Gay Anal Punishment Stories

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Punishment or Pleasure

by Ewriter111 on Dec 10, 2018
Gay Male

I walked out of the county jail where I was in a holding cell for two and a half days very slowly and slightly bow legged. I had just turned 18 and made the mistake of mouthing off to a police officer during a traffic stop. It was early Friday evening and I didn't have a court hearing until Monday morning. I was put in a remote holding cell with three older,...

Punished Asian Shoplifter Ch. 04

by asianspankee on Sep 15, 2017
Gay Male

A few days after my second punishment session, I decide to return to your store for some much-needed shopping. While I am inside I spot the two college-aged employees doing some stocking and price-tagging work. They must have recognized me because I see them whispering to each other and snickering while looking at my direction. I feel so embarrassed I quickl...

The Journal Ch. 01

by thebionicman on Sep 1, 2017
Gay Male

The following account of late 19th century sexual torment was taken from the journal of Daniel Nickels, the Captain of the brig Waccamaw during the Civil War. The journal was discovered hidden behind a wall during recent renovations at the Bellaire Plantation in Savannah, Georgia, where the Captain lived after the war. I surveyed the chamber for the upcomi...

Chris Donaldson Ch. 05

by tazemebro on Sep 15, 2017
Gay Male

This story is about Chris and Justin, roommates and sophomores in college. Chris, only recently out to himself, began the new school year very eager for his first sexual experience. Justin, a dominant frat jock, was happy to provide that first experience, and quickly turned Chris into his live-in sub. Justin has a violent streak, however, which drove Chris b...

Little Jimmy Grows Up

by timmywells on Sep 14, 2017
Gay Male

In the interest of full disclosure I would like to mention that this story involves the following topics; rough, reluctant but consensual sex, anal sex, and both very dominant and completely submissive characters. This story takes place during the Summer of 1970 and involves a very shy, meek and socially awkward guy whose life is forever changed one day in...

The Making of a Master

by Littlepoppyhole on Oct 6, 2020
Gay Male

David lay on the dishevelled bed exhausted and still sweating after his recent sexual encounter with a man called Raymond. His hole was leaking semen onto the bed sheets. The sheets also gave off the aroma of anal mucus. This did not perturb David as he was deep in thought about the man he had served. He thought there was room for improvement in his sexual i...

How I Train My Bitch-Boys

by bjmichaels on Sep 14, 2017
Gay Male

The secret of properly training a boy is conditioning his mind; opening his mind to the endless possibilities of sexual pleasure. Some men train their boys through the use of force and physical intimidation--I strongly disapprove of that method. You desire, as your end result, a boy who willingly submits to your every sexual demand because he wants to—becaus...

Shipwrecked with My Buddy Ch. 01-03

by KinkPenguin on Sep 14, 2017
Gay Male

From the Author: Hello reader! I'm a long time reader of literotica, but have never created my own story until now. I have always wished someone would make a certain type of story, so finally decided to make them myself! This will hopefully be the first of many! My stories will likely follow one or more of the following. Anal, BDSM, Erotic Couplings,, Exhi...

Becoming a Cum Dump Ch. 06

by plyasian on Sep 14, 2017
Gay Male

The problem with going to bed early was that I woke up early. On a Sunday too. Uh. I opened my eyes giving up trying to get back to sleep. 7:35am. Fuck. I immediately went to my computer and waited. The last email that I read opened up. Don't jack off. You'll receive an email tomorrow at 8:00am. More instructions to follow. MT I was horny and wanted to...

The Ingram-Lewis Chronicles

by JASONSHOMOEROTICA on Aug 17, 2017
Gay Male

THE INGRAM-LEWIS CHRONICLES OLIVER'S FIRST SCHOOL DAYS A Homoerotic Short Story By Jason Land This is the first of a series of, stand-alone, short stories set in the early part of the twentieth century, concerning the life and times of members of an English upper class family, the Ingram-Lewis's. ***** The cane was tapping gently across a splendid pa...