Chastity Cage Milking Stories

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Length
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Infinite Scroll

Locked Away

by johnlocke1123 on Sep 17, 2017
Fetish

I don't know whether I should have been surprised or terrified but when I finally presented my new, most-extreme-to-date, chastity plan to my wife she instantly agreed and insisted that we start right away. I should probably go into our background a bit to put things into perspective... My wife and I have been married for ten years and we have three great c...

Family Chastity Story Ch. 02

by antares34 on Jul 3, 2019
BDSM

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+. ***** Having grown bored with how things were progressing with my sissy son, I have recently ventured into a new and fun project –filming and distribu...

Mommy's Caged Boy Toy

by milkydreaming51 on Sep 18, 2018
BDSM

This may be the best story I've ever written yet. Please comment and rate. I want to know what was good about it and what I can improve. Thank you now enjoy! ***** It's been 4 months since I fell in love with my new domme, Miesha. I was at the time a horny, broke, 18 year old college student and she was a 41 year old divorced woman with no kids. We natural...

Crossdresser's First Anal Orgasm

by ksha on Sep 16, 2017
Anal

A young man still experimenting with his body, found a new fetish he enjoyed quite a lot. He found the joys of anal masturbation. He had heard rumours of an orgasm so wonderful it would leave you shaking afterwards. He was in search of his very first prostate orgasm. This is the story of the first time this young man would discover the joys of prostate pleas...

How I Became a Chastized Cuckold Ch. 04

by gizzard on Sep 19, 2017
Loving Wives

**Warning** This fantasy story series contains or will contain elements of Male Chastity, Orgasm Denial, Female Domination, Cuckolding, Interracial Sex, Bi-sexual Innuendo and Tendencies, Teasing, and BDSM Activities. If any of these topics are offensive you to, I recommend not reading. * It was a few days before she allowed me to use the rubber black cock...

Mistress Katie Supervises Ch. 03

by royalrogue on Sep 18, 2017
Fetish

Michael was mowing the lawn when she called. Slowly he had been crossing the small lawn, pushing the mower at comfortable pace chosen to avoid sweating too much in the warm summer afternoon heat. The quiet mower whirred, clipping the few grass blades that had grown tall enough to reach its rotating blades. Luckily, the mower did not prevent him from hearing...

My First Milking

by Bakeboss on Sep 13, 2017
Fetish

When Mistress first put me into chastity, she said it was for a trail period. She soon found out it not only keeps me from abusing my worm while she is out it also keeps me more attentive to her needs. Another plus was that now I had to sit to pee, I have always had to relieve myself this way while Mistress was around, but she suspected when she was away I d...

Mommy's Gentlest Touch

by milkydreaming51 on Oct 30, 2018
Erotic Couplings

I make my way exhaustedly into the house. It's been a long day at college classes and things aren't getting much better for me below the belt. I stumble into the living room, dropping my bag as I do, and kicking my shoes off. That's when I see a woman waiting on the couch with her legs crossed staring directly at me. She's Columbian, average height, not sk...

The Pump House

by AlinaX on May 11, 2020
Fetish

Inspired by an idea by enigma3 in the Forum. * They say size doesn't matter, but when you are - whether by length or girth - within the smallest five percent of the population, it's difficult not to feel self-conscious about it. It's difficult to talk to women without imagining their horror, their amusement, their mockery, their contempt. Easier to avoid r...

WhiteBoy FuckToy for Ebony femdom

by flawlessgsmkt on Sep 12, 2017
BDSM

It's dark. I'm kneeling in a locked wardrobe. My hands are cuffed behind my back and secured to a ring in the wall. I pull at them a little where the cuffs are squeezed against my wrists. Not that there's any point. On previous occasions I've struggled against these cuffs in a desperate fury to escape. They held when I was trying my hardest to break free. Th...