Pimped Out Sissy Stories

353,644 results
Orientation
Length
Source
Infinite Scroll

Freaky Funland Resort

by DickThePimp on Apr 9, 2019
Celebrities & Fan Fiction

WARNING : TWISTED DEPRAVED PERVERTED HORNY ASS SLEAZY FREAKY AS FUCK SEX PARODY... IT AIN'T REAL... BUT IT SURE AS HELL IS DIRTY AS SHIT THIS IS MY HORNIEST... FREAKIEST... AND MOST PERVERTED FUCK FILLED FUCKFEST STORY YET... THERE ARE A BUNCH OF CELEBS IN THIS... IT'S ABOUT FREAKY FUNLAND RESORT... ME AND MY FUCKED UP HORNY ASS FAMILY AND CREW OPEN UP THE...

Boasting, Next Morning

by CrazyDaveTrucker60 on Feb 12, 2019
Group Sex

Authors Note: It's just a crazy fantasy. Any resemblance to reality means you need psychiatric help badly. Neurotics build castles in the sky. Psychotics live in them. Psychiatrists collect the rent. Have a great day, don't forget to take your meds! Nobody under eighteen years old. Etc. Etc. Be kind in your comments please. I'm low on happy pills. ***** Ba...

Nancy and Her Boss Ch. 03

by MidniteSpanker on Sep 19, 2017
BDSM

Part 3 – The Weekend. The initial stories in this series Nancy Remembers Chap. 1 Nancy Remembers Chap. 2 Nancy Remembers Chap. 3 Other stories continuing in this series Nancy and her Boss Part 1 Nancy and her Boss Part 2 Nancy and her Boss Part 3 - The Weekend Nancy and her Boss Part 4 - More Weekend Then the following are separate but related stories...

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...

The Prostate Exam Pt. 05

by His_fag_wife on Sep 18, 2017
Transsexuals & Crossdressers

Since giving himself away in his first prostate exam to his Dominant Doctor Megan he had been prepared for use by an old Master, now Sissy was on her way to be used. Sissy was breathless as she read the text from Master V, she looked around the small airport to make sure she didn't know anyone, whilst she was looking at her texts. Thank goodness she didn't....

Ultimate Sissy Weekend Ch. 01

by SissyTwinkleToes on Dec 24, 2019
Transgender & Crossdressers

Dressed head to twinkle toes in beautiful baby pink, Sissy Susie nervously waits for her friend to arrive and the most humiliating weekend of her life to begin. She winces as her teeny clitty squirms in its pink prison, a chastity cage that's been on for four frustrating weeks. Her cage is safely tucked away in her pink ruffly panties, covered in sweet littl...

Further Training as Sissy Lesbian

by maturesubmale_for_F on Apr 22, 2020
Transgender & Crossdressers

Dear readers, This is a continuation of my story 'Miss Johnstone's Lesbian Sissy Slut' and I sincerely recommend reading that story first as it provides background for this one. Enjoy and please take time to give me some feedback! Theo 3. Intermission: Further training Following the loss of my sissy virginity just after I had turned eighteen years old,...

Claire's New Start

by Sissyhalo on Mar 21, 2018
Transsexuals & Crossdressers

There's the thick taste of cum in my mouth and my bum has that feeling of being fucked...filled...made love to and last night replays in my sleep along with everything that has found a home in my head. ...Stop lying, start loving that cock inside you. ...You've never been man enough but you can be sissy enough. ...Worship cock like a good sissy girl. ......

Another Submissive Slut Ch. 11

by Stillherer on Sep 19, 2017
Transsexuals & Crossdressers

My land lady's knowing look held me transfixed. Quietly Mrs. Lehrer purred, "What are you?" A spasm of trembling shook my body before I could mew out, "I am a sub sissy slut, Mrs. Lehrer." "Hemmmmm," She hummed, "And what else are you slut?" Her voice was quiet, soothing, inquiring. "I am a wanton cum whore, Mrs. Lehrer," I admitted, blushing at such an a...

Mistress Barbara Calls Ch. 01

by goamz86 on Sep 19, 2017
BDSM

Letter to the reader: This is a story of female domination of a submissive couple. It includes the man sucking dildos and taking thinks up the ass. If this is not your cup-o-tea, please find another story. Don't waste your time and mine reading it and making comments about me being a fagot or other asinine remarks, I will just delete them. Constructive com...