Sissy Hotel Stories

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Hotel Cum Sissy

by closetbecky on Sep 14, 2017
Transsexuals & Crossdressers

I was on a business trip in central Pennsylvania and decided to stop for the evening and get a hotel room before I continued on the early the next morning. I stopped at a hotel just off the exit of the state highway around 7:15 and checked into a room. I had noticed that there was a small bar open just off the lobby while checking in. I arrived at the room,...

Illicit Desires

by MistressRogueSpider on Apr 20, 2020
Transgender & Crossdressers

It was a hotel room like any other hotel, located in the cheap district. $28.99 a night could get you four walls, a "clean" bed, and a small bathroom with a tub/shower combo. The size was about the size of a studio apartment or a really small living room. Paper-thin walls meant privacy was low; you could guarantee the neighbors could hear so much as a whispe...

The Appraiser

by ctlthrmn on Sep 13, 2017
Transsexuals & Crossdressers

The seminar started at the local Marriot today. I, as the lead appraiser for my office was the main organizer for it. We had brought in one of the best appraisers in the East to share his expertise in appraising and developing a larger client base. The real estate market on Eastern Long Island was hot and I wanted to capture more of the $$$ it was spreading...

My Husband a Pornstar Ch. 03

by gtanya on Mar 20, 2018
Transsexuals & Crossdressers

Please read the previous two stories to fully understand and enjoy this chapter. If you don't want to read them, here is a brief description of what has happened till now: *** My husband was conned by me into exploring his sexuality and he finds out that he is bisexual. He also agrees on being a porn-star to earn a hell lot of money for us. After shooting...

How Low Can You Go?

by Compliant1 on Sep 16, 2017
Transsexuals & Crossdressers

Be careful what you wish for; that's a popular phrase in these Literotica stories. I found out the hard way the import of this message. I have always had a submissive streak a mile wide, but in my twenty-eight years I'd never experienced the feeling of completely surrendering to another person. With the Internet and its free personals web sites, I decided t...

The French Trip Pt. 02

by DrLuverotica on Sep 16, 2017
Transsexuals & Crossdressers

The gendarme's gave the impression they were used to this kind of shenanigans. One of them indicated we should all get dressed immediately. I fumbled about for my clothes, but couldn't find my boxer shorts - so I simply put my trousers over the silk stockings and Jo's panties I was wearing that were now filled with Pascal's cum. Jo rolled her skirt down, P...

It Happened in Mexico Ch. 03

by Angelscuck on Sep 16, 2017
BDSM

Angel watched the video of her husband in disbelief. Kelly had never shown any signs that he was gay before yet hear he was, begging to suck Joaquin's cock and to be fucked in the ass and looking like a sissy drag queen. It hurt her when her husband said he didn't want her anymore and called her a whore. She felt disgusted at the sight of him being fucked,...

A Birthday to Remember! Ch. 05

by searic on Sep 11, 2017
Transsexuals & Crossdressers

Decidedly put in my sissy submissive place by Mistress Leader Marta, I resolved to be much more careful and obedient. I also was aware of my excitement at her Dominance and power. When another participant sat down next to me, I was recovered enough to look up to say hello. I recognized him as one of those I had seen earlier standing around and chatting afte...

A Sissy Story

by PinkRebecca on Feb 21, 2020
Fetish

You always were a normal boy growing up, weren't you? Played some sports, although not to an extent where you stood out anywhere or made any teams. You had a normal friend group, as far as you knew atleast. You liked girls, like most of the boys around you, although you lacked the curage to talk to them. Well not to talk to girls in general but in a romantic...

Open in Reader

Recruiting of a Sissy Maid Ch. 13

by Sissy_Chantel on Nov 28, 2017
Transsexuals & Crossdressers

Chapter Thirteen: A Business Trip to an Adult Movie Convention, Carl and Chantel Consummate a True Loving Relationship. Carl says, "Chantel make sure you pack well but not slutty ok. I will have you travel with me as my girl friend and secretary. Dress nice but casual for our flight but of course still be an eye catcher ok?" Chantel replies, "Ok hun, I fig...