Sissy Cheerleader Stories

12,762 results
Orientation
Length
Source
Infinite Scroll

Interracial Domination Duo

by AfroerotiK on Sep 17, 2017
BDSM

Andre West fidgeted in his car seat. "OK," he whispered into his watch, like it was a spy gadget from a James Bond movie, "the time is 17:30 hours and I've been surveilling the unknown address for two hours with no sign of any movement other than the mailman leaving a package." Did it matter that he didn't have a smart watch recording him, that his watch was...

Bayonetta's Abuse Ch. 05

by ChainedToAKeyboard on Sep 13, 2017
BDSM

Can deep love abide between Mistress and slave? Or will it always be a matter of sex and punishment? Only a trial by fire will tell. Bayonetta's Abuse V - Flames Of Passion James was deep asleep as the rain pitter-pattered against the large, arched window opposite the bed. Only the smallest amount of light crept into the large bedroom, the grey, cloud-fil...

Recruiting of a Sissy Maid Ch. 06

by Sissy_Chantel on Oct 11, 2017
Transsexuals & Crossdressers

Chapter Six: Pornography Anyone? Master Reggie knocks at Chantel's room door. Chantel replies, "Come in." Reggie comes in and says, "You packed and ready to go Chantel?" Chantel says, "Yes Master Reggie. I have a suitcase packed with outfits for the movie and a change of clothes besides what I am wearing." Chantel wears a pink t-shirt, black skinny jeans...

Pillow Talk Ch. 04

by MicheleNylons on Sep 10, 2018
Transsexuals & Crossdressers

Chapter Four - Goomah Michelle Clooney felt Frank Caputo's erection prodding at her backside; it slid inside her panties and probed her buttocks until it found her sphincter. Frankie held her hips and slowly pushed himself deep inside her. Michelle relaxed her sphincter as she had learned to do to accommodate the girth of his large cock in her anus. There w...

A Weekend with Master Jim Day 01

by Ms_Allison on Sep 17, 2018
BDSM

Through my many adventures I have been with some amazing Dominants. While I found Master Jim to be rather arrogant at first I found out that there was far more to him than just that. So very much more. I hope you enjoy it. ~~~~~~~~~~~~~~~~~~ As amber and I approached our little airport I could see her getting sadder. It was bad enough that I would disappe...

Casey's Submissive Journey Pt. 10

by corduroysissy on Jul 17, 2018
Transsexuals & Crossdressers

Mistress Dorothy was rubbing her husband's bulge affectionately. "Julian honey, Casey was sniffing your pissy pants while you were doing your chores, and quite frankly hubby, I think he liked it. Maybe in the future I'll borrow him from his wife and make him be your bathroom bitch, would you like that dear?" "Yes Mistress very much. Can I be the boss of hi...

Sausages for the Slave Ch. 03

by dyetied on Jul 17, 2018
BDSM

And so the day dawned; the day of my big punishment. The putative cause was the minor misdemeanour of ejaculating a lot sooner than my wife expected me to. The real cause was that she lost a bet on account of it. That was major. She's a competitive, alpha type, my wife: doesn't like to lose at anything. So because I had failed to perform to her expectations...

The Teasing Air Hostess Ch. 05

by footslave85 on Dec 29, 2017
Fetish

The week after my Goddess gave me the chastity cage was a very strange one, I would get home from work and put it on, then spend the evening trying to go about normal things and not have any naughty thoughts. It was really difficult at first, every time I moved and felt the cage in my pants it made me instantly think of my Goddess and I started to get arouse...

The English Ranch Pt. 01 Ch. 06

by slave_william on Sep 19, 2017
BDSM

(Warning –this and later chapters describe William's participation in Pony play and describes heavy BDSM and pain scenes which may not be enjoyed by all readers. Do Not Read if you cannot handle this type of fantasy and please remember, it is fantasy. If you do not enjoy this story or any of my writings, I'm certain that there are thousands of other stories...

The Waitress Ch. 10

by goldsssnake on Sep 19, 2017
BDSM

You cannot use this story for any commercial purpose, and you cannot publish it in any website other than Literotica. Respect original writing. Thanks. ******* I dedicate this story to Connie the Hot Cunt, and its conclusion to miss X, there in Alabama. Thanks very much to all the readers that heartily agreed with me in my points of view that I expressed...