Emily Osment Stories

4,701 results
Orientation
Length
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Infinite Scroll

Lucas's Older Brother

by Lucas96 on Dec 2, 2019
Fetish

Disclaimer: this story involves cuckolding, humiliation, etc. *** Lucas and Emily, both 21 years old, had been dating for about a month. While Lucas had had previous girlfriends, he'd never felt the way he felt about Emily. They'd met in class at their small liberal arts college, hit it off immediately, and gone on several dates. After a week or two, Emil...

Natalie and Emily: Sister Surprises

by KeyesLodge on Oct 12, 2020
Celebrities & Fan Fiction

July 2020 In my previous story that involved Natalie Alyn Lind and Emma Dumont, I went into detail about what happened at the very end of the night. To recap, as I was dropping Natalie off at her house, the two of us were more or less 'caught' by her younger sister, Emily. In order to deescalate the situation, I ended up giving in to Emily's demands to give...

A Step Up

by AchtungNight on Sep 14, 2017
Celebrities & Fan Fiction

Intro: Greetings. The inspiration for this tale came to me while I was reading a LiveJournal celebrity blog recently. Judging by some comments I saw on there, I was not the only one who got such ideas from said blog. For the record, I had these ideas before I started reading the blog comments, though of course I still thank all those who helped my inspiratio...

Bicycle Girl

by zeropatience on Oct 3, 2018
Exhibitionist & Voyeur

For graduation from high school her mom and dad had bought her a Cinelli Gazzetta Della Strada touring bike. It was light weight and high-tech. She put a bike rack in the back of her old Toyota pickup and spent most of the summer participating in bike rallies and competitions. Emily was a month away from her twentieth birthday. As a former cheerleader and g...

Hide and Seek Ch. 04

by ChinaDolly on Sep 14, 2017
BDSM

((Hello everyone and thank you for being so very patient with me well waiting for this chapter. I must admit that I have become a little caught up in the other story that I am writing but I promise I will not take that long to update this again...unless of course the world ends or I get abducted by aliens. Then I have absolutely no say in the matter. So I...

Emily Ch. 02

by silversun84 on Sep 19, 2017
Letters & Transcripts

Author's note: Emily is a cute young BBW who works as a teacher, and enjoys sexy role-play. She has short curly brown hair, pale skin, with freckles, and wears glasses. Emily and I often explore different naughty characters and situations and this story documents one of them. This time the scene is a cruise ship. We are both aboard, supposedly enjoying a ho...

Pleasing Juliette

by MTL17 on Sep 14, 2017
Celebrities & Fan Fiction

Author's note: This a Nashville story takes place in the first half of Season 3. ***** Emily had been warned that Juliette Barnes was impossible to please. That she went through assistance like toothbrushes, wearing them down until they were shadows of their former selves. Most of all she had been warned that Juliette was an evil bitch who sooner or later...

Couple & The Soldier

by carolinky on Sep 14, 2017
Loving Wives

This is a story about a married couple that meets a US Army Ranger while vacationing in Cancun. Captain Jim Maze draped a hotel beach towel over his arm and walked toward the couple sunning on the beach. He made a quick assessment. The man was stocky and looked older than the woman. He guessed late thirties. The woman, on the other hand, had to be in her m...

Trailer Trash Ch. 03

by Slickman on Nov 11, 2019
First Time

Note from Slick: This is the last chapter of the Trailer Trash story. Please read "Trailer Trash Ch. 01 and 02 first to get up to date. All characters are at least 18 years old in the story. All rights reserved. * "Emily wait up!" Brandon yelled from behind the two mutt dogs trying to catch Emily. She had about a 50 foot lead on him and the dogs and the g...

Sorority Gangbang Sisters

by HeyAll on Sep 25, 2017
Group Sex

Part 1 of 4: The Pledge Emily stood nervously. She was the youngest person in the room full of people. A fresh faced 18-year old who was new to the college system. Her hair was tied in a ponytail. Her thick framed glasses made her look like a nerd. But she tried to be unafraid. She tried to be strong and brave. "Why should we allow you to pledge?" Morgan...