Tiny Dicked Sissy Stories

99,700 results
Orientation
Length
Source
Infinite Scroll

Finding Claire

by Sissyhalo on Nov 26, 2017
Transsexuals & Crossdressers

*Before... I get cleaned up and instead a drink I have a big mug of coffee and a long, long shower. Thinking on all of it a lot. Then I check my bank accounts twice online. I go outside after slipping into sweats and walk around my house and the yard and the garage, the big barn one out back. It's my second house here actually with Roxanne getting the f...

Strawberry Milk Pt. 04

by Sissyhalo1 on Jul 6, 2020
Transgender & Crossdressers

Once I figured out how I wanted to experiment with this revelation on my nanos I decided on Dr. Corey as the start and Jill my porn store sissy. Dr. Corey was fucking me everytime I seen him and I started trying to concentrate as he breastfed from my huge titties. Not out loud but like mentally to my nanos. ~Harder, a harder bigger cock...more sperm, more...

Girl's Night Pt. 07

by DifferentBreed on Sep 14, 2017
Fetish

This a continuation from an earlier story. It contains fetish themes of forced feminization, public humiliation and other erotic themes that may not be to everyone's taste. If you enjoy these, please read on and leave comments as to how you'd like the story to evolve or what you like. Enjoy. - DB ***** Fisher slid across the passenger seat of his Jeep, man...

Sissy Powers Ch. 09

by ClarasBestFriend on Sep 29, 2020
Sci-Fi & Fantasy

When we made our way into the living room (with me back as Leah), Connor's eyes bugged out of his head. "MMM MMM NNN!" he screamed through his gag, a sock balled in his mouth and held in place by duct tape. "Oh, baby, sweety it's okay!" cooed Heather, moving over to him. "These wonderful people have shown me why our relationship is so bad! Good news, it's n...

The Intern Ch. 04

by FrostShard on Mar 6, 2018
BDSM

The day after Mengxia had me listen in to her having sex with her boyfriend, I went back into work with some trepidation. Aroused from my three weeks denied orgasm, humiliated by the events of the previous evening and nervous about my meeting with Mengxia that evening, I could barely focus on work, and it seemed to take ages for 5 pm to roll around. At last...

Mistress' Party

by chained_sinner on Sep 17, 2017
BDSM

As I walk into the room, I hear my Mistress talking on the phone with one of Her girlfriends. She is making plans for that night. I'm not sure what Her plans are exactly, but She does raise Her voice a bit when She makes comments about how much She enjoys Her black lovers and how much bigger they are. When She sees me standing there, She looks at me and poin...

Jillian's Island

by clinton09 on Sep 14, 2017
Celebrities & Fan Fiction

[©2010 BY CLINTON09; ALL CHARACTERS OVER THE AGE OF 18; NO EVENTS DESCRIBED ARE TRUE] If you ever watched NFL football on Fox a few years ago, or ever lived in the LA basin and watched a certain local station's weather babe, you know Jillian Barbarie. Thinking back to the 1950's and 1960's: In those days of yore, women would fight like demons to keep their...

A Sissy's New Daddy Ch. 05

by sissyneko on Sep 25, 2017
Transsexuals & Crossdressers

When the loud speaker blared that Billie had a visitor he was tied to a stool. Billie had become a plaything for a few of the more business savvy residents of Blofield State Penitentiary. When prisons became smoke free buildings cigarettes were no longer the illicit currency of choice. Stamps had come into fashion because they couldn't keep you from mailing...

Priceless

by MidnightWriter on Sep 19, 2017
Loving Wives

The look on her husband's face was priceless, that submissive mixture of shock, surprise and arousal, when he walked back into his living room and saw what we were doing -- right there in his favorite recliner. Tara was in my lap facing me, slowly, seductively wiggling her firm ass over the huge bulge in my tight faded jeans, her arms around my neck, suckin...

Keith's Caught in a Costume Pt. 02

by gaildaniels84 on Dec 24, 2019
Transgender & Crossdressers

Keith steered his car into the parking lot of Northmark Mall and into a parking spot. Then, his hands returned, zombie-like, to the steering wheel, and he stared off into the distance. He couldn't believe what had happened. He'd got caught, rubbing his dick, dressed in a cheer-squad uniform, by the hottest teacher at his school. She'd humiliated him, made hi...