Sissy Cheerleader Stories

12,762 results
Orientation
Length
Source
Infinite Scroll

Jamie Becomes Herself Ch. 01

by heavyandhorny on Sep 14, 2020
Transgender & Crossdressers

It was almost midnight and my computer was flashing bright images in front of my eyes. The screen showed cocks, and porn stars and suggestive words overlaid together to make me fall into a sort of trance. The hypno continued to play and my little cock grew in my hand, my balls were contained by the panties I had pushed down. I rubbed my 4 inch cock harder an...

Letter from Iddlesleigh Harbor

by justincbenedict on Sep 9, 2019
BDSM

Dear Shoeblossom-- I am a townie bitch from a crappy beach village, and I snared a rich little piglet, and I just recorded one of our more pitiful conversations! Stephanie "Stalki" Sendack "I don't think you did that badly, Crates. You actually seem to howl more when I cane you, you know." "Stalki, it feels so marvelous when you stroke...oh it's so nice...

I Get Bullied, My Mom Gets Fucked

by I_Love_MILF on Jan 8, 2019
Mature

My mom, Christina, had been at war with one of her students, Zack, the starting quarterback on the university's football team. The meathead, who was left behind a year, had no trouble getting girls his age...hell, I think half the campus wanted him. Guys were forced to be his friend because if you weren't his friend, he was your bully. Christina was the law...

The List Ch. 03

by handsomeyetnice on Sep 25, 2017
First Time

I showed up at school the next morning, and for the first time I felt good about myself. My friend Mindy, once just my "buddy" now desperately wanted to be my "fuck buddy". On top of that, for the first time I started to think that maybe I actually could hook up with Amy, the girl I dreamed about. Life was good, until I got a sudden reminder that my world h...

Mike the Gang Bang Bitch

by sissyneko on Mar 17, 2020
Transgender & Crossdressers

Standing in the bathroom wearing just his little pink bikini panties and stockings, Mikes gaze was transfixed. Not on the panties, the usual draw of his lust, or even his white thigh high stockings with their little pink bows at the top. None of that drew his attention, it was the bathroom itself, it was run down, dingy and in the worse part of town. But non...

Heidi’s Submission

by TimT1972 on Sep 19, 2017
Transsexuals & Crossdressers

Eighteen year olds are the same the world over. The handsome, tough and sporty are nearly always the most popular. Adam was none of these, he was rather effeminate, of slight build and definitely no sportsman. As such, he never had that many friends. His home life wasn't much better; his father was dead, he had no siblings and his mother worked every hour Go...

Big U Pride Ch. 01: The Beginning

by latinarita4 on Jun 2, 2020
Transgender & Crossdressers

The college bus meandered down the winding side streets, making its way at a patient pace down the road. Along the side of the bus was emblazoned in big letters, "Big U Football" with the college mascot printed on it, a Rooster with arms in boxing gloves raised and ready for fisticuffs. Another banner tagged on the side of the bus by the mascot were the word...

Julie Gets Her Name

by juliegomez on Sep 16, 2017
Transsexuals & Crossdressers

My battered butt hole throbbed and pulsated in and out, oozing a steady stream of white slippery cum into a pool on the table top. How could I have been so foolish? xxx It had been a nice quiet Saturday night. The jocks that I shared the dorm with had gone out to watch our team play a home game and I had had the place to myself for a few hours. I had down...

March Madness Ch. 09a

by jbirdman on Sep 13, 2017
Transsexuals & Crossdressers

This story is not intended for children and if you are not old enough to read sexually explicit material, go away. This story features some elements of female domination (femdom), teasing & denial, chastity training, mild bondage, creampies, cuckolding cross-dressing and a few other fantasies of mine. I hope you find it entertaining, but if you might be offe...

His Sissy Bitch Ch. 07

by keptsissy on Sep 26, 2017
Transsexuals & Crossdressers

He makes sure they all get a good look at my rear end. He pinned my skirt up in the back, large safety pin holds my skirt up at the top. It's a large baby diaper safety pin, one that women used in the 1950s, pink plastic shows at the top. Kind of cute, the pink plastic matches my ear rings. I could just take my skirt off but he says it's way sexier this way,...