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

**christianxxx** · 05-02-2012

In 1997 I had just graduated from university and a bunch of my basketball teammates and I were hanging out at a small nightclub in San Antonio, Texas. There were 2 tall, huge boobed TS girls at the bar. I could not stop staring. Eventually, I went over and chatted up one of them. It turns out she was a DJ on the local morning radio station (Miss Ree). She gave me her number, I texted her, drove to her spot, and we fucked (top and bottom) the entire night. it was amazing. i was hooked after that. damn 15 years!

**MrsKellyPierce** · 05-02-2012

Oh wow Christian shared his..

Ooh I love this...

Thanks to everyone who is sharing..I will comment farther..after my cam day and going to my step-daughters recital...

**firejimmiller** · 05-02-2012

Well, I guess I have something in common with Christian beyond the shaved head. I met a girl online around '03 and drove down to San Antonio to meet. Knew she was TS and this was first time with any cock. She took it slow with me and we spent the night drinking wine and watching a movie (still remember it was "Traffic") before touching led to oral. My whole body tingled with a drunk floating feeling when I went down on her. Same type of feeling when she rode me from behind a little while later and we both came as she fucked me. I actually stopped myself the first time and she scolded me when I told her I didn't want to cum on her carpet (bent over the edge of bed). I fucked her mish and we relaxed for a short time before I asked for a repeat. This time she told me not to hold back and damn did I ever cover that floor.

I think I joined this site shortly thereafter and the rest is history!

**robertlouis** · 05-02-2012

2004 Singapore. I was working for a UK business which was aiming to merge with an Asian company based in Singapore. One of the advisers working with us on the merger was a very attractive Asian accountant. We worked closely together and clicked immediately on a personal level too. We went out one night for dinner and drinks and discovered a mutual attraction too. After a couple of dates she invited me back to her place one night, where she broke down in tears and told me that she had been born a boy. I had never guessed - she was all woman and very, very feminine. As it happened, she had also had SRS. I explained to her that I'd fallen entirely for her as a person and not for what had once been between her legs and we made love - that's what it was, much more than sex. We were incredibly close for the three months that I was working on the merger - which we successfully concluded. What we had to hide, of course, wasn't her sexuality, but the fact of our relationship, as it might have compromised the deal. Funny old world.

We were both very keen to take things further, but she had significant family issues as a new partner in a big six accountancy firm she was the primary breadwinner for almost all of her family back in Penang, and I was of course working for a UK-based outfit at board level. I managed to drop in whenever I was back in Asiapac and things were just as good every time, but over the years inevitably we drifted a bit, although we kept in touch via email, skype etc.

Anyway, earlier this year I went down to Australia to stay with my sister and set up four day stopovers in Singapore each way, spending all my time with her. It was a risk for both of us, but it was just as good as ever. Upshot is that she still has her family issues, but I have now met her parents and siblings and am on the way to becoming part of the family. We want to move on, formalise the relationship and stay together, but it still needs time. But we're patient. Neither of us has had meaningful relationships while we've been apart, and we are completely determined to do whatever it takes. We talk most nights and I'm happier than I've been for decades. She's going to France with me in July on holiday.

I've even started to write happy songs - if any of you know my music that's one hell of a shift. Anyway, please wish us luck.

So for me, it was never about a longstanding (oops!) interest in transwomen. I just happened to fall in love with one. Lucky me.

**Dino Velvet** · 05-02-2012

Originally Posted by robertlouis

2004 Singapore. I was working for a UK business which was aiming to merge with an Asian company based in Singapore. One of the advisers working with us on the merger was a very attractive Asian accountant. We worked closely together and clicked immediately on a personal level too. We went out one night for dinner and drinks and discovered a mutual attraction too. After a couple of dates she invited me back to her place one night, where she broke down in tears and told me that she had been born a boy. I had never guessed - she was all woman and very, very feminine. As it happened, she had also had SRS. I explained to her that I'd fallen entirely for her as a person and not for what had once been between her legs and we made love - that's what it was, much more than sex. We were incredibly close for the three months that I was working on the merger - which we successfully concluded. What we had to hide, of course, wasn't her sexuality, but the fact of our relationship, as it might have compromised the deal. Funny old world.

We were both very keen to take things further, but she had significant family issues as a new partner in a big six accountancy firm she was the primary breadwinner for almost all of her family back in Penang, and I was of course working for a UK-based outfit at board level. I managed to drop in whenever I was back in Asiapac and things were just as good every time, but over the years inevitably we drifted a bit, although we kept in touch via email, skype etc.

