Awkward Stories

44,618 results
Orientation
Length
Source
Infinite Scroll

My Supervisor Seduced Me

by Cleevedreams on Sep 24, 2019
Mature

'Royal Ascot,' in the middle of June, meant a week's agency work on 'silver service.' As a uni student it was a lucrative week. But it meant getting up very early, being dropped off in town at 5.30am, by 'understanding' parents, to catch the agency minibus for the three hour drive south to Ascot racecourse. The second year I'd signed up for the job, Brenda...

The Pub Pt. 02

by DwarfyJoe on Jun 8, 2020
Fetish

After that night with Angela, I waited a week to go back to the Pub. I knew she was leaving just a couple of days after our hookup. That was why I waited until then to take her home. It's a little awkward to have a one-stand with a girl and then run into her at your favorite bar again under any circumstance, especially if that one night stand involved her be...

The Massage Guy

by TessMackenzie on Sep 13, 2017
Erotic Couplings

Nina had a massage guy. She had been seeing Kevin weekly for a year, had started because she wanted to spoil herself and had never really been into mud and wraps and everything else they did at a spa. And because her feet were too tickly for pedicures. Massages were what worked for her. Kevin the massage guy was straight. That had been a little odd at first...

The Pact Ch. 01

by bergec on May 1, 2018
Humor & Satire

Lisa notices the adventuring party rising from their chairs and sweeps over to collect the small pile of weird coins they'd left on the table. The elf and the walking arsenal drag the inert body of their wizard while the dwarf cleric shakes his head disapprovingly and mutters, "Lightweight." She sidles up to the warrior with a big smile and asks, "Hey, big...

Poor Kaity

by NiceDayReboot on Sep 14, 2017
First Time

Kaitlyn was a charity case, and I knew it. Of course, I always held a sense of guilt about that knowledge because I had to keep her from figuring it out. Oddly, for how often I'd acted as a surrogate older brother to her, she was a year older than me at nineteen. She'd been held back at least once to my knowledge, making her a junior when I was enrolling in...

Provisional Trust Rewarded

by onlyinadream on Sep 16, 2017
BDSM

How did I end up like this? Blindfolded, hands tied behind my back, lying on a bed, in a house I had never seen before tonight? Why am I enjoying this so much? Damn the internet. How could you really trust someone that much? Enough to allow them to blindfold you, strip you, tie your arms behind your back? And on the first real date? We met so long ago that...

Caught Masturbating in the Office

by shooter1923 on Sep 12, 2017
Erotic Couplings

I had tons of work to do, so I decided to head into the office late on a Saturday afternoon. The office was a ghosttown on most weekends so I expected to be alone. Nevertheless, I decided to do a quick sweep of the office just to make sure. As I rounded the corner of our marketing wing, I was stunned by the scene laid out before me: our marketing director,...

Office Heat Ch. 01

by SandieQUK on Sep 12, 2017
Erotic Couplings

The business floor was in darkness, except for two partitioned offices at opposite ends. At his desk in his own partition, Greg leaned back in his chair as his monitor finally showed the upgrade was complete. He hadn't needed his light on, the screen providing all the illumination he needed. At last, he could relax and go home, so he begun shut down. As h...

Cancelled Date Night Ch. 01

by kinglem on Sep 16, 2017
Transsexuals & Crossdressers

Dave was starting to get anxious. The tv was on in front of him but he barely registered what was on the screen. His eyes spent most of the time glancing desperately at his phone on the armrest next to him, yet every time he unlocked it the same disappointing clock face shone back at him. No new messages. Sarah was now an hour and a half late. It wasn't too...

The Park

by Aswrite03 on Sep 13, 2017
Erotic Couplings

There was going to be a major bill to pay at the dry cleaners, but it was definitely worth it. At least that was Cady's thought as she walked back to her car, knees still shaking slightly, heart still racing. She'd lost her bra somewhere in the bushes, and her underwear...well, that had been a lost cause almost from the get-go. All because of one drink at t...