As he now backs off, I see Ralph come and he stands by my face his also 6 or so inch slightly thinner cut white cock dangles in front of my face. I show to Ralph my desire for his cock. The world of being a slut is filling my mind. Ralph orders me to take his cock in my wanting mouth, to which I do.

As his warm leathery shaft now slips through my lips and my wet tongue takes hold of it, my sissy dick is also hard. I begin to slobber over Ralph's cock as he begins to moan. I love the sound of a man in lustful moan. We both do the cock sucking dance together as he throbs his cock in my mouth and I do the sissy slut head bob. All the sound reverberating around us is, "Mmmm...uhooh...ummm..ahhh. Mmmm...ugh...mmmm...ohhhh...mmmmm." by both of us.

Ralph is now in hot horny, full heat of lustful passion for his cock being sucked by sissy slut me. He pets my head with his firm hands as I continue doing the cock sucking head bob. My saliva works his hard shaft beautifully in my mouth. My mind is near delirious, I mean here I am dressed as a slut in a public rest area, sucking the hard cock of a real man. Certainly Ralph did not think he'd too have his cock sucked by a sissy slut tonight but here he is. My desire to please him is so effeminately strong.

We continue to work together as I bring ever closer to having Ralph cum in my mouth. Between his ever more hard core groans and grunts along with my sissy slut moans, he gets closer and closer to cumming. I feel his hands now firmly grasp the back of my head with my long wig hair around his finger and palms. His cock is so hard as he lets out a deep groan and thrusts his stiff cock deep in my mouth and shoots out a thick, hot, gooey wad of his sperm filled cum. I almost gag as I take it and swallow it all, but swallow I do.

Ralph, sighs, slows and pulls out from my mouth. His right hand grasps my chin now too, tilts my head up as I see his pearcing eyes look at me, "Fucking open up, show me your mouth you bitch. You better have swallowed my gift of hot jazz for you."

I open my mouth, showing him that every bit of his cum was happily swallowed by me, and say, "Thank you sir Ralph."

I stay on my knees as Ralph tucks his cock back in his briefs and pulls up his pants. The both of them compliment me for being a good sissy slut. I continue to stay on my knees as I await their further actions.

Barry says, "Ok bitch, good job, here is what's going to happen. Next Friday night by 11:30pm you shall come here dressed as a sissy slut. You will service not only my and Ralph's cocks, but we will bring you more guys to have their cocks serviced. You will also beginning next Friday night also have your butt fucked, you got it Chantel?"

I meekly reply, "Yes sir, I will be here next Friday night for servicing more cocks."

Barry adds, "You'll enjoy it girl, sissy sluts like you love cock." He adds, "I will call you prior to your leaving to come here again next Friday. I expect you to be 100% compliant. I went through your wallet and see where yo live. Failing to be her next Friday by 11:30pm will result in big trouble for you, you faggot slut."

I sheepishly reply, " Yes, sir, I understand your orders sir. I will be here next Friday to be used by you sir, sir Ralph and your other males friends who will come out too."

As the two of them now leave I am mixed between humiliation, lust for my new slut life and despondent about how these men are taking control over a part of my life. They get in the car and drive away, I collect my thoughts, pack my belongings and wait for the ice lock to melt.

But my sissy dick is still hard and I can't not want to stroke it and work to jerk off now. I am excited with all that has happened and my turn on to cum is soon here. Just a bit more stroking of my pathetic sissy dick and I will cum. I soon let out a clear list moan as my sissy dick before my eyes sprays out a wad of my sissy cum on the picnic table top.

I am delirious in ecstasy, but I now soon crash and feel like a humiliated piece of dog crap. I think to myself, 'Fuck why have I grown up to be so fucked up? Why do I so want to be a cheap, skanky, sissy slut and floozie?' Once I relax, wait for my ice lock to melt and set me free from my self-bondage I then scamper to my car, my high heels clicking away and get in it. I sit, music playing and ease into a mindset of a sissy slut to then go home alone. I think about what I was told, 'If I fail to be here next Friday they will come to my home and beat the crap out of me.' They and I all know, I will be here as we all know that I am a sissy slut.

Once back at home I'm feeling horny again and I watch the video of me sucking Barry's and Ralph's cocks, it drove me to masturbate until I came my sissy sperm filled cum in my panty. This coming Friday night rendezvous may actually be quite fun. I do look forward to being butt fucked too. A part of me is terrified another part can hardly wait until next Friday night..


Well another week has passed by, it's Friday evening and tonight I have to go back to the rest area to hook up with Barry and Ralph as they instructed from last Friday after having me suck their cocks. They promised me that they will fuck me tonight and share me with even more men. My nerves are going wild as I lust for this slutty situation I am about to embark on but also for fear of what has and is becoming of me.

Once I complete my enema, take a shower and shave, I then prelube my butt hole, make my face up and put on a short black velvet party dress with lace detail, a dress that is very short thus fully exposing my black sheer stockings and the lace tops with sexy garter straps. I put on a black faux leather cropped jacket, my auburn and blonde hi-lighted shoulder length wispy wig. I grab a pair of red suede 6.5 inch spike heel pumps on 1.5 inch platforms. Spritz on perfume and I'm pretty hot looking tranny slut.

Sirs Barry and Ralph want me at the rest area by 11:30pm and in the men's bathroom soon after. My drive out is both exciting and nerve wracking. I think about being fucked up my sissy slut ass tonight, fucked up my ass for the first time in my sissy life. I'm going to lose my anal cherry to either Barry or Ralph. My sissy dick is hard in my satiny panty as I think about what will be happening to me tonight.

I am soon at the rest area and park near the bathroom. Another car has just left and I'm alone. It's just past 11:20pm and I know I must wait for the men while being inside the men's bathroom, so, pop open my driver's door, swing out my stocking clad legs and plant my 6.5inch spike heel red suede platform pumps on the asphalt. Again the cool night air wistfully caresses my sexy stocking clad legs. I begin to walk to the men's bathroom in my sexy spike heels. That lovely click clock sound of heels on asphalt is such a turn on for me. I walk to and inside this bathroom. I now nervously wait, hoping no other people show up except for Sirs Barry and Ralph along with any other men they shall bring.

Time ticks by and about 11:30pm I hear cars pull up, my nerves are frazzled. I think, 'Is this Barry and Ralph along with other men? Is this other strangers? Surely in moments people will likely enter this men's bathroom. Of course it could be women about to use the ladies bathroom but I doubt it.' I prepare myself for what will likely soon happen. As I stand tall in my heels I hear footsteps come close and men's voices, this is it, I'm scared but my sissy dick is rock hard in my panty with excitement.

The door opens and entering is Sirs Barry and Ralph. They immediately see me and smile. Behind them are two other men who upon seeing my faggot slutty self start to laugh. My face is blushing.

Barry says, "Well, well, well, looky here, our little faggot slut is hear as told to be by us. Are you excited Chantel?"

I reply with a curtsey, "Umm...ahhh..y...yes sir..oh my God... I'm scared ...bu...but excited. I...I hope you all... um like ... the way I look."

Ralph replies, "You look fucking great you slut. Guys this is sissy Chantel, our tranny slut for tonight."

Ralph goes to introduce me to the two other men, Mark and Rick. They all love seeing faggot me. To them I look ready to fuck and fuck me they will tonight.

Soon Sir Barry directs me to the sink counter, face the mirror and bend over. He has his hands then ease up my way too short dress which reveals my satiny black satin panty and my garter belt holding up my black sheer stockings with their lace tops. I am now to pull my panty down exposing my virginal lily white sissy ass. The men are all hot for what they see. They all note that they have big hard ons and look forward to fucking my ass. I find Sir Barry will be the first and will take my anal cherry. I am to ask him to take me.

I sheepishly ask, "Please Sir Barry, please take my cherry. I need and want real men to show me what I am, a sissy slut, horny for sex with men."

Barry laughs, walks up behind me. I hear his pants being undone and drop, then he pulls his briefs down popping out his 6+ inch stuff white cut cock. He makes sure guys are recording this on video for future playback.

He says, "I'm gonna enjoy fucking your tight little ass Chantel." as his hands now firmly grab my butt checks and play with them. He is being cheered on by the other guys and he soon is pulling my cheeks open to show him my lubed up butt hole. I'm so damn nervous and am panting waiting for his inevitable invasion of my sissy butt hole. I want it badly but also wish it was not to happen. I let out a notable "Ugh!" as Barry pushes his cock up my hole.

I am now panting and sighing as Barry works up to a good fucking rhythm. It really hurts to begin with, I'm between pain and delirium his tool works my hole and prostate. I can't help to see our reflection in the mirror and think, 'Damn this is happening, I'm finally after all these years, dressed as a sissy slut and being fucked up my sissy ass, shit what kind of life I now lead. A few weeks ago it was all a secret in home crossdressing thing, where I'd dress up, prance and mince around the jerking off. Now I'm some slut being used by men.'

I come back from my thoughts when Barry grunts and thrust harder. Between him grunting, groaning and panting with my yelps, moans and lustful cries we work well together as fucker and fuckee, me the faggot sissy slut being the fuckee. The other men video it all and cheer us on and it's so fucking hot and horny, my sissy dick is rock hard too and Rick notices it to point out how much I am enjoying this from my rock hard sissy dick.

Ralph notes, "She's a faggot sissy slut, this sort of shit is what she and fags like her want, right Chantel?"

Between panting and moaning I reply, "Ye..yes, sir... ugh.. sir Ralph, yes... ooh...ooh yes I... I love it.. ahhhh fuck I ... love it."

Barry is now sweating as he thrusts his stiff cock like a wild boar up my ass, drips of sweat falls from his brow and on my lower back, he pounds away wanting to make sure this first butt fuck for me will never be forgotten, and I know it won't. I can sense him working up to his goal of a strong ejaculation deep inside my rectum. We moan and groan together as he works it all up and soon a big thrust with a loud grunt and Barry lets go his volley of hot, sticky cum deep inside me. My first butt fuck to completion as we both begin to come back down. Barry now pulls out, leans forward and tells me it was fucking great and for me to stay there as the next guy will now take me. I am lost in humiliated thoughts but lust for now being a cheap slut, knowing three more men will have their way with me.

The next half hour goes like this Sir Ralph, then Rick an Mark each have their way to fuck my now wet and cum filled ass. To be fucked by four men and all me dressed as a slut is the most erotic thing to happen to me. I am full of male shame but sissy lust to. Each guy is happy after cumming inside me and I am grateful for them helping me see I am a sissy slut.

As this evening wraps up, Barry tells me I will be back here next Friday night to do it all over, but next time I am to wear a maids dress, stockings, heels, wig and make up. I curtsey and agree. The men now walk out leaving me alone in the men's bathroom.

I am lost in humiliating thoughts but also in ecstasy of all that has happened. Alone my own erotic horniness has yet to be fulfilled and I soon am playing with my sissy dick, reliving the butt fucking I just went through. Looking at my reflection in the mirror I find I begin to shoot out a load of my sissy cum into the bathroom sink. I come back down and agin feel deep shame but soon I too walk out to my car and my sissy ass sure feels like an ass ravaged by hard male cock. I sit in my car and think about my life to date. I listen to some music and the broken male in me cries a bit as he is lost and faggy sissy me is out front now. I soon suck it up and drive for home. I think these men have video of me being fucked as such, I hope they keep it all private.

Once home I quickly walk into my house and undress, shower carefully washing my ass and trying to get as much the cum out of my hole I can. Soon I fall into bed and think about next Friday before I fall as sleep.

As the next days pass by I relive in my home and my mind the last Friday night events. My growing sissy slut ideals captivate me. My male side wants to run away from these thoughts. I am tossed between my sissy lust and my male normalcy. What I do not know are plans Barry, Ralph an the other men are working on for me for the following Friday night venture.

I think to myself, 'How long will this sissy stuff at the rest area go on? What will come of this and my life? Will these men grow tired of a pathetic sissy like me?' I go between these thoughts and dressing up and playing with myself at night in my home as each day ticks past. Soon it will be Friday night and I will have to prep and dress for another degrading sissy slut night at this rest area and with these men.

Meanwhile Barry and Ralph are on the ball with some very special things to happen to me this Friday night. Of course I will know nothing of it until it is presented to me Friday night.

[Friday Night]

I am now home from my regular day job, I have some dinner, feeling nervous but also excited about tonight. I now begin my preparation and dressing for my Friday night rest area sissy slut session. Enema, shower, shave and makeup. I then put on my black satin with white lace maids dress over a fluffy white petticoat. I was told to wear black sheer stockings and garter belt, which I pull on and clasp. I then fill my purse and put on a black cropped jacket, step into a pair of black suede 5 inch spike heel pumps.

