Sissy Cheerleader Stories

12,762 results
Orientation
Length
Source
Infinite Scroll

Kate's Mom Comes To Visit Ch. 05

by Catytheghost on Sep 16, 2017
Transsexuals & Crossdressers

Part 5 A wedding to plan Carmen OK, dinner was a total surprise for me, that's for sure: Ally and Kate getting married, and Mary putting the fear of the Gods into Maggie. Now that really was a shocker, as Mary gets along with everyone. I even asked her about Lady Jenna using me for her pleasure, and she said, "Honey, you just please her and all will be goo...

A Sissy Saga Ch. 23

by Snurge on Sep 15, 2017
Novels and Novellas

Mrs Pardoe's heart pounded like steam-hammer as she made her way to her room. It had been such a long time since she'd had a young girl to herself, to take command of, to admire and to love, and she knew Mrs Amos's niece Lizzie was a real doll. On the way she passed the Joanna television-person ensconced with Gloria in the stair well of the third floor, bot...

Knowing Your Strength Pt. 02

by JimBob44 on Sep 13, 2017
NonHuman

Author's Note: Any and all persons engaging in any sexual activity are at least eighteen years of age. ***** Chapter 1 Angel Hart tittered as she felt Jason Breaux's eyes on her. Just before entering their home room, she turned and gave him a quick kiss on his lips. That little kiss would have resulted in the both of them being suspended for three days f...

Big U Pride Ch. 03: The Squad Forms

by latinarita4 on Jul 27, 2020
Transgender & Crossdressers

Remember to check on parts 1 and 2 before you read this! Also, please rate and review my stories! I love hearing feedback from readers! If you have suggestions, just send them right along! Maybe your suggestion will be featured in a future chapter... ________________ Most days at the campus health center were typically light affairs. Usually it's the rout...

My Toy Nancy Ch. 03

by NiceNastyMann on Sep 19, 2017
Fetish

I overhear Nancy ordering Mark around, telling him to make sure he has his car keys and wallet. She takes great delight in reminding him of the consequences if he embarrasses her in public. The two of them head out of the apartment and on the way to their shopping trip. After they're gone I get my phone and dial Marge, an old friend of mine. After a few rin...

You're Like a Little Boy at Times Ch. 04

by Myneed on Oct 11, 2017
Fetish

This is a femdom love story that will make most sense if the chapters are read in order. James is becoming helpless as Mel dominates him and molds him to her will. The characters don't seem to want to engage in safe sex, but in the real world we should. Enjoy. All characters are over 18 Chapter 4 I received a flyer in the mail. Nowdays it is unusual to...

Morning Glory

by dreadknots on Apr 25, 2018
Transsexuals & Crossdressers

Reviews for my last crossdress-y story were pretty good! Hurray! This one is a little more teasing in nature, but is ultimately pretty fuzzy. I am a sap. *** Hardcore Fitness was the classiest gloryhole in town. All the right people knew what went on behind the illusory front of a 24/7 gym, and the syndicate behind its operation paid off the right guys in...

Twenty-One More Questions

by silkstockingslover on Jan 1, 2019
Reviews & Essays

Summary: Jasmine responds to the most frequent questions asked by readers. Thanks to: Tex Beethoven, Wayne, and Robert for editing this essay. This isn't really a sequel, although it's a second part, as it addresses questions I didn't answer in 2017's Twenty Questions. 21 More Questions After 2017's 20 Questions, I received many more questions. I have n...

Tee and Gino Ch. 02

by gin0aki56 on Sep 16, 2017
Transsexuals & Crossdressers

The first time had been, well it had been a lark. I regularly look at the craigslist personals to see how much loneliness there is in the world at any given moment, admittedly it's not the most accurate of indicators, but that's the excuse that I use. I usually don't put too much stock into the fantasies or desperate pleas I find there, but hers had been dif...

Twelve Years

by Imoverit41 on Mar 17, 2020
Loving Wives

Twelve years had passed and I still can't get past her or our combined families betrayal. Trust! No bloody way! There is no forgiveness from me. No accept it, get over it and move on like they wanted. I knew it would take time, but I'd have my day! I've worked hard for the last twelve years after our divorce. I have lived like an impoverished monk to save e...