Sissy Strapon Stories

1,000 results
Orientation
Length
Category
Source
Infinite Scroll
SmutMD: The World's Biggest Erotic Literature Search Engine.
© 2026 SmutMD.com
Create your own smut fantasy with AI

Forced Strapon

by trypewyre on Sep 12, 2017
Fetish

One weekend while sitting back in my chair, I was watching a movie. My mind started to wonder when I drifted off to sleep. I awoke a couple hours later to a touch on my shoulder. Knowing it was my kinky redhead girlfriend, I thought nothing of it when I drifted back asleep. A few seconds later I felt a hand slowly move down my chest and stopped on my flaccid...

Sissy Sisters

by Queen_Diana on Apr 22, 2025

Joining a sorority was a great idea. Beautiful girls, cute outfits, amazing parties, and hot guys to boot. There’s just one tiny problem for Delta Gamma Sister Kissy, the one nestled right between her luxurious thighs. A tiny, two inch clitty of a problem. No one knows of course, god forbid, Kissy passes just fine as a Sister, standing at five foot four, 120...

Strapon Dream Cum True

by AfroerotiK on Sep 13, 2017
Fetish

Edward sat at his computer screen, staring at his monitor until his eyes started to close from exhaustion. Every once in a while, he would get so horny, so desperate to experience his fantasy he would stay up all night just stroking himself and looking at porn, desperate to feel . . . it. He had pretty much resigned himself to the fact that he was never goi...

Brittany's Strapon Hell Week 04

by humbleslave on Sep 14, 2017
Celebrities & Fan Fiction

I am attempting to make these stories stand-alone as well as make sense in a series. If you like this, make sure to read my other stories. Think of your votes and comments as your contribution to my stories! Thanks! After the week I'd had so far, including my most recent ordeal at the softball fields, I didn't figure it could get much worse. Today I had be...

Brittany's Strapon Hell Week 03

by humbleslave on Sep 11, 2017
Celebrities & Fan Fiction

Brittany's Strapon Hell Week 3: "Fear with Jenna and Vanessa" I am attempting to make these stories stand-alone as well as make sense in a series. If you like this, make sure to read my other stories. Think of your votes and comments as your contribution to my stories! Thanks! * It had been a long week for me, and I had a feeling there was still a long w...

Seductress & Daemon: Sissy Pt. 01

by SeducedKnight on Sep 15, 2017
BDSM

After Eating out my Seductress for the last hour, we hear a knock at the hotel room door. "Go open it." I go to the door dressed only in my rubber wrist and ankle bands with heels and a pink crotchless panty, I have a plug in my ass and a cold metal cage on my cock. I open the door wide in my full nakedness to reveal a prettily dressed sissy outside. "...

The Sissy and the Pet

by Detailed_Dominant on Sep 18, 2018
BDSM

I sipped my drink and let my eyes dart back and forth between my phone and the entryway. I hadn't wanted to risk being late, so I tried to make sure to arrive 10 minutes early. Maybe I had just estimated the traffic wrong, maybe I had just been more eager for this meeting than I was prepared to admit to myself. I showed up almost 40 minutes ahead and schedul...

Nyomi Banxxx Strapons Shane Diesel

by Samuelx on Sep 17, 2017
Celebrities & Fan Fiction

Lying on the table, legs in the air and mouth slack, porn legend Shane Diesel was having the time of his life. Standing over him, looking sexy in a shiny red bra and matching panties was none other than Mistress Nyomi Banxxx. The tall Black dominatrix looked at the light-skinned, muscular Black stud as she worked the strap-on dildo into his asshole. Grinning...

Haitian Dominatrix with a Strapon

by Samuelx on Sep 1, 2017
Group Sex

Black men the world over got this nasty habit of walking around like they own the place. Act like they're the toughest guys. Swagger like they've got the biggest dicks. And I both love and hate them for it. My name is Jeannette Saint-Mathieu. I was born and raised in the town of Cap-Haitien, in the North side of the Republic of Haiti. I've been living in the...

Instructional Jerkoff Sissy

by dirtywordygirl on Aug 19, 2017
Exhibitionist & Voyeur

Right now, I just want you to lay back on the bed and show me what you have down there... No! I DIDN'T SAY YOU COULD TOUCH IT! That's very naughty of you to do that. First you have to ask me, so let go of your cock and show it to me like a bad little girl...you're a very bad little girl, aren't you? Let's get you a little wet and slippery, ok? Ask me if y...