My stomach turns with butterflies as time gets closer for me to get into my car and drive out to the rest area and await the degrading sissy sex I will be having tonight. The drive is quiet, my car stereo is on low volume as my mind drifts from driving to what may happen to me tonight. Too think soon I will have men fuck my sissy ass again and tonight with me dressed as a sissy maid scares and excites me, as I know I want it. My car stereo clock shows 11:25pm as I pull in the rest area. It crisp and dry tonight as I park and sit for a few moments to see if I am alone.

Seeing the rest area empty of others I soon open my car driver's side door and step out in my 5 inch black suede pumps. I quickly scamper to inside the men's bathroom, all nervous as I wait by sitting in one of the toilet stalls, just in case others come to use the bathroom before Sirs Barry, Ralph and their buddies arrive. My thoughts are 'Boy am I scared, I know anal sex for me is still going to be hard and painful but boy do I want to be fucked up my sissy ass tonight.'

Time ticks by and soon I hear a car, it could be the men, I wait inside the toilet stall. The door soon open and footsteps are clear as men walk inside this men's bathroom at about 11:35pm.

Sir Barry speaks, "Where is my sissy bitch Chantel?"

Of course I know to stand up and step from the toilet stall and smiles of four men are wide as I curtsey and greet them. "G..Good evening gentlemen, sissy Chantel at your service."

Barry says, "Yep there is my little sissy bitch, you ready to get fucked by some hard cock again?"

I sheepishly reply, "Yes sir, how ever you wish sir."

The guys are all stroking the front of their pants trying to ease their ever growing cocks inside their pants. I'm ordered to face the counter, bend over and lift my maids dress, pull up my petticoat and pull down my black satin panty. Of course I curtsey and do as I am told, but I'm nervous wreak.

I am told to pull out my lube from my purse and begin to sensuously finger lube my sissy butt hole. I begin to work the lube up my butt hole and the men coach me on with lustful glee. Once I feel I cannot lube myself anymore I stick my ass out wanting to be penetrated by stiff male cock and I know to begin to beg for some hard core anal sex. My nerves are frazzled but I keep in the right fucking posture.

Sir Barry moves behind me and undoes his pants, pulls down his briefs and fondles his stiff cock as he leans over me and tells me how much he will enjoy fucking me tonight. I thank him for the honor. I then feel his hands grasp my butt cheeks and begin to forcefully massage them as I moan in fear and lust for what will soon happen to me. The other men are excited as they cheer on Sir Barry.

Barry says, "Chantel, Chantel, Chantel I am so hot to fuck your tight ass tonight."

I reply, "Ohh, sir, yes, sir please, oh please fuck me. I want this so bad, I beg you to fuck me silly."

Barry now begins to take his stiff 6+ inch cut cock and force it up my lubed butt hole, I whimper and sigh as he groans with his pushing thrusts to get through my sphincter. Once he gets inside he slowly works his cock up my rectum as I groan and moan with pain and lust. I am being hammered by a real man, something I know I am not. Hoots and hollers by the other men and Barry works up a good, firm fucking rhythm. His increasing groans turn me on as I know I am pleasing him. The sounds of my moans, sighs, ughs and panting mixed with Sir Barry's groans and hard pushing moans with his deep breathing is all so exciting. My sissy dick is stiff with lust from my ass being fucked.

The magic of this most lustful, butt fucking moment is what any and ever sissy faggot like me wants. It is just good hard sex for the men who do it as they hold no respect for such pathetic sissy sluts like I am. They just want to fuck like horny a****ls in trying to gain a sexual victory over us wanting sissy sluts and I so happily now want him to get his way.

The video of it all going on here with Sir Barry is going to be great. I look up and see the reflection of my sissy face in the bathroom mirror and see Barry pounding my backside with lust and desire to want to cum deep inside me. It is one of there most erotic images I have seen of self. I can't believe I so want this violation of my backside. I think, 'I love this feeling of pain and lust, this desire to be feminine and sissyish, to be taken away from my pathetic male life total of a sissy slut.'

Barry keeps pounding away as he groans and I moan. I can sense he is getting closer to his prize of true male ejaculation up inside my rectum. We work so well together now as we both know we want it. He wants to cum and I want his cum up my sissy bum.

Barry excitingly, "Ugh..Ohh. fuck... fuck yeah you li...little sissy bitch. Uhhh. ummm... fuck almost... almost there. Huh...uhhh..ummm. yeah...ohhh, gawd... yeah. yeah ahh." as he lets out a volley of his thick gooey cum, it shoots deep inside my sissy bum.

I reply, "Ohhh my gawd sir... feels ... so.. good. ahhh.. yes."

The men are all so horny waiting for their turns as Barry slows and then pulls his stiff shaft out from my back side and we both sight in relief. Barry tells me how good that fuck felt and I thank him for fucking me and letting me realize I am a damn sissy slut. I hold over the bathroom counter as he steps away and up next will be Sir Ralph followed by the other men and for the next half hour I am used like the slut I am and cum fills my ass as well as spills from such running down my thighs wetting my panty. I feel so cheap and dirty as the four men are spent and loved it all while they keep degrading me.

Barry says I can release my own lust by jerking myself of remaining bent over the counter as they watch. I feel horny and degraded but it only takes moments for my right hand to stroke me into cumming and I spill my sissy seed on to the concrete floor. I am allowed to tuck my sissy dick back in my panty as I am told to then drop to my knees and lean over the small pool of sissy cum on the concrete floor. I am ordered to lick my own splooge up and clean that floor as such. I do as I am told as gross as it may be to lick my sissy cum off a dirty concrete floor.

I am next told to stay on my knees and to be quiet, eyes looking down as the men talk about what will soon now happen to me. It seems that a major event in my new sissy life is about to happen. While we all wait to see what it will be the men talk about me and continue to degrade me while I remain silent, to take it all and only speak when spoken too. I am nervous as to what will next happen to me, I am sure it will be very domineering towards me.

Soon a car pulls into the rest area and the guys hear a person walking up. Mark glances outside to see a guy walking up the path and he notes that it's Gage. I'm told to stay on my knees, eyes down and to remain quiet.

Gage walks into the men's bathroom where he greets the four guys here and Sir Barry notes to him to look at sissy me and comments, "Well, that is sissy Chantel, quite the little sissy faggot and in her black maids dress, stockings, heels, wig and makeup."

Laughter is heard.

Gage is a 6'2" 210 lb. black man, in his mid 30's and fit as one can expect.

Gage speaks with his eyes wide open, "So this is the sissy faggot. She looks quite femme but cute in her frilly maids dress."

Ralph interjects, "Yep, she's quite the sissy bitch, the four of us just finished fucking her up her little sissy ass."

Gage says, "Really!? I bet she was nice and tight."

Barry says, "You want to see the results of our fucking?" he adds, "Chantel turn around, lift your dress and petticoat up and thrust your panty clad ass up for us to see."

Of course without much a word except a yes sir, I do as I'm told and my panty clad ass shows a wet crotch area of my satiny panty, it's from the four loads of cum shot inside my bum that has back flowed to wet my panty in the crotch area. It's so humiliating, Gage loves seeing this.

He says, "Yep, she looks like quite the bitch."

Barry says, "We think she could be what you are looking for, a good maid and a hot little slut. When Ralph and I saw your Craigslist ad. looking for a live in maid and slut we thought about Chantel. We are prepared to offer her to you for a fee."

Gage looking down at me says, "Hmm, could be a good maid and slut, she's cute and femmy enough." he adds with excitement, "I'll give ya all $200.00 for her."

Barry smirks and looks at Ralph and says, "No man, she can make that much for you as a street whore a few hours. We think she's easily worth $5000.00."

Gage laughs sarcastically, "$5000.00, shit how do I know she can be worked nightly as a cheap whore? How good of a God damn sissy maid will she be? Maybe she's useless and just a fucking pervert in a maids dress, stockings, heels, wig and makeup," he hums and adds, "Fuck, $500.00 is good I think."

I sit on my knees, eyes down and can't believe what I am hearing, men negotiating the sale of me into sissy service and prostitution, but I remain quiet."

Ralph chimes in, "Come on man, you are gonna make shit loads of cash from this cheap sissy whore, $3000.00." as he looks at Barry who nods yes.

Mark and Rick chime in, in unison, "Fuck look at her." then Rick says, "She will probably suck lots of cock and take loads of cum up her sissy ass for you."

Gage blurts out, "$1000.00 fuckin dollars."

Barry replies, "We are getting closer, $2500.00?"

There is silence and I am shaking in abject fear of what I am witnessing.

Gage says as he rubs his chin, "Ok, dammit I'll give you all $2000.00 for this fuckin sissy, I know I can make money off her and work her hard as a sissy maid too."

Barry, Ralph, Mark and Rick huddle and whisper among themselves. I want to speak up in my defense but am scared to for now.

Barry then replies, "Ok, $2000.00 but the four of us get Chantel to give us free head or lets us fuck her any night she's on there streets for as long as she is your sissy bitch.

Gage says, "I'm ok with that, $2000.00 plus you four get fucking privileges."

I now interject, "Excuse me, um what the Hell? I'm not going to be sold into any form of sissy slavery and prostitution," I am angry and add, "God dammit just because I dress up as such and even give head as well have dudes fuck me in a public men's bathroom does not mean I'm going to become some guys sex slave, slut and maid."

Gage in anger turns to me and says, "Fuck you bitch, not only are you going to become my live in sissy maid but I will become your black pimp master. You know you fuckin want it, all you fuckin sissy faggots want this."

I'm angry and yell out, "No fucking way! I may play this shit, even fantasize about it, but I'm not going to become your sissy slave!"

Gage stands before me, his eyes look down and pierce mine, I am angry but shaking on my knees as I look up at him in sissy defiance. When out of the blue Gage's right hand in a firm open manner slaps the left side of my face in full manly force, knocking me off balance and to the floor hitting my right shoulder as I cry out in pain and curse a him and the other men.

Gage then kicks me on my backside as I whimper in pain but still lip off in defiance, telling him and the others to fuck off and leave me alone. Laughter explodes as these men see the breaking of me by a strong 6'2" black man.

Gage yells, "Get up, get up on your fuckin knees you faggot sissy!"

I get up on my knees and remain quiet as I rub the pain from my face.

He adds, "You are going to become my live in sissy maid and slut, it will fuckin happen and you fuckin want it!"

I in near tears reply, "No, please leave me alone, I just want too go home now."

He then asks two of the guys to help me up to my feet, Barry and Mark now grab me by each arm and pick me up as I now stand before Gage in total fear. I see his angst, anger and desire to break my sissy will, what happens next is completely good at breaking me. Gage takes his right knee and thrusts it up into my crotch, nailing my sissy balls and dick, I cry out in pain and he tells the guys to let me fall to my knees, which I do. I crumple into a ball on the bathroom floor writhing in agony. The ohhs and ahhs of the guys in the room falls now to silence as all watch me in agony. I whimper out a near silence, "Please no."

Gage gets down and says to me, "Do you want more of this Chantel?"

I cry out in pain, "No sir."

He adds, " You going to cooperate? You going to accept your new fate?"

I look at him and say, "Yes."

Gage says, "Yes, what?"

I know he has won as I say, "Yes, Master."

Master Gage now calmly pets my head, running his right hand through my long wispy wig. He tells me he does not want to be a mean abusive Master, he wants to help me live out my sissy fantasy as he gets the sissy maid and slut he fantasizes over. The head games he will play over me will have me accept my new fate. I now know I had better cooperate, maybe he will grow tired of me and let me go soon enough.

But now in all this excitement I find Master Gage is ready for claiming a prize, it looks as if he wants a blow job from me as I am now back on my knees and I see him gesture for me to undo his pants. Of course I comply. I with shaking hands begin to undo his belt as he tells me to settle down, he wont hurt me, but just wants me to suck him off. He asks to have a video made and two guys pull out their cell phones to begin making video.

I now pull his pants down and they fall to his ankles. I see his boxers and see a growing bulge. I am told to ease his boxers down and as I do out flops Master Gage's, big black cock. Oh my God it must be 8+ inch long and shit 2+ inches thick, and well cut. My eyes go wide as Gage takes his left hand and grasps my chin forcing me to look up at him. His right hand fondles his big black cock. I am very nervous as this cock is massive for my rookie sissy mouth. I also think how bad it will be when he does finally fuck me with it.

Gage with a smile says, "Chantel, girl look at me, ask me permission."

I sheepishly ask, "Master, may... may I please... umm have the privilege to suck your big beautiful cock?"

