Diaper Sissy Wets And Gets Spanked Stories

369,017 results
Orientation
Length
Source
Infinite Scroll
SmutMD: The World's Biggest Erotic Literature Search Engine.
© 2025 SmutMD.com

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...

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. 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...

Behavior Modification Institute Ch. 09

by NancyPan on Sep 12, 2017
Fetish

I want to finish the story since I have some avid readers and I don't want to leave you "hanging," so to speak. However, I've noted a significant drop in the number of votes and the rating of the last couple chapters - so if you want to encourage me or have constructive suggestions, please vote and/or leave a comment. ***** Confined to the cage and in tot...

How I Became My Neighbor's Diaperboy Ch. 01

by dl2424 on Sep 19, 2017
Fetish

My parents had left town for the week and I meant to have alot of fun. Little did I know where that fun would be found. I had been home for most of the summer after my first year of college and I was a little tired of some of my parents house rules. It wasn't that they were outrageous, they just made me feel like a little child. They wanted to always know...

Master and Four Subs

by totk6432 on Apr 17, 2018
Fetish

This is a fantasy written by myself for fun. It contains spanking, humiliation and fetish; if this bothers you please seek other authors. All characters are 25 years old or older. ======= The rule is simple: I ring the doorbell and let myself into Master Daddy's house. Susan, my 25 year old personal assistant, is with me. She is in charge of me at work. Sh...

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...

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...

Pinky's OK day

by Guromancer on Jan 19, 2021
BDSM

"HAHA PINKY WET THE BED~" Helena woke Pinky by loudly mortifying him, shouting out his bedroom window Pinky was stunned for a moment, in a daze. He figured out the humiliation he woke up to, instantly blushing red and cringing as he bolted upright, with a clenched jaw and arched back he looked wide eyed at his half sister. Helena was shouting to go...

Open in Reader

Wet Dream Pt. 03

by sissymissyct on Jan 28, 2020
Fetish

Gayle finished ordering items on line and checked the cam to be sure Georgia was asleep. The wetness in her panties told her what she needed to do. The payback for all those years that bastard cheated on her and how he had no idea what was coming to him, just made her pussy so wet. She was soon in bed enjoying her favorite toy. "I can't believe I slept so l...