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.
If you or someone you know has been with Tess, please email me at twonight@excite.com and tell me about it. I am very interested to compare your account with her journal entries.
Check out my fiction stories too (The Awakening, Black Dorm, Star Cruiser, and Olympiad), and my own true story (Shocking Encounter).