Shemale Suprise Stories

1,639 results
Orientation
Length
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Infinite Scroll

The Greatest Liar Ch. 01: My Awkward Phase

by alexandrarios on Jul 3, 2019
Transgender & Crossdressers

Chapter 1 My Awkward Phase The greatest lie is that what happens in high school doesn't matter, because life begins in college. I pretended to agree, although I never believed it, for I was the world's greatest liar. Wannabees I was hanging out with my friends Quinn, Barb and Anne in the Newspaper Office, our refuge at University High in Los Angeles. A g...

It's Only Temporary Pt. 02

by ChangeYourPassword on Dec 24, 2019
Transgender & Crossdressers

Continued from Part 1 -- Read that first! Author's Note: This is a work of fiction. It is a story of sexual fantasies and fetishes. These sexual practices are not for everyone, but those of us who delve into them understand the allure. The characters in the story certainly do. If you enjoy this story and the fetishes involved, great. If not, please forget t...

Would You

by sydian on Sep 16, 2017
Transsexuals & Crossdressers

'Would you...?' 'Look the part to play the part....' 1 5' 4...dreaded, and to be dreaded....bookish, be-spectacled—damn near owlish....so much so that you might miss the way her tits spoke to you no matter how much she attempted to 'silence' them ....that you might miss the way her skirt gathered at the flatness of her tum, then fell away from her no-wais...

Kim Lazenby's Resumé Ch. 02

by PrimalRoots on Sep 13, 2017
Group Sex

I like to think of myself as a master of exploitation. Others will call me a bitch, a whore, or just plain evil. But my interference in the affairs of others is minimal; its victims further extend the problems I cause. Many solutions present themselves, but are neither explored nor realized. I feel no sympathy, and remain far from empathy. I only feel joy fo...

Resolution

by PattyMarie on Sep 16, 2017
Transsexuals & Crossdressers

This is the third part of a trilogy by three different authors. If you haven't read Torn by patricia51 and A Typical Day by Chagrined this won't mean much to you. They are both worth the read. Consider these two stories as the prolog. * While we attend church regularly, I'll admit to not being a praying man, but I prayed laying in bed that night. "God, he...

Ali's Art Ch. 03

by harding on Sep 14, 2017
Novels and Novellas

------------------------------------------------- This episode involves Tom only. No Ali. But it does include the loss of his virgin state. For those of you who are waiting for Tom and Ali's relationship to develop, Chapter 4 will bring them back together. For now, enjoy this episode in its own right. And if you can't wait, Chapter 4 will be available almos...

Teen Stud and the School Therapist

by dominanceaddict1 on Mar 3, 2020
Transgender & Crossdressers

I was about to leave work early when my phone rang. It was one of the school administrators. They also served as my secretaries. "Mr. Caldwell? A student is here to see you." No, I hadn't seen this student before. The student hadn't wanted to describe his issue with the admin and instead wanted to speak to me directly. My name was Sam Caldwell and I worked...

The Golden Orb Ch. 02

by hawke56 on Jan 9, 2018
Transsexuals & Crossdressers

Synopsis: This story is a direct continuation of my story "The golden orb." It is advised that you read the first installment beforehand to understand what little plot is happening. If you are just looking to read some story with a lot of sex scenes though you might enjoy this even without reading the first part I guess. The story further follows Sam and Ja...

Afro Stress Relief Ch. 06

by llts1970 on Dec 12, 2018
Transgender & Crossdressers

I was running a bit late after I'd overslept my alarm clock, my shift at Missy Bee's and the hard riding I got from Leroy must have tired me out more than I thought. I managed to get into work just on time, once there I rang Sarah. "Oh hi Johnny, sorry I mean Tina, wow it's early," Sarah lazily answered. "Hi Sarah, is Marci OK? I can pick her up this eveni...

A Learning Experience Ch. 09

by Joscelyn2tg on Sep 19, 2017
Transsexuals & Crossdressers

--- This chapter is dedicated to those of our Brothers and Sisters who have left us far too soon. Thank you for waiting so interminably long between chapters. I am afraid I allowed my enthusiasm for editing wonderful new stories by other authors get a bit out of hand. But I have taken some time off to finish my little transition Biography. I would like to...