Sissy Hotel Stories

62,092 results
Orientation
Length
Source
Infinite Scroll
SmutMD: The World's Biggest Erotic Literature Search Engine.
© 2024 SmutMD.com

From Her Ex-Boss to her Bitch Pt. 07

by His_fag_wife on Sep 25, 2017
Transsexuals & Crossdressers

Please do not read this story if fantasy is not your thing. This has scenes of outrageous levels of forced sissification, forced bi and gay scenes, watersports and general humiliation and degradation. It's just pure fantasy and includes some hypnosis. Some readers find these stories too full of fantasy, in which case please just don't read it. It had all st...

Man Disciplines Sissy Ch. 03

by LanaBehave on Aug 20, 2018
Transsexuals & Crossdressers

I watched Daddy walk to the door of the hotel suite, and I watched him open the door, and then I watched him step into the hallway. He was gone. The door closed behind him. I stood there, in my dress. In my heels and wig. I felt a shiver run through me, and I thought about Daddy, and what had just happened. I went to long mirror on the bedroom door, and I...

My Medical Vacation

by sissymissyct on Jul 10, 2019
First Time

BRENDA'S MEDICAL VACATION by Brenda Finally on the way to the airport. My first trip to Europe. I wish my wife was coming with me but she was just dropping me at the Laguardia international terminal. I certainly hoped we would get to go to Europe together and do the normal sightseeing and partying that most couples enjoy, but this was a special trip for me....

From Her Ex-Boss to her Bitch Pt. 06

by His_fag_wife on Sep 25, 2017
Transsexuals & Crossdressers

Please do not read this story if fantasy is not your thing. This has scenes of outrageous levels of forced sissification, forced bi and gay scenes, watersports and general humiliation and degradation. It's just pure fantasy and includes some hypnosis. Some readers find these stories too full of fantasy, in which case please just don't read it. ***** It had...

AliExpress and Sissy Downfall Pt. 06

by His_fag_wife on Mar 6, 2018
Transsexuals & Crossdressers

"Ok, now you've been fed, back in the chair and Candice will get your make up done, so that you are as pretty as you can be when you return to your Mistress and Master." "Get all that mess cleaned off her face please Candice and start making her up to look pretty." "Yes Miss Bell." Charlie got back in the chair and Candice prepared to make her look as pre...

Robin and Jimmy Olsen - Sissies Ch. 04

by tawnysuede on Sep 15, 2017
Celebrities & Fan Fiction

The Date Continues (finally) ***** Just as Ollie and John began to wonder what was keeping their dates, they spotted the delectable pair of sissies returning from the rest room. When they reached the table, both men stood. Their politeness was rewarded by a brief kisses from the pretty lads. Each girlyboy also managed to run her hands across the crotch of...

Another Submissive Slut Ch. 08

by Stillherer on Sep 19, 2017
Transsexuals & Crossdressers

I had hurried home from the porn shop only to run into Derrick in the lobby of the building. Lucky for me his mother emerged from a hallway and he could only cast me evil looks. His mother however took the opportunity to lay into me about my behavior and image. I realized as I slunk away from the verbal abuse that the chain around my waist was probably visib...

The Trap Ch. 04: Paula's Debasement

by Paulateevee on Apr 13, 2020
Transgender & Crossdressers

Due to the current situation with COVID-19, I've been able to get this part out a lot quicker than I would have normally. In this part Paula's life changes forever. The usual disclaimer applied. Everyone is (well!) above the age of consent. This story is about crossdressing. If that's not what you like how did you get to this page. I hope you enjoy. Paul...

Suggestions from Her Kinky Sister

by timeagain93 on Sep 16, 2017
BDSM

Mistress Patty had a kinky sister. She had been dominating her husband for years and according to my Mistress the man was her complete slave. Naturally they gossiped and soon I received a text listing questions regarding limits, safe words and playtime. The safe word was her hometown. At any time I could say it and break out of the scene. Playtime was desi...

Mike the Gang Bang Bitch

by sissyneko on Mar 17, 2020
Transgender & Crossdressers

Standing in the bathroom wearing just his little pink bikini panties and stockings, Mikes gaze was transfixed. Not on the panties, the usual draw of his lust, or even his white thigh high stockings with their little pink bows at the top. None of that drew his attention, it was the bathroom itself, it was run down, dingy and in the worse part of town. But non...