The Guest Room – Chapter 2: Night Games

Everyone is 18.

Note to readers: Today I've included the full audiobook of this chapter. Feel free to give feedback in the comments section: love it, hate it, needs a tweak for your preferences, etc. This will act as a preview (and beta test) of an upcoming Audio-inclusive Tier, which is currently in the works (still tweaking the voice). Stay tuned, and enjoy! Cheers.

Chapter 2: Night Games

Days passed and we did not talk about the event on the couch at all, where I came right on his face, even watching him inadvertently swallow some of my cum, all in the name of a prank. He took it well that night, and acted completely normal after that, except I would catch him looking at me out of the corner of my eye, then look away when I glanced at him.

“You good?” I asked, one day when I was standing in front of the fridge looking for a snack, and he was standing in the kitchen doing literally nothing, but he was looking at me.

He shrugged. “Just stretching.” But, he didn’t look away, and he wasn’t even stretching. He followed me into the living room. This big, dumb jock with a huge cock somehow adopted some stance toward me, almost like a beta?

We sat on the couch and started the new episode of White Lotus.

“Hey,” he said suddenly, interrupting a scene where the brothers were talking about unspeakable things (depending on what outlet you’re on). “You ever wonder if any of this is, like… too far?”

I blinked. “The pranks?”

“Yeah. Or like… everything.”

His voice was softer than usual. No smirk. No punchline waiting.

“Sometimes,” I said.

He didn’t answer. Just kept looking at the screen.

Then, without warning, he leaned in — not much, just enough that I could feel his breath on my jaw. My heart was hammering, and I didn’t know why. His hand came up — like he was going to shove me, maybe roughhouse like usual — but it landed lightly on the back of my neck instead. Not pushing. Not pulling. Just… there.

I didn’t move.

Neither did he.

For a few seconds, we stayed frozen like that. The heat between us rising in the silence. The jokes, the rivalry, the boundaries — they all felt distant now. Like they belonged to different versions of us.

“Dude,” I finally whispered.

“Yeah,” he said, not moving.

But, I couldn’t think of what to say. He moved his hand down off my neck, wrapping an arm around me, holding me like I was a girl on a date with him. We were basically snuggling, and I leaned back against his chest. I could feel his pecs move against the back of my head when he shifted his body. It was nice, like a better version of just hanging with the boys. We watched the rest of the episode together on the couch, until I fell asleep like that.

–[]–

A couple nights later, I woke up to the bed shifting, the weight of him pressing into the mattress beside me. My brain was still foggy with sleep, but I could feel his body heat radiating against my back, the faint scent of his skin — musky, warm, familiar. Then, before I could even process what was happening, his hand slid between my legs, his fingers pressing firmly against the sensitive skin of my inner thigh.

“Riley,” I mumbled, half-asleep, I knew it was him before I was aware of what was happening.

Then I felt it–his flesh pole pressed between my butt cheeks. I was still half asleep, but I started laughing.

"Ok, you got me," I said, "You fucked me. You win, go back to bed."

But he didn't move.

My chuckles turned to silent awareness as he started rubbing his rigid, hefty shaft up and down between my perky butt cheeks. I knew I had a lot of meat to work with back there, but I couldn’t believe he was doing this. My thoughts were on fire. Is he actually rubbing his boner up and down my MALE ass just to get me back for a prank?

His other hand gripped my hip, pulling me closer, and I could feel the hard length of his cock pressing against my hole now. My body reacted before my brain could catch up, a shiver running down my spine as he shifted slightly, the head of his dick rubbing against my ass. It wasn’t aggressive, but it wasn’t gentle either. It was… intentional.

“Are you gonna” I started, but the words died in my throat as he pushed forward, the slickness of his pre-cum smearing across my skin.

“Yeah,” he breathed, his voice almost raspy, guttural.

I didn’t resist. Not when he grabbed the lube from my nightstand (don’t ask me why I keep lube there), not when he spread my cheeks apart, not when he pressed the head of his cock against my hole. My heart was pounding, my breath coming in shallow gasps, but I didn’t stop him. I couldn’t. Something about the way he was touching me, the way he was holding me, made me… want him.

The first push was slow, almost hesitant, but I could feel the tension in his body, the way he was forcing himself to hold back. It hurt — god, it hurt — but there was something else there, something deeper. A strange mix of pain and pleasure that made my head spin.

“Fuck,” he muttered, his voice strained. “You’re so fucking tight.”

I clenched my teeth, bracing myself as he pushed deeper, the stretch burning but somehow… good. I could feel every inch of him, the way he filled me, the way he made my body react. It was overwhelming, too much and not enough all at once.

