Chastity Boy Stories

108,647 results
Orientation
Length
Source
Infinite Scroll

Letter from Des Moines

by justincbenedict on Sep 24, 2019
BDSM

Dear Shoeblossom My first husband was an asphalt salesman; he sold cork flooring, too. I locked him in a plastic belt soon after we met; that much time on the road can make a man quite frisky. And of course you know the type. Ralph "Rip" Muztagh was a flirt from the word go. And he had what you'd call a long "cunt collar" amongst his friends. One of his...

Letter from Coldstream Canyon

by justincbenedict on Sep 17, 2017
BDSM

Dear Shoeblossom: My cousin Glen is married to a dominant bitch called Jocelyn. When Glen and his brother Gavin, both free-wheeling, bimbo-chasing poker-playing drunkards met Jocelyn in a club, they had no idea that the icy blonde would tempt the two of them, and Glen's boss Monroe, into becoming her slave harem! Now Glen hasn't been out for a poker night...

Office Power Politics Ch. 07

by PaulHub on Nov 18, 2019
BDSM

They'd settled into somewhat of a rhythm after the conference. One month her team would perform best, the next month it'd be his. It was healthy competition and the board loved it. Their meetings had continued and increased in frequency, the legs on his desk had started to get a bit wobbly from all the action it was seeing. But as long as numbers were high n...

Innocence Lost Ch. 18

by bradley_stoke on Sep 14, 2017
Novels and Novellas

In Which Purity is reconciled with Innocence; Purity is separated from Chastity; and Purity appreciates the value of Twelve, but is displeased by the association with Chastity. Purity hadn't seen Innocence for such a long time, and she was very pleased when she heard that she and her sister had left Wonderground. She'd never cared to visit a place with suc...

Good Morning

by Gonegirl611 on Sep 16, 2017
BDSM

When Ben awoke, he couldn't breathe and he couldn't move. Then he smelled her and felt her warm pussy on his lips. Now he remembered where he was. He was tied to the guest bed in the house that belonged to his Mistress. It was still dark, but he couldn't tell if it was just another middle of the night call (her insomnia woke her up frequently) or if it was...

The Sexy Cuckold Couple Pt. 08

by cuckcpl4play on Sep 19, 2017
Fetish

As I drove home from work, I could not stop thinking about how our lives as slave and slut had escalated so quickly. What felt like days ago, I was a powerful executive about to obtain my new and even more respected position, but instead I was driving home soaked in my colleagues urine as the new office demoralized submissive. My wife, who was the love of...

Business Trip - Day 01

by pantywriter on Dec 16, 2019
Transgender & Crossdressers

Day 1 At four-thirty in the morning, when you and your girlfriend are both up and screaming at each other to find this and that, because you both have flights leaving the airport within ten minutes of each other, and within ten minutes from six, sex is the very last thing on your mind. We woke on time and were generally getting along well but Emma was havin...

Letter from Mount Chapel

by justincbenedict on Aug 20, 2018
BDSM

Dear Shoeblossom, I got into the sweetest deal. I agreed to play femdom games with my geeky male roommate. He owns the house and was renting me one of the rooms, and like so many nerds, he has the hots for us tattooed, embroidered jeans types, I guess. Oscar is the sweetest guy, you know the kind. Comes to try and ask you out when you're smoking in the sch...

Enslaved by Marilyn Ch. 05

by Philnominal on Sep 26, 2017
BDSM

I never expected this. Yes I knew that Marilyn was Boss. She controlled me and whatever she demanded I did. That was law. However, I had never thought of being locked in chastity. She was letting me know who's dick it was and it clearly wasn't mine! "You will spend the next week like this. I am going to control every once of your desire and your very being...

Pro Domme Assignment Pt. 02

by Dprboy4Dominant on May 7, 2019
BDSM

I was shocked and embarrassed and immediately put in headspace from her direct words. Embarrassed not only by my very full diaper but that I had been caught disobeying a direct order. Head Mistress S walked over to me as I hurried to get back on my knees. She was dressed in a very beautiful business suit. She came very close to me, wrapped her hand around my...