From Straight to Cock Slut
I am 25 years of age and stand six foot two inches tool and have an average body – it used to be an athletic body however injuries playing sport growing up has resulted in me putting on weight while recovering from all the injuries.
Growing up at school I was far from a "chick magnet" however had my fair share of summer romances, one night stands and semi-serious relationships – however it wasn't until I turned 19 that my life changed forever and turned me into the type of person I am today.
My best friend Scott and I had known each other since we were about three or four and went to pre-school together, Scott was slightly shorter than me about six foot but everything else about him was almost identical to me.
Our families had grown close together over the years as we became best of friends, we would spend nights and even whole weekends staying at each other's house, Christmas normally saw our families getting together on Christmas morning to have breakfast – in a way it was one big extended family.
One Saturday, shortly after my 19th birthday Scott and I made the trek to the local sports oval where we were players on the football team and took part in our match, after we headed back to Scott's house where we were going to prepare for a night of drinking.
Scott had recently moved back in with his father Stephen after his mother Louise had left Stephen after 22 years of marriage to be with another man, Scott's father was not coping that well and so to look after him Scott had moved back in.
After a number of quiet drinks at home Scott and I decided that we wouldn't head out to a night on the town clubbing, both of our bodies were aching after a hard fought football match earlier in the day and instead opted to have showers, and watch a couple movies in his room falling asleep whenever we wanted.
After watching the first movie the second one started and I dozed off to sleep, awaking several hours later with the desperate need to go to the bathroom to relieve myself – emptying the tank from the beers we had had earlier in the night.
On the way to the bathroom I saw that the lounge room light was off, however there was a blue and white flicker meaning that something was on the television.
After washing my hands I made my way to the lounge room – I walked quietly in case Stephen had fallen asleep, I didn't want to wake him.
As I got to the opening in the wall to head into the lounge room I poked my head around and looked at the television to my astonishment on the screen was a pornographic movie, it had one blonde female getting pumped by two penis' one entering her ass, the other filling her mouth.
I looked down at Stephen who was laying on his back on the couch, it took a couple moments for my eyes to adjust properly and when they did I realized Stephen had his penis hanging out of his pants and he was stroking a penis that looked to be about 9 inches.
Out of the blue, and catching me by surprise, Stephen looked at me – I later found out that I had gasped and he had heard – as he looked at me and realized who I was he quickly stuffed his penis back into his pants and zipped up once again, clicking stop on the DVD player at the same time bringing the movie to a screeching halt.
"I... I... I'm so sorry" I stammered as Stephen looked at me with a blank look.
"No need to apologize at all" Stephen said. "Come join me" he said patting the couch seat next to him.
I stopped and thought about it for a second, I was never interested in seeing guys masturbate, I didn't want to be around it and had no interest in all... however this was Stephen, there was beer on offer and I wanted to see what happened with the DVD on the screen – I had seen many of DVDs from Stephens collection while growing up but had never seen this one.
"Only if one of those beers is for me" I said after taking a deep breath and pointing to one of two full cans of beer on the coffee table.
"Off course one of them are" Stephen said. "Anything that is mine is yours after all, you should know that by now" Stephen said picking up one of the cans and handing it over to me.
I took the beer and sat on the couch next to Stephen popping the tab of the beer and taking a mouthful as Stephen picked up the remote and pressed play to kick the DVD back into action as the ladies muffled moans filled the room.
It didn't take long before I began to grow hard with what was happening on the screen, and a quick glance over to Stephen told me he was horny as well if the tent in his pants was anything to go by.
A short time later the scene of the DVD came to an end and another one was about to begin, Stephen stood up from the couch and started walking out of the room.
"I am getting another beer, you want one" he asked as he walked past me facing the television.
"Sure" I said as he exited.
The scene that started on the DVD shocked me. As it started it had two guys laying on the bed kissing, one then pushed the other flat on his back and kissed his way down his body to his penis where he started kissing it, licking it before taking it into his mouth sucking it.
For some reason my penis responded to what I was seeing on the television screen as Stephen came back into the room carrying the beers handing one to me.
He sat on the couch next to me once again and our focus turned back to the television screen. A couple minutes passed and I saw Stephen fidgeting out of the corner of my eye, I glanced over at him and he had once again pulled his penis out of his pants and was stroking it once again.
I was fixated on the size of it; it looked to grow bigger with each and every stroke he made.
"Do you want to touch it" Stephen said almost laughing as he said it, snapping me out of my thoughts. I quickly glanced back to the television screen as thoughts flooded my mind, did I want to touch it? Would it make me gay? I was confused.
Stephen had thought I had gone shy and looked back at the movie showing on the television and continued to stroke his nine inch penis.
That is when my life changed forever, I do not know what happened or what came over me, but out of the blue my hand reached over to Stephens and joined him in stroking his penis. This stayed for another minute or so before Stephen pulled his hand away leaving mine as the only one stroking his penis.
"Wow that feels so good... I have never done this before" Stephen said.
"Me neither" I responded not once taking my eyes of Stephens penis. This felt so weird he was like a second father to me and I was stroking his penis.
"Maybe we should stop" Stephen said "This has got to be wrong" he continued while taking deeper breaths.
"We could" I said and just as I was about to stop something inside me clicked, and I was full of lust. I am not sure whether it was because it was Stephen and the pure fact that in a way it was like i****t (a topic that had always turned me on when reading online but never really thought about it), or the fact I was stroking a man's penis.
It was at that point that the words slipped out of my mouth, the words that would change my life forever and give me my first sexual experience with a male.
"But I don't want to"
As my head lowered to the tip of Stephens's penis where I kissed it gently, still stroking it with my hand I heard Stephen moan. I then started to lick the penis up and down the entire length covering his entire penis with my saliva.
