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.

[christianxxx]

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]

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]

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]

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]

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]

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]

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]

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]

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]

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

[Hydrant]

My first time was with a girl called Shelley who worked out of a nice flat near Paddington Station in London. Must have been about 1998... before the internet was up and running for most people. I chose her ad out of a couple of others in the Daily Sport - it said "Busty Shelley, shemale" if I recall correctly.

I'd wanted to do it after buying a few shemale mags in Soho porn shops and finding that I was literally salivating at the mouth at the sight of these gorgeous girls with cocks. I've never been attracted to men, but I knew I had to get a shemale dick down my gob at the earliest opportunity.

Anyway, Shelley was absolutely wonderful. Utterly gorgeous with long dark wavy hair, totally convincing, beautifully dressed and willing to do anything I wanted. She was on hormones and had lovely big soft tits but never got moody like some girls do, although it did stop her getting much of a hard-on except on one memorable occasion.

About the third time I saw her I was fucking her in the ass from the front. We were kissing like crazy and after I came she pointed out that she had an absolute stonker of a hard-on. Well I would have liked her to take my ass cherry with it, but she wasn't up for anything so active. But I did enjoy the feeling of a hard cock down the back of my throat for the first time two seconds later...

She always gave me a superb blow-job and would let me suck her dick and fuck her for as long as I was able. Couldn't have asked for a better introduction to the TV/TS world!

It was Shelley who introduced me to really rough face-fucking. She liked to prop her head up on pillows on the bed then get me to go on top with my knees either side of her waist and my cock pounding in and out of her hot mouth while she gripped my bum hard or played or gently squeezed my balls.

Mmmm.... in the end I came to appreciate being on the receiving of that treatment from shemales.

I believe she had the full op some time ago and don't think she works any more.

[leckery5]

I had seen girls online and had cetainly developed an attraction. So it must have been in the back of my mind. I was in Munich and I went out for a few beers. On my way to the train, I saw a club that advertised t-girls.

When I got down the stairs I noticed there was a mix of GG's and t-girls. There was a beautiful latin t-girl performing. A few of the GG's approached me and asked if I had wanted to go to the champagne room. I declined. I sat on a sofa and watched the beautiful t-girl do her show. Her show ended with her pulling her panties down, revealing a super hung cock. She disappeared off stage.

Suddenly I had a voice behind me asking me if I wanted to go the champagne room. It was the beautiful latin t-girl. I declined. She asked again and I was overcome by her sexiness. Next thing I know I am in the champagne room and she pulls my cock out and puts a condom on it. She had a huge bulge in her panties and I asked her if she was going to put a condom on it. She said there was no need. She was inspected by a doctor weekly and had a license. She pulled her cock out. It was huge and sexy. A force came over me and it was if I were compelled to go down on her. I just remember thinking, it finally happened. I'm sucking t-girl cock. I remember saying, I can't believe I'm sucking a cock. She responded, there is always a first time sweetie.

She posed for me. I remember she was Argentinian. Very Very sexy. Grade A t-girl. The session ended with her bending over a table. She had beautiful legs and a beautiful ass. She made me put my face in her ass and lick her ass and balls.

I was very weirded out the next day. It took some time getting used to knowing that I had crossed that line - the line between fantasizing and doing. I had sucked my first t-girl cock. I also knew that if I were confronted by a beautiful t-girl again, I would probably be putty. Well the situation did present itself again and I was pretty much putty. I sucked t-girl cock number 2... and the beat goes on.

[EyeCumInPiece]

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

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

lmao the list goes on..do tell..

who: Well-known non-working girl

when: about 9 yrs ago

why: to turn fantasy into reality

how: orally

def weirded out......thought "what the fuck am i doing?" :loser:

[LeatherTGirlLover]

Had become more and more attracted to tgirls over the years, through online porn and making the odd friendships on various sights but i'd never ventured. Up till about 8 years ago it was nothing more than a fantasy but that all changed one night upon venturing into Manchester's Canal Street.

I met a beautiful, kind, sexy, kinky Oriental tgirl called Ayesha, we instantly hit it off and that night i broke my tgirl cherry (so to speak), i went on to date Ayesha for 4 months but what with my travelling and her *ahem* extra curricular activities we decided a friendship would be better, she moved back to the Phillipines about 6 months later and i haven't heard from her since.

Up till then i'd been strictly straight and i still don't go with guys but then i very seldom go with women these days and most of my recent sexual partners have been tgirls....so a special thanks is in order to Ayesha, wherever she may be.

