Jessie Stories

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Watching Jessie at the Hotel

by StThomas83 on Mar 11, 2019
Interracial Love

This is a continuation of the story Watching Jessie (glory hole). ***** By the time I got Jessie dressed to leave the glory hole booth another cock appeared through the hole in the wall. Jessie wasn't about to leave it there. Jessie promised that she just wanted to practice her sucking skills. Jessie knelt down in front of the cock and began kissing and...

The Investigation Ch. 03

by HStoner on Apr 11, 2018
Exhibitionist & Voyeur

This story is a work of fiction. Any similarities to any real person or entity are entirely coincidental and unintended. This story is part of a series by this author that includes The Investigation, chapters 1 & 2, A New Investigation, and A Peaceful Investigation. Hopefully, this story can be read with enjoyment on its own, but the prior stories give conte...

Take Cover from Tracy

by RetroFan on Dec 21, 2017
Romance

INTRODUCTION & DISCLAIMER Save for twists of fates in both their lives, Jessie and Jake should never have been in the Australian city of Darwin for Christmas 1974 and never should have met. Jessie, an ambitious young officer of the Women's Royal Australian Navy, had planned to spend Christmas in Perth with her family until her selfless good deed sees her g...

A Healthy Adolescent Sex Drive

by RaistlinMajere on Jan 8, 2019
Transgender & Crossdressers

CHAPTER 1 - WOULD YOU LIKE TO HAVE SEX? Jessie sighed and breathed out. Hot water splashed down her soft back and she picked up the bottle of soap. Squirting some into her favorite loofah, she started to scrub her body. Being a high school student, she cared very much about her appearance and standing in high school. Therefore, she couldn't afford to stink...

Megan & Jessie #05

by Jappio on Sep 14, 2017
Exhibitionist & Voyeur

I perhaps made a mistake when I made a bet with Jessie. I might have really paid for it more than I was intending. You see, the other week, I was giving Jessie a bit of crap about a test we had to take. She was insisting she could score better than me. Now I know I really like everything about Jessie, and would never say something bad about her. Yet I know...

Playing with Fire

by MaxwellSpanx on Apr 22, 2020
Loving Wives

*** Authors note: if you're interested in knowing more about Don and Jess then check out my series Love Burns. Credit to Philanthropist for the final scene. *** Hand in hand Don and Jessie stepped into the pub as a couple. He felt proud that she held tight to his hand. It felt like a promise. Upbeat Irish folk played over a sound system, so Don had to rai...

Stepmom Sent Back to School Ch. 02

by redwolf555 on Mar 11, 2019
Fetish

Chapter Two: "Jessie Takes Over" Another change to the household happened over that Saturday. Another shift in power from Jenny to Jessie. There had been no discussion, no choice, Jenny and Jessie switched bedrooms. Jenny moved into the small bedroom. At the same time, Jessie moved into her mother's bedroom. This was so they could keep their roles and not m...

Sexploits Ch. 03: Jessica

by dpingjessie on Sep 14, 2017
Loving Wives

A couple years ago, I posted a story about my first group sex experience and stated that it was the first time I had a sexual relationship with my friend Jessie. While the story itself was true, that particular fact was not. At the time of the writing, there were personal reasons as to why I omitted the fact that I had actually slept with Jessie previously....

The Bull, and the Princess Pt. 01

by DnDisfun on Aug 1, 2018
Romance

PT 1: The Witch ALL CHARCTERS IN THIS STORY ARE 18 YEARS OF AGE OR OLDER. Jessie fondled her lover's breasts and whispered in her ear, "I love you so much!" Her partner, Vanessa, turned her lustful eyes, opened her mouth and... made Jessie's alarm sound. Jessie awoke suddenly, and angrily. She slammed down on the alarm clock and got ready for school, and w...

"Best Friends" a Sad Story

by eroticjuggalo on Sep 25, 2017
First Time

My Friend Jessie and I have known each other since High School. I would always see her in school and kind of had a crush on her, but didn't know her much other then that. I first officially met Jessie one night while I was hanging out front of another friend's house. Jessie and her boyfriend drove up and parked and started talking with the group of us. The...