Chastity Boy Stories

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Mistress Sharon’s Control Challenge

by CaptainSwitch on Jul 6, 2020
BDSM

My wife challenged me to a contest. She would give me a hand job and I would try to keep from cumming for five minutes. If I could maintain control for five minutes, l would get to fuck her anytime I wanted during the upcoming weekend. If I got too close to orgasm, I had to let her know and "give up" before cumming. If I "gave up" for losing control and gett...

Mind Games

by CaptainSwitch on Aug 6, 2019
BDSM

My husband and I have been married over 25 years. He loves to play dominant/submissive games, so for his birthday this year I decided to fuck with his head. I would never be unfaithful and I have no desire for other men but I could make him think otherwise as part of the game. To start I told him to strip, lock the chastity on, put on the wrist and ankle c...

An Obsession

by Marcus_Cicero on Jul 30, 2019
Transgender & Crossdressers

It would have been after that documentary. The one with a feature on online dominance-submission relationships on Fetlife. Because before that moment in time life had been so vanilla. Marcus had been queer and had had a boyfriend or two... or three since turning 18. Well, hell, he'd been to the bathhouses since turning 20. He'd even gone as far as to create...

Luke Powers: Black Master Pt. 03

by scatwoman on Sep 16, 2017
Interracial Love

Brad's Ruined Honeymoon Starring: Brad Whitebread, Chastity Belle, Wesley Whitebread, Luke Powers and a special guest appearance by Mishi herself! (See the "XXX-Women" series, "Misadventures of Mishi" series and "The Perils of Greggie-Poo" for more Luke Powers & Mishi action!) Directed by Mishi. Most of you are familiar with Mishi favorite boytoy porno...

Feminizing First Step Ch. 03

by antares34 on Oct 21, 2019
Transgender & Crossdressers

(All characters are age 18+) *** I felt like I was losing control. My body and mind were becoming less and less masculine with every passing day. And I was secretly ENJOYING it. I couldn't help myself. Every time I looked in the mirror, I found myself loving the ever-changing reflection. First, my dyed pixie haircut. Then, my bikinis. Then, my nose, ear, a...

The Dominatrix Order Pt. 01 Ch. 02-03

by Jwwsmith on Dec 11, 2018
BDSM

Isabella locked Slave 138 back into his chastity device and gave Nadia the key to it. Like all of the chastity devices used in Femininus, it was a three ring design chastity cage made of steel with a bronze lock. Once Slave 138 was secured in his chastity cage, Isabella then ordered him to escort Nadia to her new living quarters. Nadia and Slave 138 arrive...

Katie and Willie Pt. 03

by WillieTurner on Feb 19, 2018
BDSM

The rest of the month flew by! Katie took my approval for her to be more demanding of me, sexually, to heart; and she developed new and better ways to tease me to the point where I was in a constant state of arousal and obedience. I was amazed at how strongly my unfulfilled arousal was linked to my increased docility, and my desire to please her. She bought...

Caged Pt. 01

by ToferSixoErotica on Feb 6, 2018
BDSM

James sat naked on the side of the bed. He blushed, unable to stop himself from having an erection. Elle sat between his legs, smiling. "You know, I'm never going to be able to get this thing on, if you can't control yourself" she told him, holding a small, plastic chastity cage in her hand. James had bought the cage a while ago, but had never had someone...

Collecting Catholics: Chastity

by Sosela on Sep 12, 2017
NonHuman

"You have to come see this!" Catherine giggled conspiratorially, looking left and right to make sure no teachers or nuns were around. Mt. St. Vesper Ladies Finishing School was quite strict, and the staff tended to spy on their students even though they were of legal age. It was a catholic college in all but name, and even though the Dean said that student...

A Virgin released from Chastity

by ronron1818 on Nov 16, 2020
Fetish

It was time to move on... I will be graduating today, 4 years after moving in with Ruth, and tomorrow, I will be moving out to start my life as a grown up. I already found a job in my home town, and rented a small apartment near the new office place. Ruth came with me and my parents to the graduation event. My parents liked her a lot. For them, it was lik...