Who, When, How........was your first time with a transsexual?

[MrsKellyPierce]

Who...
When...
Why....
How...

Were you addicted the first time..weirded out..

lmao the list goes on..do tell..

[luvblack77]

I believe I posted my story before, but I write it again for the benefit of all newcomers who may be unsure about themselves and their preferences.

I have a long story, and it took place in the late 70's. First I sould say I am a white male so readers better understand my story. I was leaving home for the first time to go to college in a different city. I arrived two days early and it was a holiday, so the college town was still empty. I stayed in a hotel by myself and had nothing to do in the evening. So I went looking for a book to read. Everything was closed that evening and right before I went back to the hotel, I saw a shop that said "books and magazines" open 24 hr. I was so naive, I thought it was a book store. I had never been to a porno shop before. So I was really surprised, excited and ashamed. I have always been attracted to black women and I quicky took 5 or 6 magazines showing black women on the cover, paid quicky without even looking at what I had bought and went back to the hotel. It was the first time I saw adult magazines and the excitment of actually seeing naked black women was intense.

I saw the magazines I had bought and to my surprise there was one featuring a black transsexual named Alexis. Imagine my surprise, I was looking at naked women for the first time and by mistake I had also bought what I considered a weird magazine. I put it away at first and only looked at the real girls. I masturbated for months with those magazines, but did not throw away the "strange stuff". Curiosity brought me to look at the odd magazine and as time went on, I found myself masturbating while looking at Alexis and dreaming about her. However, all my dates were strictly with women and never thought I would meet a tgirl.

Fast forward to my graduate student days in Boston in the mid 80s. I still preferred black women and saw a black woman prostitute now and then when I found one. No girlfriend yet. One evening I went with other students to a movie theater close to what was called "the combat zone". I saw from the theater that there was a bar nearby where a lot of working black girls seemed to go in and out. The following weekend I decided to go to that bar and take a look at the working girls. The name of the bar was "Jaque's". Unknown to me it was a meeting place for transsexual girls. I saw several beautiful girls and invited a particularly beautiful one to have a drink. Eventually we agreed to go to her apartment. She thought I knew, and I had no idea. She was passionate, and we started kissing. Boy, she smelled and tasted better than any girl I had met in my life. She started sucking me and it was heaven. I asked if she would 69, and she took her panties off. What a surprise. She had a very big black cock! I was shocked! Fortunately, Alexis had planted the seed of curiosity and instead of running away from the real tgirl in front of me, I started playing with her cock while I tried to figure out what to say or do. It was the best sex in my life. I put her cock in my mouth and it was not only exciting, it really tasted good. Then I topped her, the first time I had done someone in the ass. It was tight and the sensation was better than any gg pussy. Then, she surprised me when she started kissing my neck from behind, and started rubbing her dick against my ass. Before I knew it, she was inside of me. A weird mixture of pleasure and very strong pain turned into pure heavenly pleasure. She knew what she was doing. I was really excited and the strangest feeling grew from deep in my gut to the strongest orgasm of my life. I was screaming with pleasure. My orgasm ended but the pleasure continued on and on while she was making love to me. Finally she reached her climax. In those days before HIV, we did it without a condom and the feeling and intimacy of having her fill me with her love was amazing.

There was no U turn. After that experience, women seemed boring by comparison. I have no regrets. Transsexual girls are superior to women in every respect other than making babies.

[south ov da border]

I first got turned on to the idea of a trans woman at a young age. I hadn't seen one, but I liked the thought. Then as a teenager in the mid 90's I got a porn tape from a friend of mine that had those commercials with the 900 numbers on them. Well one had a brief video of a trans . And I must have re-wound that video 100 times that day. I was amazed. I lived in inner city Miami with my uber relgious family an being black and having these thoughts just was not going to fly. So I kept it to myself

So a few years go by and I'm in college and I am clicking around on some sites and I see some pics of Lisa Kage and Lisa Lawrence. I was hooked. Then I found some clip sites. There was no going back for me.

I had opportunities as I moved to L.A. and would visit Peanuts but I just didn't think I could go through with it. I even told the girl that I was with at the time about it and she even went with me one night when Allanah, Vicki, Vaniity and Danielle had a video release party. We even watched the videos together, but it never happened there.

So I come back to Miami and I get the bug and meet someone who I thought was a T but wasn't sure. So we get to the Motel and she's got nothing but padding on and was a little batty and a druggie, so I bounced.

