Chastity Boyfriend Stories

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Letter from Eisengrim Township

by justincbenedict on Sep 17, 2017
BDSM

Dear Shoeblossom: Sometimes Brearley lets me jerk off. Kneeling on the hardwood floor on my bare knees, rubbing my stiff and long denied cock, it's so painful! Brearley is always gorgeous, fully clothed as a striking contrast to my nakedness, in tight jeans or a sexy miniskirt, sometimes a tube top. Often she will wear a sexy business office outfit, which r...

My Sissy Cuckold Life

by SissyCuckMike on Jan 2, 2021
Fetish

Hello everyone, my name is Mike and i am now a sissy cuckold. If you don't know what a sissy or a cuckold is i will explain, a sissy is like a cross-dresser but usually dresses up in pink frilly women's clothing and cuckolding is similar to a hotwifing where she goes out on dates and fucks other men without her husband/boyfriend around but with cuckolding it...

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Soames's Submissives: The Game

by justincbenedict on Sep 17, 2017
BDSM

Calvin knelt, naked on the Consequences square of the game... Looking at the sexy girl in the cheerleader outfit, and her muscular companion, both of them in their early twenties, but otherwise looking very much like the kids who awed Cal in high school. Cal had told Soames (in confidence) that once, a girl had asked him to the movies, one he'd had in his...

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...

The Keyholder Ch. 16

by AndreaJordan on Mar 31, 2020
BDSM

Ben had been in chastity for several years and always under Amy's control. Her fantasies and sexual urges had long since dictated his life. She was currently going through a phase of chaining his chastity cage to things. Often immoveable objects that left him continually aroused yet totally stuck and dependent on her. "Amy, Sweetie?" Ben called again. Com...

The Locksmith

by Vashtar on Feb 12, 2019
BDSM

Life as a 24hr Emergency locksmith is often boring, and mainly consists of getting drunks back into their flats, or securing properties that have been broken into. But occasionally something different comes along to liven up the day. On mid-week morning a few weeks back, I got a call from a woman who was having problems with a padlock. It was a little bit o...

Furthering My Education

by jimmysub on Sep 15, 2017
Fetish

Well I had to go back to Community College to take some child development courses as my wife and her lover are planning on having a child together. This is part one of the adventure. I really don't like this idea but what my wife says go. Her biological clock is ticking and she has been with the same lover, Mr. Steve for about 3 years. So Debbie is going to...

The Office Boy Ch. 06

by Aussie Worm on Sep 25, 2017
BDSM

Jenny stood naked in the centre of the dungeon, her wrists restrained to the ceiling forcing her to stretch and place all her weight on her toes. Her plastic chastity belt and bra that she had worn for past month had been removed and it wouldn't be needed again. Jenny's eyes were also taped shut and a blind fold placed over that so she couldn't see a thing....

The Manipulatrix Ch. 02

by PeterOmez on Aug 30, 2017
Fetish

Over the next few days, at different times, I had Zoe, and Katrina, and Mandy over to my place, and we picked out all kinds of sexy outfits online, to buy with my boyfriend's credit cards. As I mentioned before, I tried hard to keep his debt up, so when he got his statements, he could see all my charges, and the painful memories of all the money his ex-wife...

I Don't Know How To Dominate

by Susan Strict on Sep 13, 2017
BDSM

"I really don't know how to do it," she told him. "It's just not me." "If it's what your boyfriend wants," he suggested, "Then I don't see you really have a problem with it. After all, it's not difficult, is it? "I wouldn't know how to start," she confessed. "Can't you give me some advice? I mean, I've heard all about the dominatrix thing, I just don't rea...