Small Penis Sissy Stories

255,740 results
Orientation
Length
Source
Infinite Scroll

Exposed to the Domme Club

by NancyPan on Sep 17, 2017
BDSM

I highly recommend that you read my story "The Domme Club" prior to reading this one as there is background in that story that I think will make this one more fun. Also, I continue to struggle with the narrow selection of categories. If you have read any of my other work, you will know that this is not just BDSM, but certainly has strong element of fetish, g...

Straight Guy Gets Some "Strange"

by nancyvasquez on Oct 15, 2017
Interracial Love

The Negro saw the bright lights across the street advertising the adult bookstore. He felt a stirring in his groin and he pushed down on his cock. He could use a jerk off session, he hadn't cum in a few days. It was a very warm night, and the rain had stopped, leaving the smell of wet asphalt in the air He went to the counter. "How much to go in the back?"...

Property of the Master Ch. 01

by BrightTightandWhite on Sep 26, 2017
Transsexuals & Crossdressers

I submitted this story a while ago under the name TightandWhite however I have forgotten both the password and email address I used to create that account. So this is not plagiarism I'm just resubmitting it. ***** I headed down to the community swimming pool glancing furtively left and right to make sure no-one was around. It was midnight on a Tuesday so t...

Property of Master Ajax Ch. 01

by TightandWhite on Sep 19, 2017
Transsexuals & Crossdressers

I headed down to the community swimming pool glancing furtively left and right to make sure no-one was around. It was midnight on a Tuesday so there shouldn't be, but I wanted to be sure. I clutched my bag tightly as I reached the changing rooms. To the left, the lady's and to the right, the men's. After glancing over my shoulder one last time and taking a d...

Sissy Hubby

by rj1774 on Mar 18, 2020
Fetish

In case these are not the fetishes you like; this story features pegging, CEI, and sissy training. * It had been a very long week at work, but I had finally made it to Friday at 3pm and was excited to relax over the weekend. Then a text from my wife of five years came in that started the snowball rolling down a steep mountainside. "Hi! I have to run a few...

The Neighbours Situation Ch. 02

by Missclo on Jul 3, 2019
Transgender & Crossdressers

I read the text over again and again, the feeling of fear still strong in the pit of my stomach from the last few minutes. What if she showed the photos to people? What other twisted commands had she got in mind for me? I decided I needed to get up and try and take my mind off of the situation the best I could. Surely this was the revenge for sniffing her p...

Counselling Changed Our Marriage Ch. 03

by Quietoldie on Dec 25, 2017
Transsexuals & Crossdressers

The fourth joint Interview Emily sits comfortably in the waiting room, texting and smiling. There is no question in my mind with whom my lovely wife is texting, nor much less any doubts about the lewd and obscene content of their texts. Emily looks totally ravishingly beautiful, dressed smartly in her business attire, her generous breasts bobbing up and do...

Sissy College Ch. 01

by MasterJW on Sep 11, 2017
Transsexuals & Crossdressers

All characters 18 and above. This series will eventually be filled with all the raunch you desire, but I like a little foreplay first. So sit down, slip down your panties, and enjoy! I love your comments! Chapter 1: Mathematics Welcome to Chester College: An exclusive all-boys Sixth Form College catering to talented young men from across the country aged...

Little Sex Toy Ch. 06

by keptsissy on Sep 26, 2017
Transsexuals & Crossdressers

Squatting on my heels, feet just up under the curve of my cheeks, I can feel the ruffles on my sissy sox up against my bare legs. They would tickle if I weren't so afraid and focused on doing what he demands I do in front of these men. My knees pushed up toward him and spread wide, don't dare hold them together, don't want to get slapped, I feel his hand o...

Sissy School

by zeta515 on Jun 19, 2018
Novels and Novellas

Copyright 2018 by Zeta All rights reserved This story may be freely distributed in electronic form but must include this copyright. Sissy School is a work for pure fiction and all locales, names, characters, places, and incidents are the products of the author's imagination. Any resemblance to actual events, locales, or living persons is entirely coincide...