Gaping Hole Stories

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Smart Fat Girls Choose Anal Sex

by Samuelx on Sep 14, 2017
Anal

My name is Diana Styles and I'm a strap-on addict and an avowed fetish fanatic. A five-foot-ten, kind of chubby and big-bottomed, blonde-haired and green-eyed Irishwoman of Southern origin living in the city of Brockton, Massachusetts. Forty years old and counting. By day, I am an accountant. I am the CEO of Styles & Madison, a multi-million-dollar accountin...

Anal Invasion Ch. 03

by MTL17 on Sep 18, 2017
Celebrities & Fan Fiction

SMACK! Trish Stratus cried out in pain as the sound of her big ass being smacked echoed throughout what she had thought was an empty corridor. Thinking some cocky WWF superstar or backstage attendant had stepped out of line Trish turned around and prepared to slap whoever had smacked her booty, but all the fight drained from her body and her ass hole pucke...

Mickie's Mine Ch. 03

by MTL17 on Sep 11, 2017
Celebrities & Fan Fiction

After she and Melina had firmly strapped on their dildos Trish turned to her ex-girlfriend and said, "Mickie, get down on your knees here in front of me." Nodding her head softly in submission Mickie crawled on all fours to the bottom of the bed, got down onto the floor and positioned herself on her knees in front of her former lover. "Do you remember this...

Safari of Depravity Ch. 02

by scatwoman on Sep 13, 2017
Fetish

by Scatwoman (credit to MercySlayer for inspiration) Part 2: "Initiation" The pace was very quick and shortly the group entered their camp with their captured prey. It was here that Dylan got his first look at the native women. They were just as dark as the men, and tall as well. 6 feet tall on average and muscular as well. The older women were quite...

Anal Etiquette Ch. 01: Politics as Usual

by CypherWest on Sep 15, 2017
Group Sex

Ashley and I were married upon her graduation from high school. By that time, I had finished up my degree and had a job as a staffer for a local politician lined up after my internship was done. The conditions for the marriage was simple: Ashley and I were to be married now and when Ashley's younger sister, Annie, graduated High School, we were to be married...

Irina's Lucky Day

by Indickative73 on Sep 1, 2017
Group Sex

I have already written about my wife Irina and her seduction of her cousin Nadia's boyfriend Charlie. If you missed it, l ought to outline what happened as a prelude to this meeting. It all started with Nadia complaining about the size of Charlie's cock and showing Irina the size of it. She couldn't stop thinking about it after that and even mentioned it to...

Before Chuck

by MTL17 on Sep 11, 2017
Celebrities & Fan Fiction

Author's note: This story is based on Chuck and takes place just before the series began. * Sarah Walker was currently face down, ass up and feeling extremely nervous. Well, she was actually feeling what felt like a thousand different things all at once, but nervousness was the most recognisable emotion, and rightfully so considering Carina was kneeling...

HLA: Hot Lesbian Anal Ch. 04

by MTL17 on Sep 11, 2017
Celebrities & Fan Fiction

Author's Note A special thank you to Vintage for his previous contribution to this series. *** Fans cheer loudly throughout the arena as the fireworks go off for the beginning of Thursday Night Smackdown. "Good evening ladies and gentlemen I'm Michael Cole and myself and my partner Tazz would like to welcome you to a very special episode of Smackdown."...

Science via Sex: Chemical Bonding

by on_the_quiet on Sep 15, 2017
Humor & Satire

Ever thought that chemistry was simply too hard or abstract to understand? Well, how about an explanation of a few major concepts using something everyone can understand: sex. Much of what happens at an atomic level can be summarised as atoms having sex in various positions with many interesting outcomes. A fundamental principle of chemistry, that many fin...

The Convention Slut Ch. 01

by NiteWriter on Sep 13, 2017
Group Sex

My plan was to help Nicolle become sluttier. She desperately wants to be the filthiest whore ever. So I'm taking her to a convention at a local hotel where she's going to be the after hours entertainment. But before even meeting the men, she becomes an anal slut for the two black valet parking attendants. In this chapter Nicolle shows them how talented she c...