Sissy Hotel Stories

62,092 results
Orientation
Length
Source
Infinite Scroll

The Landlady Pt. 01

by Manndee on Apr 3, 2018
Transsexuals & Crossdressers

I had been lodging at the address for 7 months now. When I first saw the advert, it made me smile because the lady advertising the room seemed to be so eager to have a lodger. You could see it in her photo. It was not my first choice when I looked through the properties that were available online, but it was the cheapest, and funnily enough, it looked the ni...

Mistress Chantel, Tranny Dominatrix Ch. 15

by Sissy_Chantel on Sep 19, 2017
Transsexuals & Crossdressers

Chapter Fifteen: We Meet Each Other's Parents and There Is A Wedding Ready to Go. [Sunday late morning]. "How many sissy maids have agreed to come clean for us Hun?" Kerri asks. "Three little sweetie maids Babe." I smile and reply. "They will be by on Wednesday before our Friday wedding. They are all so excited to play sissy house maids for us while t...

Tranny G is a Nymph

by Creamyirish on Sep 16, 2017
Transsexuals & Crossdressers

It has been a long winter and I have not seen Chris or Tranny G in a long time. Chris lives in a place too cold and it is difficult for him to travel. During those cold months, and without my being near, G has been in hiding. I have hinted, begged and pleaded with Chris to find a weekend to travel to see me. He needs a break from work and the cold and I need...

Recruiting of a Sissy Maid Ch. 15

by Sissy_Chantel on Dec 22, 2017
Transsexuals & Crossdressers

Chapter Fifteen: Life Changes but Normalizes Monday morning, Carl and Chantel are up and at it, breakfast in the hotel restaurant and then a shopping excursion to an are Jewelry store for Carl to buy Chantel her engagement ring. Dressed sharply but casually Carl in a white button down shirt, Khakis and black walking shoes. Chantel a white turtle neck, black...

Dreams

by DrLuverotica on Sep 25, 2017
Transsexuals & Crossdressers

"Hey! Hey! Wake up, wake up!" "What? Jo, what is it? What's going on?" "I think you should be telling me that!" "I don't understand." I was slowly coming round now, But I was still mystified as to why my wife had woken me at 2 a.m on a Saturday morning. "Erm your cock is as hard as nails and you were waving your ass in the air," Jo said, starting to laug...

Unknown Waifish Model Ch. 01

by Couture on Sep 12, 2017
Transsexuals & Crossdressers

We lay curled up to one another in the hotel bed, Sandra and I. I looked forward to the day we'd no longer have to make do with hotel beds and the occasional foray to my apartment. Yes, one day soon, she would leave her bastard of a husband and move in with me. God, she was beautiful. Her blonde hair was mussed up, as she lay on the pillow. Her face had th...

A Cuckold, Two Blondes, and BBC

by geronimo_appleby on Apr 3, 2019
Novels and Novellas

Okay, a word of warning from the off -- if you're going to be offended by a white cuck husband whose wife gives herself to a group of black men, don't read this piece. If a scene that features black men impregnating white women turns you into a seething ball of outrage, don't read this piece. If you're going to get all snarled up with hate at descriptions of...

My Week with Laurie

by robbie3 on Sep 14, 2017
Fetish

Laurie was a co-worker who had recently been appointed the training officer in our government agency. As such, she had acquired a nice private office, in which I found myself spending more and more time. We had always been friendly, but lately were exchanging comments of a more personal nature. I'd call it meaningless flirting. Laurie was a year or two young...

The Sissy Models

by neverless on Mar 12, 2019
Transgender & Crossdressers

Editor's note: this story contains scenes of incest or incest content. ***** "It's not something I've ever done," Daddy said, with a frown though the fact he hadn't laughed it out of hand meant I knew I had a good chance of persuading him. "There's a first time for everything," I answered. "What if someone recognises us, Ricki?" he asked. "They won't"...

The Capture of Sweet Pussy Ch. 03

by SirStroker88 on Sep 17, 2017
BDSM

Chapter 3 – Donna's Story 'Damn Sid, you're right, she is a beautiful sight." Donna was looking down at Pam Martini, the bitch she knew from the office. What she saw now was a frightened young lady on all fours wearing nothing but a collar and a blindfold. She was leashed to a whipping post and quietly sobbing to herself. Donna knelt and stroked Pam Sweet...