Chastity Boy Stories

108,647 results
Orientation
Length
Source
Infinite Scroll

A Better Life through Chastity

by chlomo on Aug 31, 2020
Transgender & Crossdressers

I wrapped my arms around Sophie and squeezed her tight as I shot my load inside her. She was perfect; large breasts a peachy rear all in a pale curvy frame, her long brown hair framed her big welcoming eyes gleamed up at me. I didn't deserve her. I sighed heavily and sank into her as she smiled and gently stroked my hair. I had failed her again, I knew it,...

Adventures in Buttermilk Falls

by justincbenedict on Sep 17, 2017
BDSM

Merritt came into the Dungeonopolis gift shop with Darrell's chastity belt in her hands, looking exasperated. Hinton smiled. He enjoyed Merritt, she was fun and cute, and they had a flirtatious relationship, though of course he was a good forty five years older than she. Hinton actually was a retired mechanical engineer; he'd had a hobby of building and r...

James' Master Ch. 01

by hs62663 on Sep 17, 2017
BDSM

James will always remember the 15th of December 2013 for this was the day that he became the slave of his uncle. James was an ordinary teen who was waiting for University offers to be received. It was on this day that his uncle decided that James would no longer be a free soul. Living in a fairly large house in a rural area meant that during holidays, James...

Letter from Jefferson City

by justincbenedict on Sep 16, 2017
BDSM

Dear Shoeblossom: Do you get many letters from Jeff City, or from Missouri at all? Harmon, my husband tells me we are the "silent majority" and no one cares about us, until the Presidential elections come around. Then we're considered the conservatives, I suppose. Harmon and I were at one of those Tea Party Town Hall events, and I remember reading an edito...

Jennifer's House

by subservient_husband on Sep 17, 2017
BDSM

I had woken about five and had plenty of time to prepare Jennifer's oatmeal as well as clean up the cooking dishes. Jennifer came down wearing a pencil skirt with a business jacket. She carried the folder from the night before with another piece of paper over it. She sat down to eat while I waited in the kitchen and said, "Come over here and kneel on the flo...

Milky Boy Ch. 05

by Subone1 on Sep 16, 2017
Toys & Masturbation

I drove home still in a warm afterglow from that excellent milking. I realized that there was something very appealing to my submissive side about being milked like that on my hands on knees. It brought a smile to my face as I pulled into my driveway. I walked into the house with my briefcase turned toward me so my wife didn't see the "got milk?" bumper stic...

Workplace Chastity Law

by MissKateKees on Sep 13, 2017
Fetish

This is set several years in the future from the 'Women in the Workplace' series. The FEM NOW party is in government and has passed a radical new workplace chastity law. ***** Jada knew she had landed on her feet with her first job. Fresh from graduation at Athena University, she had secured a well-paid and prestigious position within Osiris Investments; H...

Evil Slut Bride Ch. 02

by PeterOmez on Sep 12, 2017
Loving Wives

My mom was hesitant to let a new friend she didn't even know be a bridesmaid, but I finally convinced her, provided she could find another groomsman, too. She said she'd discuss that with Davey. So after talking with Mom, I asked Jenna if I could call Davey about it, and promised to keep licking her pussy during that phone call, too. Needless to say, she lov...

Pegging for Promotions

by TheDougler80 on Sep 18, 2017
Fetish

Doug was less than five years out of college, only in his late twenties and had already started one of the most successful businesses in his city. It seemed as though he had made every right decision since leaving school. That is, until he decided to hire a personal assistant. There were a number of qualified candidates, but when Melissa walked into his off...

The Moral Slavery Ammendment Ch. 06

by Vslave on Jun 1, 2020
BDSM

The camera man brought Ava Abrams to their manager's house, a small mansion in a quiet bedroom town only a twenty-minute commute out of the city. On the way Ava was given back her clothes which her colleague had picked up from the floor of the theater. She also opened her slave training kit which she received from a secretary on the way out of the courthouse...