Chastity Boy Stories

108,647 results
Orientation
Length
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Infinite Scroll

Valentina of the Colfax Inn

by justincbenedict on Feb 25, 2019
BDSM

SUPERBOWL SUNDAY AT THE COLFAX INN Valentina was toying with her husband's scrotum. Normally Val wore snug but dignified cashmere sweaters, but today she was clad in a belly tee shirt and what the longshoremen at Buttermilk Pier referred to as "whore shorts". Nibs, Val's loyal and faithful husband was bound to the narrow coffee table in his back office. Hi...

Letter from Friardale Lane

by justincbenedict on Sep 24, 2019
BDSM

Dear Shoeblossom, I love my fiancée, Harmony Harrow, but the engagement has caused me quite a bit of stress. We have played in the BDSM scene a bit, so I didn't object that much when she put me in a chastity cage. I thought it was just for the weekend, but she seems to have left it on, and her excuses haven't really comforted me. "Harmony, I get it, you w...

Master's Femboy Maid

by KittyAshleyy on Apr 14, 2020
Transgender & Crossdressers

Ocean blue eyes looked back at me as I looked myself over in the mirror. My Master was hosting a get together of his like minded friends and had told me to dress in my best maid uniform. That was a black maid dress with a skirt that barely covered my ass, white gloves which reached past my elbows, a small white apron and fishnet stockings with a black garter...

The Perfect Man

by Freakboy80 on Sep 18, 2017
BDSM

Sandra was tossing and turning in bed, trying hard to fall asleep and suppress her thoughts of sexual desires, but she just couldn't stop thinking about it. She could feel her panties becoming moist as she fantasized about the things she wanted to do to an unsuspecting male. Sandra has always been a dominant person, and always had to be in-control of any sit...

Obedience Training

by justincbenedict on Sep 17, 2017
BDSM

"How was Dubai?" asked Benny Price, as Nora made herself comfortable in his living room. Nora grinned. She'd been dating Benny for three months, ever since she'd met him at a singles mixer for dominant women and submissive men at the PainCafe. After their initial dates, Nora had put Benny in a chastity device. She pointed out to him that if he really liked...

Letter from Grimalkin Canals

by justincbenedict on Nov 11, 2019
BDSM

Dear Shoeblossom I am a partner at Prescott & Briggs, and I suppose I should be looked up to, but most of the men employed under me, from junior brokers to mail clerks and elevator operators laugh at me behind my back. I have a "hotwife" as they say in BDSM and cuckold literature; and she demands that I find her attractive young men (loves, LOVES blacks an...

Chastity of a Cheating Man

by crazythoughts on Sep 17, 2017
BDSM

He didn't know it quite yet but she had found his hidden messages on skype, email, facebook and even had seen his deleted messages on his phone. She then started to check phone records and saw that he had been talking to numerous women while they were dating and even as soon as the last week. She started to count up the time and noticed that it equaled many...

Online Goddess Ch. 01

by subboy129 on Sep 17, 2017
Fetish

It all started online... I was seeking a domme to serve and after having terrible luck, I found exactly what I was looking for. A Goddess that I could worship and that would treat me like garbage. We started by having chats, she seemed very nice at first, asking me my limitations and what my likes and dislikes were. She started getting my trust and I start...

The Dominatrix Order Pt. 04 Ch. 02

by Jwwsmith on Apr 9, 2019
Fetish

Sissy Slut was the only one of Isabella's slaves who had not yet fallen ill. And as such, Sissy Slut was the only slave in healthy enough condition for Isabella to play with. He enjoyed receiving so much of her attention, and she teased and tormented her tease and denial slut unrelentingly. Twenty five days before the next supply of Medication 42 was due to...

Transgender Avis's Incredible Power

by justincbenedict on Jul 4, 2018
Transsexuals & Crossdressers

Skokie, Illinois, 2009 Aiken Aycock was sad to be losing her brother Aiden to the operation. He was a great guy, but he gave Aiken the beatings and torture she needed. But he'd finally gotten the money to do the big change. Aiken had really enjoyed supporting Aiden, letting him live in her apartment...stripping naked when she got home, and taking a few fro...