Cheryl Stories

1,905 results
Orientation
Length
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Infinite Scroll

Shemale Shock Continues

by standingstones on Sep 12, 2017
Transsexuals & Crossdressers

I met Cheryl at a party thrown by my sister. I asked Cheryl to come to my place afterwards and she agreed. That was where I discovered Cheryl was a shemale. I did something I had never done before. I sucked on Cheryl's cock and I took her load down my throat. After that I ended up fucking Cheryl's tight ass and giving her my own load of cum. We had now been...

Bareback Brother-in-Law Ch. 04

by andoverblonde on Sep 12, 2017
Erotic Couplings

Dear Readers - You will get much more out of this story if you read parts 1, 2, & 3 first. ~ox +++++++++++++++++++++++ John sat, barely watching the game, wondering what he was going to do. He finally found a woman with a libido as powerful as his, but his wife suspected him of cheating. "I'm not giving up Shauna." He thought to himself. "And I'm not div...

Unimpressed

by Ashson on Sep 17, 2017
BDSM

The problem of Cheryl was raised at one of the teacher's meetings at Clendon All Girls School. "Cheryl is totally unimpressed by any punishments we might hand out," griped the English teacher. "She ignores detentions and she's actually hoping for a suspension, so giving her one would be self-defeating." "She's sitting on the maximum amount of demerit poin...

Opening Pandora's Box Ch. 02

by MiandEv2007 on Sep 16, 2017
Loving Wives

Almost two weeks passed as Scott and Greg continued to talk on-line. They agreed it would be best to let Cheryl cool down before anything was said concerning the website or their meeting. The delay was killing Scott. He was anxious to move things along with Greg and after the two weeks he came up with an idea. The next time he spoke with Greg he brought the...

Ixchel Ch. 06

by Ixchel2020 on Oct 13, 2020
Erotic Couplings

That night Cheryl dined alone. No one invited her to sit with them, none of her growing list of compatriots seemed to be around. And somehow, it was okay; on this, the third night of her four night package, she was for the first time feeling a little sated. That's not to say if an appealing man asked her to dance she'd say 'no,' but if it didn't happen, it w...

I Seduce a MILF at The Adult Pool

by TheBusinessMan on Mar 26, 2019
Erotic Couplings

This is an adult sex story. All the characters are of the age of consent or far over it! Any children named or mentioned are not involved in anything sexual. This is story number fifty five (55). This is the story of how I spent my summer vacation in Las Vegas, Nevada, USA. Enjoy and thanks for the views and votes. ++++ When you last saw me, I was s...

Home Alone Pt. 02

by grgy56 on Jul 15, 2020
Transgender & Crossdressers

So to recap... My name is Carl. My girlfriend Tess is shopping in the US with some of her friends which allowed me to dress up gurlie. Tess, of course is unaware of my love of wearing my feminine things and so I only do it around the apartment when she's not here. I had been using a breast enlargement pump and was now successful in filling my B-cups. Along w...

Her New Girlfriend Ch. 02

by grgy56 on Sep 25, 2017
Transsexuals & Crossdressers

Chapter 2: Transition I stayed awake all night thinking of what transpired the day before. My girlfriend Cheryl secretly recorded a DVD and caught me dressing in her lingerie and masturbating with her vibrator deep up my ass. After the grand viewing, she dressed me up in some of her lingerie again, put one of her wigs on me and fucked my ass with her doub...

Happy Halloween Party

by Blue88 on Aug 17, 2017
Erotic Horror

Ah... sorry if this is a little garbled... sorry. Words are really not my thing, I'm more comfortable with numbers...have always liked numbers. They're solid, predictable...if you do it properly, the answer is always right. Wait... let me start again, from the beginning. My name, yes, my name. My name is David Martin. Not an uncommon name, probably a bunch...

Always On My Mind

by CarterCounty on Sep 15, 2017
Loving Wives

Copyright April/2011 Another tale of a troubled marriage. There are no descriptive sex scenes in my work, but I hope you'll read and enjoy my story anyway. If you like or even dislike this tale please make comments or send emails concerning your feeling about my work. Constructive critiques, comments, and emails are welcome and I appreciate you taking the...