[Jackal]

Who? An escort in L.A. When? I was 21. Why? I had an attraction to transsexuals since I was a teen. My affinity has grown; so many of the transwomen I have me are beautiful, attractive, lovely and charming ladies. Long story short, we engaged in oral and anal after some kissing and caressing. It was an amazing and pleasurable experience. She was Mexican, blonde, curvy and very pretty.

[randydandy2099]

Had my first encounter yesterday. Found a pretty T-girl online and went to her apartment for a massage. Nervous as hell, not knowing what to do, I waited till she finished the massage before stroking her leg. She asked if I wanted more, and I said, "Of course!"

She laughed and said she couldn't tell! I told her it was my first time and I how nervous and scared I was being here. She began stroking me and the rest is history. Very exciting and I'm looking to return to her and finding other sweet and wonderful ladies to share some erotic encounters.

[Rusty Eldora]

3:30PM 10-3-12 TS Pamela in Seattle, a great first hour. I was very nervous, never had touched a cock except my own. Would I freak out - I wasn't, drawn to it like a moth to a flame. I am very oral but was pretty bad on technique. She topped me for my first beyond toys - it was really great.


I was very weirded out the next day. It took some time getting used to knowing that I had crossed that line - the line between fantasizing and doing. I had sucked my first t-girl cock. I also knew that if I were confronted by a beautiful t-girl again, I would probably be putty.... and the beat goes on.

I wasn't weirded out at all, but my ass felt great but stretched. Within the week I saw TS Michelle, who I have seen a 2nd time. Last week I had a day in Seattle, tried a TS from Eros - very cold and mechanical - needed a good fucking, tried a Backpage TS - better but not satisfying so I scheduled a last minute appointment with Michelle who fucked my brains out with her 8", deep throating it was a challenge that I met with my first real CIM - felt satisfied.

Both Michelle and Pamela, the total vibe was female, maybe they were comfortable with themselves. The other 2 I saw it felt more an act.

I didn't really hit Tgirl porn at all until about 8 years ago, a post on a gg escort review board was Guess The Guy - All were Thai ladyboys. My curiosity built and I found myself checking the Eros TG section. It was actually a kinky gg escort I had seen several times that took me to the dark side. She described to me in very erotic detail why she loved sucking so. I had to try it - glad I did.

[JenniferParisHusband]

I am old enough that my first knowledge of transgenderism came out of my parents watching old reruns of Milton Berle in drag. I didn't understand at that young age, but I knew that it wasn't a woman in that dress. So the possibility was always there in the back of my head. Then 2 things happened. First, I was at a local record store / head shop and there was a birthday card with a topless redhead on it. Saw the tits and her beautiful face, and started sporting wood right there in the store. Then you open the card up and just schlong for days. I think I was like 10 at the time. I still didn't quite get it, but she was a lot prettier than Milton Berle, and it stuck in my head. More than a little confused about the wood part, wondered if I was gay, etc. The second thing that happened at this same age was that our cable had the Playboy channel, it was scrambled, but if you watched long enough, eventually you'd see something. One day I'm listening to Electric Blue, hoping to see a breast, and then there's Sulka clear as day. Again, got wood, didn't understand it. But 10 years old, easily influenced by anything porn-ish, it stuck with me.

Skip to the 90's. I'm 20 something and I am now living in a new town. I come across an advertisement for a local lady who went by LedaMay. Called her up, quoted her ad, and then had a strange experience with her where there was no sex, but we drove around looking for a blender, watched videos of her walking around naked at burning man, and then went to my first club where I felt horribly out of place. Leda thought it would be funny to make me tip one of the dancers while I was nervous. The girl on stage shoved my hand with the dollar down her panties, touched my first dick that night. Was completely turned on and weirded out by it at the same time. But it stayed in my head again. A few years later, I'm out of town on business, and there's an advertisement on a site called BigDoggie.net. I'm not even sure if that's still around, don't want to google it. They had a TS section that no one ever posted in, except this day, and close to my city, is a girl going by Gia. I was into her immediately. Made the call, negotiated as best as I knew how to then, and made an hour drive to her, almost turning around every chance I got.

