Prissy Sissy Stories

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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...

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...

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...

My Girlfriend's Sissy Roommate Ch. 03

by SEVERUSMAX on Sep 16, 2017
Transsexuals & Crossdressers

I had to admit to myself that Larissa had never looked as sexy and drop-dead gorgeous as she did right then, bent over as I fucked her from behind and she took me deeper inside her twat. I fucked my new girlfriend so hard that she moaned and pushed back at Rain and me. He could feel the force of her hips and ass as she bumped her crack against his tongue. I...

Life With Miss Ida Ch. 05

by Sheermistress on Dec 3, 2017
Transsexuals & Crossdressers

Most evenings, dinner at home consists of me preparing all meals, serving it up to the table for both Mistress and I, having pleasant dinner conversations and then me cleaning up as always - just part of my Sissy role really, and one that I'm more than happy to undertake. And, dinner is always; entrée, light main meal and some kind of dessert - all served...

A Letter to Our Pantyhose-Sissy

by Sheermistress on Sep 19, 2017
Transsexuals & Crossdressers

I'm on my bed on my knees, my skirt pulled tight and just a little high, exposing my control-top pantyhose to your eager eye. My feet are dangling over the edge of the bed and you, my little pantyhose-slut, are standing behind me, dressed in your sexy schoolie outfit and mary-janes. Your face is made up in a prissy, sissy, teen-girl way and your hair is fini...

Power of Panties - The Beginning

by satinmarabana on Sep 12, 2017
Transsexuals & Crossdressers

When I was growing up, underwear was just one of those details of life. Always wear a clean pair in case you get in an accident! Sure it was nice to get sexy pairs as I got older. I still remember my first satin bra and panty set from Victoria's Secret, a gift from my older sister who delighted in showing me the ways of the world. But I never understood wha...