Author: DesignatedDrinker403

[M]y [F]irst Time [Cheating] With Lily

If you want to skip to the action, go to the *****

This story takes place nearly a decade ago when I was 21. For a brief period of time I was sleeping with my OG high school crush, Lily. Lily and I had always been close friends in high school, but owing to my own nerdy demeanor and bad timing with our other relationships we had never actually gotten together during our teens. Like a lot of guys, I didn’t find my confidence until University, when girls started noticing and hitting on me for the first time.

Lily was an absolutely bombshell. 5′ 9″ (somewhat shorter than my 5′ 11″) with alabaster skin in contrast to her crimson red hair and sharp green eyes. Her classic hourglass frame and plush D breasts made her the subject of many people’s attention – guys and girls alike. She was the most outgoing bisexual girl I ever had the pleasure of seeing romantically, and was simultaneously flirty but dismissive in a way that just made everyone around her crave more of her attention. Read more »

Old Memory On A Pedestrian Overpass [MF]

I have a very fond memory of fucking a lover over a decade ago on a pedestrian overpass over a major road in my city.

It was night, and there were no lights on that overpass at the time. She and I had been dabbling in public sex, and when we saw how few people there were in the park I pressed her up against the railing of the overpass.

Hundreds of cars were passing under us, but we didn’t care. We haphazardly got out clothes out of the way, her taking off one pant leg and fucked exactly as you described. It was so stimulating, thinking about what those drivers could see if they looked up and scrutinized our movements.

I made her cum early that night and she was a convulser. It sent me into orgasm but her shaking made me slip loose prematurely, and I ended up covering her pussy in my spunk instead of filling it up as I had intended.

[MF] Getting Handsy On A Train Leads To Fun In The Alley

We’re on a metro train, each going home after having a long day. You just yearn for some relaxation, maybe a bubblebath with a nice glass of wine. The train is slowly getting more cramped. When you got on there wasn’t even room to sit – so you were hanging off of the rail just wanting the day to end. Among the less than enjoyable odors… you catch a hint of cologne. Looking back, you see me seated, wearing a modern shirt with a knit tie, reading something on my phone. After my scent drew you in, your eyes linger, wondering about me.

We come to another stop, and even more people file into the train. An older woman hobbles onto the train, and I promptly get up to give her my seat – moving to stand behind you. The train is so crowded, yet people keep cramming themselves in. Before we depart for the next stop, you find me pressed up behind you. Your intoxicated by my smell, and as I catch yours I find myself equally enamored. Read more »