“Riley,” I gasped, my voice trembling. “I can’t…”

“You can,” he said, his hands gripping my hips tighter. “You can take it.”

And I did. I let him bury himself inside me, the pain slowly giving way to something else, something intense and all-consuming. He was moving now, his hips rocking against me, each thrust sending a wave of pleasure through my body. I could feel the heat building in my gut, the way my cock was throbbing, desperate for release.

“This is… fun,” he said between breaths.

I didn’t respond, but I started to lean into his thrusts. Picturing myself as the girl getting fucked in the plethora of porn that had satured my brain was giving me tingles down my guts.

“Fuck, fuck, fuck,” he chanted, his pace quickening, my butt cheeks bouncing on his large cock, his breath coming in ragged gasps. “You feel good on me.”

I couldn’t speak, my body trembling as he fucked me, each thrust pushing me closer to the edge. I reached down, wrapping my hand around my cock, stroking myself in time with his movements. It was too much, too intense, but I didn’t want it to stop.

“I’m gonna…” he started, but I cut him off with a strangled moan as I came, my body convulsing as I spilled onto my bed. He followed moments later, his hips jerking as he emptied himself inside me, his grip on my hips digging deeply into my flesh, almost painful. I could feel the pulsing, and I just noted the sensations in the afterglow of my powerful orgasm.

We collapsed together, breathless and sweaty, the weight of him pressing me into the mattress. I could feel his heart pounding against my back, his chest rising and falling in time with mine. Neither of us spoke, the silence heavy with everything we hadn’t said. But then, his dick still buried balls deep inside me, he started laughing. It took me a minute to get there, but I started chuckling too. After cumming, the dick needed to go, and I squeezed him out of my ass myself. 

Finally, he rolled off me, the cool air hitting my skin as he moved away. I could feel his cum leaking out of me, and my ass was wet with a mix of our sweat, along with some spit and cum and lube. The mess we’d made was a pungent reminder of testosterone-fueled drives gone too far, but I couldn’t bring myself to care about it. My mind was still spinning, trying to process what had just happened, and wondering why it was funny.

“I…” I started, but he cut me off with a laugh.

“Don’t,” he said, shaking his head, his voice light, almost teasing. “Just… don’t.”

I turned to look at him, his face flushed and red, his eyes watering a bit from this strange laughter we were sharing, his hair sticking to his forehead. He was grinning, that same cocky smile that used to make me want to punch him. But this time… this time it felt different. Like there was something more behind it. I looked down at his floppy, manly, big cock resting in a wet spot on his thigh. 

“I can’t believe you did that,” I said, still catching my breath.

“I can’t believe you took it like that,” he retorted.

“You’re such a dick,” I said, but there was no bite to it.

“Yeah,” he agreed, his grin widening. “But I think you like it.”

I didn’t answer, but I didn’t need to. The truth was written all over my face, in the way my body responded to him, in the way my heart was still racing just from sitting this close to him.

He stood up, his teen jock ass bouncing with his steps as he walked out of the room.

I lay there for an hour, thinking, meditating, contemplating what happened. Would I escalate this somehow? Is it even a game? Did I actually cum from that?

I thought about his family situation. His Dad was broke, and he couldn’t even afford real life, which is why Riley was even staying with us. Maybe I was less than patient with him when he first moved in, but also, maybe the little prank war leading to testosterone fueled cum games were helping him? Maybe?

I got up, put on some underwear off the floor, and went to the guest room door, thinking about talking to him. I paused, since I couldn’t think of what to say yet. Maybe I should just “prank” him back instead of thinking of what to say, I thought to myself. I went back to my bed, and opened my phone to text him, but I saw the text bubble pop up, and waited to see what he would say, but then he didn’t send anything. I went to sleep, thinking deeply about everything, actually, excited.

The next morning, he was out of the house before I woke up, I noticed my sheets still smelled like him, the memory of what we’d done lingering in the air. He had released sweat and other bodily fluids all over it, so I should’ve expected it. I didn’t know what it meant, or if it meant anything at all. All I knew was that things between us had changed, and there was no going back.

When he came home that night, he didn’t say anything about what had happened. He just flopped down on the couch next to me, his arm and shoulder pushing against mine as he grabbed the remote. It was a normal couch stance for guys to sit in, but we both knew something was different. We were closer at least. It’s more than a prank to stick your dick in a guy’s ass. 

“You owe me one,” he said, his tone casual, like he was talking about a borrowed sweatshirt and not… whatever the hell we’d done.

My lips curled. “And I’ll give you one.”