Trans Surprise Stories

136,543 results
Orientation
Length
Source
Infinite Scroll

Kathy and Surprises Ch. 01

by LorenzoAbajos on Sep 19, 2017
Transsexuals & Crossdressers

Graduating from high school at eighteen I was off to college that fall. I was going to a community college in the nearby city in preparation for going to a more prestigious institution. My name is Greg. My grades had not been that great. I was more interested in girls than school and had made the attempt to work my way through all of the girls in high scho...

Tranny Night Out and One Kinky Session

by BmthAdmirer on Sep 16, 2017
Transsexuals & Crossdressers

Guess I should start by explaining myself, as a young guy I always knew I was not the same as a lot of my friends and enemies for that matter, girls had no interest in me at all apart from ones who were long term friends. I knew something was wrong but never worked out what it was till one evening whilst dating a girl named Becky I had met on an online dati...

The Porn Theater

by pondcat on Oct 15, 2017
Exhibitionist & Voyeur

I was traveling to a new city for work and looking at the sex listings to find if there was any decent gloryhole action. It's getting harder to find a good ABS anymore. But not in this town. This town was full of options. The most curious option of all was what was described as a genuine old-school porno theater. A floor full of seats, sofas, even a few bed...

My Trans Girlfriend and My Sister

by ArkansASS on Oct 6, 2020
Transgender & Crossdressers

Warning: This story involves sex with a trans woman and my sister. If either transgender stories or incest are not to your liking; unfortunately, this story will not be for you. I have given my trans girlfriend in the story feminine pronouns (eg. "She" and "her") For the sake of creative convenience. I started dating Michelle about 3 months ago. She is my t...

Spicy Story

by TexanBelgianCutie on Jul 17, 2019
Transsexual

Family Kyle had wildly mixed feelings when he saw his mom walking towards him. He kept his feelings to himself however and forced a big smile to welcome her back from the SpringWood Adult Mental Hospice. He had not seen her since he was child, yet he was glad to see she looked healthy and happy. “Hey Sara”, he grimaced, “How are you? Sara had spent the last...

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Modified Escort Service: Nancy

by Crimson_Spectre on Jul 27, 2020
Sci-Fi & Fantasy

Author's Note: it has been a long time since I wrote the original Modified Escort Service. Sorry I kept y'all hanging but I wanted to make sure I treated sex workers with respect and had to do a lot of reflection on how to get it right. I want this to be an anthology with a lot of diversity and respect for the escorts. Any feedback is appreciated. *******...

How Julia Stiles Changed My Life

by Moonraker_Bond007 on Sep 17, 2017
Celebrities & Fan Fiction

I often envied my cousin Jason. He lived in Los Angeles, and on more than one occasion when I had gone to visit him, I had seen the people known to the rest of America as "celebrities." Sure, living in Las Vegas has its perks. After all, Las Vegas is the craziest city in the world. Nonetheless, there are times when Jason seemed to have it all. My name is M...

In Praise of Haitian Women Ch. 04

by Samuelx on Aug 27, 2019
Transgender & Crossdressers

Meet Giselle Lucien, a French Canadian Transgender woman living in the City of Ottawa, Ontario. Giselle is fairly active in LGBT circles and believes in fighting for justice and diversity. Born in the environs of Amos, Quebec, and raised in the Capital region of Canada, Giselle studied Women's and Gender Studies at the University of Ottawa, prior to working...

The Theater

by WhiskeyIsGood on May 11, 2020
Transgender & Crossdressers

This is based off my actual first encounter with a transsexual, and also my first trip to an adult theater back in March, just before the lockdown started. It certainly didn't go the way that I expected, but I still had a good time that day. I figured I would share my experience with my fans, although this is a slightly exaggerated version of what actually h...

Blue Moon

by ash_rigby on Oct 12, 2020
NonHuman

Note: The human in this story is explicitly an AMAB (assigned male at birth) nonbinary individual who uses they/them pronouns. Words for male genitals are used for them, but they are not a man and any suggestion of that in the comments is not welcome. This piece is not intended to fetishize trans/nonbinary people (I'm a nonbinary trans person), so any commen...