Then just as I saw on the DVD I positioned my head above Stephens penis and lowered my lips beyond the tip of Stephens penis taking as much of it as I could and slowly bobbed my head, I could feel Stephen pushing his penis deeper and deeper into my mouth.
Our strokes began to become united, as my head went down his penis came up and within a couple of minutes of doing this Stephen grabbed the back of my head and pushed his penis as deep into my mouth as he could as he blew wad after wad of cum into my throat – I gagged as an immediate reaction and then attempted to swallow as much as I could like numerous girlfriends of mine had done in the past – before letting his penis slip from my mouth.
I stood up and raced to the bathroom to brush my teeth, it was not the best taste in the world. While brushing I saw Stephen standing behind me.
"You okay?" he asked me.
"Yeah just didn't expect to do that, and never thought I would do it" I replied blushing a little.
"If it is any consolation you were great" he replied.
"I am going to have a shower and jump into bed – do you want to join me?" he offered.
"Oh... um... no thanks I better get back to the room before Scott gets up" I answered thinking of the first excuse I could.
"Fair enough – Good night then" Stephen said as he went to his bedroom.
I raced back to Scotts' room, he was still asleep. I couldn't sleep so I packed my things and the moment the sun started to raise I left a note for Scott explaining I had to leave as I had work that day – an obvious lie but I needed to get out of there – and quickly left the house and drove home.
Upon getting home many thoughts were running through my head, did this make me gay? Would I do it again? But the most important question was whether I liked it?
Chapter Two:-
Chance Meeting
I had avoided speaking to Scott for a couple days while I cleared my head about what had happened with his father Stephen over the weekend. I had used the excuse that I had been working a lot and just had no time to meet up with him.
But I knew time was running out it was Scott's birthday this weekend and he was having a party at Stephens' house, so it was decision time for me – was I going to continue this life of "sin"?
I needed time to think about it, and I had done a lot of thinking over the last couple of days and to help take my mind of things I decided I would go out and buy Scott his birthday present.
About fifteen minutes later I was walking around the store shopping, I had already brought him a watch, and thought I would continue the long standing tradition we have which is buy each other a joke gift.
I made my way down the road to the Adult Store and went inside looking for a gift which would make people laugh at during the party.
I was browsing the shelves and saw a DVD that caught my attention – it was in fact the same DVD I had watched a couple days earlier with Stephen which led to my first sexual encounter with another man.
Adding it to my basket for my own personal use I continued to browse for the perfect gift. I stumbled across the female accessory aisle and found a giant black dildo, about the size of Stephens' nine inch penis.
I laughed and thought it would be fantastic; I raced to the checkout paid for the items and put the paper brown bag into the trunk of my car and headed home.
After arriving home I went to the trunk of my car and got my shopping out, just as I was closing the trunk Stephens' car pulled into my driveway and my best friends dad jumped out with a large grin on his face.
"Busted" he said laughing.
Baffled I looked at him confused.
"I saw you shopping, I was in the store and came out just as you were leaving so followed you here." Stephen said with a grin on his face.
"Oh yeah just shopping for Scott's present" I said playing it down.
"Want to show me what you got so we don't get him the same thing" Stephen asked.
"Sure, let's go inside and get a cold drink while we look" I said and led Stephen inside.
With Stephen sitting on my couch I retrieved the cold drinks and handed one to Stephen. I showed him the watch I brought his son.
"We have to talk about the other night" Stephen said to me, interrupting me showing him everything.
"What about it?" I asked acting dumb.
"About what we did and what the future holds" Stephen said with a smirk.
I was confused about what direction this discussion was taking.
"I liked it and want to do it again" Stephen said standing up from the couch, his jean shorts already unbuttoned meaning as he did so his pants dropped to the ground, with no boxer shorts on his penis sprung to life.
"Stephen, I don't know if we should" I said trying to calm things down.
"I think we should" he said as he walked towards me and pushed his lips onto mine. I resisted for a moment and then made the decision to continue the way life had been and gave in to the kiss.
While our tongues darted into each other's mouth Stephens hands slipped down to my own shorts, dropping them and my boxer shorts to the ground he started wanking me by stroking my penis in its semi-hard position until it was rock hard.
Once it was rock hard Stephen broke our kiss and dropped to his knees, he licked the tip of my cock before taking all seven and a half inches into his mouth and bobbing his head furiously. I started to meet each of his bops by moving my hips forward, thus thrusting my penis deeper into his mouth – on an occasion or two he gagged, further showing that he was not use to this, I was growing ever so closer to blowing my load and remembered how he made me swallow as much of his cum as possible.
As I edged closer to blowing my load I knew that I was just a few pumps away. I grabbed the back of Stephens head and pulled his head as far towards me as possible before wad after wad of hot sticky cum shot into the back of Stephens throat – when the first wave hit he opened his eyes wide, as if in horror, and in some small way this turned me on further.
As my penis began to go limp Stephen licked my cock clean before getting from his knees saying "Geez that was nice".
As I dropped to my knees Stephen stopped me picking me back up and said "How about we just sit around and talk for a while"
I agreed and refreshed our cold drinks; it was then that I found Stephen had lied to me. While talking Stephen let it slip that he had been with a guy before.
When probed deeper it became apparent that Stephen and Louise while married were quiet the kinky couple, they had done many things I had only read about however one thing was having a threesome where it was two guys and Louise, Stephens ex-wife and my best friend's mother.
Apparently they had done it on plenty of occasions and Louise had loved it and eventually fell in love with Clint, the other male involved.
I could tell that by speaking of it Stephen had let himself get a little down and so to cheer him up I walked to the brown paper bag which inside had the DVD I had watched at his place and Scotts' "joke" gift a black dildo.
