Chastity Prostate Stories

15,547 results
Orientation
Length
Source
Infinite Scroll

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...

Watch the Receptionist

by justincbenedict on Oct 7, 2019
BDSM

When Aram got back from lunch, he saw Holt, his new assistant, sitting in his chair, her long legs crossed, and she did look smashing in her cream muslin dress. Really, it was a bit beyond the office code, as the dress was more of a mini-dress thing, and just ended past Holt's thighs. But Aram enjoyed looking at Holt as did other men (and some women)in the...

Camboy's New Mistress

by pluggedforlife on Jun 5, 2018
Transsexuals & Crossdressers

His heart was pounding with passion. The big black dildo slid in and out of his well-lubed butthole, tickling his prostate. He could feel the large black penis glans squeeze out a drop of precum as he exhaled a moan of lust that was building up in his lungs. His steel chastity cage was flopping up and down, hitting his smoothly shaven crotch. His silver ho...

Surprise, You're My Bitch Ch. 01

by azzmn on Sep 15, 2017
BDSM

Warning this story contains the use of chastity and marijuana. This is however consensual relations between a husband and wife. * On Monday my wife Sam told me to make a phone call to my connection to get some weed for Friday. I knew this meant trouble I was in for a huge surprise. I was also instructed to take Friday off from work and that the kids would...

Chastity at the Airport

by Bowzer on Jul 30, 2019
Fetish

Editor's note: this story contains scenes of non-consensual or reluctant sex. ***** I stopped worrying about airport security. Simply, I have been through security enough times, with keys in pockets, pens, even a wrench, once, and another time a little tin of drill bits, that I just didn't worry about it. Heck, if all the stuff I had carried through the...

Six Month Anniversary

by slutslave201 on Sep 17, 2017
BDSM

It was 6 months ago today that Domina Kathryn accepted me as a personal slave in training. This had come after months of serving She who MUST BE OBEYED & WORSHIPPED. At the time She told me that there were many possible roles I could assume in the future ranging from a vanilla appearing husband to a fully transformed woman. I was told that it would take at l...

Letter from Sherier Place

by justincbenedict on Sep 17, 2017
BDSM

Dear Shoeblossom: I am a member and Substitute Treasurer of the Keeplock Club, a select group of women who keep their husbands and significant others in chastity belts. Our oldest member is seventy-eight, the youngest, a college junior. It's a constant vigilance, and I thought you might find it interesting, as your column discusses much of this. On Wednesd...

The Last American Male

by BuckRivers on Sep 12, 2017
Fetish

Author's Note: This story could reasonably be classified under Nonconsent or Fetish (Tease and Denial) or perhaps even some other category like SciFi. I think Fetish is the best spot, but will offer an apologetic shrug if readers think differently. Happy reading! * "Wake up, sleepyhead!" The guard tapped my bunk with her police baton. I opened one eye and...

Letter from Van Nuys

by justincbenedict on Oct 8, 2019
BDSM

Dear Shoeblossom, So I am a nice California girl, and when Kraven, my neighbor asked me to help him with his chastity belt training, I thought it was weird but kind of hilarious. I make a small living as a massager of sorts, my mom moved to Los Angeles to be a movie actress, and wound up in porn, and I got away from her and moved here to the San Fernando V...

WhiteBoy FuckToy for Ebony femdom

by flawlessgsmkt on Sep 12, 2017
BDSM

It's dark. I'm kneeling in a locked wardrobe. My hands are cuffed behind my back and secured to a ring in the wall. I pull at them a little where the cuffs are squeezed against my wrists. Not that there's any point. On previous occasions I've struggled against these cuffs in a desperate fury to escape. They held when I was trying my hardest to break free. Th...