Chastity Money Stories

91,234 results
Orientation
Length
Source
Infinite Scroll

Chastity Vacation

by _Ashley_ on Oct 9, 2017
BDSM

Stephanie Her long, tanned legs stretched over the side of her bed as she rubbed the sleep out of her eyes. She took a few uneasy steps as she headed for the curtains. She gasped as she slowly drew them, temporarily blinding her deep green eyes. The sun was still partly blocked by trees but that didn't stop it from fighting through and melting the light cov...

Creating a Monster

by justincbenedict on Sep 19, 2017
BDSM

2006 I wait on my knees, with the steel chastity tube locked between my legs, for Bootsie's return. How will she come back? Freshly fucked or with semen residue on her glossed lips? Have I made a mistake by relinquishing all control of my marriage? 2003 "Oh Silas, honey. That's the cutest thing I've ever seen!" Bootsie's enthusiasm was bubbly as she lock...

Made to Obey Ch. 11

by madetoobey on Aug 21, 2019
Transgender & Crossdressers

Reprise: I'd been caught wearing my Sister-in-law's underwear and jerking off to shemale porn by wife (Ruth), Sister-in-law (Esther) and their mother (Donna). I'd been forced into a chastity cage and made to wear panties all the time. Humiliation was now a frequent event. Esther, who had investigated my internet usage on my laptop to see if I'd visited shema...

The Office Boy Ch. 10

by Aussie Worm on Sep 25, 2017
BDSM

Three weeks had passed since Katrina and I got married. Our honeymoon went quick but we made the most of it. Everyday Katrina had me out of the chastity belt and made love with me, sometimes more. Although I wouldn't say it wasn't enjoyable to me, I just never had the opportunity to interact. The only time I could interact and pleasure her with at least my...

Platonic Chastity

by Cagedcompliance14 on Aug 24, 2020
BDSM

Platonic Chastity * Author's note: I wanted this story to be a bit slower and explore the real life implications of a femdom relationship on a man and woman. This first chapter is mainly setup for the remainder of the tale but I hope the reader enjoys it nonetheless. CH 01 Taylor sighed in frustration as he looked at his cell phone, he had overslept again...

Goddess, Sir and the Cuck Bitchtits

by slavebitchtits on Aug 18, 2017
Fetish

I think to myself all that I am leaving behind, my job, my wife, my friends and family. I have a rush of fear and trepidation, but then I consider that I will be gaining the opportunity to serve at the feet of the Divine Goddess Jessica and Sir. Will my life new life will be better? But then I remember that is inconsequential. The fact is that Goddess and Si...

Who Wanna Be a Bimbo? Ch. 06

by mattpantyhose on Jun 8, 2020
Celebrities & Fan Fiction

Joe Avarege was not the most handsome of men, he was rather... average. At 181 centimetres he was moderately tall, his face was relatively plain, but he kept it clean shaven and overall well groomed to be attractive to women. Joe was of average built and relatively slim, but had a little belly which are so common among modern men. His head was bald but decen...

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...

A Cruel Hand Job Queen!

by justincbenedict on Aug 6, 2019
BDSM

"I really like these diamond earrings. Two carats is impressive to this girl." "Callie, you've changed my life. And my parents like you. My mom just told me how she thinks 'Calypso St. Claire is a pretty name, and she's so classy." "I was christened Edna Mae Womack, and grew up in a double-wide, but I'll take it." "Oh God, you're making me almost spurt, C...

Letter from Newark

by justincbenedict on Jan 8, 2019
BDSM

Dear Shoeblossom, I am just an ex-cocktail waitress who married a troubled but worthwhile guy. Mom always told me to find someone classy like a dentist or a Buick dealer. "Mariah, it's as easy to fall in love with a rich guy as a broke guy." But I fell for Raymond Withers, Jr. hard, and I married him right before he went to Vietnam. Still, as in all marria...