Spanking Sissy Stories

28,144 results
Orientation
Length
Source
Infinite Scroll

Finding My Place Pt. 02

by LarryToLaura on Nov 26, 2018
Transgender & Crossdressers

Everyone in this is over 18. If you have any feedback, I'd love to hear it. ***** As much as I hate to admit it, I slept amazingly well. My whole life I had slept on a worn out mattress, with tattered linens, and blankets covered in holes. The room Noah had prepared for me had the softest sheets, pillows, and the most comfy comforter I had ever felt. Even...

Edward Lane's Argosy Ch. 07

by Ian_Ironwood on Sep 14, 2017
Exhibitionist & Voyeur

Edward considered just walking up to the front gate of the yard and sending his calling card to Gideon via the carbine-carrying Red Indian guards, but he dismissed the thought almost immediately. Such a re-introduction to his friend after so long an absence would seem so . . . mundane, and worse, unstylish. Edward had always been a bit intimidated by his chu...

Queen of Paradise Ch. 02

by ptpl_guy on Sep 16, 2017
Transsexuals & Crossdressers

This is a work of fiction. Names, characters, businesses, places, events, and incidents are either the products of the author's imagination or used in a fictitious manner. Any resemblance to actual persons, living or dead, or actual events is purely coincidental. ***** Earlier, Mark and Maria stayed at the pool as Mike headed up for his transformation. The...

Courting Cheryl

by RonWCB on Sep 14, 2017
Humor & Satire

Steering up the long winding driveway I had a feeling of apprehension. Leaving everything I've known my entire life and traveling half way across the country was more than just a little out of character for me, it was borderline insane. Up until a few weeks ago I was working in a managerial position for what I thought had been a stable successful manufactu...

Jesse's Journey Down a Rabbit Hole Ch. 15

by sadkins116 on Sep 14, 2017
Illustrated

I want to thank everyone for reading, voting and commenting on our story. I submitted the first six chapters, and Rebeccasm submitted chapter 6 through 12. I will be submitting chapters 12 through 18. We have both worked hard on this series and as such both deserve to share the postings. Hopefully you will visit both of us and enjoy the series. As I mention...

Dormant Desires

by electricpineapple on Sep 13, 2017
Transsexuals & Crossdressers

As I drifted off to sleep, I recounted the events from the last several hours. I'd flown in to see Allegra earlier that day, desperately needing a vacation from work. She'd been gracious enough to let me stay with her while I unwound and relaxed a little. When the plane landed, I found myself at the baggage belt, watching it go 'round and 'round with no sign...

Susan and John's Return Ch. 04

by dan57 on Sep 17, 2017
Erotic Couplings

John begins to enjoy his humiliation By Dan57 with characters from Jill York * When they returned home on the next Sunday evening, Susan immediately arranged for her husband John to move to his new bedroom. A cot and a cupboard would be his only furniture until the craftsmen had finished their job. John would have to live for a few days in the former lau...

Tammy the Transgender Witch Ch. 02

by transgirl84 on Oct 11, 2017
Transsexuals & Crossdressers

Hello all, if you are reading this story, I want to thank you as well as encourage you to read part 1 of this series. This picks up pretty much where part 1 finishes up. If there's any feedback or suggestions, please share. * KNOCK, KNOCK, KNOCK! I knew it was only a matter of time before the entire girl's dormitory wanted to know what just happened in he...

Life on the Ranch Ch. 01

by phoenixcinders on May 16, 2018
Transsexuals & Crossdressers

I can't believe those jerks threw cattle dung at me. No good, dirty rotten, a-holes. They got that shit all over me. That's not even the worse part... Well, that's up for debate. But to top it off we're out of hot water! I had to wash the bull shit off with freezing cold water. I hope to god Steph gets back soon. I wish I could tell her what those jerks did,...

Over his Head

by Bakeboss on Sep 14, 2017
Novels and Novellas

Part l: Gene meets Darla and turns from lab partner to personal servant before he knows what hit him. My name is Gene and this is the story of how I met and fell in love with the most beautiful creature in the world. I'm a typical college nerd, great at math and science but lousy in communication, especially with girls. Of course, this makes me painfully sh...