Stephens eyes lit up as he walked towards me looking at it, he took it from my hands and studied it.
"Bend over boy" he said laughing – it was good to see him laugh, but was he being serious.
"Oh I think it's a little too big" I said joking back to him.
"No it is about right" he said holding it next to his own rock hard penis. How was I going to get out of this I wondered to myself?
He walked up to me and kissed me passionately, I was lost in lust once again as he slowly walked me backwards to the breakfast counter. Once there I could feel him fidgeting with something.
After about a minute he spun me around and I felt something wet go against my anus, now that I was facing the breakfast bench I could see that the butter I had just brought was open.
I felt the tip of a penis at my rear entrance.
"Stephen I don't know" I said hesitating, however it didn't have much success I felt the tip of a penis enter my anus – I was confused as to whether it was the dildo or Stephens very own penis.
Slowly the penis entered me, little by little, a gasp escaped from my lips as the pain became too much. Stephen began to slow down and allowed my now stretched asshole time to recover from the intruder before adding more of the shaft inside me.
I began to enjoy the feeling, but still wondered if it was the dildo or Stephen; my thoughts were abruptly brought to a halt when the penis in my rectum pushed in as far as it could go – a yelp coming from my lips.
Within seconds of the yelp escaping the dildo was placed at the entrance of my mouth and I opened wide as Stephen entered it in and told me to suck it like it was his.
The pace of the penis pumping behind me picked up some speed, as I continued to suck on the pretend penis in my mouth.
"Oh yes, you like that don't you my little slut" Stephen said while pumping my previously virgin asshole.
"mmmmm" was all I could reply as the dildo in my mouth continued to fill it.
"You're my fucken cock slut aren't you" Stephen said – his dirty talk turning me on more.
"mmmmpppphhhh" I managed again.
The pace from Stephen behind me picked up and I could tell he was close to cumming, he slipped out of my ass with a pop and ordered me to turn around and drop to my knees.
I did as I was told and within moments of me dropping to my knees and opening my mouth to suck him, as I thought he wanted, he slapped his penis against the side of my face and as I turned to try and get the penis his warm cum started spurting all over my face, in my hair, in my eyes and in my mouth.
Not being able to see anything I was unable to tell when or even if Stephen had finished cumming, my question was once again answered when Stephen slowly placed his penis in my mouth pushing the cum that was already in there down my throat – I gagged a little but managed to swallow.
Stephen then pulled his penis out and disappeared only to return a short time later with a towel to clean my face off so I could see again.
"Does this mean you have made a decision" Stephen said with a look on his face telling me he already knew the answer.
"I guess it does" I told him, standing to kiss him again.
"How was that" he asked me.
"It hurt a little at first but it was great having both my holes filled" I said with a giggle.
"That's it your my little slut now, and will do anything I say wont you." Stephen said this time looking at me with a stern look.
"Off course I will" I replied, hungry for penis now that I had made my decision.
Scotts' party went off without a hitch; once again I stayed over as was normal and made a quick visit to Stephen to give him a blow job while Scott had his shower.
Chapter Three:
What the hell is this?
Stephen called me on the phone about two weeks after Scotts' party, however I was at work and not able to take the call – however his message left on my answer phone alone was enough to turn me on, and make me curious.
"Hey it's Stephen, Look I have to go out this weekend to a business meeting out of town – would love it if you could come. I need to ask you a favour – it is a dress up event so pack something nice and I would owe you forever. Bye" was the simple message left by Stephen.
Stephen turned up to my house at about 5pm on the Friday afternoon, I went out and hoped into his car as we began our two hour journey to Camden, we both made small talk along the way until we hit the city limits of Camden.
"Did you bring things to dress up in?" Stephen asked me.
"Yeah I brought a nice shirt and my nice pair of jeans" I responded.
Stephen just laughed and pulled into the next shopping mall that we came across.
"What are we doing" I asked Stephen.
"I meant dress up, as in you dressing as a female" Stephen replied.
I was shocked I had never done it before, and had never even thought about it. I was hesitant to follow Stephen as he started shopping.
We went into an adult store, inside he found a short tartan skirt – which looked a lot like a school uniform skirt, and he picked up a white blouse, some tape, and some fishnet stockings.
We walked into the next store where he picked up a packet of condoms, and a yard glass. And in the final store we visited he brought a wig, and high-heeled shoes.
After returning to the car I voiced my concerns with Stephen who reassured me by saying:
"It's ok, tonight is a very important business meeting but for some reasons they only do business with those in a committed relationship or even better married. I just need you to dress up for no more than an hour and you will be rewarded for the rest of the weekend"
Thinking about it I thought an hour wouldn't be too bad, but I don't think I can pull off being a female.
We hit the hotel and made our way to the room that was pre-booked waiting for our arrival.
Inside the room Stephen and I had a shower where Stephen shaved every single part of my body, and upon getting out he lathered my body with soothing cream and moisturizer before slowly getting me ready.
First a black bra and matching panties, then the fishnet stockings, the skirt, the blouse, the wig and makeup and then finally my heels – the transformation was complete.
"You need to be flirty but not too flirty, they need to like you and believe that you are a female. My livelihood depends on it." Stephen said to me.
The meeting was a drinks at the bar sort of meeting, and from our hotel room we made our way to the elevator and down to the bar.
Outside the bar Stephen gave me a kiss on the cheek, and opened the doors for me to enter. I walked in an almost every head in the bar turned to look at me. Stephen led me to a booth where three other guys were sitting.
He shook each of their hands and introduced me as "Cindy – his partner" they all welcomed me and we sat down while they started to talk business, Stephen motioned to me that the man in the middle sitting opposite me was the one in charge.
Taking what he said earlier into account I reached across with my foot and started to stroke his leg up and down, he looked down and saw my foot before looking across the table at me. Upon making eye contact I winked at him and he smiled.
