Awkward Stories

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The Roommate Ch. 01

by Cordellia on Sep 15, 2017
Transsexuals & Crossdressers

I had only just moved to the city, moving into an apartment with my best friend from school, Ryan, when he had got a job offer in another city. Ryan hated his job and the offer was too good to refuse, so he had to go - and I had a month to find a new flatmate. But three weeks passed, and still no one replied to my online flatmate wanted ad. I was starting to...

Fun at the Library

by TheGoodGirlS1ut on Apr 4, 2018
Exhibitionist & Voyeur

It all started a few weeks ago, when I first realised I was attracted to my best friends ex one night when we were alone in my bedroom since we still run in the same circle. He saw my 5'2 curvy figure in its normal state, my pussy shaved and my 36d breasts aching for his touch. That night was unexpected as he ran his hands over my hourglass figure during a g...

Dinner Isn't The Only Thing Getting Done

by aussie_sin on Sep 12, 2017
Erotic Couplings

We are in the kitchen cooking dinner, we are behind the kitchen counter and I am on the floor try to find something in the lower cupboard. There is a knock on the door, you can see it is Stephannie and call her in. She is not one of my favourite people, she is taking up too much of your time and ignores me, I still can't forget the comment you made about her...

Over Your Shoulder

by CobaltDrake on Aug 19, 2017
Exhibitionist & Voyeur

Sitting in a second chair, I roll up behind you, out of your sight unless you turn your head completely. "So, my love, you said things are awkward when someone looks over your shoulder." You start to turn to look, but I rest a hand on your shoulder, lifting your hair with the other, kissing the back of your neck, and as always you are quickly distracted. "Wh...

Velvet Journal Ch. 1

by the1master65 on Sep 13, 2017
Romance

How did I get to here? I'll have to go back to then. Eighteen and still inexperienced. A tall awkward boy who desperately needed to lose his innocence. Well actually I had already lost that due to the chance discovery of hardcore in my brothers bedroom - he was at college and I was playing his records - cool. The Clash, Stranglers, Elvis Costello - a goo...

Craig Pt. 01

by eroticjuggalo on Sep 14, 2017
Erotic Couplings

Just a couple of days after the first time I Chris and I messed around again. This time something was a little different. My longtime friend Craig was partially involved to a certain degree. Craig was a short stocky dude who was about five years older than me. He had around red face and short strawberry blonde hair and my family lovingly dubbed him "Campbel...

Still Crazy After All These Years

by bourbonslut on Sep 17, 2017
Non-Erotic

Finally, after nineteen years, HE dumped ME. What a nerve! So now, the world's longest series of unfulfilled mutual crushes is finally over...or is it? Let me tell you the story. I've known "Buddy" since college, almost twenty years now. He sat directly across from me in the college band, a freshman smugly dropping himself into the first trumpet section. I...

My Mother's Cock

by PanWhoWrites on Aug 5, 2019
Transgender & Crossdressers

Chapter 1 "Please Carl...I need your help." "Mom, this has to stop." "I can't...oh, honey, I can't control it. I just...is this how you feel? Is this how you feel all the time?" "Why don't you go and get Becca to help you out?" "She already did." "Seriously?" "Carl, I am your mother, and I'm telling you - I need you. Now." ### It all starte...

Sarah & Dave Sex in Paphos

by dbevanxxx on Jun 12, 2019
Erotic Couplings

My name is Dave, I recently I went on holiday to Cyprus with my partner Gayle where we own a holiday villa. I am in my sixties and Gayle is a little bit younger in her fifties. Gayle thought it would be lovely to invite her niece Sarah, a single mum of two to stay with us. Sarah is a beautiful, tight-bodied blonde in her early thirties with bright blue eyes...

First Time with Michelle

by eisbehr on Sep 14, 2017
First Time

Michelle was my sweetheart in high school. Blonde hair, petite blonde, round hips and a set of breast to put any supermodel to shame. I remember just the thought that she might let me touch them was enough to keep me excited for days. We had been on a few group dates and had friends in common. We enjoyed each other's company and enjoyed the pleasures that c...