Tranny Surprise Stories

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Orientation
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Infinite Scroll

The Misadventures of Kate Pt. 03

by Catytheghost on Sep 16, 2017
Transsexuals & Crossdressers

Chapter 5: The Plot thickens! I could see Ally Cat undressing me with her eyes, and you could see she was forming plan B in her mind since Jane and Auntie were not there. "Honey, you're kind of cute-looking in the EVA suit, and I'd love to see you better." Before I could say anything, she was unbuttoning my blouse. I was wearing a white see-through one an...

Once Upon a Tranny

by Art on Sep 14, 2017
Transsexuals & Crossdressers

Once Upon a Tranny Art Kautz Copyright March, 2005 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 had expe...

Mistress Chantel, Tranny Dominatrix Ch. 01

by Sissy_Chantel on Sep 19, 2017
Transsexuals & Crossdressers

Prefix: Welcome to my next erotic story. This story will be written from the point of view of a Transvestite Dominatrix. It is a new twist in my mindset as I normally identify as submissive and as a sissy maid and slut to a dominant Master. It's my 'kink' but I have danced around in my mind a story from a position of Chantel being a true Transvestite Dominat...

Friends with Benefits

by KittyandBear on Sep 13, 2017
Transsexuals & Crossdressers

It was late Saturday evening when Dave and Eric, shuffled home to Dave's place. They were returning from a party at the campus pub and were slightly inebriated. Eric had never fit in with the popular, party-going crowd in high school, but now hoped it was different in university. Dave had a nice apartment off campus, and Eric enjoyed the freedom of hanging...

Mother, I Love a Tranny

by sexisbeautiful on Sep 16, 2017
Interracial Love

Part one. I entered my house that day, little knowing this would be one of the greatest days of my life.I heard a sound of a creaking floor and low pitched "ummmfs" coming from an upstairs bedroom. I slowly ascended the stairs in search of where the sounds were coming from. The sounds seemed to be coming from my daughters room, I smiled to myself thinking.....

Insurance Slave Ch. 03

by SEVERUSMAX on Sep 13, 2017
Transsexuals & Crossdressers

The foursome didn't require much time to consume their pizza and drinks, since they were quite famished from the group sex which had taken place during Chelsea's visit. Ned was also ready to remind his dear Roxanne that she was still his favorite lady. He intended to pound her ass, and then enjoy the others while they cleaned her out. The Brit gave him the i...

Cherry Popped

by Koth19 on Sep 11, 2017
Transsexuals & Crossdressers

I was out walking one night, a walk i used to make with my girlfriend. We had just broken up a few days ago. I don't know why I was walking here again, the memories weren't good ones. She had cheated on me with my best friend. Anyways, I was walking this familiar path through the city streets when I met a very beautiful woman. She was tall and slender with b...

Emily and Steve Ch. 09

by Travel_by_day on Sep 16, 2017
Transsexuals & Crossdressers

Over the next few weeks things really started to settle in at work. Emily was being more than accepted, she was being lauded. Emily, feeling much more comfortable as a woman, started being a much better worker. The quality of work that Emily was producing was far superior to Mike's work. She was featured on the company's intranet site as an inspiring story....

Filipina Cuckolds Her Sissy Husband

by nancyvasquez on Sep 14, 2017
Transsexuals & Crossdressers

If there's anything more sexy and exciting for a closeted sissy than dreaming about being a woman on your knees getting ready to serve a big black muscleman, it's actually having the balls to go out there and make it a reality. It happened to me! I was married, to a hot sexy girly-girl Filipina. When we got married I was still trying to be in denial about my...

My Black Transsexual Goddess

by Samuelx on Sep 16, 2017
Transsexuals & Crossdressers

Another day in the City of Ottawa, Ontario. Gosh I am bored. I walk through the corridors of the Carleton University library, yawning and stretching at the prospect of an all-nighter because my take-home midterm is due in the morning. As I make my way to my usual spot on the second floor, a wide-eyed white chick sitting in the back glances at me, as does a t...