I was at a hotel by work for the night when I logged into Grindr and saw a guy that looked familiar. Older guy, fuzzy faced and a sinister smile. One of those smiles that you crack after silently sharing a dirty joke in the middle of polite society, getting away with some naughty but not breaking the rules of propriety.
We didn't get to meet because even though he was in the same hotel, he was there for some sort of seminar with a business partner. So we just chatted off and on and then that night I finally asked something that could either make me look like a fool or would blow him away if I was correct.
His little screen name mentioned his name and his love of the arts, which is what prompted me to ask. He looked pretty similar to what I remember as one of the first guys I've ever played with. My sexual partners at that point were in the single digits. I could count them on one hand, I'm sure at that point. Hell, I was only fourteen. Maybe fifteen. But I remembered his name. One of those details that are etched into your mind being one of your first times where everything was fresh and amazing. Overexposed vivid colors burned into your skull. The guy I was thinking of I met at a coffee shop in West Hollywood while I was waiting for my friends at the bar next door. Just people watching. That is, until he came in. Leather jacket. Full beard before it was trendy, before bear was a ubiquitous term of coveted desire. I was sexually precocious. I mean, I used to bypass the regular porn rags for titles like Bound and Leather and always seemed to get sprung passing by a Tom of Finland sketch. So this guy immediately caught my eye. And I caught his as he did a double-take when he passed by. We had exchanged numbers... it must have been numbers. pagers and mobile phones weren't quite as popular just yet. And then I ended up spending a night at his place the following weekend.
So, I asked.
"Hey, weird question, but did you have an art studio in Reseda back in the early nineties and drive a beat up truck... And live in the studio on a bed on the floor. Do art with a dot motif...?"
He was blown away. That was indeed him. But he wouldn't give me a straight answer when I asked if he remembered me. I'll come to find out later that he didn't. He came back to the hotel a couple days later and we took two hours to catch up and I finally got it out of him. He completely doesn't remember. Kinda funny but his Grindr profile noted he's still into younger guys. And he's still a top. I don't think I look too much different from then, but I do know my body type is different. I was a really skinny kid so I'm kinda toned and beefed up now. And I'm more top than anything else these days. I wasn't sure we'd still be sexually compatible, but in his words, "I'm not too worried about that."
I spent awhile inwardly laughing at how much he's remained the same. Still a bit of the scattered bohemian type with kid-like tendencies of being completely enraptured and excited over things as well as incessantly distracted. Even now, in his sixties. I think I tripped him up a bit as I confidently picked him up and walked him over to the bed, bear hug from the back so that he can feel my hardon pressing into him before I tossed him on bed. Then I undressed him and played with his body, gently caressing him until I felt like he was properly relaxed. And with our eyes locked, I worked my raw cock up inside him in an agonizingly slow roll of the hips as I felt his hole spasm and relax around my cock.
"No way. How the hell are you doing this? How can it be so easy for you?"
I answered by slamming the remaining inch into him with a hard thud, making him groan and clench down and roll his eyes back all at the same time.
Unfortunately, with a guy that tight, I didn't last long. I felt every time his hole involuntarily squeezed around my cock and instead of having that push me out, I pushed all the way. Long strokes for him to feel my length. Small strokes to reach as far into him as I could. And when I felt like I hit that point of no return, I flipped the switched and just used his hole, folding him over and crumpling him on top of himself as I hammered my load into him.
"I can't believe it was so easy for you to get inside me."
And I smiled that sinister smile, sharing that inside moment. A look reminiscent of his profile pic, as I realized I just finished up the flip fuck that was almost twenty-five years in the making.