Shemale Stories

Another lovely short shemale story from our forum member, this time from a guy who calls himself “I Fucked A Shemale”

I was at my best friends house a couple of years ago. I was maybe 18 i believe. His step mom was there. Well his new step mom that his dad just married like a few days before. Well I had to go to the bathroom, so i went to the bathroom. I had walked on in and then i heard the shower on. It was his step-mom. She told me dont worry to come on in. So i came on in sorta not wanting to. Only because i was a virgin either way and i was still insecure about my self. So i just decided to sit down and pee. I was there and my eyes started to wander. I then started to look behind the curtain. Then I saw her standing there. She was wet and i could see her nice ass. So I got hard and started beating off. Then all the sudden she turned around and saw me there beating off.

My First Shemale Sex - read the full post…

• How Macho became a shemale lover
• Giving shemale a blowjob for the first time
• My first time with a shemale escort

Our new forum member who calls himsels BigBell609 has recently visited Moscow and obviously had some fun time with Russian shemale escorts. Now he wants to share the juicy details of his fun time in Moscow. I know, you’re going to like that

The first day, I was with my Russian friend, who introduced to me the Russian shemale escort. Since I know he is a big fan of shemales, so I wasn’t shy of asking him about shemale escorts in Russia. He called in a shemale escort for me rightaway. I was staying in a hotel in downtown Moscow. Since my company paid for the expenses, I was staying at a quite nice 5-star hotel.

Soon (about forty minutes later), someone was knocking on the door. Then came in this astonishingly good looking lady. My friend talked to her briefly in Russian. Then he turned to me asked me to give her $$$ (apparently she did not ask for Russian money), which I happily complied. My friend waved to me goodbye and he went out of the door. To tell you the truth, I was extremely nervous. I have been to other shemale escorts before in the States, and not being this nervous. In fact, if some of you have read my other post, you know I had a shemale girlfriend a few years ago. Well, maybe because I was in a foreign country.

Fun time with russian shemales in Moscow - read the full post…

• My first time with a shemale escort
• Shemale cum in my pussy
• Tranny Lisa’s first sexual experience

Tonight our reader Tommy is willing to share some juicy details of his latest shemale incident. I was pretty amazed my the variety of positions they tried and can only regret it was not me there with that beautiful shemale Andrea.

I checked in to my hotel and checked into the excellent vicesisters.com website and searched for shemales in town. I happened across a lovely shemale Andrea and called her on the phone and made a date. She sent me a text saying that she was in a taxi and would be at the hotel in just a few minutes - could I meet her in the lobby and I’d recognse her as she was wearing a yellow blouse. I’d showered up and headed down to the lobby. I saw a taxi pull up and saw a yellow-bloused goddess pull up, but my heart sank - surely she couldn’t be a shemale - she had to be a genetic girl. Now, I know shemales when I see them. I couldn’t believe that somehow I’dd gotten my wires crossed and hooked up with a straight girl. But I still went up to her to say hi and to sort things out, and yes it was Andrea. Even her voice was 100% female - I was totally confused at that stage.

Anyhow we got to talking and she asked my why I liked shemales. Bingo! She was so 100% gorgoeus I couldn’t believe that she’d have a cock under those jeans, but I had to suspend my normally reliable shemale-radar. We got to my room and chatted for a while before she pulled off her yellow blouse, revealing a strapless black bra that held the promise of luscious lickable size 36 boobs - silicone enhanced as she told me later.

My latest shemale incident - What a great fuck! - read the full post…

• My first time with a shemale escort
• Shemales Fuck Shemales
• Ladyboy passionately screws a guy

This lovely shemale story was written by our dear forum member Cham and, although he claims it to be a work of fiction, the plot is very vivid and realistic. It’s a story about a macho-man Jake who lost his shemale virginity with a beautiful Leona. Thank You Cham, it was a very successfull first attempt at writing and I believe many more people will be able to enjoy your story now.

I think of myself as resolutely straight. I look at a lot of porn although I have plenty of girls to fuck. Steven, an old college buddy, dropped by and proposed that we go to a shemale bar that night. I was shocked and refused. But Steven retorted that if I was sure about my sexuality, I should have no problems being there. I could just have a few drinks, take in the scenery, and after we left we could pick up a couple of hookers for a blow job or a fuck.

We got there quite early and I parked myself at the bar, and watched the talent coming in. In spite of myself I was amazed that some of them looked so hot! I would normally have been hitting on them, but I had to remind myself, that there was a cock between their legs! They flowed in, in all shapes and sizes, mostly heavily made up and wearing skimpy outfits that left very little to the imagination.

Many were dancing, some with other shemales, some with the punters who had come in. I watched, and after a couple of drinks when the dancing started to get dirty, I found my cock stirring. After all, I thought to myself, I could just fuck one of them in the ass, and even get a blowjob.

And then she walked through the door. She had big eyes, a pouty face, huge tits, and an ass to die for. She wore a black item that barely concealed her tits and ass, and ultra-high heeled stilettos. She caught my eye as she entered and smiled at me. I just knew that I had to meet her. She was now at the bar, and like all men, I rushed up to offer to buy her a drink.

Leona - read the full post…

• The first shemale experience: Balls deep in ass
• Jog In the park
• Party with my best friend

This hot shemale story was sent to me by our forum member Leeya and i’m anxious to share it here with everybody. It’s a classy story about a guy who went to an Asian country on a business trip and met a very beautiful womain in a very romantic atmosphere… Little did he know that this young voluptuous lady was a ladyboy.

