Sissy Diaper School Stories

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Orientation
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Infinite Scroll

PIXIE Sissy Stripper Ch. 04

by EROTICbearscribe on Jan 20, 2020
Transgender & Crossdressers

Author's Note: There is a category switch in this chapter. The beginning chapters can be found in GAY MALE. Seeing as what happens in this chapter, the new category is TRANSGENDER & CROSSDRESSERS. ***** THE PINK BOY was located in the warehouse district across town in an eclectic area known for its nightclubs and specialty bars. Within a six block radi...

Transforming Brent Pt. 03

by sissymissyct on Oct 8, 2019
Fetish

Over the next few days I removed most of my male clothing from the house and donated it to Goodwill. I met Wendy as she got out of work each day and we went shopping. The first time was for regular clothing. Skirts, dresses and blouses, leggings and shoes and regular lady's sportswear. Thursday it was lingerie night. I ended up with multiple bras and camiso...

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...

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...

Humiliated Stable Sissy

by SissyTwinkleToes on Oct 5, 2020
Transgender & Crossdressers

After a long week at work, I was looking forward to a quiet weekend of relaxing in front of the TV with a beer, but my fairy godmother had other ideas. "Good morning sissy," came her stern voice as soon as I woke up Saturday morning. I whimpered, immediately knowing I was in for a humiliating weekend. She frowned, not pleased with my whimpering. She's an ol...

Ultimate Sissy Weekend Ch. 07

by SissyTwinkleToes on Mar 10, 2020
Transgender & Crossdressers

Ruby is sat flicking through a magazine. Mid-twenties, she's been working in the tattoo parlor since college and is soooo bored. So her face lights up when two sissy dumplings mince into the tattoo parlor. She gasps at their ridiculously effeminate outfits that no woman would be caught dead in. She can't believe they've handcuffed themselves together and loc...

Letter from Carker's Rents

by justincbenedict on Sep 24, 2019
BDSM

Dear Shoeblossom-- Since I taped this, I also have enslaved my brother-in-law Santiago and his basketball team. So I have real progress going on here in Carker's Rents! Love, Sugar Perez "Sugar, I am having a devil of a time getting these thorns out of my, um--" "Your diaper. Say it, Esteban." "Don't--don't you think it was punishment enough for me to...

Ultimate Sissy Weekend Ch. 06

by SissyTwinkleToes on Feb 4, 2020
Transgender & Crossdressers

Susie wonders if she'll ever get used to the horn honks. The gasps. The shouted comments. The whispers. The cruel laughter. She is stood with her sissy sister, Tinkerbell, in her pink OTT sissy dress she's been trapped in for over two days now, on the corner of the bad neighbourood where she now lives. It's 7:45, and she's been stood in public for almost two...

Isabella's Reversion Pt. 02

by silverbackteddy on Sep 16, 2017
BDSM

Note from the Author: This is a story about ABDL. The first word being Adult. All sexual encounters center around Adults, above the age of 18. This story also contains BDSM, plushophilia, watersports, and various other fetishes. For those that are grammar freaks, please don't comment on my improper grammar use. I could care less. I do my best with spell an...

Yes, Mommy

by searic on Sep 13, 2017
BDSM

My wife/Mistress, Heather and I had over the years developed a large repetoire of ways of playing together, with me, of course, always in a submissive role. One of our favorites was her as Mommy and me as her obedient little sissy boy. What a delightful combination of humiliation and safety it created in me. However, as frequently was the case, she had deci...