Ex Chastity Stories

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Chastity with Ex as Keyholder Ch. 03

by chastity_sissy on Mar 12, 2019
Fetish

Back at my apartment, I wanted nothing more than to just get the chastity device off of me, but I still couldn't help but be aroused at my humiliating situation. Here I was, chastised by my previous girlfriend who now controlled not only my orgasms, but whether I could have sex with another woman. Suddenly, my phone buzzed, notifying me of a new text messa...

Race to the Bottom

by jujou2006 on Nov 27, 2017
Fetish

The bump was totally unexpected. Jujou had been running round the track for some time and had fallen into that trance state so well known to the long distance runner. She hadn't even noticed that another runner had joined her on the track and when the contact came she lost her balance and spilled on the ground. "Watch out slow poke!" The taunting words dri...

Secrets of the Deep Ch. 05

by Lady Malachite on Sep 15, 2017
Sci-Fi & Fantasy

Once there was a little boy who never really grew up, but only grew older. As he grew to a respectable age, he never became anything resembling a respectable adult. He was also rather shorter than average. As the years flew by, this midget of a man grew more and more frantic because it became obvious that he couldn't live forever. His knees began to ache as...

Letter from Vines Village

by justincbenedict on Sep 17, 2017
BDSM

I drive a sterilized knitting needle through my son's left nipple. Sowell grimaces, but he is sucking on one of my bloody tampons, and his buttocks hurt from the vicious caning I gave him earlier. I surprise Sowell—when he's coming out of the tub, wet, naked and vulnerable, I charge in with my whippy cane and leave red, bloody streaks all over his slim whit...

The Keyholder Ch. 08

by AndreaJordan on Mar 7, 2018
BDSM

Amy was sitting astride Ben's waist when he woke the next morning. He was lying on his back with his arms by his sides, arms that were now pinned in place, immobilised by her thighs. She was sitting on his tiny chastity cage, enjoying the feel of the high security device resting between her bare cheeks. Her long dark hair hung down over her shoulders, mode...

Chastity of a Cheating Man

by crazythoughts on Sep 17, 2017
BDSM

He didn't know it quite yet but she had found his hidden messages on skype, email, facebook and even had seen his deleted messages on his phone. She then started to check phone records and saw that he had been talking to numerous women while they were dating and even as soon as the last week. She started to count up the time and noticed that it equaled many...

The Keyholder Ch. 14

by AndreaJordan on Nov 18, 2019
BDSM

Ben was now back in his original Prince Albert cock cage, over which he wore his full steel chastity belt. Amy held the keys to both. Living with his chastity keyholder kept Ben in a state of constant arousal and longing. The keys were just so close, with one of their favourite hiding places being the front pocket of Amy's jeans. Well, whether the keys like...

Letter from Toledo

by justincbenedict on Sep 13, 2017
BDSM

Dear Shoeblossom: I really enjoyed "Letter from Los Angeles: Ms. Scunthorpe's Rebuttal" and also the story from the Time-Lock computer Mistress in "Letter from Greater Ponsonby ." I also have a paid key holder, Phyllis. I grew up in a strict Evangelical family, here in Ohio, and our parents were very primitive, sexually... Masturbation and copulation wer...

Letter from Newark

by justincbenedict on Jan 8, 2019
BDSM

Dear Shoeblossom, I am just an ex-cocktail waitress who married a troubled but worthwhile guy. Mom always told me to find someone classy like a dentist or a Buick dealer. "Mariah, it's as easy to fall in love with a rich guy as a broke guy." But I fell for Raymond Withers, Jr. hard, and I married him right before he went to Vietnam. Still, as in all marria...

A Sissy Fantasy

by Sissy_Jeanette on Mar 30, 2020
Transgender & Crossdressers

My darkest fantasy has come true. I'm now a slave to a dominant couple. My ex-wife and her new boyfriend have taken me in, and in return I am dressed as a girl always and their maid and sex slave. Frilly panties, stockings and skirts, babydoll t-shirts, and a blonde wig are parts of my new uniform. Also I now wear a stainless steel chastity cage now encasing...