Gage asks, "You want to suck my cock sissy? You like it girl?"

I look up at him and say, "Um.. yes Master, please I want to suck your beautiful cock so bad. I want to taste you manly cum."

Gage says, "Go ahead, you are a sissy bitch, a cock whore, suck it, suck me off Chantel."

I lean forward, grab his cock and balls with both of my lily white sissy hands as I now move forward and open my sissy mouth. The massive girth parts my wet lipstick covers lips as it slides inside my mouth and over my wet tongue. I can't believe what I am doing, sucking a big black cock to a man who is now going to be my Master. As Master Gage moans at this feeling I take it slow and work up saliva. I am taking it all in as I work this massive cock inside my sissy mouth. The other guys love watching this and cheer Master Gage on.

Soon we are working together in a rhythm. His cock feels warm and leathery over my tongue and through my lips. I am moaning in growing sissy lust as I am taking such a big black cock from my new owner, Master. Master Gage is getting more and more worked up at the feeling of my sissy mouth working over his massive cock and at the sight of a pathetic white sissy girl doing what she will do best, sucking cock.

As we work our mutual lustful dance of my sissy head bobbing over his cock he in growing desire to eventually cum well its so hot and erotic. I'm thinking, 'Jeez I did not see me sucking big black cock and that of a black pimp Master tonight.' But work it I do and with my own growing lust. My own sissy dick is rock hard in my panty and the other men see this and cheer me on for my proving I enjoy this. My head is filled with lust and shame but I have a job to do, to suck my new Master's cock until he cuts.

Minutes pass by and I sense Master Gage is getting close to cumming, I sense him working a wad of hot jizz through his cock and I now want him to cum in my mouth. I work hard to get him to cum. We moan and gown with lust together and I now feel Master Gage's firm hands grasp the back of my sissy head as he begins to control, and thrust until he groans and shoots out a huge, thick wad of his hot sperm filed jizz inside my sissy mouth. I cannot believe the gush of warm goo fill my mouth as he now slows and then pulls out, his cock flops before my face. I look up at him, smile to thank him for the honor as I then show him I swallowed his jizz. He smiles and pets my head telling me I'm a good sissy girl. I feel pride and joy for making my new Master happy. I tuck his cock back in his boxers, pull up and then do up his pants and then remain on my sissy knees.

Talk moves to how we all will drive out to Master Gage's home and he will get $2000.00 to give Barry and Ralph, have me draft out and print off a bill of sale to which I will begin my transition into slavery. I'm so scared but so excited too.to me so soon.

I cannot believe at what is happening to me here. Master named Gage is about to purchase me and place me into slavery as his sissy maid and sissy slut. I am near in panic, I want to run away, get into my car and drive for the safety of my home. But I know this will not happen.

We all get ready to drive to Gage's home, I give my car keys to Rick who has agreed to drive my car as I will be driven to Gage's home in Master Gage's car. As we all walk out to the parked cars I am told to get into the passenger side of Gage's Cadillac CTS. I think, 'Hmm, he must be doing well to drive such a pricey car.' I get in the passenger side and close the door, my nerves are all a fluster. Gage walks around to the driver's side and gets in too. The interior light is on and before he starts up the car his right hand falls onto my thigh just under my dress and petticoat. He rubs the sexy lace tops of my stockings and fingers one of my garter's clasps.

He says, 'Hmm, feels good girl, love your stocking tops. It's gonna be great to make you my live in sissy maid and a thrill to pimp you out."

I meekly reply, "I...I am nervous sir.. err Master, please, please don't hurt me."

Gage then runs his fingers through my wig hair and tells me if I'm a good girl, it will be better, if I a bad girl, life will be hard. We now get going and I am quiet as he is too. A few words are spoken in the 10 minute drive to his home. Once there and parked I get out, Gage does too and the other men are parked as well. We all walk into Master Gage's house and I am introduced to where I shall soon move in, live, work and pimped out from. I am lost in fear and worry but I say nothing.

I am instructed to sit in a chair and use a computer to draft up a bill of sale, then once done print it out for all involved to sign. This will guarantee $2000.00 payment and fucking/sucking privileges in perpetuity for Barry, Ralph, Rick and Mark. Once this was all done I was ordered to make drinks for the men so they can celebrate my sale.

Talk moves to how my enslavement will go about. It seems that I will be swiftly moved into Master Gage's house as his full time life in sissy maid and from the home he will pimp me out nightly as a cheap tranny slut. I could not help but let out I have a Master/Slave contract on a computer of mine at home that I have worked on as a fantasy contract for years. It will govern rules of my enslavement to Master Gage.

Well this fact makes the men excited to read it and they decide that we shall pick up this contract (a PDF file) to be downloaded and subsequently printed out and signed, thus enslaving me by my own desires to Master Gage.

But first, my new Master believes I need to be locked in chastity as sissies like me like to touch and play with our sissy dicks. He should control such play and masturbation. Master Gage notes of a 24 hour sex shop we all can go to and find me a chastity device and maybe some corporal punishment tools. All the men are up for this. I'm obviously scared and worried buy liker a good sissy I comply.

Soon Master and myself in his Cadillac and the other men in a car follow to get us to this all night sex shop. Once there we all enter and my sissy self in my black maids dress, black sheer stockings, 5 inch black suede pumps, makeup up an wispy blonde and auburn wig is the focus of the two ladies who are working in the shop.

One lady smiles and says, "Well, well, well, what do we have here? Looks like a prissy sissy all cute in her back maids dress, hose and heels."

Her co-workers chimes in, "Yum, lovely, cute lil sissy maid."

Master Gage says, "Ladies yes, this is my sissy maid Chantel, Chantel mind your manners and greet these ladies."

I respond, "Yes Master." as I curtsey and say, " Good evening ladies, I'm sissy Chantel, it's a pleasure to meet you."

The first lady asks, "So what bring you gents by with cute sissy girl?"

Master Gage responds, "Well Chantel is my new hire as a sissy maid, she will be living with me full-time as a sissy maid and slut, but like all too many sissies she can't seem to keep her sissy hands off her sissy junk, her sissy dick. I have to control it and use masturbation as reward for a good sissy maid and slut."

First lady says, "Well guys I'm Jada and this is Chrissy, we can help you find a good chastity device for your little sissy maid."

Jada and Chrissy walk all of us down to a part of the counter where male chastity devices are and quickly pulls out a CB3000 which is their most popular chastity device. My eyes view it in shock knowing with my sissy dick locked inside it I will not be able to joyfully play with myself. My new Master can hold it over me and keep me inline to be a good sissy slave.

Gage says, "Looks good we will take it, can Chantel put it on right here, right now?"

Chrissy replies, "No problem hun, your sissy girl can plop this on pretty easily if you like."

I speak up, "Um, ahh what if I have a hard on? I mean my sissy dick is stiff inside my panty."

Jada says, "Well it needs to be fitted if you are rather soft, we have to rid you of your sissy hard on, may I suggest letting her masturbate one last time before you lock her sissy junk up."

With all the guys watching, Master says, "Ok, sounds good, can she just stand here in front of all of us and pull her sissy dick until she lets go a volley of sissy cum?

Jada and Chrissy giggle and Jada says, "Sure we can all watch her play with herself in her maids dress, stockings, heels, wig and makeup, should be fun."

I'm red in the face with embarrassment as I am instructed to lift my dress, petticoat and pull down my panty to reveal my stiff sissy cock. I am to stand before all here and jerk myself off in all humiliation of my new sissy fate. I begin to fondle my sissy dick. I am humiliated but also turned on as I pull on my sissy dick.

Minutes pass by and I grow ever more sexually stimulated as video of this is going on and all the people watch and laugh at me and my plight. I can sense the inevitable but so wanted ejaculation is about to happen. I ask where shall I cum? I am told to just let it all fall to the floor. I am horny with humiliated lust and desire to cum and in a hot moment and some hard pulling of my sissy dick, I grunt out a big moan as my sissy dick begins to shoot out a few volleys of sissy cum. Each splurge falls to the floor between my high heeled feet as I come down from this high and crash. I feel so pathetic and tired. I then tuck my sissy dick back into my panty, let my petticoat and dress fall into place. Master orders me to give thanks and a curtsey to all. I feel like crap and only wish I was at home which is not going to happen right now.

Jada smirks and asks, "Um, she really needs to clean her sissy mess up. May I suggest she drop to her knees and lick it up off the floor."

Of course Master Gage agrees and says, "Chantel mind your manners, on your knees, lean over and lick up your pathetic sissy cum."

Laughter is heard I say, "Yes Master." and get on my sissy knees, bend over the splooge on the linoleum and take my tongue to slurp up my sissy cum. Once done I put on my chastity device and know it's locked and Master holds both keys.

With that done talk move on to devices that can be used for corporal punishment. The ladies giggle as they walk us to where good punishment devices are and Chrissy picks out a good about 24 inch long device with a 12 inch long x 4 inch wide stiff leather paddle. She says this is their most popular paddling device as it will sting bad but not cut flesh, notably soft sissy buttocks. Master now holds it and likes it, it feels good in hand, he passes it around to the other guys. They all swat it around in the air as they look and smile at me. I am very scared but say nothing. Master Gage asks if he can try it out on me here. Of course it's ok and I am soon bent over there counter and my sissy buttocks exposed. Master tells me to thank him after each swat and to ask for another. I say, "Yes Master."

I am in fear of the pain I am about to endure and soon I hear the swoosh of the paddle and feel the stinging pain as it strikes my lily white buttocks.

I yelp out a cry and say, "Thank you Master, may I please have another?"

Laughter abounds by all watching this as Master gives my buttocks another swat and it stings more. This goes on three more times before Master stops and then lightly rubs my pink buttocks with his right hand. I am kept bent over as Jada pulls out another device. It's an electric cattle prod. It delivers high voltage but safely low amperage shocks where ever the prods tips touch. I quiver in fear as Jada says where such a prod may work well in disciplining a slave. It looks as if butt cheeks work good, or pull open the cheeks and touch the butt hole, or a good one zap the metal cage of the chastity device and shock a sissy's genitals. Of course Master tries it in all three places and I freak out in pain from the shocks, I am near delirious in shock and a pain as I fall to my knees and beg for no more.

Master stops and says, "We will take it too."

Jada asks, "How about bondage gear? Surely a sissy like Chantel will need some added discipline and bondage shall help. Let us show you a few things."

Master Gage replies, "Ok, sounds good." as we all follow the ladies and they take us to a display of a built bondage bench. It's all black with nice black vinyl padding. It looks as if a sissy like me will mount on it in doggy position, my feet will be restrained and so too my hands. It can be set up to allow my upper body to rest on a big padded area. Jada explains how this bench will allow a Master to bondage fuck a sissy up her ass and down her throat. Or can be used for a good dose of ass paddling and such. I am quite scared of this bench, but Master likes it a lot.

Chrissy brings over a contraption that is said to be a fucking machine. She explains how one puts a dildo on the end of this rod like piston. Insert the dildo up a sissy's butthole and then turn on the machine. It can be speed controlled for slow to fast piston like movements. A great way to break in a tight sissy's ass. Master loves it.

Jada notes another cool bondage device and we all follow her to it. What I see is a vertical cage that opens up and can have a sissy like me step inside. The cage can be closed and its designed to be adjustable to make it more restraining. She says how such a tight restraint, vertical bondage cage can be good for a sissy girl like me as will be forced to stand in one position with my high heels on.

Gage asks for the costs, Jada tells him the bondage bench is $1495.00, the fucking machine is $495.00 and the vertical bondage cage is $995.00. which totals $2985.00 plus tax. She says all three can be delivered in about a week to ten days. Master Gage says we will buy it all along with the paddle, cattle prod and my CB3000.

As we all move to the sales counter Jada gets a grand total, it comes to $3460.00. Master Gage tells me to give her my credit card. I am shocked, that is a lot of money.

I say, "Master that is a lot of money, I do not want to pay that much."

Master Gage angrily says, "Shut up faggot and give Jada your credit card. I own you now and you will pay for all this gear."

I know to do as I am told and hand Jada my credit card as Jada smiles at me and says, " Thanks hun."

Once the sale is complete we take the items we can home with us and wait for the major items to be shipped to Master's address in a week or so.

The four guys who sold me to Master Gage now leave with their $2000.00 and I am taken back to Master Gage's house.

Once back at Master's house I am brought to the living room and told to sit on my knees and remain quiet, of course I do as I am told. Master Gage gets on his phone and calls somebody. It sounds as if it's one of his homeboy, friends.

