Tranny Surprise Stories

136,341 results
Orientation
Length
Source
Infinite Scroll

A Queen

by Eterriswolf on Jun 11, 2019
Transgender & Crossdressers

A/N: This is a fictional story. No characters in this story are under the age of 18 and they are not real people. Any similarities between the characters and real people are pure coincidence. In addition, this story involves activity between gender nonconforming individuals, one of which is a Trans Lesbian. If this is not something you are comfortable with...

Somali Man Discovers Shemales!

by Samuelx on Sep 16, 2017
Transsexuals & Crossdressers

As Salam Alaikum, people. My name is Ibrahim, and I'm a Somali brother living in the City of Montreal, Quebec. I have something to share with you, ladies and gentlemen. I was raised in my ancestral hometown of Mogadishu, Somalia, and have been living in Montreal for the past ten years. I love Montreal, the best place in la belle province, even though I shall...

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...

K is for Karla

by BethanyJ on Sep 16, 2017
Transsexuals & Crossdressers

*** Transgender-themed stories which I hope will be of interest to those who like women, or would like to be a woman. Which includes me! *** As I rounded almost the final corner heading home I was feeling pleased with myself. Just about my most successful outing ever. It had gone so well, the driving, parking in the shop car park, walking up towards the en...

Dream Bride Tranny Ch. 02

by yano on Sep 13, 2017
Transsexuals & Crossdressers

Orchestrated by the Kinky Brides Group (KBG) Uncle Yano has been forced to have sex with his young niece, fully dressed in her bridal gown, in the bridal suite and on her wedding day. The evening continues and amid the celebrations find out what the frilly panty wearing Yano and Kirsten do next. As the night went on and the dancing continued I had another...

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...

Dream Bride Tranny Ch. 03

by yano on Sep 13, 2017
Transsexuals & Crossdressers

I was never allowed to forget that I had had sex with my 18 year old niece when she modelled a few bridal gowns for the KBG. Even her wedding day was hijacked and, in the final part of a wedding day shock for bride Kirsten, she has dressed her Uncle in her most amazing bridal gown and is about to embark on another kinky adventure. Hand in hand Kirsten and I...

A New Adventure... Ch. 02

by johnjinglez1 on Jun 6, 2018
Transsexuals & Crossdressers

This is a continuation of my "Sex Diary." For the better part of a year and a half I decided to try some new things in the world of CD / TS / Sissy boys. All stories are 100% real. *** After my first three encounters with TS and CD's left me feeling unfulfilled I gave it up for a few months and figured it just wasn't for me; I went back to having sex with...

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...