Transsexual Stories

1,767 results
Orientation
Length
Source
Infinite Scroll

My Babysitter Ch. 02

by GreenGale on Sep 11, 2017
Transsexuals & Crossdressers

There it was again. That hard, warm cock in my mouth. I loved it. I needed it. I knew it wouldn't last, though. I awoke from my dream with my hands on my dick as usual, but my mom was standing by my bed. I was so surprised to see her standing over the bed I almost forgot to conceal my erection. "Hey son we're home from our trip to Hawaii!" she beamed. "Oh...

Dealing with It

by Alemuchomas on Sep 16, 2017
Transsexuals & Crossdressers

This is a real story that happened to me. I know that some of you would have taken different decisions but this is what I decided to do. Excuse the poor writing since I don't have too much experience in this. ***** I was alone once at my dads house, mom and dad were split up and I remember that one of the times that I was staying with my dad, he had a frie...

A Love Like Ours

by Samuelx on Sep 16, 2017
Transsexuals & Crossdressers

Katrina Wilson is my name. Like the storm, but deadlier. I am feeling so bored these days. I needed to find something to do. I get really horny on days when I've got nothing to do. Anyone looking at me would see a tall, good-looking black woman in her early twenties. I'm not. I'm actually a transsexual. I have a beautiful woman's face, body and a fantastic b...

Mistress Raven Black

by Samuelx on Oct 29, 2018
BDSM

"You're either dominant or you're not," Raven Black stated, speaking to the camera. On her blog, which was followed by tens of thousands around the world, the young Black woman spoke about her experiences as a professional dominatrix, the state of the affairs between Black men and Black women, and her private life. The videos that Raven Black made were quite...

Danielle's First Time

by FellatiaViper on Sep 15, 2017
Transsexuals & Crossdressers

Danielle was born in the winter to 1976, but she was born a male by the name of Daniel. Daniel looked like a normal male child aside from liking girly things. Whenever Daniel would play dress-up he'd always dress in his mother's or his aunt's clothes and his parents thought that was cute until Daniel got a bit older then his father sternly told him, "boys do...

Transsexual Journey 01

by walterio on Sep 19, 2017
Transsexuals & Crossdressers

PRELUDE Jay woke up to the gentle movement of the cruise ship through the Atlantic. His bladder needed relief so he eased out of bed and quietly used the bathroom in the stateroom. Once he had taken his morning piss, he washed his hands and cock before crawling back in bed. As he approached the bed he admired the Spanish beauty lying there with her back to...

Mistress Donna of Jamaica

by Samuelx on Sep 16, 2017
Transsexuals & Crossdressers

"Ma'am, has anyone ever told you that you look just like Serena Williams, you know, the tennis star?" says the chubby, bespectacled young white woman working at the makeup counter at Sephora, and I take a deep breath, and bite back the sharp reply that's just on the tip of my tongue. Instead, I nod and smile, trying to be as friendly as I can. One of my new...

Alpha Gamma's Secret Ch. 2

by Wannabe Chick on Sep 11, 2017
Transsexuals & Crossdressers

-4- Molly awoke to the annoying sound of her alarm beeping. Groggily, she reached over to her night table and turned it off. It was 7:00 AM, way too early for a 19-year-old college girl to be awake, in her opinion. As she stirred, her girlfriend wiggled up against her, eager for body heat. Molly smiled and looked over at Gina – her girlfriend, lesbian lover...

Crystal, Meth and Me

by MrStaggerLee on Sep 11, 2017
Transsexuals & Crossdressers

Author's note to the reader: The objective writing this story was to capture a really seedy and sordid encounter involving a few men and a transsexual prostitute. The story is sexual in theme and could be considered erotic by some, but it's also pretty dark and bleak. You have been warned... I wasn't sure I remembered the last time I had seen Crystal stra...

My Journey to Heaven

by Corina84 on Sep 14, 2017
Transsexuals & Crossdressers

How did I end up here? I couldn't believe what just happened! I was in a daze from what I just did. I was neither sickened or disgusted by it, I was just surprised that I had come so far. Here I was, on my knees with cum drizzling down my face. Something that I have fantasized about for years, but was never able to gather enough bravery to step out and try...