Crossdressing Punishment Stories

32,309 results
Orientation
Length
Source
Infinite Scroll

Yes, Professor

by SerenVale on Sep 12, 2017
BDSM

With the noise of the station around me I didn't hear him come up from behind, until I could feel his breath on the back of my neck and his voice in my ear, "Hello, Little One. Are you ready?" I shivered as I felt his warm breath of the back of my neck and the feeling of his strong hand snaking around my waist to pull me closer to him. Such a simple phras...

Lucky Guy Pt. 04

by slimpic11 on Sep 14, 2017
Mature

I hope you enjoy this story. Please provide me feedback. This story includes contact between parent and an adult child that may be offensive to some. While not incest, if any contact offends you, please don't read. Edited by DRGRIFFIN, with my thanks! I reveal my answer to Eva and Emma The next day I worked on the project that I left somewhat less than...

The Assassin and the Sorceress Ch. 03

by StuckFanatic on Sep 26, 2017
Sci-Fi & Fantasy

Adrielle drifted into that twilight of half-wakefulness that so often follows a restless sleep. She had just been dreaming, but her dream was already fading away. Whatever pivotal task she had been struggling with mere moments earlier was now so distant in her memory she could barely remember what it was. With her dream retreating, reality was trickling begr...

Flight to Submission Ch. 10

by Cyberdiva68 on Sep 13, 2017
BDSM

Stephanie awoke as a shaft of sunlight speared its way through the curtains, bathing her face in warmth. As she opened her eyes she realised she had not slept so deeply or so well in a long time. All tension seemed to have left her body. She stretched languidly but was recalled to her circumstances by the tugging this elicited from her wrist and ankle cuffs...

I Discover the Real Me Pt. 01

by VanessaEvans on Jun 4, 2019
Exhibitionist & Voyeur

I discover the real me - and I like it. *** Part 01 When I was growing up clothes weren't something that I rushed to put on each day, except in winter. I just never saw the point, I mean it was warm enough to go without and it meant more washing for mum. Both mum and dad were always telling me, "Dani, go and put some clothes on." right up to when I reac...

A Submissive Wife and Her Big Butt

by Yuiqalla on Apr 3, 2019
BDSM

The clock alarm goes off insistently on my side of the bed, and I turn it off quickly so my husband Bill won't wake up. But, in his groggy state, Bill pulls me toward him and kisses me firmly on my soft, red lips, and he lifts my pink and white silk lingerie nightie over my big bottom and up to my slender waist, so he can caress and slap my large rear end a...

Torgan Wine Ch. 46

by Isemay on Dec 25, 2018
Sci-Fi & Fantasy

Tremendous thanks to Nthusiastic for beta reading, helping edit, and making suggestions/good catches! ***** Isonei beamed as the new servant, Rimathe, finished relaying a story of his mother schooling a young priest on his prayers at their temple when he was a child, telling him gleefully, "Draeseth says that Torgan women are strident, but I can't imagin...

Love Yourself

by neolim on Feb 12, 2019
Fetish

All characters portrayed in the story are 18 years old or older. ***** The Talk "Really Zoe? Like really?" Jessica said as she took a sit in her clean, white kitchen, "haven't we talk about this before?" She was clearly mad at the teen that sat across the table from her. Zoe had long, shiny, flowing red hair that cascaded down her back, reaching her ass....

Lucy, Nothing She Can't Handle

by paulb85 on Sep 24, 2019
BDSM

Lucy, A First Time The taxi was driving up the ramp out of Paddington Station. "Depending on the traffic it will take us about thirty minutes to get to Chelsea," said the driver over the intercom, which was necessary as the glass partition between him and my wife and me sitting in the back was robust and soundproof. "Thanks," I replied, noticing the butto...

Savannah's Hypnotic Socks Pt. 16

by Fibaro on Jun 24, 2019
BDSM

Chapter 19 Roxanne could see that Savannah was indeed very serious about her opening the door naked as she was. Still she couldn't actually do it. She had put up with a lot, but this was going way to far for her. She might be a huge pervert, but that didn't mean anyone else had to know. Savannah could see the inward struggle Roxanne was dealing with. She...