Chastity Belt Boy Stories

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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...

Letter from Augusta

by justincbenedict on Sep 17, 2017
BDSM

Dear Shoeblossom Deuce, my second son is finally beating me at Ping-Pong. The ball flies over my head! When I was a kid the balls were just white, but now they come in neon orange! Deuce looks relieved, I wonder why. Is it because I have always punished him, taking his pants down and spanking him hard with my paddle when I beat him at table tennis...what a...

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...

Slave Spalding

by justincbenedict on Sep 19, 2017
BDSM

One Spalding Tyll walked home disconsolately, his knapsack hanging off his arm. It had now been 103 days since Mother had allowed him to masturbate, and it was hanging heavy on his young balls. Spalding had asked his Mom to dominate him when he finished his first year of college, at age nineteen... Yes and she'd put him in chastity...although he'd had a p...

Slave Immigrant Ch. 22

by OldGuy1026 on Sep 14, 2017
Sci-Fi & Fantasy

After receiving a cloned body I immigrated 127 Light Years from Earth to Free Skyes. Unfortunately I had to work and pay for that cloned body and I had very few skills a high tech society could use. So it was either I become an Unskilled Labourer or a Sex Slave. I guess Human Recourses had me figured out correctly. All those years in BDSM chat-rooms and webs...

Spalding and The Cheerleader

by justincbenedict on Sep 17, 2017
BDSM

22 year old Spalding Tyll walked home disconsolately, his knapsack hanging off his arm. It had now been 103 days since Mother had allowed him to masturbate, and it was hanging heavy on his young balls. Mother was mad at Spalding... She was going to punish him through humiliation by making him jerk off in front of the hottest cheerleader at Buttermilk Fall...

Chastitymomma

by justincbenedict on Sep 14, 2017
BDSM

I've been having trouble with Charles again about the bedtime thing. Really, it's so silly. Eight o'clock is a sensible time to be under the covers, don't you think? "Mother I'm twenty-two and in graduate school!" he begs me. "It's bad enough that you won't let me go out at night, but couldn't I just sit up and watch Mad Men?" So I made a deal with Char...

Letter from Boston

by justincbenedict on Sep 17, 2017
BDSM

Dear Shoeblossom: I have read with interest your letters from chastity belt couples. I really thought I was an enthusiast, but now I think it may have gone too far. My love affair with chastity and denial began, I think, in my early twenties. In the summer after my junior year at Harvard, I wrecked Dad's BMW while drunk on the Montauk Highway, near our vaca...

Letter from Ravenswood Bluff

by justincbenedict on Sep 17, 2017
BDSM

Dear Shoeblossom: Brinker stands, a foot precariously on each chair with his hands behind his head, like an arrestee. I shake my auburn hair and wave my double D's at him, well displayed in the bikini top, blue with sailboats. "All I'm saying, Jessamyn, is that it wouldn't hurt to ask Shoeblossom. He's great about answering letters in my magazine, and he's...

Letter from Vines Village

by justincbenedict on Sep 17, 2017
BDSM

I drive a sterilized knitting needle through my son's left nipple. Sowell grimaces, but he is sucking on one of my bloody tampons, and his buttocks hurt from the vicious caning I gave him earlier. I surprise Sowell—when he's coming out of the tub, wet, naked and vulnerable, I charge in with my whippy cane and leave red, bloody streaks all over his slim whit...