I allowed my foot to rise higher and higher up his leg and into his thigh; he spread his legs apart slightly so I could get my foot towards his penis where I rubbed it gently before letting my foot drop back to the floor.
I excused myself and made my way to the woman's' rest room, inside I began to check my make up and make sure that I still looked feminine, the door behind me opened and in walked what was hopefully Stephens next boss.
"Cindy" he said with a bright sparkle in his eye.
He came up behind me and pushed me so I was bent over the basin. He raised my skirt and started rubbing his hands all over my ass.
"Please no" I said, I wanted to be with Stephen and didn't want anything to come between that.
With some further resistance Craig finally got the point and let my skirt drop back to where it was.
"If he doesn't treat you right Cindy you give me a call – I could do with someone like you in my corner" he said with a wink as he left.
I quickly made my way back to the booth to be near the safe arms of Stephen who told me the good news that he had been hired, he had organised for us to all go back to our hotel room to celebrate.
A little reluctant I made my way with the four guys upstairs to our hotel room where we were going to have a number of drinks to celebrate Stephens new job.
The guys entered the room first and held the door open for me. I thanked them as I entered the room.
Stephen poured everyone a drink of vodka, were all cheered by clinking our glasses together and then downing the alcoholic beverage. The celebrations went on for a number of hours and everyone was starting to feel tipsy.
We were all drinking, dancing, and laughing having a good time – someone lit a joint and we all passed that around taking a hit then passing it on.
While dancing Stephen came over to me and whispered in my ear "Craig wants to fuck you", I looked at him astonished.
"It's ok, he will be gentle" Stephen said giving me a reassuring look. I trusted Stephen and did promise I would do anything for him – so I agreed to it.
I walked over to Craig and took him by the hand, leading him to the one bed and pushing him back until he fell onto the bed. Once resting on his arms I dropped down to my knees, fidgeted with his pants and pulled them off, exposing his penis – which was about 8 inches.
I looked him in the eye as I lowered my lipstick covered lips to the tip of his penis, kissing it, taking just the tip into my mouth; I removed the tip and held his penis with one hand slowly stroking it while licking the under-side of his shaft.
Once his penis was fully covered with my saliva I once again took the tip of his penis in my mouth again and slowly started to take it further and deeper into my mouth, and further down my throat.
Craig and I got into a decent rhythm, and ecstasy was taking over my body and I loved the feel of cock in my mouth, the lust was a dangerous thing. It was at that time that I felt a hand pull up my skirt and start rubbing my ass through the stockings.
It was a great feeling and I started to push back against the hand, and the stockings started to get pulled down and I tried to say something – despite Craig's' penis being in my mouth – when Stephen whispered in my ear.
"It's okay, they know"
This settled me down and the stockings were pulled down to my ankles and I could feel hands exploring every part of my body, rubbing up and down my legs to my ankles, then back up this time on the other side feeling the inside of my leg, cupping my ball sack before taking hold of my penis and slowly stroking it.
While I continued to suck Craig's' penis, I felt liquid being spread on my asshole with finger slowly spreading my cheeks apart and a finger pushing against the hole before entering it and slowly being pushed deeper and deeper before a second and third.
The fingers were then removed and replaced with a penis at the entry point to my hole. It slowly pushed against the entry and within a short period it was in my hole entering me further and further.
I continued to suck Craig's cock, while another man was fucking me by behind and building up steam; it was then that I felt a warm mouth go over my rock hard penis.
This foursome continued for quite a while – every time one was close to blowing Stephen would run to them with a yard glass and asking them to blow into that, after a short break they would be rock hard again at the sight of what was happening in the room and would swap positions with one of the other men.
After about an hour and a half of continued fucking and sucking everyone knew that fatigue was setting in, I felt the current man in my ass hole pull out and could hear him squirting into the yard glass.
He was replaced in my red-sore asshole by a cock that felt familiar; it was rock hard and closer to nine or ten inches big – the biggest of the night so far. It entered into my truly stretched asshole and I felt him lean over as far as he could – I could feel the man close to my ear, it was Stephen.
"We are almost done, I am going to get them to blow their last loads over you okay" he said, I nodded in approval.
He then shared his idea with everyone else who all agreed.
Stephen pulled out of my asshole, at the same time the guy who was fucking my mouth and told me to turn around.
As I turned around Stephen yelled to me to open my mouth, which I did, he then blew his latest load on my face, in my eyes, nose and into my mouth, the others quickly followed suit before I knew it my entire face was covered with cum.
I couldn't see through all the cum that had been shot over my eyes, all I could hear was everyone cheering.
"Open your mouth and tilt your head back slut" I heard Craig say.
I did as I was told and felt a force of liquid coming down my throat, as if being dropped from a height. I tried to swallow and that is when I realized that they were holding the Yard Glass above my head and tipping it into my mouth.
I spluttered a couple of times as my mouth became too full, the cum was over flowing from my mouth and down my chin onto my bare breasts and even down to my penis.
Once done someone threw a towel onto my face saying:
"Clean yourself up bitch"
As I wiped my face and chin I felt a mouth go around my penis and start sucking me close to orgasm, at the same time licking up the cum that had overflowed from my mouth, once I could see again I looked down to see one of the associates I didn't know the name off sucking me off – after all of the lust that had built up I came.
"Wow so just like my other slut you like Clint as well do you" Stephen said to me acknowledging Clint, was this the same Clint that ended his marriage?
I stood up and went to the bathroom to clean myself up. Upon returning Craig handed me a handful of notes, and a Dvd saying:
"Thanks for doing business with us; this is your copy of the movie we just made"
I was shocked – "Movie we just made" I screamed.
