Foreword
About two months ago, I was in Miami on business and I went to a club in
South Beach that caters to a gay clientele. While there, I met a gorgeous
shemale named Tess and her friends Maddie (shemale) and Sam (bisexual guy).
We danced a few times and she invited me to join them back at her place. I
was surprised to see that she was driving a Jaguar convertible. I had come
in a cab so I drove Tess' Jag with her in the passenger seat (for a while
at least) and Maddie and Sam followed. I will save the story about that
night for the end of this long tale. I discovered that Tess was a very
wealthy lady who lived to have fun (and sex) with friends (a lot of
friends). I also discovered that she had been keeping a detailed journal
since her /his early teens and she had been toying with the idea of putting
it into a biography. The problem was that she didn't want to devote the
time to do the job herself. After reading a bit of the journal, I quickly
offered to do the job for her on two conditions - one, that I could put it
on Nifty and two, that I could hang out with her and her friends for a few
days. Those few days were incredible. They would have made Caligula
blush. During the day I wrote and at night she gave me more to write
about.
So without further ado, here is Tess' story from her perspective, captured
from her journals. I can't vouch for its authenticity (except for the
parts where I was a participant), but I believe that it is true.
World's Hottest T-Girl - Part 1
Intro
My name is Tess and I am a pre-operative transsexual, although I have had
breast implants. I am 25 and live in Miami in the South Beach area in a
beautiful two-story house with a view of the water. I have a very active
sex life with numerous friends of all sexes and sexual orientations. I am
a big fan of group sex and public sex, although I enjoy almost any form of
sex (except pain and watersports). Because I have been sexually active
since age 14 and have had a very colorful sex life, I have had numerous
requests to write my sexual memoirs. I've kept a journal since I was 13,
so I have most of my encounters documented. I had been hesitant to do so
until I started visiting the sex chatrooms. I found that I enjoy having
sex while chatting and my friends like it too. I also started getting
suggestions from people in the chatrooms to write my story (for their lewd
entertainment, I'm sure). So by popular demand, here are my sexual memoirs
(to-date). I have changed some of the names to protect the innocent (and
guilty) and have left out many encounters that were either too painful or
not particularly interesting. My co-author in this endeavor is using
detailed accounts from my journals to create a story told in first-person
form.
The Beginning
I was born in Miami to a Portuguese father and a blond-haired American
woman who named me David. We moved to Brazil when I was 3 and returned
when I was 5. I learned almost no Portuguese, but did pick up some Spanish
("Tu pene es en mi culo."). I had kind of an exotic look with blonde hair
and slightly Latin features. When I was 13, I began to notice that I was
attracted to both men and women. At that age, I didn't know that bisexuals
or transsexuals (I prefer tgirl) even existed.
My uncle Hal and I were both into golf at that time and he took me to play
at a private club where he was a member. We played every Saturday morning.
Hal was a very handsome, well-built guy (6', 185 lbs., muscular). My
interest in golf was probably due, in part, to my attraction to Uncle Hal.
After we had been playing a while, I began to sneak glances at his naked
body in the shower and locker area. His penis was not huge, but probably a
little above average. Mine was actually 7 inches long at that point (now
about 8") and it started to harden every time I looked at his firm ass.
One day, I was rather blatantly staring at his cock, when I realized he had
caught me. He laughed when he saw my half-hard cock but didn't say
anything, just chuckled and turned away. At that point, I wasn't sure that
he had noticed. On the way home, he didn't say much at first. Then,
finally, he asked "Did you like what you saw back there?" I pretended not
to understand so he said "It's OK, I liked it too." My heart almost jumped
out of my chest. I couldn't respond or even look at him.
"Would you like a closer look?" he asked.
"What do you mean?" I asked.
"I mean, would you like to touch it?"
"I'm not sure. Won't we get in trouble?"
"Are you going to tell anyone?"
"No."
"Neither will I."
He suggested we stop at a small motel on the way home so that I could get a
"better look" and I reluctantly (but happily) agreed. When we got inside,
he sat me on the bed and turned off all the lights except for the lamp by
the bed. He then asked me to do the honors. I nervously unzipped his
pants and pulled them off. His cock was standing at attention in his
briefs. My hands were shaking as I pulled off his briefs and freed his
stiff shaft from its prison. I couldn't resist putting my hand on the
shaft and Uncle Hal let out a soft moan. I wasn't sure what to do next,
but I did not want to stop.
Hal told me to stroke it like I would my own, so I wrapped my hand around
his thick shaft and began to move up and down. I continued the handjob for
a minute or two, then suggested he lay on the bed. I began to rub his
balls while I stroked his member and he moaned continuously. As I watched
my hand move on his cock, I had an overwhelming desire to have it in my
mouth like I'd seen a woman doing in a porno magazine at a friend's house.
I was afraid that he would object, but I just couldn't resist the urge.
I moved cautiously and licked the underside of the shaft. He groaned
loudly and said "Please suck my dick, David. Please don't tease me." That
was all the encouragement I needed and I wrapped my lips around the head.
He groaned even louder and raised his hips to push it in further. I got
the hint and took more of it in. At first my teeth got in the way, but I
figured out a way to avoid that and took even more in. I started to bob up
and down, milking his cock with my lips and tongue. He writhed on the bed
and kept telling me how great it felt. After a while, I decided to try to
take it all the way in. I pressed down and it hit the back of my mouth. I
gagged and backed off. Then I tried breathing out as I did it and it was
easier. After a few tries and a couple of gags, I took it all. Hal looked
like he was on another planet the way his eyes were bulging when I took it
all the way down.
