Chastity Boy Stories

108,647 results
Orientation
Length
Source
Infinite Scroll

The Perfect Man Ch. 02

by Freakboy80 on Sep 18, 2017
BDSM

Please read the "Perfect Man" before reading this. This story is a continuation of that story. * It had been a week since Justin had seen Sandra. He talked to her on the phone everyday, but she had refused to see him until another week had passed. When he would ask to see her she would always remind him of what she had told him the last time they saw each...

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...

Chastity Morning Ch. 02

by jonhawks on Sep 15, 2017
BDSM

Morning wood wakes me at 5:30 yet again. I could almost set my watch by it. I momentarily have images of my cock imitating a green superhero undergoing massive body growth and ripping through clothing and anything that attempts to contain him with a roar of power. But alas, my cock possesses no super-human powers. The cock cage is my kryptonite and it keeps...

Innocence Lost Ch. 30

by bradley_stoke on Sep 14, 2017
Novels and Novellas

In Which Kedi rediscovers Innocence by choice, Chastity by circumstances, and meets Honore who is herself reunited with Innocence. Kedi knew that Innocence was soon due to arrive to spend a few days with her, but she wasn't exactly sure when she'd arrive. She had been quite surprised to hear from her, although they'd kept in touch all the months since they'...

The Choice

by whispy_sub on Sep 17, 2017
BDSM

Christina smiled as she leaned back in her recliner. The patent leather of her bodysuit rasped as she crossed one of her legs over the other. With her eyes closed, she sucked in a deep, satisfying breath. Then her eyes fluttered open, and focused on a nude, kneeling man in the corner. "Tell me again why you are here boy." The young man shifted his weight fr...

She Sensed I was Submissive Ch. 03

by eatmebeatmeguy on Sep 24, 2018
Fetish

I couldn't believe what I was seeing. She was naked in front of her webcam, rubbing her pussy while 10 guys were stroking their dicks for her. All ten cocks were across her screen like a security guard watching surveillance cameras. I was restrained and had a big dildo in my mouth, so I couldn't move or say a word. "Ok, we are going to play a game. The f...

A Sissy is Born Ch. 02

by gtanya on Oct 13, 2020
Transgender & Crossdressers

Author's note: This story is the second chapter of "A sissy is born" series. Please note that it is a very slow build up and if you are looking for some hardcore sex right away, it is not for you. Please leave your comments to help me improve. It was a fairly uncomfortable couple of hours of the train ride with the constant staring of Mr. King. His gaze som...

The Contest

by justincbenedict on Sep 13, 2017
BDSM

Benny Price looked a bit discomfited as he entered the Marathon room. There were four guys, kneeling on pillows... Yes, naked as the day they were born, jerking their dicks VEERY slowly. They looked exhausted, and Benny looked at Nora, his beautiful fiancée, and wondered what the hell he was doing here. "You were so busy with work, you've missed the la...

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...

Family Chastity Story Ch. 02

by antares34 on Jul 3, 2019
BDSM

This is a work of fiction. The events described here are imaginary; the settings and characters are fictitious and are not intended to represent specific places or living persons. All characters are age 19+. ***** Having grown bored with how things were progressing with my sissy son, I have recently ventured into a new and fun project –filming and distribu...