Gay Punishment Stories

51,366 results
Orientation
Length
Source
Infinite Scroll

Size Matters

by idahoboy on May 5, 2015
Science Fiction

Adam rushed into his room after school. His dick was already straining in his pants. It seemed like it was getting harder and harder to make it through a day of school without jerking off. The young man had taken to blowing a load in the toilet at lunch. Today, he couldn't find an empty stall before the bell rang. The boy dropped his pants wrapped his hand a...

Open in Reader

A Sissy in the 22nd Century

by JerkGently on Jul 1, 2020
Transsexual

In a future not too far flung, humanity has progressed to a stage where almost all production and provision of society’s needs is automated. With no need to work, all citizens are instead driven to find lifestyles that fulfil their own and each other’s fundamental desires. This is achieved by the medium of an overruling system of artificial intelligences and...

Open in Reader

Across the Rooftops - Again Ch. 02

by Drmaxc on Dec 19, 2018
Exhibitionist & Voyeur

The conversation resumed the next morning on the walk to the beach. Coffee and breakfast had been pleasant enough. They had been naked, had held each other's balls by way of greeting but had not had the pleasure of voyeuring so far that morning. The door to the nearby rooftop had stayed resolutely closed and, even through binoculars, a closed door did not en...

Across the Rooftops - Again Ch. 04

by Drmaxc on Jan 1, 2019
Exhibitionist & Voyeur

The two men sat in the darkness of Ed's rooftop, a finished meal before them. "Well," said Ed, "that was quite a day. I hadn't expected that." "No, just a bit of ogling, not getting involved in their fantasy games. That was out of the blue. I never thought we had a chance of cumming in Steph's mouth. Perhaps by her hand but not that. They seemed to enjoy t...

Executive Submission Ch. 02

by MistressVal on Sep 14, 2017
BDSM

Susan sat at her desk with a mixture of anticipation and resentment. It was Friday evening, and Susan had already locked the office doors. All of the other office employees left for the weekend. Susan was employed during the week by her mistress as her mistress' legal assistant. She looked forward to Friday evenings as the start of her weekend with her mistr...

Three Parts of Punishment

by fleshboy on Sep 13, 2017
BDSM

Last night was a late night out with the guys. I was pretty tired and could not wait to take a nap. We had been busy cleaning the house all day. I knew my wife had some errands to run so I waited for her to leave. I wanted to lay down for at least an hour or so and catch up on my sleep. She took off about twenty minutes later. I wasn't sure how long she wo...

A Sissy Saga Ch. 06

by Snurge on Sep 15, 2017
Novels and Novellas

The following day was Sunday. Margaret Pardoe never resented being duty-tutor on a Sunday, it was the only day of the week without any kind of formal lessons and she was only responsible for overseeing the pantywaists when they strolled outside in the grounds. That said, much of the time she could idle away in the headmistress's study in pretence of monitori...

Beta Male Slave Academy Ch. 02

by Tazokm on Jul 13, 2020
BDSM

After being blown and locked, Miss Carly explained to me that the compound we were at had over a hundred rooms and approximately 50 current residents. She began walking me to a room where I was to keep myself preoccupied until they had prepared my sleeping arrangement. I walked butt naked behind Miss Carly down a high-ceilinged hallway. Her ass was absolutel...

The Pledge Mistress Ch. 23

by caligula97236 on Sep 14, 2017
Novels and Novellas

Chapter 23 -- Pledge Ken's servitude The pledges returned to their cots at 5:00 a.m. Ordinarily they would have had to get up for PT in just a few minutes, but that particular morning they were allowed to skip the mandatory exercise session. They had endured plenty of exercise already, having spent the hours between 10:00 p.m. and 4:30 a.m. in constant phys...

Cleaning Her Kitchen

by michaelssubmission on Sep 17, 2017
BDSM

"Today you will learn to clean the kitchen, but more specifically how to clean my kitchen," she said, looking directly at me. "You will begin by going to the cabinet above the stove and removing the box that is there. Place it on the floor next to my feet. I reached up and opened the cabinet. I am not tall and it meant reaching up on my toes. Naked while sh...