Sissy Strapon Stories

8,068 results
Orientation
Length
Source
Infinite Scroll

Our Sissy Slave

by purekink on Sep 25, 2017
Transsexuals & Crossdressers

Let me remind you how you came to be in this situation before you refuse. I've been bi-sexual since I was old enough to have noticed how horny women made me. From the moment I noticed, I was unstoppable. My dominant personality seemed to bring me more girlfriends than I could really use. But I always thought the only thing better than a submissive girl is a...

Candi's Conversion Ch. 04

by CandiCumminz on Oct 24, 2018
Transgender & Crossdressers

It was early afternoon when we pulled up at the mall. Mistress Luna had me drape myself sluttily over her car while she took some photos for my Instagram. I was still dressed as a sissy bimbo doll, having been styled by Crystal, a much more experienced sissy in servitude to another dominant, Goddess Furia. Mistress had given me a lollipop to wrap my glos...

Caught in Her Panties Ch. 03

by Knightofround on Sep 16, 2017
Transsexuals & Crossdressers

As we walk down the street I wink at some of the men walking past us. Alex and Mary giggle as they see the men checking me out. I even smile at the women too. "You are such a tease Krystal!" Alex says noticing some of the women blush as I check them out. We find a nice sidewalk coffee shop and take out seats. As I sit, I feel someone smack my ass. I jump a...

A Roleplay Gone Awry

by ronald81 on Sep 15, 2017
BDSM

All people within this story are over the age of 18. ***** For as long as I can remember, I have always been into cross-dressing as a young boy. Yet, I would hide these feelings deep down as I grew up. The following story is partly true, as much as I can remember. It all started when I was playing a roleplaying game featuring a text based game that was su...

Rubber Femdom World

by Rubberfoot on Oct 15, 2020
BDSM

Something strange was happening in the small college town of Little Gadsden. None could say what was causing it, but the one thing that was certain was that it started after the comet crashed near the town. Little Gadsden was a small place, of no more than a few hundred inhabitants, so the event was the most talked about thing for weeks, even though nothing...

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PARTYBOY and His Bitch Wife

by Goddess_Meanie on Mar 13, 2018
BDSM

I'm didn't take the time out to describe myself. I often skip over my features. They are both a gift and a curse. Young girl, very timid, secretive and shy. Early masturbator, enjoyer of porn and as my youth went about, and more and more aggressive, into my teen years. At that same time I found boys to be boring as hell, and always needing to be led. I had a...

A Whole New Me Ch. 02

by libertinaXx on Sep 12, 2017
Transsexuals & Crossdressers

I had just finished cleaning up in the bathroom. A spontaneous encounter with my best friend whilst wearing my girlfriend's thong had left me a bit of a mess and as for the thong... well I guess I'd need to find something new. Fully cleaned up, I ran naked into our bedroom and started looking through Lisa's drawers for a new pair of panties. I wasn't sure h...

Steph and Giulia Ch. 06: The Strapon

by BigHand32 on Sep 16, 2017
Fetish

Stephen felt embarrassed. How had he got himself into this? Wearing cutoffs and tights to school? He expected to be mocked and called names, by everyone. Maybe it was more awkward today... sometimes Stephen thought he caught someone looking, in the distance, but by the time they reached him, their head was turned away. Was it his imagination? Sometimes he th...

Motorcycle Anal Dyke

by magic_tantra on Sep 12, 2017
BDSM

I had a big smile on my face as I drove to the beach because my mistress finally paid some nasty attention to me. I tried to reminisce in my dirty mind the magic moments that just transpired. First I watched Mistress Sandra finish her wine kneeling patiently before her. Handing me the empty glass Sandra bent down, reached into my crotch grabbing my cock with...

Cuckold's Descent

by syncbush on Mar 27, 2020
Cheating Spouses

Thank you to those of you who have liked or taken the time to comment/message me. I really appreciate the feedback. Feel free to add additional chapters, suggest ideas or leave comments. It is great to get ffedback and encourages writers to continue developing the stories. And special thanks to the Admins for making this story of the week! Really appreciated...

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