Sissy Cheerleader Stories

12,762 results
Orientation
Length
Source
Infinite Scroll

My Sissy Bucket List

by _pdy_ on Apr 3, 2019
Transgender & Crossdressers

Just want to open up this piece with a little apology for my hiatus from continuing to document my time serving J. Life has just been so busy, and it's tough to find some time to write. Anyway, as you can probably clearly tell by the title of this piece, it is not a part of the Panty Boy Diaries series that I've previously started, and you do not have to hav...

How Low Can You Go?

by Compliant1 on Sep 16, 2017
Transsexuals & Crossdressers

Be careful what you wish for; that's a popular phrase in these Literotica stories. I found out the hard way the import of this message. I have always had a submissive streak a mile wide, but in my twenty-eight years I'd never experienced the feeling of completely surrendering to another person. With the Internet and its free personals web sites, I decided t...

My Girlfriend's Sister is Nasty Too

by Dr_AWES0ME on Oct 6, 2020
Fetish

Editor's note: this story contains scenes of incest or incest content. ***** Believe it or not this is actually based on a true story. The majority of this story is 100% true, some elements were slightly embellished, some were part of a vivid dream, and some parts (names for example) were completely fabricated. Although I have written for many years and ho...

The Writer's Secret Ch. 01-02

by AnnMichelle on Sep 13, 2017
Transsexuals & Crossdressers

Hi everybody! This is one of the many stories I've written over the years. I've decided to clean them up (read: edit the heck out of them) and start sharing them. This one has some light-femdom, a pretty willing husband, and a few fun surprises. Enjoy! * Loren had no idea what he was getting into when his agent suggested he write transvestite fiction. Nor...

My Cuckold Story Pt. 02

by ohsubmale on Sep 14, 2020
Transgender & Crossdressers

Wife Plants Her Ownership Pole - It's been a little while since I last shared about my experiences, so I am sharing my second experience I believe worth sharing in my deep dive into the submissive cuckold I have become. This is based on my real-life experiences, so please keep that in mind if it doesn't tick off all of your fantasies at once... I know our li...

Summer of Discovery Ch. 02

by DASTONE on Sep 16, 2017
BDSM

From Ch. 1 - Nina furiously tried to swallow it all, moaning as the torrent of hot cum filled her mouth. She couldn't swallow fast enough and cum started leaking out of her mouth and down her chin. Her eyes closed as she felt it; she felt so naughty, so dirty, like a filthy slut, begging to be covered in cum. And she felt pleasure. Intense pleasure as she...

Just Across the Hall Pt. 05

by EROTICbearscribe on Aug 6, 2019
Transgender & Crossdressers

Chapter Six KYLIE The next months were truly magical. True to his words, Lonnie didn't try to turn me into a girl. He celebrated the panty-boy I was. I moved in with him and we began our new life together. The insurance settlement from the fire allowed me to quit my job and stay home and take care of all the cleaning and cooking and...other things....

House Rules Ch. 09

by EROTICbearscribe on Jan 22, 2020
Transgender & Crossdressers

AUTHOR'S NOTE: This story contains characters and references to events in two previous stories I have written: Just Across The Hall and PIXIE: Sissy Stripper. It is not necessary to have read these two story chains. This chapter of House Rules could stand on its own for entertainment purposes. If, however you want context, please read the other two stories f...

Twenty Questions

by silkstockingslover on Jan 7, 2018
Reviews & Essays

Summary: Jasmine responds to most common questions asked by readers. Thanks to: Tex Beethoven, thor_ph, Robert, and Wayne for editing. 20 Questions I get asked a lot of questions about myself and my writing. There was even an article by Bob_Aganoush called Literotica Authors 02: silkstockingslover. This makes me think I should go into more detail. So her...

Candi's Conversion Ch. 04

by CandiCumminz on Oct 24, 2018
Transgender & Crossdressers

It was early afternoon when we pulled up at the mall. Mistress Luna had me drape myself sluttily over her car while she took some photos for my Instagram. I was still dressed as a sissy bimbo doll, having been styled by Crystal, a much more experienced sissy in servitude to another dominant, Goddess Furia. Mistress had given me a lollipop to wrap my glos...