Cheerleader Anal Stories

51,089 results
Orientation
Length
Source
Infinite Scroll

Cheerleader's Mom: A Power Shift

by silkstockingslover on Sep 25, 2017
Illustrated

Summary: Mom is caught on her daughter's bed and made a submissive. Note 1: Thanks to hfernandez1983 for doing the visuals for this story and potential multi-part series. Note 2: Thanks to Robert, goamz86, and Wayne for editing. Cheerleader's Mom: A Power Shift Michelle walked to the laundry, bored and annoyed. She was sick of her boring daily routine...

Fat Girl's Guide To Anal Sex

by Samuelx on Sep 16, 2017
Interracial Love

I scour the Internet looking for large women for discreet encounters. They are my very own personal fetish. Don't ask me why. The first time I laid eyes on a chubby gal who was completely naked, I was hooked. My date to the prom was a slim, beautiful cheerleader but the gal whom I truly wanted was a chubby chick who was cute in my eyes but unfortunately had...

How To Treat a Sexy BBW

by Samuelx on Sep 14, 2017
Anal

Sometimes, I wonder why we humans were put on this place, the forsaken hell known as planet Earth. It must have been a cosmic mistake. Someone somewhere screwed up big-time. How else could you explain how horrible things are in this world? There are so many idiots out here it's not even funny. People like me with little or no conscience are more than happy t...

RoadBull - The Beginning

by xavier8in on Aug 30, 2017
First Time

My first story. Constructive feedback welcome. ***** My journey starts like many other middle-aged men. Married for more than ten years. The passion started to cool. Still very much in love with my wife, but I wanted more. She wanted less. The last thing I would do is make her unhappy so prepared for a life of unfulfilled sexual desire. Total cliché. Then...

Messenger Girl

by Krystal0690 on Sep 16, 2017
Loving Wives

Part 1 - Cheerleaders on the Beach We hid behind clumps of tall grass along the bluffs overlooking the beach. The summer night was warm, nearly moonless and inviting. Cody spread a beach blanket. This wasn't the first time I'd had sex near the shoreline, but it had always been deserted. Tonight there were dozens of people wandering along the strand. It seem...

Amazon Woman Gets Anal Love

by Samuelx on Sep 16, 2017
Anal

Sometimes, I just got to get myself some solace. A respite from life's problems, you know? I was walking around the fields, being an unemployed farmer whose farm got taken in by some big industrial complex. Just a tall, heavyset Black man living in rural Georgia, circa 1970. My name is Jack Bradford. I was once a student at the University of Georgia. I playe...

Like a Pro

by AllForTwo on Sep 11, 2017
Erotic Couplings

"I want you to fuck my ass," my wife said. Splayed out in front of me, legs spread wide with my cock in her cunt, I was not going to argue. That said, I was in no hurry to comply. I arched my legs higher and yanked back on her feet to pull her ass further over the edge of the bed. Standing over such a tiny woman, moving her around was pretty easy. She was...

Don't Cum in Me; Cum On Me

by walterio on Jun 19, 2018
Mature

PRELUDE It was the first time that I had stayed overnight in my girlfriend's mother's bed. Lynnette was at a cheerleader camp for another week and her mother and I had wasted no time jumping in the sack for an incredible night of sex. I had told my parents that I was going to a party and would crash at a friend's house afterward. Lynnette's mother Sondra lo...

Steven and the Cheerleaders

by RedHairedandFriendly on Sep 12, 2017
Group Sex

Author's Note: This story came from the 500 word challenge I participated in, that was posted on the Author's Forum (the title was Carpooling Cheerleaders). Later, most all the stories were collected and turned into a submission here at Lit. under the name: Coming Together and titled Transportation Challenge. It is full of 500 word stories by many talented w...

Big Fat Cock: Dumb Cheerleader

by silkstockingslover on May 20, 2019
Erotic Couplings

Summary: BFC is used to dominate a hot blonde cheerleader. Note 1: This is dedicated to the real Jeni who told me about this BIG FAT COCK... although her story wasn't told in the first three stories and isn't in this one either. Note 2: This is the fourth part in a potentially lengthy story of one nerd's discovery of the power having a BIG, FAT COCK can ha...