Sissy Cheerleader Stories

12,762 results
Orientation
Length
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Infinite Scroll

Real Life: The RPG

by Katnaace on Nov 25, 2019
Fetish

Having logged in, you get to the biggest question of all - who are you going to play? It's not like this is a big deal. You can just create your character and be on your way.What's next? Danny Hopkins - Dude with a sister Lydia Onava - Widow waking up in an unknown place Claude Rogers - On his way to visit his Aunt Henry Wells - Protesting H20 What's next...

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A Tale of Two Bitches

by Lordheed on Sep 12, 2017
BDSM

"Game Over", a deep voice pronounced from the television. Johnny threw down the controller in frustration. 'Can't even win at video games, let alone anything else', he thought to himself in disgust, 'What a way to start winter break'. He'd been home now for 3 days; already missed campus, his dorm room, and the constant business of schoolwork that could keep...

Dark Impassions

by Dragant on May 3, 2018
Interracial

Josh Tylers was a good looking 19-year-old black male with a promising day ahead of him. He was leaving to go on a date with his girlfriend 20-year-old half-Asian bombshell college sophomore Jade Pond. Josh was pretty sure he was going to lose his virginity this time too. She invited him to her dorm room and even threw in some suggestive language to the text...

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A Sissy's New Daddy Ch. 04

by sissyneko on Sep 25, 2017
Transsexuals & Crossdressers

It was with great pleasure that I am finally able to upload chapter 4 of "A Sissy's New Daddy" I have spent the better part of a year working on this chapter. I was surprisingly hard to get down on paper. I want to thank all the readers that have taken a time to comment and rate the chapters of this story. It has meant a great deal to me and has at a few dar...

The Writer's Secret Ch. 07-08

by AnnMichelle on Sep 16, 2017
Transsexuals & Crossdressers

Synopsis: Loren had no idea what he was getting into when his agent suggested he write transvestite fiction. Nor did he realize how eagerly his wife Stephanie would embrace the idea of feminizing her husband. How far would they go? Chapter 7: Laura Buys Shoes. . . Lots of Shoes Loren rolled out of bed the following morning. He yawned. Despite having sex w...

Casey's Submissive Journey Pt. 14

by corduroysissy on Aug 7, 2018
Transsexuals & Crossdressers

"Come over here princess, it's time for you to be my husband's little fuck-bunny." The time had come. He obediently walked over and she instructed him to drape himself over the stacked pillows, then bury his face in the corduroy pants on the other pillow. He did, and between the pillows, the bedspread and Susan's pants his whole body was now rubbing agai...

Afro Stress Relief Ch. 05

by llts1970 on Aug 1, 2018
Transsexuals & Crossdressers

My alarm went off the next day, my mouth and asshole ached, it was going to be a long day I thought. I had put plenty of grease up my asshole just to ease the soreness but it still felt pretty stretched. I started to remember last night, I couldn't believe I'd taken Baba G's fat black penis in my mouth, or that I'd spoken to the police officer like that! I w...

Mistress Chronicles Ch. 04

by MistressMtoyou on Sep 25, 2017
Fetish

Background: The next three stories involve my only long-term on-line subject who I have named Nancy. This subject passed all of the tests I described in story two ("A Few Good Subs"), but before we were able to arrange an in-person session, he was offered a job in a town a great distance away, precluding any in-person meets. We agreed to continue training...

Sarah Goes to College Ch. 04

by Sarahcheer on Sep 19, 2017
BDSM

Chapter 4: Sarah before the Court Sarah was utterly beaten, and she knew it. Brian, her owner, had been keeping her locked in a cage at his dorm room for the last week, only letting her out to use the bathtub restroom and to fuck her pussy when he was in the mood. Otherwise, she had been left locked in the cage, forced to wear a VR helmet that had continual...

Dry Valley Ch. 20

by RedHairedandFriendly on Sep 18, 2017
Chain Stories

Finishing Touches Three days had gone by since the break-in and attack on Jessica and Bailey. The women had been moved to the Walker Ranch, much to Missus O's soft muttering. But she knew the ranch was the place the girls needed to be to recuperate, she was however out there every day just to ease the burden on her friend Sissy, though Sissy didn't find it...