Awkward Stories

44,618 results
Orientation
Length
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Infinite Scroll

Your First Time Ch. 01

by holy_horny on Sep 17, 2017
Exhibitionist & Voyeur

You arrive at the bar at 9 PM, as instructed. The joint is dismal, with only a few cars parked out front. This both relieves and disappoints you somehow. Upon entering, you find he has already arrived, sitting in an intimate booth near the back. He spots you immediately, rising from his seat, but does not come over to greet you. You find this odd, but smil...

Subman and Condiment Girl Ch. 01

by love_neverfails on Sep 14, 2017
Erotic Couplings

It's not like I ever really expected that much. I fully understood that, even though you wanted me, you were still involved with someone else. This time, though, the first time, you were mine. It was the first weekend you came down to see me. Sure, you used the excuse that you wanted to skateboard but I know that what you really wanted was to see me. So ma...

Wet Dreams

by TheNextGamer on Jul 15, 2018
Fetish

For two entire weeks, you, John Doe, have researched tirelessly on a place that historians and philosophers have secretly called... The Labyrinth. A special location that links the psyche of every living being on Earth. The place where you can traverse in people's dreams and do whatever you've wished. Out of sheer luck, you've managed to find a way to enter...

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Fear is Gone

by ToranAllaires on Mar 17, 2020
BDSM

She sucked in her breath as the cold January air hit her in the face. Closing the club door behind her she reached in her purse for a cigarette and glanced up to see the little designated smoking area already occupied. He blew smoke and chuckled. "The birthday girl." "How do you know?" She lit up and regarded him in the cold overhead light. "You were the...

Free Use For All

by GrandoArdens on Aug 8, 2020
Fetish

Guy was hunched forward on his couch, lost in the cruel, cruel world of Yarnham. Every muscle in his body tensed as Rom the Vacuous Spider crushed his character with a meteorite for the tenth time that day. "Jesus, babe! That boss just fucked you harder than Buddy's fucking me!" Guy's girlfriend, Judy, was bent over the back of the couch beside him...

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Tokyo Train Pt. 01

by DJSiddy on Oct 15, 2017
Erotic Couplings

ONE She only knew this guy for the last few weeks. Working in a city like Tokyo made other foreigners stand out easily. They met in passing on the subway to work. He was new to town and just started working in the same building. By some off chance he picked her carriage to share the commute. She always had the same spot on the train. She is a workaholic,...

It's Everything

by kittybeaver on Jul 4, 2018
Erotic Couplings

It's going to hurt. Tomorrow with every step she takes, she will feel it. Not pain, not really. It'll be a stiffness in her legs, an awkward gait. It'll be a reminder of how the muscles of her inner thighs were stretched just past their limits. But the discomfort will hardly matter, because tonight the pleasure feels so good. And, yeah, part of that's the o...

Fucking My Ex

by LuisSuarez on Sep 14, 2017
Erotic Couplings

"Is that it?" We stared at each other. Dara and I hadn't seen each other in a year, and while the attraction was still there, our reunion-an awkward conversation over coffee, and then an even more awkward drink at her place seemed forced. I had caught her glancing down at my crotch when she thought I wasn't looking, and she had caught me quickly glancing at...

The Diary of Mark Jones Pt. 04

by NeoBard on Sep 16, 2017
Letters & Transcripts

TUESDAY 6th JULY We kissed tonight, Sandy and I. It pains me that this means it's a significant event. It should be as natural as holding hands right? But it isn't. The kiss was nice, lips on lip, soft and truthfully, somewhat hesitant. There were no tongues involved, but it was intimate. I enjoyed it even if it was brief. Sandy asked me if I liked it and...

The Good Old Days

by grgor on Sep 1, 2017
Group Sex

Birth Control Pills changed everything. Girls could fuck like guys. Then, later, AIDS changed everything. Fucking became more dangerous again. As a young fucker, I fell right in between. Yes, friends, I was a young fucker in the 1970s. And I did do a lot of fucking. Yay! Yay for the pill! Yay for no AIDS yet! Suzy was fantastic. My first real serious gi...