"Oh yeah, sorry these guys make amateur videos to sell. You also get a cut of all proceeds it makes" Stephen said as the others shook his hand and one by one left the room.
Growing up at school I was far from a "chick magnet" however had my fair share of summer romances, one night stands and semi-serious relationships – however it wasn't until I turned 19 that my life changed forever and turned me into the type of person I am today.
My best friend Scott and I had known each other since we were about three or four and went to pre-school together, Scott was slightly shorter than me about six foot but everything else about him was almost identical to me.
Our families had grown close together over the years as we became best of friends, we would spend nights and even whole weekends staying at each other's house, Christmas normally saw our families getting together on Christmas morning to have breakfast – in a way it was one big extended family.
One Saturday, shortly after my 19th birthday Scott and I made the trek to the local sports oval where we were players on the football team and took part in our match, after we headed back to Scott's house where we were going to prepare for a night of drinking.
Scott had recently moved back in with his father Stephen after his mother Louise had left Stephen after 22 years of marriage to be with another man, Scott's father was not coping that well and so to look after him Scott had moved back in.
After a number of quiet drinks at home Scott and I decided that we wouldn't head out to a night on the town clubbing, both of our bodies were aching after a hard fought football match earlier in the day and instead opted to have showers, and watch a couple movies in his room falling asleep whenever we wanted.
After watching the first movie the second one started and I dozed off to sleep, awaking several hours later with the desperate need to go to the bathroom to relieve myself – emptying the tank from the beers we had had earlier in the night.
On the way to the bathroom I saw that the lounge room light was off, however there was a blue and white flicker meaning that something was on the television.
After washing my hands I made my way to the lounge room – I walked quietly in case Stephen had fallen asleep, I didn't want to wake him.
As I got to the opening in the wall to head into the lounge room I poked my head around and looked at the television to my astonishment on the screen was a pornographic movie, it had one blonde female getting pumped by two penis' one entering her ass, the other filling her mouth.
I looked down at Stephen who was laying on his back on the couch, it took a couple moments for my eyes to adjust properly and when they did I realized Stephen had his penis hanging out of his pants and he was stroking a penis that looked to be about 9 inches.
Out of the blue, and catching me by surprise, Stephen looked at me – I later found out that I had gasped and he had heard – as he looked at me and realized who I was he quickly stuffed his penis back into his pants and zipped up once again, clicking stop on the DVD player at the same time bringing the movie to a screeching halt.
"I... I... I'm so sorry" I stammered as Stephen looked at me with a blank look.
"No need to apologize at all" Stephen said. "Come join me" he said patting the couch seat next to him.
I stopped and thought about it for a second, I was never interested in seeing guys masturbate, I didn't want to be around it and had no interest in all... however this was Stephen, there was beer on offer and I wanted to see what happened with the DVD on the screen – I had seen many of DVDs from Stephens collection while growing up but had never seen this one.
"Only if one of those beers is for me" I said after taking a deep breath and pointing to one of two full cans of beer on the coffee table.
"Off course one of them are" Stephen said. "Anything that is mine is yours after all, you should know that by now" Stephen said picking up one of the cans and handing it over to me.
I took the beer and sat on the couch next to Stephen popping the tab of the beer and taking a mouthful as Stephen picked up the remote and pressed play to kick the DVD back into action as the ladies muffled moans filled the room.
It didn't take long before I began to grow hard with what was happening on the screen, and a quick glance over to Stephen told me he was horny as well if the tent in his pants was anything to go by.
A short time later the scene of the DVD came to an end and another one was about to begin, Stephen stood up from the couch and started walking out of the room.
"I am getting another beer, you want one" he asked as he walked past me facing the television.
"Sure" I said as he exited.
The scene that started on the DVD shocked me. As it started it had two guys laying on the bed kissing, one then pushed the other flat on his back and kissed his way down his body to his penis where he started kissing it, licking it before taking it into his mouth sucking it.
For some reason my penis responded to what I was seeing on the television screen as Stephen came back into the room carrying the beers handing one to me.
He sat on the couch next to me once again and our focus turned back to the television screen. A couple minutes passed and I saw Stephen fidgeting out of the corner of my eye, I glanced over at him and he had once again pulled his penis out of his pants and was stroking it once again.
I was fixated on the size of it; it looked to grow bigger with each and every stroke he made.
"Do you want to touch it" Stephen said almost laughing as he said it, snapping me out of my thoughts. I quickly glanced back to the television screen as thoughts flooded my mind, did I want to touch it? Would it make me gay? I was confused.
Stephen had thought I had gone shy and looked back at the movie showing on the television and continued to stroke his nine inch penis.
That is when my life changed forever, I do not know what happened or what came over me, but out of the blue my hand reached over to Stephens and joined him in stroking his penis. This stayed for another minute or so before Stephen pulled his hand away leaving mine as the only one stroking his penis.
"Wow that feels so good... I have never done this before" Stephen said.
"Me neither" I responded not once taking my eyes of Stephens penis. This felt so weird he was like a second father to me and I was stroking his penis.
"Maybe we should stop" Stephen said "This has got to be wrong" he continued while taking deeper breaths.
"We could" I said and just as I was about to stop something inside me clicked, and I was full of lust. I am not sure whether it was because it was Stephen and the pure fact that in a way it was like i****t (a topic that had always turned me on when reading online but never really thought about it), or the fact I was stroking a man's penis.
It was at that point that the words slipped out of my mouth, the words that would change my life forever and give me my first sexual experience with a male.
"But I don't want to"
As my head lowered to the tip of Stephens's penis where I kissed it gently, still stroking it with my hand I heard Stephen moan. I then started to lick the penis up and down the entire length covering his entire penis with my saliva.
