Gay Chastity Stories

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Orientation
Length
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Infinite Scroll

My Master was a Matchmaker

by justincbenedict on Aug 8, 2018
BDSM

SAID THE SPIDER TO THE FLY JULY 2018 STORIES THE MAN FROM MOUNT EIDERDOWN Cheverus Glass knelt before Specs, looking a little ill at ease out of his gray suit from Rogers Peet. Cheverus began stroking his penis slowly, biting his tongue as he did it. "Haven't touched this in a long time." Cheverus said, looking up at Specs, who was a little bored. Chever...

A Sissy is Born Ch. 02

by gtanya on Oct 13, 2020
Transgender & Crossdressers

Author's note: This story is the second chapter of "A sissy is born" series. Please note that it is a very slow build up and if you are looking for some hardcore sex right away, it is not for you. Please leave your comments to help me improve. It was a fairly uncomfortable couple of hours of the train ride with the constant staring of Mr. King. His gaze som...

The Contest

by justincbenedict on Sep 13, 2017
BDSM

Benny Price looked a bit discomfited as he entered the Marathon room. There were four guys, kneeling on pillows... Yes, naked as the day they were born, jerking their dicks VEERY slowly. They looked exhausted, and Benny looked at Nora, his beautiful fiancée, and wondered what the hell he was doing here. "You were so busy with work, you've missed the la...

Created in the Image of a Superior Being Ch. 04

by alyssawinters on Apr 22, 2020
Transgender & Crossdressers

The name of the CD bar he owned was called 'Over the Blue Moon'. It was the name of the one and only play Gary Stanisloph Kowalski the owner had been in when trying to make it as a stage actor 16 years previous. If he got drunk enough like the character artfully portrayed by 'Brando' he would playfully cry out 'Stella...Stellll-aaaaa' to the amusement of his...

First Time for Daddy's Girl

by JennaJay919 on Dec 17, 2018
Transgender & Crossdressers

I had been talking to him for a while now. This man. Daddy. Somehow the constant barrage of pornographic images and sissy hypnosis had taken a hold of me and brought me to the point where I had actually begun to develop a relationship with a man. I had never thought of myself as gay, or had thoughts about men. I was the typical A-student, moderately athleti...

Soames's Submissives: The Game

by justincbenedict on Sep 17, 2017
BDSM

Calvin knelt, naked on the Consequences square of the game... Looking at the sexy girl in the cheerleader outfit, and her muscular companion, both of them in their early twenties, but otherwise looking very much like the kids who awed Cal in high school. Cal had told Soames (in confidence) that once, a girl had asked him to the movies, one he'd had in his...

Cuckold: Mia and Greg's Story

by glmike523 on Sep 17, 2017
Fetish

For the last 5 years Greg has been a cuckold husband. It all started one evening when he and his wife Mia decided to relive the spark they once had by going to a darkened parking lot and to have sex in their car. Mia is a very attractive woman and Greg is a handsome man. Greg looks a lot younger than his 42 years but if there is any downside to Greg it is h...

Captivity

by Boomerang7 on Sep 26, 2017
Fetish

On Monday my balls still hurt like crazy, even in the evening, then on Tuesday the pain wasn't quite so bad, on Wednesday I felt I could risk having a quick wank. I was working at home that day, and my wife had gone to London on the train, so I was free to delve in the linen basket for a pair of her used knickers. I found a beige pair, not thongs, which are...

The Sports Enthusiast

by justincbenedict on Nov 18, 2019
BDSM

Becket Hastings hung upside down, suspended by his ankles. Becket's hands were cuffed behind his back, and he was utterly naked. This seemed to happen every sports season. Cinnamon, Becket's enchanting "platonic" housemate was a "sports atheist" and couldn't stand him running the idiot box, watching those damned games. At the same time, Cinnamon didn't wan...

Pomp and Circumstance Ch. 01-05

by SevMax2 on Jul 14, 2020
Sci-Fi & Fantasy

Chapter 1 I was very much bored with this date, yet another one that a friend had talked me into, though admittedly I had never met the young lady in question. She seemed nice enough, granted, but I could tell that she was eager for a more serious commitment than was sensible by my thinking, plus women like that were likely prudes. I didn't have time to was...