Gage says, "Hey man, you wanna come over to my pad? I've got a surprise for you, you are gonna love it. Yep, just come over ok, yeah bye." as he hangs up.

Looking at me he smiles and says, "You look worried bitch, you got nothin to worry about sissy girl, just as long as yo know and stay in you place."

I reply, "Yes Master."

He adds, "You are gonna get use to being my sissy slave, a maid and a slut, I'll make sure of it girl. You will be thanking me for helping you find your dream to come true."

I reply, "Yes Master."

Master Gage has me download my PDF file of my Master/Slave contract that I have made. I do as I'm told and sit quietly back on my knees as he reads it to himself. He smirks, giggles and laughs at how detailed of a Master/slave lifestyle I want. He notes I am sold on my sissy name to agree to legally change my name to it. That name will be Chantel LaFemme Swallows. He loves how I will no longer wear male clothes, surrender all of my assets and money to him and agree to a slut lifestyle and a very basic sissy diet. In short he is 100% on board with using myself written Master/slave contract.

A few minutes pass by and then the doorbell rings and Master gets up from his chair to answer it. I guess I'm going too meet a buddy of his, this will be interesting as I sit still on my sissy knees. Moments later a home boy of his sees me and bursts out laughing and asks why the fuck I am to Master Gage.

Master Gage says, "This is my new sissy maid and slut, her name is Chantel and she will be living with me."

His buddy replies, "No shit man, this for real?"

Master Gage answers, "Yep, Chantel will be my live in sissy slave, for as long as I feel she can serve me. I want you to be the witness of the Master / slave contract that Chantel has drafted and wants to sign with me," Gage adds, "Chantel this is Martin, Master Martin to you."

I reply, "Yes Master, nice to meet you Master Martin."

Martin can't believe what is happening. As I am now to sig the Master/slave contract with Master Gage and Master Martin as a witness. A video camera is set up to show I am cooperating with the signing. As it is all completed I now know I am to become a true full time live in sissy slave, who will serve her Master as his sissy maid and sissy slut. I am terrified at tsk but a big part off me wants it.

Master now wishes to consummate this new contract by having me be fucked up my sissy butt hole with his 8+ inch cut black cock, then once he is done have Master Martin fuck me up my butt hole wit his cock and he too is at least 8 inches long and close to 2 inches thick and cut. Master orders me to kneel on all fours on his coffee table. He then has me lift up my maids dress and frilly white petticoat. I am to take the lube out from my purse, pull down my panty and begin to finger lube my sissy butt hole. Of course I do exactly as I am told.

A minute or so later I am sure I have lubed my butt hole up well, well as good as I can knowing big black cock is about to take my lily white sissy ass. Video of all the runs for posterity and soon Master Gage stands before me. He undoes his pants and pulls his boxers down, freeing up his growing black cock to it full 8+ inch length. My eyes go wide with fear and lust. Master Gage takes a moment to dick slap my sissy face with his massive cock and the two of them laugh at me.

As Master Gage moves behind me he says, "Fuck, I'm gonna enjoy this, fucking a tight, lily white sissy's ass. She is so cute in her maids outfit, Chantel ask for permission."

I on all fours and unable to see Master as he is behind me, I just look forward and do see Master Martin off too the right front side and ask, "Master, please fuck me... Oh please, please, please take me... I so want to feel your huge manhood up my sissy butt hole., God I want you too fuck me silly until you cum inside me."

Master now takes his firm hands and knees my butt cheeks working up his desire to fuck me. Soon he is spreading my butt cheeks to reveal my sissy butt hole, he figures it a bit to feel all the lube as he laughs at me. But now he takes his big black cock and slowly begins to work it up my sphincter and it hurts as he tries to push his 8+ inches of black manhood up my sissy butt hole. I whimper a bit and cry and he grunts and thrusts. Soon he gets up inside me and his firm hands hold onto my hips to keep control over me. He goes slowly to work his huge black cock into a good fucking rhythm. It becomes for me a mind fuck too as my prostrate feels his shaft and I sense pain and joy all knowing I am his owned sissy bitch.

Master Martin chimes in, "Man look good, fuck that faggy white sissy, I can see that she wants it, she loves it, nail her her sissy ass man."

I glance at Master Martin and say, "Uhh,, ohhh yes, yes, Master... Master Martin, is right, Oh God fuck me Master... Ohhhhh .. uhhh ahhh,, it feels so go...good." as I keep panting with growing sissy lust.

Master Gage excitedly says, "Fuck yeah, you are so.. uhhh...yeahhh. tight, fuck I love your... ahhh... lily white ass. I love. ahhh.. yeah, I love owning you Chantel... ohhh, fuck you are my bitch now." as he pounds me harder and harder. He is going more a****listic with sexual lust.

We do work well together as I take his big black cock up my sissy ass and he feels I am rocking on my hands and knees in mutual movement. We both are in a lustful frenzy of Master and sissy slut sex.

Master Gage works hard to get to orgasm, minutes pass and I can sense he is ready to let go. I want his cum inside me, I want him to know he owns me. I beg him to take me, to cum inside me and I feel it drives him horny with desire. Master Martin cheers us on too and I sense soon Master Gage is about to let go.

I now hear a huge grunt and a deep thrust as he now cums a thick hot wad of his sperm filled jazz deep up my rectum. I was not locked in chastity my sissy dick would be hard and close to a mutual ejaculation, but my lust is not require for Master Gage's lust. Soon Gage slows and pants a bug sigh as he pulls out from my sissy ass. He leans forward and tells me I am a good little sissy bitch. I thank him and he moves away.

Before I know it Master Martin is behind me his pants drop and his briefs pulled down. He too has big back 8 inch cock and he grasps my ass and begins pushing his cock up my wet cum filled butt hole.

He says with excitement, "I'm gonna love fucking your cum filed hole, FUCK! it turns me on."

I say, "Oh... ohhhhh yes, I love it, ohh feels so...so fucking good Master."

We get into a great fucker/fuckee rhythm and we are both hot for this raw hard core butt fucking sex. I know I'm going to love it and love the sex of my new sissy life. Assured I am to see my once male life pathetically pass away I know I will become a good sissy maid and slut.

The ass pounding I am getting from Master Martin is fun and such a turn on, I can sense he is working up to his soon to achieve prize of cumming up my ass too. We work together and soon I sense his grunt and lustful plunge up my ass as he shoots out his wad of glorious man juice, cum, cum that any sissy faggot like me lusts for and wants.

As Martin slows and pulls out to do up his pants I am told to stay on all fours, my ass up in there air so that all the cum will flow deep up my rectum. Minutes pass as the two men talk about me and my new slave life, how I will be pimped out on the town's tranny stroll and how I will become the best sissy maid possible too.

Master now allows me up and onto my high heeled feet to fix my panty, petticoat and dress. I sense cum back flowing and begging to wet my panty's crotch area. I feel embarrassed but know this is my life now.

Master tells me that two days from now about 10:00am he and Martin all come to my place to begin my transition into slavery. I am to be in a black maids dress, heels, hose or stockings, wig and make up. I am to be pretty and sissy for him. He dismisses me after I give them both a sissy curtsey and I am allowed to get in my car and drive home.

The drive home is mixed emotions. I am excited but angry too. What is left of the man in me is pissed off and makes me feel sick. The femme sissy in me thinks about my new Master. I am so confused and lost track of time in my drive home. Parked I get out of my car and strut in my heels inside my home. I sigh and begin too cry. I am lost and do not know what to do. I quickly get out of my maids outfit, stockings, garter, panty and bra. Take off my wig and begin to run a shower as I begin to wash off my makeup. While in the shower with warm water running I crumple up and cry as I think, 'FUCK WHAT THE FUCK IS MY PROBLEM!?! How did I get here? How do I let a man enslave me? I need to figure a way out of this.'

I wash up and then dry off. I sit wrapped a towel on my bed, I loo at my heels worn tonight, my two black stockings on my bed with garters, bra and panty. Hanging in my own closet are my maids dresses, all eight, four in black, four in pink and all my slut wear. I begin to feel my chastity device and am angry at this man has the keys and now keeps me locked up. I am growing lustful to want to jerk off but I can't due to my chastity device.

I take the towel off, put the bra and panty back on, pick out a black satiny full slip and then crawl to bed. I am tired, confused and my ass hurts. I drift to sleep and soon a new tomorrow will come.

The drive home is mixed emotions. I am excited but angry too. What is left of the man in me is pissed off and makes me feel sick. The femme sissy in me thinks about my new Master. I am so confused and lost track of time in my drive home. Parked I get out of my car and strut in my heels inside my home. I sigh and begin too cry. I am lost and do not know what to do. I quickly get out of my maids outfit, stockings, garter, panty and bra. Take off my wig and begin to run a shower as I begin to wash off my makeup. While in the shower with warm water running I crumple up and cry as I think, 'FUCK WHAT THE FUCK IS MY PROBLEM!?! How did I get here? How do I let a man enslave me? I need to figure a way out of this.'

I wash up and then dry off. I sit wrapped a towel on my bed, I loo at my heels worn tonight, my two black stockings on my bed with garters, bra and panty. Hanging in my own closet are my maids dresses, all eight, four in black, four in pink and all my slut wear. I begin to feel my chastity device and am angry at this man has the keys and now keeps me locked up. I am growing lustful to want to jerk off but I can't due to my chastity device.

I take the towel off, put the bra and panty back on, pick out a black satiny full slip and then crawl to bed. I am tired, confused and my ass hurts. I drift to sleep and soon a new tomorrow will come.


Two days have passed by, it's Thursday morning. Today Master Gage and Master Martin are to arrive by 10:00am. I awake by 8:00am and my stomach is turning. I get up sit on the edge of my bed wearing my sleeping lingerie today it's a white satin full slip, white lace bra and satiny panty. I think for a minute or two and decide I am not going do as Master Gage says. I am going to be a man, going to respectfully but assuredly show Master Gage that it's not going happen, my slavery to him that is. I'm going to have to get him to give me the keys to the chastity device and tell him I'm going cancel out the bondage gear sale on my credit card.

I shower up and dress in drab as I wait for Master's Gage and Martin to come. I am not too hungry as I'm nervous so I just drank some coffee and clock watch. I worry if this is going to go ok or not but I have to be a man.

Tick, tick, tick the clock ticks. About 10:05am I see Master Gage's Cadillac CTS park in my driveway. I am frazzled as I wait to meet the men at the door.

I hear the door bell ring, swallow hard and walk to open the door. As it opens I see Master Gage and Master Martin stare at me.

Gage says, "What the fuck! Were you not to be in a black maids dress, hose, heels, wig and makeup?"

I stammer but say, "Um... well, I decided that I am not going to become yours or any bodies sissy slave. I'm a man and I plan to live like one. I'm a crossdresser, fantasize about sissy stuff and now even have sex as a sissy with guys but I am not going to ditch my set male life," I am so nervous as I add, "Sorry Gage but I want the keys to my chastity device and I'm going to cancel the credit card sale for the bondage gear."

Master Gage in growing anger pushes his way into my home as I back away and he and Martin stand before me, Gage says, "Oh fuck you, you faggot, you are my sissy slave, you will live as my sissy maid and slut."

I interject, "No, you can't make me your fucking slave."

Master Gage angrily says, "You are not being made to be my sissy maid and slut, YOU SILLY FAGGOT! You want to become and will become my sissy slave."

I remain steadfast and stand up to him denying this slavery, Master Gage begins to push me back and around as his anger grows. I implore him to stop pushing me around in my home. Gage and Martin just laugh, "You ain't gonna live in this home much longer, your fucking new place will be as my sissy maid and slut in my home." He then viciously open slaps the left side of my face with his right hand and swears at me. I cry in pain an tell him to stop, I do not want to fight him, just leave me alone.

Gage says, "Tell you what you faggot, you think you are a man, are you man enough to fight me?"

I reply, "Fight, I do not want to fight you I just want to be left alone."

Gage angrily says, "That ain't gonna happen, you have to prove you are man, and fight me, you don't even have to win but just show us you are man."

I reply in stress, "Please I do not want to fight, I should not have to either."

Gage is steamed as he calls me a sissy faggot who needs to be in dress and heels. He then gives me a good punch in my face on my nose and I drop like a rock as I hold my nose with my right hand and tell him to fuck off! I sense some blood from my nose as he slaps the left side and then the right side of my head as I'm in delirium and fear to the beating it looks I may have to take.

On my knees he calls me out, "Come on you faggot! You say you are a man, fucking fight back you pathetic sissy!"

I implore him, "Please just leave me alone, let me go, dammit."