I sucked up the courage, went to the door and was greeted by a GG pro who lived with her, and who gave me a kiss, a crotch fondle, and led me by the hand to Gia's room. Gia was in a really sexy black bra and panties, and was lying on the bed in just the hottest pose I'd ever seen in person at that time. I knew she was pre-op, but it was tucked well. She had not yet had the facial surgeries, but had implants, and was a bottom. Those last two were really all I cared about. She had me get undressed, and lie next to her. I was super nervous, then Gia took over. She did everything possible to make my first time wonderful. Started undressing slowly, letting me touch, and kiss, she kept her penis hidden through most of it. She french kissed me, which stubble was awkward, but didn't kill it for me. And while she was stroking my cock, I felt hers touch mine. I remember flinching a little, but she grabbed both of them and started rubbing them together. It was increidble. Before I knew it, she was going down on me, and then pushed me back onto the bed, started reverse cow-girl with her dick and balls bouncing against mine. She was very vocal, which I liked. Then she got off, covered me up and finished the job facing me, her eyes never leaving mine, my hands gripping her breasts like they were handles on a roller coaster, and her hot breath against my face. I came, she collapsed onto me and kind of grinded her body into mine while my cock was still in her, moaning and stroking my chest and head.

It to this day is one of the greatest sexual experiences I've had with any woman TS or GG! I was hooked from that moment. I've been looknig for her ever since, I'd love to see how she's been, even though I know she's out of the professional side of things. But thanks to Gia, I've probably been more into TS ladies than GG for a long time now.

If anyone knows of her and where she is now, I'd love to know.

[serial138]

March of 2000, I was at Berlin in Chicago. Was actually there with a GG I was trying to hook up with, her gay cousin was sick of straight clubs so we wound up there. I didn't mind because Nosmo used to spin at the club back then.

While we're there this gorgeous Tgirl and her CD friend (obvious one at that) were talking me up with my GG friend. I excused myself to use the restroom at one point and she followed me right in to the stall, where she demanded to see if I was telling the truth about my cock size. (I like to tell people its small so I always overachieve, lol) Of course I showed her it wasn't as bad as I made it out to be, and she proceeded to go down on me as soon as I got hard in her hand. I had no clue she was a transexual until she stood up after I came and proceeded to pull hers out and masturbate furiously into the toilet. I was too shocked at everything that had happened to return the favor, and it is the Berlin bathrooms, which are disgusting. Having been to Crobar many times I had seen many TS women, but never one so passable. Strangely, I was perfectly calm about it, and didn't even try to hide it when the GG I was with got pissy I was gone so long.

3 days later I went back to try and find her because now I was curious. Instead met another gorgeous Thai girl and went home with her. Learned all about being on top, being on the bottom, it was a truly eye opening experience, and I loved every minute. I never really dated a TS until about 8 years later. That's another story though.

Course, here I am almost 13 years later, and I cannot remember any of their names. I remember the Thai girl lived in a high rise behind the White Hen on Halstead over by the police station in Boystown, but that's about it. I partied hard in those days, memories not so good anymore.

[hallie]

east 65st. I don't remember her name she told me she was from clifton nj. I was about 20 or so. It was a great time. If i only knew then how ifeel now.

[alexanderseven]

My first time was with Yasmin Lee in Boston, about 4 or 5 years ago, I believe. She was amazing- so beautiful and sexy and sweet. I was not in a great place, however, back then. I was nearly 300 lbs and had a lot of self esteem issues. Those issues prevented me from doing a lot of the things I really wanted, with her, and with life in general. Happy to say that a handful of years later, I've lost 130 lbs, I'm fit, and I've had a number of relationships with tg girls. Life is good. In some way, that meeting with Yasmin really gave me the impetus to get my life together, physically and mentally. If she reads this, I'd like to say thanks. You were amazing.

[magus13]

About 13 years ago the most amazing ts was visisting NYC. Her name was Ruby and I told myself that would be the the ts I would get my nerve up to meet. Had an amazing session. Top bottom mutual cim. She asked what I wanted, I told her to be my girl. She said that she was my girlfriend for the next hour and it was an incredible experience.

[timid1]

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

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

lmao the list goes on..do tell..

