So there I was, just a dumb country kid who moved to the big city for college. This was some years ago, back when MySpace was a thing and The Best Hookup site ever created. I was lonely, still nursing a broken heart from being dumped by my high school sweetheart. I’d used MySpace with success a couple of times to hookup and I was, well, curious about guys.

So one night I went looking through profiles of nearby gay guys who were single and interested in dating. That’s where I saw ‘James’ for the first time. Honestly he looked like a girl, a beautiful girl with long dark hair, dark eyes, pale skin and cute glasses. I hit him up and we hit it off. We flirted casually and started talking over the phone (cause that’s what we did, back in the day, kiddos) once he said he was down to meet up we set up a time.

James lived with his mother and stepdad, he was such a pretty idiot because he gave me his home address and agreed to let me pick him up in my car. Damn gorgeous fool, tbh. It was around 10 when I picked him up, he was much prettier in person and very sweet. He got in and said we could drive to a nearby spot. This guy had me drive him to a (shit-you-not) church parking lot. When we got there I was horny already and eager to see if this was a thing I would be into, and like the young awkward idiot I was I kinda rushed into a kiss.

He recoiled and said “Wait! Can we just talk for now?” I felt like such an asshole (because I was, that was a dickheaded thing to do) and I apologized and then we just talked, for like an hour and a half, about everything. Life, college, work, movies, relationships, and just whatever. It was a lot of fun and we we’re getting along well and suddenly we were flirting and laughing. He complimented me on my eyes and little stubble beard, said I looked manly, and that he really liked manly men. I told him I happen to have a soft spot for beautiful people and guys, fellas… he was absolutely gorgeous.

We started to rub each other’s arms and the way his soft hands felt on my arms instantly drove heat into my groin and I felt myself growing. I stroked his face and leaned in close to his face, he did not recoil. I asked him “James, I really like you, do you think you would mind if I kissed you now?” He blushed and smiled with some mild outrage at my audacity, but he cut those pretty dark eyes at me and he said “No, I don’t think I would mind.” I barely let him finish before I started to kiss those sweet lips. I could feel a bit of stubble on his face as I stroked it and kissed him. It felt weird and good, and his lips were so soft. He was incredible.

We were all over each other, kissing and licking and rubbing, it was so hot and intense. Eventually I began to rub his crotch, he moaned softly and I stopped and asked “Is this okay?” “Yeah, can you take your shirt off?” I grinned at that sexy little bitch, “Yes,” I said, “if I can take yours off.” He agree I tore my shirt off and he immediately began kissing and rubbing my chest, like no woman had ever done, and I hastily pulled his shirt off and began to rub his back and grope his ass. It got hot and heavy there for a bit, eventually we were in my back seat in our underwear dry humping and making out.

We naturally started to rub each other. I realized that his dick was smaller than mine but cute and soft, he complimented me on my thickness and asked to suck me off. I immediately accepted. That boy gave me the most amazing head. He was so fast and attentive. I had never cum to a blowjob before but man he got me there fast as he just fucked my dick with his pretty face. I stopped him before I came. I said to him (and to myself) “I’m getting my dick sucked by an absolutely gorgeous man and I’m loving it!” He smiled and said “thank you.” His adorable little smirk drove me wild. I went down on him then.

Now most of my lover’s remember me most for my good looks and my head. But this was different as it was a dick and I never done this before. But damned if I didn’t try. I went fast and wet same as he had, he said it was nice but to this day I don’t know if he was just being kind or not. He is the only lover I have ever failed to get off. I finished up and then he finished me off. I came so hard into his pretty mouth. When I finished he sat up, opened the door and I stared as he just let this massive load of my cum pour out his mouth onto the church parking lot. When he was done I pulled him back into the car and kissed him and held him.

We stayed there for a while and just enjoyed each others body heat and the sound of our breathing. We got dressed and I took him home, and left him with a kiss and a smile on my face. We hooked up a couple more times. To this day one of my biggest regrets is not sleeping over at his place one weekend when his parents were away.

“James” if you’re reading this, I’m sorry and you deserve better, you’re an awesome human being and thank you for the time you shared with me.