Hailey Wench Jail Stories

14,604 results
Orientation
Length
Source
Infinite Scroll

I Call Him Mr. Tibbs Ch. 05

by dsoul on Sep 14, 2017
Interracial Love

Misty drove into her neighbourhood street with her kids playing in the back seat. She noticed the car parked by the curb in front of the Dreshner's compound with the name and logo of the company Phone-R-Us imprinted on the side. The door to her neighbour's home came open and a suspicious look came on her face when she saw the black man exit the house and wal...

Bad Little School Girls Pt. 02

by MsTeacher on Nov 20, 2017
Erotic Couplings

That same night Jen and Hailey laid in bed together. Jen's fingers traced over Hailey's body sending goose bumps over her skin. She stoked Hailey's nipples until Hailey began to grind her wet pussy against Jen's leg. When it seemed like she would make herself cum, Jen adjusted, withdrawing her leg and replacing it with her hand. She stroked Hailey's thighs,...

Midas Touch

by CreativityTakesCourage on Dec 11, 2018
Loving Wives

AUTHOR'S NOTE I know I said that my next planned story would be a Reconciliation one, but the idea for Midas Touch grabbed me and wouldn't let go, so I went where the inspiration was. Greatest Gift Of All (the reconciliation story) is coming along and barring some disaster should be out prior to Christmas! Like my previous story, The Garden of Grace, M...

Lesser of Two Evils

by Andi_Lembke on Sep 25, 2017
Transsexuals & Crossdressers

[So to update you all. I'm sorry I haven't completed any more chapters of NWTBYG or Porn Princess. They're in the works, but creation, and good storytelling takes time, something I have less of now. I left my receptionist job to take a writing gig, and all my writing energy is going into that, but my passion for hot stories smolders intensely under the surfa...

Clique Ch. 02

by PencilSketch on Sep 15, 2017
Illustrated

(All characters are 18+) Clique (L to R) Hailey Radclyffe, Henry Bridge, Sofia Lorenzini, Carlos Lorenzini,Trista Dory, Paulie Westwood, May March, Vinton Gray Chapter 2: The Liar I skidded in my socks over to the dryer. I had to shift my cell phone and hold it between my shoulder and tilted head so I could start transferring clothes to a hamper with m...

The Sales Man

by BillandKate on Jul 9, 2019
Loving Wives

As always, all characters, events, companies, etc. are figments of our imagination and have no connection to any living or dead persons, true events or actual companies. In other words, this is all fiction. M.P. "I've never met a man that sells anvils before." C.C. "It takes a real salesman; I can tell you that. Anvils have a limited appeal, you know."*...

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...