This happened just over 10 years ago, so I’m attempting to pull the details from memory as best I can.

I was 22, fresh out of college, on a break from my long-time college girlfriend, ostensibly to determine if we could live without one another or not. I suppose that translates to—we were each going to get all the meaningless flings out of our system before settling down.

Now remember, this was way back in the early 2010’s, so the online dating scene was less toxic, CL casual encounters was still live, OF had not yet come to be, and Ashley Madison was still a place where you could meet frustrated MILFs on the brink of divorce… for FREE! That last sphere was where I met “Trina”. I made my little free limited account and “winked” at a bunch of people. Memory’s a little foggy here, but I think in those days you were able to exchange 1-2 messages for free before you hit the paywall on the platform? That’s what we did: exchanged a couple of messages, shared our (burner) email addresses and then moved the convo off AM.

Trina was a successful professional in the LA area with a dead bedroom, great tits, and a desire to find some sexy young arm candy to flaunt at her friends. I was basically looking to try all the stuff that my girlfriend wasn’t willing to do: butt stuff, cumplay, facesitting, etc. We spoke on the phone once to discuss what we were each looking for and then agreed to meet at a bar. Her only request was that I bake the ol’ clams for the week prior to ensure I’d have plenty of stamina for the adventure ahead. I was nervous the whole time on the phone, I’m sure my voice was quivering. And when we made plans to meet up IRL, let me tell you, my heart was POUNDING. I had never done anything close to this before and it was a huge fantasy of mine. I spent the whole week drifting off into fantasyland, calling upon every ounce of inner strength to avoid touching myself.

Eventually the evening came. I put on my favorite Canadian tuxedo and rolled out, head still spinning with anticipation. As soon as I got there, I ordered a bourbon on the rocks to steady myself and sat down at the bar, scanning the room as I sipped my drink. Honestly cannot remember anything about the bar aside from the neon lights and mid-century rock wall (you know the one). I’m sure there were other people there, but all I remember is the cute blonde near the door who appeared to be trying to make eye contact with me. Must have walked right past her on my way in. Eventually I got the hint and made my way over to her table, “Are you Trina?”

Again, sorry, memory is failing as to the actual content of the dialogue, but let me tell you, this woman was READY and not trying to waste any time. In probably less than 30mins, we decided to settle our tabs and go out to her X5. Didn’t even mess around with the front seat—went straight into the backseat and started kissing. Soon her hand was on my crotch, rubbing my cock through the denim. I had been hard since I sat down at her table, so quickly my pants came off, and Trina hooked it up with the dome action. I rested one hand on the back of her head as she bobbed up and down and with the other, I started exploring under her dress. No underwear (yay!) and her pussy was already dripping wet. I glided over her engorged clit for not very long before Trina let me know she wanted the dick.

We ended up fucking in the back of Trina’s X5 (safely of course): her sitting on the bench seat, legs spread wide, me kneeling on the floor thrusting away. The vehicle was definitely rocking and, in my mind, the bouncer posted outside the bar must have known what was going on. I mean her vehicle was less than half a block from the entrance!

Afterward, we made out for a bit in front of the bar and then made plans to hang out again. The next time would be at her house in Beverly Hills, which unfortunately offered a couple of not-so-sexy surprises. If y’all enjoyed this story, let me know and I’ll post the next adventure sometime soon.

Thanks for reading and for letting me get this off my chest. Never told anyone before!