Gage delivers two my open slaps to my face and I am devastated to the point of tears and beg him to stop hitting me.

Master Gage replies, "You gonna cooperate now or do I have to beat the shit out of you faggot!?!"

Martin interjects, "This sissy is fuckin stupid, she know she is a sissy and wants to be a slave."

I now beg him to stop and give in, I tell him I am his sissy slave, his sissy bitch and maid, I will cooperate, and beg him to stop beating me. Master Gage lets up and tells me to get my queer ass to the bedroom, strip off my male clothes, go to the bathroom and give myself an enema, a shower, do my make up and dress up in my black maids dress. While I do this he and Martin will go through my belongings, to select what they will take, what we will sell and or give away. I comply and he sees me out to my bedroom to strip nude.

I sit on my bed all naked and knowing I must move on, give myself an enema, then shower and do my makeup. This will see me move to putting on my maids outfit, I will be wearing a black lace bra, black satin panty, a pair of white tights and my black satin and white lace maids dress over a frilly white petticoat. I will step into a pair of black velvet 5 inch spike heel pumps with cute ankle straps.

The enema, shower, makeup and dress up takes about an hour. It's now about 11:15am as I am dressed and ready to make my appearance to my new Masters. I know this commits me to my new sissy lifestyle. I walk out and to the living room. As I enter the Masters like what they see and I give them a big sissy curtsey.

"I hope Masters like what they see in their sissy girl."

Master Gage, "You look great girl, nice little sissy maid."

Master Gage has me make and serve both of them coffee as they begin to tell me of the things that I have they will take as their own and how we will dispose of other things they do not want and I a no longer need. I curtsey with a "Yes Master."

Master Gage next says, "Since my sissy seems to have issues with her faggotry and sissy expectations I have determined that starting today you shall only wear sissy maids outfits and sissy slut outfits," he adds, "You will get some garbage bags and gather up all you male attire and items and we will be donating them to charity today, do you understand Chantel?"

I gulp and explain, "But Master I still need to wear male clothes, I have yet to give my notice to my current employer and they will want me too come to work dressed in my normal male attire."

Master Gage says, "I don't give fuck you sissy, I made my mind up and you are going to transition today. In fact you will bring all your femme and sissy clothes over to my place and you will begin to serve as such through your transition. You do not have to live here in your current place as we dispose of your current home. Life as you have lived it is over for you girl, you will now live 24/7/365 as my sissy maid and slut."

I beg him, "Please why can't we transition normally, why must I humiliate myself beginning today and to my employer, please let me not have to do this."

Master Gage says, "I don't give shit, you are going to live from now on as my sissy slave. Stop this whining to I will beat the shit out of you."

I know I'm defeated, I curtsey and accept my plight. Master has me come to him and drop to my knees in submission and pull out his big beautiful black cock and service it with my mouth for a brunch like treat. I do as I'm told and give him a beautiful blowjob resulting with a good mouthful of his cum and he has a nice smile. I next do the same and service Master Martin's cock and he gets off well too with a nice brunch like treat for me. I feel like such a sissy bitch.

I now gather up my male clothes and we are off to the thrift store. Minutes pass by and we pull into the thrift store parking lot, me in my black maids dress, white tights and high heels will be a sight as I bring garbage bags full of male clothes to donate. I am ordered out of Master's car and gather up the bags of clothes. I grab two bags and begin to walk towards the store my high heels clicking away. As I step in the shop people and staff begin to notice me, I mean I'm dressed as a sissy maid, my face is flush as I sheepishly walk up to a counter and tell the ladies I am donating male clothes as I no longer will wear them because I'm a a sissy girl and a sissy maid. The ladies smile and comment at how cute I look and I bet I'd be a fine sissy maid. They jokingly ask if I can come to clean their houses? To who I politely smile and say my Master decides my maid duties.

I go back to the car and bring two more bags in and the ladies compliment me on how well I walk in my high heels, I curtsey and thank them for the compliment. It seems they enjoy seeing such a feminine sissy maid. It turns out to be not so bad for me to humiliate myself as a sissy made here.

Back in Master's car we drive off to the mall as I am to humiliate myself walking in the mall and to a salon to see if I can be fit in for an ear piercing and then to put on some big hoop earrings Master hands me and to also get a French manicure to feminize my nails. This walk through the mall and to the salon in my maids dress, tights and heels is so humiliating but I do love it too. The ladies at the salon do have fun with me and swoon all over sissy me as they have fun with my ear piercing and my manicure. They talk all about my sissy maid look and effeminate style. I tell them I am a live in maid to a master and I will also become a street walk sissy slut on the town's tranny stroll. The gals soak it up and get a kick out of what kind of femme sissy I am.

They joke about how must I must love cock, to which I tell them I am a happy cock sucking sissy and I service big black cock of my black Masters. For all the ladies it's almost surreal but it is my new life. I actually get over my nerves and enjoy my time at the salon. I call Master Gage and tell him I will be finished soon and he tells me to walk back out to there same part of the parking lot he dropped me off to soon see his Cadillac waiting for me.

Once I finish up, my new hoop earrings in my pierced ears, look at my French manicure, noting I must be careful with my pantyhose, tights and stockings now as I do not want my nails to put any runs in them. The ladies send me off nicely wishing me good luck in my new sissy life as I curtsey and the them, the humiliation is strong but I endure as I must from now on.

Getting back in Master's car I show the my earrings and my manicure the men say it all suits faggy, sissy me. We now drive to my employer's office where I will give them my notice and explain I must be able to work the next two weeks in a maid dress, hose, heels, wig and makeup as I no longer wear male clothes. I doubt they will accept this but I must do it this way. If they can't accept me coming to work for the next two weeks in maids dress and heels the will have to let me go A.S.A.P. I tell Masters that I don't know if they will let me come to work in a maids dress, but I doubt it. Masters are ok with this as the sooner take me on and pimp me out A.S.A.P. without having to wait of me to put in two weeks at my current employer. As we get closer to the office, my nerves are a frazzle, this will be fucking humiliating.

As we park in the parking lot of my workplace office I want to beg Master to not have me do this, but I know it's futile, sissy maid and sissy slut life is my way now. I know I must get use to dressing 24/7 and out in public as such. I am ordered out of Master's car and once I step out I curtsey as they send me on my way laughing at me.

Click, clock, click, clock my heels make as each step brings me closer to the office entrance. I am breathing with fear as I open the door and walk through the foyer to the front desk secretary, her name is Gloria and she looks up at me and her eyes go wide open as her jaw opens with silent WHAT THE FUCK?

I curtsey and say, "Good afternoon G...Gloria, um thi... this is Phil. I'm coming here to...too just give you all my two weeks notice."

Gloria smiles but is still shocked as she says, "Phil, what the Hell, she giggles as she asks why I am dressed as a maid?"

I sheepishly says, "Um... I have finally found the job ...err career I have wanted most of my life... th...that is that of a maid, in... in my case a sissy maid. This is why I am dressed like this."

Gloria says, "Well you look cute but why tell or show us what you want to do for future work? Why give you notice dressed like that?"

I reply with a sheepish smile, "Um... my employer, err my Master has had me dispose of my male clothes, I only wear feminine clothes like my maids dresses, hose, tights or stockings with high heels and makeup with wig." I add in full display of my look, "I have to note that I will be coming to work over the next two weeks in a maids dress, black like the one I am wearing or pink with appropriate hose, heels, wig and makeup."

Gloria smiles as she says, "Well I have to find out from the boss if that will be acceptable, you can have seat as I check for you."

I curtsey and move to take a seat, Gloria giggles and walks to the boss's office down the hall. I am so flush with humiliation. About a minute or two pass by and I see Gloria walk back but the Boss Michael is behind her, I think, 'Shit is this going to be humiliating.'

They re-enter the front room and Michael asks, "What's going on Phil? Why are you here dressed like that? Is this some kind of joke?"

I stand up and curtsey as say, "No sir, no joke, I'm here dressed like this as I am now going to live and work as a sissy maid, I only have feminine and sissy clothes to wear, but... but I am just giving you my two weeks notice."

Gloria replies, "Phil says he has to come to work in a maids dress for his two weeks notice."

Michael looks at me and hums, he has to be careful with how he responds but says, "I'm sorry Phil, we can't have you working your last two weeks dressed as a sissy maid, you will disrupt the other employees. If you can come dressed in regular male clothes that will be ok."

I reply, "Um sir I... I can't... I no longer have nor wear male clothes, my new employer well my Master has me only in maids and feminine clothes."

Gloria adds, "Well, maybe we can have Phil work with the secretaries, I'm sure the girls will be ok with this."

Michael pauses and says, "No, I'm sorry we can't have Phil work for us dressed like this."

I interject, "Um... I... know and I accept what you say, if I may my new name is umm.. actually Chantel. I'd really prefer being called Chantel as Phil is a part of my past and Chantel is my present and future."

Gloria sees Michael is a bit embarrassed as she says, "That is a cute name, you look like a Chantel."

I curtsey and say, "Thank you ma'am."

Michael pipes in, "Well tell you what will do for you Phil... err sorry Chantel. I'll give you two weeks severance and you can just leave here today, I want to make it a clean break ok?"

I curtsey and say, "Thank you sir, that will be fine."

Michael asks, "Gloria, can you get Jennifer in payroll too prepare the papers and two weeks severance pay?"

Gloria replies, "No problem. We will take care of Chantel."

Michael turns to me extends his hand and says as we shake hands, "It's too bad, hate to lose you but if this is what you want to do with your life Ph... Chantel, well good luck to you."

I reply, "Thank you sir."

Michael walks away, Gloria says for me to be seated as she goes to Jennifer in Payroll. I thank her and sit back down, she asks if I'd like a coffee and I say "Thanks but I'm ok."

Lucky for me no other staff come by as I sit and wait and about 5 minutes pass as Gloria comes back and tells me Jennifer should not be too long. We actually chat for a while as I am surely an interesting thing for Gloria right now. I tell her I have been desiring of such a job/lifestyle my whole adult life. I do not go too deep in detail especially about me being turned to as a prostitute but stick to maid stuff and how it excites me for such career. We keep chatting and then I see Jennifer walk from the back office area. She is blown away at the sight of me. I get up, curtsey and she has her turn asking me questions about my new lifestyle. The ladies and me talk for about 5 more minutes and then we say our good byes. I curtsey and almost tear up, my life as it has been is over, I am only a sissy now.

I walk to Master's car, get in an tell them its done, they just gave me two weeks severance and cut me lose today. Masters prefer this and tell me they will take me to my bank so I can in my sissy maid glory deposit my severance pay. God this humiliation will never end.

We pull into my bank branch and I am told to get out and go deposit my severance pay. Masters agree this should be humiliating and fun for sissy me. I step out, fix my desk and curtsey to then click, clock in my heels walks to and in the bank.

Heart pounding, face flush I step inside the bank and soon people see me, giggles are heard, some talking under people's breath, but most people try not to offend sissy me as I step into the line. I feel so embarrassed but God I love it too. A few people smile as the make eye contact with me. I see them scanning my outfit and heels with their eyes. One mature lady asks if I can clean her house later and the we hear casual laughs as they tell me I'm cute. Others then smile and giggle. I am asked by one lady why I am dressed like maid and I tell her this is my new career. I tell her I always wanted to be a sissy maid and I am employed as one now, it's fun and exciting work for me. She tells me that I bet I will make fine maid. I thank her with a curtsey and people giggle at that sight.

Soon I get to a teller's window and have her deposit my severance pay, we chit chat as she asks me about my outfit and she is genuinely curious and interested in my reply. She too tells me I make cute maid, I blush, curtsey and thank her. We finish up and I soon walk out of the bank and to Master's car.

I tell Masters of my experience and they enjoy it. But the also helps me get use to my new femme, sissy life in public. I will get better at the humiliation as life pass and I accept my new plight.

We get to my new home, Master Gage's house and I am told to put all my femme and sissy clothes and heels away in what will be my sissy bedroom in his basement. It's not ready yet for me as things have happened faster than we all figured, but from now on it's my bedroom. I spend about 15 minutes putting my sissy things away. After I am put in thy kitchen to put together a quick dinner for Master's Gage and Martin. I will have to make for myself and according to my Master/Slave Contract a more cheap and simple meal for myself. Master tells me to boil up some plain gruel and to heat up a can of chicken soup. As I make a quick but tasty stir fry meal for my Masters and a nice fruit cocktail dessert, I will be mixing in a soup bowl, my chicken soup and gruel to make a gloopy chicken soup flavoured gruel meal.

