Chastity Bet Stories

70,817 results
Orientation
Length
Source
Infinite Scroll
SmutMD: The World's Biggest Erotic Literature Search Engine.
© 2025 SmutMD.com

Race to the Bottom

by jujou2006 on Nov 27, 2017
Fetish

The bump was totally unexpected. Jujou had been running round the track for some time and had fallen into that trance state so well known to the long distance runner. She hadn't even noticed that another runner had joined her on the track and when the contact came she lost her balance and spilled on the ground. "Watch out slow poke!" The taunting words dri...

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...

Lace and Love Ch. 03

by vaultdweller111 on Sep 19, 2017
Transsexuals & Crossdressers

Jake Orlov grabbed his duffle bag and rifle case out of the cab of his F-250. He had some other gear in the truck, but he decided to get the rest later. He was exhausted from driving back from Kentucky, training the Blackwell county sheriff's department's SWAT team for the past week. Jake was disgusted at how these guys managed to graduate the police academ...

Chastity Mansion Ch. 01

by Shavvy3100 on Sep 25, 2017
BDSM

Headache... It's cold in here... Am I lying on the floor? Bright light... Can't see a thing, everything is blurred... High heels clacking on the floor... Must be Eve... Did I pass out? "Eve, honey what happened?" "Ah, you finally woke up. Welcome to Chastity Mansion! How does the cage feel?" Am I awake? Can't be, I must still be dreaming. I'm in a room fu...

The Devil's Mystery Box

by bbcummings on Jan 30, 2019
Fantasy

Author's note: My idea is for the stories to mostly be 3rd person. However, this section basically has to be second person, so bear with me. *** The box you found was peculiar. Usually, a box didn't come with strange markings. It wasn't made out of exotic materials that seemed to defy normal physical behavior. Boxes were usually cardboard or wood. They held...

Open in Reader

A Slave's Journey Ch. 04 - Prospects

by punishedone on Dec 10, 2019
BDSM

So that the four of us have had some good times together and helped many others find what they needed and make their relationship stronger. With Susanne and Matt it is really simple Susanne works hard either at work, exercising, or trying to keep their marriage together by changing to Matt's needs. Matt on the other hand is unemployed, lazy, and is more abou...

Blowjob from a 69 Year Old

by HRDBNR69 on Oct 16, 2018
Mature

I travel a lot for work, and spend a good chunk of the year at hotels. I've had quite a few memorable encounters, but this is always one i think back upon. For background, i was at the time of the story 25 years old, i'm brown haired, with a short beard, 6'0 and 200 pounds. Work out a little bit, so was fairly fit, but no chiseled hunk either. One night i...

Sissy Girl Forever Pt. 01

by sissymissyct on Sep 18, 2017
Transsexuals & Crossdressers

The call from Mistress Andrea made my day. I hadn't seen her for over a week and was looking forward to playing with her & having my chastity finally removed. You should know that Mistress and I have known each other for many years and have I always enjoyed being her sissy sub. Lately she has been training me to be more feminine in appearance. I have been r...

Support Group Ch. 01: Chastity

by UndercoverInterracial on Sep 14, 2017
Interracial Love

Hi, everyone. This is my first time here; my first time doing this, so go easy on me, okay? I'm a little nervous. So, um, how do I begin? Well, my closest friend recently held something like an "intervention" for me. He showed me the path my life was taking and offered an alternative. I've never heard of a support group that requires an audition, but he sugg...

Teased by My Neighbor

by randomer555 on Sep 25, 2017
Fetish

I ate Beth to several more orgasms that night before going home at about one in the morning. It had been a long and frustrating night but I was also happy to finally have a keyholder. I managed to get about four hours of sleep that night. The chastity belt and my aroused state made sleeping difficult, to say the least. My alarm clock went off at eight, lik...