Gay Chastity Stories

28,507 results
Orientation
Length
Source
Infinite Scroll

The Future in Our Stars Pt. 02

by WaxPhilosophic on Jan 28, 2020
Sci-Fi & Fantasy

Author's Note Like part one of The Future in Our Stars, this tale is structured more to make you think about 'what if?' than to get you off. Please consider that before you dive in. This story introduces each scene with fictitious quotes using the characters Dick, Jane and Sally. These are names that U.S. readers of a certain age may remember from their...

Somali Muslim Swingers

by Samuelx on Oct 24, 2018
Transgender & Crossdressers

"That was definitely a fun night," Hodan Yasser-Ali said to her husband Bilal Ali as they lay in bed together, basking in the warm afterglow of a good fuck. Earlier, they had a third party in their bedroom, and said third party definitely left a mark on them, in more ways than one. It was the couple's very first threesome, prompted by certain sexual revelati...

Frustration of Small Cock

by jamtby on Oct 16, 2018
Anal

In 2001 I suffered from a severe medical condition which required extensive surgery. The procedure saved my life but removal of my prostrate, batter, and extensive nerve damage left me without a functioning sex ability. My cock and balls remained outwardly normal but not doing what they were supposed to do. Despite the little blue pill, which only gave me a...

More Than a Trim Hair Salon

by fearthisss on Jul 14, 2020
Exhibitionist & Voyeur

I was new to the area, so I had to find all new replacements for things I took for granted not long ago. One of those things was a new hair stylist. Having longer-than-average hair for a male, and not wanting a cookie cutter haircut, it was difficult to find a stylist that knew how to do a decent job on a man with longer hair. On my way to and from work ever...

Eric's Dreams Pt. 01

by Genevieve_Ohara on Jul 14, 2020
Transgender & Crossdressers

The fact is, you'd thing life would be better, and easier for a guy who was born with a nice ass. A guy who caused other guys to stop and stare as he walked by. A guy whose ass was so hot, men would fantasize about the its curves, and later on jack off while remembering how it popped up and out, like only a young buff ass can do. An ass that made jeans look...

Me, Tommy and His Girl Ch. 04

by CuckFantasy69 on May 7, 2019
Group Sex

Dear readers, Thanks for all the comments and feedback! This is the last chapter of the Tommy story. I have other projects I'm working on and will post more stories soon. I love responding to e-mails so don't hesitate to send feedback and leave comments. I actively chat and send snaps to fans who enjoy my work and give me ideas or material. I'm open to writ...

I'll Show You Mine

by naughtygaywriter on May 7, 2019
Transgender & Crossdressers

He's so fucking sexy. I see him every day when I stop for my morning coffee. I try to time it so that I'm either behind him in line so I can ogle that cute pert ass. When I'm early, I make sure I loiter at one of the tables so I can see that boyish cute face of his. He just does it for me. He's everything I like about a man. Plus he has that air of mystery a...

How I became Robert's Boytoy

by AngeloMalDiaz on Aug 6, 2019
First Time

It started in fall of 1990. Robert and I were both college students and we had some classes together. I had a crappy dorm room, so we'd party at Robert's apartment. We just kind of hit it off as buddies. Robert's apartment always looked like a bomb had just gone off. We'd hang out and smoke weed and drink beer together, maybe watch some TV. Get drunk. Somet...

School's Out But Not For Me Pt. 02

by yenfrityler on Jun 15, 2020
Transgender & Crossdressers

This is the continuation of Part 1, which can be found on my profile. This is a work of fiction loosely based on losing my virginity to a drag queen when I was at university. We kissed for what felt like blissful eternity, drinking each other in as her body lightly writhed under mine. The feel of her warmth pressed tightly against me while she caressed the...

Oliver's Twist

by phoenixcinders on Jan 23, 2019
Transgender & Crossdressers

Hello! Thanks for clicking on my story, I hope you enjoy it! It contains lots lewd acts I should warn you about. Including but not limited to big giant black Transgender dick going into a small tight white boy butt. White boys being spitroasted. White boy sucking a woman's cock. A little bit of blackmail and coercion, but the white boy ends up loving it. All...