I always have had unfortunate experiecnes when it comes to sex, so I just figured it wasn't in my cards. Then I am clicking around on X T U B E and I see there's a girl in town where I lived and we started talking online. 1 thing led to another and in Jan 11 we wound up meeting. I didn't know what to expect, but we hit it off. She was pretty hung and dominant and so I wound up getting topped. I can't describe the feeling, but needless to say it was good. Different but good. We both came 2 times during the visit and it was cool. My line about being a first timer was totally true LOL.

I've seen her a few times since, but not in a while...

[MrsKellyPierce]

ooh thanks for sharing gentleman very interesting

[south ov da border]

I thonk that it's cool to share if you want to, some never have. I never went in depth until today

[MrsKellyPierce]

I thonk that it's cool to share if you want to, some never have. I never went in depth until today

Some men may be embarassed or maybe don't want to share the girl..

I just think it's interesting how a first time was with a transsexual...since most people in general share their how I lost my virginity stories..

I really want to get back into Sociology classes again..people interest me so..

[Dino Velvet]

Mine was about 4 years ago. Was always curious but wanted to make sure I got a good girl for my first time. I scoured the ads and reviews almost looking over them with a monocle to assure I got what I wanted. I did. Nice gal and good looking as Hell with a great spot in Sherman Oaks.

Was nervous at first but she was very cool. She smelled great and as soon as I put my hand on her thigh the party was about to begin. Was a little confusing at first but she looked so good I had less issues than I expected. She is a total bottom and a great cocksucker and ended up being just what I needed for a first time. I've gone back to see her several times.

[baddoc]

I moved to SF in 1990 (pre-internet). There was a small club in the heart of the Tenderloin that had good bands play there. Driving home, I would pass by the girls standing outside of the Motherlode (now Divas), and strolling the block. One night, I couldn't resist, and took one very hot Latina home. My roommate was home, but asleep. I was nervous as hell. We only did mutual oral that night, but I was HOOKED. I eventually expanded my options in the bedroom, of course. Cruising Polk Street became a bit of an obsession, until getting my first cell phone in 1996. The Spectator was the newspaper to use for escorts back then, and I started buying every issue, and I still cruised Polk every chance I got. I was with Vanity once, when she lived down in the South Bay, Brandy Scott, and Lisa Lawrence, to name some of the bigger stars. I never stopped, and have been with some more current stars (Allannah Starr, Aly Sinclair). I still dated women, but when I was single, the TS girls were always there, and still are.

[luvblack77]

Reading again my story, I realize that it focused only on the sexual aspect of the encounter. The time I first met a transsexual lady at Jaque's I thought I was dating a genetic woman, and we agreed to go to her apartment after we had taken some drinks together and talked for a long time. One reason I did not freak out when I found out she was a transsexual is that I really liked her physically but also because I also enjoyed her company. After the first meeting, we dated a few times. She really was a wonderful person. However, I was too young to handle such a relationship. All the brain washing society plays on us came to haunt me. Was I gay? What would other people say? Were they staring at us because she was a TS or because we were an interracial couple or because I had spilled sauce on my shirt? We broke up, and to this date I feel sorry because I ended up hurting her feelings. She deserved better.

I have come to appreciate and admire transsexual ladies because they are more feminine than genetic women, they are proud to be women, they are very strong (have to be to deal with a society that discriminates against them every minute of the day) yet capable of greater intimacy than genetic women. I see transsexual women, as women and human beings who deserve love and respect. I thank the lady I met at Jaque's that evening in the 1980's for changing my life in ways I now feel proud of. It is unfortunate I was not good enough for her, and hope she found a caring husband or at least real friends worthy of her. She had four strikes against her: being a woman, a transsexual, black and not wealthy. I later came to understand how difficult it was for her to make a living, find a job or simply have a normal date.

I mention all this because KellyShore has an interest in Sociology, and no serious study about the TS phenomenon could be limited to TS ladies as sex objects. I hope KellyShore does go back into Sociology classes and helps through her thought provoking discussions and studies change the stereotypes, misconceptions and misinformation about transsexual women and the men (like me) who love them.

[rbiller]

My first was in Las Vegas. I was attending a photographers convention and I called a girl named Olivia who I found on Eros. I thought she was Asian but she turned out to be Hawaiian. Her ad said she was 5'9" and had a 6" FF cock. I'm only 5'7" and when she showed up at my room in 5" heels, OMG I got a stiff neck looking up at her, LOL. She immediately took off her shoes and we chatted a bit. Very nice girl. Now regarding the 6" cock. Not even close. She had a cone shaped cock that couldn't have been more than 3" or so. It got nice and hard but was not long enough to penetrate me. Well that was over 10 years ago and it got me hooked.