Free Stories

80%
My Shemale experiences
I have had experiences with Shemales. All in Hawaii. Three different ones. I met them all through yahoo chat when it was still fairly popular. In the 1998-2000 time frame. The first one I met up with was doing video shows in some back area part of Honolulu. She agreed to meet me as long as we only h... Read full Story
89%
My first shemale experience
So before I was even into the porn I had my first experience. I was 25 years old and never thought about anything like this till it happened. I was out with my friends one night hitting the usual bars on the weekend when this hot young woman caught my eye. I was feeling pretty brave due to my "... Read full Story
94%
My first Shemale
“Curious? Bi?” Well, yes, but only with a shemale. Beyond that I’m a firmly planted heterosexual. For many years I longed to have sex with a shemale but never did anything about it. (I’m not much of an initiator). The community I live in has lots of shemale beauts; maybe that started my intere... Read full Story
100%
Santa Likes Shemales Femboys
Did you know Santa Clause is real....and he likes shemales femboys??!I It happened last Christmas Eve. I fell asleep watching the snow fall just outside my window. I was comfy under my layers of warm blankets I clutched tightly, in the black lace panties and red lingerie night dress or nighty I wear... Read full Story
100%
Dating my Sissy-sister (English)
You are wearing women's stockings and a thigh-high transparent top, the thin shoulder straps of which leave your arms and shoulders elegantly exposed! You're the real lil bunny to me in that girl outfit of yours... How about, should I teach the little one about the naughty girl? You're giggling a... Read full Story
75%
Amy Finally Lives Out Her Fantasies Part 2
"Wow! What got into you?" "I don't know, I just decided to finally loosen up and go with my desires," she explained. "Did you enjoy it?" "Are you nuts? I LOVED every second of it!" I exclaimed. Figuring the alcohol played a very large role in her sudd... Read full Story
87%
Summit
"How many nights will you be staying with us, Mrs. Gentry," asked the young man behind the registration desk? "My husband and I will be staying at least two nights, maybe more," she replied, while her husband Carl stood quietly at her side! "Would you like me to call you a b... Read full Story
94%
My first shemale
This is the story of my first she male. I had always been curious about dicks. I had always been attracted to women and I loved to watch a woman get pounded by a big cock. But after awhile I realized that when I tried to imagine the porno, I always imagined myself in place of the girl. One day, when... Read full Story
94%
SheMale Encounter
“Promise not to fall in love while you’re away?” Lana asked as she wrapped her arms around me. “I’ve told you several times already,” I snapped at her. I had begun to get more than frustrated with her. “This is just a business trip and nothing more, besid... Read full Story
96%
Trisha
The doorbell dinged. It was my next door neighbor Pete. I had known him since I moved into these condos two years ago. We met at one of the monthly parties our association throws. That one happened to be a barbeque and I remember the dish he brought to the potluck was amazing. Pete was always trying... Read full Story
91%
MY FIRST TIME WITH A SHEMALE
I`ve always had this fantasy about being with a shemale,i guess something about a chick wit a dick and tits always turned me on,i`ve always been curious about wat it`s like to be fucked by one.Well last weekend was a weekend i`m gonna remember for the rest of my life bc that was the weekend i decide... Read full Story
78%
Once wasn't enough!- my 2nd shemale exp
So after my first experience I got really into the porn I bought movies magezines got on websites just couldn't get enough. But watching it wasn't enough I had the real thing once and wanted it again. It had been almost a year now and only one person knew about what I had done that one fat... Read full Story
100%
CD/TS Shemale Chrissy Fucked On the Ranch
I met John on the swinger site AdultFriendFinder. He was everything I was looking for: old, in his late 60s, and not rich, but financially stable and independent, owning a ranch that has been in his family for generations. Maybe he could become the Sugar Daddy I am looking for? I am a shaved-smooth ... Read full Story
100%
Why I desire transsexual cock
I've thought about what it must feel like to have jus for a bit, a transsexual cock inside you. How ones nervousness is turned into extreme horniness upon seeing her cock for the first time. The thoughts that must race thru your head. How big is her she-cock?. Do I touch it? Do i lick the length of... Read full Story
92%
Real Story with a Shemale Escort
One day I dreamt about a big black cock fucking me on doggy style. The dream felt so real that it made me to ejaculated in my sleep without even touching my cock. It was the first time this happened to me and I was surprised because I’d never felt gay. My underwear became a mess filling the whole su... Read full Story
94%
Deep Throating Shemale
Yvonne is one of my best friends and we do more than just hang out at the local nightclub. She has long wavy black hair and dark violet eyes. Like me, she is also a pre-op transsexual, which means she has breasts and a penis. In the few years that we have known each other, she has taught me a lot ab... Read full Story
86%
Giving shemale a blowjob for the first time
I've been fantasizing about a shemale cock for a long time. Get me right, I am a straight man and all, but somehow the idea of sucking a girl's dick always turned me on. I'm not a big fan of anal sex and I don't think I'd love someone's cock in my ass, I'd rather prefer to give shemale a blowjob. ... Read full Story
81%
TV loving cock
Sorry I didn't keep you posted on Saturday night, but I was sorta busy being my usual slutty self. Story to follow: I talked to a guy on megaphone. He works as a night security guard at a big office building on the edge of town. He is there all by himself in this huge, mostly vacant building, in ... Read full Story
