200th Post! Threesome with My Best Friend

Everyone is 18.

Chapter 1: Swipe Right

I had never planned on doing something like this. It all started when my best friend Mason and I were hanging out on a chill Saturday night. We’d both been single for a while, jokingly swiping through Tinder together, trading misogynistic commentary on their attractiveness. But then he matched with this girl named Lily.

From her profile it was clear she was confident and cool, and she was actually gorgeous in a kind of messy, artsy way. Her profile said she was into "shared experiences" and "seeing where the night goes with two guys."

Mason messaged with her for a while, then raised an eyebrow at me and said, "Wanna go all in?"

"With her?" I said.

"With us," he grinned. "She says she wants a threesome. Two dicks for her to taste."

I laughed, nervously. I’d joked about it before, even thought about it late at night in a vague, fuzzy way, but the idea of doing anything like that, especially with Mason, had never crossed into real life. He was like a brother to me.

But I said yes.

While Mason and I were college sophomores, Lily was a twenty-something and lived in her own apartment, a walk-up filled with plants, prints of famous paintings, and one too many candles. She greeted us in an oversized sweater and nothing underneath. She was clearly experienced with hookups. We had a few drinks, and the mood was light, but inside I was nervous as hell.

I watched Mason as he got the first kiss from her, smiling like he knew exactly what he was doing. His body moved with this fluid, playful confidence. When things started heating up, it didn’t feel awkward. It felt like... a dare.

I hung back at first, watching. It felt easier somehow, to let Mason take the lead, to observe. His body was familiar to me, since I'd seen him do his thing for years, but it was different to see him like this. He was so focused. I'd never seen him hook up with a girl right in front of me before, and it struck me how passionate he was, how comfortable with his body. I stayed close but on the edge, barely putting my hands softly into the mix, unsure what to do with the rush building behind my ribs.

The nearness. The accidental touches. The unspoken energy between us. I didn’t say a word. I didn’t even admit it to myself.

When she started sucking him off, I leaned down behind her to eat her out. Suddenly, Mason moved her body until she was on top of me, sitting on my face. When I opened my eyes, to my surprise, Mason's cock appeared right in front of me. Apparently he wanted to fuck her while I did my thing on her with my tongue. I didn't flinch, and watched as he quickly got balls deep inside her, up close and personal with my own face. I continued licking, but my eyes were full of nothing but his shaft and balls. I literally saw his taint pulse with the throbbing of his cock.

When he started thrusting harder, he pressed down firmly and his balls mashed right into my eyes. No one commented on this, or whether it was gay or not. It was all part of the moment, apparently. The musky scent of man filled my brain, and something switched in me. Instinctively, I moved my face up, so his shaft rubbed against my tongue. I could tell he liked it, because he leaned into it.

He slipped out a few times, I think on purpose, and "accidentally" shoved into my mouth. I was grateful for the plausible deniability, because the immensity of my enjoyment at feeling the hot head of his cock press against my tongue was freaking me out.

We switched positions a lot, and somewhere in the mess of limbs and heat, Mason’s hand found mine.

I don’t know why I didn’t pull away. Maybe it was the wine. Maybe it was curiosity. Maybe it was something I’d never let myself think about before. He didn’t look at me, but his fingers tightened around mine like he didn’t want me to let go.

At some point, Mason shifted, and I found myself suddenly face to face with him. Literally. He was above me, eyes locked on mine, and I didn’t know where to look until I noticed how close his hips were, his rock hard, shiny, wet cock jutting out, standing proudly. I stopped breathing. He kissed me, and I froze. He stuck his tongue in my mouth, and I massaged his tongue with my own.

I saw Lily make a weird face out of the corner of my eye, and excused herself to the bathroom. Mason and I quickly sat up and moved apart on the bed.

We sat naked together, our hard-ons standing strong, covered in sex juices. We didn't talk about the kiss. I just looked at him out of the side of my eye, at his confident stance. 

"Think we wore her out?" he asked.

"Dude, you're an animal."

—[]—

Lily came back and said she had a headache. I asked if there was anything we could do to help, but she said no. She was clearly done with us for the night. So, we got dressed and left. We didn’t talk for the first five minutes or so as we walked back to our dorm. The silence felt loaded, but not awkward, just... heavy.

Finally, Mason broke it. "So... that happened."

I exhaled. "Yeah."

"We got... a lot closer than I expected," he said. He wasn’t looking at me, but his voice was careful.

"Yeah. Me too."

There was a pause. Then he asked, "Why did you kiss me?"

I shrugged, trying not to overthink it. "I don’t know. You kissed me first."

"Did I?"

I nodded. "But I didn’t stop you."

"No, you didn’t."

We lapsed back into silence as we walked the last block to our building.

When we got inside, it felt weirdly quiet. Like the walls knew something had changed. We dropped our keys in the bowl by the door and stood there for a second.

"We never even got off," Mason said.

I laughed under my breath. "Yeah."

"And it’s not like we haven’t seen each other naked before."

"We literally shower at the same gym... and now apparently have threesomes with tinder sluts together."

"Should we go nude?" he said with a grin. "It's just us here."

I rolled my eyes, but I peeled off my shirt anyway.

