Harvard Hottie

As I stood alone in my college dormitory for the first time, staring out of the large picture window, I couldn’t believe that it was real. After quite literally a lifetime of working my ass off, I was now standing in my very own room at Harvard College. My parents had said goodbye just five minutes before. Although they were incredibly proud of me, I also knew that they were profoundly uncomfortable being in this place. We were decidedly lower middle class, and the sights and sounds of Harvard were a constant reminder to them that they did not belong in this world. Although they had driven me up to Cambridge all the way from our house in Kentucky, they didn’t exactly linger once my fairly meager possessions had been deposited in my room. In fact, they were so eager to get back on the road that, after giving me a really heartfelt hug and congratulations, they left before any of my roommates had even shown up. To be honest, I think they were terrified what the other parents might think of their Wal-Mart jeans and Payless shoes.
It was a fear I knew well. Ever since I was eleven-years-old, I had lived in a world that felt mostly foreign to me. Just before middle school, after taking a diagnostic and aptitude test at my shitty public school, I found out that I had the highest score—not just in my school, but in the entire state. My parents decided that I couldn’t stay in my local school, and after spending several months working with my grandpa’s Rotary Club to raise some money, they paid for my application to one of the best prep schools in the South, in nearby Lexington. After receiving a full scholarship, my world shifted. Just like that, I was swept out of the hog shit and meth heads of my home town and thrown into a world of BMWs and jaunts to Europe. I had no clue how to respond initially, but really quickly I became really good at assimilating. Although everyone knew I was “less fortunate,” I always kept up with my classmates by taking advantage of every opportunity I could. Everyone else pretty quickly realized that, despite my hick accent, I was smarter than they were, and because I had grown up hardscrabble with the other rednecks, I had a street cred that they actually envied. By the time I graduated as valedictorian, I had figured out how to live like a privileged white boy. Yet, there was always the nagging feeling that I wouldn’t be able to keep up the façade.
Even though it was pretty early, it was already really hot out, so I took off my shirt while I set about putting my boxes over into the corner of the common room. As I waited for my roommates to show up, I looked at myself in the mirror on the door. A three-sport athlete, my body was just about as nice as an eighteen-year-old’s can get. All 6’2” of me was framed nicely by the view of Harvard Yard outside the window. My broad shoulders tapered into my rippled stomach and the deep “v” of my hips. My arms were well defined without being overly bulky, my ass was round and tight, and I was nicely hung. Superficial as it was, I knew that in part it was my looks that put people at ease around me. It was pretty clear that, because of my body, my bright blue eyes, and my light blond hair, it was easy for me to charm people. I didn’t even have to be funny, and people would still laugh at my jokes. It had also made me a pretty big hit with the girls at school, although that quickly lost its appeal. It was somewhat surprising, but when I realized I was more into boys, I actually wasn’t that upset about it. Even though I grew up in the middle of the Bible Belt, my school was progressive enough that being queer was actually something of a social benefit, or at least not much of a problem. I’d also never lacked in self-confidence, so it wasn’t very hard to just tell people to fuck off. I still hadn’t told my parents, but by the time I shipped off to Harvard pretty much all of my friends from school knew that I was playing for the other team.
While I waited, I studied the names of my roommates. I had already looked them up on social media of course, and we’d even exchanged a few messages, but knowing that they were just about to arrive filled me with anticipation and more than a little anxiety. My dorm was a suite, with three bedrooms off of a large common room. Since there were going to be four of us in total, that meant that two of us were going to have to bunk up. We’d all agreed that we would wait to draw straws when we got to campus, so it was still up in the air whether or not I would have my own room or not. Charlie arrived first. I threw my shirt back on as he and his parents entered the room. A sweet, nerdy kid from Ohio, we fell into a fairly easy rapport, in part fueled by the fact that we were both from less-than wealthy backgrounds. Next, Chase walked in. Chase was a track star from Sacramento, and he was friendly if a bit reserved. Now, we only had to wait for Henry to show up…
Henry Maxfield Caldwell. I had studied him online extensively. A quick internet search confirmed what his pictures and name suggested. Family net-worth: 3.6 billion. Current relatives in Congress: three. Body: tan and taut in his impressively filled-out speedo while in St. Tropez. Hair: dark, wavy brown. My cock would instantly thicken when I looked at his photos. I had been with a number of hot preppy boys back in Kentucky, but this guy was on a whole other level. I had to stop checking him out, for fear that I would memorize the details of his profile and end up incriminating myself in front of him. About thirty minutes after Chase, he walked into our room. Perhaps unsurprisingly, the Dean of Freshman was helping him and his parents get acclimated—probably unnecessarily, since the Caldwells had been attending Harvard since the 1700s. Harvard might have a shit-ton of money, but that doesn’t mean that it can afford to ignore multi-billionaires. As the Dean rattled on, Henry introduced himself to us. “Hey man, I’m Evan,” I said, as I grasped his hand. Maybe it was just my eager imagination, but I couldn’t help but think that his eyes lingered on me a beat or two longer than expected.
After the Caldwells left, we got down to the business of dividing up rooms. To my surprise, Henry seemed to be perfectly down with bunking up if need be. In fact, he was remarkably down to earth. “I’m used to seeing people metaphorically blow my dad,” he said with a laugh as the Dean left, “but to be honest, it’s pretty embarrassing. I’m cool with whatever.” We quickly realized that we didn’t have any straws or anything to choose the rooms, so Chase suggested we just rock-paper-scissors it. I already knew how I wanted this rooming situation to end up, so I said we should pair up, and the losers would live together. With any luck, I would be able to get Henry alone every single night. We faced each other for best two out of three, me with Chase and Charlie with Henry. I watched their game far more intently than I did mine, and it came as no shock when I “lost” following two half-heartedly thrown scissors. Charlie seemed pretty intent on winning, and when he threw the final winning paper, he let out a long “yesss.” I wanted to cheer too, but I was composed enough to keep my cool.
Henry actually seemed pretty excited to have a roommate. “Dude,” he said, “I’m so jazzed to be here. I think it’s gonna be a fucking blast.”
“Haha definitely man. By the way, I don’t really have much stuff,” I said, “so you can feel free to take up a bit more space.”
“Really? You’re sure it’s not a hassle?”
“Nah man, when you come from bumfuck nowhere Kentucky, you don’t really end up with many material possessions.”
“Cool! Thanks. I actually didn’t end up bringing very much either.”
“And why is that? It’s pretty clear you’re not exactly hurting for money there.”
“True, but I also kinda don’t give a shit about all of that stuff. I mean, it’s nice, don’t get me wrong, but honestly, I’m sort of terrible at being rich.”
“Well that’s good, cause I’m pretty awful at being a hillbilly,” I laughed. “I ain’t never fucked my cousin or gone squirrel huntin’ or nuthin,” I said, putting on my best “Deliverance” accent.
Henry cackled. “Nice, dude. Hey, you wouldn’t mind if I changed real quick, right?