Any guys remember there first time with a TS???

[business man]

Anybody got some good stories on there encounters with a TS by mistake or on purpose and went through with it

[Raging Bob]

I'm betting every guy here remembers his first time!!

[Ray]

I don't remember the date (maybe 12-14 years ago). I was in Vegas for a convention and decided to take the plunge. I saw an ad for a Hawaiian girl that appealed to me. I knew she was a couple inches taller than me but the ad said she had a 6" cock so I knew I wouldn't we terribly outgunned in that dept. I of course was extremely nervous. She showed up at my hotel on time and when I opened the door there she was towering above me in her 5 or 6 inch heels. Needless to say I asked her to remove them immediately. She was not a skinny girl, probably weighed about 160#. She was very sweet and liked to kiss. My big surprise came when she took off her panties. 6", I think not. Her dick was thicker than mine(kind of cone shaped) but I was quite a bit longer than her. She did get hard but because of the shortness, she could not penetrate me. All in all a good time. It must have been a good time because as you all know, I have been hooked on TGirls ever since. Thank you Olivia.

[the_conqueror]

My first time was with Lucy.

She plowed me pretty good

[Ray]

I didn't know Lucy was a farmer, LOL.

[TheDon]

My first time with a shemale felt so surreal and out of this world that it still keeps me going back for more.

I'd have to say that my first time with a shemale was more intense than my first time with a genetic girl. But I love them both!

[doorman]

My first time was with a lady named Monique she lived off Jarvis closer to dundas if i remember right.The first time i called her from a pay phone on jarvis she didnt answer so i started calling other ladies in eye it just so happened to be the phone she used for her "second" call it was around midnight so she drove over to see if it was a regular she called me over to her car invited me into her car we talked for a few min made out but she said she was tired but to call her in the morning so i did and the rest is history i was 18 at the time

[pornfan83]

I remember my first encounter with Transgender lass she lived up the street from me in Hollyweird,California.This was in 1993 she's was wainting on a friend that was extremely late picking her up I guess she getting ready to out clubing,for some reason she was waiting down by my apartment I started hitting on her.She went on to tell me that she was wainting on someone,so I said okay no problem.I then proceeded to go shopping at my local grocery store at time it was Mayfair Market and when I came back from shopping she was still waiting.So I hit on her again this I got lucky.We went back to her place and had a great time.Afterwards she got in contact with this friend of hers that she was waiting on.I ask her if it's okay for me to turn the TV I wanted to watch the rest of Saturday Night she let me and she noticed Madonna was performing and ask me if I like I said I could take or leave her.
Her friend eventually arrives she gives me her number we hug and I go on my way.
I had a great time with her so of course I call her again and she was extremely happy to hear from me.When I arrived at her place she was all serious I have something to tell you "I'm not a real girl" that's how she pharsed it and showed me her dick.To breake the ice I told her I kind of got that impression when your friend arrived.She was fine her friend on the other was not passable to be polite.We ended up having another great time together and we became very close for quite a while and quite a few great together.I do have many fond memories of her.

[Raging Bob]

Great rundown Pornfan....

[sniperki]

Strip club

It was on my 19 B-Day friends took me to a strip club. I saw this girl who I thought looked like a tranny back then I only saw trannies on the internet. My friends saw her and were calling her names. so at 2am when everyone was leaving I ditched my friends and talked to the girl. Her name was Cara. She said my friends were assholes. I ended up taking her out for a pizza. My friends were calling me like mad men so I turned it off. We went back to her place and talked had a drink. I was so nervous at the time I was talking so much drunk as fuck to I might add.
She had A big C cup tits and about 105lbs, black hair and brown eyes tanned skin..beach type of look.Next thing I new she was in just a bra showing her 3 inch cock. It was small penis but I liked it. We rubbed cocks and 69 for a bit. Then I came in her mouth when she was on her knees. I got hard right away and she put a condom on my. She bent over showing me her pink ass. I fucked her butt hard she told me to stop a few times cause she hadn't bin fucked by a straight guy in a while. We both looked at my cock in her ass and laughed. I stayed over and we fucked for 2 days drinking and partying...I still see her to this day.

[joedaddy]

Awesome story sniperki.

[interesting]

That awesome she is hot!! Wish that could happen to me.

[sniperki]

Awesome story sniperki.

That awesome she is hot!! Wish that could happen to me.

Thanks Joe...Yeah Interesting it will happen to you keep your head up!

[UnsulliedToast]

Was in Montreal at about 3:30 am. She took me back to her place, and I really don't remember much after that. I had been drinking most of the day, and all i could think was how hot her place was. It was almost too hot that I couldn't really enjoy myself. But, she was nice and said she posted on shemale Canada but I can't remember her name.

[maddplotter]

Was in Montreal at about 3:30 am. She took me back to her place, and I really don't remember much after that. I had been drinking most of the day, and all i could think was how hot her place was. It was almost too hot that I couldn't really enjoy myself. But, she was nice and said she posted on shemale Canada but I can't remember her name.

So was it a business transaction or on her own personal time?