The beautiful Valentine in West London.
Early Nov. this year
Why? Because I could no longer resist the urge to experience a tgirl , and she looked incredible, and her reviews were fantastic.
She was very sweet and even more beautiful than her pics. I was incredibly nervous , but she was extremely kind and reassuring. It was an amazing first hour . I was a little uncertain and she wore a condom when I started to preform oral, however after about 60 secs I begged her to rip it off! Oral was far hornier without a condom, for sure! I was soon begging for her to penetrate me, which she did expertly!
Yes, I'm now addicted! And I felt elated and euphoric after the first time (which was pleasantly surprising) . I enjoyed Valentine so much I visited her again 4 days later !
I love girls , but sex with tgirls, for me , is even better!
I'm so happy I took the plunge, and that I was lucky to have a wonderful first experience
x

[dickten]

Growing up Catholic in all boys schools is tough on the emotional adolescence needed for sexual maturity. I loved girls and they seemed to love me, but I never had the courage to talk to them. I had one girlfriend in High School who went to my prom, but it was just very casual friendship. Once I left the small town to be on my own at college in the big city of SF 1976, I seemed to develop what I would call a path of fate. You decide. One night some of my buddies decided to go into the tenderloin to a theater where they had strippers. On the way back walking out of the TL a beautiful asian lady stopped me and asked if I wanted to party? Her voice seemed different and even before I knew what clocking meant, I seemed to sense she was a man, but still a very sexy one. She grabbed my hand, gave me a kiss on the cheek and told me how cute I was. At that point, man or woman, I was very idealistic about sex and knew that I did not want a one night stand. I told her how flattered I was and how beautiful she was and told her that I wasn't into that. She took my hand and put it on her crotch to tell me what I was missing. The hardness shook me and I quickly left. One year later I am in New Orleans for the Sugar Bowl and mad drunk walk into "Papa Joes" , what I thought was a burlesque place. I then notice it is a female impersonators bar, which was not too shocking since I had heard of places like that before in Boston growing up, but still probably not my choice as I was drunk enough to say anything to any girls and wanted to try and get laid. Before I could turn around, I tall thin latin brunette in a black sparkly dressed grabbed my hand and brought me to the back of the place, sat me down, sat on my lap and ordered a round of drinks for us. Very expensive drinks btw. We started to talk and then I realized she was one of the performers. Not much I could do with a lady on my lap, so I just sat and talked as she asked me all types of things. I told her I came in by mistake, which she didn't believe and decided to inspect my package (It was dark in the back) This oddly felt good, but I knew I had to leave and my chance would come when she had to get up and do her "set". We had a couple drinks and she kissed my neck a couple times sending shivers thru me, but when she got up, I bolted and spent the entire next day questioning my sexuality. 1980 My First corporate job in NYC, Living in crappy Tribeca before it became what it is today. One night I decided to hit a Broadway show with a girl cousin of mine, after the show I walked her to Penn Sta for her train and walked back to Times Square for a quick jerk in one of the peep shows. Walked into Playland (next to Port Authority) and noticed they had a live sex act downstairs which sounded interesting. As I walk down the stairs, I notice you need to run a gauntlet hallway of two way booths full of TV's and TS's before getting to the live action. One very aggressive black TS Grabs me and yells fresh meat, pushes me into the booth and tells me that the manager is not around and that she does not need to go into the adjoining booth. I'm fumbling for something to say, while she reaches under her skirt and puts her anacoda in my hand. All the while this is happening, all the other TS's are in the other booth watching to see what will happen next. I kindlly tell her that she has quite a nice pet snake, but that I'm not into snakes. She acts like all pouty with please, please, it will be so nice, etc and I manage to side step up and over around her to get back into the hallway and then I'm met with a cute white Ts who blocks the way and asks if I'm into white girls more? No, just want to go see the "Live" sex show I tell her. After a while I make it to the area where the little booths shut behind you and the wooden slats open up after you throw the coins in them to reveal two girls licking each other. They walk around allowing you to dildo dip them for a fee. Pretty cool, hot, degenerate stuff, but I can't seem to get my mind off the "Ladies" in the hallway. I leave shortly thru the "Correct" exit by the side that I should have used in the first place a little shook up and even more confused. A year later I am coming out of a bar in the Lex and 20th street area and notice a ton of Ts's all working the streets, this amazes me and I watch from a distance for quite some time. It's the first time I notice that some of the girls are prettier than most woman. I then go search for a subway home and also look to get the morning edition of the Times. As I reach for a paper, so does this young, cute, asian girl too. I laugh and let her pick first, go buy it and take my time looking at the headlines in hopes I can say something to her. She is first and asks if I live around here? Tell her no, that I was with friends for dinner and drinks, we talk a little bit, she tells me she goes