Sissy Hotel Stories

62,092 results
Orientation
Length
Source
Infinite Scroll

Uurf Ch. 02

by Beatnic_jazzman on Sep 16, 2017
Sci-Fi & Fantasy

Sissy returned with great fuss, from the moment the carriage was heard there were calls for servants to carry the purchases in. Three armfuls were brought, passing me in the hall, before Sissy appeared arm in arm with Macteth. Her dress showed more of her than any but I had seen, she had a tight frilly top that ended just below her breasts throwing them up...

It Happened in Mexico Ch. 02

by Angelscuck on Sep 16, 2017
BDSM

Kelly was frantic with worry when he had not heard from Angel the first few days. He had called everyone they knew, family, friends, hospitals, and police. Then he received Joaquin's call. "No police, no anyone," Joaquin had warned, "$20,000 in one hundred dollar unmarked bills by Friday, or Angel's dead!" Kelly maxed out his credit cards and got the mo...

Seductress & Daemon: Sissy Pt. 01

by SeducedKnight on Sep 15, 2017
BDSM

After Eating out my Seductress for the last hour, we hear a knock at the hotel room door. "Go open it." I go to the door dressed only in my rubber wrist and ankle bands with heels and a pink crotchless panty, I have a plug in my ass and a cold metal cage on my cock. I open the door wide in my full nakedness to reveal a prettily dressed sissy outside. "...

Jasmin wears the pants

by Gretatv on Sep 13, 2017
Transsexuals & Crossdressers

This story is fictional. You know the drill: If you are under aged or don't like TG stories don't bother reading any further. All rights are reserved. If somebody wants to publish this story somewhere else please contact me first. My thanks for editing this story go to alwaysupforyou2004! Jasmin wears the pants By Greta I had just arrived in New York for...

Samantha Meets a Dom Master

by SamanthaSatine on Sep 16, 2017
Transsexuals & Crossdressers

A true story - I am the main character and all the various activities described were undertaken with my consent...no harm came to me in any way... ***** The date was fixed. The room was booked – neither of the willing parties could accommodate, a not unusual event in the world these two inhabited from time to time. The morning of their meet had now arriv...

Black Cock Smoking Sissy Slut

by Lisa_Fuckslut on Sep 14, 2017
Transsexuals & Crossdressers

I left the club early. No luck tonight in getting my ass laid. Where were all those hot young studs with their big swinging penises and cum-filled balls when you need them? I had dressed in my sluttiest gear. 6 inch 'fuck me' heels, fishnet stockings and a tight little leather dress. Heavy makeup. Long, thick false lashes to flutter at the boys. Long, sexy,...

Man Disciplines Sissy Ch. 06

by LanaBehave on Sep 14, 2020
Transgender & Crossdressers

This is a fantasy. Scenes in reality should be built on consent, safety, and communication. No character in this story is less than 21 years of age. * Back in my own room, I threw myself on the sofa again, face down, and for a half a minute I just lay there, breathing a little fast, excited, ashamed, squirming a little in spite of myself, thinking of what...

Mistress Chronicles Ch. 01

by MistressMtoyou on Sep 25, 2017
Fetish

Subject and background. This is a recap of my first in-person session with a submissive. The subject passed the various pre-session requirements described in my second story "A few good subs" and after an extensive interview and evaluation process I offered him the opportunity to do an in-person session. I'll admit upfront that I was a novice at this point...

A Jamaican Vacation Ch. 04

by sissyashley4bbc on Dec 24, 2019
Transgender & Crossdressers

Rebecca studied me up and down. "What happened to you?" She asked. "I...uh...I..." Ty cut me off, "you look like you are in shock Rebecca. Let's fix you a drink and I'll explain everything to you." "Make it a double," she said as Ty started to make her a screwdriver. He handed her the drink, grabbed a joint, and ushered us outside. Rebecca sat down...

My Wife Takes Me Much Farther

by Godscountry on Sep 26, 2017
Transsexuals & Crossdressers

It's been three weeks since my wife turned me out at her book club and turned me into a cumslut. That event seems to have really opened up my wife's imagination and made her hunger for more dominance over me. For the last three weeks, she's kept me locked in chastity, even though our deal was that I would be released after the event. She's also made me kee...