Hi again! I thought that this time I’d tell about how my best friend and I started hooking up.

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Calvin is my best friend. We’ve known each other since middle school, and have always had each other’s backs. He’s been my savior more times than I can count. We met when he saved me from being harassed by a bunch of bullies in class one afternoon. He was also the first person I ever came out to in real life. It was the day before our high school graduation, and I’d written him a letter that was 2 pages long. His reaction was to ask me if I wanted to go get food because he was hungry. He’s known I was gay for awhile, but had let me have all the time I needed to tell him myself. Calvin is just shorter than me, about 5’10”, Dark skinned Mexican, black hair, and green eyes. He has that sort of charismatic personality that people just sort of gravitate to, so he’s great at making friends no matter where he is.

This story takes place during my freshman year of college, probably around early 2003. It was a month or so after I’d given my first blowjob to my semi-boyfriend, Eliot. I say semi-boyfriend, because neither of us was really out at school, Eliot was deeply closeted, and because we hadn’t officially had any conversations around what we were or what we were doing. So, about a month after that encounter, Calvin says that he’s coming to visit. We’d talked about him visiting me at school, but the timing never seemed to work out for either of us. Finally, the stars had aligned and he was going to make the trek up to see me and hang out for a weekend. I was beyond euphoric. At the time, I was incredibly awkward and he was the one person that truly understood me.

Calvin arrived late Friday night, just in time for dinner to be over, so we ended up ordering pizza and just watching movies in my hall’s lounge. We lasted until about 2 am, then passed out in my room, him sleeping on the floor next to my bed with the sleeping bad he’d brought along.

After breakfast the next day, I took him on a tour of the campus, showing him around the various buildings, then we went off campus to explore the record store and movie theatre, where we ended up watching some random movie that was playing. As we got back to my dorm later that day, he seemed to get along well with my hallmates. As I said, charismatic as fuck.

After a movie in the lounge with my hallmates, Calvin decided that he wanted to have a smoke, but he was running low. I told him about a small convenience store up the road we could walk to, and we took off. As we walked, we just shot the shit catching up. On the walk back, we kept talking, and started walking past my dorm, neither of us quite ready to call it a night. We talked about the classes we were each taking. He told me about his latest girlfriend. And I told him all about Eliot and how frustrated I was over not knowing exactly where I stood with him. At some point, the conversation drifted to people we’d been interested in during high school.

“So, Myles, did you ever have a crush on me?,” he asked, point blank, this suave affect to his voice. I was a bit shocked that he was so blunt about it, but after composing myself, I admitted to him that I had, and that maybe it hadn’t actually gone away. We both stopped in our tracks as the air grew heavy around that admittance.

I’d fantasized many times about dating or just hooking up with Calvin, and suddenly that was all out in the open. I was a bit mortified that I’d even admitted that, but he didn’t seem at all phased by it. For a moment, I thought he’d just shrug it off and give me some line about how he didn’t care and how he’s totally straight blah blah blah (as if he hasn’t told me all about his sex life a million times). But that isn’t what happened.

“So you still have that crush then?”

“I, uh, I mean, yeah, kind of…”

Calvin stepped close to me, inches from my face. He grabbed my hand, and moved it down to his crotch. Calvin was hard. And suddenly his face was in mine and we were kissing. He was in charge here, no doubt about it. Something about having a charismatic personality tends to give people a boldness in them, and one I’d seen from him dozens of times before when he’d pursue a girl. But this was new. He wasn’t pursuing some random bimbo, he was trying to take advantage of me!

His kisses were both gentle and forceful, as if he’d wanted this all along as well. After a couple of minutes being lip-locked, he pulled away.

“Dude…” I said. “Are you…?”

“Nah man, you know I’m straight. But I’ve messed around with a couple of guys before. It’s not my thing, but that doesn’t mean I don’t like getting my dick sucked. Besides, I’ve seen you checking me out. I know you want this.” He guided my hand from his crotch and directly into his pants, where I felt his dick for the very first time.

I was beyond shocked. Here was my best friend offering himself up to me on a silver platter. How could I resist?? Again, we locked lips and started making out as if nothing else mattered.

After another few minutes, he pulled away and said the he wanted me to suck him off, so now we had to find somewhere. We quickly headed back to my dorm, but found my roommate inside our room, loudly and obnoxiously playing some online game. Damn. It was already after 1 AM, so why wasn’t the fucker asleep? Or better yet, not here this weekend??

Then Calvin suggested the bathrooms. They had a couple of larger shower stalls with benches in them and curtains, so I thought it would be perfect. The hall was quiet, so I hoped like crazy that no one was in there and that everyone was back in their rooms sleeping for the night so we could have all the privacy we wanted. Thankfully the bathroom was empty, and we quickly made our way into one of the large stalls.

As we got into the stall, we closed the curtain as much as we could, then continued making out some more. It was driving me absolutely crazy. His lips against mine, our tongues exploring each other’s mouths, and our hands exploring each other’s bodies. At one point, he shoved my hand back down his pants and told me to jack him off a little bit. As I did that, he placed his hand on my crotch, feeling my hardness, which drove me even wilder than I already was. While he grabbed me, I pulled my hand from his pants and started unbuckling him, telling him to sit down on the bench.

Slowly, I lowered myself into a kneeling position, feeling up Calvin’s legs and around his crotch. I started slowly jacking him off, and he grew to attention pretty quickly. After a few minutes, I lowered my head and started taking him into my mouth. His dick was about 7” but not too girthy, so he was a lot easier to fit into my mouth than Eliot had been. It didn’t take me long to find a rhythm that he seemed to like, and he was moaning in a restrained whisper, just in case anyone else came into the bathroom.

I continued going down on him for a long time, and every so often he’d pull me back up to kiss me. As I went back to sucking him off, he’d put his hands on my head and guide me, gently, to how he wanted it. His moans were driving me wild, and I started sucking faster and faster, suddenly really wanting him to cum in my mouth. I started playing with his balls, too, and that seemed to make him moan louder.

Finally, I could feel his balls tensing up, and he told me that he was about to cum. This got me going even harder than before, and before I knew it, he was shooting rope after rope down my throat. His cum was salty and thick, and it made me gag just trying to swallow it all. Calvin pulled me up onto the bench beside him, and we were kissing again.

The afterglow didn’t last long, unfortunately, as we suddenly heard a lot of noise. Several of my hallmates came into the bathroom (a guy and 2 girls), and we heard them head into one of the other shower stalls. Thankfully, they didn’t seem to notice the closed shower where Calvin and I were, and they go to their own shenanigans very quickly. As their shower started (the showers are powerful and LOUD, thank God!), Calvin and I made our way out as quickly and quietly as we could.

This wasn’t our last or only encounter, of course. We had many more hookups over the following few years, until we both agreed that it was kind of getting boring (or maybe I just fucked my way out of that crush I had on him for so long), and we stopped hooking up. He still identifies as straight, and he’s married to a woman now (she knows all about our past hookups). But he’s still my best friend. That part will never change. But every once in a while, I like to think back on our encounters and get my rocks off.

I hope you’ve all enjoyed this installment. I have many more encounters with Calvin and with others to write about, and I’ll post those as soon as I can think of which one to write next.