Shemale Stories

1,331 results
Orientation
Length
Source
Infinite Scroll

A Learning Experience Ch. 10

by Joscelyn2tg on Sep 19, 2017
Transsexuals & Crossdressers

--- Changes. Less than a year of time has flown by... and yet it seemed to stream back a millennium. How exactly do you describe such changes as those I had experienced? The answer of course, is you can't... to my gentle readers, who have been pulled along by my words, thank you for sharing what I learned, what I felt... what I lived. But I had changed... an...

Trying It On For Size Ch. 01

by kelmag on Sep 25, 2017
Transsexuals & Crossdressers

I was twenty minutes early for my one o'clock appointment so I found a shady spot in the parking lot of the upscale chain motel, kept the engine running to power the air-conditioner on the warm Sunday afternoon, took a few deep breaths and tried to relax. My mind wondered back over the series of events that brought me here. The "here" I speak of was at the v...

Never Going Back Again

by Cyanlot on Sep 12, 2017
Transsexuals & Crossdressers

To tell the truth, I never really figured out how to do the guy thing very well. I was always small for my age. People used to say that I'd shoot up someday, but it never happened. All through my school years, I looked about two years younger than my classmates. It didn't make for an adolescence filled with confidence, or even security. I was picked on merci...

New Gurl in Town Pt. 02

by GavinIsaNuisance on Oct 5, 2020
Transgender & Crossdressers

This story and its contents is entirely fictitious. Any similarities to persons or things living or dead is purely coincidental and entirely unintentional. All persons depicted in a naked/sexual manner are 18 and up. Andy begins his sissy adventures as Bianca, but will he be able to woo his crush Riley, or will he be forced to be Carol's bitch forever? We...

My Journey Ch. 03

by npanxx on Sep 25, 2017
Transsexuals & Crossdressers

This is the third installment of My Journey. Although not necessary, this story will be more appreciated if you read Chapters 1 and 2 first. Thank you to all who read my first two submissions and provided feedback. I have some ideas for a fourth chapter, and could take the story in a number of directions. Let me know where you might like to see the story go...

Money Shot

by GavinIsaNuisance on Jul 6, 2020
Transgender & Crossdressers

All persons depicted in nude/sexual situations are 18 and up. This work is entirely fictitious. Any relationship to persons living or dead is unintentional and entirely coincidental. Shy nerdy virgin Danny is gets a project of a lifetime: photographing his shemale classmate in the nude which leads to new sexual experiences and a new lease on his formerly se...

Blackmail

by Jay626 on Dec 2, 2019
Transgender & Crossdressers

**I did this for a fan who asked me to write a TG story. This is not my typical story, but I enjoyed writing it.** Caleb Thompson walked into the cafeteria thinking about the next class and the ninety minutes of boredom that lay ahead. Math was his weakest subject and college level math was a chore for him. He just knew that a B in the class was all he need...

Shemale Finds Her Man At The Party

by SugarandSalt on Sep 25, 2017
Transsexuals & Crossdressers

It was finally done. Rebecca's big paper. Just in time too. The Halloween party she planned to attend tonight would reach full force in an hour or two. The sun was already setting. Rebecca stuffed the pages in an envelope and licked across it. Her tongue flicked around her mouth afterward to shoo away the bad taste that the envelope had left. Rebecca was v...

Gangbang: Train Full of Dicks

by Fire22 on Sep 25, 2017
Transsexuals & Crossdressers

I stared at my exposed tit, and felt a rush of nerves get me. As I contemplated making a run for the exit, the guys around me circled around what little space we had in the train. I grabbed the broken piece of my red dress and pulled it back up trying to cover up my right tit, but the guy sitting next to me was keeping me by playing with my nipple. "Um......

My Life Pt. 02

by ShyTammy on Sep 26, 2017
Transsexuals & Crossdressers

So this is part two of my life story. All the stuff from Part 1 still applies. As before all characters engaging in sexual acts are over the age of 18. This story is chronologically linked to Part 1, which won't necessarily be the case with other stories in this series. ***** Decisions, Decisions It had been two days since my encounter with Mr. Moran in d...