Gay Punishment Stories

51,366 results
Orientation
Length
Source
Infinite Scroll

The Ventriloquist

by justincbenedict on Sep 16, 2017
Humor & Satire

THE VENTRILOQUIST (Or, "Which one's the Dummy?") Okay, like, I don't know why it happened, but it was fuckin' weird, man. I was sitting in the lounge of Texas Tommy's Boi-Toi Ranch, when they got an outcall for a "Big strong, hustler". As Mickie at the desk said, they wanted the biggest boy there, ALL OVER. Next to "Detroit Half-Smoke" Willard, who's...

P.A. for a Day

by susanxdresser on Sep 13, 2017
Transsexuals & Crossdressers

The gates swung closed behind Charles as he slowly drove his car up the sweeping driveway. Even though he was looking forward to the erotic delights which were in store for him that day, the cares of the world seemed to weigh heavily on his shoulders. As he drove up to the garage he mused about the dullness of the life which seemed to stretch endlessly befo...

Deepika's College Life Ch. 08

by sin138 on Sep 26, 2017
Exhibitionist & Voyeur

I am sorry for the lateness of this chapter. Unfortunately, I couldn't get time to write the story. The next few chapters may take time too, but I will try to get them in as soon as possible. This chapter is a bit smaller than the others. I am currently editing the next chapter and hope to get it out soon. I want to thank the people who enjoy story so far, a...

Betty's Revenge Ch. 02

by BobDogwood on Sep 13, 2017
Exhibitionist & Voyeur

Chapter Two When Betty stepped lively down the corridor to her office early the next morning, she was surprised to observe Renée already waiting for her standing by her office door. Renée was well known for not liking to arise early. ‘Oh ho! What do we have here?’ Betty wondered. “Good morning, Renée,” Betty maliciously grinned at her. “How good to see yo...

Fantasies

by needysub on Sep 16, 2017
BDSM

"Hello?" I called, tentatively walking forwards in to the dark. "Anyone here?" My voice echoed back to me, the hall I was in seemed quite big. I didn't even know why i was here. I had gotten a text from my girlfriend, Kirsty, about an hour before, telling me to come here, to come in and close the door. I had never been here before, so i had no idea what to...

Julie's Tasks

by Sabineteas on Aug 19, 2017
Exhibitionist & Voyeur

Julie's Backstory I was asked in an email to relate Julie's back story. I don't really know what the purpose of the request was, but here goes. Julie, her name ostensibly, emailed me feedback to one of my stories. She expressed an interest in embarrassment and humiliation and over several emails and discussion of things that she could do a few were decided...

Sweet Gwendoline Ch. 19

by Schlank on Mar 2, 2020
BDSM

When I returned home, Lyndsay took it easy on me for the first few days. Julie has missed me and wanted to spend time with her best friend. We reconnected by swimming laps in the pool, watching television together, chatting endlessly, going window shopping and of course having shower sex, which now seems to be Julie's favorite way to achieve orgasm. On my...

The Lilac Hotel

by LaurelAspen on May 15, 2018
BDSM

The Hotel is the epitome of discretion; you'll find no advertisements or marketing of its services, not even a sign over the front door. The guests are famous, powerful people who demand -- and can afford -- a strictly private stay. Consequently this establishment is discriminating of whom it allows across the threshold. Making a reservation is not a forego...

Such a Deal Ch. 04

by Angelscuck on Aug 31, 2017
Fetish

Sasha had me strip down while she cleaned me up. I was then told to put on a shorty nightgown. I was then taken to a bedroom and allowed to rest. I was exhausted. We had been at it for seven hours. I was awoken at mid-night by Sasha and dressed as before with fresh makeup applied to my face and hair re-arranged. "We have company and you are the entertai...

Bisexual Black Man in The Hood

by Samuelx on Sep 15, 2017
Group Sex

Marcia Brown comes home from work. She's been working all day at the Cheesecake Factory and now she wants some rest and maybe a bit of excitement. She almost got fired today for getting into a long argument with Sarah, the skinny white woman who runs the place where she works. Marcia is a loudmouth who often snaps at customers when she gets stressed out. Als...