A Trannys First Time

I began exploring my feminine side sexually about two years ago. I had been a
crossdresser for years and definitely bi curious but was always too inhibited to
live out my sexual fantasies. Until last year I rarely went out dressed up
unless it was Halloween or Mardi Gras. I had been told I was very passable (nice
legs and :lol: ) I met a t-girl named Celeste on line in a crossdressing/transgender forum. We chatted for hours over the course of several months and she finally convinced me to meet her in the city where she lives. Celeste does girly make overs for aspiring crossdressers and trannys. I had sent some of my pics and she said I had a nice look, but she could make me hot! I was convinced and agreed to meet
her.

I drove to xxxx and got a hotel room. I said that I would meet her in the hotel
lounge later that evening and see where things went. I was excited and nervous
at the same time. I laid out all of my makeup, wig, silicone breast forms,
lingerie, shoes and my outfit and gave myself a make over, first shaving my legs
smooth, then shaved and scrubbed my face, applied foundation and then make up. I had purchased a real cute shoulder length black wig that gave me bangs. I had
never seen Celeste before in person and wanted to look good for her. I wore a
black underwire push up bra to hold in my 40c's and matching black lace boy
shorts. A black garter belt to hold up my fishnet thigh highs and 4 inch black
pumps. I slipped on my leather mini skirt and a cute sleeveless black top that
was just tight enough. I looked in the mirror and was happy with my transformation.
I smiled and took a few deep breathes and
grabbed my key and headed out the door. I walked my girlie walk I had practiced so much and waited for the elevator. When the door opened two guys were there. They smiled at me, I
thought "I guess they didn't make me, or did they?" We arrived in the lobby and
they let me out first. I walked to the bar sat down and ordered a drink. It was
early, about 6:00 p.m. and the bar was nearly empty. The bartender was cute and
nice and brought me a Heineken. I sipped it and waited for Celeste to arrive.

In about 10 minutes a stunning Latina strutted into the bar. It was Celeste. I
had seen her pictures but they didn't do her justice. Celeste is 5'8" about a
size 4 with a very nice figure. Celeste had just completed breast augmentation
and electrolysis about a year earlier and looked every bit of a GG. We hugged
and kissed and sat and got to know each other. Once I felt comfortable that she
was legit I agreed to go to
her home salon and let her do her magic. It was
still early and she said she wanted to "make me more beautiful" then we would go
clubbing. I had just turned 43 but admit I look younger especially in my fem
mode. Celeste has a cool home that is very unique and artsy just like her. She
guided me to her spare bedroom and showed me a robe to slip into while she did
my makeover.

It took a few hours but after my nails, hair and make up was done she finally
let me look in the mirror. It was incredible! I was dumbfounded. Celeste had
made this ugly duckling into a beautiful swan :D by now it was about 10 p.m. she
smiled and looked at me "Are you ready to go have fun?" We had talked about sex
and she knew I was curious but had never had sex with a guy before. There were
lots of reasons, mostly my inhibitions and of course the fear of stds and hiv.

Celeste and I drove to a t-girl friendly dance club in her
convertible VW and
she told me about someone she wanted me to meet. They had been a couple once,
but now just "fuck buddies" she thought I would like him. We got to the club and
it was packed. Lots of gay guys and a fair share of t-girls and gg's. We got
drinks and mingled a bit. I was really enjoying my new look and wiggled my ass a
little as I walked around for effect. I danced with a few guys and someone who
may have been a t-girl or a gg. I wasn't sure and I didn't really care. When I
met Celeste at the bar she was with a really hot looking guy she introduced as
"Eric". "This is the guy I was telling you about," she said. Eric took my hand
gently. I tingled inside and blushed a bit. We went outside on the patio and
chatted for a while. Eric excused himself and left for the men's room. Celeste
wasted little time. "Isn't he hot?" I smiled and nodded. "Do you want to do
him?" I looked away and giggled.
"Maybe!" Celeste took my hand "Of course you
do, you are ready girl!" Wow, she called me girl. Eric returned and Celeste
said, "Let's move the party to my place. Eric followed us in his car.