Then just as I saw on the DVD I positioned my head above Stephens penis and lowered my lips beyond the tip of Stephens penis taking as much of it as I could and slowly bobbed my head, I could feel Stephen pushing his penis deeper and deeper into my mouth.
Our strokes began to become united, as my head went down his penis came up and within a couple of minutes of doing this Stephen grabbed the back of my head and pushed his penis as deep into my mouth as he could as he blew wad after wad of cum into my throat – I gagged as an immediate reaction and then attempted to swallow as much as I could like numerous girlfriends of mine had done in the past – before letting his penis slip from my mouth.
I stood up and raced to the bathroom to brush my teeth, it was not the best taste in the world. While brushing I saw Stephen standing behind me.
"You okay?" he asked me.
"Yeah just didn't expect to do that, and never thought I would do it" I replied blushing a little.
"If it is any consolation you were great" he replied.
"I am going to have a shower and jump into bed – do you want to join me?" he offered.
"Oh... um... no thanks I better get back to the room before Scott gets up" I answered thinking of the first excuse I could.
"Fair enough – Good night then" Stephen said as he went to his bedroom.
I raced back to Scotts' room, he was still asleep. I couldn't sleep so I packed my things and the moment the sun started to raise I left a note for Scott explaining I had to leave as I had work that day – an obvious lie but I needed to get out of there – and quickly left the house and drove home.
Upon getting home many thoughts were running through my head, did this make me gay? Would I do it again? But the most important question was whether I liked it?
Chapter Two:-
Chance Meeting
I had avoided speaking to Scott for a couple days while I cleared my head about what had happened with his father Stephen over the weekend. I had used the excuse that I had been working a lot and just had no time to meet up with him.
But I knew time was running out it was Scott's birthday this weekend and he was having a party at Stephens' house, so it was decision time for me – was I going to continue this life of "sin"?
I needed time to think about it, and I had done a lot of thinking over the last couple of days and to help take my mind of things I decided I would go out and buy Scott his birthday present.
About fifteen minutes later I was walking around the store shopping, I had already brought him a watch, and thought I would continue the long standing tradition we have which is buy each other a joke gift.
I made my way down the road to the Adult Store and went inside looking for a gift which would make people laugh at during the party.
I was browsing the shelves and saw a DVD that caught my attention – it was in fact the same DVD I had watched a couple days earlier with Stephen which led to my first sexual encounter with another man.
Adding it to my basket for my own personal use I continued to browse for the perfect gift. I stumbled across the female accessory aisle and found a giant black dildo, about the size of Stephens' nine inch penis.
I laughed and thought it would be fantastic; I raced to the checkout paid for the items and put the paper brown bag into the trunk of my car and headed home.
After arriving home I went to the trunk of my car and got my shopping out, just as I was closing the trunk Stephens' car pulled into my driveway and my best friends dad jumped out with a large grin on his face.
"Busted" he said laughing.
Baffled I looked at him confused.
"I saw you shopping, I was in the store and came out just as you were leaving so followed you here." Stephen said with a grin on his face.
"Oh yeah just shopping for Scott's present" I said playing it down.
"Want to show me what you got so we don't get him the same thing" Stephen asked.
"Sure, let's go inside and get a cold drink while we look" I said and led Stephen inside.
With Stephen sitting on my couch I retrieved the cold drinks and handed one to Stephen. I showed him the watch I brought his son.
"We have to talk about the other night" Stephen said to me, interrupting me showing him everything.
"What about it?" I asked acting dumb.
"About what we did and what the future holds" Stephen said with a smirk.
I was confused about what direction this discussion was taking.
"I liked it and want to do it again" Stephen said standing up from the couch, his jean shorts already unbuttoned meaning as he did so his pants dropped to the ground, with no boxer shorts on his penis sprung to life.
"Stephen, I don't know if we should" I said trying to calm things down.
"I think we should" he said as he walked towards me and pushed his lips onto mine. I resisted for a moment and then made the decision to continue the way life had been and gave in to the kiss.
While our tongues darted into each other's mouth Stephens hands slipped down to my own shorts, dropping them and my boxer shorts to the ground he started wanking me by stroking my penis in its semi-hard position until it was rock hard.
Once it was rock hard Stephen broke our kiss and dropped to his knees, he licked the tip of my cock before taking all seven and a half inches into his mouth and bobbing his head furiously. I started to meet each of his bops by moving my hips forward, thus thrusting my penis deeper into his mouth – on an occasion or two he gagged, further showing that he was not use to this, I was growing ever so closer to blowing my load and remembered how he made me swallow as much of his cum as possible.
As I edged closer to blowing my load I knew that I was just a few pumps away. I grabbed the back of Stephens head and pulled his head as far towards me as possible before wad after wad of hot sticky cum shot into the back of Stephens throat – when the first wave hit he opened his eyes wide, as if in horror, and in some small way this turned me on further.
As my penis began to go limp Stephen licked my cock clean before getting from his knees saying "Geez that was nice".
As I dropped to my knees Stephen stopped me picking me back up and said "How about we just sit around and talk for a while"
I agreed and refreshed our cold drinks; it was then that I found Stephen had lied to me. While talking Stephen let it slip that he had been with a guy before.
When probed deeper it became apparent that Stephen and Louise while married were quiet the kinky couple, they had done many things I had only read about however one thing was having a threesome where it was two guys and Louise, Stephens ex-wife and my best friend's mother.
Apparently they had done it on plenty of occasions and Louise had loved it and eventually fell in love with Clint, the other male involved.
I could tell that by speaking of it Stephen had let himself get a little down and so to cheer him up I walked to the brown paper bag which inside had the DVD I had watched at his place and Scotts' "joke" gift a black dildo.
Stephens eyes lit up as he walked towards me looking at it, he took it from my hands and studied it.
"Bend over boy" he said laughing – it was good to see him laugh, but was he being serious.
