Cheryl Stories

1,905 results
Orientation
Length
Source
Infinite Scroll

Continuing Adventures Of Panty Boy

by Panty10 on Oct 15, 2017
Fetish

I sure had a wild time at the poker game and it was something I never expected. After we talked about it, I was clear that our friends did not think any less of me and that they had a great time too. Cheryl and I were lying in bed, in our matching panties, the following night, just kind of snuggling and talking about it when she reached down and started care...

A 70's Show and Tell

by Bob Waters on Sep 18, 2017
Exhibitionist & Voyeur

All characters in this story are of legal age. "That's so fake, no chick looks like that," Billy said again so superiorly. Cheryl was really starting to get annoyed with him. He really thought he was shit hot right now. Parents away and the small circle of them smoking weed and drinking Southern Comfort watching a porno on his dad's brand new Betamax. Bi...

Compromising Positions Ch. 09

by Timeris on May 12, 2020
Group Sex

When Cheryl and Jenne walked into the back yard, Mark was sitting on one of the loungers, paying close attention to Angela. She, on the other hand was sitting up straight on a lounger, feet on the ground, with her tiny thong pulled tightly between her lips. "Mark, the sunglasses aren't fooling anyone, we know EXACTLY where you're looking," Jenne said with a...

The College Recruiting Trip

by Webplaya on Sep 12, 2017
Loving Wives

My wife and I have been happily married for ten years. We are both 38 years old and we have a great sex life. The one thing I have always fantasized about that we have never done is to have her have sex with someone else. Once in a while during our lovemaking I would say something like this to her as I pounded her pussy, but we never spoke of it other than...

Becoming Brenda's Slave Ch. 03

by lorihole on Sep 16, 2017
BDSM

When the door to Brenda's room opened, I was surprised to see that it was not Brenda who answered the door. It was a tall, voluptuous woman with long dark hair that fell down past her shoulders to just above her lower back. She was wearing a black leather corset that pushed her large breasts up making them show magnificently. Below that she had on only a pai...

Call Me Pegg

by grgy56 on Sep 16, 2017
Transsexuals & Crossdressers

I was already hard and I hadn't even put on my panties yet. Clearly I was anticipating what was to unfold for this evening. Late last evening my girlfriend Roberta (who actually hated that name so I must call her Robbie), had me dress in my white baby doll with loose fitting, thin nylon panties. I also wore white thigh highs and white stiletto heels. She fu...

My (Im)perfect Mate Ch. 01

by grgy56 on Sep 13, 2017
Sci-Fi & Fantasy

"Welcome to Maid Perfect where we can create your perfect household staff." I was greeted by a curvy, big breasted blond saleswoman. "I'm Stella." Stella reached out her right hand which I took. It was a gentle grip and warm to the touch. The handshake lingered long enough to make a connection but short enough not to be too uncomfortable. Stella's blue eye...

The Daughter Ch. 03

by hazel43 on Sep 14, 2017
BDSM

Cheryl felt herself begin to awaken. She was standing suspended with her arms over her head. A rush of fear swept through her as the memory of her branding became fresh in her mind. Terrible throbbing pain emanated from her right hip. Tears filled her eyes as she struggled to open them. The cold walls and floor were made of gray stones. Iron bars filled th...

Walk a Mile in Her Shoes Ch. 01

by grgy56 on Sep 16, 2017
Transsexuals & Crossdressers

"Well I think it's a great idea." Said my girlfriend Cheryl after bringing up the topic during dinner. It was a month before the "Walk a mile in her shoes" support parade against abuse of women. "What kind of example would it be if my own feminist boyfriend won't support me especially at WFS?" Cheryl worked as an executive officer at "WFS"; a women's financ...

A Lazy Sunday

by tirreno12 on Sep 17, 2017
Loving Wives

A late spring sunny day. Cheryl and James' garden. She is a delightful forty something lady. Medium size, short blonde hair, green eyes, lovely legs. She is blessed also by a spiced and varied conversation. James is about ten years older. Rather strong built, grey haired, he owns with his wife an antiquarian gallery and bookshop. It's Sunday and for the firs...