Awkward Stories

44,618 results
Orientation
Length
Source
Infinite Scroll

Lissy

by falteringtale on Oct 6, 2020
Exhibitionist & Voyeur

In spite of what her friends would tell you, Prissy Lissy wasn't a prude. In college, she had gone streaking down a quiet suburb boulevard. It was a drunken dare and a "mistake" that she would secretly regret. But when teased, she retained it as proof that she was a free spirit. Did it really matter that she'd only been with a few men in her life? She wasn'...

Simple & Straightforward

by simpleup on Sep 17, 2017
BDSM

I first saw her picture on the dating website I'd just joined. Her screen name was "simplesf" and she was older than me. Much older by my normal standards, whatever those standards might be. I hadn't dated in two years, and hadn't had a sustained relationship in even longer than that. So saying what was normal, and what wasn't, was a guess at best. But her...

A lift from a stranger

by Somewriter on Oct 18, 2013
BDSM

It was a sunny Friday afternoon and you were now regretting your current choice of outfit. It had been miserable weather the last few days and you did not expect this sudden heatwave. you were in a long sleeved shirt and jeans and was now sweating from the heat. The fact that you had a rucksack full of heavy books and notes did not help the situation and you...

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Every Day Will be Like a Holiday

by MsQuote on Sep 15, 2017
Novels and Novellas

Even though my son Brandon was nineteen and in his second year of college, he still liked to alternate the years he spent holidays with me and his dad. This year was my year for Thanksgiving, and since my parents were in Sarasota for the winter, Brandon and I were left to fend for ourselves. Or so I thought. "Hey, Mom," Brandon said to me when he came in f...

Bored Teen and a Loser

by notsogood on Dec 30, 2017
First Time

I'm a socially awkward, anxious loner (involuntarily celibate), so any type of attention confuses me, to put it mildly. Despite being a loner, though, I get the urge to talk to women occasionally. Having no social skills, inexplicable awkwardness makes every single interaction ridiculous and embarrassing. With recent urges, I was just trying to ask some rand...

A Few Irregularities Ch. 01

by Princess_Lulu on Mar 2, 2020
Sci-Fi & Fantasy

Check out the prologue if you haven't yet! Feel free to leave a comment! All characters are 18+ years old. _________________________________ Maggie hummed to herself happily as she pulled her cover over her body, laying her head down on her pillow. Just like she did every night, she grabbed her phone for some mindless social media browsing before bed. She...

Naked Houseboy & his BBW Boss Ch. 03

by write4fun22 on Jun 8, 2020
Toys & Masturbation

*Part 3 in an ongoing series... I pulled up in front of the house and turned the engine off. But I didn't get out of the car right away. I needed a few minutes to collect myself. I looked at the house; the house of the woman who had posted a want-ad for a naked houseboy. It looked like any other house. A well maintained lawn, a recent coat of paint, a flowe...

Poolside Jerk Instruction

by hodownnuzv on Mar 6, 2018
Exhibitionist & Voyeur

Devin sat at a black IKEA desk in the far corner of his bedroom. It was late June and he was back from college for the summer. A humid glare of sunlight split through the open window and reflected off of the lamp beside him. His skin had begun picking up its summer tan for the past few weeks as the pallor of exam stress and deadlines slowly faded into his me...

Working Overtime

by billy_strokes on Sep 14, 2017
Exhibitionist & Voyeur

I spent the majority of my day distracted from my work in a state of constant arousal and it was entirely your fault. On top of that, I'm now stuck here working overtime. I don't know if it was because I was exceptionally horny or what, but everything about you today made me want to cum. Every time you walked by, I couldn't stop staring at your boots and t...

The Guest

by mayapapaya on Sep 1, 2017
Group Sex

It begins with a look I suppose, a nod of the head, a turn towards the stairs, towards an unseen room, and in a moment I know I'll be following them to bed, though I'll wait a few minutes while they gather their things, make arrangements, have the final powwow, but I'll follow soon enough, up those stairs and down the hall, I'll knock gently, politely, on th...