Cheerleader Bet Stories

69,749 results
Orientation
Length
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Infinite Scroll

Quest for Normal Pt. 01

by JimBob44 on Aug 6, 2019
First Time

*Author's Note: Any and all persons engaging in any sexual activity are at least eighteen years of age. Disclaimers: This story has been edited by myself, utilizing Microsoft Spell-check. You have been forewarned; expect to find mistakes. Also, if male or female bisexuality offends you, kindly hit your backspace key now. *.*.*.*.*.*.* "Eighteen years lon...

The House Party

by Lucas96 on Dec 25, 2019
Fetish

Disclaimer: this story contains cuckolding, humiliation, cross-dressing, and gay sex. *** Lucas and Daisy had been dating for about 3 months. They were both 18-year-old freshmen in college. All their friends said they made such a cute couple. They even kind of looked alike - both blonde, short, and pretty, both weighing barely more than 90 pounds. The only...

The Arrangment

by Iwroteathing on Mar 2, 2020
Exhibitionist & Voyeur

It had been two years since Christine Andrews first saw her name on a brass plaque in the New York offices of HNF investments. She had been in charge of a lucrative hedge fund portfolio for some time and, as she predicted when she first got the job, she was almost completely uninterested. Christine had actually made news when she was in college as a financi...

Born to Be Ch. 06

by DamienDeath20 on Mar 9, 2020
Transgender & Crossdressers

A.N. Here we are again with more Born To Be!! :D Thank you all for waiting for these things to be updated, plenty more chapters are on the way! The Following Contains: Big black lady fucking her little white boy up with a strap-on. Ever seen ultimate surrender? Expect that up ahead ;) Enjoy the chappyyyy! ***** For a long time, Ashley actually con...

Life's Changes Ch. 01

by Scribler on Sep 19, 2017
Fetish

What do you do when you find out that your husband of eight years wants something different? All I knew was that Bill. That's my husband and I still had active sex life. Sure our frequency had slowed a bit. But what couples doesn't. Bill was the love of my life. I would do anything for him and too him. Bill stands about five foot eight. He's not very muscula...

Flight of the Raven Pt. 01

by Demonnox on Sep 13, 2017
Sci-Fi & Fantasy

Hi there! This is my first story and as such any helpful advice, constructive criticism or positive feedback would be much appreciated. :) Anyway, onto the important part. This story will be posted under the 'Sci-Fi and Fantasy' section. However, that doesn't mean that it will not contain themes from other genres. So, if you feel you'll die if you read anyt...

Changing Partners

by YDB95 on Sep 16, 2017
Novels and Novellas

For the gang I worked with in the summer of '92. Thanks for getting my head on straight! Aunt Arlene would have been proud of Dan, he was sure of that somehow, as he realized he'd arrived just in time for the last dance of the evening. Heavenly shades of night were long since fallen as the opening strains of "Goodnight My Love" flooded the speakers. Dan w...

Three Agonizing Days

by TenthDoctor on Sep 11, 2017
Fetish

When she came down to greet me at the lobby of her dorm building, nobody -- not the security guards nor the other students nor the people passing by on the streets -- could have guessed what was going on. I was in a suit, she in a sexy (but not slinky) red dress that made the red in her hair pop. They'd have thought we were prepared for a classy night on the...

Like a Boss Ch. 04

by MTL17 on Sep 18, 2017
Celebrities & Fan Fiction

After her latest night with the first ever NXT women's champion Sasha Banks woke up with a sore, gaping ass hole and Paige nowhere to be found. She had been pissed off ever since, especially as she was forced to wait for hours for her ass to heal enough so that she could just stumble around, and in that time she'd have plenty of chances to plot her revenge a...

This Is My Ass Now Ch. 04

by MTL17 on Sep 18, 2017
Celebrities & Fan Fiction

Paige had been very tempted to just stay in AJ's little love nest until the next RAW, maybe longer, however she wasn't about to lose her job over this little feud, no matter how fun it was topping Kaitlyn and Beth. So after a very long night of kinky lesbian sex she and Emma hit the road, barely making the RAW taping. That was when the incredible high she...