Sissy Hotel Stories

62,092 results
Orientation
Length
Source
Infinite Scroll

Moon Probed at Hen Party

by Cumfusion on Sep 13, 2017
Transsexuals & Crossdressers

Honestly I had no idea all these things were going to happen to me. Perhaps I was just innocent but maybe when you read on you will be forming your own opinion about that. I guess it was something I couldn't talk about at school, it's just that I get aroused by my own body. I was kind of aware that my bum was bigger than the other boys but when I progressed...

Wet Dream Pt. 03

by sissymissyct on Jan 28, 2020
Fetish

Gayle finished ordering items on line and checked the cam to be sure Georgia was asleep. The wetness in her panties told her what she needed to do. The payback for all those years that bastard cheated on her and how he had no idea what was coming to him, just made her pussy so wet. She was soon in bed enjoying her favorite toy. "I can't believe I slept so l...

Transforming Brent

by sissymissyct on Jul 9, 2019
Loving Wives

Katherine decides she wants to live with her lover Wendy. They come up with a plan to slowly change Wendy's husband, Brent, into their girly sissy maid full time. Will his resistance be broken? I put it in loving wives but it fits multiple categories. Will he will learn to love his new role in life? Yes, The narration switches between characters. If this bo...

Trip to LA Pt. 03

by gbr2004 on Mar 3, 2020
Fetish

This story contains forced fem, gay sex, discipline among other fetishes. If not your thing, please pass by this story. ***** I force myself out of bed and can't stop thinking about last night and even worse thinking about it continuing today. I go take a nice hot shower and that help some but when I come back into the room and see the pink pumps and the s...

He Brought Me Panties

by Cute Little Thing on Sep 14, 2017
Transsexuals & Crossdressers

Ok, here's a quick story and true at that. I was away on business one night and surfing for sex on Craigslist. The title of my post was "If I'm so strait then why do I want to get fucked like a girl?" It was a popular post and I got a bunch of replies, and a bunch of men wanted to fuck me. This made sense and I wasn't that surprised. I'm on the small side, 5...

Sorry Sissy You Lose Pt. 04

by LittleDickSissy on Apr 10, 2019
Fetish

Slave had been busy. Spending hours looking online for things for his Mistress. His little dick always swelling and throbbing as he went through pages of web sites, looking at heels, lingerie, hose, dresses, jewelry, etc. Mistress had tasked her slave. He was to purchase various outfits for her to wear on an upcoming trip. A work trip for his Mistress, but h...

Stacy Lancaster: Fond Farewell Pt. 01

by Boondocker42 on Sep 14, 2017
Loving Wives

The party had been better than she expected. Stacy Lancaster's co-workers at Laugher & Giles Plastics and Rubber managed to find an excuse to take a long lunch and get a little drunk just about every week. Usually, she found the affairs an irritant. Stacy didn't drink for one thing and some of the people she worked with tended to get a little obnoxious after...

A Working Sissy Girl

by keptsissy on Sep 16, 2017
Transsexuals & Crossdressers

I look up at my boots. Cute! Received delivery just day before yesterday, my boy friend hasn't even seen them yet. He'll like them, know he will. 3" spike heel ankle boots, very shiny patent leather, I look up at the one on my right foot. I run my hand down the thigh-high lace top seamed nylon coming up out of that boot and let my finger feel the boot heel,...

The Trap Ch. 05: A Proposal

by Paulateevee on Apr 13, 2020
Transgender & Crossdressers

Paula's old life crumbles but there might be light at the end of the tunnel. This is a transition story, taking our main character to the next stage of their life. As such there is no real sex in this chapter, sorry but it's required to set the scene for the next part. The usual disclaimer applied. Everyone is (well!) above the age of consent. This story...

Welcome Home, Ma'am

by Miss_Ds_slave on Sep 12, 2017
BDSM

He had been waiting his whole life to find someone like her. He had almost given up any hope that there was someone out there who could give him what he so needed. He had met a few women over the years that had been willing to try and give him what he desired, but it was usually just something they did for him, not something they enjoyed for their own pleasu...