Prissy Sissy Stories

7,690 results
Orientation
Length
Source
Infinite Scroll

Act 1 Scene 1

by lindiana on Sep 1, 2017
Humor & Satire

Cast of Characters Princess Prissy – a prissy princess Lenore the whore – a whore named Lenore Burly Tattoo/Piercing Artist – a burly bearded man who is a tattoo and piercing artist Narrator – a person who narrates Scene: A street Princess Prissy approaches Lenore the whore. Princess is wearing a modest white blouse and a dark skirt with practical pumps....

Ash's New Career Pt. 02

by Fibaro on Sep 28, 2020
Transgender & Crossdressers

Standing back in the doorway of her own room Keira was surprised to see the wonderful job Ash had done with his makeup. It looked nearly as good as her own best effort despite the colours she had given him. She smiled watching how Ash applied the last touches to his makeup look before coughing loudly just when he was putting the brush down. Ash who had bee...

Keeping Up With the Joneses Ch. 03

by DarkBlush on Sep 25, 2017
Interracial Love

So, I've decided to do back and forth narratives for this story only because I really enjoy both voices and they're so different. Another Heading back into the bathroom, I spit and rinsed before heading back into the bedroom. She looked so delicious, her brow furrowed with focus and the vermillion nightie tickling above her knees. I wanted to have her but...

Tear It Up: Under Pressure

by SEVERUSMAX on Sep 14, 2017
Group Sex

I woke up to hands roaming my body some time around nine. My cock was very much awake already and also quite stiff from the attention paid to it as well as the rest of me. I soon realized that there were many sets of hands, all of them caressing my flesh, and once I looked at their owners, they knew that I was quite awake from their efforts. The sunlight was...

Hunting Time

by Cndrlla69 on Sep 14, 2017
Romance

I closed my eyes and let the music wash over me. It was one of my favorite Jimmy Buffet songs. I swayed my hips and began moving to the beat, completely oblivious to my surroundings and my unclothed state. It was a hot, sunny summer afternoon in Florida at my favorite place to visit, Crystal Palms Resort. Not everyone who lived nearby even knew that this wa...

Discovering Mistress Sarah's World Pt. 07

by oneguy4fun on Sep 12, 2017
Transsexuals & Crossdressers

CHAPTER 18 A Life Changing Decision Sunday morning was not much different than the day before for Josie. He woke-up on the floor outside Mistress Sarah's bedroom, dressed in a silk night-gown and his cock was hard and aroused when he awoke. Just like Saturday morning, he crawled into the bedroom. Mistress Sarah was waiting for him. She was lying on her side...

The Society Ch. 05

by Barno on Sep 19, 2017
Transsexuals & Crossdressers

"I don't think that I'm the right person for this. You need someone more experienced. What if I fuck this up? I'll get my balls snatched right out from under my cock!" I was more than a little nervous watching Serena and Corinna rifle through my closet. "Your balls were snipped off quite a while ago my dear and the woman who owns them has given you her orde...

N.U.D.E.

by bigrimmstales on Sep 16, 2017
Exhibitionist & Voyeur

N.U.D.E. I saw the tiny brass panel adjacent to the ostentatious display my firm uses to advertise itself. I'd never seen it there before and all morning as I went about my work as Company Director I couldn't help but want to find out more. Curiosity about what the acronym meant was eating me up inside. I could not understand why. It was unusual to see full...

Not What I was Expecting

by gbr2004 on Sep 11, 2017
Fetish

THINGS DON'T ALWAYS GO THE WAY YOU EXPECT Another boring night. My name is Steve. I moved to Arizona a couple years ago. As so common, another divorce man, 51, in decent shape but living comfortably without many aggravations at the moment. My problem is that I can't stop having the same thoughts in my mind so often. Thoughts about the kind of woman I desire...

I Make Believe I'm a Cuckold Ch. 03

by donaldelliott11 on Feb 3, 2020
Transgender & Crossdressers

This is the third chapter of "I Make Believe I'm a Cuckold." You should read those first. [Writers love feedback. Please comment on and rate this story. About 99 readers out of 100 do *NOT* bother to do either. Comments help me improve my writing; ratings help other readers find what they will most enjoy reading.] +++++++++++++++++ Wednesday morning afte...