Awkward Stories

44,618 results
Orientation
Length
Source
Infinite Scroll

Reconnecting with Rene

by dpingjessie on Sep 25, 2017
Mature

More than a year ago, I posted a story that shared a fantasy of mine that I had otherwise kept to myself for the past few years, namely, fucking my older female boss over her own desk at work. While I found the woman, Rene, anything but sexually attractive when she first hired me (if for no other reason because she was in her early 50s and I in my mid 20s),...

A Shameful Sentence

by ValerianXIII on Apr 27, 2016
Fetish

I was still in shock from what the judge had said, 6 years under my stepmothers care. I couldn't believe it but there was know way I could pay for the property damage and my stepmother was the only one who could. My stepmother and I never got along, in fact we hated each other. When I found out my stepmother would pay for the damages I knew it was a bad deal...

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Virtually Yours Ch. 2

by FeJuggler on Sep 13, 2017
BDSM

The morning grass was still damp but he didn't notice as he walked across the park. His pace was just a bit fast, as if he were in a hurry but forcing himself to appear relaxed. The playground equipment was deserted; the children were all in school, and it was still too early for anyone to be enjoying their lunch beside the small lake. Only one other person...

Trust Fall Ch. 04

by tessquince on Sep 16, 2017
Novels and Novellas

Trust Fall Book One of The Trust Trilogy Tess Quince Chapter Four WHEN HE PULLS UP TO the valet station the kids manning it all give an eye roll. I see Ben Sheppard smile at that. I open the door and one of them helps me down. Ben hands another valet his keys and I see him tip a twenty and say in a low voice 'for the truck being such a hassle'. The vale...

Choose your own SexVenture Page 21

by topwise on Sep 16, 2017
Novels and Novellas

Disclaimer: This is part of a larger adventure story. If you reached this page as part of a reader's choice from a previous page, continue below. If not, CLICK HERE to start at the beginning of the SexVenture. = = = = = Page 21 = = = = = You regain your composure after your orgasm and give a kiss to the person you hope is still on the other side of the...

Cindrellas Kiss Ch. 01

by maanmathan_playboy on Sep 16, 2017
Transsexuals & Crossdressers

For a long time, I wanted to be a GIRL. I love to be feminine, cute and a bit sexy, at times! It wasn't surprising that the fairy tale princess wooed me to the core, for they were all that I wanted to be! But, I never ever imagined I am going to be one such girl in my life time even though it's only for a short while. Everything started during my college st...

Meeting Katie

by Asaccharum on Dec 10, 2018
Erotic Couplings

I sat at the bar, slowly sipping my beer. It was a cold winter night. Patrons entered with glowing red cheeks and chilled fingers. None of the people coming in thus far were the person I was here to meet though. Where are you, Jake? I thought. I pulled out my phone. A new message. Thankfully. Car problems. Rain check, next week? read the text. With the ev...

Discovering Her Cum Fetish

by TempestWhirlwind on Oct 12, 2020
Fetish

I get a text from the ex, "Am I bad at giving blowjobs?" Weird question. The erotic memories flood back. She was always generous on the fellatio end of the relationship. But things didn't work out between us. "Of course not", was my reply. Followed by, "Why?" "Well this guy I'm dating usually stops me mid head to fuck me instead", goes the response from...

The Teacher and the Electrolux

by TheWolfNose on Oct 3, 2018
Mature

"When you're in a position of power, people will always, eventually, inevitably get a crush on you. As a teacher, you have to learn how to resist it and redirect it - these young adults all have two things in common: they did something stupid and were kicked out of their schools and are trying to get their GEDs, and their hormones are still going crazy. Do n...

Saundra

by geraldf on Sep 13, 2017
First Time

At the time this story happened, I was working as a freelance proofreader for several small publishers in New York. I had come to this particular building on Fifth Avenue to pick up a job. I had always enjoyed coming to this building because it housed one of New York's biggest modeling agencies, and I almost always shared an elevator with one or two models w...