Chastity Boy Stories

108,647 results
Orientation
Length
Source
Infinite Scroll

The Chastity Cube

by justincbenedict on Sep 17, 2017
BDSM

F.X. Copeland came to the Deliosse's front door, lugging the massive box, and pressed the doorbell. A moment later, Santiva Deliosse answered. "Oh, good, Cope, you're here. That's the Zero-Wave?" Cope nodded. "Yep, Miz Deliosse. Works like a microwave, but in reverse. It's an innerustin' invention of mine." Cope lugged the box into the house. It was a big b...

Dominant Housekeeper

by justincbenedict on Sep 12, 2017
BDSM

The new housekeeper, Miss Spargrove landed the thick wooden Spencer paddle for the fiftieth time on Shawn Cirrito's reddened buttocks, and Shawn bit her tongue to keep from screaming. As the paddle, built with holes throughout to make swinging easier and more painful landed again on Shawn's ass, she wondered what Ross was doing. Miss Spargrove had had hi...

Family Chastity Story Ch. 04

by antares34 on Aug 13, 2019
Fetish

Editor's note: this story contains scenes of incest or incest content. ***** 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+. ***** My girlfriend Christina has been staying with me for the past sev...

Laura Love Ch. 07

by Long2bLocked on Jun 26, 2019
BDSM

Note to readers: This series is a continuation of "Laura's Femdom Empowerment". You should read that series before this one. ***** Chapter 7 Female Led Destiny The next day was Monday. I couldn't wait to see Bodhi at work. I took one of his chastity keys out of the safe in my bedroom closet. I put it on the same silver necklace I was wearing in his domina...

Visions in Buttermilk Falls

by justincbenedict on Sep 13, 2017
BDSM

After Fanchon and her graduate student friend, Morse got in the house; Fanchon quickly went and switched on the computer web cam. "What do you think of this, Morse?" Fanchon asked. "This is my Wink's Wanking Web cam! Every night between nine and twelve my friend Theodosius Winkleburger masturbates for three hours in front of the camera, and I get to watch hi...

My Husband a Pornstar Ch. 03

by gtanya on Mar 20, 2018
Transsexuals & Crossdressers

Please read the previous two stories to fully understand and enjoy this chapter. If you don't want to read them, here is a brief description of what has happened till now: *** My husband was conned by me into exploring his sexuality and he finds out that he is bisexual. He also agrees on being a porn-star to earn a hell lot of money for us. After shooting...

Madam Veronica Ch. 02

by TalentedMistress on Sep 18, 2017
BDSM

Madam Veronica – David’s session begins. David looked up at Veronica briefly before dropping his eyes to the device in which his penis was now encased. His hands moved as if to touch, but a cough reminded him of where he was and in whose presence he was. And his fingers twitched but no more. As Veronica gazed upon him she could see his inner struggle… it wa...

Mistress Treva Wins Again

by justincbenedict on May 29, 2018
BDSM

Dr. Shepherdson Grangerford milled about at the fundraiser, his adoring wife, Treva by him, the ultimate arm candy even after all these years. A balding, chubby fellow came up, grabbing Shep's hand. "Dr. Grangerford, everyone is so pleased that you made the fundraiser, and that you'll be heading up the Ophthalmological Wing. We probably couldn't have gotten...

Becoming Friends Ch. 02

by mrbillcollecta on Sep 17, 2017
Loving Wives

"What time are we expecting Chastity over for drinks baby?" Stefan quizzed. "About 7 or so and she is bring the Margarita mix with her!" Kenya yelled from the bedroom. He replayed the events that unfolded before him in his own bedroom a few short hours ago. Seeing Chastity tugging and sucking on Kenya's huge 42DD tits was definitely the highlight of his da...

Jennifer in Chastity

by Wifetheif on Sep 14, 2017
Fetish

Some of Jennifer's friends had told their secret to affording college. They had found sugar daddies, older men who paid for their college tuition and expenses in exchange for sex. Amy, Jennifer's best friend was bedding a local banker and was doing very well indeed. Freed from the financial burden of massive debt from college loans, and with her sugar daddy'...