Sissy Hotel Stories

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The Guy in My Wife's Panties

by Candyboi on May 1, 2018
Transsexuals & Crossdressers

The catalyst for the paradigm shift in the relationship with my wife of twenty years was something that happened at the beginning of December - though, truth be told (as you'll see), there were several other naughty escapades throughout the autumn that really should have awoken me to the realisation that Carla was becoming the dominant one in our relationshi...

My Husband, My Slave

by SubbyHubby27 on Sep 19, 2017
Fetish

My name is Candice, I am 26 years old, and I am writing and sharing this story because my darling husband, Ricky, is too shy to do so. It all started in 2010. We were on a trip with another young couple our age. My husband's best friend Trey and his girlfriend at the time, Amber, whom he is now married to, were quite the partiers. Drinking, smoking, and...

Winning Big in Las Vegas

by marykay9 on Feb 6, 2018
Transsexuals & Crossdressers

I was in Las Vegas staying at one of the "lesser" hotels, playing the slots to kill time waiting for a "Shemale" show to take place. I thought that the review would attract other transvestites like myself and hoped that I might get up the nerve to wear my feminine clothes and mingle with other genetically challenged ladies. Unfortunately, a normal crowd surr...

The Vacation from Hell Pt. 02

by JamesMiehoff on Dec 11, 2018
Erotic Couplings

Copyright (c) 2018 James Miehoff, All Rights Reserved. This work may not be published whether for fee or free without this copyright. --------- This is one of a series of stories set in what I call Universe-J. Universe-J is very much like this universe with a few exceptions. First the people tend to be a little more sexual and less hung up on sex that...

Counselling Changed Our Marriage Ch. 02

by Quietoldie on Dec 1, 2017
Transsexuals & Crossdressers

I am grateful to another member of Literotica for the story line and about half the content of this story. I have thoroughly enjoyed the collaboration and have found working with a woman has informed my own writing. Chapter 3 will follow shortly. ***** Third Joint Interview Emily and I arrive at their marriage counselling session a bit earlier than their...

Hotel Porter to Private Maid

by KinkyBiLad on Sep 12, 2017
Transsexuals & Crossdressers

This is my first story, please leave comments below and tell me what you think, I hope to carry on the tale, if the readers like it. I suppose I should explain how I got like this. How an ordinary guy who was a porter in a hotel became the sissy, dressed as a maid, with a butt plug firmly inserted into my tight sphincter, on my knees, and throbbing 8" cut...

Sissy Hotel

by Prometheus on Jul 1, 2019
Transsexual

You have arrived at your hotel for the next week, it's a five star resort located next to the beach. You have checked in and are heading up to your room, a five star room that is. It has a brand new automated system that cleans, cooks, dresses you, and much more. You enter your room and immediately a voice comes on,"Welcome to your room John on behalf o...

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From Her Ex-Boss to her Bitch Pt. 03

by His_fag_wife on Sep 18, 2017
Transsexuals & Crossdressers

This story contains extreme fantasies of Fem Domme, watersports, cock sucking, forced bi, if these aspects are likely to upset you please do not read on. ***** Pete had been taken in by Rachel, encouraged along the way, with a little titillation and confessions of her bisexuality. For a married man he had admitted too much and allowed himself to be taken f...

Reminiscing on My Sissy Life

by Sjen451 on Nov 18, 2019
Transgender & Crossdressers

Things have gotten wild since my ex-wife mistress first took control. I've done everything she has requested of me. And with each accomplished task she only adds more challenges. I've never failed her yet, and yet she never ceases to ramp things up. In case you aren't caught up just yet, this all began one day when she stumbled across my secret fetish:...

Strangers on a Train

by Wendy212 on Jul 4, 2018
Erotic Couplings

One late Saturday morning in Bangkok: I see him on the crowded platform at Asoke: tall, lean, bespectacled, red-T-shirted, aged maybe 50. He, like me is a farang, a western foreigner. Me, female,—26 years old, dressed in floppy, short culottes and a loose blouse. As the elevated Skytrain pulls in, we exchange glances. He smiles. Or does he? Inside the train,...