College was a true awakening for my sexual life. Prior to (and during) college I presented as straight and masculine as they come. I learned a lot about myself through quite a few female partners in that time. But one thing always lingered in my mind without ever acting on it.
As time went on, I'd found myself being more and more turned on by masculinity. I started with only seeking out porn with men that had larger cocks. Then came a transgender porn fetish. Then came full-blown gay porn.
Then the realization that I wanted to bed men, taste them, be fucked by them. I couldn't get it out of my head, but for years I never acted. Until the New York trip in my final year of college...
I wasn't certain about going on the trip, although most of my peers were committed to going. I finally pulled the trigger at the last moment, but this meant that most rooms were accounted for. I found out that I'd be rooming with the last student who didn't have a roommate, Richard.
Richard was what most would describe as the ideal twink. Slim, but not scrawny, clean face, plush lips. I'd never thought of him in my sexual fantasies of men, but once I knew we were in a room together, those thoughts took over my brain. Richard was always kind but we'd never hung out outside of parties. Needless to say, I was jittery at the idea of sharing a room.
Our first day there was spent travelling and then a dinner with all the classmates. Some were still under 21 like Richard, so while the rest of us were drinking at the dinner, the younger ones funnelled out with an of-age classmate to fetch alcohol for the night. The rumblings at dinner were that the others went back to the hotel to drink and "our plan" was to go clubbing. My dirtier thoughts got the best of me. I told my friends I was going to head back to the hotel while they enjoyed a night out.
I bought a few bottles of tequila and headed back to the rooms to find the party. It turned out that the younger classmates were drinking, but slowly struggling to keep awake. By the time I got there, two girlfriends who were approaching a black-out drunken stage were in my room with Richard who seemed to hold his booze well.
Shortly thereafter, I did the responsible thing and got the ladies back to their rooms.
"Okay, bedtime for you girls." I said as they leaned on each of my shoulders.
I expected Richard to turn in but to my surprise he was still game.
"Hey, can I open up this other bottle? We shouldn't turn in so early on the first night right?" he said.
I smirked at him and said, "Absolutely, I'll be back"
I dropped the girls and returned to mine and Richard's room hearing the sounds of the shower and no sign of the bottle. I began to roll a joint as I assumed Richard had changed his mind on staying up. As I licked the rolling paper and sat by the window, Richard exited the bathroom.
"Tequila tiiiiime" he said flamboyantly.
I laughed.
"Wow, just had to do a quick mid-drinking shower? I guess I'll hold onto this joint for later then."
At that point I noticed Richard standing, only in his tight briefs and a towel around his neck, the generous bulge the Richy was sporting. I tried to pull my eyes away, but he must've known what he was flaunting.
"Noooo, let's smoke now! Yeah?" He insisted as he bounced onto my bed.
"I'm down. Just come to the window so we don't make this place stink."
I was sitting cross-legged on the floor as he walked over, I glanced up at the obvious bulge but stared away before he sat. Well, actually, he slammed down in a bit of a drunken stumble.
"Okay, my turn on the bottle, I've got to catch up to you." I said.
He giggled and watched me take 2 big swigs out of the bottle. I put it back down between his legs. I was trying to be discreet, but there's probably nothing discreet about a drunk guy placing a bottle inches from a bulge he can't keep his eyes off. I kept glancing between his eyes staring at me and that bulge of his while I lit the joint. I took a big puff and passed it. He inhaled deeply before being very forward.
"You know, you sure stare a lot for a straight boy..." He said while looking me up and down, passing the joint as our shoulders touched, leaning against the window.
I was so caught off guard, I'd never openly expressed anything like this but my inhibitions took over.