58%
Porno Mobile Shemale Video
I have been always turned on by shemales, but somehow I couldn't find any that would like to be with me. That's why I was always watching shemale movies and I even had several porno mobile shemale videos on my android. I was always fascinated by the fact that I could sleep with shemale and touch her... Read full Story
40%
See Me At Shemale Cam Tube
I was dressing when I heard a new e-mail arriving. "You're hot as hell on Shemale Cam Tube", he wrote, "Wanna meet me 4 lunch? Promise to be a gentleman!" It was cute, especially coming from such a skinny guy. I'm a big girl - over six feet, with strong legs and huge breasts whic... Read full Story
84%
Fucked by a Shemale
My names - and I would like to tell you about a very sexual experience I had recently. First I would like to tell you I’m 30 years old and never had a gay experience, until now. It was a Saturday night, me and my brother were round the local town, after a few too many beers my brother met a bi... Read full Story
38%
From Gloryhole Peegasm to Shemale
I was in a porn video booth. I young guy stepped into the next one. I was already jerking my small dick, but he didn't even pull his pants down. He asked me if I wanted my dick sucked. Actually I think he said something like, "hey, let me suck your dick." Recently I had let some weird, ... Read full Story
100%
by a Shemale Part 2
I was awaken early Monday morning when Felicia lightly kissed me on the cheeks and said it was time to start my hormone regimen. I looked at her and she had her left hand opened and she had a white pill and in her right hand a glass of water. I was no longer fighting or resisting especiall... Read full Story
78%
My Shemale Stepmother Part 2
"Not yet, bitch. You've got to beg for it first," she slapped my face with her semi hard cock, "Now, tell me what you want." "I want your cock, mistress," I said wimpily. "What do you want to do with it, slave," she slapped her cock across my cheek again... Read full Story
66%
An Ass to Die For
It's a very strange thing. We all have our personal quirks. The things that make us unique and stand out from the crowd. I've just never met anyone besides me who has mine before, and to tell you the truth I'm not sure if it's a gift or a curse. You see, I have a girl's ass and not just any old girl... Read full Story
100%
Male or Shemale, Still a Slut
Part 1 My name is Brandon. I'm 18 (still in high school), 5'5", white with black hair, and rather feminine. I'm really slim with barely any body hair. All this has combined so that I'm not so popular with the ladies, which sucks cause I am one horny son of a bitch. Luckily, I'm rather fond ... Read full Story
88%
Oh My, You Have a Cock...
It was a regular Friday night no different from others I'd experienced before. I was lonely having broken up with my girlfriend earlier that week. What a bitch! I needed to find me a sweet woman capable of matching my libido. My last lady was all about the lights off, missionary position sex, come t... Read full Story
83%
MY FIRST TIME WITH A SHEMALE - 2
DEAR READERS I DON’T KNOW IF YOU LIKED MY FIRST STORY AS THERE WERE NO COMMENTS ........ !!! After we finished our late dinner in the very cosy position she whispered “wanna have some wine honey?” I replied “I’d love to”. She got up leaving me sitting on her bed and poured two large glass-full of... Read full Story
64%
Big Cock Heaven
This story is written from the Shemale's point of view. "Jane" is based on a real Transgender woman from California & my friend. She gave me the outline of a meeting she had with "Janardhan." ***** My name is Jane and I am a natural red head blue eyed 34 year old T... Read full Story
50%
The BIG COCK that I will eat.
ENGLISH: Hello friends. In the link below, you can see the tranny cock that will fuck me in the days to come. I saw her advertised on the internet, I picked up the phone and called, I will see her when her clinical tests are negative for sexually transmitted diseases, because I will surely swallow... Read full Story
100%
Got my ass pounded in Miami by a tranny escort
Got my ass pounded in Miami by a beautiful tranny escort with a 10 inch thick cock. Years ago I was in Miami for a business trip. Four days just me in my hotel room. I decided to treat myself to some of the X rated channels that my hotel provided. As usual I went straight to the tranny porn.... Read full Story
100%
First time with big surprise
My first story translated into English, I hope you like it. It was late at night, I had been drinking with friends and was on my way home. I am a man in his early 30s, smartly dressed and looking quite attractive. The night was beautiful, clear sky, warm and in the city were some people on the ... Read full Story
100%
Hung Shemale has Motorcycle Trouble near Vegas
I drive down a deserted two- lane highway outside of Las Vegas, Nevada. It is August and the temperature is well over 100 degrees. In the distance, I see a tall beautiful mature creature that walks alongside the road. As I pull over, I am stunned by her powerful physique. She sports an incredibly ti... Read full Story
80%
A succulent shemale cock in my mouth
Not only the readers of our ladyboy blog love jerking off to our shemale sex stories, some of them are also willing to share. A guy named Steve was always curious about how a shemale cock would taste in his mouth and he just had to let it all out. TFS, Steve. I have always wanted to know what it ... Read full Story
68%
Shemale Porn Photo On The Wall Of Her Room
She was a truly hot shemale that I’ve been seeing for a couple of months now, from time to time. She had some really big tits and a dick that didn’t really get in our way much. It really wasn’t all about the sex. I loved talking and even cuddling with that girl. We talked about ... Read full Story
87%
Shemale First Time
First time Sex with a shemale. Intro. I have read several stories of first time sex with Transexuals and none relate to my experience. So for those who are truly curious about how to go about it and what it is like this is my tale. I have always been a straight guy as far as I know. Married... Read full Story