Chastity Cruel Stories

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Orientation
Length
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Infinite Scroll

The Greatest Knight Of Your Life!

by MeganOckers on Jun 9, 2020
Humor & Satire

The Knight in Shining Armour/damsel in distress is a highly rated lockdown role play. But shining armour is hard to come by in these Covidinous times unless you're a member of the landed gentry or a scrap metal merchant. Also, when you visit a stately home have you noticed how small most of the suits of armour are? This is due to the multiple orgasms, sorr...

Indolent Ivan

by justincbenedict on Aug 27, 2018
BDSM

February 24 From JosephineMiller To: Wrenjohnson Wren, this is great. I couldn't believe it. Ivan proposed last night. He presented me with a diamond engagement ring. I was kind of like "I hope this isn't a bribe, you're still not getting to orgasm till the end of next month." Although for a ring like that, I might have given up the whole Mistress/Slave t...

Spalding and The Cheerleader

by justincbenedict on Sep 17, 2017
BDSM

22 year old Spalding Tyll walked home disconsolately, his knapsack hanging off his arm. It had now been 103 days since Mother had allowed him to masturbate, and it was hanging heavy on his young balls. Mother was mad at Spalding... She was going to punish him through humiliation by making him jerk off in front of the hottest cheerleader at Buttermilk Fall...

Christa's Dilemma Ch. 03

by bleedingmember on Sep 14, 2017
BDSM

I enjoyed the coffee Christa had made. And I enjoyed the view. Christa has always been gorgeous. But now was a bit different. Usually she is stylishly dressed, wearing classy and expensive clothes that emphasize her beautiful body without being vulgar. Today her clothing was more explicit, nothing left to imagination. She wore a very short black skirt showin...

In Bloom

by Slave2dbg8422 on May 6, 2019
BDSM

Chapter One We'd talked about all the things we wanted to experience, but the cuckolding fantasy was a bit different. It turned us both on, and we fantasized together often, but we'd both agreed that it would remain a fantasy only, until we both felt that the time was right. It had been an incredibly hot long distance relationship for the first four years...

Letter From Evanston

by justincbenedict on Sep 24, 2019
BDSM

Dear Shoeblossom, here is a recording I did with my boyfriend recently, he was unaware of it, of course...love your "Taped Confessions" series. thanks, Sinclair "Pongo, it was your fantasy, wasn't it?" "Sinclair, it was, but to be paraded through my aunt's garden party, where everyone is dressed so elegantly--" "Oh, you're exaggerating" "Every worthw...

Letter from Lythgoe Heights

by justincbenedict on Mar 7, 2018
Transsexuals & Crossdressers

Dear Shoeblossom: I want to tell you about my male master, Emil. He is Austrian, and although I am, I think a heterosexual male, not really bisexual, or maybe a bit now... But Emil is a find! Just this morning I was being tutored in how to edge without cumming. When I got close, kneeling in front of Emil, he reached down and tweaked the mousetrap on my ri...

The Chaste Crusader

by justincbenedict on Sep 17, 2017
Celebrities & Fan Fiction

Bruce's cock hardened more against Selina's traveling talons, the polished burgundy nails a somewhat abrasive contrast to her soft, milky white fingertips. Her fingers toyed with his thrusting, purplish erection as the raven haired beauty chuckled deep in her throat. Selina looked over at the tormented, naked millionaire, muscled arms bound behind him, and t...

My Story

by The Deviant on Sep 14, 2017
BDSM

I am a 22 year old female. I am also a masochist, not due to any inherent reason but due to the life that I have been living for the last 4 years. I had just turned 18 and was still a virgin when I had to go and live with my aunt (my father's youngest sister) and uncle. They live in a big house out of town. On my first day there, they showed me their true c...

Change of Control Ch. 04

by kaptiv8ed on Oct 26, 2020
BDSM

Several days had passed since the new couple had shared their latest "adventure" as they were calling the encounters. The two longtime friends had reunited after several years apart at a charity event less than a month prior, and the two hit it off very quickly. Both with time and opportunities in their life to explore and develop a transparent and mature re...