I serve the Masters and am allowed to at the table with them too. It all helps me accept my new sissy slave life. After dinner I serve the men some mixed drinks and I do the dishes. Once done I am told to do a few chores of Master Gage such as a load of laundry some vacuuming and they enjoy a relaxing night and talk about my future as a sissy maid and as a slut. Master tells me he will put me out on the local tranny stroll tomorrow night. He tells me that there is no sense in me not making money as a tranny slut right away. Of course I accept the decision but I am scared as it will be my first night as a sissy slut.

Before I am sent to my new bedroom its bed and to sleep, of course both Masters get a good night time butt fuck of their new sissy slut's ass. It's going to be this way everyday for me now.

[Next Day, Friday]

I wake up by 7:00am, enema, shower, shave, do my makeup, put on my wispy shoulder length blonde and auburn wig and dress in a satin pink maids dress over my white lace bra and white satin panty. I then pull on a pair of sheer pink pantyhose and step into a pair of pink patent 5 inch spike heel pumps. Make breakfast for both Masters, do some chores, and am taken to the government building to go to the office where I will fill out the paper work to legally change my name to Chantel LaFemme Swallows. Of course this was full of humiliation as the public and office staff see sissy me in my pink maids dress, pink hose and pink heels. But I endure and accept the humiliation. I soon finish and walk back to the car to tell Masters that it will taker about 4-5 weeks for the name change to become lawful. This said soon I will legally be Miss Chantel LaFemme Swallows. THIS IS SO EMBARRASSING FOR WHAT'S LEFT OF THE MALE IN ME! BUT SO EXCITING FOR THE SISSY FAGGOT I NOW AM!

We get back home, I am to strip only to my bra, panty and hose as I will spend the rest of the afternoon paint my bedroom barbie pink and dressed as such will make sure I do not get paint to spill to splotch on my maids dress. 


After I get back into my pink maids dress and heels, make dinner and later told to dress as a slut as tonight I will be pimped out on the tranny stroll. I'm so fuckin scared but shower, do my make up and dress up. I put on a black lace bra, some small breast forms, put on a padded black satin panty, a black lace garter belt. I carefully pull on a pair of black sheer back seem stockings. I put on a white long sleeve, satin blouse. and a black faux leather mini skirt. I pull out a pair on red suede 6.5inch spike heel pumps with a 1.5 inch platforms. I put my I.D. perfume and stuff in a shoulder purse and put on a black leather jacket. I look at myself into full length mirror and think, 'Fuck girl, you look fuckin hot, you are a very sexy tranny slut. Masters are going to love your slutty look tonight.'

I walk upstairs and show Masters my look and they fucking love it. I turn them on so much they have me give them each blow jobs before they drive me out to the tranny stroll. I am so fuckin horny too and I suck them off very well as they are in ecstasy. Soon though we are driving out to the part of town where many trannies stroll. It is an area of commercial and industrial buildings. So for most after 6:00pm they are closed and only a few businesses stay open. For instance one is a diner where they accept tranny hookers hanging out on breaks, but mostly it's deserted and only tranny sluts and Johns looking for quick, cheap and dirty tranny sex are out and about.

Of course my nerves are all amok as we drive closer and closer to the stroll. I've never truly prostituted myself and as such for a real pimp master wants me to make him some good money. I am pretty quiet and introspective as Master's Gage and Martin drive me out to the stroll. As we finally get there I see outside the car's windows, tranny prostitutes, I think to myself, 'God, this is it, this is what my life has come too, to be another cheap tranny slut making money for my black pimp master. Knowing the money I will make will be surrendered to him completely. All my fantasies have and will come true.'

Master parks by the curb near an area where working tranny girls congregate and work from.

Master Gage says, "Look Chantel this is your area and given how good you look and your age a good area to work. I want at least $600 tonight, I know it's your first night but you look good and I'm sure enough horny guys looking to fuck some tranny slut ass or have one suck their dicks will hook up with you."

I reply, "Yes.. Yes Master, I'm every scared though."

Master Martin pipe in, "Bitch with them legs, tall heels, short skirt and good slutty look you will be too busy to be scared."

Master Gage adds, "Look it's easy Chantel, flash your body, shake your ass and be upbeat to any dudes who come to you looking for some action. There are fucking and sucking areas all over here, behind garbage dumpsters, under stair cases, by doorway entrances, behind the backs of buildings, parked in cars, lots of places for you to be the whore you want to be Chantel."

I reply, "Oh.. ok, you are both right Masters, I'll be a good girl, I'll work hard to make you the money."

I am instructed to step out of Master Gage's car, which I do, he tells me they will be back at 12:30am, that gives me over 5.5 hours too work it, I curtsey and thank them. They then drive away. I am so nervous, what if there other girls not like me, am I stepping on any other girls area? I begin to walk to where a couple of girls are standing.

First girl, "Hey hun, you look new here."

I sheepishly reply, "Um, yes, it...it's my first night. My pimp master has put me out now to work for him."

Second girl, "Shit you look good girl, love your shoes, they compliment your sexy legs."

I reply, "Thanks."

First girl says, "My name is Tracy, this is Kelly. and your name hun?"

I answer, "My name is Chantel."

Tracy asks, "So you say you are being pimped?"

I reply, "Yes... yes I have always wanted a Master who will pimp me as a prostitute."

Kelly adds, "Well a pimp is a double edge sword, you get acre of knowing you have a pimp who will protect you but you are also under his thumb, but if that's what you like girl, good for you."

Tracy adds, "Yeah, I'd say most trannies like us work freely, I'd say about 30% here are pimped."

I reply, "I've always felt submissive and sissyish so I have wanted live with and hook for a Master. All has recently fallen into place and her I am my first night as a street walker."

We all chat of a few minutes, the girls tell me areas where I can take men for sex. They tell me that most men I will likely do are gonna be between age 30 and 60, ironically most married, some divorced and the rest mostly younger dudes single and fuckin horny for quick tranny sex. It's relatively safe here as most of us girls stay near by, but it can be rough and some dudes want sex but do not think they should pay for a tranny to do it.

Both tell me they have been assaulted by bad Johns and a few girls have had to go to the hospital. I ask about cops, and the tell me since we are in the commercial/industrial area and if we stay here and away from any residential type areas they don't bother us too much. Once they see you as a new girl they will probably run ya for any arrests and such but mostly leave ya alone. I'm told to not tell cops I have a pimp though. They tell me social workers will probably be by to talk to me about prostitution and such to try and help me, but the know most trainees who prostitute was to do so and enjoy it.

They tell me the diner up the street is where we go to take a break get a load off our heels and to touch base with each other. You will be a part of our group community for safety and support. That makes me feel much better. This said they notice a car pull up and ask if I want to give it a try? I'm so fucking scared but I note to them I will approach the John in this car.

I walk up to the passenger side and the window is down.

I ask, " Hi..hi hun, you looking for a date?"

The guy says, "Maybe... ahh you are a tranny right?"

I reply with a smile, "Yes, hun, you like trannies?"

He says, "I love trannies as I find that they are wanting to really please. "

He asks how much for a date?"

I reply, "$40 darlin, I suck or take fuck for $40."

He pauses and then says, "Ok... ok... that's fine, you got an area you want to do it?"

I look up and see down an alley a few garbage bins and say, "Um.. you good behind a dumpster? If so just park your car over there (as I point to a parking loot) and I'll meet you by that dumpster (as I point to it)."

He nods and drives off to park. I strut in my heels across the street and through the parking lot to stand by the garbage bin. Soon I see the guy park and step out, he's white probably 30 or so about 6 ft. tall and maybe 200lbs, wearing a polo shirt and jeans. He gets to me and asks my name, I tell him it's Chantel and he likes that name a lot, he tells me his name is Gary. He has only been with few tranny working girls as it make him nervous but he loves the way we dress, act and look. He finds sex with us very hot. I tell him that I'm rather new here but eager to please. He pulls out his wallet and grabs 2- $20's and gives the to me. I put them in my bra.

I ask, "So what do ya like Gary?"

He excitedly replies, "I really would like a blowjob."

I reply, "No problem hun, come lean against the wall behind the bin here."

To which he does and just looks at sexy, slutty me.

I get down on my haunches and look up at him, with a big smile, toss back my hair and tell him to relax. I then undo his belt, and pull his jeans down. He is in briefs and I see a stiff bulge in his briefs, I smile and tell him it looks like we both are gonna enjoy this. I soon have his briefs down and before my eyes is 7 inches of nicely thick cut white cock.

I say with a seductive tone, " You have a nice cock."

He smiles and says, "Thanks, please suck it, suck me off."

I grasp his balls with my left hand and stroke his cock with my right, really getting him hard. I look up at him, toss my hair back again and smile as I now move towards his cock and take my tongue to dance around his cock's head. The moans Gary gives are intoxicating and I love it. As I keep doing this Kelly walks by her heels clicking with a rather mature more heavy set man and she says to me, "You go girl, make your man happy."

I stop look over my shoulder at her and say. "Mmm, thanks I will." as I move back to playing wit Gary's stiff cock. I tongue the back of his shaft from his balls forward to the tip and he is pounding the walls with his hands in growing lust.

I now take his 7 inches as best I can in my mouth through my red lipstick colored lips and my tongue working it inside my mouth. I slurp up lots of saliva as we get into some series head bobbing own his cock. The moans and groans the both of us give is so seductively erotic. I enjoy the feeling of Gary's stiff white cock in my mouth and he fucking loves the blowjob he is getting. We keep working with me bobbing and slurping his cock. Gary can't help to not run his hands over my head and through my hair. This excites both of us to get even more and more with it.

I can sense Gary is working up to his eventual prize of a hot orgasm into my sissy, slutty mouth. We keep moaning with mutual lust and joy. I can sense every second that goes by Gary gets closer. I want him to cum in my mouth badly as I bob harder and harder on his cock.

Gary in hard lust says, "Oh shit, I'm so fu...fuckin close..ahhhh...ohhh."

I work it and work it as he comes closer and closer as I feel his firm hands now grab the back of my head and push me on his cock hard.

He is excited and says, "Fuck, ahhh...ohhh.fuck, yeah..ohhhhhh!" as he lets to a thick gooey wad of his hot and sperm filled cum inside my mouth as I swallow every drop and love it.

He pulls out, we make eye contact and we both smile as he pets my head and tells me that was fucking great. I tell him I am happy that he enjoyed it. I tuck his dick back in his briefs and do up his pants. I get back up off my haunches as he helps me up on my heels and we both walk back to his car and he gets in and says he will see me again soon. I smile and say to him yes we will. He drives off and I walk back to the street corner and talk to Tracy and Kelly as they introduce me to a couple other girls, Jenny and Krissy. All four of them are and to me the new girl. But soon it's back to work as I am offered another car that has pulled up. I am more confident already.

I strut over to this car my red suede 6.5inch spike heel pumps on 1.5inch platform clicking away with each step. I lean into the passenger side window.

I say, "Hi, how are you tonight?"

Driver in car replies, "Fine, nice night and you hun?"

I reply with smile, "I'm good darlin, you looking for a date?"

Driver says, "Um yeah maybe, you are pretty hot, nice legs."

I reply, "Thanks hun, do I really excite you? turn you on? you like chicks like me?"

Driver excitedly says, "Umm yeah, I got a boner in my pants right now, how much?"

I smile, wink, "$40 darlin."

Driver says, "Ok, sounds good, um where do you want to go?"

I say as I look up and down the ally where I was before, I see a gal and a John by the garbage dumpster so I scan to see under a stairway, "Looked like that stairway down the block there can be good. You park and I'll walk there to hook up ok?"

He drives over to park as I begin my strut to the stairway. I get there first and wait for him. He steps out of his car, he's a mature white guy maybe 50, average height and weight, in a business suit, so he is some sort of professional. He calmly walks towards me and stares at my tall, slender body, with my short black skirt, black stockings, red pumps and all.

He speaks, "My name is Ben, you look so hot and new here."

I smile and reply, "Hi Ben, my name is Chantel and thank you, yes I'm new here, it's my first night on the stroll here."

Ben speaks, "Lovely name, can I just look at you for a minute, maybe run my hands up and down your stocking clad legs?"

I reply, "Sure you can Ben, but first I need my donation."

Ben coughs and says, "Jeez sorry hun, I am totally turned on by you and I forgot." he reaches in his wallet and hands me two $20's as I put them in my bra with the other cash I have.

Ben then runs his hands up and down my stocking clad thighs as he pants with desire. He can't help but not to get close and grind on me as his hands go wild on my legs.

Ben all worked up says, "God you are so sexy, I do not care if you are a chick with a dick on the stroll here, I love your look, fuck I'm so damn hard."

