A Raunchy Quarantine in the Woods [MF]

Becca and I met while working for a now bankrupt company. We chatted at office parties and I felt there was chemistry, but I’ve never been the work-fling type. She was an introverted and unconventionally attractive girl from a small town upstate who was really into hikes, farms, animals and things like that. We clicked over old music, mostly, and random things. I had fantasized about pulling her by her brown hair and clapping her thick thighs to some Sade a few times, but never made a pass.

After the company went broke, I figured I’d ask her out to see a jazz band we both liked. She was down. After the show, we had a few drinks and I told her I’d been meaning to ask her out for awhile now and that I had always found her attractive. She blushed, but shortly after that she told me she had this “other thing” she had to go to. I told her we should go out again another time but didn’t make much of it because I wasn’t sure she was interested. I was heavily into dating apps at the time and was used to the dating lottery.

A Raunchy Quarantine in the Woods [MF]

Becca and I met while working for a now bankrupt company. We chatted at office parties and I felt there was chemistry, but I’ve never been the work-fling type. She was an introverted and unconventionally attractive girl from a small town upstate who was really into hikes, farms, animals and things like that. We clicked over old music, mostly, and random things. I had fantasized about pulling her by her brown hair and clapping her thick thighs to some Sade a few times, but never made a pass.

After the company went broke, I figured I’d ask her out to see a jazz band we both liked. She was down. After the show, we had a few drinks and I told her I’d been meaning to ask her out for awhile now and that I had always found her attractive. She blushed, but shortly after that she told me she had this “other thing” she had to go to. I told her we should go out again another time but didn’t make much of it because I wasn’t sure she was interested. I was heavily into dating apps at the time and was used to the dating lottery.

Dating App Cougs: A Miami Night with a Shy Cougar from Brazil [MF]

This happened a few years ago, but I recently found we had each other on Facebook and tried to reconnect. It spurred some memories, most of which are NSFW and I’ll enjoy sharing them below.

I was in my 20s, had just moved to a major northern city, and was very cold and lonely at the time. Most Tinder dates were really off and girls my age seemed to care too much about things I didn’t care too much for. So I was excited to learn that my family was staying in Miami for the holidays. After buying my ticket, I changed my dating app location and started doing some early recon, but I capped the lower age range at 35.

The match was simple and straightforward. No pointless text game. I’d pick her up that Wednesday night for some drinks at Wynwood. Sounds trivial, but that was already a sign of good chemistry for me.