Chastity Milking Stories

28,642 results
Orientation
Length
Source
Infinite Scroll

Blue Balls

by Renaissanceangel on May 12, 2020
BDSM

My husband's blue balls are progressing nicely. I haven't permitted him to ejaculate for 41 days now, since we switched roles, making me the dominant and him the slave. His testicles are distended with their load, hanging heavy and hard in my hand. I give them another hard squeeze for a few seconds, eliciting a moan from the man to whom they are attached....

A Slave Trainer Ch. 01

by HisSexKitten0908 on Sep 26, 2017
BDSM

"Hurry, the new shipment will be here soon." I say indifferently. Amber, my dark haired beauty, kneels in front of me. She unzips my jeans with her teeth and licks up the side of my cock, sending shivers of pleasure through me. She sucks the bulbous head into her mouth, burying her face in my crotch. I groan as my dick hits the back of her throat. She sucks...

Chastity with Ex as Keyholder Ch. 03

by chastity_sissy on Mar 12, 2019
Fetish

Back at my apartment, I wanted nothing more than to just get the chastity device off of me, but I still couldn't help but be aroused at my humiliating situation. Here I was, chastised by my previous girlfriend who now controlled not only my orgasms, but whether I could have sex with another woman. Suddenly, my phone buzzed, notifying me of a new text messa...

The Versatile Student Ch. 02

by atlanticsexual on Sep 16, 2017
Fetish

Dave awoke with a start. Something seemed somehow different. His hand was drawn to his penis and there he felt it. ... At breakfast, Denise smiled at him. I'm really pleased with you Dave. You look so nice in your undershirt and boxer briefs, eating your breakfast, drinking your coffee. Richard left early for work, its just you and I. Denise, why the cha...

The Set Up Pt. 02

by undermythumb10 on Sep 15, 2017
Fetish

This is the continued story of my life as a sissy and is a continuation from part 1 The Set Up. ***** As I mentioned I am sat tied to a chair with my stepdaughters panties placed so the crutch is over my nose, it's a long story which started when I met and married my wife now Mistress some six months ago. I am now a total submissive sissy cum slut for my...

A Wedding in Cathedral Heights

by justincbenedict on Sep 17, 2017
BDSM

-Book One Giles stepped into the vestibule, blushing. Keri smiled. She enjoyed Giles, he was a real gentleman, excellent manners, generous tipper...but despite the fact Giles was three times Keri's age, whenever he came to visit, he was like a bashful thirteen year old.He had none of the manipulative guile that Gerry, Keri's fiancee had. In her struggles...

Her Male Wife

by Zippeduptight on Nov 6, 2018
Transgender & Crossdressers

Sometimes I wonder how I got into this mess. The answer is obvious but it usually comes during the day when I pee. Carla's orders are to sit when I pee. I lift up my skirt, and tuck the exposed chastity device down, and relieve myself. Just like now. The shiny pink pvc sissy maid outfit she bought for me is locked on at the neck. I stand up and flush walking...

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...

Donna's Ultra-High Heels Bk. 02 Ch. 11

by SHAFERLINE on Sep 15, 2017
Fetish

Author's Note 'Donna's Ultra-High Heels, Book 2' is a continuation of Book 1 and can be read without reading the first book, although it is highly recommend that Book 1 be read first since it would be helpful in understanding the character development of the main players. I tried to make the transition to Book 2 as seamless as possible by briefly summarizi...

My Old Guy Ch. 02

by anonentity on Sep 17, 2017
Mature

Chapter 02 Tasty Tasha tells all! "Dear Mister Old Guy, WOW! All I can say is WHEW!! I keep on looking at that picture you took of me straddling your legs with your cock in my hand aimed at my craving cunt! Not that I will ever forget that moment but I'm sending this letter to you so you will never forget it either. Well like I said in my first letter t...