Sissy Pee Stories

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Master and Four Subs

by totk6432 on Apr 17, 2018
Fetish

This is a fantasy written by myself for fun. It contains spanking, humiliation and fetish; if this bothers you please seek other authors. All characters are 25 years old or older. ======= The rule is simple: I ring the doorbell and let myself into Master Daddy's house. Susan, my 25 year old personal assistant, is with me. She is in charge of me at work. Sh...

Born to be a Cuckold

by W_MA_DWM on Sep 11, 2017
Fetish

This story starts off slow, however it does lead into some very explicit sexual scenes. So be patient -- it gets hotter. It all began over twenty years ago when I met Lizabeth, the girl who became my wife. I had no idea what Mother Nature's plan was for me in those early years. I did realize that I was different than the other boys and felt that I neve...

Lucas's Prom Night Ch. 02

by Lucas96 on Mar 23, 2020
Fetish

Author's Note: this story contains cuckolding, humiliation, homosexuality, and forced/non-consensual sex. *** After my prom night, my wish came true - I spent the rest of the school year receiving texts of pics and videos showing Jeff fucking one or both of the girls, and on lucky days he would invite me over to watch, even sometimes letting me suck his d...

My Week with Laurie

by robbie3 on Sep 14, 2017
Fetish

Laurie was a co-worker who had recently been appointed the training officer in our government agency. As such, she had acquired a nice private office, in which I found myself spending more and more time. We had always been friendly, but lately were exchanging comments of a more personal nature. I'd call it meaningless flirting. Laurie was a year or two young...

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...

Transition from Man to Lady

by nancyvasquez on Oct 10, 2017
Erotic Couplings

I was born male, but both physically and emotionally I was more female. I went out of my way to - just barely - avoid being regarded as a sissy by my peers growing up. But after I hit puberty I never really developed the physical characteristics associated with manliness. By age 18 I had reached my full height of 5',6", and was small boned and delicately bui...

Naruto vs Konohamaru

by Littleprincespanties1 on Apr 29, 2025

Naruto is at the training ground facing Konohamaru as they look at each other. Konohamaru grins are you sure you want another fight Naruto after all the other times that you lost and I completely humiliated you. Naruto goes bright red as thinks back to what humiliation he has gone through Konohamaru has stripped him to his underwear made him walk home in jus...

Humiliated by Wonder Woman

by littleerection on Sep 17, 2017
BDSM

So it's a nice day today. I decide to go outside to get some fresh air and go for a walk. I wanna soak in the early spring cool breeze. I find myself going through the woods. Eventually I end up near the end and I see her past the trees standing alone on the cliff: The one and only Wonder Woman, looking out over the town! I couldn't believe my eyes! I've alw...

Sissy Stretching for Princess T Pt. 02

by Subboi23 on May 12, 2020
Fetish

Once I get home, I practically run to my room. Sitting in the car has pressed my plug deep into my ass and now my running causes it to wiggle around while still deep inside me. "Home Princess," I text as soon as I close and lock the door to my room. I quickly peel all my clothes off except for my panties and get on my knees. My toy is retrieved from a draw...

Sissy Gets Punished

by MsMorrigan on Sep 16, 2017
BDSM

Once upon a time there was an overly eager sissy girl. This sissy girl loved her mistress. She loved her so much she tried to anticipate her every whim before she needed to even speak the words. One day the sissy girl was vacuuming, dusting and general cleaning. She was openly lamenting on how her overly large pathetic sissy clit was getting in her way. How...