Awkward Stories

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Naked Houseboy & his BBW Boss Ch. 06

by write4fun22 on Jul 13, 2020
Toys & Masturbation

*Part 6 of an ongoing story... We stood there for a moment, locked in a handshake, across the table. It was official, I was going to be her naked houseboy. Finally, she released my hand. But she didn't sit down. Rather, she remained standing. "So look," she said casually. "Today's Friday. As such, I'd suggest that your first official day be this coming Mon...

Alice's First Date Ch. 01

by reading_lover on Jul 15, 2020
Erotic Couplings

Ding dong. It was Matt. Alice had been nervous all-day for him to arrive. It was going to be their first date and she was anxious for it to go well. "Hey, come in," she smiled and opened the door wide for him. "Hi," said Matt. That was okay with her, she knew he wasn't much of a talker, she had mentally prepared herself already for what to say if any awkwar...

A Series of Love.

by McPokerface on Oct 16, 2017
Miscellaneous

We've all had our own little love stories. Our first kiss. Our first date. Our first time. What was your first love like? And, was it... Special? Awkward? Perfect? Or... did it go awry? Perhaps, you wanted it to go in a different way? Or perhaps, you've never felt love, only lust? This series of stories will focus on love. On companionship, friendship, and l...

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At The Gym

by john_mo on Sep 12, 2017
Fetish

I was at the gym the other day, and had an unusual experience I thought I'd tell you about. I was at my locker getting changed into my gym gear, I was facing the locker and had my back to the room but had the strangest feeling that someone was watching me. Out of the corner of my eyes I saw 20 something asian guy looking at me. Surely its my imagination...

Awkward Ch. 01

by Amnoartist on Sep 28, 2020
Erotic Couplings

Awkward Written & edited by Amnoartist Prologue Laid in bed, Mark stared longingly at the ceiling. A depressive sigh escaped his lungs. He had an intense desire to sleep but couldn't on account of the noises from the wall behind him - the bed creaking, lusty moans, enthusiastic giggles, a cacophony of sounds that only served to make Mark wince and cringe,...

Freshman Girl Loses Her Virginity

by thirstygirlll on Sep 19, 2017
First Time

Note: This story isn't wild or crazy. It is simply a first time story. If you are looking for a wild first time story (as in, rough fucking, gangbang, lesbian, etc), this isn't for you. It is a slow story based on a real first-time experience from a friend of mine- just a guy and a girl. I hope you all enjoy it! ***** When I went to college, I had just tur...

Kissing Comedy

by iluvmybike on Sep 13, 2017
Non-Erotic

When I was 13 I was totally un-kissable. I had big hair and big glasses and a lisp-causing retainer and I had neither boobs nor trendy clothes to compensate for my awkward misfortunes. My friends would talk about the guys they had kissed, or the guys they had held hands with at those skate-nights where all the cool kids would go and skate around in circles f...

Sandy's One Night Stand

by db733 on Sep 13, 2017
Loving Wives

It all started casual and as much as I tried to make it exciting and hot... the sex was very, very bland -- but the encounter was exciting. I was just out with my girlfriends with nothing in mind and then we saw each other. I liked him and obviously he liked me. I thought he was good looking and liked his body. Of course I was horny. I was extremely horny an...

The Dangers of Thinking

by RemiMarselis on Sep 1, 2017
Humor & Satire

"Is this as awkward for you, as it is for me?" I hope that by shooting the elephant in the room, we'd have a little space to breathe. Horton's internet dating stories never mentioned uncomfortable moments like this. They always started with him being a douche, doing something stupid, and fucking an overweight chick with big knockers. I shoot a glance at Tam...

Neraph

by taniamittal01 on Sep 16, 2017
Transsexuals & Crossdressers

My name is Neraph (a trap) and I am a 25 years old tall and skinny guy, with long black hair (really long, as they haven't been cut since I was 10). I wear specs and I look nerdy. Being a shy person, I never really had friends. I was more into music than anything else. With a rock band, I could easily carry my long hair which had reached my back, without get...