Chastity Milking Stories

28,642 results
Orientation
Length
Source
Infinite Scroll

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...

Loaned Out

by Valsslut on Sep 16, 2017
Fetish

Yesterday Lady Valerie loaned me out to her friend. Terrified beyond belief, I drove to a large hotel, rode the elevator up to a large suite and ordered to undo my pants and prove I was wearing panties at the door. I was scared about being scene in the hall worse the humiliation was turning me on so much my clit got hard. Lady Valerie had taken my chastity o...

Got Milk? Pt. 01

by macktosh on Mar 3, 2020
NonHuman

This story was written for the following prompt: "A young man works at a holstaur ranch, milking the breasts and cocks of the gorgeous and horny livestock that prefer the human touch over machines." (Note: Holstaurs are a kind of monster girl with horns and a propensity to produce milk, similar to cows.) This is quite different to my normal content, so ple...

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...

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...

Noble's Court 2.0

by entropy50607 on Aug 27, 2016
BDSM

VERY IMPORTANT, PLEASE READ: Please click "Start game" on the right side of the web page under the tab "Score" to fully experience the story. As, my story makes use of conditional statements and conditional chapters in its tracking of variables. For example, if your character arrives late to a particular event, specific characters may res...

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The Perfect Man Ch. 02

by Freakboy80 on Sep 18, 2017
BDSM

Please read the "Perfect Man" before reading this. This story is a continuation of that story. * It had been a week since Justin had seen Sandra. He talked to her on the phone everyday, but she had refused to see him until another week had passed. When he would ask to see her she would always remind him of what she had told him the last time they saw each...

Husband in Training Ch. 02

by Freakboy80 on Sep 15, 2017
BDSM

The next morning, before she left for work, she left a list of chores for him to complete before she got home. The list included doing the laundry and picking up the dry cleaning. "I expect these done when I get home from work!" She put at the bottom of the note. When she arrived home, she saw him sitting on the couch as usual, but this time he wasn't watch...

My Journey to Becoming a Mistress Ch. 02

by intofdom on Sep 17, 2017
BDSM

On the second anniversary of the day we met. He asked me for a large sum of money since I manage his dollars now. He told me it was a secret and I would definitely be surprised. I impatiently waited till that night. He arrived with a big bag. He sat next to me in bed and pulled out sluttiest dress that I had ever seen. He requested me to wear it. It was so...

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...