Tranny Stories

1,390 results
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Infinite Scroll

The Anniversary Present

by DrLuverotica on Sep 15, 2017
Transsexuals & Crossdressers

My wife, Jo, is a very hot, very sexy 40 year old doctor. For the past few years I've found it really difficult to please her sexually. That all changed when I bought her a Rampant Rabbit vibrator from Ann Summers for our tenth wedding anniversary. When Jo unwrapped the box containing the 8 inch silicon black vibrator she was giddy with excitement. I was de...

After Church

by alien_freak_nugget on Jan 15, 2019
Transgender & Crossdressers

I was just horny. All of the time. I just wanted to fuck someone in the worst way. 18 years old, never had a date. Too skinny, too weird. I wore my hair long, not a very hairy body, not very athletic. Just a skinny kid who didn't get any attention. Lot of church girls in the bible belt but they weren't very interested in me. I guess. It didn't seem like anyo...

Black Women Love Transsexuals

by Samuelx on Sep 16, 2017
Transsexuals & Crossdressers

Hello, there, dear Literotica reader. What's up? Raquel Dawson here. I'm a tall, curvy and sinfully sexy sister from the islands of the Caribbean and the most sexually adventurous Black woman on this planet today. I do believe we've met before, but just in case you got a short memory, let me give you the rundown. I'm a young Jamaican woman living in the City...

The Club

by SweeetLee on Sep 13, 2017
Transsexuals & Crossdressers

They entered the club and were greeted warmly by a long-time acquaintance. She was a dark haired beauty, and the one who had first told them about this place and used her membership to get them in. It wasn't that it was exclusive. It was off-limits to outsiders. You had to know someone just to learn the address. She ushered them through the very legitimate...

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...

Tranny Tales Ch. 10

by erectus123 on Dec 12, 2017
Transsexuals & Crossdressers

The use of the word Tranny is not meant to be disrespectful, it is used as it was in the past although not politically correct at this time. TRANNY STORIES CH: 10 GILDA — 2010, AN AFTERNOON Her name was Gilda. She wore one of those large green felt sun hats, the kind that are so large you could hide your face under it. If her face was hidden, her breasts c...

Tranny G's all Tranny Gang Bang

by Creamyirish on Sep 13, 2017
Transsexuals & Crossdressers

Chris had finally returned after a year overseas. During his leave he flew out to Phoenix and we would spend a few days in Las Vegas. We drove four hours and checked into the hotel. A year apart and we ripped our clothes off and fucked hard. We took a short nap and went for an early dinner. I told Chris I was taking Tranny G out for the evening, a surprise t...

The Ballad of Barry

by AngelaK on Sep 16, 2017
Transsexuals & Crossdressers

Part 1 - The young man Barry was in his early fifties. He stood about 6ft-1, and weighed nearly 300 pounds. He had brown hair going to gray, and green eyes. In his youth, he'd been considered handsome. Barry was also very lonely. He was struggling to cope after the loss of his wife nearly five years ago. His wife of 25 years was a companion he sorely misse...

A College Sissy Ch. 03

by nat_rose on Sep 26, 2017
Transsexuals & Crossdressers

There was the time I was playing hide and seek at my friend's house. I was hiding. I ran upstairs, looking for some place to sneak into so I wouldn't be found. I felt my time slipping, but before it was too late, my friend's sister caught onto the game we were playing and waved me into her room. Her name was Stephanie. I was a shy kid, and my face turned r...

There's Something about Sarah Ch. 07

by MicheleNylons on Sep 25, 2017
Transsexuals & Crossdressers

Chapter Seven -- A Conclusion of Sorts Tina flatly refused to attend the reading of Amanda's will and to be honest I didn't blame her. "Sarah; it's between you and Sloane and it's legal shit. I don't think having a former prostitute and current transgendered porn star is in any way going to serve you well. Besides; you need to stand on your own two feet. I...