Strapon Sissy Stories

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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 Cuckold Ch. 03

by sissyboycamille on Sep 13, 2017
Interracial Love

Things had changed at home. My wife had been promoted at work. Since the children had left home she had been able to dedicate more time to work and it had paid off. She was dressing more professionally and was often coming home late. She had changed too, as she now had less time outside of work she had developed a no nonsense attitude. We still got the chanc...

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...

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...

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...

Sissywife Humiliation Action

by Cocktopia on Sep 15, 2017
BDSM

The dyed-black haired girl, mistress of this dungeon, was covered in large colourful flower tattoos, her hair cropped in an uneven fringe around the shaved sides of her head. Her nipples, clit, eyebrows and nose were pierced and threaded with simple silver rings which glinted in the dungeon's harsh light. She was very young and very pretty but her sex appeal...

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...

Seductress & Daemon: Sissy Pt. 02

by SeducedKnight on Sep 15, 2017
BDSM

********** A continuation of my initial story, the next morning... ~~~~~~~~~~ Zombe: a black rubber o-ring type bracelet worn locally, either on wrists or ankles (or both in my case, I have an oversized one that I wear as a necklace too). ********** I wake early the next morning, Seductress and the sissy are still asleep, the sissy and I are snuggled in...

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...

The Cuckold Ch. 02

by sissyboycamille on Sep 13, 2017
Toys & Masturbation

Since that strange evening the sex with my wife had become very intense. We had gone from having sex once every month or two to a few times a week. She seemed to have discovered a new found interest in sex. Everything turned her on. A few times she came home very late and had me on my knees in the living room licking her pussy for ages, her pussy smelling st...