Sissy Piss Stories

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Orientation
Length
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Infinite Scroll

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...

AliExpress and Sissy Downfall Pt. 07

by His_fag_wife on Apr 9, 2018
Transsexuals & Crossdressers

Please for goodness sake don't read this story if extreme use of submissive males by dominant males and dominant females offends you. This is pure fantasy and at the darker end of the spectrum of stories on Literotica, please do not read if this is not your sort of thing. Otherwise I hope you enjoy the spiral of depravity. ***** Charlie was alone in the ro...

From Her Ex-Boss to her Bitch Pt. 06

by His_fag_wife on Sep 25, 2017
Transsexuals & Crossdressers

Please do not read this story if fantasy is not your thing. This has scenes of outrageous levels of forced sissification, forced bi and gay scenes, watersports and general humiliation and degradation. It's just pure fantasy and includes some hypnosis. Some readers find these stories too full of fantasy, in which case please just don't read it. ***** It had...

The Training of Sissy Paula Ch. 5

by submissive~pet~ on Sep 14, 2017
Fetish

After the fuckings I had gotten from Max my asshole was so stretched, I had to wear diapers all the time. Mistress Carolyn used this to her advantage. She had a few men that liked sissy babies. The men would bring me all sorts of little sissy clothes. Dress me up and have me nurse their cocks as if they were bottles of milk. One day a new man showed up, he w...

AliExpress and Sissy Downfall Pt. 06

by His_fag_wife on Mar 6, 2018
Transsexuals & Crossdressers

"Ok, now you've been fed, back in the chair and Candice will get your make up done, so that you are as pretty as you can be when you return to your Mistress and Master." "Get all that mess cleaned off her face please Candice and start making her up to look pretty." "Yes Miss Bell." Charlie got back in the chair and Candice prepared to make her look as pre...

Tales of Sub Asian Sissy Ch. 02

by subASIANsissyJADE on Apr 9, 2019
Transgender & Crossdressers

Once the door closed and I heard the deadbolt latch, I panicked. How on earth could I walk to my car in my current state! I stood there, my heart racing, in my black fishnet thigh highs, no panties, a glass butt plug with a big pink fluffy tail firmly lodged in my tight asspussy, my black lace bra, and my face and chin and neck covered in drying cum. I des...

Pay for Pleasure - Prequel

by Pleasure_the_slut on Sep 16, 2017
Transsexuals & Crossdressers

I had written about how Sandy turned me into a $50 whore before writing about how I got to that point with her. I was cruising an online posting for sex one Thursday evening and I came across a posting for TV looking for big cock. Well that got my attention, I'm 8" and very thick. So, I shot a reply right away. Not a minute later Sandy and I started chatti...

Megan's Bitch

by magicrub on Sep 14, 2017
Fetish

"Why are your clothes still on?" demanded Megan as she smacked her bitch across the face. "I'm sorry Mistress..." bitch replied before being sharply smacked again. "I did not give you permission to speak bitch!" replied Megan. "Besides, a Mistress does not have a cock like this one! Does she slut?" "No Mistr..err Master?" replied the bitch, starring at t...

The Prostate Exam Pt. 02

by His_fag_wife on Sep 18, 2017
Transsexuals & Crossdressers

It had all started with a routine visit to his Doc for a simple prostate exam. After he'd given away his submissive tendencies by pushing back against her finger, she'd given him a good hard anal fingering and then he'd revealed the true depths of submissive tendencies, to Dr Megan Sutton, or Miss Megan as he'd begin to know her. She then persuaded him to...

AliExpress and Sissy Downfall Pt. 05

by His_fag_wife on Feb 6, 2018
Transsexuals & Crossdressers

Charlie was deep in it now, being assessed by Miss Bell the beautician before she started work on removing all of Charlies hair below her soon to be plucked eye line. Candice the young pretty petite receptionist was also looking on to deepen Charlies humiliation. "Miss Bell, I'm really tight, but even my little pussy couldn't be satisfied by that little cli...