Chastity Milking Stories

28,642 results
Orientation
Length
Source
Infinite Scroll

A Fantasy with Lisa

by chastityfan on Sep 13, 2017
Fetish

I met Lisa for the first time just after finishing a workout at the local gym. Over the next few weeks we ran into each other on a regular basis and ended up going to out for a few pints. Spending time together eventually put us in bed together and we decided out relationship was best left as a friends with benefits situation. Over time we discussed each oth...

Sissy Maid to Be... Ch. 01

by missjennymaid on Sep 5, 2018
Transsexuals & Crossdressers

Prolog I have always had the desire to dress like a girl. It started at a young age when my mother used to have me try on dresses to "see if they would fit my cousin." As I got older I still had the desire and it got strong enough that I started going out in public in college. I was lucky enough to meet and marry a woman who was accepting of my "hobby". Liz...

Dolores and Bill

by sweettalk4u on Apr 15, 2020
Erotic Couplings

It was Friday evening. Bill laid in bed waiting for Dolores. His aching blue steel hardon was almost painful. She would emerge from the bathroom momentarily to give him some relief, maybe. It was up to her. His cock had belonged to his wife for over a year now. Her control was 24/7. She might milk his cock tonight. She might not. He was hers, now and forev...

The Experimenting Fiance

by erogeek on Nov 11, 2020
Cheating Spouses

This is currently a work-in-progress. Updates to the ongoing story and paths, with reference dates, will be included here on the first page. Any questions/comments/compliments/insults are welcome via chapter comments and private messages, don't hesitate to reach out if you feel inclined! This story has multiple flags and variables that will influence how the...

Open in Reader

Cuckold's Descent

by syncbush on Mar 27, 2020
Cheating Spouses

Thank you to those of you who have liked or taken the time to comment/message me. I really appreciate the feedback. Feel free to add additional chapters, suggest ideas or leave comments. It is great to get ffedback and encourages writers to continue developing the stories. And special thanks to the Admins for making this story of the week! Really appreciated...

Open in Reader

Sorry Sissy You Lose Pt. 03

by LittleDickSissy on Feb 11, 2019
Fetish

"Mmmm that felt great" George said as she released his thick cock from her mouth. "Thank you". She looked up at him and smiled. She could still taste his cum in her mouth. She'd never had cum in her mouth before let alone swallow it! "Kiss it. Kiss my cock" George instructed her. She did as she was told, she puckered up and kissed the head of his cock a...

Tony's Ascent Into Cuckolding Ch. 03

by Cuckyboy3 on Sep 12, 2017
Loving Wives

She called Brad that evening to let him know that I had come around after some convincing. They chatted for a while, during which she told him about my misbehavior. She moved away from me and talked softly for a while from the other room. Finally, she came back to me. I heard her saying, "Do you promise? You'll do that for me?" Then she listened for a while...

Lait Maternal Pt. 04

by BaileySparrowtree on Sep 14, 2017
Fetish

Ashlee motioned Penny to take a seat at the table again. "Sit down, Penny. I am 'appy to learn you complied with our wishes. We can now proceed and make all of us very successful!" Penny smiled and chuckled, genuinely happy at Ashlee's excitement; her hands waving around creating big circles to illustrate their future successes. "Thank you, Ashlee. I am so...

Suzy Lets me Join in

by Bakeboss on Sep 1, 2017
Group Sex

The first big change in our marriage was when my wife convinced me to wear a chastity device. She said it would heighten sexual feelings for both of us and as usual, she was right. The longer I go locked up the more attentive I am to her needs, which have gone from servicing her orally every night to doing most of the housework around the house. As for me th...

A Cheater's Remorse

by milkydreaming51 on Aug 8, 2018
BDSM

When I got married to my wife at age 23, I thought everything would be a fantastic, smooth road for the rest of my life as I had a great career, was youthful, and had a woman who would always love me. Like most plans we make for us, that didn't ring true. After only 4 years, I was stuck in a sexless marriage with Lindsey. We never had sex anymore. She was al...