Shemales Stories

429 results
Orientation
Length
Source
Infinite Scroll

My Magical Experience Ch. 03

by ModuRaziel on Sep 13, 2017
Transsexuals & Crossdressers

Before me stood two gorgeous women with enormous, dripping cocks. It seems to me Arianna had grown bustier and sexier as a result of my Queen's gift, but perhaps it was just a shift of perspective on my part now that she was sporting her own love tool. Either way, I couldn't contain myself. I hoped my Mistress wouldn't anger at my initiative, but I scrambl...

Father-In-Law Shemale Adventure

by greyhound_guy30 on Sep 16, 2017
Transsexuals & Crossdressers

My wife's parents were visiting LA from back east. We live in a small one-bedroom apartment in the valley. She wanted them to stay with us but we didn't have room. They got a room in West Hollywood. My wife and her mom had gone shopping for the day. I was supposed to be at work but at the last moment I decided to take the day off. Since the girls were out, I...

My Stepmother's Surprise

by sissybr on Sep 12, 2017
Transsexuals & Crossdressers

This is my first story, so I would appreciate some tips and comments. Please enjoy ^^ * My name is Robert, I'm 18, skinny and not too tall. I've never had much luck with girls, in fact I never dated one and I used to spent my days playing games on my computer and watching porn. Shemale porn. Dominant shemales fucking men. I wish i could be one of those men...

Hijab Girls and Shemales

by Samuelx on Sep 16, 2017
Transsexuals & Crossdressers

Call me Sammy, please. I kind of prefer it to my full name, Samirah Taariq. I'm a young woman living in the City of Ottawa, Province of Ontario. The daughter of a Lebanese father and Somali mother. I was raised in the City of Baalbek in Southern tier of the Republic of Lebanon, and have lived in Canada for the past ten years. I'm nineteen years old. My mothe...

I should have Kept My Mouth Shut

by submissiveanne on Jan 28, 2019
Transgender & Crossdressers

This is a story that takes place years after the events of "Ramona Changed Me". *** Sometimes I have a big mouth and don't know when to not say something. This got me into trouble. I was 26, this was like 2005 and working at a job where I was assisting in the repair of plumbing damages. A vendor or someone goes into work on a home, they damage the sprinkl...

Carla Ch. 03

by fantasydreams on Sep 26, 2017
Transsexuals & Crossdressers

So, I reflected, I had quite a day ahead of me. Initially excitement coursed through me as I contemplated the evening to come, and the scope to explore the new extensions to my sexuality. I vividly recalled some moments of the time I had already spent with Carla, particularly it seemed, when I felt truly submissive to her, and they felt so exciting to reflec...

Small Cock Frustration

by jamtby on Oct 8, 2019
Transgender & Crossdressers

In 2007 I suffered from a severe medical condition which required extensive surgery. The procedure saved my life but the removal of my prostate, bladder, and extensive nerve damage left me without a functioning sex ability. My cock and balls remained outwardly normal but they were not doing what they were supposed to do. The relationship with my wife became...

Showing Off For My Wife's Pleasure

by HotJennieh on Sep 19, 2017
Fetish

A first time effort based on real events. * There I was lying on my back, on the floor of a cheap adult bookstore. All I was wearing were 5" heels, black thighhighs, and a nipple chain. In one hand, I was jerking my throbbing shaved shaft while I was using my other hand to fuck my ass with a double headed dong. Cum was glistening on my face and chest and r...

A Tale of Slavery

by gunnarsub on Sep 17, 2017
BDSM

Once upon a time there was a straight guy who was known by everybody as a well respected fellow. But he had a secret life. Nobody knew that he dreamt to become a feminized slaveslut, seeking an infinite and irrevocable blackmail relationship with a pitiless Mistress who would be prepared to break him with no way out. He wanted the Mistress to torment him n...

The Sexiest Shemales Ch. 03

by cleanly_shaven on Sep 13, 2017
Transsexuals & Crossdressers

I woke up laying on Daisy's inner thigh. Her cock was lying right in front of my face. It smelled so good. It smelled like sweet perfume and cum from our previous romp. I smelled it and began rubbing the tip of my nose on it and then slowly I began kissing it. Daisy began to slowly wake up and did her cock. It grew more and more as I continued to kiss it and...