Cheryl Stories

1,905 results
Orientation
Length
Source
Infinite Scroll

Lucky Pt. 02 Ep. 10

by Happytimeshappy on Jan 29, 2018
Sci-Fi & Fantasy

The confession Lucky and Addison waiting sat were setting on the couch when the sounds of the door unlocking pulled them from their conversation. It was time for Cheryl to be home. His stomach was tying into knots as he thought about what he and Addison were about to tell Cheryl. He didn't want to hurt her. He didn't want to see her destroyed as she heard...

DVD Rental Guy Takes My Wife

by DVDsalesGuy on Sep 13, 2017
Loving Wives

The doorbell rang, and Gary glanced over to Cheryl once again to see if she looked like she would back out. This was the point of no return. She gave him the slightest of nods, as if to say "Answer the door before I change my mind, you dumb fuck!" Gary opened the door just as the bell rang a second time, and welcomed the DVD rental guy. Gary and Cheryl had...

Kaitlyn and Cheryl Ch. 01

by WhatIKnow on Sep 19, 2017
Group Sex

This is the continuation of Back in the Saddle. I got several requests to continue the story and felt like it was time to describe what happens once everyone is back from the festival. For those just joining the story line, you can start here without losing much or read Back in the Saddle to catch up with the characters. ************************** "What do...

A 70's Show and Tell and more

by Bob Waters on Sep 18, 2017
Exhibitionist & Voyeur

All characters in this story are of legal age. "What happened?!" Tina asked insistently on the phone. "I SAID I am NOT going to talk about this on the phone," Cheryl said. "My mother could pick up the extension." "OK, get over here RIGHT after dinner," Tina commanded. Cheryl hung up with a deep sigh. She wasn't sure she was ready to talk about it with T...

They're My Sister's Wicked Ways!

by grgy56 on Sep 18, 2017
Transsexuals & Crossdressers

Thanks for all the great comments. I know this third chapter has been a really long time in cumming but I hope you enjoy this one as much as the others. ***** So the first time I was caught by my sister, I was dressed in some of her sexy lingerie. That was bad enough but she also caught my best, bum buddy (literally) Chris fucking me and cumming in my ass...

Cheryl's Revenge

by grgy56 on Sep 16, 2017
Transsexuals & Crossdressers

Cheryl was an extremely well to do business women in her late 30's. She could afford to put up with the unemployed, younger, money grubbing, bastard she had been supporting for the last five years. Even though Cheryl could afford a house keeper, Mike was given an ample allowance in exchange for keeping the 2,200 square foot condo suite tidy. She felt he ha...

Pita, PETA, Peter, and Naked Models

by SuperHeroRalph on Sep 17, 2017
Celebrities & Fan Fiction

This is a Earth Day contest story. Please vote. * Taking a beat down for God, supermodels misunderstand their Earth Day modeling assignments. Christie Brinkley was the first to appear for the photo shoot, an Earth Day commercial for Pita Breads, a new bread, even lower in carbohydrates and calories and made with all natural ingredients. Since she's always...

A Time of War Ch. 02

by doc87123 on Sep 14, 2017
Exhibitionist & Voyeur

The day began just like the day before. One of the comforting things about military life is the routine, if you like that sort of thing. After PT, I showered and marched to class. I was looking forward to flirting with Cheryl today. When we reached the school, I dismissed the platoon, and went to the class. I rescanned the manual that they had handed out yes...

Lucky Pt. 02 Ep. 03

by Happytimeshappy on Jan 14, 2018
Sci-Fi & Fantasy

Hangover Cure "Lucky," came a soft call in his ear, waking him in a start. "I didn't mean to scare you." Cheryl stared down at him with a weak smile on her face. Dark bags sagged under her eyes and her hair stuck up in every direction. She looked like she felt terrible. "Are you okay?" He asked as he propped himself up on his elbows. "I feel like a train...

Her New Girlfriend Ch. 03

by grgy56 on Sep 25, 2017
Transsexuals & Crossdressers

Chapter 3: Completed Well up to now Cheryl videotaped me in her underthings and masturbating; she took me to her friend's spa where I was made hairless and made up to look more feminine; then purchased a number of sexy outfits and put on public display. Quite a full day by any other standard, but we weren't finished yet. "Ding-dong!" the front door. "Gina...