What was your first T-girl sex experience like?

[JusticeG]

I am highly considering having my first TS sex this week. Up until now it has been just a fantasy, but I'm starting to think I should just take the plunge and try it out in real life. I really hate to have to go to a "provider" and pay for my first time, but there don't really seem to be any attractive t-girls around here that don't charge. She is only going to charge 100 for me because I am going to be coming over from the next town over, and that seems like a good enough price to be worth the trip for how attractive she is.

I am a little nervous and unsure if I'm going to like reality as much as the fantasy though. What was your first time like? Did you enjoy it or regret it? If you paid, was it worth it? Was the reality as good as the fantasy?

[saifan]

Paid and very much worth it.
Be safe and have fun.

[saifan]

Oh, and in my experiences so far the reality has been so much better than the fantasy.

[Dino Velvet]

I did my homework and got a well reviewed escort on http://theeroticreview.com/main.asp .
Went to see her. She was beautiful, sexy(good bottom GFE), nice, and had a clean/secure apartment. Don't regret it at all. In fact, I've seen her 4 times now and each time gets better.

[evil_twin]

Why don't you try myspace.
What I usually do is go on myspace and find a dude (that has a lot of trannies in their myspace friends list) or a tranny that lives in my area.
I check there friends list for trannies that live in my area and add them to my friends list.
When they accept, either they will flirt with me, or I will flirt with them.
Just take it from there.

My first experience was paid.
I was watching TV and the news did a 'cover story' on the tranny stroll.
It was mainly about how the girls prostitute to make ends meet because they face a lot of job discrimination.
They mentioned the street and the best time to see a bunch of girls.
So, I went down and I saw so many 'girls' I couldn't make up my mind.
So I found a real beautiful girl and fucked her in the back set of my car.

[Silcc69]

Why don't you try myspace.
What I usually do is go on myspace and find a dude (that has a lot of trannies in their myspace friends list) or a tranny that lives in my area.
I check there friends list for trannies that live in my area and add them to my friends list.
When they accept, either they will flirt with me, or I will flirt with them.
Just take it from there.

My first experience was paid.
I was watching TV and the news did a 'cover story' on the tranny stroll.
It was mainly about how the girls prostitute to make ends meet because they face a lot of job discrimination.
They mentioned the street and the best time to see a bunch of girls.
So, I went down and I saw so many 'girls' I couldn't make up my mind.
So I found a real beautiful girl and fucked her in the back set of my car.

This can't be in America!?

[Mr Dazzle]

I would never pay to get with a TS...

[addicted]

prepare to vomit

[addicted]

I would never pay to get with a TS...

Thats because they dont accept food stamps

[gieric]

Don't know, still trying to find them in my area. You think it would be easy in a city with as many gay people as tulsa.

[bte]

My first experience was I met this girl at a club in Rome. It was during the summer months when they have the gay pride festivals. I went to area called Testaccio where they had the Gay Village. I met this girl in a bar and we had some drinks and had an one night stand. It was pretty cool. She told me she was transgendered before I started talking to her and I was like "okay".

[alpha2117]

I was young and used to go out to a club in town that played a lot of dance music. The crowd was mixed. The mens was on the far side of the dancefloor so everyone went to the womens. I met up with a couple of ts girls includy Christy McNicole who did some vid work over in the US. We hung out. One night we just did what comes naturally when you are young and horny.

One thing though I'd recommend a less endowed girl first time out. If you are interested in oral or anal with her in the top role then a girl with a big package can be problematic.

[Mr Dazzle]

I would never pay to get with a TS...

Thats because they dont accept food stamps They don't have food stamps where I live.

Ive met TS who weren't for sale but all do love money. I wish they were more independent.

[LilWyte]

havent had it yet

[BlackShemaleLover]

My first experience was a disaster.. I was so nervous, and I choose a ts with an amazing body but she was not hot at all on bed. She stay in the bed without doing anything even not touching me.

I was a bit dissapointed. But some weeks ago while I was walking in a redlight district, a beautiful TS showed me she was really excited by me. I decided to go with her and then It was wonderful!

[Byrdman]

I used to go clubbing a lot when I was in high school and at one of our regular haunts my friends and I met a group of Tgirls. They were all older, late twenties, early thirties which seemed ancient to us, but they were fun and they liked us and, I guess, my friends felt sophisticated hanging out with an older set of glamorous Tgirls (some where crossdressy club kids, others were legit Tgirls). Anyway, over half a dozen visits I really hit it off with a Tgirl named Rochelle. I was 17, she told me she was 28 (though I later found out she was 35 at the time). We fooled around a little bit, innocent stuff, a kiss, a cuddle, usually in a dark corner of the club ( I was rather apprehensive about my friends: after all, it was cool and all to hang out with and dance with the TGirls, but, this being high school anything else would have been frowned upon).
Anyway, I eventually got up the courage to ask her out on a "date", (well, a movie). I was very excited, but it occurred to me that I had zero experience with TGirls (or men for that matter) and, really, not much experience with GGs either (basically I had had sex twice at that point).
So I raided my savings, looked in the local paper under TS Massage and booked a visit with a working girl. It's funny, because I hadn't really thought of Rochelle as a TGirl until that point, I was just attracted to her. I mean, I knew she had a cock, but that wasn't really part of the attraction (this was in the pre-internet era and I had seen very little TS Porn at that point).
Anyway, my visit to the pro went about as well as a first-time can go. I was nervous and, when her cock popped out, I hesitated for a moment and then went for it. Sucking cock, as it happened, came very natural to me. When she started blowing me, I came almost right away, which was a bit embarassing. She offered to fuck me and, yep, it hurt like hell. But, by this point, I was so turned on it didn't matter.
The very next day I went out with Rochelle. We had a great time and, yes, we ended up having sex. We saw each other maybe another ten, fifteen times at the club and another half dozen times on our own. She then moved to Miami and I never heard from her again... until last year, that is. I saw a woman in a supermarket in suburban Chicago, where I was visiting, who looked very familiar. It was her. Turns out, she had her full surgery done fifteen years ago. She's 54 now, she lives with a man and his teenage son and, for all intents and purposes, she's a suburban mom.

Sorry it's a long post, just wanted to underscore the fact that, sometimes, even after TGirls turn 50, things turn out just fine (at least for her... she got what she wanted in life... a family, a 'husband' and a white picket fence)

[archineer]

Met a girl in the Wayout club in London- I paid we went back to her hotel. The sex was great, just as i'd hoped it would be- all the softness and gentleness of a woman with the horniness and sexual knowledge/connection of a man. :) We got talking however and once she realised I wasn't just after sex (ie. I would date the right girl) she insisted on paying me back! We spent the weekend together looking around London and went for a meal that Sunday night. Alas she does not live here so it couldn't go any further. :(

[Intrepid]

My first time was hot. I thought she was a woman and then she told me she was a "special girl". And she was. Saw her about 6 more times over the course of the next 8 months. Then she disappeared.

[hippifried]

Both of us were so drunk we couldn't get it up.

[talldudeil]

It was in LA and I picked a gurl from the local adult paper, i was rushed and not very good, but I enjoyed it enough to continue.

[tomvan20000]

i was top. when i first put it in i t kinda hurt, but after that it was amazing

[LilWyte]

i was top. when i first put it in i t kinda hurt, but after that it was amazing
wait....you put it in...and it hurt you?.....

[brickcitybrother]

Hmmmmm ... it was the start. lol