Free Shemale Stories

It Was So Exciting

It was about 230 am Friday night when I walked into the Crypt adult book store on 30th Street in San Diego Calif. The Crypt's usual clientele was mostly gay men, and tonight was no exception. I felt my face burning as I walked back into the peek booth part of the store. These booths had no doors or ... read more

shemale lover January 21, 2012 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 more

Chrissy Tunnell March 4, 2022 100%

Uncles Ranch

My Uncles Ranch Its late May and school is getting out for summer break finally next year marks the start of college but who cares about that. I’m excited to do the basic summer fun like hangout with my friends go to movies and of course get in touch with my shemale side. When I get home my parents... read more

cdsissy18 March 2, 2018 83%

Lola Chapter 4

We sat at the table. I had made the effort to cook a small three-course French-inspired dinner. I was in love, but Lola’s mind seemed elsewhere. - How nice… She was chewing absent-mindedly. - I have to ask you something. - Shoot baby. Ask away! Lola looked deep into my eyes: - Could you ima... read more

BellaBeau October 30, 2023 100%

Lola Chapter 5

Lola chapter 5 Summer vacation was coming to an end. Most of the time we had been to ourselves, mostly at home but also a couple of shorter trips. Beer tasting in Stockholm's archipelago, a trip to the west coast, overnight stays in hotels, everywhere we were received like any other couple. A fam... read more

BellaBeau October 30, 2023 100%

Porn site meeting and fucking ;)

We started talking on a site. I knew you were for real when you sent me a message introducing yourself. We only spoke for 2 days before we decided to meet up and I was excited to play with a real little slut. You told me the only things off limit were anal and scat otherwise i could do what I wanted... read more

BalkanLoco91Ri August 26, 2019 77%

From accidental trans porn addiction to a cum filled booty

One night when I was around 30 or so I was watching some porn, nothing unusual for a guy like me, aka a sex addict. Sex addiction is great if you’re Tiger Woods and swimming in poon, but for guys like me - regular, awkward, slightly handsome in a very boyish way, weirdos — it’s not that fun. We... read more

CDJaneBooty April 1, 2022 100%

Mommy, can I be your fuck-toy?

I saw my step-mom taking a shower by accident or so I thought. It was not until I saw her pretty big she-cock jus hanging there between her sexy well defined legs. It was even hard & it was already as big as my cock when its hard. It looked so big that it was a bit scary yet some muscle in my anus s... read more

Curious_billy November 22, 2022 100%

A Fairy Tale Part 1

=-=-Chapter One-=-= "Heather?" My boyfriend was knocking on the bathroom door. "What's wrong, are you okay? Heather?" "Yeah..." I swallowed thickly and that was a mistake. I threw up some more, kneeling on the floor, feeling like I was dying. "Heather?&q... read more

shemale lover December 6, 2011 80%

Becoming Marie Chapter 3

On one of my bike rides and visits to the Transporter Bridge cottage I met a guy who told me of a cruising spot not far from there. He told me the place was much safer than cottaging, gave me directions to it and said it was always busy. The following weekend I set off on my bike wearing a loose ... read more

shemale lover March 22, 2012 83%

Sauna Special Services of a Kind

Sauna Special Service of a kind My name is Yaki, a shemale in Tai Chung, Taiwan. One Saturday afternoon, I dress in my usual lady costumes and go to the sauna parlor on Daya Road with my three CD friends. This sauna parlor is really gorgeous. It occupies three floors with over 20,000 ft in a... read more

retiler May 7, 2014 97%

Crossdresser gets dick for first time

I was so tired of just watching porn. So tired of the sissy hypno threads that made me crave men, crave cock, crave being weak, crave being the bitch...only to cum and do nothing about it. But the desire to transition from fantasy to reality was growing stronger and stronger. I decided it was ti... read more

Sissy Ava October 11, 2022 100%

Eric...a Part 2

I was well into my first semester of college. The University I chose was close enough to drive to, but my parents thought it would be a good idea to for me to live on campus. I didn't mind, and actually wanted some freedom. I lived in a single dorm unit and was not having a difficult time of transit... read more

shemale lover April 18, 2012 50%

Wanted

Not really a story, more about what I want. I am a Bi curious guy. I love pussy, but I really like cock. What I am looking for is a smooth feminine guy or tranny that would let me use him/her for an experiment... an experiment to see how far I'll go. First, I would like to meet in a neutral pl... read more

shemale lover June 2, 2012 60%

SissyRayG at the Roadside Reststop......

Last year I was traveling by car on business between Saskatoon and Regina, Canada. I was looking for a roadside rest area to use the washroom. I had all my sexy lingerie with me and hadn't had a chance to wear it for days as had been way to busy at work. I saw the roadside rest area I was looking... read more

shemale lover July 3, 2012 70%

Crazy dreams

I met Dave about 2 years ago at a swingers party. I had just turned 18 and he was 43. I remember thinking that it was hot that he was exactly 25 years older than me. I was dressed in drag and he was into t-gurls and he was married and hung like a horse and I happened to be into partying naked with b... read more

shemale lover July 11, 2012 100%

Random Thoughts, Desires, Dreams & Fantasies

It's like I knew she had a cock but after meeting her & seeing how fkn gorgeous she is, you tend to forget real quick that the kCraigslist ad said she was packing & this being my 1st time ..... shit, maybe I outta just make up an excuse & back out now before .... Yes, back out now ... read more

Curious_billy July 5, 2013 100%

Best booty i ever had

there is a certain part of the big city where the community partys everyday of the week called boys town i worked in the area and never knew but what i did know is i had a fetish for an extremly large ass i love big bootys and desired a tranny after watching shemale videos this didnt happen until i ... read more

jrryder December 8, 2013 88%

Her Name Was Amber

"Hey," I said as she slid into the barstool beside me, I had been throwing them back all night. "What's the problem?" She asked a smile dancing on her lips, "Nothing, I just don't want to be me right now." "Who do you want to be," she asked with a ... read more

Iced5 February 8, 2016 100%

Fucking Outside with a Crossdresser

I was on CL the other night checking out ads. I came across one by a CD. He wanted to fuck Bareback outside by the front door of his apartment. It sounded hot, He told me it was dark and no one could see us. I imagined a porch with no neighbors near by. I get there and is a regular house in the subu... read more

horny.hiker July 25, 2017 62%