Sissy Small Penis Stories

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Orientation
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Infinite Scroll

A Sissy and His Master's Hand

by keptsissy on Aug 8, 2018
Fetish

AUTHOR'S NOTE: No character in this story is under the legal age of consent. They are all 21 years of age or older. No sex act in this story takes place other than between two CONSENTING adults. No character in this story does anything against their will or is seriously hurt, permanently physically harmed, abused without prior consent, maimed or killed. Ever...

A Picture Perfect Sissy

by meeah sue on Sep 16, 2017
Transsexuals & Crossdressers

"Holly, hold your breasts up. That's it honey. Squeeze the nipples between your fingers. Make them hard for me, sweetie." Jason lifted and pushed his soft breasts together, squeezed the small dark nipples, and hurriedly looked up to see if what he was doing was okay. He really wanted what he was doing to be okay. It was dreadfully important to be okay. Kare...

Mother Dear Pt. 12

by keptsissy on Sep 14, 2017
Fetish

My white frilly lace panties delicately pulled down passed my stocking tops, so as to not crimp the lace, dangle from my ankles. The twelve inch small chain that holds my ankles and the thin steel cuffs locked to it rests on the carpeted floor, the panties rest on top of it and cover the tops of my 3" spike heel pumps. My small but erect penis exposed in fro...

Euphoria Resort

by sissyashley4bbc on May 4, 2020
Transgender & Crossdressers

"Welcome to Euphoria!" a good looking black man said as he greeted my wife, Jess, and I. I couldn't help but notice two scantily clad maids getting our bags for us. "Come right thus way to check-in with your specialist," he directed us. We clutched each others hands and hurried in, we were giddy to get started. Euphoria was no ordinary resort, it was cou...

Afro Stress Relief Ch. 09

by llts1970 on Feb 3, 2020
Transgender & Crossdressers

After a hectic and traumatic weekend, it was Monday again, I was still in a state of shock after what had happened. I spent most of the day at my desk doing very little, and wondering if any of the loading bay crew had seen the photos of me kissing Drake's ass, but I thought they wouldn't recognize me, as I was fully made-up as a sissy in the picture, but I...

A Night at the Club Pt. 01

by Jemina004 on Sep 14, 2017
Transsexuals & Crossdressers

Dani nervously looked at his reflection in his trusty compact mirror. He was sitting in the passenger seat of Keyshawn's black Escalade, about to enter one of the most exclusive clubs in the city. His mascara made his naturally thick eyelashes flutter attractively, his eyeliner perfectly framed his blue eyes, and his Candy Apple lipstick was flawlessly appli...

Helping Jess Pt. 05

by mski on Sep 25, 2017
BDSM

I slept well that Sunday night which surprised me, though I guess I was probably exhausted. I woke up with my normal hard-on a bit before 5am, well it would have been a hard-on but for the cage. My penis was certainly trying. I never found it an uncomfortable feeling, just frustrating that there is no ending and I could not jerk off, and now who knew what wa...

A Sissy Saga Ch. 17

by Snurge on Sep 15, 2017
Novels and Novellas

Titled people were a weakness with Miriam Hancock. She frequently spoke of them with harsh condescension, but the snob in her heart secretly rated them higher than wealthy businessmen, and so it was with some delight she agreed to the visit of the ennobled Marchioness of Wiggleswick. The delight had doubled when she discovered that in both Debrett's Distingu...

The Man That Owns Me Ch. 03

by keptsissy on Sep 26, 2017
Transsexuals & Crossdressers

"Pull that sissy thing down between your balls! I don't care if it hurts. You'll get used to it. The whole point is to have it tucked between your balls, your little baby balls up on the side of it and sticking out in front! The sissy bitch I saw do it on the web did it, so can you." He brings the riding crop down across my butt, hard. I cry out as I strugg...

She Forces Me into Cuckoldry

by hismasterdivine on Sep 25, 2017
Loving Wives

This is my first fiction and features many aspects of cuckolding and BDSM. Forced feminization, spanking, body worship etc play a part in this tale, where a deluded subby boyfriend's thoughts run riot. If the story is a success, I might write a follow up, particularly due to its frustrating climax! ***** Dominant girlfriend wants a black lover, deluded b...