I ask, "What do you want to do Ben?"

Ben excitedly replies, "I want up your skirt and in your panty. I'm so fuckin hard I need my cock up your ass girl."

I now proceed to undo Ben's pants and drop them, I feel his bulge in his boxers as I pull them down and both my hands fondle his cock and balls. Ben is hot with delirium and a****l drive to want to fuck me. He is 6 maybe 6.5 inches long but nice and thick close to 2 inches and uncut. I reach into my purse and grab some lube as I then rub it over his stiff cock. I then turn around and lean against the wall under there stairway lift up my mini skirt and pull down my panty. I look over my shoulder and hand Ben the tube of lube and ask him to finger my butt hole with lube. He excitedly grabs the lube and soon is fingering my hole working the lube in it. He is sighing with desire and I am moaning with lust at him fingering me. Soon the tube of lube drops to the ground and Ben says he has to fuck me now, fuck me hard. I toss my hair and look over my shoulder bent over, my ass exposed and tell him to go ahead, fuck my tranny ass.

Ben takes his hands and pulls my cheeks apart to open up my tight little hole and he begins to work his stiff cock inside me. I let out a bit of an ouch and such as he stuffs his tool past my sphincter and he is so hot with lust. But he gets inside and works slowly at first as I moan and he groans. His cock is pushing nice and I feel it on my prostrate, if I was not in chastity my sissy dick would be hard. But I coach Ben on to give it to me, I moan and sigh as he gets harder fucking rhythm going. We begin to work in sync as his hands hold my hips and we move back and forth together. Ben tells me how fucking good it feels and how tight I am. I tell him to keep going between my moans.

Ben really gets into a hard pounding ass fuck on me to the point of me almost falling off my 6.5 inch spike heels. His grunts get more a****l-like and I am more passive in my moans as his cock invasion of my tight ass gets hotter and harder. It is incredible for both of us and the wild sex I as a sissy slut and rather sexy cute tranny wants and deserves. Ben pounds away relentlessly as we moan in mutual rhythm and soon I sense he will soon let go inside me. I so fucking much want his cum up inside me, I feel like the dirty whore I am and love it.

Ben with a panting breath says, "Fu...fuck... ohh Chantel. ahhhhh gawd yes... so fucking close... oh you lil bitch, you got me so hot...ahhh...ohhhh, yeah .. all...almost their...ughhhh yeah, yeah, fuck yeah, I'm coming up your lil ass." as Ben fills my rectum with that awesome cum juice, one of the best things a real man can give.

Ben slows down, panting and thanking me for such a great fuck. He is so enamored with me he leans forward and kisses the back of my neck, telling me I am the perfect tranny slut. He pulls out and I turn and drop to my haunches as I grasp his softening cock and lick him clean. He loves it.

I sigh and say, "Ben you are a good fucker, I loved your way up my butt hole, I'm glad you are so happy."

I tuck his now soft cock in his boxers and pull up his pants as he pets my head and tells me he definitely wants more sex with me in future. I agree and soon he walks away. Before I put myself together I grab some tissue from my purse and wipe my butt hole of lube an some of Ben's cum that back flows. I discard the balled up tissue, fix my panty and skirt and walk back to the street corner.

Tracy an Kelly are also back and ask me how did things go? I say they went great. As we all stand in our heels strutting like there sluts we are I get a few more dudes for dates, three more blowjobs and two more butt fucks. I'm doing well for my first night.

By 10:00pm the girls ask if I want to get a coffee at the diner. I agree and the three of us walk to the diner, we get some coffees to go and Tracy was kind enough to pay for mine as. We sit at an outside table, take off our high heels and rub our feet. I love my heels but they can be hard on one's feet. I find Tracy is 35 and has been working for 7 years after her divorce and needing money to survive. She still keeps a bit of a day time life but mostly she lives enfeme and prostituting has paid her bills. She has been robbed a number of times and beat up a few times, it happens she says. I ask her if she plans on quitting. She says not any time soon. it makes her more money than her day time work does.

Kelly is 42 has been a tranny hooker for 12 years. She too is divorced with k**s but they do not know she is a tranny slut. She has come to accept this lifestyle and loves the clothes and the sex so she is able to buy a lot of clothes with this lifestyle. She tells me getting robbed happens but not so much on this stroll. In another city she once worked it was bad for tyrannies. She was once beaten up badly and she was in hospital for a week. Some 250lb. dude just went ape shit on her after he had her suck him off. He gave her two black eyes, bruised cheeks and cut her lip as well as twisted her right arm. It was bad, but she says it comes with the job. She is much more careful today. It is safer to be a tranny slut here.

Soon we are back on our corner and I am told to go onto a new parked car. I walk up to the passenger side and see two men inside. As I peek inside I see two young dudes who are twins. They tell me it's their 30th birthdays and they both want to get on with a tranny working girl. I am intrigued at this and tell them ok. They ask me how much for a date. I tell them $40 for each of you.

Driver says, "Come on, it's our birthday, how about a discount?"

I smile and reply, 'Hmmm ok hun, you two boys can get a date for $30 each."

The look at each other and back at me and agree. They ask where?

I look around and see it's busy with other girls in our area I see a parking lot and say park in back in the dark. We can use you car as a place to get it on. They agree and I tell them I'll walk over there and the can park. They drive off and I strut in my heels.

They park first and both step outside and wait for me. They are two 30 year old white males about 6'2" and 220 lbs each, blondes, tanned in good shape, one in a blue button down shirt with black jeans on the other in a white button down shirt and blue jeans on.

As I get to them they introduce themselves, "Hi I am Jordon and the is my brother Tate."

I smile and say, "My name is Chantel, nice to meet the both of you."

Jordon hands me $60 and I stuff it in my bra as I ask, "So men what do you all want tonight?"

Tate says, "Well Chantel, we figured one of us gets sucked off by you as the other fucks you, are you ok with that?"

I think, "Nice a suck and fuck.' as I say, "No problem boys, why not just have one of you sit on the hood of your car so I can bend over and give head while my ass is ready for the other to fuck, you all like that?"

They nod and agree. Jordon undoes his pants and briefs as he then sits on his car hood, he is maybe 7 inches and average in girth, as well as cut. I see Tate drop his pants and briefs and his cock is the same. I hand a tube of lube to Tate as I bend over and lift my skirt and pull my panty down, "Lube my ass Tate.

Tate begins to lube my ass and as he does that I begin to play with Jordan's cock, licking its head and shaft. Jordan is horny and hard. I keep him going as I wait for Tate to now begin working his cock up my ass. As he does I slow on my cock an mouth play with Jordan's cock. But in a little while Tate gets going in fucking my ass. Soon we are quite a sight, sissy slut me bent over one cock in my mouth the other up my ass. The guys are moaning and loving it and I am in a state of thrill too as the is my first suck and fuck.

The guys get really into it, my mouth is being well fucked by Jordan's cock an Tate is pounding my butt hole hard with his. The grunts, sighs, moans and groans are like us playing in a sexual choir. My life as a sissy slut is now quite hard core.

The two boys give it to me relentlessly as soon I sense Jordan can't contain himself and snorts to a grunt as he cums in my mouth, filling it with his hot sexy jizz. He leans back as he pulls out and sighs as he comes back down. Meanwhile Tate is on my ass like a raging bull and is pounding me hard I again almost fall off my heels. But moments later he howls and shoots up my butt hole a good thick wad of his hot jizz. He quickly pulls out and comes back down too. The men fix their briefs and pants I pull up my panty and fix my skirt. The both tell me that was the best birthday present they ever gave each other. I tell them I am happy for them and they get in their car and drive off. I go back in my purse, grab some tissue and wipe the lube and cum from my ass.

Back on my street corner and I chat with the girls. The night goes well and surprise surprise I make $600 that I will give to my Masters when they pick me up.

By 12:30 am or so the car arrives and I say cya later to the girls.

I get to Master's car and he asks if I made quota. I smile and say, "Yes Master, $600."

Martin says, "Shit man her first night and she gets quota, she's a natural slut."

I am allowed in the car and they ask me how it all went. I happily recount my sex night for them and they are sure I am the perfect sissy slut. As we drive home I realize all that has come and changed in my life. My fantasies are now my realities. I'm sure it's going to be hard and tough but I am a natural sissy, who love being one and used and a maid and a slut. I will be broken to accept all that will come. WHAT A JOURNEY I'M ON!

[Beep, beep, beep] My alarm clock goes off and a struggle to wake up. It is 7:00am and I come around to realize I'm in my sissy bedroom in my Master's house. I get up quickly now, in my white satin bra and panty with white satin full slip, this is my sleeping lingerie. I take off these clothes and scamper to the bathroom with now only my chastity device on.

Once in the bathroom I prepare my enema set up and soon stand in the shower with the tube inserted up my butt hole. I release the solution and it begins to fill my rectum. It's a weird feeling as I begin to fill up. Once it feels as if my rectum is full I clamp off the hose and pull out the tip. I bend over and let the solution sit inside my rectum. Minutes pass by, then I evacuate the solution in the toilet. I am now sissy fresh on my back side.

I shower, shave and then move to my bedroom to begin dressing. I white satin padded panty and matching satin bra and soon I put on my makeup, once done I pull on a pair of white pantyhose and a white camisole then white petticoat. I then pull one of my pink satin maids dresses with frilly white lace and cute white satin and lace apron. I put on my wispy shoulder length blonde and auburn wig and a pink and white lace maids cap. I look at myself in my make up mirror making sure my sissy face is right and soon I grab a pair of pink patent 5 inch spike heel pumps to put on. I look now in my full length mirror and am excited at my pink sissy maid look and curtsey for myself.

I see the clock and that it's about 8:00am and I must get to the kitchen to prepare breakfast for Master Gage. In my heels I prepare what he has noted he wants, 3 eggs, sausage, toast, orange juice and coffee. I am to serve him breakfast in bed today.

About 15 minutes pass by and I have serving tray set up. I pick up the tray and walk in my sissy style and 5 inch heels to Master's bedroom. I place the tray on a table by his door and knock asking if he is awake and once I know so ask if I may please enter.

Once I enter with the serving tray of his breakfast. He sits up and I place the tray, with legs folded out so he can sit in bed to eat.

Once doing sir I curtsey and say, "Good Morning Master, your breakfast is served as you have ordered, I hope it pleases you."

He then picks up the tray and kick the blanket off him exposing his body and his boxers.

He looks at me, smiles and says, "Chantel I want you to get a breakfast treat, get on the bed and pull my boxers down. Then I want you to fondle my cock and balls."

I curtsey and say, "Yes Master." as I get on the bed on my hands and knees. I then fondle his cock and balls as his cock hardens up.

Master says as he sips his coffee and takes a bite of toast, "Ok Chantel you slut, suck my cock."

I look at him and say, "Yes, Master." as I move my lips over his 8+ inch lovely black, cut cock. What a sight it must be for Master to see a faggot sissy like me in my pink maids dress, wig, makeup, hose and heels sucking his cock for a breakfast treat. I work up saliva as I begin taking his glorious dark meat in my mouth and roll my tongue over it with my lipstick covered lips performing good sissy seal.

Master takes a big gulp of his orange juice but has to stop as the feeling of a morning blowjob excites him greatly he says, "Ahh fuck that feels good Chantel, Jeez you are becoming one hell of a cock sucker... Mmmmm...ohhhh...ahhh!"

I feel sissy pride growing as I work on his great big black cock. I keep working on it, sucking and bobbing my head as Master grows more in lust. It's a wonderful faggot-like feeling a sissy like me feels. I keep on slurping and bobbing my head as Master now takes his hands and pets my head, running his fingers through my luscious wispy wig hair.

Master goes on, "Ahhh...ohhhh...ummm...ahhh..yeah, fuck yeah... jeez girl. umm yeah."

I work and work and soon I feel his ejaculation moving through his vas and I hear as well as feel the thrust and a grunt as he shoots out a hot, juicy load of his manly sperm filled cum inside my mouth. I think, 'God, I love swallowing sperm, millions of real man's sperm in my mouth and swallowed to my sissy tummy.'

I now slow and pull off his cock and I look at him and swallow all of his cum, to then show him my empty mouth. Master pets me and tells me I am a good little slut. He has me get off his bed and sends me to the kitchen to make myself a pot of plain gruel as he finishes his breakfast. I get up, curtsey and am on my way.

I quickly make and eat some plain gruel and am allowed a cup of black coffee. Minutes later Master calls and I scamper in my heels to his bedroom and curtsey before him as he has me remove the breakfast tray and hands me a list of chores I shall carry out today. I thank him curtsey again, tray in hand and go back to the kitchen to wash all the dishes from breakfast.

