Chastity Girlfriend Stories

61,196 results
Orientation
Length
Source
Infinite Scroll

Happy Together

by Fafantasiz3 on Feb 12, 2019
Transgender & Crossdressers

-*ring ring* -... -*ring ring* -... -*ring ring* -... *clic* Hey there! (She speaks in a deeper voice, she sounds tired, she's probably been at it again, and for a while, by the sound of it) -Hey you. Busy? (His voice is as usual deep and melodious and terribly sexy -- she usually says she fell for his cock first, and his voice second -- the slight ec...

An Expensive Addiction Ch. 03

by NeverGuessWhatsNext on Sep 16, 2017
Transsexuals & Crossdressers

The Friday after my second encounter with English was just as eventful as I had thought it would be. My girlfriend got to town, and since we hadn't seen each other in weeks, she was hornier than hell. I picked her up from her parents house around 5 and we went straight back to my place to have sex before going to the party. A couple of months after we starte...

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...

Cuckqueaned by Hubs and Katie

by blueberrymuffintop on Sep 26, 2017
BDSM

I heard the keys in the door and felt the rush of wetness in my panties. David is home- with Katie. She laughs when the door opens and she sees me kneeling with a ball gag in my mouth and nothing on except a steel chastity belt. David walks over and pulls the gag out of my mouth, and pets my head, caressing my hair. "Have you been a good girl?" he asks....

Enslaved by Myself Ch. 05

by Lausunaht on Sep 14, 2020
Fetish

I had fully accepted my place as my clone's personal slutty sex slave and did anything he asked. I became his cum bucket and fleshlight and secretly became addicted to being his. I was still attracted to girls more than guys, but I hadn't seen a girl in months, in fact I hadn't seen anyone in person for months, except for my master. I had no choice but to...

A Better Life through Chastity

by chlomo on Aug 31, 2020
Transgender & Crossdressers

I wrapped my arms around Sophie and squeezed her tight as I shot my load inside her. She was perfect; large breasts a peachy rear all in a pale curvy frame, her long brown hair framed her big welcoming eyes gleamed up at me. I didn't deserve her. I sighed heavily and sank into her as she smiled and gently stroked my hair. I had failed her again, I knew it,...

10 Layers

by buzbybdsm on Sep 13, 2017
Fetish

I am blessed with a very attractive and intelligent girlfriend who has a very active imagination, especially when it comes to sex and our little hobby of bondage. We don't get to see each other very much, since I work in the entertainment industry and she is the manager of a large retail store. So between our crazy schedules, we don't get a lot of time to pl...

Separated but Dominated by Wife

by Subhubbyinmass on Aug 21, 2019
BDSM

About 8 years ago I met my wife online. She had a very nice femdom profile and I was submissive so I said what the heck. She was very pretty and she dominated me extensively for the first year. One of the things she loved to do was make me wear nipple clamps and chastity devices under my clothes while in public. Then she became bolder and began to advertise...

Enslaved by Myself Ch. 04

by Lausunaht on Sep 14, 2020
BDSM

I was getting used to my new life. My clone, who was now my master turned me into his obedient slave, into his maid and his toy. I'd cook us meals, do the dishes and all other tasks a housewife would usually do. My master took over the rest of my life, he went to my job, took over my business, my social life and made everything his. He started working out mo...

Workplace Chastity Law

by MissKateKees on Sep 13, 2017
Fetish

This is set several years in the future from the 'Women in the Workplace' series. The FEM NOW party is in government and has passed a radical new workplace chastity law. ***** Jada knew she had landed on her feet with her first job. Fresh from graduation at Athena University, she had secured a well-paid and prestigious position within Osiris Investments; H...