Chastity Money Stories

91,234 results
Orientation
Length
Source
Infinite Scroll

Letter From Tacoma

by justincbenedict on Sep 17, 2017
BDSM

Dear Shoeblossom: When my husband, who is owner and ringmaster of the Epic Circus, comes into our hotel room (We, thankfully, don't have to live in the circus trailers) I'm ready for him. He lays the whip down, and then it's my turn... "Strip it all off Apollo, my love! Now you'll get a nice thrashing....it's MY turn to use the whip!" Sometimes after th...

Spalding and The Cheerleader

by justincbenedict on Sep 17, 2017
BDSM

22 year old Spalding Tyll walked home disconsolately, his knapsack hanging off his arm. It had now been 103 days since Mother had allowed him to masturbate, and it was hanging heavy on his young balls. Mother was mad at Spalding... She was going to punish him through humiliation by making him jerk off in front of the hottest cheerleader at Buttermilk Fall...

2035 - The Year of Male Chastity Pt. 01

by Longjohnsilver30 on Sep 14, 2017
Sci-Fi & Fantasy

It was all Max Andres fault. Married to Penny Durst, they were one of Hollywood's biggest A List couples. Cheating on such a gorgeous woman as Penny looked insane but Max's stupid decision would have far reaching consequences for most of mankind. Max publicly begged for Penny's forgiveness and after a month of pleading he was finally allowed return to their...

Family Business

by fantaseeboy on Jul 27, 2020
Fetish

Editor's note: this story contains scenes of incest or incest content. ***** Laying on my bed in my room in my mom's trailer, my laptop was set on the table beside me with my webcam aimed where I lay. White, satin, bikini panties were looped around my left ankle. The snug-fitting, stretchy crop top clung to my narrow, smooth chest and left my midriff bare....

Financially Dominated and Cuckolded

by johan26 on Sep 12, 2017
Fetish

This is a story about a woman cuckolding a man and taking all his money - don't read if that doesn't interest you! ***** I first met Kristin on a Saturday night at a trendy bar in my city. She was cute, around 28 with dirty blonde hair, and a sexy blue dress on. I'm 33. We hit it off and I bought her several drinks throughout the night. I thought I might b...

Letter from Sherier Place

by justincbenedict on Sep 17, 2017
BDSM

Dear Shoeblossom: I am a member and Substitute Treasurer of the Keeplock Club, a select group of women who keep their husbands and significant others in chastity belts. Our oldest member is seventy-eight, the youngest, a college junior. It's a constant vigilance, and I thought you might find it interesting, as your column discusses much of this. On Wednesd...

Cuckquean Chastity Wedding Vows

by Revanto on Sep 14, 2020
Audio

* * * * * Click Here to listen: .mp3 format or .ogg format. (8 min/mp3) * * * * * You walk down the aisle with slow, deliberate strides. You aren't just trying to be ceremonial. You can only take small steps. Underneath your beautiful wedding gown, steel thigh cuffs are linked by a short chain. You cannot spread your legs and you can only take dainty st...

Letter from Toledo

by justincbenedict on Sep 13, 2017
BDSM

Dear Shoeblossom: I really enjoyed "Letter from Los Angeles: Ms. Scunthorpe's Rebuttal" and also the story from the Time-Lock computer Mistress in "Letter from Greater Ponsonby ." I also have a paid key holder, Phyllis. I grew up in a strict Evangelical family, here in Ohio, and our parents were very primitive, sexually... Masturbation and copulation wer...

Evil Slut Bride Ch. 09

by PeterOmez on Sep 18, 2017
Loving Wives

Even though it did turn me on to think of my hubby walking AN HOUR to get to work, it was also a little inconvenient for me at times. If I wanted him to be home earlier on some day, I'd give him bus fare for that day, or I might just go ahead and drive him to work, and pick him up when he got off. I didn't drive him to work just because it was a nasty day, t...

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'...