Sissy Spanking Stories

28,144 results
Orientation
Length
Source
Infinite Scroll

The Doll Maker

by Fibaro on Jan 22, 2020
Transgender & Crossdressers

Editor's note: this story contains scenes of non-consensual or reluctant sex. ***** (This story was one I wrote and posted on Halloween. It's a bit more gruesome than my other works as a result.) *** Intro Carl had always been different, he was a quiet somewhat effeminate looking boy, taking mainly after his mother. From an early age he had loved playi...

Three Loving Wives

by donaldelliott11 on Mar 2, 2020
Loving Wives

This story contains three loving wives. I counted them. *** "I don't know why you haven't been able to seal the deal with Nancy," Peter Johnson said to his best friend. "She just doesn't seem interested in fucking me," Michael Dodson replied. "I'm like stuck on your wife's friend list." They were sunbathing next to the Johnsons' pool, naked, as they did...

Made to Obey Ch. 04

by madetoobey on Jun 24, 2019
Transgender & Crossdressers

Reprise: I'd been caught wearing my Sister-in-law's underwear and jerking off to a shemale porn site by wife (Ruth), Sister-in-law (Esther) and their mother (Donna). Ruth, as a part of my punishment, was setting me tasks until Esther (who'd taken my laptop and mobile phone) could verify I'd never visited such sites before. I'd been forced into a chastity cag...

My Mother's Boyfriend Shawn

by JHouston on Jun 18, 2019
Transgender & Crossdressers

There was a knock on the door to my room, "Come downstairs. You are drinking and playing poker with me." Shawn commanded. Shawn is my mom's boyfriend. He is a white 48-year-old 6'2" tall and athletic former-jock that grew up as a spoiled rich kid. He has never worked for a living and lives off of his grandpa's trust fund. My mother, Gina, and I moved in...

A Cuckold's Journey Pt. 03

by yukonnights on Nov 26, 2018
Fetish

The big day had finally arrived. In fact, for me it arrived so fast that I was on pins and needles all day until Sarah came home a little early from work. I had the house work done and was just sitting in the living room waiting when she walked in. "Hi babe," I said as I got up to give her a hug. "How was your day?" "It was good. We weren't too busy today s...

Halloween Party Aftermath

by Sabnock on Oct 19, 2020
Transgender & Crossdressers

Oh my GOD I'm so hungover. I creak my eyes creak open, and immediately regret doing so. Everything hurts. My head is pounding. My mouth tastes like something died in it. I try to sit up, pause, flop back onto the couch. At least I've got blanket. Wait... I'm not in my bed. Where the fuck am I? I rub the back of my hand over my eyes, feeling a weird, heavy...

The Lessons Ch. 04

by Charles Petersunn on Sep 12, 2017
Exhibitionist & Voyeur

This is Chapter Four of The Lessons. If you haven't already done so, you are encouraged to read the earlier chapters; otherwise, aspects of the story might not be understandable. Readers who find this chapter enjoyable are obviously encouraged to read the subsequent chapter. In any case, please do provide feedback. There are obvious sequels to this initial...

Donna's Bitch Ch. 04

by MTL17 on Sep 19, 2017
Celebrities & Fan Fiction

It was another typical day in Eric Foreman's basement. The gang was hanging out doing the thing they most like to do in the basement... watching TV. Well, maybe it was one of the things they most like to do in the basement. The gang was all there... except for one... "Where the hell is Fez?" asked Eric, as he looked around just noticing his foreign friend...

The Vacation Pt. 06

by medic45 on Sep 19, 2017
BDSM

This story is a work of fiction. The Characters do not exist in real life. Be warned. It contains aspects of Female Domination that are consensual and non-consensual. As with most stories, starting in the middle doesn't make sense. Constructive comments welcomed. ***** The Vacation begins I spent Monday recuperating from the weekend. Barbara had shown me...

The Spanking Actor

by 24UKBlonde on Sep 12, 2017
Mature

I could hardly believe it myself. He was even older than DD, much older; in fact he was also older than my dad. Yes, Jon was into his fifties. But that didn't stop him being an amazingly good fuck and probably the most interesting man I'd slept with and maybe had ever known. He was an actor. Not tremendously successful but a face that when seen in a film or...