Holes Stories

36,815 results
Orientation
Length
Source
Infinite Scroll

Hot Chicks... Hot Sex Ch. 01

by DickThePimp on Oct 12, 2020
Celebrities & Fan Fiction

A multi part setup story for the future Slutty Living story. "Thank you for being on the show." "My pleasure. I've been a big fan of yours for a long time. Hoda too." "Awww... you're so sweet. I guess we'll find out just how BIG of a fan you really are... now won't we?" "Ha ha ha. Yeah. I guess we will." My grandmother Kathie Lee (Kathie Lee Gifford) is...

Home for Summer Break Pt. 03

by Actual_Mom on Oct 12, 2020
First Time

- - - This picks up where Part 2 left off - - - At dinner that night, Bob thought about Jan's statement about a girlfriend or wife. It answered one of the thoughts he had in the back of his head about his dad. Bob's mom asked "Is everything alright, Bob?" "Sure." Bob's dad added "You haven't said two words all day. What's the matter?" Bob knew he needed...

Size Queen Prostitute

by MrHackerMan on Dec 14, 2020
First Time

"Emily, you like big guys right?" I pulled the penis out of my mouth with a wet pop. "Of course. Who doesn't? But I'm kinda with a client right now, Harper." My client groaned. I felt a weak hand on the back of my head trying to push me back down towards the hard penis before me. I ignored it. I was lying face down on the bed, my smooth, shapely legs splay...

The Next Step

by Robert_Anthony on Sep 25, 2017
BDSM

Matt sat on the edge of the bed looking down at the steel tube which encased his cock. He'd waited so long for this moment, but still he was tremendously nervous. As he looked down he caught sight of his face, reflected in the highly polished surface of the chastity device. Could he really go through with this? He steeled himself and pushed the small padlock...

'Extra' Coaching

by bbw4youngercocks1 on Sep 25, 2017
Anal

Darcy stared at herself in the mirror with disgust. Despite the one-piece, well-fitting bathing suit she wore, she was still critical of herself. She was still a very attractive woman in her mid-forties, but a little curvier then her petite frame suggested. She stood 5' 3" and had what some would say a little extra baggage around her hips and thighs. Thoug...

Flashing at Shoe Stores

by Liz_ny on Sep 25, 2017
Exhibitionist & Voyeur

When I was a bit younger one of the ways I like to flash men was at a shoe store. The salesmen was the only one who got to see but it was exciting. I got dressed in a front button down skirt, garter belt, stockings, and no panties. Sometimes I also wear a dark colored see-thru blouse, no bra and a button down sweater, which I open when I went into the store....

The Trouble with Roommates Ch. 02

by KaylaG on Sep 18, 2017
Transsexuals & Crossdressers

As much as Nick hated to admit it, he was getting used to the feeling of his smooth skin. For the past month his roommate Brian had been making him shave twice a week as well as wear mascara and lip gloss that he was made to reapply whenever his lips lost their baby-pink sheen. He wasn't going to miss it, though, that was for sure. He'd been doing well with...

Her Anal Punishment

by LainyGee on Sep 25, 2017
BDSM

He was a man who liked routine, so his punishment scenarios rarely changed. She'd kneel at the bottom edge of the bed, face down in a pillow, ass in the air, legs spread wide. It was humbling, this holes-exposed-for-punishment position, and just being in it could cause her tears to flow. He didn't mind tears, or crying, or begging -- expected them, in fact -...

Bree Impaled

by CandyBree83 on Sep 25, 2017
Toys & Masturbation

She awoke from her dream - aroused. Bree had been dreaming of her new purchase from the night before. Saturday evening she had sat drinking a bottle of wine and surfed the net for something to spoil herself with. Since breaking up with her boyfriend Bree had been feeling increasingly horny with every passing day. So the night before she had decided to do so...

On the Beach Ch. 02

by Kathi on Sep 16, 2017
Mature

The bright morning sun and a full bladder woke him up. "It's not even 7 o'clock on a Sunday morning," he muttered in disbelief while sitting on the side of the bed facing the ocean. His erection led the way into the bathroom where he had to wait a minute for it to subside before he could take his morning piss. As he automatically shook the last few drops...