Cheryl Stories

1,905 results
Orientation
Length
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Infinite Scroll

The Cheryl Cummings Story: Early Years Ch. 02

by mark_8675309 on Dec 12, 2018
Exhibitionist & Voyeur

** Cheryl Visits Home on Spring Break ** The years went by after prom. Cheryl and Chris went out for about a year, then they decided it would be best to break up when Chris went away to college. They decided at this point that they should be free to date other people and not have to worry about it. Another year went by, and it became time for Cheryl to g...

How Much Love?

by StangStar06 on Sep 12, 2017
Loving Wives

"God Damn it Cheryl, you've been working with us for four months now," said Connie. "This is the first time we've ever gotten you to come out with us. So don't start trying to leave before you've had at least one drink." "And at least a dance or two," piped in Nancy. "There will be a lot of guys here on a Friday night. And you're a good looking woman. You w...

Kaitlyn and Cheryl Ch. 02

by WhatIKnow on Sep 16, 2017
Group Sex

When my alarm went off it was still dark outside. Cheryl was curled up in front of me and was sound asleep. We had about thirty minutes before we had to leave my place, but I wanted to get moving. My dick was hard so I rubbed it on her ass. Cheryl stirred and she pushed her ass against me. After rubbing for a few minutes she finally opened her eyes, but by n...

Cheryl Takes It All Off

by rafters11 on Sep 25, 2017
Exhibitionist & Voyeur

Cheryl and I had been dating for 3 months and having sex for 2 months so when she suggested I try to find a place on a Florida beach for spring break I readily agreed. Cheryl is a 5'2", 100 pound beauty. She is a very serious, smart and personable college senior getting ready to graduate in June with a degree in finance. She has blond hair she wears just lo...

How I Earned My Place in the World

by WillieTurner on Sep 13, 2017
BDSM

As she was untying me, Cheryl asked me a most surprising question, "Tell me, what do you want out of this relationship? Surely you want more out of this than being a pleasant little fucktoy at my beck and call!" I thought a bit, unsure how to answer. My lips were a little swollen and numb, she had sat roughly on my face while I worked kind of hard to make h...

Shemale Shock

by standingstones on Sep 12, 2017
Transsexuals & Crossdressers

My sister Louise was always trying to set me up with women she knew. Somehow she felt as if she were responsible for my love life. Louise's latest scheme was to throw a party and invite me and all her women friends that she could. I arrived at my sister's party and to her credit there were other men there besides myself. Unfortunately most of the women the...

Club 35 - Fifth Visit

by Gln1517 on Nov 18, 2019
BDSM

This is the next chapter in Club 35. It would help your understanding of the characters and their experiences if you read the previous installments. Your comments are appreciated and i do, when its called for, respond to the comments, good or bad. Please vote and enjoy! *** It had been a busy eighteen months for Jennifer Lowe, a thirty seven year old busin...

Weekend in Chicago Pt. 02

by RedDevil20 on Jul 2, 2019
Erotic Couplings

Rolling over on the pull out sofa the next morning, I could see Carly's soft, thin, left leg sticking out from underneath the blanket. Peaking under the covers I followed those legs, up to her thighs, right to the pair of purple panties that covered her pussy. Then pulling back the covers further I saw her hard nipples pressed against the white tank top she...

Chaste (A One Week Chronicles Story) Pt. 02

by Louise69 on Oct 14, 2017
Transsexuals & Crossdressers

Dear Reader, thank you for clicking on this story and reading it. I hope that you enjoy it, but know that it will be my most divisive story! Hopefully, by the end, you will see why the story was told...each story I tell has a part of me in it and helps prepare me for my other writing, but some of my stories have more of me in them that others. The One Week...

The Janitor who was King Ch. 02

by wolvie01 on Dec 11, 2018
Interracial Love

An innocent and sheltered wife and mother goes back into the workforce in teaching in the deep south after both of her children go away to college. Things aren't exactly going as she thought they would. Please read The Janitor Who Was King to better understand this chapter. ***** Cheryl woke up about 4am to the sound of Rob stumbling to bed. She strugg...