Chastity Gay Stories

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Orientation
Length
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Infinite Scroll

Letter from Raleigh

by justincbenedict on Sep 17, 2017
BDSM

Dear Shoeblossom: What will happen now? Yesterday, Pebbles summoned me from the closet (I undress and kneel there as soon as I come in from work) and instructed me to put on my pink panties and my pink and purple lacy floral print baby doll nightie and high heels. I walked into the living room, and there was Peb, and her sister Faye, and the six guys in my...

Ms. Alexandria - Interview No. 02 Pt. 01

by gasissynora on Nov 4, 2019
Transgender & Crossdressers

This is the second part of the Ms. Alexandria series. I believe it will stand alone, but will make more sense if you read the first part of the story, "Ms. Alexandria: The Interview." * Ms. Alexandria: The Second Interview -- A day out. Part 1 I get home from the interview, feeling that it went very well. I am also extremely horny so I strip down to my li...

Boobgasm Bonnie

by imhapless on Sep 11, 2017
Loving Wives

I'm starting out this tale in the middle by relating some thought-provoking information about female orgasms. This was information that I never knew until I was twenty eight years old, and most of you probably don't know now regardless of your age. This information is important to understanding my story. According to an MRI study published by the Journal of...

Lucy's Revenge Ch. 04

by Cynthia_D on Sep 18, 2017
Transsexuals & Crossdressers

I should have called in sick the next day but thought by concentrating on work I could take my mind off the previous two days' events. My jaw was sore from keeping my mouth open most of yesterday afternoon giving blowjobs and my ass hurt so much from being fucked at the truck stop I could hardly sit. But that's what I had to do to pee since Lucy left my cock...

Danni Ch. 02

by Coder3445 on Jan 20, 2020
Transgender & Crossdressers

This story starts where the last left off, read Danni to understand what is going on in this story. Of course all character are above the age of 18. The following story contain feminization and female domination. * Also another description Tara, Danni's Mother Unlike Danni Tara had tanned skin, she was five foot four inches tall. She had green eyes and...

The Support Group

by justincbenedict on Sep 17, 2017
BDSM

"Victrola can be loving but she is also quite overbearing at times," Roger said wistfully, "And when I complain, she whips me and adds days on my chastity. I can't Galahaden ask her to go to counseling with me!" The members of the Men's Chastity group muttered sympathetically, but Rusk could tell it was all bullshit. Men didn't need to be in therapy tog...

Black Cuckolding Dreams

by Samuelx on Sep 11, 2017
Group Sex

Sometimes what you're looking for is closer than you think. Take my fiancé and I for example. My name is Stacey Walton and I'm a young Black woman living in Milton, Massachusetts. I studied business administration at Bay State College and earned my MBA at the University of Massachusetts at Amherst. Presently I work for a real estate company in Brighton. I me...

The Pantysissy Diaries Ch. 02

by JPantyboyVSL on Jun 5, 2018
Transsexuals & Crossdressers

This is a 3rd person fiction story about my fantasies of being a Pantysissy. All characters in this story are made up, and are all over the ages of 18. To better follow this story read The Pantysissy Diaries Chapter 1 before reading chapter 2. *** The Amtrak train Jaymie was onboard with his new Mistress, Sydney had just pulled into NYC. Jaymie had to get...

Caitlin and Mistress Vicky Ch. 02

by Jemina004 on Sep 19, 2017
Transsexuals & Crossdressers

I hummed softly as I put the finishing touches on the salmon. Teriyaki salmon was my wife's favorite dish and it filled me with pride to know that I was making her happy. My mouth watered slightly as I arranged the tray. (I would only be having a salad myself, as I had to maintain my figure.) Taking out a pocket mirror from my apron, I checked myself to ma...

Rosa subrosa

by ValoryG on Apr 8, 2019
Transgender & Crossdressers

I first saw Rosa on a kinky-sex dating site. I, as a 35-year-old recent divorcee, had visited it "just out of curiosity" -- or was it rather because I sought a little titillation? I certainly never expected it to lead to anything. I just thought I'd peruse some photos and fantasize about meeting some off-beat women. I ended up beating off looking at a few of...