"Oh I think it's a little too big" I said joking back to him.
"No it is about right" he said holding it next to his own rock hard penis. How was I going to get out of this I wondered to myself?
He walked up to me and kissed me passionately, I was lost in lust once again as he slowly walked me backwards to the breakfast counter. Once there I could feel him fidgeting with something.
After about a minute he spun me around and I felt something wet go against my anus, now that I was facing the breakfast bench I could see that the butter I had just brought was open.
I felt the tip of a penis at my rear entrance.
"Stephen I don't know" I said hesitating, however it didn't have much success I felt the tip of a penis enter my anus – I was confused as to whether it was the dildo or Stephens very own penis.
Slowly the penis entered me, little by little, a gasp escaped from my lips as the pain became too much. Stephen began to slow down and allowed my now stretched asshole time to recover from the intruder before adding more of the shaft inside me.
I began to enjoy the feeling, but still wondered if it was the dildo or Stephen; my thoughts were abruptly brought to a halt when the penis in my rectum pushed in as far as it could go – a yelp coming from my lips.
Within seconds of the yelp escaping the dildo was placed at the entrance of my mouth and I opened wide as Stephen entered it in and told me to suck it like it was his.
The pace of the penis pumping behind me picked up some speed, as I continued to suck on the pretend penis in my mouth.
"Oh yes, you like that don't you my little slut" Stephen said while pumping my previously virgin asshole.
"mmmmm" was all I could reply as the dildo in my mouth continued to fill it.
"You're my fucken cock slut aren't you" Stephen said – his dirty talk turning me on more.
"mmmmpppphhhh" I managed again.
The pace from Stephen behind me picked up and I could tell he was close to cumming, he slipped out of my ass with a pop and ordered me to turn around and drop to my knees.
I did as I was told and within moments of me dropping to my knees and opening my mouth to suck him, as I thought he wanted, he slapped his penis against the side of my face and as I turned to try and get the penis his warm cum started spurting all over my face, in my hair, in my eyes and in my mouth.
Not being able to see anything I was unable to tell when or even if Stephen had finished cumming, my question was once again answered when Stephen slowly placed his penis in my mouth pushing the cum that was already in there down my throat – I gagged a little but managed to swallow.
Stephen then pulled his penis out and disappeared only to return a short time later with a towel to clean my face off so I could see again.
"Does this mean you have made a decision" Stephen said with a look on his face telling me he already knew the answer.
"I guess it does" I told him, standing to kiss him again.
"How was that" he asked me.
"It hurt a little at first but it was great having both my holes filled" I said with a giggle.
"That's it your my little slut now, and will do anything I say wont you." Stephen said this time looking at me with a stern look.
"Off course I will" I replied, hungry for penis now that I had made my decision.
Scotts' party went off without a hitch; once again I stayed over as was normal and made a quick visit to Stephen to give him a blow job while Scott had his shower.
Chapter Three:
What the hell is this?
Stephen called me on the phone about two weeks after Scotts' party, however I was at work and not able to take the call – however his message left on my answer phone alone was enough to turn me on, and make me curious.
"Hey it's Stephen, Look I have to go out this weekend to a business meeting out of town – would love it if you could come. I need to ask you a favour – it is a dress up event so pack something nice and I would owe you forever. Bye" was the simple message left by Stephen.
Stephen turned up to my house at about 5pm on the Friday afternoon, I went out and hoped into his car as we began our two hour journey to Camden, we both made small talk along the way until we hit the city limits of Camden.
"Did you bring things to dress up in?" Stephen asked me.
"Yeah I brought a nice shirt and my nice pair of jeans" I responded.
Stephen just laughed and pulled into the next shopping mall that we came across.
"What are we doing" I asked Stephen.
"I meant dress up, as in you dressing as a female" Stephen replied.
I was shocked I had never done it before, and had never even thought about it. I was hesitant to follow Stephen as he started shopping.
We went into an adult store, inside he found a short tartan skirt – which looked a lot like a school uniform skirt, and he picked up a white blouse, some tape, and some fishnet stockings.
We walked into the next store where he picked up a packet of condoms, and a yard glass. And in the final store we visited he brought a wig, and high-heeled shoes.
After returning to the car I voiced my concerns with Stephen who reassured me by saying:
"It's ok, tonight is a very important business meeting but for some reasons they only do business with those in a committed relationship or even better married. I just need you to dress up for no more than an hour and you will be rewarded for the rest of the weekend"
Thinking about it I thought an hour wouldn't be too bad, but I don't think I can pull off being a female.
We hit the hotel and made our way to the room that was pre-booked waiting for our arrival.
Inside the room Stephen and I had a shower where Stephen shaved every single part of my body, and upon getting out he lathered my body with soothing cream and moisturizer before slowly getting me ready.
First a black bra and matching panties, then the fishnet stockings, the skirt, the blouse, the wig and makeup and then finally my heels – the transformation was complete.
"You need to be flirty but not too flirty, they need to like you and believe that you are a female. My livelihood depends on it." Stephen said to me.
The meeting was a drinks at the bar sort of meeting, and from our hotel room we made our way to the elevator and down to the bar.
Outside the bar Stephen gave me a kiss on the cheek, and opened the doors for me to enter. I walked in an almost every head in the bar turned to look at me. Stephen led me to a booth where three other guys were sitting.
He shook each of their hands and introduced me as "Cindy – his partner" they all welcomed me and we sat down while they started to talk business, Stephen motioned to me that the man in the middle sitting opposite me was the one in charge.
Taking what he said earlier into account I reached across with my foot and started to stroke his leg up and down, he looked down and saw my foot before looking across the table at me. Upon making eye contact I winked at him and he smiled.
