Sissy Cheerleader Stories

12,762 results
Orientation
Length
Source
Infinite Scroll

Casey's Submissive Journey Pt. 06

by corduroysissy on Feb 7, 2018
Transsexuals & Crossdressers

Homo Hubby Night – Part Two Note: In this continuing saga, Casey (Debbie) & Jamie (Angie) are closet crossdressers who are submissive to their wives Karen & Audrey (respectively), however in this section of the story there is no cross-dressing. Their wives are humiliating them by making the boys put on a homosexual sex show for their amusement. *...

Futanari Academy Ch. 08

by TheOrcKing on Jun 5, 2019
Transgender & Crossdressers

(All characters participating in sexual activity are age 18 or over.) This chapter is a repost, it has been edited and has undergone very minor rewrites for style and flow. Nothing in the story has been changed. ***** "Pull the lead out of your ass Surbrina!" Miss Angeli barked, blowing her whistle. "You're a Nazi, coach!" Surbrina whined as she moved th...

Kasey's Confession Ch. 10

by KaseyLegs on Sep 14, 2017
Transsexuals & Crossdressers

I woke up the next morning in my new bedroom. I was wrapped in pink sheets topped with a Tinkerbelle themed comforter. On the walls were posters of gorgeous men, shirtless and displayed their well-muscled and oiled upper bodies. I barely remembered setting up the room with the help of Nancy and Mr. Smith after the party ended, but there it all was, and while...

The Awful Minute

by clinton09 on Sep 15, 2017
Loving Wives

[©2010 BY CLINTON09; ALL CHARACTERS OVER THE AGE OF 18; NO EVENTS DESCRIBED ARE TRUE] [Warning: this story contains cuckolding, male humiliation, suicide, sex, violence, golden showers, parody, and any other plot device I could think of. It is the ultimate dark vision and is intended as such. All events are presented with the subtlety of a ball peen hammer....

Jobe, Cross Dresser Extraordinaire

by YANKEE DAN on Sep 16, 2017
Transsexuals & Crossdressers

I used to be pretty bored. Not last week, or a mouth ago, but the last twenty five years. Life has just always seemed to be… dull. But lately, things have been looking up. I grew my hair out recently, I've got black hair, I'm tall and skinny, perfect body to pretend you're a girl in. I'm the public relations man for a large company. Most of my work is done...

A Sissy's Date Night

by nadia603000 on Oct 19, 2020
BDSM

Author's Note: Mistress Pepper and Sophie are "anonymized" versions of me and my slave-girl. The real me. All of my stories are (or should I say will be) my memories of a session with a sub. Thus, they are true stories. Only in this version details have been changed to protect the sub. I do live in Mobile about 10 months of the year (the remaining two I spe...

Marriage Transformation Ch. 10

by jealouscuck on Feb 13, 2018
Fetish

After their night of sex with Tim, Chris and Elizabeth had a light lunch and retired to the pool. They had one more night before they would go home on Sunday. At first, they just relaxed in the sun. Later, they noticed Tim come into the pool area with some of his bachelor party friends. Chris noticed that most of the guys were stealing glances at them. They...

Dan's dreams come True Ch. 01

by JenniferTaylorTV on Jan 20, 2020
Transgender & Crossdressers

Dan felt the familiar tingle as he walked down the street. First there was the pub, then the little cafe with its pretty tables and the stationery store. And then the green door. The one he'd walked through many times but always got the wonderful, knot of expectation in his stomach. Looking straight ahead, he pushed it open and walked through. Once inside,...

Straight Crossdresser

by silkstockingslover on Oct 22, 2019
Transgender & Crossdressers

Summary: Guy dresses as a girl on Halloween and ends up performing as one. Note: This is a Halloween 2019 Contest story, so please vote. Thanks to: Tex Beethoven, and Robert for editing. * As I draped the sheer pantyhose onto my legs to finish off my Halloween costume, preparing for a night of cock sucking and bottoming at the annual Halloween men's onl...

Black Man One Ch. 02

by Weak_White_Wimp on Sep 19, 2017
Interracial Love

My military career was challenging. The workouts were exhausting but somehow I got through it. For a period of time I even learned the sport of boxing, which was basically pushed upon many of us by our staff sergeant. I was 28 at the time. Staff Sergeant Williams seemed to have a way to persuade us to do anything. He was really tough on us. Generally, he "pi...