Bdsm Sissy Stories

48,137 results
Orientation
Length
Source
Infinite Scroll

Set Up Ch. 01

by Sissy_Ashlee on Sep 15, 2017
Transsexuals & Crossdressers

This is my first attempt into writing an erotica story. This tale will contain themes of female domination, crossdressing, and eventually MM sex. If any of this is not you thing, please scroll on. Otherwise, please let me know how I did. ***** Since I was a teenager, I had been bicurious. Not really interested in men, but what is between their legs. My obs...

Simon Sissy Slave Ch. 04

by Timewarp10 on Aug 20, 2019
BDSM

Simon staggered in for work the day after the slave auction, his body stiff and sore. Mr Berne and the others in the post room were shocked to see the sissy's bruised and lacerated buttocks. Barry's stiff cock betrayed his feelings; whipping and torture excited him. His sadistic nature relished the thought of thrashing Sissy senseless. Sissy was his fuck t...

Spanking Night Ch. 04

by Angelscuck on Sep 14, 2017
BDSM

I slowly rolled over to allow my wife access to my bare bottom. I was still in shock, my mind reeling from what she had just confessed to me. This was no mind game. I had the proof-positive taste still lingering in my mouth. Smack. Suddenly the sound and sting of the cane against my skin brought me back to reality. It hurt like hell! I didn't cry out but I...

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...

Hero Losing Himself

by lol159 on Jan 8, 2019
BDSM

Since Mark was a kid he dreamt about being a hero. He wanted to be someone who did the job on his own. He wanted to be the macho just like his hero The Jaguar Man. He was the proudest man about himself. Having been grown up in an orphanage after his parents were both killed by a robber, he knew best that no kid deserved to lose his family. That's the reason...

My Sissification Ch. 03

by sissy171 on Aug 31, 2020
BDSM

Spring weather coaxed skimpy Summer attire. Melissa was 2" taller than me, so when we ventured out, I easily passed as female. I had learned all the subtleties and intricacies of face make-up, and my nails were always polished. I was "checked-out" by men everywhere. My legs and ass were muscular, shapely, and sexy; few women could compete from the waist dow...

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. "...

Sissy Girl Forever Pt. 03

by sissymissyct on Sep 18, 2017
Transsexuals & Crossdressers

Sissygirl forever continued. Sara stood there laughing at me as Mistress explained how things would be for the near future. She told Miss Andrea that if I wished she could fill them in with the red right now if I wanted. But Mistress said no. She was looking forward to my rushing off to work at times forgetting to polish them. Or eating out with friends and...

Wife in Control Ch. 01

by wifetoy on Sep 25, 2017
BDSM

I originally posted this story almost two years ago, but lost the other parts of the story when my computer crashed. I am reposting this part and will be posting the other parts of the story over the next few weeks as I finish retyping them. While I may post some fictional stories in the future, all of the events in this one and the other parts to follow are...

A Dream Come True Ch. 01

by searic on Sep 17, 2017
BDSM

Arriving at the hotel you had selected after a not-unpleasant drive up, I had plenty of time to obey my instructions. Carefully unpacking, I hung up and put in drawers my few vanilla clothes and all the sissy things you had selected for me to bring. How relieved I was to find myself able to be prepared and in position in advance of the time you had set for...