Gay Punishment Stories

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Orientation
Length
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Infinite Scroll

Spin the Dildo!

by ZombieToph on Apr 9, 2012
Fetish

You share a nervous glance with your best friend, Jake, as you sit down on the floor, forming a circle around a large, purple dildo in the center, the girls giggling madly at you. "Well, you did say you'd do anything to get with me, James," said Erika, smirking at you from across the circle. "Here's your chance!" "I don't particularl...

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Dear Diary Ch. 01

by haunted_one2005 on Sep 17, 2017
BDSM

Dear Diary i was such a naughty girl today. All day long i was bitchy at work, yelled at my assistant and even threatened to fire the intern. i've been the youngest department head my company has ever promoted, and at 40 years old, that really says something about how seriously my employers take themselves. Daddy spoke on my behalf, and as a partner his opi...

Helpless Ch. 02

by whitemamba88 on Sep 11, 2017
Transsexuals & Crossdressers

"Miss Rhodes, it's time to wake up," said the voice from the speakers. I rolled over under the sheets and was immediately racked with another orgasm. I had fallen asleep with the dildos still inside me! The purple vibrator slipped out easily, but the glass dildo met some resistance as the mushroom-head reached my sphincter. With a little 'pop' the glass co...

Ram It Up Her Fat Ass

by Samuelx on Sep 1, 2017
Group Sex

The name is Kyle Jamal Francisco. My close friends and favorite family members call me K.J. I am the villain of this story. Who am I? In the eyes of the world, I am a tall, good-looking young black man currently living in the city of Brockton, Massachusetts. What is my profession? I'm a part-time Criminal Justice student at Bridgewater State College and a fu...

And When I Return Ch. 10

by sublocked on Sep 25, 2017
Transsexuals & Crossdressers

Saturday afternoon was sunny and seasonably warm, and before all the guests had arrived, Diane told Anna to report to the one large area of the back yard that had no shade. It was 1:00 and he waited, sweating slightly in his black maid's dress. The black stockings only added to his discomfort. The disadvantages of wearing a tight corset, panty girdle and sto...

The Punishment

by nat_rose on Sep 11, 2018
Transsexuals & Crossdressers

Fucking fantasy football. I knew there was going to be a punishment for finishing last in our fantasy football league. I didn't know my friends were going to be so extreme about it. Maybe I should've known. Now that we're all 30-somethings, I had seen the punishments escalate over the years. It started innocently enough-we made Greg sign up for and run a 5...

Miss Victoria, Sex Therapist Ch. 05: Lynn

by LilithDeVil on Nov 18, 2019
Fetish

Hello you naughty girls and boys! This chapter was going to come earlier (although I still may do some rearranging when more of the pieces are complete) but now I think it becomes chapter 5. We'll take a break from Gregory and get another glimpse of Mark soon, but now it is time to introduce Lynn. ***** Lynn practically fell back onto the couch and then c...

Cruel and Unusual

by TruthAndLove on Apr 3, 2018
BDSM

This is my first attempt at a story that plays with chronology. It mirrors the structure of the movie "Memento" (which you should rent, stream, or steal, if you've never seen it). There is a sequence of events in the present which is interrupted by a series of flashbacks. But the flashbacks themselves happen in reverse order. That is, each flashback is earli...

The Little Shop Ch. 02

by justincbenedict on Sep 17, 2017
BDSM

Phoebe smiled. "Soapy, I think I'm going to leave Nolan down there in the Kennel for another week." The now platinum blonde giggled, and her full breasts bounced a bit in the violet halter top. Soapy tried not to drool behind the counter. Damn she's looking good he thought, just like the tramps in my Narcotics Anonymous meetings. "But I thought your origina...

Angel's Story Ch. 03

by MistressMerry on Sep 17, 2017
BDSM

Marna watched the door close as the men guided her new slave to his cell. He wasn't completely broken, but very close. She looked forward to molding him. Marna crossed back in front of Gary. "Well, now that your friend has left, we can address your punishment." Gary looked up with weeping eyes, "B-but I've already ...," he began. "No you have not," stress...