Crossdressing Punishment Stories

32,309 results
Orientation
Length
Source
Infinite Scroll

The Beat Meet

by shawalphamale on Sep 13, 2017
Erotic Couplings

THIS STORY IS INTENDED FOR ADULT READING ONLY ------------------------------------------- Evening, all. There's nothing like an old time copper -- and there was nothing like the fun and games that the old time coppers used to get up to. Somebody wrote that a policeman's lot was not an happy one -- but they were wrong. Young coppers used to get a lot, and e...

The Ascension of Will Ch. 01

by Varla_Pussycat on Sep 17, 2017
BDSM

This story is intended to be a biography of my friend "Will." Will becomes a slave to a dominate male/female couple and eventually finds his true calling as a Master to female submissives/slaves. I want to forewarn that the first three chapters of this story are not safe, sane, or consensual. There are also some gay male scenes. xxx *********************...

Submission Ch. 03

by H_Bateman on Sep 15, 2017
BDSM

N.B: Contains watersports. ***** The appointment was made. Now I had to struggle through the week that followed like a drug addict desperate for a fix. I couldn't concentrate at work; my notebook filled with crude, adolescent sketches of her hips, her breasts, her pussy suspended over my face. The evenings were the worst. Then there was nothing to distra...

Venus Ascending Pt. 04

by Oupa99 on Sep 15, 2017
BDSM

Chapter 12 Lisa stared into those eyes that somehow seemed to know her most intimate secrets. Those eyes that both made her heart pound in her chest, as well as, her nipples harden and thighs steam. Those eyes that promised the kind of love she always dreamed about, and those eyes that promised to keep her safe. She wrapped her arms around his head and sta...

Georgia Ch. 23

by VanessaEvans on Apr 4, 2018
Exhibitionist & Voyeur

Before you read this part I strongly suggest that you read the previous parts. It will give you the background that will make this part a lot more enjoyable. Part 23 As I was walking back from the café the next morning, Sebastian called me over and asked me if I was free the next day. I said that I was from late morning on so he told me that he and a coupl...

Six Degrees of Domination Ch. 02

by LadyMaleficent on Dec 10, 2018
BDSM

Six Degrees of Domination 02: I enjoy my Sexual Freedom by Lady Maleficent My sexual freedom I'd only ever had sex with three men before I met Edward; those were my first crush, my ex-husband and a brief affair. But including Edward I've now slept with nine. I don't envisage my number rising at that rate in future! My freedom to have sex with other people...

Sir Phillips and Mollie

by mollycactus on Dec 14, 2017
BDSM

Home from her part-time work, Mollie knelt quietly near the door. She was clad only in her collar, with its attached leash, and sexy white panties. Nothing else. Her heart rate was accelerating as the time approached for her Dom, Sir Phillips, to arrive home from work. She hoped he'd approve of her newest panties. He'd given her permission to search the inte...

Hunger Ch. 01

by darkgoddess2478 on Sep 17, 2017
BDSM

Maki closed the door of his hotel room and headed down the stairs to the street. The temperatures of the fall night were rather brisk and with the light rain misting down, the air picked up a distinctive chill. He pulled his head in closer to his body, trying to keep as much warmth as possible trapped in his trench coat and jammed his hands deep into his poc...

One...Two...Three.

by fantasywriter on Sep 16, 2017
BDSM

A lot of the stories I've written have been based on a club, a place I call "Illusions". The motto there is, "Where Nothing Is As It Seems". I think I wrote that thinking I could get lost in that place. No one to laugh or ridicule my feelings, only others would exist there as I, fulfilling their fantasies while perhaps finding love as well. It's always been...

Willing Captive

by Greyson35 on Sep 14, 2017
BDSM

I shifted my leg and the resulting clang sounded loud in the silence. I hadn't counted on the boredom. The hours of nothing to do and no stimulus and sometimes not even light, or sight. Nothing but my own thoughts. Sometimes not even my own voice. I could grunt if I wanted to, but the mouth piece locked into place by leather straps ensured my silence. It wa...