Celeste told me we could do as much or as little as I wanted, it was all my
call. I asked "Did you tell him your plans?" "No of course not!" she replied but
he sort of knows and I could tell he likes you." "Really? I must be ten years
older than him." I said. "Nearly 15 years older, but that's cool, you're a hot
little cougar! and she winked at me. We got to Celeste's house and she poured us
a glass of wine as she handed me her glass she said follow my lead. Eric sat on
the couch and we sat of either side of him. I was so nervous I nearly couldn't
control myself, but I was excited too! Celeste reached over and unzipped Eric
trousers. I began to rub his thighs and could feel his balls sack through the
fabric.
Celeste tugged on his cock. It was incredible, maybe 8 inches and thick.
Celeste said "Melissa, why don't you give Eric a little strip show to get him in
the mood." I stood up and pulled off my top and then I wiggled out of my skirt.
I turned around and Celeste asked him, "Like what you see?" Eric nodded and
smiled at me. By then she had worked his pants off and he just sat on the couch
bare assed as she stroked his wonderful cock.

Even now over two years later I can't believe what I did next. Blame the wine or
Celeste's transformation of me into a t-girl. I got on my knees between Eric's
spread thighs and took his cock in my hands. It was hard and soft at the same
time, it felt like mine but different. I stroked it and leaned forward and
flicked my tongue along the head and then the shaft. Then I took as much of it
in my mouth as I could. I was so turned on. I couldn't believe I was finally
sucking a
cock. Celeste got off the couch and got undressed leavingon her
garter belt, hose and heels. I was still wearing my bra, panties, hose and
heels.

Celeste had a little digital camera in her hands and took pictures of me going
down on Eric. After about 10 minutes I could taste his pre-cum and knew he was
going to blow his load. I had tasted my own cum lots of times and was ready to
taste Eric's. Celeste had peeled off my panties and was working her fingers and
a butt plug into my ass. I had been diddling my ass for years with various
objects and toys and can cum from a hard dildo in my asshole. I thought she was
going to buttfuck me but she told me later she wanted Eric to have my ass first.
I looked up at him and told him to cum in my mouth when he was ready. I thought,
"Did I really just say that?" Eric didn't waste anytime and blew his load into
my mouth about a minute later. I gagged a little but I
managed to swallow all of
it."Wow!" I thought, I finally did it and it was great!" I've given head to a
lot other guys and t-girls since then, but I will never forget that night and
the sensation of his semen erupting into my mouth. Celeste pulled Eric off the
couch as I stayed on my knees sipping wine. Giving head makes me thirsty LOL!

Eric laid on his back on the carpet with his head on a pillow. Celeste told Eric
"This is a special occasion. It's Melissa's first time." I was a little
embarrassed but given the size of his cock I was glad that he knew. Celeste had
squirted a huge amount of Astroglide into my tush when she was playing with it
and now she was busy slipping a Trojan Magnum on his cock. I have a dildo about
the same size as Eric, but I knew the real thing was going to be different.
Celeste said, "Come on get over here! I can't keep him hard all night!" and
laughed. I straddled his narrow
waist and felt his ribs with my thighs. Celeste
took his shaft and gently pushed his cockhead against my pink asshole. "Melissa,
bare down on his cock like you are pooping, it will help relax your sphincter!"
I couldn't believe she just said that, but I did as I was told and Eric's cock
slipped painlessly into my bum. Celeste took a picture of me that I still have
the moment his cock went balls deep inside me. I have this big surprised look on
my face My ass relaxed and I began to rock up and down on him. I looked over
in the wall mirror was watched his cock disappear and reappear from my ass. I
really began to get into it, pissed I had waited until I was 43 to get fucked
but glad I finally did.

I got a little daring and climbed off Eric and asked "Wanna fuck me doggy?"
without a word his cock returned inside me. Celeste stuck her 6" cock in front
of me and I sucked on her. Celeste pulled her cock
out of my mouth and unwrapped a condom and slipped it on. Eric and she took turns doing my ass which was making something stir inside me. While one would fuck me I would stroke the
other to keep them hard so I could have more. Eric pumped me and and held my asscheeks tightly. My cock grew hard and without warning I shot my load all over
carpet. Eric didn't stop when I came and I nearly hyperventilated.
Celeste got behind him and tugged his balls. I finally felt his cock pulsate as
he shot his load into the condom. I was covered in sweat, my make up had run a
little but this was the most erotic experience I had ever had. Celeste pulled me
off the floor when Eric eased out of me and had me lean against her bar. The two
of us fucked standing until I begged her to come. My ass was more than a little
sore by now, but in a good way. I pulled away from her and got on my knees and
pulled the condom off her cock. I deep
throated her letting her shoot a stream
into my mouth. Celeste's cum tasted sweeter thanEric's. I opened wide and
showed off her pearly white jizz on my tongue before I swallowed it all. That
was over two years ago. Since then my new gender and sexual journey has
continues and I have no regrets.