Spanked Sissy Stories

24,820 results
Orientation
Length
Source
Infinite Scroll

First Time Sissy Maid

by bart2077 on Sep 13, 2017
Transsexuals & Crossdressers

I had been fantasizing for many years about serving a dominant Mistress, watching lots of movies online, and generally lusting over the doms I saw posting ads. At the age of 28 I finally found the courage to answer a rather intriguing post by an older woman and her trans partner who were looking for a sissy maid for ongoing service. I answered the ad, includ...

BWC for Black Male Sissy

by Samuelx on Sep 12, 2018
Transsexuals & Crossdressers

Meet Bass, which is short for Bashir Malong, a six-foot-seven, dark-skinned and ruggedly handsome man originally from the nation of South Sudan. Bashir is definitely more than he seems, and that's just the tip of the iceberg. A lot of people, upon meeting the tall, handsome brother with the deep voice, wonder if he's some sort of professional athlete, and Ba...

Samantha's Panty Boy Ch.02

by PinkPantysBoy on Sep 13, 2017
Fetish

Special thanks to Angel Love for editing. Samantha opened the front door and slammed it hard so Jack would know she was home. He had drifted off to sleep with his pink panty still on and her panty crotch on his face. He heard the door shut and immediately got up. He heard her coming up the stairs and did not have time to change back into his own underwear s...

Black Sissy For White Queen

by Samuelx on Sep 16, 2017
Interracial Love

I feel so damn great as I slide my strap-on dildo deep inside Ramon Jones. The six-foot-tall, skinny Black guy looks absolutely gorgeous in a bright pink dress, white pantyhose and high-heeled red shoes. His face is perfectly made up, rouged and his makeup and lipstick are applied nicely. The fuzzy black wig he's wearing only adds to his decidedly not so mas...

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...

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...

Mistress's Party Entertainment

by sissyapril on Sep 15, 2017
Transsexuals & Crossdressers

My Mistress was entertaining her sister Lady Brandi and her friend Lady Alexis in the living room and watching a Mistress dominate and humiliate a couple of her sissy slut males on DVD. The ladies were drinking wine as I was attending to the dishes after serving them dinner. I was wearing a French maid's uniform with black patent leather pumps and fishnet st...

A Sissy and His Master's Hand

by keptsissy on Aug 8, 2018
Fetish

AUTHOR'S NOTE: No character in this story is under the legal age of consent. They are all 21 years of age or older. No sex act in this story takes place other than between two CONSENTING adults. No character in this story does anything against their will or is seriously hurt, permanently physically harmed, abused without prior consent, maimed or killed. Ever...

Property of the Master Ch. 02

by BrightTightandWhite on Sep 26, 2017
Transsexuals & Crossdressers

"Wakey wakey sleepy head." The sound of curtains being drawn open was accompanied by a blinding light as my bleary eyes blinked open. "Wha... What? Huh? Hello?" I struggled to come up with coherent words as my brain wasn't fully awake yet. "Good morning Rosie, I hope you slept well," said the same voice as before. "Umm... Yes. Who are you?" I asked. "My...

Sissy Fluffs an Orgy

by yvetteinpanties on Sep 25, 2018
Transsexuals & Crossdressers

For years, I would seek out a new sex partner every six months or so. However, over the last year, I have become insatiable for cock. My male sex drive leaves me wanting it all the time, and, as a sissy, I don't need an erection to have a good time anymore. I can be a sissy slut whenever the opportunity arrives. Last night I found a new group on a social n...