Chastity Boy Stories

108,647 results
Orientation
Length
Source
Infinite Scroll

Marissa

by RoxyReynolds on Jul 27, 2020
BDSM

Marissa's morning. Marissa was drawn out of sleep by the aroma of fresh coffee. The bedroom was still in darkness, no curtains opened yet to reveal the start of the day. Her coffee was placed gently on her bedside table. 'Good morning Mistress,' said Richard. 'Good morning.' Marissa rolled from her side and onto her back, she pulled back the duvet, reveal...

Milky Boy Ch. 06

by Subone1 on Sep 16, 2017
Toys & Masturbation

They left me alone the rest of that day and also that night. I drove to work the next day (Wednesday) with the chastity device in place, happy that my wife hadn't noticed it yet. Of course, the way our sex life had been going lately, she may not notice it for a while! When I walked in, my secretary was already at her desk. "Good morning, got milk?" she said...

One Pump Chump

by Gaius8666 on Sep 12, 2017
BDSM

Desiree was stunningly beautiful. The several strip clubs she owned, and occasionally performed in, were wildly successful and major generators of cash to her ever growing bank accounts. Owning such a profitable venture, and running it with the efficiency of the sharpest mind on wall street had made her incredibly comfortable very early in life. Having gro...

Lascivious Lecture Hall

by justincbenedict on Mar 17, 2020
BDSM

"To answer your question" Tye said with a smile to the audience member, "During the sixteen months before we wed, I allowed Norvil eight orgasms, and then in the last four years and two months, he's had, I think, twelve?" Typhoon looked over at Norvil with an inquiring smile, and he nodded, embarrassed. "But you say on your blog that Norvil's allowed one e...

Lady Connie Ch. 01

by Snowkemper on Sep 25, 2017
BDSM

Author's note-I've submitted two series of stories to this site, and both have been dark, violent and frankly pretty unpleasant. I wanted to write a BDSM story with people that were happy, content with their roles and getting what they wanted. This is the result. Feedback, votes and comments are always greatly appreciated-even negatives! ***** JIM closed h...

The Sexy Cuckold Couple Pt. 10

by cuckcpl4play on Sep 19, 2017
Fetish

After the crazy collaring weekend, our home life shifted slightly back to some form of normalcy. Master would send us occasional texts, orders, etc., but overall there was nothing significant that was transpiring and in fact Miss Jenny seemed sad that more activity was not taking place. At work it was a bit of a different story...Master was his typical domin...

Letter from New Piedmont

by justincbenedict on Feb 7, 2018
BDSM

Dear Shoeblossom, I can still remember Rebecca's first comment: "You sure you want to do this, kid?" A full-figured ash blonde with brightly glossed lips...pure Jersey girl. "You really want to move in with me...the sessions aren't enough?" Sometimes the sessions were way too much, but I was lost without Mistress Rebecca. 46 to my twenty-three, she'd bee...

Steel Heaven

by LockedDarius on Sep 11, 2017
BDSM

I stood in the shower, allowing the hot water to caress my body in an attempt to wake myself up. The thought of another long day at work wasn't helping the situation, but at least it was Friday. "Get through today and enjoy the weekend," I thought. I stepped out of the shower and immediately realized I had forgotten to bring a towel into the bathroom from t...

Mommy's Caged Boy Toy

by milkydreaming51 on Sep 18, 2018
BDSM

This may be the best story I've ever written yet. Please comment and rate. I want to know what was good about it and what I can improve. Thank you now enjoy! ***** It's been 4 months since I fell in love with my new domme, Miesha. I was at the time a horny, broke, 18 year old college student and she was a 41 year old divorced woman with no kids. We natural...

Belted, Branded, Subjugated

by BurningSilk on Feb 12, 2019
BDSM

As a modern woman and slave owner, I take my responsibilities seriously. I treat my slave well and never subject him to unnecessary punishment or abuse. All I require from him is total submission and obedience. When I first met the man I would enslave, I made it clear that the first requirement for any relationship between us was his agreement to being kept...