have you ever approached a Shemale before?

[TrannyLover2]

Never. Haven't gone looking for it though.

However, I was around 18 and decided to walk around the area of my city where I knew there were a lot of prostitutes. I wasn't looking for anything, it was just after a concert and I was curious about that area.

A girl with great legs, but tired eyes asked me "do you have fire?". I knew she was a prostitute, but I never thought she'd try to hook me, a kid in jeans and a t-shirt (and little money in his pocket). So I politely said "no, sorry" and it wasn't until the following day that I remembered this is a key-question for a customer. Of course then I started playing the scene in my head and I realised that she was a ladyboy. Something in her voice and face.

I felt strangely flattered, even though I knew she would have asked me for money. I mean big and expensive cars were stopping there all the time, but she talked to me. She was quite pretty too and had a very nice body.

[postopadmirer]

Besides this and the Hung Angels Forum I've only talked to Transsexuals once "that I know of". I was at the "boys will be girls" in New Orleans in the 1990s.
I was still very much wondering if I would transition myself. Nothing happened except I met some nice girls, and always wished I could go back. I wanted to take some of them on a date. A real date, to the beach, a movie, dinner, etc. A few of them were very cute but I was to shy to do anything but watch the show. Oh what could have been.

[aussiepride]

One time after a night on the town I was headed back home when I decided to go take a look in the taxi club in sydney.
I had a drink and was just walking around catching the gaze of a few ts when I locked eyes with a little cutie who was in the outside pockies section.
I just went over and said hi. Said she looked cute.
We chatted for a bit then I just leaned in and we had a very sexy little kiss.
We kissed a little more and I felt down and could see she was ROCK hard in her pants. She had tight leggings on, and it was hard to slide my hand into them, but my hand eventually made it's way to her warm hard curved cock.
We kissed for a bit then I said I was leaving ( I was tired n wanted to sleep). She said don't go and said we could go back to hers.
We got a taxi back to hers and fooled around in her bed, very passionate kissing and playIng with her rock hard cock.
I was too drunk and so couldnt ge hard, so I was sucking and wanking her to make her cum, and we were close, when her roommates knocked on the door.
It was 4 am and they wanted to sleep lol.
She let them in, and then I found myself naked in the bed with a ts, with 2 other ts sitting on their beds just chattin n flirting with me lol.
By this time I was just too tired and drunk n just wanted sleep,
So I got dressed and left.
Ahha as I woke up later that morning, I scratched my head and realised, I just walked away from a potential 4 way with 3 ts. Ahaha ah well

[Ibuymp3s]

Originally Posted by aussiepride

One time after a night on the town I was headed back home when I decided to go take a look in the taxi club in sydney.
I had a drink and was just walking around catching the gaze of a few ts when I locked eyes with a little cutie who was in the outside pockies section.
I just went over and said hi. Said she looked cute.
We chatted for a bit then I just leaned in and we had a very sexy little kiss.
We kissed a little more and I felt down and could see she was ROCK hard in her pants. She had tight leggings on, and it was hard to slide my hand into them, but my hand eventually made it's way to her warm hard curved cock.
We kissed for a bit then I said I was leaving ( I was tired n wanted to sleep). She said don't go and said we could go back to hers.
We got a taxi back to hers and fooled around in her bed, very passionate kissing and playIng with her rock hard cock.
I was too drunk and so couldnt ge hard, so I was sucking and wanking her to make her cum, and we were close, when her roommates knocked on the door.
It was 4 am and they wanted to sleep lol.
She let them in, and then I found myself naked in the bed with a ts, with 2 other ts sitting on their beds just chattin n flirting with me lol.
By this time I was just too tired and drunk n just wanted sleep,
So I got dressed and left.
Ahha as I woke up later that morning, I scratched my head and realised, I just walked away from a potential 4 way with 3 ts. Ahaha ah well

which 1s of them were passible, if any?

[aussiepride]

Originally Posted by Ibuymp3s

which 1s of them were passible, if any?

The one I met at the club was only a cd, but was very cute.
I'm a sucker for a cute face (great eyes and smile etc).
But yeah if I was sober I maybe would have played the field a bit more.
One of the friends was a insanely thin sexy hot thing that just made me crazy just looking at her.
The other I can't remember much of.

Stay tuned in this thread for some more stories with some very passable beautiful ts.
But does meeting online first count?

[rcurious]

I posted this in another thread, but thought it fit this subject and it might be of interest. This happened only a few days ago.


Early this morning when I was on the bus, a rather sleazy looking "working girl" got on the bus, probably after a long nights work. Something caught my eye about her and being the sleazy kinda guy I am, I summoned up enough nerve to go sit next to her. The bus was pretty empty and I was making some pretty big assumptions, but went for it anyway. I took a bill out of my wallet and sat next to her. I didn't say anything, but slipped the bill in her hand. She happily accepted. Then we proceeded to play with each other. She began to rub my hardon through my pants and I slipped my hand under her short skirt. My assumptions were proven correct when I found her bulge beneath her panties. She pulled her cock out from her panties and we played with each other until my stop. I'm such a slut.

[sammivalentine]

i thought i met one...... but it turned out to be my dad!!