Prissy Sissy Stories And Pics Stories

369,077 results
Orientation
Length
Source
Infinite Scroll
SmutMD: The World's Biggest Erotic Literature Search Engine.
© 2025 SmutMD.com

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...

A Birthday to Remember! Ch. 05

by searic on Sep 11, 2017
Transsexuals & Crossdressers

Decidedly put in my sissy submissive place by Mistress Leader Marta, I resolved to be much more careful and obedient. I also was aware of my excitement at her Dominance and power. When another participant sat down next to me, I was recovered enough to look up to say hello. I recognized him as one of those I had seen earlier standing around and chatting afte...

England Pink

by Stillherer on Sep 16, 2017
Transsexuals & Crossdressers

Tanya knelt in the middle of the room rocking back on her haunches slightly stunned, struggling for breath. Cum. Cum coated her face. Cum dribbled from her mouth. Cum dripped from her chin. Cum. Cum slid down her forehead. Cum streaked her hair. She tasted cum. Breathed cum. Cum pooled in the cups of her pretty pink bra. Cum soaked her pink slip making it tr...

Another Submissive Slut Ch. 02

by Stillherer on Sep 19, 2017
Transsexuals & Crossdressers

I spent a tension filled week on edge. I was easily distracted from even the simplest of tasks as the memories of my adventures in the parking lot with Those People continued to haunt me. I fluctuated between arousal and disgust as visions of my performance played over in my dreams both waking and while a sleep. I had become nerve rattled, jumping at every s...

My Stroll outside the Car

by triffle64 on Sep 12, 2017
Transsexuals & Crossdressers

It was a beautiful evening in the spring of 1982. My wife and I were taking a drive up the coast of California for an evening stroll. She was driving. We had been married for about 5 years. She was 27, and I was 30. My wife is feminine, but she grew up as a tom boy. I had no idea that she would take so well to my submissive desires to be her sissy husband. T...

Mommy and Goddess

by force_transitioned on Sep 12, 2017
Transsexuals & Crossdressers

Andrew never saw the noose. He was uncomfortable around his new mother in law - his wife's new step mom. And rightly so - he was, after all, going through the woman's intimates since the day she entered their lives, some two years ago, shortly after the marriage. Had he overcome his guilty reaction, he may have noticed a recurring theme in their conversa...

Tales of Sub Asian Sissy Ch. 04

by subASIANsissyJADE on May 6, 2019
Transgender & Crossdressers

(Thanxxx so much for taking the time to read me stories! This is just my fourth post and I'd absolutely love any feedback... also, please feel free to reach out if you just wanna chat with a very depraved and submissive Asian sissy) ***** Dave threw my dress at me. "Hurry the fuck up, you stupid slut. My wife gets home in a couple of hours and I need to cl...

Robin and Jimmy Olsen - Sissies Ch. 01

by tawnysuede on Sep 15, 2017
Celebrities & Fan Fiction

Note that this story stands separate from other stories I have posted. * "If you hunky men will excuse us for the moment, we girls have to go... powder our noses!" Robin said as she scootched around on the cushions of the private booth. Jamie rose and joined her. Their dates watched the two girls' rounded asses sway back and forth as the two sissies walked...

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...

House Rules Ch. 09

by EROTICbearscribe on Jan 22, 2020
Transgender & Crossdressers

AUTHOR'S NOTE: This story contains characters and references to events in two previous stories I have written: Just Across The Hall and PIXIE: Sissy Stripper. It is not necessary to have read these two story chains. This chapter of House Rules could stand on its own for entertainment purposes. If, however you want context, please read the other two stories f...