Sissy Strapon Stories

8,068 results
Orientation
Length
Source
Infinite Scroll

My Mistresses, Their Strapon And Me

by pantysissyslave on Sep 13, 2017
Fetish

This story was edited by: blondevixen40735 My wife, or as she is now called, Mistress Emily came into my pink princess room as I was changing for the day. She was wearing a giant strap on cock that was swinging between her legs even when she wasn't moving. My tiny cock grew a little bit in my pink satin panties. Pink was now my official color. My room,...

Caught in Her Panties Ch. 02

by Knightofround on Sep 16, 2017
Transsexuals & Crossdressers

This is a fictional story as was part one. The content of this story may not appeal to everyone. It includes female domination, crossdressing, strapon, lesbian, gay, and such. Just keep in mind that it is fictional and should not be taken seriously. Otherwise just enjoy the read. ***** It has been almost a month since my wife Mary discovered my secret. She...

Female Erotic Police Squad Pt. 08

by mattpantyhose on Nov 6, 2018
Group Sex

Part 1: Alexandra & Tori Rick the informant Thanks to the investigation and the search the commissioner had been rescued, so in that regard the action had been a success. Victoria, the villain mastermind, had escaped though, so the FEPS was not fully satisfied with the results. But satisfactory or not there were still some deals to be fulfilled; the inform...

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...

Dark Maggie #03

by kneeler1138 on Sep 12, 2017
BDSM

Before she finally took me for good and all, my Mistress would send me panties. They were to 'inspire' me to write for her, among other things. She liked to remind me that I was still her servant, in spite of the fact that she was (at that time) a married woman, and I was in a relationship as well. Both her marriage and my relationship were so vanilla that...

New Rules Pt. 02

by skinnysailor on Sep 23, 2019
BDSM

"Shall we start with this?" The tip of her switch lifts my chin. She's an angel fallen to earth. I look into her beautiful blue eyes. Her long curly black hair tumbles to her shoulders. When she hugged me the satin and chiffon of her robe felt so good. She's blessed with a full figure, mature, but not fat. Her voice, like a soft caress tickled my ear. "You'...

Special Times

by devoutmalesub on Sep 13, 2017
BDSM

Thankfully it was summer again. I have the summers off and my wife a very flexible schedule. She brings home a good portion of the dough. But, like I said, I'm glad it's summer. Now we can spend some time together. Because during the rest of the year I have many papers to grade and classes to plan. Now it is summer and when my wife is not here I clean for...

Bdsm adventures

by Sgtwolf on Dec 7, 2017
BDSM

This story is for a compilation of many different bdsm adventures. It was formerly known as latex adventures, but as chapters developed they dealt more and more with different aspects of bdsm, and less consistently with latex. Latex still exists as a strong element in many of the chapters, namely because I like to write about characters wearing it. I created...

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A Change of Heart

by d_fantasy on Sep 14, 2017
Fetish

My girlfriend Emily and I have a good sex life, I love her very much; she was the first and only girl I have ever had sex with. She is about 5'6", nice size tits (not too large), long black hair, she's half Phillipino, half English. I'm 6'1", I have long brown hair and a dark goatee beard. We've been going out now for about 3 years, with no serious problems...

Creating Ginger Ch. 08

by Ms_Allison on Aug 31, 2020
Transgender & Crossdressers

Author's note: This is a story of a loving, married couple who wanted to expand their boundaries. It involves crossdressing, gender play and their foray into dominance and submission. If these are not topics you are interested in, then please move along. ~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~ Michelle awoke to the smell of coffee, which as of late had become her...