My Shy Roommate's First Time

My Shy Roommate Oliver is gay

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Pt 1. Caught Him Staring

So, college life’s a trip. High school feels like it was a lifetime ago, and here I am, living in this tiny room with some dude I’ve never met before. Sure, I’ve had roommates before, but this one? This one was different.

I mean, we’re the same age—21—but we’re worlds apart. I’m used to being around people who know how to hold their own, but Oliver? Well, he’s the opposite. This kid’s a walking contradiction. Nerdy, sure, but not in a way that makes him invisible. He’s got this thing, this quiet confidence, like he’s trying to hide but can’t fully pull it off. And it’s not like I’m some social butterfly either. I’m a bit of a jock, but I don’t wear it on my sleeve. I keep it chill, you know? I like being confident, but I’m not the type to flaunt it.

So yeah, Oliver. My new roommate.

I’d figured him out pretty quick. Guy’s shy, kind of reserved. Definitely not the outgoing type. But I couldn’t help noticing little things—things he didn’t think I saw. Like how he’d spend hours on his laptop, scrolling through stuff that wasn’t exactly... subtle. He’d watch gay porn like he was trying to hide it from the world, or he’d scroll through Instagram, liking shirtless guys like he was the only one online.

It’s funny, really. He doesn’t know that I know.

I don’t think he realizes that I’ve caught him in moments where his guard’s down. Like the other night when I walked past his room, and the door was cracked open. I could hear the sound of him typing on his laptop, his fingers clicking away, and for some reason, I just had to peek.

And there it was. His screen was filled with something I’d definitely never expected to see. His porn history wasn’t exactly a secret, but when I saw what he was watching, I knew I’d caught him in his most vulnerable state. It wasn’t even the porn that made my pulse race; it was the fact that I knew he had no idea I was aware.

I mean, he’s been acting like I’m just some guy he has to live with. Nothing more. But I know the truth. I know what he’s into. And honestly? It gets to me.

It’s not that I’m against it—I’m not stupid. Hell, I’m not even mad about it. I mean, I’m into guys too, just not exactly in the same way. But knowing Oliver was into it? That twisted something in me. Made me think about him a little differently.

Now, let’s get something straight. I’m not some saint. I’ve seen my share of shit, and I’ve done things I’m not exactly proud of, but something about Oliver, something about the way he tries so hard to hide who he is, it made me want to see more. To see him in those moments when he doesn’t realize that someone’s watching, someone who’s noticed, someone who... gets it.

We didn’t really talk much, me and him. The usual dorm room small talk. But one evening, I could feel the tension building between us, and it was like everything shifted.

I’d just come back from the gym, sweaty as hell, the usual routine. I dropped my stuff on my bed, planning to relax for a bit, when Oliver walked in.

“Hey,” he said, not looking me in the eye, like he always did. “You, uh, need something?”

I just shrugged, wiping the sweat off my face with the back of my hand.

“Nah, just finishing up. You good?”

He nodded, but I could tell he was a little off. His eyes were a little too wide, a little too nervous. And then, without thinking about it, I asked, “You okay, man? You’re acting a little… different today.”

He shifted on his feet, looking anywhere but at me. There it was again—his shy act. But there was something in the way he avoided my gaze. Something in the way he fidgeted that made me wonder if he knew I knew.

“Yeah. Fine,” he muttered, his voice cracking slightly.

I don’t know why I did it, but I pushed. “So, you still doing that thing where you... you know, check out shirtless dudes online?”

His face turned red almost instantly, and that small shift in his expression—like he’d just been caught with his hand in the cookie jar—made everything feel way more real.

Oliver stammered, “I—uh—I don’t know what you mean.”

I gave him a smile that was probably a little too knowing. “Oh, you know. I’ve seen you on Instagram, man. Liking all those pics of guys with their shirts off.” I paused for a second, letting it hang in the air. “It’s cool, man. Don’t gotta hide it from me.”

He just stared at me, wide-eyed, looking like a deer caught in headlights. I wasn’t sure if he was embarrassed, scared, or both.

And that’s when I decided I had to keep pushing him. Maybe just to see how far he’d go. Maybe to see how much he’d break.

“Hell, I won’t judge you,” I said with a shrug. “We’re roommates. Friends. We both know what’s up.”

And then, just like that, the silence stretched on. I could feel the air between us thickening, charged with something I couldn’t quite place yet.

But I knew one thing for sure.

Things were about to get interesting.


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