Sissy Hotel Stories

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Getting Some Helping Hands Inside

by Cumfusion on Sep 14, 2017
Anal

[This is a sequel to 'Cream Buns after the Party'] It had been scary towards the end of the party as I knew, if any of the hotel staff had walked in, I would have been instantly dismissed in disgrace. That's kind of not what you need in your first job after college. I had been asked to be bar tender in one of the hotel function rooms. I didn't know it wa...

A Birthday to Remember!

by searic on Sep 11, 2017
Transsexuals & Crossdressers

Part I We had been married for two years, and my birthday was approaching. The year previous we had spent three days in New Orleans, and Marita had reigned as my Mistress Queen as we celebrated my birthday on the special outing. It was a special birthday, indeed! Given her love for me and immense creativity, I knew this year would be special, but I couldn'...

My Dom's Decisions

by davesubboi on Oct 12, 2017
BDSM

The thought of being submissive and letting another superior being guide, direct and change me has become one of my driving desires. Over the past 15 years I have realized I am much better at pleasing others and have determined based on numerous online doms/master/mentors that I really should not care about my own pleasure if I can serve another and give the...

Let the Spirit Lead Ch. 01

by purplepantiesgirl on Jun 10, 2019
Transgender & Crossdressers

Andrew had sunk somewhere below rock bottom he felt. Life had become miserable. Nothing in his existence was going well. Keeping with the adage of Americans hitting the open road in times of tumult, he followed suit and packed some of the belongings he still owned. During his recent divorce, he'd acquiesced and signed over much of his net worth to his now fo...

A Birthday to Remember! Ch. 04

by searic on Sep 11, 2017
Transsexuals & Crossdressers

A Birthday to Remember Part 4 In some ways the meeting room in which Haley and I found ourselves looked typical of the species: there was a long table labeled "Welcome--Registration"; A couple of folks behind it helping individuals sign in; a coffee urn with cups, cream and sugar; next to it a selection of cookies; and a place for seating with whiteboard,...

A Visit to a Mistress

by fun4all6969 on Sep 19, 2017
Fetish

I have always craved humiliation ever since I was with a girl who humiliated me for my premature ejaculation and my small penis. I saw an ad online for a girl who loves submissive guys and we chatted back and forth for about 2 weeks before my business trip took me to where she lived. She told me it would be $250 for the domination session and that I had to p...

The Making Of A Good Slut

by Tom Bishop on Aug 18, 2017
Fetish

Always had dreams of dressing in fem clothes not to pretend to be women but to feel sexy and soft would dress when alone and pretend to be serving a man. I’m 53 now and met guy a year and a half ago who brought all these dreams out in the open. I was at a work convention out of town Had to spend quite a bit of time with Younger guy named Ken The work part w...

Panty Boy Ch. 08

by vieuxbleu202 on Sep 12, 2017
Transsexuals & Crossdressers

I had to go out of town for a meeting; my ass was very sore from the night before. Those girls had really given it to me; my asshole was left a gaping hole. I could feel the "lips" of my asshole for over an hour last night, all big and puffy and open waiting for more. I felt like a total whore and I loved it. I took three huge cocks and was left begging for...

It's not All About Her

by Copycat88 on Sep 17, 2017
Fetish

DISCLAIMER: This story is about Femdom, Cross Dressing and Cuckoldry. If these topics offend you please don't read it... Just move on. No need to vote or comment if this isn't your "thing". If these appeal to you, please enjoy. ***** -IT'S NOT ALL ABOUT HER- I absolutely hate trying to get anything off of my husband's computer, but here I was trying and...

Loaned Out

by Valsslut on Sep 16, 2017
Fetish

Yesterday Lady Valerie loaned me out to her friend. Terrified beyond belief, I drove to a large hotel, rode the elevator up to a large suite and ordered to undo my pants and prove I was wearing panties at the door. I was scared about being scene in the hall worse the humiliation was turning me on so much my clit got hard. Lady Valerie had taken my chastity o...