Sissy Hotel Stories

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Sissy Hotel Play

by elliotsconfessed on Dec 24, 2018
Fetish

It was a Friday afternoon and I was feeling a little bored and some what curious... I had spent the last hour or so watching porn, but not just the usual straight type of porn I'd usually watch... For some reason I had an urge to watch men fuck other men and have guys dress up as girls and fuck themselves with toys! I was so turned on and a little confus...

Hotel Mix-up

by Woulditkillyou on Sep 13, 2017
Loving Wives

This story deals with Cuckolding, sissy, and impregnation. Please do not continue if any of these subjects offend you. This is a work of fiction, meant to be enjoyed. Please click back if this does not suit your style. In a fantasy, there are no STD's, and pregnancies become nothing once you stop reading. Sorry it is so long. I get carried away with the deta...

Sissy Maids & Sex Slaves Ch. 01

by RickyRooster on Sep 13, 2017
Fetish

Reader Notes This is a fantasy story patched together from a series of e-mails I have sent to a very sexy lady. She loves bisexual men and she loves men who wear panties. She is dominant but in a very genteel way, if that is possible. It's told and written in a different style than I usually employ. I feel this style is rather staccato, telling her what w...

Exposed as a Sissy Cuckold

by lapitup65 on Sep 18, 2017
Loving Wives

Last Friday we had a date scheduled. We were going out to dinner to meet Jay and we had a room booked at a nice hotel. Mandy and I checked in early. We relaxed for a while, sipping a glass of wine before Mandy headed off to take a bath and start getting ready. Just as Mandy settled into the tub, Jay sent her a text. I didn't read the text, I just took her ph...

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. "...

Sissy Idea Backfires

by danni5858 on Feb 12, 2019
Fetish

I guess I should have known it would come to something like this. Here I was, on my knees, clad only in pink thong panties, sucking an amazingly large cock for all I was worth, while three women "encouraged" me – verbally and with their hands, at times, pushing rather firmly on the back of my head. I realized that I had been headed in this direction for qu...

A Dream Come True Ch. 01

by searic on Sep 17, 2017
BDSM

Arriving at the hotel you had selected after a not-unpleasant drive up, I had plenty of time to obey my instructions. Carefully unpacking, I hung up and put in drawers my few vanilla clothes and all the sissy things you had selected for me to bring. How relieved I was to find myself able to be prepared and in position in advance of the time you had set for...

Dream Hotel Ch. 01

by gsdog1 on Sep 12, 2017
Novels and Novellas

Hotel La Rever , the hotel of where your dreams can come true. I had read the article online over and over again. The article said it was looking for workers like me that were welling to live at the hotel full time. It told me of a place that was made just for people like me who were looking for something different. Some place where I could belong and go to...

Sissy's Special Night

by mdw_dark_angel on Sep 17, 2017
BDSM

This girl was so excited as Master had agreed to a special surprise for sissy from angel. Master took sissy to work and came right away to fetch angel to return Home and ready things for angel's surprise..."Sissy's Special Night". Y/you see, this slave has belonged to Master... though one has not always retained one's physical collar... since Master first c...

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...