Tickle Debbie Stories

18,747 results
Orientation
Length
Source
Infinite Scroll

Companion Fare Ch. 05

by evals22 on Sep 17, 2017
BDSM

Donna woke early, as was her usual routine. She spied Lori curled up on the floor in the fetal position. Her arm was acting as a pillow. Donna stepped out of bed, stretched her arms. She went to her suitcase and pulled out a few items, placing them on a chair. She picked up her panties from last night and tossed them on the chair. She walked over to the slee...

My New Sister Ch. 06

by Jizaz_Jester on Sep 19, 2017
Erotic Couplings

A little over a month passed and Connie refused to talk to me. Even with Sammie as an over the phone mediator she always managed to steer the conversation away from me until Sammie waved me out of the room for privacy. Honestly it got to me more than it should have, so much so that I told my step-sister that I wanted out of her prostitution scheme, and even...

New Jack Ch. 13

by deviantradoddness on Oct 8, 2018
Group Sex

Apologies for the long wait. This is (probably) the second-to-last installment in this series. This story contains pervasive same-sex action, cuckolding, and rough sex. If that's not your cup of tea, please feel free to pass over it. If these things do tickle your fancy (or something else) please leave a comment or send me a message: I'd love to hear wha...

My Wife's Secret Fantasy Ch. 01

by Kary_M on Sep 12, 2017
Transsexuals & Crossdressers

PART ONE: REALIZATION The old saying "you never really ever know some one" is quite true when it comes to my wife Debbie. Debbie has always seemed to come up with new surprises to keep our marriage stimulated and adventuresome. As I've recently found out though she seems to have been keeping some things to herself. Debbie was away for a twelve-day business...

Crazy Little Thing Called Sex Pt. 02

by Ian56 on Sep 18, 2017
Romance

2: The passion flower. The bus pulled in to the college stop and I gathered my things together to get off and head in for the first lesson of the week. It was Monday and the first hint of Autumn was in the air. Despite the bustle of students around me going about their daily routine, I was in a world of my own. Everything seemed different somehow. Everythi...

La Playa Ch. 06

by Fog43 on Sep 12, 2017
Group Sex

Edited by Sussurrus Tuesday Morning at the Spa Tuesday morning dawned with the broken, puffy clouds typical of a summer day in the Caribbean. A few couples and small groups still slept or stumbled groggily back toward their rooms from where they'd collapsed the night before. Some people, sticky with cum, oil, or other fluids, took advantage of the showers...

Office Hero?

by 4eyedbrit on Sep 14, 2017
Anal

It was the night before Christmas eve, the night of the office Christmas "do" - my least favourite night of the year. It was already dark at around three thirty when I finally managed to slip away from the manufactured merriment in the stuffy and overcrowded Board room. I donned my coat, stealthily dashed up the stairs and headed for my usual 1st floor hid...

Perfect Mother, Perfect Slut

by Jazz_E_too on Jul 4, 2018
BDSM

"Time's a-rolling," thought Debbie, as she pecked at the keyboard of her laptop, trying to get started on some serious surfing. She realized her friends were right – at least in one aspect of their oft-repeated, unsolicited advice: She'd been divorced for almost four years, and, at the age of 39, it was time to get back into circulation. As a single mother o...

A Vibrating Kind of Valentine's Day

by andtheend on Sep 13, 2017
Toys & Masturbation

Husband buys his wife a combination dildo and vibrator for Valentine's Day. "Happy Valentine's Day, Honey." "Oh, sweetie, you bought me flowers and chocolates. How nice? This is so much better than what you bought me last year, a six pack of beer that we had to split." "Yeah, well, there's nothing too good for my baby. Besides, they gave me an unemploymen...

Community Property

by adamgunn on Sep 14, 2017
Erotic Couplings

by Adam Gunn copyright 2015 When you marry a woman, you marry her family. Never forget that . . . Back in the day, when the idea that sexual harassment in the workplace wasn't that bad of an idea, I had this girl that worked for me. Debbie was cute, and if her clothes weren't always the most current fashion, if a new blouse was something to be celebrat...