Master showers, shaves and dress as he readies for going to his work place. He checks on me in the kitchen and see's I am on top of washing dishes. He reminds me that the chores and what I see as a shopping errand for groceries must be completed before he comes home from work. I acknowledge it all with a curtsey and thank you. Soon he is on his way and I am alone in Master's home.

I finish up my dishes and move on to there chores list. It reads:

Chantel, you must do and complete the following before I am home for dinner at 5:00pm.

Wash my laundry including a change of my bedding

Vacuum the whole house

Clean all the bathrooms including scrubbing toilets and floors

Iron and put away cleaned laundry

Clean the kitchen and scrub the floors.

Go on a shopping errand to the local grocery store, list off items to buy is attached.

Dust all areas needing such in the house.

Prepare my dinner

Greet me at the front door once I return from work.

Signed: Master Gage.

Off to start my chores I now go. For the next 3 hours I work away in my maids dress and heels. It's hard work especially in 5 inch heels. I do not take them off as Master has video cameras recording my actions through out the house, if he see's I have taken off my heels I will be punished.

About noon I can make a quick lunch, plain toast and black coffee. I then brush my teeth, fix my makeup and spritz on some perfume. It's a pleasant day so I will not need a jacket as I now leave to go grocery shopping.

In my car my nerves are growing a fluster as I will shortly be in a grocery store wearing a pink satin maids dress, white pantyhose, pink 5 inch spike heel pumps, wig and makeup. The drive to the store goes well and soon I park. I relax and try not to hyper ventilate with nervousness but soon I pop open my driver's side door and step out planting my heels on the asphalt. A sweet breeze caresses my pantyhose clad legs and up my short pink maids dress. I begin walking an my heels make that oh so lovely and erotic click clock sound. People coming and going soon see me in my pink satin glory and many a comments are spoken with giggles. Some phones are pulled out to take pics of me with and I endure this sissy humiliation.

I enter the store and grab a shopping cart, pull out Master's list as I begin the humiliating walk through the isles. People giggle and comment under breath but I hear some comments, lots of "Look at the sissy." "Look at that fag." "Cute maids dress." " Wow look at the heels." etc. But I persevere and put items from the list in the cart.

I am looking at loaves bread when a lady and her teenage daughter pass by me. The girl can't help but not stare at me as she says quietly but with in my hearing, "Mom, why is that man dressed like that, he is in high heels and pink maids dress, white nylons, makeup and a wig."

Her mother blushes as she looks at me, smiles and says, "Honey, sometimes some men just like dressing in feminine clothes, lets leave him or her alone, as she looks at me and adds I'm sorry if we embarrassed you."

I politely interject, "Not to worry ma'am, I understand how and why you and your daughter may look at me. Yes, I am a sissy, a sissy maid, I enjoy the lifestyle. I mean no harm but I am employed as a sissy maid."

The mother says, "Thank you for making it clear, we both hope you are happy dressing as such. Nowadays it's a lot easier to be a trans type people."

I thank her and we all move along. I go on shopping and being curiosity to the pubic and staff in the store. I now move to the check out and get in line. A couple ahead of me can't help but notice sissy me and chat with me as to why I am dressed as such. I tell them I am a happy sissy maid and we enjoy a nice chat as both compliment me for being cute pretty as a sissy maid.

The checkout lady asks about me too and we chat as she runs the items through the sale. I am now on my way and drive back home.

Back home it's back to my chores and I get all of them completed as Master expects. I get dinner started and watch the clock. I too see Master shall be home any minute. I next hear Master's car pull in the driveway and I scamper to the front door. Open it as daintily I can and when Master steps in I curtsey and greet him with a, "Good Afternoon Master, how ass your day?"

He smiles and says, "Good Chantel. Did you get all your choices done? and do the shopping too?"

I reply, "Oh yes Master, it was all good and exiting."

We move to the living room. He tells me to get him beer and I do so serving him as the sissy I am and we too get ready for dinner. He gets a good home cooked meal. I get gruel mixed with tomato soup and plain toast with a tall glass of water.

Master tells me what is up for the slut in me tonight. I'm a scared but listen as he explains. Master Martin will arrive by 6:00pm. I am to freshen up, give myself another enema and dress up as slutty as I can. Master Martin has made arrangements for men to sign up and pay a donation of $40.00 each at the 24 hour sex shop we were at a few days ago and this list will be taken with us to a cheap rent a room by the hour motel. I am to be a cheap motel slut all night long and a long list of horny men will come by for quick, cheap, dirty sex on my slutty body, mouth and ass.

As I move to freshening up and changing into a slutty outfit I am excited but nervous with all the sex I am to have tonight. I change into a black satin bra with my average size breast forms. I pull on a matching padded black satin panty. I put on a a cute sexy, lacy garter belt and pull up a pair of black stockings which have imprinted on them in white the word SLUT all over each stocking.

I enjoy the sexy and slutty look these stockings have. I decide to put on a black spandex type short dress with a short, loose pleated and fluffed figure skater type skirt section. This dress barely covers my sissy ass and panty. My stockings and garters will clearly show. I put on a pair of black velvet 5 inch spike heel pumps with cute black velvet ankle straps. A few sexy gold bangle bracelets on both wrists, red nail polish to match my red lipstick and smokey black and bronze eye shadow and black eyeliner. My wispy shoulder length blonde and auburn wig finishes my slutty look off well. I fill my purse with things I need and put on a short black leather jacket, stand in front of my full length mirror, smile, extend my legs out one at a time in my heels and sexy stockings, shake my ass and tell myself, "Girl you are hot, men are gonna enjoy your ass and mouth tonight."

I walk to the living room where Master Gage an Master Martin now wait. As I step in they light up with excitement at the slutty me. I curtsey and tell them I am ready for my performance tonight. Of course I am nervous but excited.

We all drive out to this fleabag motel and once there the manager who is friends with Masters walks us to a corner room and lets us in. I video camera is set up to record all the sex I will soon be having here. The bed is ready and I am told the first men will be here soon enough. The Manager will meet them in the office and send them the way. I will be greeting each and all as they enter the room and wait for what sex these men will want, oral or anal. The bed will get good use tonight I am told. I have not been told how many men have signed up, Masters know but keep it from me.

Minutes pass and then the door opens as four men walk in and see me along with Master's Gage and Martin. I greet them and they are all hot with my look. They are four men in their 30's all white males of average height and weight. Soon they decide who goes first and he tells me his name is Fred I tell him I am Chantel. I now sit on the edge of the bed as I now undo Fred's pants and pull them down. Next I pull down his tight briefs and plops out is about 7 inches of nice cut white cock. I tell him his cock is very sexy and he says for me to suck him off now. To which I look up at him with my smokey eyes and smile as I cup his balls and take his cock into my mouth through my red lips and start sucking him off.

Masters run the video camera and the other guys gulp and love what they are watching as Fred gets hot with lust as to my sucking of his cock. Soon we are moaning together and I sense Fred enjoys this. He pets my head as I bob on his hard cock. My tongue dances around cock and it really excites him. He tells me it feels so fucking good.

I keep on bobbing and sucking as my lips and tongue makes him horny and wanting to soon cum. His moans and my slurps are great together. Great video is being captured. I can sense Fred is getting close and I want to make him happy as I'am such a fucking slut.

Fred is all, "Ohhh... ahhh...f...fuck... ahhhh so...soon, gawd..soon you bitch... Ohhh.. fuck yes... ahhh...yes.. YES! AHHH!" as he shoots his huge load of musty but hot and gooey cum in my mouth. Oh my God he fills my mouth with his hot cum and I swallow every glorious drop.

Fred pulls out and I look at him to see him sigh and smile and I thank him for the privilege of sucking him off. As Fred pulls away, the next guy gets ready, his pants are already off and he is only in his briefs as he says, "I'm gonna fuck you. Get on the bed and in position to take my 7 inches of thick white uncut cock."

I say, "Yes sir." as I assume the position, pull up my too short dress, pull down my black satin panty and grab the lube to finger my butt hole. More awesome video is being made by my Masters,

As I lay on my forearms, my face resting on a pillow, my ass is up in the air, I then look over my shoulder and see a man who tells me he is James get on the bed, briefs now off and he is playing with his cock as he moves to my ass. His hands now grab my butt cheeks and firmly plays with them. He soon pulls them open to show him my now lubed up butt hole and he begins to push his 7 inches of stiff cock up my hole forcing carefully through my sphincter as I grunt and groan as does he. Our breaths pant together as he so wants to fuck my tight little ass. I whimper as he gets in and soon he slowly works into a fucking rhythm. It takes a bit but the lube helps and James soon gets going into a good hard butt fucking pace. We both moan and groan together and it feels so fucking good. I can tell James loves this feeling and wants to enjoy the whole session as he pounds my sissy slutty ass and his hands firmly hold my hips. I tell him how good it feels and it only jacks him up higher and harder in fucking my ass.

Soon we are near a****listic in fucking and the other men cheer us on. I can feel James is getting close to his wanted prize of ejaculation up inside my rectum. The feeling I get from myself making a horny man want to cum is beyond me. I know I am a sissy bitch and I want the cum. As I sense James is about to let go, he does with a loud grunt, hard thrusts and sighs as his cock fills my rectum with his hot, sticky sperm filled cum. I fall my head into the pillow as I know he has cum inside me. James slows and then pulls out, steps off the bed and I get back up on my forearms look over my shoulder and thank him. He puts his briefs back on then his pants. I move back and sit on the edge of the bed and some of the cum James gave me spurts out of my sissy ass.

The next two men both fuck me as such and soon they are all gone. Master's tell me I did well. Minutes later six more men come in three white guys, two black guys and one Latino. All firm and strong raging from 30 to 40 years of age. I find as these six do me, 3 blow jobs and 3 butt fucks they range from 6 to 8 inches in cock size all good girth and 4 of the 6 are cut. For the next hour these six men have their way with me and I am wild with hard core anal and oral sex. The shots of cum each man gives me is in my mouth tasty and erotic, the ones up my sissy ass is so hardcore hot for me to feel. So much cum down my throat and up my ass as much of it back flows wetting the sheets.

After these six go on, Masters let me drink some water to wash the cum down well. I am soon ready for more men as the night is still young. I have had sex with ten guys already and next I find six more men come into the room, all white and younger between 20 and 30, All average in cock size about 6 inches or so each. I smell booze on these guys and they all seem new to fucking a tranny slut.

They tell Masters they love my look and my slut imprinted stockings as well as my high heels. Being younger they all will get off sooner. All six decide to butt fuck me and each enjoy ravaging my ass. I am totally on with this sex, the stream of butt fucking, hard cock pounding my butt hole and filing my mouth, parting my red lipstick covered lips and allowing me to work my tongue on said hard cocksucking. The life of a sissy slut is being successfully burned int9 my floozie, sissy mind and persona. This group of men all fill my rectum with their cum and fucking love it, I want. The smell of cum now wafts in the air and cum spots are all over the sheets.

When all six are done they tell Masters I was a great fuck for them. After they leave Masters tell me how proud they are of slutty me. As the night passes by I get more and more horny guys, white, black, Asian, Latino, all horny for cheap tranny sex. It is a most hard core evening for me. I am amazed at how many guys signed up to pay $40.00 each for this cheap, tranny sex.

By midnight Masters tell me that thirty men have used me, really? Thirty fucking horny guys. Twenty of them butt fucked me and ten fucked my mouth.

Masters tell me a few more guys still to come and as such I will endure their relentless invasion of my sissy mouth and ass. As this last group of men come to take their $40.00 worth of horny pleasure on me, my ass and my mouth, soon the rest of these horny men are all done. Thirty five men, twenty two fucked my ass and thirteen fucked and filled my mouth with cum. My God at $40.00 equals $1400.00. Damn, what a good haul for my Masters. I get to keep none of the money from this wild gang bang night. I keep only my slutty memories and many minutes of slutty video, that will be posted online on my sissy blog and other porn media.

As I clean myself up, put myself back together and we then all head off for home. I know I pleased my Masters. I know I am one Hell of a slut and a sexy slut too. My life as a sissy maid and slut is complete. I am getting use to this life and I will accept it from now on as my own. It's tough but also exciting. The sissy I have known I have been my whole life needs a Master and the sissy feelings I now live must remain and be 100% of my life. Time will make some of it all easier, but living under the thumb of a true Masters will be hard on me for a longtime to come. But my fantasy is now my reality. I will be ok as a sissy maid and slut. It's in my nature to be such a sissy maid and sissy slut. My sissy life is complete and will be all I now know and live.