to college in the city, she lives at her brothers little apartment while he works in London. Asks what I do and then invites me up for a drink. We kiss and fool around a little and then i ask her if we can go out the next night, that I liked her and was a gentleman and wanted to get to know her better (How stupid of me) She was fine, tiny, thin, sexy features, etc. We exchange phone numbers and I'm pumped! The next day I get a call from a man telling me it's her brother and that Mimi really liked me, but wanted me to know that she was born a man. She did not want me to get mad on the date and she was embarrassed to tell me last night. WOW... NYC is crazy, he then asks if I still want to pick her up. I mention I needed to think about it and that I'd call her back that day. I never called. Pretty shitty thing to do and to this day I still feel bad. A month later I'm in the village partying with my cousin who decides he needs to come out of the closet to me. I'm the only family member who understands and he even wants to know if I might be gay? Fuck, I'm batting 1000. By this point in my life I've had a couple of girlfriends and sex 3 or 5 times and with all these TS run in's I'm not sure what I am. He decides to take me to this bar on Christopher Street called "Boots and Sadles" to see the other side of things.
I walk in and I finally figured out what it feels like to be a hot chick in a bar. I was 22 and had tons of guys trying to buy me a drink or talk to me. I told my cousin to pretend he was my boyfriend so that this would stop. It helped a little. Until his real boyfriend showed up and asked him if his cousin was gay too? I told him I didn't think so, none of the these guys did anything to get the old butterflies going, which was nice to say and to feel. They then wanted to go try another bar further down the street called, "The Anvil" and I told them, OK, Only one more bar. This place was extreme, guys in leather, guys in 40's and 50's, you name it. I told them it wasn't for me and that I was going to head home. All this after taking a piss in a bathroom where I could hear guys fucking in the next stall and getting blowjobs in the outside hall. Too much for me. On my way back to the subway, there she stood, in a gold glittering dress, a latin Diva with big hair and high heels in fishnet stockings! She asked if I could give her a light? I told her I did not smoke, she then asked if I wanted to smoke some weed with her if she could find a light? She had just come from a place called the florent restaurant with two of her other friends and I think she may have been done working for the night. The other two ladies walked away and told her to have fun and told me I should escort the lady home. This time I was not fooled and felt a little peace in understanding the situation. I told her ok, stepped into a little store to buy some smokes for her and get a Bic. We walked the thru the Meat Packing district talking and smoking watching the crazy night life unfold around us in the Pre-Gulianni era. Made it to her apartment and ended up making out like teenagers. I told her I like her alot, but that could we slow down (Again, punking out) But she actually liked the idea and we slept in the same bad all night just holding each other. In the morning I took her for Breakfast and caught a glimpse of her looking like a young man in the bathroom which kind of spooked me. At breakfast she told me that she was from Monterrey Mexico, family basically disowned her, but she had cousins in Alphabet City that knew about her and kind of accepted her. She had a Day Job a a Florist, but it was not enough to pay for her Hormones, Fashion, etc. She did work at night, but wanted to try and find a better paying job at Macy's or Barney's as a sales girl (she could pass easily) That following night I looked in the village voice for a good Mexican Restaurant to take her to. I think it was called Los Lobo or something. After Dinner we went back to her place and explored each others bodies and she let me suck her and vice versa, then I could not wait to be inside her and the combination of kissing her and looking down at her hard cock was too much and I then had the best orgasm of my young life. We then began a 2 year romance that I'll never forget her. Summers at the Beach in Montauk, partying our asses off at Peppermint Lounge, CBGB's, Mudd Club, Danceteria and Mott Street dim sum every sunday to work off hangovers. She eventually got to work at a store in Soho as a Sales Girl and I heard she even went back and got her degree and is doing something in fashion to this day. It's funny, when I visit, I try and pass by our same old haunts to hope and catch her on the street, but as you know, everything has changed since then and have had no luck. Since then there have been two other long term Girl Friends who were Ts. I often think that it was a series of these events that drew me into my predilection, possibly other things? My relationships have been rocky to say the least, it comes with the territory if your man enough to stick around, but I would not trade it for anything. I'm currently seeing a younger Ts now, she is very bright , smoking hot and tells me she loves me,
but it's still early, she has strayed a few times and I understand more than anyone that this seems to come with the package. Growing up with a father figure who never loved back or was abusive or growing up and wanting the attentions of boys who may have treated you badly or thought you were not pretty can be a factor in why people need to seek constant male attention thru sex, but that's not going to stop me from trying to find the right person or at least work thru that persons problems if I love them. It's all just part of the deal in enjoying these exquisite ladies in our hearts.