Small Penis Sissy Stories

255,740 results
Orientation
Length
Source
Infinite Scroll

Doggy Style

by keptsissy on Sep 13, 2017
Fetish

I feel his middle finger slide up into my butt. He drives me crazy every time he does that. Each time is like the first time. It's the most erotic thing he does with me. It makes me hotter than when he fucks me, breeds me. I never get used to it. Every time he does this to me it's like the first time. He pushes his finger into me as far as it will go. He fe...

The Dragon Ring Ch. 07

by Beatnic_jazzman on Sep 25, 2017
Sci-Fi & Fantasy

I saw place names and looked to find mine; it was on the left front. On the right front where I expected to find Sissy's was the coat of arms of the S'snoyme kingdom with the legend of 'Giver of the Bride'. I was horrified. I grabbed the marker and rushed double time to the reception room. I spotted Antic and rudely took his arm. "This is an abomination!"...

Sun's Out, Bums Out

by Sissylexy on Sep 21, 2020
BDSM

"Lexy, come here," Miss calls, she sounds cheerful. I get up from the hall, where I have been kneeling naked for the past 2 hours. Despite the sunshine outside, there is a chill in this small room. I struggle to my feet and skip into the living room, hoping that Miss is as playful as her call to me suggests. "Sit on the floor Lexy, by the sofa, facing the t...

Mistake

by magmaman on Sep 13, 2017
Loving Wives

{This story has sex outside of marriage in it, so if you will be outraged, then be forewarned.} +++ Sissy lay there in the soft bed, her mind in a whirl. She could hear the soft snores of the man who lay beside her. The room kept blinking to a reddish hue, right outside were the motel's large neon lights. She remembered seeing those, the red portion was...

Shopping and Sucking

by Subkoksukr4u on Mar 2, 2020
Fetish

Matt was in the kitchen as usual preparing breakfast. He'd been instructed to prepare all the meals according to a specific menu plan each day. He finished the sauce for the eggs Benedict got on his knees and waited. He was wearing frilly pink crotchless panties and a matching bra, his bright pink CB 6000xs chastity device was barely peeking out between...

The Pantysissy Diaries Ch. 03

by JPantyboyVSL on Apr 23, 2019
Transgender & Crossdressers

This is a 3rd person fiction story about my fantasies of being a Pantysissy. All characters in this story are made up, and are all over the ages of 18. To better follow this story read The Pantysissy Diaries Chapters 1 and 2 before reading chapter 3. ***** It was nighttime in NYC, and Jaymie and her 6 Mistresses had just left their apartment to head to Vic...

Domme Club Humiliation

by NancyPan on Sep 19, 2017
BDSM

I would never say that life was routine with Mistress Monica. She kept me on my toes—or, more literally, on my heels—at least around the house. On days when I got home from my law office before she got home from her corporate job, I would immediately take off my suit and tie and put on one of the frilly aprons Mistress preferred me to wear at home, and a pai...

A Sissy Saga Ch. 22

by Snurge on Sep 15, 2017
Novels and Novellas

By mid-afternoon Open Day for many was adjudged over, but while prospective clients and the purely curious were encouraged to depart the most valued of Miriam Hancock's supporters were skilfully spirited away elsewhere for tea and cakes. While the men went to the gymnasium, the ladies were assembled in one of the classrooms on the second floor where the desk...

Proud To Be A Sissy Ch. 05

by Kary_M on Sep 26, 2017
Transsexuals & Crossdressers

I awoke in almost total darkness, only a soft glow came into the hall from the kitchen. At first wondering where I was, my bed at home wasn't as soft as where someone, probably my new daddy had carried me after falling asleep on the floor. I shivered in delight remembering how my daddy had shared me with his two friends. It was wonderful having three very di...

Jennifer Monroe & the Ladies Ch. 02

by corduroysissy on Jan 14, 2018
Transsexuals & Crossdressers

Everyone stopped. The ladies all looked at Jennifer with their mouths hanging open, and Debbie just stood there mortified, not believing what he just heard. "Do you not speak English bitch, I said get the fuck out of here right now. That's your punishment." He didn't move. "Oh, are you feeling sorry now Tinkerbell, well tough shit, beat it, bye-bye." De...