Strapon Sissies Stories

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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...

You're Like a Little Boy at Times Ch. 06

by Myneed on Jan 24, 2018
Fetish

This continues the story of James and his Mistress Mel. Getting to know the characters and where they are at by reading the preceding chapters would help. Sorry it took ages to get this chapter out. All characters are over 18. ***** Mel had just taken me with her strapon for the first time. While she was talking dirty to me and making me beg for her c...

Awakening

by timewarp69 on Sep 16, 2017
Group Sex

Let me describe myself. My name is Tony. I am about 5'7", 153 lb., brown hair, blue eyes and have a 7-inch cock with an average body. I usually love extreme sports and am up for anything new or exciting. Another day as usual. After work, I headed to the bar I usually frequent to grab a few beers. I had just been dumped by my girlfriend of three months. I de...

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...

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. "...

Turned into a Slut Ch. 04

by xaitonnar22 on Sep 19, 2017
BDSM

After grabbing some quick sandwiches, Jennifer and I returned to her home. We found a note on the kitchen table from her parents letting us know that they would once again be out of the house for dinner. They didn't expect to be back until ten o'clock, it was seven right now. Once in her room, Jennifer commanded me to strip out of my jeans and bend over the...

Watching My Wife!

by limpjake on Sep 16, 2017
Loving Wives

My wife's decision to allow me to watch her began on Sunday at our family BBQ over memorial day weekend. We went to a near by state park camp ground where family members were camping for the weekend. We were having a good time conversing with family and friends, and eating the deliciously grilled chicken. That is when my wife asked me to walk with her to the...

Unexpected Encounter Pt. 01

by cddream on Mar 6, 2018
Fetish

It was a week night and I received a text from an ex girlfriend I haven't talked to in 2 years. I stared at my phone in surprise when I see her name pop up. My heart kinda skipped a beat and I opened the text anxiously. It was from Molly, she was the first girl I exposed myself to. She knew all my secrets and kinks from our past together. The text simply re...

Ms. Margo

by lyzunchik on Apr 3, 2019
BDSM

This is a partially true story, with some embellishments and enhancements out of my own fantasy. I'll allow you, dear readers, to wonder what is true, and what is contrived, where truth ends and fantasy begins. Enjoy. ;) Mistress Margo was waiting for me in the reception hall of Saint Petersburg Airport. I had been there a couple of times before, but this t...

Sailing Away Ch. 18

by Jasmyn_White on May 12, 2020
Fetish

Chapter 18 It's hard to tell day and night when your quarters are below decks. The advantage is you can sleep in the dark as long as you like without disturbance. Point is, I fell asleep hard when we got back to the boat. We pulled away from the dock, and with the diesels turning, I have no idea what time it is, nor how long I've been out. It's a low rumbl...