He started to breathe quickly and his toes were flexing. I asked him if he
was close and he said he would warn me so I wouldn't get it in my mouth. I
had not considered what I would do with his cum. I was so focused on
sucking him well that I forgot about his load. I started bobbing all the
way up and all the way down, really stroking him with my tongue. Then I
took it all the way and stuck out my tongue to lick his big balls. For
some reason this made me feel so queer.
As he got closer, he began to raise his hips again and his breathing
quickened. He started to groan louder then yelled "Here it comes!" At
that moment, I made a decision that I have never regretted. I decided to
swallow his cum. As I continued to suck him, a blast of hot, sticky cum
hit my tonsils. It was exhilarating. I was so excited as more and more
cockjuice poured from his dickhead into my mouth. I will never forget how
great it tasted and I still love to eat a man's cum to this day.
When I finally gave his prick back to him, I had milked every drop from it
and he was ecstatic. He said that we were running late and had to go. He
wanted to know whether I would like to go further the next week. I quickly
said yes and he suggested that maybe this was a better way to spend a
Saturday morning than playing golf. I wholeheartedly agreed and he drove
me home.
I counted the days until our next session and finally it arrived. We went
straight to the motel and he brought in a small sack. I was intrigued but
didn't ask. He suggested that we start with another demonstration of my
oral skills and I was delighted to oblige. He came much quicker, thanks to
my newfound cocksucking talents and I swallowed again, letting a little run
down my chin. He shocked me by licking it off my face and swallowing it.
Next he started kissing me, putting his tongue in my mouth and undoing my
pants. After he got them off, he removed the briefs and started stroking
my cock. I was in heaven as he kissed me deeply and stroked me to a raging
hardon. Then he laid me back and swallowed my big dick in one motion. I
was so shocked and excited that I almost came right there. Fortunately, I
didn't because he gave me a magnificent blowjob. He had me close to coming
several times, then backed off.
Finally he reached in his sack and pulled out some lotion. He put some on
his fingers, then started sucking me again. Then I felt his finger against
my asshole. I started to panic, but he told me to calm down. He reminded
me that I had enjoyed everything else and he promised that this would be
great too. I decided to give it a chance and he put his finger against my
tight sphincter again.
When he finally penetrated me, I almost bucked his face off of my cock. He
stopped, but left the finger in. He started sucking my cock like there was
no tomorrow and I hardly noticed that he had pushed the rest of his finger
in. It felt strange, but nice. It hurt a little, but felt so sexy. Then
he started to move it in and out as he mouthed my hard member. Suddenly I
had to cum. I could not control it. The finger in my ass hit some button
and I just exploded without warning.
Hal may have been surprised, but he didn't miss a drop. He really gave me
the vacuum treatment and continued fingerfucking my tight ass. As I
recovered, I asked him if he had any more surprises for me. Boy, was I
na<ve. He told me to lie still and he inserted something bigger than a
finger in my ass. At that time, I didn't know what a buttplug was, but
this was my introduction. It hurt and felt good at the same time. I loved
the feeling of being filled. He eventually replaced the butt plug with a
six inch dildo and began to stroke my ass with it. It was so hot seeing him
fucking my ass with it in the mirror.
After I was loosened a bit, he made his move. I knew, by then, that I was
in for my first buttfucking and I was more than ready. He slipped on a
condom and lubed it good. Then, he put me on my knees and knelt behind me
to mount me. I have never been more excited than that. His cockhead
nudged at my asshole as he tried to gain entrance. He tried several times,
but the thick shaft wouldn't go in. Finally, he leaned over and stuck his
tongue right up my ass. It was unbelievable and he wiggled it around as he
moved in and out, tongue-fucking my tight, hot ass. After a little of
this, he moved back up and placed his cockhead against my sphincter. Then
he eased the head in about an inch. Pain shot through me coupled with
lust. I wanted to be fucked so desperately. I needed his cock in my ass.
He knew I was straining and he went slowly, an inch at a time, backing up
occasionally, then pushing again. When I felt his balls resting against
mine, I knew I had it all. He left it there for a while, leaning over and
rubbing my chest. I felt completely taken, like a woman taking her man's
big cock. He had mounted me and was about to ride my slutty ass.
He pulled halfway out, then pushed all the way back, continuing this rhythm
while my ass adjusted to his thickness, stretched wide by his girth. He
picked up the pace and reached around to stroke my cock, which had grown to
record proportions. He settled into a lovely rhythm, his cock sliding in
and out of my steamy ass and his hand stroking me to another orgasm.
After a few minutes of fucking, he pulled out and lay on his back. He told
me to straddle him and slide my ass down his cock. I followed instructions
and felt that wonderful feeling again as he filled the void in my ass. It
still hurt, but I was determined. I began to bounce up and down as we both
moaned loudly. He reached out and stroked my cock again and I decided that
I never wanted this to end. Finally he told me that he was going to cum
and I surprised him again by jumping off, stripping off the condom, and
burying his cock down my throat. He shot another huge load and I let a
little run down his cock so I could suck it up again.
After his spasms subsided, he laid me on my back and put a condom on me
with some lube. He then lubed his own ass and straddled me. With my lack
of experience, he didn't want me stabbing him with my big cock. He got the
head in, then put more weight on it and slid down the pole. It seemed like
every new sensation that day was better than the last. I was in heaven
again with my big slab of meat stretching his velvet ass. I didn't last
much longer and I shot a sizable load in the condom. He slid off me and
removed the rubber carefully. Then he stuck the open end in his mouth and
emptied my cum in his mouth. Finally, he leaned down and kissed me,
sharing my big load as we both swallowed cum. It was magic.
For the next two years we rarely missed a Saturday. We fucked each other
in every position possible, using tongues, cocks, toys, and anything that
would fit. My cock grew another inch, but Hal still took it all. It was
fabulous and I thank Uncle Hal every day for the education he gave me.
