Jessie Stories

1,722 results
Orientation
Length
Source
Infinite Scroll

Party Night

by abn4eternity on May 16, 2018
Group Sex

The party had not begun yet as David and Susan knocked on the door. The New Years Eve party invitation had said the party would start at 6 p.m. but as usual they late, twenty minutes late to be exact. It didn't really matter since they seldom arrived when the party was set to begin. Most of those that were already there were older family members or next door...

Secretary Sandwich Pt. 04

by dpingjessie on Jul 13, 2020
Group Sex

Having generated more attention around the office as of late, Abby was in a new situation tonight as she followed one of her new friends up to his apartment. Following several months of being shared between her boss and his business associate, Abby, unbeknownst to her at the time, had been caught in action with the two gentlemen, leading to some ultimately h...

Stepmom Sent Back to School Ch. 04

by redwolf555 on Mar 11, 2019
Fetish

Chapter Four: "The Rest of the Story" It was the morning of graduation, a Saturday. Silva was upstairs getting ready for the day. Jessie and Jenny were seated at the dining table. Jessie says, "I'm so proud of you Mom. You did it! And you're at the up of your class." Jenny smiled. Jessie goes on, "I've been thinking about the future." "Oh, this shou...

A Date with Fate (Jessie's Girl)

by Smokey125 on Apr 3, 2019
Non-Erotic

SS26: "A Date With Fate (Jessie's Girl)" *** This is SS #26, entitled "A Date With Fate (Jessie's Girl)." This is part one of a two-part sequel to my story "Step-Mommie Dearest." This is the non-erotic portion, setting up the forthcoming actual erotic portion (which will be SS #27, called "And The Truth Shall Set You Free"), and so I'm tempted right now...

Were in the City Ch. 11

by freetowrite2020 on Mar 9, 2020
NonHuman

Jacob stood at the back window watching Jessie dig up the grass to start her kitchen garden plots. He knew she was fighting the disintegration of her world by creating something she could hope was permanent, something she might see blossom and grow. In the past week Jessie Taylor had disappeared. She had resigned from her job, saying she needed to start a n...

Annie's Life Ch. 02

by trappedinside on Aug 20, 2018
Erotic Couplings

The two did have pizza. A stroll thru the mall. A little shopping and finally a drive downtown to the Emmerson hotel. The valet opened the passenger door and then raced around to the driver side only to find Annie already out and handing him her keys. "Guest room number?" He asked. "Just dinner." Annie calmly said. Jessie grinned when she heard Annie offe...

Quest for Normal Pt. 01

by JimBob44 on Aug 6, 2019
First Time

*Author's Note: Any and all persons engaging in any sexual activity are at least eighteen years of age. Disclaimers: This story has been edited by myself, utilizing Microsoft Spell-check. You have been forewarned; expect to find mistakes. Also, if male or female bisexuality offends you, kindly hit your backspace key now. *.*.*.*.*.*.* "Eighteen years lon...

Megan & Jessie #06

by Jappio on Sep 14, 2017
Exhibitionist & Voyeur

Part 1 "You really don't think I could use a bit of slimming up? I don't know, I think I could use a little work. This ass is far from perfect!" Jessie exclaims, her hips cocked to a side as she looks over her shoulder to me. She even groped one of her own cheeks as she inspected herself. I just don't know some days. At times, I think it would be impossible...

Sara & Laura Ch. 03

by wowser1 on Dec 31, 2018
Transgender & Crossdressers

Sara sat cross-legged on her bed, cell phone pressed to her ear. The phone rang twice. Three times. She could feel her blood pressure rising as she waited for someone to pick up on the other end. She chewed her lip anxiously. Four times. Then, a click. "Doctor Laura Stringer's office, Rachel speaking, how can I help you?" came a cheery voice. Sara realized...

Stepmom Sent Back to School Ch. 03

by redwolf555 on Mar 11, 2019
Fetish

Chapter Three: "The next few weeks" The next morning, Monday, all was well. Jessie drove Jenny to school. Before she left her, Jessie said to Jenny, "Remember, you are to delay as long as you can until Silva shows up." "Yes mom." Jessie drove to work and had a great day. First, her immediate boss thanked her for her hard work. Then the CEO sent her a pe...