Free Shemale Stories

My Girl Friend and A Shemale

I walk up to the door of my girlfriend’s apartment. As I start to slide the key into the lock, I can hear slight muffled noises from inside. As the door slowly opens, I am met by the sight of my girlfriend laying with her legs spread wide open on the couch and her super sexy friend Shayla, w... read more

tgirlloverme September 7, 2011 100%

Caught!

Let me start out by saying that I was very much in the closet about my dressing and the fun I have when I'm dressed when this happened. But more and more I kept fantasizing about one of my male friends. He's very good looking and keeps in shape by jogging every day. Several of the times we've gone o... read more

shemale lover June 7, 2011 100%

The lover of Lisa

It wasn’t that hard making the change from friend to lover, and from lover to student of sensuality. Lisa made clear that I was to follow her directions, not that our relationship was predicated on that, but that she was going to lead me to a new place in my life. She had been a friend for mo... read more

shemale lover January 4, 2018 100%

Foot Massage by a Shemale

My wife and I had just finished a nice Sushi dinner in an upscale restaurant outside of LA, with an old college friend of hers. We strolled down the boardwalk and were almost past an asian style massage spa, when my wife said why don’t we take advantage of their 45 minute foot massage for $... read more

shemale lover May 12, 2018 100%

First time

For as long as I can remember, I've preferred my chicks with dicks. There's something about a sexy babe with perfect makeup and hair and a cock that just turns me on. Maybe that makes me a pervert - I don't care! I remember I was just out of high school, 18, the first time I made it with a tran... read more

shemale lover August 14, 2011 100%

His Perfect Shemale Partner Part 1

I am in senior year of school and anyone who has been to school at 18 will know it is not a pleasant time to be working when your friends are all out drinking and enjoying themselves but I needed to go back to school to go the university I wanted to go to. I am a tall fairly muscular straight guy wh... read more

shemale lover August 28, 2011 100%

His Perfect Shemale Partner Part 2

Quite a few things have changed since the last chapter. OK maybe not that many, I am still lusting after Sally's body needing to have my dick in her and feel her in me, but we are a lot closer now as we are living together. Sally has gone to her 1st choice University and I decided I would rather get... read more

shemale lover August 28, 2011 100%

A good first time Part 1

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 more

shemale lover August 30, 2011 100%

My Surprise

Here I was in another strange town; the hotel was as usual just one of Those places you sleep in and I was bored and fed up with travelling A drink I thought I need something to relieve the boredom. An hour later I was in a bar in now what was the name of this town ?, Drinking alone in the corn... read more

shemale lover August 31, 2011 100%

The Sexiest Shemales Part 2

Holly and I didn't want to waste our day so got up and got ourselves in the shower. We stripped off our g-strings that we were still wearing from our sex fest and turned on the hot water. We always shower together. Sometimes we will fuck each other in there or suck each other off but we just had sex... read more

shemale lover September 3, 2011 100%

A Shemale Vacation Part 1

I was eighteen, naïve and horny. After graduating from school a group of us decided to head to Europe for a last trip before having to enter our real adult lives. It was a chance to get completely drunk and have lots of wild sex. At least, that was the idea in our simple teenage minds. As for m... read more

shemale lover September 5, 2011 100%

A Shemale Vacation Part 2

We sat there staring despondently at the ground. We had searched through all our bags and pockets and had nothing like the money we needed to pay for the hot sex sessions we had each enjoyed with the hot, hung Dutch whore. The guy, the pimp, who had previously been all smiles and friendly encouragem... read more

shemale lover September 5, 2011 100%

Shemale Fantasy - Suck Fest

This story is completely fictional - in fact it is a fantasy of mine that I will describe in great detail, contact details are at the bottom if you want to make this a reality! I arrive at your house on the evening. You let me in and show me to the spare bedroom. I walk in and close the door behi... read more

shemale lover September 13, 2011 100%

Dance of Lust

I'd landed it. The hottest girl in school, Adelle, was dancing with me, the quiet, slightly-feminine-bodied guy nobody knows, at the school's Christmas Dance. But everyone would know now. The last slow song had just played, and all the while I knew both of us were thinking the same thing: my plac... read more

shemale lover September 14, 2011 100%

I Knew Her Secret

I had a serious crush on the postal lady, I would wait on her until I saw that she was coming and then I would either make up some reason to go outside and exchange words with her or I would watch naked from inside of my house. I know it sounds perverted but I just couldn’t get enough of her. ... read more

shemale lover September 20, 2011 100%

My First and Last Girlfriend Part 3

I was lying completely naked on the bed, with my dick in a semi erect position, and she was next to me, playing with my hairless balls, and sliding from time to time her middle finger under them caressing all the way to my ass and then right back. I kept my eyes closed, and enjoyed every secon... read more

shemale lover September 28, 2011 100%

Connie at an Adult Bookstore Part 2

Disclaimer: The following story is not intended for minors. If you are offended by sexually explicit material or it is not legal in your place of residence, please close the document now. If not, I hope you enjoy my attempt at entertaining you with stories of my adventures. * In the previous c... read more

shemale lover September 30, 2011 100%

Working Away From Home

Im an engineer by trade and my job sometimes takes me to different parts of the country, customers want me to design a specific peice of machinery for them. I had an appointment with a firm just on the outskirts of Manchester, my company had booked me into a nice hotel for 3 nights whilst i was u... read more

shemale lover October 7, 2011 100%

A Different Kind of Woman Part 2

My hands were at one and eleven o'clock tied to the bed, the beautiful creature that I was so infatuated with turned out to be a shemale and I was at her/his mercy. Tiffany was working her/his penis up my butt with precision all the while stroking my penis keeping me rigid hard. Each time I thought ... read more

shemale lover October 11, 2011 100%

A Tranny Whores Tale

Ok, so I love tgirls. Absolutely adore them. I've had many experiences at this point, but want to share one. I looked around in the local paper and found this one TS escort. It was early morning (about 5am) and I went to see her. Even though I have had experiences, I get enthralled with nerves and e... read more

shemale lover October 19, 2011 100%