Something was shifting between us again. Not like before. Not with Lily in the room. This was... different. We dropped our underwear casually, and sat on the couch. He threw some porn on the TV. He knew what I liked, although I was becoming aware that I liked something else now too.

Mason sat on the edge of the couch, fully nude like it was the most normal thing in the world. He glanced over at me, casually, and said, "Wanna just... finish? Together?"

"Fitting end to the night," I said, still trying to act casual.

He shrugged. "You seemed into it earlier. Or was I imagining that?"

I looked at him for a long second. At his relaxed posture. At the way he wasn’t pushing too hard, just... there.

"Fine," I said, sitting next to him. "But I’m not looking."

"Liar," he said softly.

I didn’t respond. Because he wasn’t entirely wrong.

—[]—

We settled onto the couch, side by side. The porn played in front of us, giving us a new plausible deniability about what we were doing together. We didn’t speak, just moved in parallel. It felt surreal, like watching myself jerk off with a guy from outside my body.

At first, we both kept our eyes straight ahead. But after a minute, I noticed Mason glancing at me. Not just a glance. A look that lingered.

Then, without a word, he reached over. Our hands brushed, then paused. He swapped mine with his, slow and deliberate, like it was a natural step and not the strange, intimate thing it was.

Part of me thought I should’ve pulled back, laughed it off, but I didn’t.

His hand stroked my cock, and it felt like heaven. I wrapped my hand around his shaft. It felt so thick in my hands, and the heat of it was electric. It was longer than mine, a lot longer actually. I stroked him to the tip, and pressed my fist down into his balls on the downstroke, just the way I like it on myself. I didn’t know what to think, only that my skin felt on fire.

He leaned closer, and I turned, maybe by instinct. Before I could say a word, his mouth pushed into mine. There was no hesitation this time. Just pressure, warmth, tongues.

The kiss deepened, and somehow the couch disappeared. Time blurred.

Eventually, we found ourselves lying down, limbs entangled, our bodies brushing in places that made me nervous about what was going to happen, how this was going to escalate further. It wasn't planned, at least not by me. Just a series of quiet, curious decisions. All I knew was that I didn't want to speak, didn't want to bring us back to reality from whatever plane of the universe we had just entered. We were humping each other roughly, groping each other's muscles and asses.

We sat up, facing each other, and pressed our balls together. We were sweating, and I could literally smell his dick. We started jerking each other off, and he spit down onto both our dicks. He pushed my hand away and jerked us off together, like it was one mega-cock. It made me feel like I was having sex, and I started thrusting up into him, mashing our balls together in sync.

Then he slowly pushed me onto my back, and lined up his dick with my hole. My chest tightened as I felt the tip press against me, and I let out a shaky breath, unsure if I was ready for this. But Mason’s eyes were steady on mine, calm but intense, like he was waiting for me to stop him. When I didn’t, he pushed in slowly, inch by inch. It burned at first, a sharp, unfamiliar pressure that made me grit my teeth. I gripped his shoulders, my nails digging in, and he paused, giving me a moment to adjust.

He raised his eyebrows, as if to ask, you okay?

My mouth was open, trying to keep breathing. I nodded, even though my heart was pounding.

He did go slowly, at first. The initial discomfort gave way to a strange, heavy fullness as he began to move, his hips rolling into mine in a steady rhythm. I thought it was going numb, but the pressure, and the visual stimulation of being held down and humped by my hung friend, watching his large cock disappear under my balls, started to give me tingles. He continued to spit down onto his cock every minute or so, sensing that we needed lube that we didn't have. I closed my eyes, focusing on the sensation, on the way his breath caught every time he pushed deeper. It was overwhelming but not entirely unpleasant. The pressure started to shift, the sharp edges softening into something... nicer.

Then, without warning, he picked up the pace. My eyes shot open, and I stared up at him as he fucked me harder, his thrusts becoming more urgent, more desperate. My mind raced, torn between the shock of what we were doing and the strange, growing pleasure that was starting to take over. The numbness faded, replaced by heat that spread through me, tightening my stomach, making it hard to breathe.

Mason’s hands gripped my hips, holding me in place as he drove into me, his body tense, his jaw clenched. I could feel him getting closer, his rhythm faltering, his breath coming in ragged bursts. And then, he grunted like he was going to say something, but he didn't, and he buried himself deep, his hips jerking as he came inside me. I felt the warmth of it, the way he shuddered above me, his body going still for a moment before he collapsed onto my chest, his forehead pressed against mine.

We lay there, tangled together, his weight pressing me into the couch. Neither of us spoke. The room was quiet except for the sound of our breathing, heavy and uneven. My mind was still spinning, but I didn’t pull away. Not yet.

I started to jerk off, my fist rubbing against both of our abs. He pulled out of me, and I hated feeling empty, but he stepped forward and dangled his cock on my face. Instinctively, even though it was just in my ass, I leaned forward to clean his cum off of him. I hit the edge and splattered all over myself, holding his shaft in my mouth. I collapsed down onto the couch, looking up at him staring down at me.

He shook off his cock, and the last drops of cum and spit dripped down onto my face. I watched his ass as he walked away to the bathroom.

Anyway, that was the time I realized I was bi, and gained a fascination with my best friend's cock.