Shemale Gloryhole Stories

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Hearts Academy Ch. 04

by RoseB on Mar 16, 2020
Transgender & Crossdressers

Disclaimer and Notes: Disclaimer and Notes: Hearts Academy is an dark horror/mystery story focusing on the reluctant feminization of a young artist. There are many themes such that cause it to be disturbing for those who cannot handle terror or dread well. This is a sequel to The Rose Diaries. While the characters are brand new, it does reference events an...

The Robertson's Sissy Ch. 14

by Clite69 on Apr 28, 2020
Transgender & Crossdressers

My apologies on my disappearance, life has been crazy. Though this chapter might not have been worth the wait I am sure the following chapters it sets up will. *** Lela and I had spent most of the night cuddled up on the couch. I was woken around 4am by Lela who wanted to go up to the bedroom. In a half sleeping state I followed her upstairs and collapsed...

My Journey Ch. 05

by npanxx on Sep 25, 2017
Transsexuals & Crossdressers

This is the fifth installment of My Journey. Although not necessary, this story will be more appreciated if you read Chapters 1 thru 4 first. Thank you to all who read my first four submissions and provided feedback. I hope you enjoy reading the story as much as I enjoyed writing it. (And I REALLY enjoyed writing this one!) Please, please leave comments a...

Meeting Raquel Ch. 03

by Floydman1 on Sep 15, 2017
Transsexuals & Crossdressers

After that, I didn't have much in the way of discipline problems with her. Raquel still got off in a big way on being punished, so I would incorporate it somewhat when we were having sex, but mostly I fucked her after she was tightly bound. Out of nowhere, one day she asked me, "Have you ever thought about bringing somebody else in to play with us? Like a re...

Sara's Silken Ladder Ch. 04

by Calandria2 on Sep 16, 2017
BDSM

Only if you've read the first three parts will this make sense. Everyone in this story is over eighteen. * I glanced at my companion as we were both eating a rather limp sandwich on our flight to Alicante, and wondered at just how little I knew about Kirsty, the girl I'd just agreed to share my life with. Achingly beautiful, she certainly was, and when she...

Mia Mine Ch. 10

by cliptoe on Sep 26, 2017
Transsexuals & Crossdressers

Mindy stared at the droplets of rain as they ran down the window of the little coffee house with free Wi-Fi. She was waiting for the special website to load so she could change the phone number in her ad to the new 'burner' she picked up. She needed one more "liaison" (she hated the word trick, it made her feel cheap), to make enough to get a room for the ni...

Dark Angel Ch. 07

by LevanaHyll on Sep 12, 2017
Sci-Fi & Fantasy

Sorry it took me so long to post this chapter, but life as usual had me away. Hope you like it,and please don't forget to give me your opinion which I apreciate more than the actual votes. ;) ***************** Chapter Seven Anniel startled awake and tried to sit up, but she was wrapped in a heavy blanket—a blanket made of black feathers. She frowned and g...

The Lost Boy Ch. 04

by DamienDeath20 on Sep 25, 2017
Transsexuals & Crossdressers

A.N. Hello errybody! This chapter was kind of a special treat where the commissioner gave me free reign for the scene so it's near and dear to me :3 The Following Contains: Sexy/Kinky Librarian dickgirl fucking a bottom femboi senseless because that's hot x3. If you're not a fan of such things, avert your delicate eyes! Other than that I hope you all enj...

Show & Tell Ch. 28

by murphtsurf on Oct 31, 2017
Erotic Couplings

This is a long chapter, really two, that needed to be told at the same time so the reader could follow how it all actually happened. I hope you have/take the time to read it all at once... and enjoy how erotic it all turned out. Thank you ***** Show & Tell Chapter 28 After our weekend in New York, and the time it took both of us to recuperate, I...

A Caged Bird Sings

by YKN4949 on Sep 18, 2017
Transsexuals & Crossdressers

Part 1: Entering the Criminal Justice System The gavel came down hard; the cracking sound was so loud that it made me jump. But I was in a sort of haze, I didn't really understand what was going on. I looked over at my public defender, his lips were pursed and he was quietly collecting his papers on his desk. "What does that mean?" I asked and he looked ov...