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

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.

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.

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Originally Posted by KellyShore

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

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

lmao the list goes on..do tell..

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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:

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.

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.

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.

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.

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Originally Posted by leckery5

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.

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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.

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.

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.

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.