Hailey Stories

306 results
Orientation
Length
Source
Infinite Scroll

Hailey's Journey Ch. 15

by nanmar on Sep 19, 2017
BDSM

Nick was a one man percussion band today and he was thoroughly enjoying himself. His drum sticks included a wide range of canes, floggers, whips and straps. His instrument itself was, of course, a much modified Hailey. She was naked, as usual, hanging face down, held up by a complicated arrangement of straps and ropes. These held her head up, compressed he...

Caught Cheating Ch. 01

by Hailey157 on Sep 16, 2017
Transsexuals & Crossdressers

Hailey lifted her head, which had been resting on her arm up for the second time that hour. Down at the front of the lecture hall, her chemistry teacher was droning on about the wonders of balancing chemical equations. Sitting up in her chair, Hailey stretched out her arms and yawned softly. As she did, the smooth fabric of her bra shifted around her chest....

Butt Jewelry

by Xarth on Jul 15, 2020
Anal

Author's Note: This story takes place in one of those high schools where everyone is eighteen or older. You know the ones. **** Riley waited for Jen by the front of the school. She smiled when she saw her friend approaching and turned to fall into step beside her. "Morning," Riley said cheerfully. "Morning," Jen greeted her in return. "Anything interesti...

Hailey Worked the Day Shift

by masterfeedlarry on Sep 16, 2017
Loving Wives

(This is a continuation of the story Hailey's Rebound, but it can be read as a stand-alone story.) * Jimmy Madison felt like the luckiest man in the world. Less than a year ago he had married the sexiest woman he had ever met. Her name was Hailey Scott and he had first met her his senior year in college when she was a freshman. He'd lost contact with her...

Hailey's Journey Ch. 02

by nanmar on Sep 14, 2017
Novels and Novellas

"Ms. Wentworth, I believe you are here for your punishment." The quiet voice made Hailey shiver with fear and anticipation. "Yes sir." "You have made many, many errors in your work, Ms. Wentworth. We know exactly what you are capable of, and this merely tells me that you have been careless and lazy." "Nnno, sir, I...." "Silence! You have earned yourself...

Hailey's Journey Ch. 07

by nanmar on Sep 14, 2017
BDSM

The rest of Hailey's week was similar to her second day, except for changes in costume. She wore a Playboy Bunny outfit, or leather corsets or short little cheerleader outfits, and carried out her dusting and serving duties. As long as she obeyed him, she got her reward in the night, when he would give her a nice warm, scented bath, massage her tired body, a...

Hailey Grace's First Threesome

by fadedblu on Sep 1, 2017
Group Sex

Hailey Grace first read the ad on the internet. Her subscription to the adult dating site had started out as a bad joke, one too many margaritas with the girls after a 50 Shades of Gray party. As the only unmarried girl in their circle of friend's she'd owed it to them, they argued. They needed to live vicariously through her. So, she'd done it. One of the...

A Slave under Contract Ch. 04

by gynarchite on Jul 31, 2018
Sci-Fi & Fantasy

Chapter 4 – The city of Galos We left the house the next morning, flying the aircar to the airport. Long-distance travel needed a much bigger craft to make it efficient and safe, so my owners would take a supersonic plane to fly to the island city Galos, a thousand kilometres to the south. My arse was still sore from the pounding that Mistress Delilah's str...

Running Mates

by noreaster20 on Apr 14, 2020
Erotic Couplings

This story, like all my stories, is a work of fiction. All characters are age 18 or older. Any similarities between any character in this story and any real person is unintentional and coincidental. As always, your comments are welcome. = = = = = = = = = = = = = = = = = = They were running mates - not in a political sense, but in a literal one. Hailey and...

The Ski Bunny Ch. 06

by photosaurus on Sep 19, 2017
Group Sex

"Is it awkward?" I asked. She looked at me with the bright blue eyes that I fell for right after I fell on her at the ski resort. She enjoyed a sip of sauvignon blanc without breaking her gaze. "Awkward?" Her lips, perfectly covered in scarlet smudge-proof lipstick, effortlessly formed the word. Even having just finished a four-course dinner, they were nea...