I allowed my foot to rise higher and higher up his leg and into his thigh; he spread his legs apart slightly so I could get my foot towards his penis where I rubbed it gently before letting my foot drop back to the floor.
I excused myself and made my way to the woman's' rest room, inside I began to check my make up and make sure that I still looked feminine, the door behind me opened and in walked what was hopefully Stephens next boss.
"Cindy" he said with a bright sparkle in his eye.
He came up behind me and pushed me so I was bent over the basin. He raised my skirt and started rubbing his hands all over my ass.
"Please no" I said, I wanted to be with Stephen and didn't want anything to come between that.
With some further resistance Craig finally got the point and let my skirt drop back to where it was.
"If he doesn't treat you right Cindy you give me a call – I could do with someone like you in my corner" he said with a wink as he left.
I quickly made my way back to the booth to be near the safe arms of Stephen who told me the good news that he had been hired, he had organised for us to all go back to our hotel room to celebrate.
A little reluctant I made my way with the four guys upstairs to our hotel room where we were going to have a number of drinks to celebrate Stephens new job.
The guys entered the room first and held the door open for me. I thanked them as I entered the room.
Stephen poured everyone a drink of vodka, were all cheered by clinking our glasses together and then downing the alcoholic beverage. The celebrations went on for a number of hours and everyone was starting to feel tipsy.
We were all drinking, dancing, and laughing having a good time – someone lit a joint and we all passed that around taking a hit then passing it on.
While dancing Stephen came over to me and whispered in my ear "Craig wants to fuck you", I looked at him astonished.
"It's ok, he will be gentle" Stephen said giving me a reassuring look. I trusted Stephen and did promise I would do anything for him – so I agreed to it.
I walked over to Craig and took him by the hand, leading him to the one bed and pushing him back until he fell onto the bed. Once resting on his arms I dropped down to my knees, fidgeted with his pants and pulled them off, exposing his penis – which was about 8 inches.
I looked him in the eye as I lowered my lipstick covered lips to the tip of his penis, kissing it, taking just the tip into my mouth; I removed the tip and held his penis with one hand slowly stroking it while licking the under-side of his shaft.
Once his penis was fully covered with my saliva I once again took the tip of his penis in my mouth again and slowly started to take it further and deeper into my mouth, and further down my throat.
Craig and I got into a decent rhythm, and ecstasy was taking over my body and I loved the feel of cock in my mouth, the lust was a dangerous thing. It was at that time that I felt a hand pull up my skirt and start rubbing my ass through the stockings.
It was a great feeling and I started to push back against the hand, and the stockings started to get pulled down and I tried to say something – despite Craig's' penis being in my mouth – when Stephen whispered in my ear.
"It's okay, they know"
This settled me down and the stockings were pulled down to my ankles and I could feel hands exploring every part of my body, rubbing up and down my legs to my ankles, then back up this time on the other side feeling the inside of my leg, cupping my ball sack before taking hold of my penis and slowly stroking it.
While I continued to suck Craig's' penis, I felt liquid being spread on my asshole with finger slowly spreading my cheeks apart and a finger pushing against the hole before entering it and slowly being pushed deeper and deeper before a second and third.
The fingers were then removed and replaced with a penis at the entry point to my hole. It slowly pushed against the entry and within a short period it was in my hole entering me further and further.
I continued to suck Craig's cock, while another man was fucking me by behind and building up steam; it was then that I felt a warm mouth go over my rock hard penis.
This foursome continued for quite a while – every time one was close to blowing Stephen would run to them with a yard glass and asking them to blow into that, after a short break they would be rock hard again at the sight of what was happening in the room and would swap positions with one of the other men.
After about an hour and a half of continued fucking and sucking everyone knew that fatigue was setting in, I felt the current man in my ass hole pull out and could hear him squirting into the yard glass.
He was replaced in my red-sore asshole by a cock that felt familiar; it was rock hard and closer to nine or ten inches big – the biggest of the night so far. It entered into my truly stretched asshole and I felt him lean over as far as he could – I could feel the man close to my ear, it was Stephen.
"We are almost done, I am going to get them to blow their last loads over you okay" he said, I nodded in approval.
He then shared his idea with everyone else who all agreed.
Stephen pulled out of my asshole, at the same time the guy who was fucking my mouth and told me to turn around.
As I turned around Stephen yelled to me to open my mouth, which I did, he then blew his latest load on my face, in my eyes, nose and into my mouth, the others quickly followed suit before I knew it my entire face was covered with cum.
I couldn't see through all the cum that had been shot over my eyes, all I could hear was everyone cheering.
"Open your mouth and tilt your head back slut" I heard Craig say.
I did as I was told and felt a force of liquid coming down my throat, as if being dropped from a height. I tried to swallow and that is when I realized that they were holding the Yard Glass above my head and tipping it into my mouth.
I spluttered a couple of times as my mouth became too full, the cum was over flowing from my mouth and down my chin onto my bare breasts and even down to my penis.
Once done someone threw a towel onto my face saying:
"Clean yourself up bitch"
As I wiped my face and chin I felt a mouth go around my penis and start sucking me close to orgasm, at the same time licking up the cum that had overflowed from my mouth, once I could see again I looked down to see one of the associates I didn't know the name off sucking me off – after all of the lust that had built up I came.
"Wow so just like my other slut you like Clint as well do you" Stephen said to me acknowledging Clint, was this the same Clint that ended his marriage?
I stood up and went to the bathroom to clean myself up. Upon returning Craig handed me a handful of notes, and a Dvd saying:
"Thanks for doing business with us; this is your copy of the movie we just made"
I was shocked – "Movie we just made" I screamed.
"Oh yeah, sorry these guys make amateur videos to sell. You also get a cut of all proceeds it makes" Stephen said as the others shook his hand and one by one left the room.
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