Thanks for this story Leeya. As a reminder to all others, if you have a story suitable for this section, by all means post it either here as a comment or at our forum, and i will publish it for thousands of other readers to enjoy.

Disclaimer: all the characters and events are made up, similarities are coincidentail. No intent to offend anyone.

You were still eyeing your new Swiss wrist watch which you just purchased from one of the duty-free shops at your local airport. You glanced outside of the window, where the blanket of clouds was covering beautiful lands. Staring at the clouds, thoughts about upcoming presentation and potential questions that could arise were targeting your mind. It’s been only 6 hours after you saw your wife and you were already missing her. Her beautiful eyes, body: Oh how your heart was always up beating when she was smiling at you.

A slim stewardess interrupted the thought process with a question of what would you prefer today, chicken or beef. Slowly chewing pieces of chicken, you could not help but thinking how important securing a major contract with investors from Asia was essential for your company’s future, but you are a professional, you knew you would do the job. Success- and you are the new CEO, failure- well, you’ll be stuck with your job for few more years.

Upon arrival to the airport, getting the luggage and catching a cab to 5star hotel, your head was pumping with all the thoughts and a terrible headache. The moment you put your head on the pillow it was all gone away, and your mind went into its own world of dreams.

Thank you for Paradise - read the full post…

• Got dominated by 2 shemales on the last day in Thailand
• My first pre-op story
• Ladyboy Surprise - Part 2

It’s been quite some time since I posted a new shemale story here. Hope all of You who have experience with shemales will finally have some courage to write about it and share it with us. Let this sizzling story by Tommy be an inspiration to You. Who wouldn’t want to be in his place in this crazy foursome?

I gotta tell you about a great night at Nana Plaza a few months ago. I’d called into a few bars and almost hooked up with a hot looking Tgirl from Casanova, but felt like getting some fresh air. I wandered around Nana and was thinking of heading home when a muscly Korean guy - first time there, asked me if I would show him around the place. Well, it’s almost my home away from home so I said I would have a beer or two with him and show him the ropes.

Foursome with two ladyboys - read the full post…

• Got dominated by 2 shemales on the last day in Thailand
• Jog In the park
• Two cock-hungry ladyboys team up to fuck one guy

Just another little log of a hot chat… Reading it gave me a boner, and i’m sure so it will to you!

Judi: Hi Sheri, I'm Judi.
sheri: hi
sheri: how are you
Judi: Good Sheri, how are u sweetheart?
sheri: i'm good and horny
sheri: what are you Judi
sheri: you a ts
Judi: I am TS originally from the phillipines.
Judi: Are u a TS?
sheri: mmmmmm
sheri: how big are you
Judi: 9" - it is the only thing big about me, I have small tits.
sheri: thats ok i have big tits and a wet shaved pussy
Filipino TS with a 9 incher in our chat room - read the full post…

• Two tgirls chatting
• Threesome in our chat room
• In love with Sasha Davidson

If you’re married, you still can get some nice shemale cock to suck, even if this only happens in our chatroom. Who knows, perhaps a beautiful horny tgirl awaits you on the other end of the line right now stroking her hard shaft and waiting for someone to fuck! See for example what happened to this guy, jojo

jojo: any ts here?
Allyssa: ooh yes
jojo: u ts Allyssa?
Allyssa: tg
jojo: u look hot 4 40?
Allyssa: growing boobs with nice cock
jojo: u have a cock and boobs?
Allyssa: mmmm
Married guy sucks a shemale cock in our chatroom - read the full post…

• Threesome in our chat room
• Filipino TS with a 9 incher in our chat room
• Are you ready to take your wife’s dick?

Our reader Tommy writes about one of his adventures with a shemale. Sure, it turned out to be not as romantic, but, as he says, nevertheless it was a good hardcore fuck! Thanks to him for this great story.

One night on biz in Vancouver I saw some adverts in the paper for shemales and got hot and hard just thinking about it. I called up one Tgirl called Fumiko who had a husky sexy voice and chatted for a while and we made a date. I took a cab round to her place and knocked on the door with my heart beating doubletime. She answered the door and took me by the hand and lead me into her bedroom. She wasn’t such a hot looker - flat chest and a bit manly, to tell the truth, but at that stage I was past caring. She had a nice room and some hot shemale sex was playing on DVD. OK, I was in.

Good hardcore fuck with a shemale from Vancouver - read the full post…

• Always Wanted A Shemale
• The first shemale experience: Balls deep in ass
• I recently visited a shemale

I was going to publish this story tomorrow but i just don’t seem to keep this only to myself and the forum members. This is another story by tgirl Fran and oh my, she does know how to write! This was one of the most vivid and romantic description of 69 sex i ever got to read! I bet you will agree with me after you read this story!

It has been a nice evening out. Ila took me out for fine dining. I like getting “dressed up” and enjoy fine meal in places with a romantic atmosphere. It’s good for the soul to elevate oneself to a higher standard. Good food and good company is always a reward.

We get home early because we started early. We get to choose the corner table when we do that. We enter the house and I take Ila’s jacket. He also kicks off his shoes. I have good carpeting. I appreciate that. Yeah, Ila is house -broken. LOL I put on some slow dancing music and Ila knows what I want. Holds me in his arms and we slow dance. We’re good enough at this that we can stay off each other’s toes too. I loosen his tie and pull it off. I’m in my blue satin evening dress. It’s soft and smooth, slippery as ice. We dance and whisper those sweet nothings that lovers do. He pulls me in close at the hips. ” I get the message Ila.”

Out and all in - read the full post…

• How I make love to my shemale
• Two tgirls chatting
• My first pre-op story