Chastity Keyholder Stories

6,874 results
Orientation
Length
Source
Infinite Scroll

A Tale of Slavery

by gunnarsub on Sep 17, 2017
BDSM

Once upon a time there was a straight guy who was known by everybody as a well respected fellow. But he had a secret life. Nobody knew that he dreamt to become a feminized slaveslut, seeking an infinite and irrevocable blackmail relationship with a pitiless Mistress who would be prepared to break him with no way out. He wanted the Mistress to torment him n...

Arcadia Castle Ch. 14

by Hal1031 on Jun 8, 2020
BDSM

Chapter 14: THE HUSBAND ARRIVES 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. ------- *TWO DAYS EARLIER* I miss my wife. To be frank, I hadn't shared my wife's enthusiasm about this whole fantasy exploration extravaganza. Don't get me wrong, it wa...

Exposing Amy Ch. 05

by fannyrat on Mar 2, 2020
Fetish

It is vital to the understanding of this story to read the first chapters. As always I encourage comments as it helps to improve the writing. In the ensuing months, Paul and I continued our extraordinary life and enjoyed the surreal (and what many people would consider abnormal) ménage a trios with our elderly milkman Ron. For myself, life could not have b...

Letter from Ithaca

by justincbenedict on Sep 17, 2017
BDSM

Dear Shoeblossom, When I was in graduate school, I rented a room from a woman who was a retired dominatrix--Miss Elspeth. When Miss Elspeth discovered that I was a devotee of BDSM sites, she immediately took over my life. I left her care after getting my degree, but recently moved back to New York State and moved back in with her...I am a true submissive, t...

The Women in My Life Cuck Me Ch. 02

by Philyssis on Mar 18, 2020
Fetish

Continued from part 1, right in the middle of a sex club... I was relieved when my wife grinned. Then I was a bit concerned as it turned into an evil grin. "Wow Phil" my wife said to me. "I knew you had a dirty mind, but I didn't know you had THIS in you!" Amy, my wife's little sister, leaned over and kissed me on the cheek, then looked at Tara, "I'm s...

Evil Slut Bride Ch. 01

by PeterOmez on Sep 12, 2017
Loving Wives

"Love is the beast who will tear out your heart, Hungrily lick it and painfully pick it apart." - Concrete Blonde *** My name's Mandy Thompson and, even though I'm only 23, I've been a married woman for four years. But as everyone I know can tell you, I am NOT a faithful wife, hahaha. And when I say "everyone", that includes my husband David (or Davey, a...

Friends Locking Friends

by LordDragonFire on Jan 8, 2018
BDSM

"Oh, God. Yes! Yes! Yes!"Hands pounded into the wall in a rhythm with the headboard as two bodies writhed in naked ecstasy. Michael woke, yet again, to his room mate's cries of passion and the pounding on the wall. When he turned his head, the clock numbers read 2:36 in glowing red. "Again Kara" he complained, quietly, then bashed his hand into the wall....

Sissy, Hypnotized

by Slipperylock on Apr 8, 2019
Transgender & Crossdressers

It had taken six months to get to this point. As I stepped out of the bathroom, I caught sight of myself in the full-length mirror, and shivered. I was shaved below the eyebrows, hairless and smooth, except for a cute landing strip above my locked chastity cage. Other than the cage, I looked like a thoroughly average 21 year old boy, my small and skinny fram...

Sam's Story Pt. 02

by Shadykingcolor on Jul 30, 2019
Loving Wives

Editor's note: this story contains scenes of incest or incest content. ***** As I laid on the floor of my marital bedroom. Lube oozing out my ass, dried pussy juicy and semen on my face. I thought about the shit I was in. How Cassie had tricked me. How did I never notice that side of her before? How it was all Mel's fault for telling her. But more impo...

Letter from Los Angeles: Ms. Scunt

by justincbenedict on Sep 15, 2017
BDSM

Dear Shoeblossom, My name is Eliza Scunthorpe, a keyholder in Los Angeles I have read Leland T___'s whining letter to you and I want to clear things up! For instance there's Parrish! Parrish is a favorite client of mine. He is on a relatively lenient schedule--he is allowed to orgasm about once every other week. And he has privileges I don't usually gra...