Gay Punishment Stories

51,366 results
Orientation
Length
Source
Infinite Scroll

Wild College Days Ch. 02

by Lionheart72 on Sep 16, 2017
BDSM

"You fucking slut!" Becky shouted. Startled by the outburst, Liz turned to look at the other woman. The two coeds were standing in the ladies' room of the Art Building. Liz had been standing at the mirror, straightening her hair and clothes to make sure she looked good for art class, particularly for the art professor. With her curly dark hair, attractive...

Sissy and Wimp

by 1Gratiano on Jul 14, 2020
Transgender & Crossdressers

1 Now the common belief is that any man who wants to wear women's clothes is gay, and that the heterosexual crossdressers who claim to be straight but "just like the feel" of silk panties and so forth, are being, well, less than candid. Be that as it may, heterosexual and homosexual crossdressers are in fact distinct psychological types. To be sure, ther...

Will and Katie: Katie meets Perry

by KatlynArgos on Sep 17, 2017
BDSM

Katie locked the door after Will left, and turned, her mind racing. When was Perry supposed to come? What if he came in an hour and the house was a mess? She knew if that happened there would be a punishment, her ability to show herself an obedient submissive reflected on him. Well first things first, she walked around opening all the curtains on the first f...

Julie's Surprise

by Sabineteas on Aug 19, 2017
Exhibitionist & Voyeur

Below this is a small email that I received from a young, college age girl from England named Julie. Julie had requested my assistance in exploring embarrassment and humiliation and I was slightly excited about the entire process. Julie had already done a task which could have had her caught naked in the open, but it didn't. But she also did not do the task...

Joshua & Sarah Pt. 03

by slimpic11 on Sep 15, 2017
Exhibitionist & Voyeur

This is a sequel to the story about Joshua and Naomi. That story ended with Naomi being transformed by Joshua her stepson from an obsessive religion lifestyle to that of a more normal person. In this story Joshua guides Sarah, his sister, to a new more liberated lifestyle. If sexual contact between siblings offends you then please do not read this story. Ed...

New Holiday Experiences Ch. 02

by theghostwriter on Dec 30, 2017
Group Sex

Breakfast finished Suchada put me in my place by ordering me to do the dishes and get the house clean while she and Lizzie disappeared off to have a shower. I was also ordered to have a pot of coffee ready for when they returned. During coffee I was told that I needed to prepare the other guest room for her brother and to also clean up their bedroom, bundle...

Tom Ch. 03

by Egmont Grigor on Sep 16, 2017
Novels and Novellas

A deal was struck. Tom would live with Shona and he'd work in the company's weakest area -- female apparel. She was already aware that Locus Thongs (Didn't he mean Lotus Thongs? Shona had smiled) were currently the market leader. The two partners greeted Tom's recruitment with sighs. "Shona occasionally comes in with a stray," Ben yawned. "Earn your salar...

Women's Studies 201 Ch. 03

by cynthiablaine7 on Sep 14, 2017
BDSM

This story does involve bodily functions, so if that is a problem for you, read no further. ***** Prof. Kate Sullivan had now been teaching her Women Studies 201 course for two weeks and was ready to take the course, which was entirely populated by women—juniors in college, so they were all at least 18—a step further. The lithe blonde had spent the first...

Cock Sucking Jail Whore

by RobinTVDaniels on Sep 15, 2017
Transsexuals & Crossdressers

I've always known that I was not meant to be a guy. Being sexual curious I would look at porn mags like any one does. At first it was just magazines with pictures of naked woment. It was when I ran across my first Hustler magazine that my life was changed forever. Seeing pictures of studly guys with big hard dicks and women on their knees about to suck or be...

DUYA 03

by Horhay_J on Aug 31, 2017
Fetish

Mrs. Heyward had given Rachael the rest of the week to recover and to study more. Rachael had spent the time re-reading everything. She was also allowed to visit the punishment and reward rooms just to observe and see some practices applied. She also sat in on a few classes. These were much more in her comfort zone, as the classes were fairly normal for the...