Prissy Sissy Stories

7,690 results
Orientation
Length
Source
Infinite Scroll

The Neighborhood Ladyboy Ch. 01

by Rstyusameg on Sep 16, 2017
Transsexuals & Crossdressers

All characters are fictional, except me, everyone in the story is over 21. My stories will involve, male/male sex, crossdressing, racism, bad language, and drug use. So if this offends you please don't bother reading. * Wearing my favorite low cut denim jeans, showing off the "tail" of the whale from my stringy pink thong, I walked into Albertsons. A loca...

Camping With a Size Queen

by LynnGKS on Sep 14, 2017
Loving Wives

No sooner had I secured the tent and got my belongings inside than what had been a light rain suddenly turned into a downpour. Fall weather! The temperature must have dropped ten degrees and the wind had picked up big time. It was a good thing I decided to camp here after seeing that rain cloud. No way could I have made it those last few miles down the mount...

David & 'Lyssa

by millennium_bard on Sep 12, 2017
Sci-Fi & Fantasy

This story was written by my late half brother Seasparks before he passed away. He never got the chance to submit the story before he died, although we did talk about it many times. So I am submitting his final story as a tribute to his memory. This is only the first chapter of many that he had written for this story. The rest of the story will be submitt...

Librarian Play

by Lia Monde on Sep 12, 2017
Erotic Couplings

Friday afternoon Gina called Alex to invite him to study at the library. Studying was the last thing he wanted to do to start the weekend. Normally, he would have said 'No thanks', but, since he didn't have other plans, he asked, "Why the library? That place is dead." "That's the point, dork. Less distractions." she answered. They were both twenty year ol...

Delving into Femdom Ch. 03

by readytokneel2907 on Aug 31, 2020
BDSM

** Chapter 7. Beginning my Training After closing the door behind me after my first session with Domina Electra, my heart was racing. I couldn't believe what had just happened, and instead of taking an Uber, I elected to take public transportation, which wasn't far away. While it was snowing, it wasn't overly cold, and I was excited about the possibility of...

David & 'Lyssa Ch. 03

by millennium_bard on Sep 15, 2017
Sci-Fi & Fantasy

David and the others stared at 'Lyssa as she lay there out cold. "Damn." Said David. "Is she all right?" asked Bitsy. David knelt next to 'Lyssa and patted her cheek gently. "Wake up Honey." 'Lyssa stirred and opened her eyes. She threw her arms around David's neck and hugged him desperately. "I thought I had lost you Beloved!" She sobbed against his sh...

Shalane

by 2Xwidderwoman on Sep 13, 2017
Romance

This is a long story, written as one piece, so I'm choosing to post it in one submission. There are actually only two sex scenes within a short period of time, but that means, of course, that the remainder of the story is not filled with that kind of content. Read as you like. The story reads better as one piece, rather than chapters. A very heartfelt Thank...

Discovering Mistress Sarah's World

by oneguy4fun on Sep 11, 2017
Transsexuals & Crossdressers

Chapter 1: Meeting Mistress Sarah Joe's heart pounded fiercely as he stood at the door to his Mistress's house. He did not expect to be so nervous at his first meeting with her. After all he had known her for over a year. Mistress Sarah had been gracious enough to allow him into her world. He was fortunate to fall under the control of such a beautiful domin...

Road Dog

by TwistedPanties on Mar 3, 2020
Erotic Horror

It all started with a bit of fun on his road trip. Bryan was en route to San Francisco to hang out with an old female work colleague, as "friends". She was a couple years older than him, 32 to his 29, and she had a great apartment downtown. Of course Bryan had wondered if she would let him put the moves on. It didn't matter if he got to hookup with her or n...

Billy's Trials

by cheto1 on Sep 14, 2017
Erotic Couplings

Now, I felt my balls tighten and the cum quickly squirted deep in her warm wet tight well-fucked pussy. She fell forward on my chest and kissed me softly as only a loving woman can. Lifting her head slowly, she asked, "Billy? Is it like this every time or only with you? Mike never acted like that. He never kissed me down there or made me feel all tingly lik...