Gay Chastity Stories

28,507 results
Orientation
Length
Source
Infinite Scroll

Vacation Expectation

by IPleaseYouTease on Oct 6, 2020
Fetish

The wife's side of a conversation with her husband as she gets packed to go on a 10-day vacation with her lover and leave him behind. ~~~~~~~~~~~~~~~ ~~~~~~~~~~~~~~~ ~~~~~~~~~~~~~~~ ~~~~~~~~~~~~~~~ "Okay Dearie. Up on the bed. It's almost time for me to leave. I have a plane to catch. Don't you worry. I know that once you're done binding your hands and fee...

Santa's Sweatshop

by Varlance on Mar 10, 2021
BDSM

Santa's Sweatshop is an adult-only 18+ game that features fictional characters in various situations of a sexual nature. This includes gay (male on male) sex, non-consensual sex/rape, oral sex, anal sex, bondage, chastity, spanking, pain, body-writing and insertion of toys. You should not play this game if you are not 18 or older, or if you might find the ab...

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Mistress Aimz

by hyperpress on Aug 17, 2017
Fetish

Mistress ordered me into my chastity device. I complied. "you may not cum this week," she told me. I didn't. I was good. I used depilatory cream and removed all my leg, clit and pussy hair for mistress. It was Friday. She told me to take off my chastity and jack off into a glass. She said I could cum as much as I want Friday and Saturday, but to cum in th...

Master Knows Best

by justincbenedict on Sep 17, 2017
BDSM

Shane moaned as Ansel licked the underside of his balls and then used tiny bites back up his shaft until he got the swelling head. Ansel licked his glans, and then deep throated and constricted my jaws for just the right moment, and Shane wiggled his thighs and shot into Ansel's mouth, and Ansel swallowed greedily before pulling my head off his bloated coc...

Black Bulls in Chastity!

by Samuelx on Oct 3, 2018
Interracial Love

Meet Bartholomew "Bart" Jones, a big and tall young Black man living in the City of Ottawa, Ontario. Born in the City of New Orleans, Louisiana, Bart moved to the Canadian Capital to expand his horizons and explore new things. He had a Business Management degree from Louisiana Tech University, and felt like giving life in Canada try. Life in Canada had alway...

All About Me!

by Freakboy80 on Sep 13, 2017
BDSM

Lisa and Jim were smiling uncontrollably as they left the town hall. "I can't believe we are finally married!" expressed Jim as he held the car door open for his new bride. "I know I'm so happy." replied Lisa. Jim and Lisa had been dating for almost two years. Lisa is a nurse and Jim is a cop. They met one night when Jim had to bring a prisoner in for med...

My Initiation

by lockedupslut on Sep 13, 2017
Transsexuals & Crossdressers

(This story is a work of fiction. If you don't like erotic stories that contain cross dressing, heavy gay themes and water sports please just don't read it. Thank you.) * I was determined. This weekend it would happen. I would loose my gay virginity and complete manhood. The hard way. Tonight would change everything. Until now I've never had sex with a ma...

My Husband a Pornstar Ch. 03

by gtanya on Mar 20, 2018
Transsexuals & Crossdressers

Please read the previous two stories to fully understand and enjoy this chapter. If you don't want to read them, here is a brief description of what has happened till now: *** My husband was conned by me into exploring his sexuality and he finds out that he is bisexual. He also agrees on being a porn-star to earn a hell lot of money for us. After shooting...

Butch's Bar Slut

by sissymissyct on Jan 7, 2020
BDSM

(A bit darker than most of my tales. It would fit in gay or nonconsent as well. Gay sex, sissy sex, chastity and punishment.) *** I love this bar, Butch thought to himself as he finished another beer. And why shouldn't he. It had everything a Leather Bear could want. Plenty of hot men in leather, and some women as well. A bunch of trans girls and some siss...

Blackmailed

by Hc225 on Jul 29, 2020
Exhibitionist & Voyeur

It was so stupid of me to be so risky. I had always considered myself to be bi, but had never explored the gay side of it. When I finally went off to college I decided to give it a shot. I had put out an ad onto Craigslist looking for a guys cock to suck. I gave a quick discription of myself "brown hair, blue eyes, 4.5 in cock." That was it. I want...

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