Butt Plug Chastity Stories

100,740 results
Orientation
Length
Source
Infinite Scroll

Out of Control

by AlinaX on Jul 24, 2018
Loving Wives

I love my husband, Eric, but I am a highly sexed woman who finds it very difficult to say 'No' to interesting propositions. Eric knows this, but at least during the early years of our relationship he was more than able to keep me well satisfied. He has a kinky side too, and loves to see me in high heels and short skirts. He guards me possessively in public,...

A Harmless Fantasy

by Twileklover on Aug 18, 2017
Fetish

I have a lot of kinks, and to my never-ending joy, the woman I married enjoys most of them. She dominates me, locks my cock in a chastity device, occasionally whips me, and allows me to indulge my unending lust for her feet. So that makes it hard to explain why I have never asked her to erotically humiliate me. It came up a couple of times, in passing, and...

Home Office

by CL702463 on Jun 1, 2020
BDSM

We had not seen each other for weeks due to Corona. Texting was not satisfying yet kept my mental leash alive. Queen and pet. We decided to play Monday at noon. My place. The night before she wrote: "Don't bother dressing." I replied: "I have never answered the door naked." She made clear who is in charge: "I am not here for your comfort zone." 3 min...

Mistress Starla Proves Her Point

by justincbenedict on Apr 16, 2018
BDSM

Porky was weeping bitterly, and at the same time, his dick was straining, and quite excited. Who was this girl? Starla was his friend Spalding's cousin, and he'd seen how she enslaved him--Olivarius, the school's intramural lacrosse coach had told Porky that Starla had taught him how to suck his own dick... Several young women of Porky's acquaintance foll...

Sissy Instructions

by FrostShard on Sep 13, 2017
BDSM

Dear sissy, I trust you are preparing yourself well for our session next week. This session will be your final plunge into the realm of sissyhood. Thus far, you have simply dabbled in it, all the while essentially staying a man. All that will change starting from this session. Starting now, from the moment you finish reading this letter, one thing will cha...

The Office Boy Ch. 04

by Aussie Worm on Sep 25, 2017
BDSM

Here I was, back in the city, well an hours drive away in the suburbs, I had managed to find a small two bedroom house to rent for a while until I get things sorted out. I had managed to buy the basics, a little furniture, television, computer and other things, but in reality I had accomplished next to nothing in the two months since I had be asked to leave...

The Roommate Pt. 10 - Miranda

by ValoryG on Sep 13, 2017
Transsexuals & Crossdressers

True to her word, Miranda made sure Josh/Lori ventured out in public some more before his teaching duties resumed. The butt plug was frequently inserted, and when Lori asked why, Miranda remained mysteriously opaque about it. Lori was becoming more accustomed to the sensations down there - sometimes pleasant, sometimes a turnoff. After the movie (and the w...

Slave Immigrant Ch. 20

by OldGuy1026 on Sep 14, 2017
Sci-Fi & Fantasy

After receiving a cloned body I immigrated 127 Light Years from Earth to Free Skyes. Unfortunately I had to work and pay for that cloned body and I had very few skills a high tech society could use. So it was either become an Unskilled Labourer or a Sex Slave. I guess Human Recourses had me figured out correctly. All those years in BDSM chat-rooms and websit...

Trixie's Chastity 01

by trixie47cd on Sep 19, 2017
Transsexuals & Crossdressers

Part 2: Trixie learns his new role. Since my wife came home early and caught me masturbating in women's frilly lace 2 month ago, so much has changed. She has taken control of my life since I begged her not to spread the story and pictures of my humiliation around town. After I made the choice of submitting to her feminization training, there really was no...

Jerry becomes Jill Pt. 05: July 4th

by gasissynora on Apr 27, 2020
Transgender & Crossdressers

Jerry becomes Jill: Part 5: July 4th Week End This is the fifth part of my story about how I became Jill. After having started female hormones, Jill is introduced to group play by Mistress Rikki. The Fourth of July is on Monday and that Thursday evening at dinner Mistress gives me some information about the holiday weekend. She says, "Tomorrow you are done...