Chastity Cage Diaper Stories

20,029 results
Orientation
Length
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Infinite Scroll

Valentina of the Colfax Inn

by justincbenedict on Feb 25, 2019
BDSM

SUPERBOWL SUNDAY AT THE COLFAX INN Valentina was toying with her husband's scrotum. Normally Val wore snug but dignified cashmere sweaters, but today she was clad in a belly tee shirt and what the longshoremen at Buttermilk Pier referred to as "whore shorts". Nibs, Val's loyal and faithful husband was bound to the narrow coffee table in his back office. Hi...

Humiliated Stable Sissy Pt. 02

by SissyTwinkleToes on Oct 5, 2020
Transgender & Crossdressers

I woke up exhausted at the crack of dawn to Fairy Godmother obnoxiously clicking her fingers next to my ear. I minced downstairs, still locked into my ultra prissy outfit (where was the key?) and my totally exposed diaper, already damp from last night. I shuddered as Fairy Godmother ordered me out into the back garden, where I stood and curtsied to the risin...

Dinner Date with Mommy Pt. 03

by SissyStoryTime on Nov 20, 2018
Transgender & Crossdressers

Part 3 is going to go a little off track from the previous two parts. I've been asked numerous times for more backstory on Sophie and Amanda, so we're going to go back in time to the day after the events of Meeting Mommy to see how their relationship really began to evolve into the kafkaesque clusterfuck of sexual depravity you're all so fond of. This story...

Ultimate Sissy Weekend Ch. 05

by SissyTwinkleToes on Jan 21, 2020
Transgender & Crossdressers

Susie can feel her diaper getting warm as she fills it with more pansy pee. 24 hours ago, she posted an envelope containing five keys, and still has another 48 hours until they arrive at her house. Those keys are for the lock that keeps her in her dress, the handcuffs that keep her right hand locked to this sissy on her left, and the tiny pinching chastity c...

The Wedding Ch. 08

by betamale08 on Mar 31, 2020
Transgender & Crossdressers

The Wedding (Patti Cake part 3) Chapter 8 -- Deceptions at the Reception... "Now then, if everyone is in agreement and there are no persons here who find this couple unfit for marriage... By the powers invested to me by God and the State... Patti and Dale... I hear by pronounce you as husband -- and wife... Dale -- you may kiss the bride..." *** It wa...

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...

Pro Domme Assignment Pt. 01

by Dprboy4Dominant on May 7, 2019
BDSM

I once served a daddy dom for quite a while and he set up a meeting with a Pro Domme for me. The following is part 1 of the email report that I sent to him. You had scheduled me to meet Head Mistress S at 5pm so at 3:45 I showered thoroughly, re-shaving my entire diaper area as you directed. I tried hard to scrub around the base ring of my chastity and spr...

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...

Earning His Keep

by Compliant1 on Sep 19, 2017
BDSM

I punched in the code and waited. I knew that I was being charged $1.99 for each minute, but I didn't care. I listened to the recorded music until a woman's voice came over the phone. "Tell Mistress Monica, have you been a naughty little sissy?" "No, but apparently my husband has." There was a long pause on the other end. "I just spoke to the manager. He...

Retired to a Whole New Life Ch. 02

by sissymissyct on Feb 11, 2019
BDSM

As my fate was now sealed by the lock, Mistress Michelle handed me the key and instructed me to put it on Cara's ankle bracelet. I gently undid the clasp and attached the key as instructed. I re-fit the bracelet and lovingly kissed her foot, and then Mistress Michelle's. They helped me too my feet and we went back out to the living room, Michelle locking th...