Long Term Chastity Stories

315,576 results
Orientation
Length
Source
Infinite Scroll

Transgender Avis's Incredible Power

by justincbenedict on Jul 4, 2018
Transsexuals & Crossdressers

Skokie, Illinois, 2009 Aiken Aycock was sad to be losing her brother Aiden to the operation. He was a great guy, but he gave Aiken the beatings and torture she needed. But he'd finally gotten the money to do the big change. Aiken had really enjoyed supporting Aiden, letting him live in her apartment...stripping naked when she got home, and taking a few fro...

Grace and Favor Ch. 03

by somethingslightlysuggestive on May 21, 2019
BDSM

I stayed in the shower for what seemed like too long. No matter how much I rinsed my mouth, the harsh, powdery taste clung. Defeated, I finally got out and dried off. I walked into the bedroom to see that he had gotten out the rope and was busy tying lengths to opposite bedposts. Once again, my pulse was in my throat. "Can't I... just... stay still?" I ask...

Black Women Cuckolding Black Men

by Samuelx on Sep 16, 2017
Interracial Love

Gleefully I spank my ebony sub's ass while thrusting my strap-on dildo deep into his hole. The tall, skinny Black dude moans deeply. Smiling, I continue fucking him. My name is Valerie Blackstone, and I'm a five-foot-eleven, curvy and sexy Black woman of Jamaican descent living in the City of Ottawa, Ontario. My slaves call me Mistress Africana. I'm one of a...

You'll be in Chastity, or She Will

by Revanto on Oct 6, 2020
Audio

All characters are 18 years of age or older. * * * * * Click Here to listen: .mp3 format or .ogg format. (10.5 min/mp3) * * * * * Do you two remember how sweet and innocent you were originally? You knew so little about BDSM. But you were so curious when you learned about it. And the more I controlled you, the more you liked it. Do you remember how you...

Breckyn's Bashful Boss

by justincbenedict on Jul 4, 2018
BDSM

Loudon and Jeanelle Gaskin waved at their baby sister as she walked down the hall of the big law firm. "Make us proud, Breck, baby." Jeanelle called. The legal secretaries of their formerly white-trash family had been enriched by this amazing place... Juanda, Riva and Desna, Breckyn's great aunts were "document specialists" whatever that meant, and had rec...

Enslaved Ch. 04

by fetishstories07 on Sep 18, 2017
Fetish

Mike finally fell asleep in the small hours of the morning. His cuffed arms and legs felt stiff and sore all through the night. Ball gag, causing his jaw to ache. His blindfold at least made it easier to nod off. Every time he thought of his situation, he would feel empty and defeated. Then he would reassure himself by thinking that a long term exit was poss...

My Daring Self-Bondage Public Walk

by Gagged1 on Sep 25, 2017
BDSM

The lower floors of the parking garage are completely full, but I find an empty parking space on the third floor in front of a concrete wall and thankfully head into it. It is late Saturday morning so I surmise there are a lot of people shopping. I turn the engine off and try to relax; the journey has been quite interesting. Driving for the first time in my...

Rubymoon Private Asylum Pt. 03

by Tombescent on Sep 14, 2020
BDSM

Dr. Smith struggled to wakefulness against the lingering remnants of the drug that had knocked him out. It was like his entire body was being weighed down by something that wanted him to sleep. Bit by bit he was able to pull himself out of dead sleep and into more of a druggy haze. Dr. Smith took inventory of his surroundings. He was naked, except for a l...

Arcadia Castle Ch. 09

by Hal1031 on Jun 26, 2019
BDSM

Chapter 9: A Visit to Dr. Chastity Each of the chapters in this series may be enjoyed as standalone stories, but the events and characters are richer within the context of the whole story. ------- I was startled to find Cole stretched out on my lounger the next morning, his intense gaze trained on me as I attempted to stir myself awake. "That's a lit...

Made to Obey Ch. 04

by madetoobey on Jun 24, 2019
Transgender & Crossdressers

Reprise: I'd been caught wearing my Sister-in-law's underwear and jerking off to a shemale porn site by wife (Ruth), Sister-in-law (Esther) and their mother (Donna). Ruth, as a part of my punishment, was setting me tasks until Esther (who'd taken my laptop and mobile phone) could verify I'd never visited such sites before. I'd been forced into a chastity cag...