Free Shemale Stories

The first tranny I looked for

So i've had some tranny experience unwittingly. I respond to this ad on craigslist from this 19 year old tranny who lives fairly far away, but her picture was so sexy I decided to take the hour drive. So I drive to her parents house, nervous the whole way, when I get there I get out of the car. Ston... read more

shemale lover November 4, 2012 88%

Amy The Tranny Part 1

I met Amy at an adult theatre in town. She was dressed to nines in a mini skirt, tight halter top, and pumps leading up a pair of fishnet clad legs. I invited her into a private booth and once inside, went over her price for some adult fun. She told me I couldn't fuck her as she was on her per... read more

shemale lover December 14, 2011 100%

Tranny sex

I dressed in her bathroom. Comfortable nylon stockings and my black body with suspenders, black thong, my beautiful silicone breasts in C-cup and between blond wig with ponytail up on my left shoulder. High heels had to wait this time. Then I pulled on my red short dress in jersey. He who runs away ... read more

shemale lover May 19, 2012 0%

Sex with a cab driver in my hotel room

After spending about a week with a client in the exotic locations of Kerala backwaters, I was sitting in the flight from Cochin to Bangalore. Though I had an awesome time with my businessman client in Kerala, I had already booked my hotel room in Bangalore to meet my regular clients as well as the ... read more

Manusha Tranny October 14, 2021 71%

My first shemale sex

I had developed a strong desire to be with a hot looking shemale for a long time. I really did not know how to make contact with anyone in the small city I lived in, and figured it would likely never happen to me. One day at work at my computer support job, I was informed that another branch of our ... read more

shemale lover July 17, 2013 94%

My first shemale sex

I had developed a strong desire to be with a hot looking shemale for a long time. I really did not know how to make contact with anyone in the small city I lived in, and figured it would likely never happen to me. One day at work at my computer support job, I was informed that another branch of our ... read more

shemale lover August 14, 2013 90%

Singapore tranny sex

My ship was dry-docked in Singapore for 3 weeks, n i was lucky enough to meet a gr8 girl first nite ashore, Lin, half chinese/ half malay, n fucking sexy. I slept at her flat most nites and the sex was awsome. She shared with a girl called Meena, a hostess on Singapore Airlines, but until this speci... read more

shemale lover November 20, 2011 75%

That ass was amazing

another adventure from fb i met a friend thru a relative only thing is he was playing and i was not he asked me if i would fuck this girl not to attractive but with the kind of ass i like plump,juicy u see i,m strictly top and i luv to fuck expecially ass,the bigger the better so i sent her a friend... read more

jrryder February 18, 2014 45%

Once Upon a Tranny

Bob was having a time with the winter traffic. It had snowed last night, the roads were slick, and all too many people were driving like they had never seen the stuff before. He had started out early in what turned out to be a vain attempt to get to the office on time. Conditions were worse than he ... read more

shemale lover October 30, 2011 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 more

My Shemale Attraction January 3, 2023 100%

Daddy always wanted a little girl

I SAW my daddy and his friends fucking a tranny one night and the next night he had a poker party. SO I got some of the sexy clothes he had. MINI skirt black lacy crotchless bodySUIT heels, wig makeup, EVEN IN my wheelchair, I LOOK LIKE LIKE a whore. Toward the end of the night I rolled out to drive... read more

shemale lover May 21, 2012 100%

The Seductive Seed of a Tranny MILF

The Seductive Seed of a Tranny MILF SugarandSalt Jackson got home and immediately curled up in bed. He didn't want to move for the rest of the weekend. He'd finally worked up the courage to ask a co-worker out at work. She politely rejected the invitation. Then later on in the day, Jackson spo... read more

Gwapo67 May 3, 2022 100%

My favorite time with a man as a Tgirl

I was in the dance clubs with my friends and we were very sexy dressed in heels and low tops and I was in high heels and a mini dress that was flowers all around it. My ass looked so big and round in that dress. It was low on my big boobs and very tight so my boobs looked like they have coming out. ... read more

shemale lover September 29, 2012 100%

My Boss And His Porn Shemale Video

A while ago, I started working in an antique shop. My boss was a bit older than me, but very good looking. I noticed that he was flirting with me occasionally and I have to admit that I liked it. I didn't want to encourage him, because I didn't know how he would react when he finds out that I'm a sh... read more

shemale lover April 18, 2016 84%

A One Night Stand for Tranny G

The time had arrived for me to travel to see Tranny G, yet something felt different. I mentioned that HE is a soldier and really, I was never angry about the rape. It was such an experience, that I wander back to and repeat in my mind again and again, wet with the memories of the fear, the fight, th... read more

shemale lover April 30, 2012 40%

Shemale fun

Recently I've been chatting with a very feminine and beautiful shemale named Lisa. We've been trading photos and dirty talk over chat lines and emails. I've always fanatsized about a cick with a dick and unexpectedly the opportunity came that we could potentially meet. Being married I had to conc... read more

shemale lover November 25, 2014 96%

Shemale fun

Recently I've been chatting with a very feminine and beautiful shemale named Lisa. We've been trading photos and dirty talk over chat lines and emails. I've always fanatsized about a cick with a dick and unexpectedly the opportunity came that we could potentially meet. Being married I had to conc... read more

shemale lover December 3, 2014 80%

A Reluctant Gang Bang

Hi all! I have been cross dressing and playing with men for many years now. One of My first experiences was being gang fucked by about 9 guys at an adult arcade. I was 18 at the time and it kind of traumatized me as it was pretty much a gang rape at an adult arcade. I was dressed up in a white flowe... read more

shemale lover May 28, 2012 100%

Sex with strangers in public bathroom

I always had a sexual fantasy of dressing up as a chunky sexy slut tranny and visiting a known public mens bathroom close to my house and giving oral sex and what ever they wanted me to do for them sexually.Well I finally got up the courage to do it and before I go into my true first time experience... read more

shemale lover October 1, 2012 100%

Why TS Gurls are Better

It was going on 2am and me and a friend had just left another bar and ended up at one of the last clubs open in the city. I was pretty intoxicated and tired of walking around the city. I bought an energy drink at the bar and sat on a near by love seat as my friend danced with a couple blonde girls w... read more

shemale lover October 27, 2012 100%