Sissy Diaper Boys Stories

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Hypnotized

by Satanicsissybitch on Sep 23, 2019
Transgender & Crossdressers

Warning: there's a lot going on here, diapers, sissies, interracial sex so if any of those things are an issue you may not like this story. *** Where do I even begin with this story? I don't know why but I feel absolutely compelled to share my recent experiences online and I can only assume it has to do with that horrible hypno-therapist one of my supposed...

A Prom Queen Fantasy

by bluesbirds on Jul 15, 2020
Transgender & Crossdressers

"Aww, isn't this little blue number cute?" Tanya squealed from the other side of the rack. I flinched hearing her voice; we had been shopping for almost 3 hours without a break. This was the first time I had gone shopping with Tanya since she found out about my crossdressing fetish. "Come to this side - let me hold it up to you," she demanded. I meekly co...

Marketing 101

by marybethsanford on Sep 16, 2017
Fetish

Players: Mark McLuhan, (Cindy Sue) first year college student and marketing intern at Little Miss Muffin, Inc.; Ms. Helen Pennyworth, owner and president of Little Miss Muffin Inc.; Carol Winters Vice President of Marking for LLM; Susan Evans, Product Manager of LLM; Julie Pennyworth, sister to Helen and professional dominatrix and practicing nurse. Tracy Ma...

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...

Behavior Modification Institute Ch. 07

by NancyPan on Sep 12, 2017
Fetish

I had been kneeling in front of Ms. Panington for some time as she finished her breakfast of omelet, bacon, toast, and orange juice. My mind was firing in a confused fashion and I was unsure which of many thoughts, feelings, and impulses to pay attention to, and which to ignore. Fight or flight was quite pronounced and I contemplated getting up then and ther...

Ultimate Sissy Weekend Ch. 03

by SissyTwinkleToes on Jan 13, 2020
Transgender & Crossdressers

Before today, Susie had only ever spanked herself. Nothing could have prepared her for the 220 spanks she'd received earlier, her first serious sissy spanking. Still her butt burns, even in its new pink poofy diaper. And now it's joined by fresh welts and lines on her inner thighs from the cruel canings of the redhead's ruler, as she happily decorates the tw...

Daddy's Little Sissy Diaper Slut

by Satanicsissybitch on Jul 14, 2020
Transgender & Crossdressers

I absolutely love wearing my adorable pink pull-ups for Daddy and I really love being his cute little sissy diaper slut! Daddy had always loved playing the dominant role with women but it was me who has him addicted to sissies and I've always been a little diaper slut. Well, a pull-up slut anyway. I always felt the adult diapers were not only boring and blan...

Ultimate Sissy Weekend Ch. 02

by SissyTwinkleToes on Dec 24, 2019
Transgender & Crossdressers

It had taken a good half an hour via taxi to get to this postbox, across the city from Sissy Susie's home. All so Sissy Susie could post five keys to herself, containing the keys that keep her and Sissy Tinkerbell locked in their ridiculous sissy dresses, locked in handcuffs to each other, and locked in the clitty cages that have kept them chaste for the las...

The Stepmother Ch. 2

by Clausimotto on Sep 16, 2017
BDSM

After the ordeal, Billy was dragged up the stairs. He was taken to his bedroom where his cuffs were tied to the bed. Billy lay on his back, in a dazed state while Jane and the girls stood over him. Jane mentioned, "Tomorrow I think Billy should go see my nurse friend. She can give him a check up and also she can show Billy how to take care of his slut hole....

The Training of Sissy Paula Ch. 5

by submissive~pet~ on Sep 14, 2017
Fetish

After the fuckings I had gotten from Max my asshole was so stretched, I had to wear diapers all the time. Mistress Carolyn used this to her advantage. She had a few men that liked sissy babies. The men would bring me all sorts of little sissy clothes. Dress me up and have me nurse their cocks as if they were bottles of milk. One day a new man showed up, he w...