Anyway, earlier this year I went down to Australia to stay with my sister and set up four day stopovers in Singapore each way, spending all my time with her. It was a risk for both of us, but it was just as good as ever. Upshot is that she still has her family issues, but I have now met her parents and siblings and am on the way to becoming part of the family. We want to move on, formalise the relationship and stay together, but it still needs time. But we're patient. Neither of us has had meaningful relationships while we've been apart, and we are completely determined to do whatever it takes. We talk most nights and I'm happier than I've been for decades. She's going to France with me in July on holiday.

I've even started to write happy songs - if any of you know my music that's one hell of a shift. Anyway, please wish us luck.

So for me, it was never about a longstanding (oops!) interest in transwomen. I just happened to fall in love with one. Lucky me.

That's a great story, Robert. Good luck for sure. I remember you talking about Singapore before.

**kaientai** · 05-02-2012

Dasha or Carmen in those days was my first shemale experience , I nervously called her a week in advance to set up the date when the day came I was realy nervous not sure if I wanted to go through with it but found the courage so to speak and went. Once in her city two call system was used she opened the door hiding behind it , then she closed the door and there she was in a beautifull short dress she took my breath away and hanging below that skirt was just an insanely big dick... We went upstairs where we engaged in some small talk she then proceeded to crawl on my lap for some deep french kissing when all of a sudden i felt something huge and hard pressing against me she got up slapped me in the face with it and told me to suck it my life was never the same haha.. I have seen her 7-8 times after that she never disapointed she also gives a great massage ..
God I miss her lol

**Ecstatic** · 05-02-2012

Excluding brief encounters behind glass partitions at peep shows, mine was about 11 or 12 years ago, a gorgeous 5'11" French-Mexican woman who I found on Eros. We met at her hotel in Boston and really hit it off, becoming friends ever since (even well after she quit the escort scene). She had incredible 38 DD's (courtesy of Dr Grey, absolutely flawless) and a 7.5", thick tool. Our first encounter was purely oral, and I remember cumming like Mount Vesuvius. Really, it was like I hadn't cum in years. I knew I was hooked then, and we got together many times after, usually swapping top and bottom. Of course there were many other girls, and all this led me to where I am now, producing TS porn, but she remains, along with one other very special woman, my all-time favorite.

**Helvis2012** · 05-02-2012

Met a girl in Starbucks and we agreed to meet later in the week at Sally's. We hit it off and the rest is history.

**StinkyPete1000** · 05-03-2012

Bam Bam was my first about 7 years ago. Very, very nice time! She was very understanding and treated young first-timer me very nicely. She gave me a great bj and let me top her. It was simply amazing.

**kelyman69** · 05-05-2012

first time 2003. went to a ts party on my birthday.i only had 30 dollers in my pocket.but decided to go anyway. i just had to check this out. i hopped the train from brooklyn to manhatten. i found the club without any problem. paid the cash to get in and i was pretty impressed. i met gia darling and allahna starr witch was a dream come true. there were plenty of escorts but i had no money for that. i had a few beers and started flirting.one of the models that night took a liking to me and we ended up going back to her hotel room. as soon as we hit the door we were makeing our way to the bed she was about 5 foot 7 , 130 lb, blonde white girl. she had about a hard 7 inches. nice b cup tits. i sucked on her tits for awhile and, made my way down to that shenise.... ha ha. gave her oral for a while and tounged her ass to get it ready for a pounding. i fucked her for about 20 minutes raelly hard. she was moaning so load i started to get nervouse someone would complain. i busted a nutt and layed back to recover. turns out that was only the beginnig. she gets up and gets her purse and pulls out a small bag of cocaine and i snort a line off her long finger nail. i lay back on the bed and she starts licking my asshole. that was a first for me. the feeling was amazing i closed my eyes and she grabbed my hips and started fucking me. she said "your supposed to be fucking me and im fucking you" and laughed. i didnt feel any pain she had me pretty relaxed. we musted fucked in ever position for 5 hrs. i came numourouse times 4-5 times. end of the night we called a cab and i never seen her again. i forgot her name . i was pretty much in a haze when she told me. ive tried to look up old party pics to find her.none go back that far. it was one hell of a birthday. the best one i ever had haha