Jessie Stories

1,722 results
Orientation
Length
Source
Infinite Scroll

A High School Bet

by sexy_jessie on Sep 12, 2017
First Time

Jesse and Jessie Sinclair were two of the most popular kids in their senior year at high school. Twin brother and sister both were eighteen, tall and thin with shoulder length blond curls and bright blue eyes. Unbeknown to the rest of the school they were also two of the kinkiest people in the whole town. One day Jessie lay, lounging, on a sofa at their hou...

SEXtuplets

by sexgundam666 on May 1, 2018
Fetish

Author's Note: Requested by KC55. WARNING! This contains weird pregnancies, including; Breast Pregnancy, Ass Pregnancy (not the cheeks that'd be... too weird somehow), and Testicle Pregnancy. This all involves futanari of course. Read on if you so desire. ***** Jessie cooed softly as she slid off her latest partner. They were a real beauty, big tits and hi...

Little Jessie and the Bad Dream

by VirginiaMarieAndrews on Sep 16, 2017
Fetish

Preface, general = = = = = = = = = = A friend and I were playing around with interactive fiction. We tried a number of ideas until we hit on the kernel of this one. We played for about a week then decided to reset, write a back story, and see if there was a real story here. The interactive story we do is ridiculously detailed. What we're thinking of doing...

Megan & Jessie #04

by Jappio on Sep 14, 2017
Exhibitionist & Voyeur

Megan and Jessie #4: Sleeping Beauty Part 1 * I was lost in my thoughts as I sat around during our drama club's meeting. It's a small club, just a few of us girls who needed a few extra credits. Now of course I'm not usually one for being out on stage, but I was sort of the director in the group, so it worked out. I was comfortably only dealing with the ba...

Who's the Slut Now?

by griffin57 on Sep 13, 2017
Transsexuals & Crossdressers

Special Thanks to the beautiful Mistress Joscelyn. You rock Love. * Ch 01 David really should have known better. Why would he ever agree to it? He had caught his girlfriend cheating again, called her slut and said it was over. Three days later her name popped up on caller ID. She just wanted to apologize, she said, and let him know there were no hard fee...

West of Boston: Wayne's Happy B'day

by Softouch911 on Aug 31, 2017
Group Sex

This story is the first in a series, "West of Boston." Wayne woke up dreaming of sex again. But when it registered that his cock really was being sucked, he tried to sit up. Between his knees, Jessie was busily working him with her mouth. She smiled up at him and said: "Happy Birthday, honey." Keeping her eyes on his, she returned to his cock. Wayne sighe...

Were in the City Ch. 08

by freetowrite2020 on Mar 3, 2020
NonHuman

Bloody (yup, literally) Hell! ... Jessie was shaking, angry and frightened by everything that had happened, everything that she'd been feeling, in the last few days. She was applying pressure to the wound on her arm to stop the bleeding. It was too deep, too wide, she wasn't going to be able to deal with it on her own. She could not believe she was going to...

Summer Night for Three

by bbwsadieml on Sep 1, 2017
Group Sex

Tate, Jessie, and Adam sat in the simple private courtyard behind Tate's townhouse. It was late summer, the evening air filled with the scent of barbecue from other yards, the sound of chirping crickets, and the sky was turning to twilight. All three of them were feeling the mellow effects of one too many glasses of wine. Tate's age was late thirties, while...

Blindfolds

by TessMackenzie on Aug 31, 2017
Exhibitionist & Voyeur

"I'm bored," Megan said, in the middle of sex. "Let's do something else tonight." Jessie stopped moving, and lay there, looking at Megan, apparently surprised. Megan suddenly wondered if that had been the most diplomatic way to say it. "What?" she said, feeling guilty. "I am. I'm just telling you." "You're bored?" Megan nodded. It still didn't seem com...

Were in the City Ch. 16

by freetowrite2020 on Apr 27, 2020
NonHuman

It's Silvie Richard ............. Jacob, Jessie and Liam were sitting huddled together on the edge of Jacob's bed staring at the image on Jessie's phone while listening to Helen talk. "I know the woman in the photo looks a lot like Silvie, but it's been 123 years. How much detail do either of us really remember about her Jacob? It is just a freaky coincide...