I let my Gay Best friend stretch my hole

Straight college guy lets his gay best friend stretch his tight hole for the first time. What starts as drunk “no homo” teasing turns into spit-slick fingers, slow deep strokes, and a thick load left leaking out of him. He never expected to moan like that or come harder than he ever has with his girlfriend.

  • Score 8.6 (1 votes)
  • New Story
  • 2761 Words
  • 12 Min Read

All characters are 18+ and fully consenting


Some friendships just kind of settle deeper than you ever expect them to.

I met Mateo freshman year in the dorms. Same floor, same shitty shared bathroom that always smelled like cheap body spray. We got close mostly because we were both up late all the time, gaming until two or three in the morning, and because neither of us could cook anything more complicated than ramen without setting off the smoke alarm.

By sophomore year, we were roommates.

Junior year, we moved into a cheap two-bedroom off campus with a third guy who was barely ever there anyway. Now we're both in our last semester, and somehow we're still stuck living together half the time because the lease doesn't end until August and neither of us has figured out what the hell we're doing for actual adult housing.

Mateo's been out since high school. He never made some huge thing out of it. He just lived his life. I always told myself it didn't change anything between us. We still watched the same games, talked the same shit about girls I was trying to get with, and passed out on the same couch after we'd had too many beers.

Sometimes he'd bring guys over. I'd put my headphones on and give him his privacy. He never pushed anything on me, and I never really asked questions that felt too personal.

It worked.

Last weekend, his parents were out of town, and he invited me over to their place for a "proper weekend instead of this dump."

Their house has a pool, a finished basement with a huge TV, and a fridge that actually has real food in it. Not just beer, takeout, and whatever the hell had been sitting in our fridge for three weeks.

I said yes without even thinking about it.

Nancy and I had been fighting again. Same old shit. Me not planning enough, me not being romantic enough, all that. I needed some space.

I told her I was crashing at Mateo's to help him clean the place up before his parents got back.

That was only half true.

We started with pizza and a six-pack each, just sitting on the basement couch and scrolling through absolutely nothing. The game was on mute because neither of us was really watching it anyway.

The conversation just kind of went where it always goes when it's only us and the alcohol starts kicking in.

He asked how things were with Nancy.

For once, I actually told him the truth.

Sex had gotten pretty mechanical. She finished maybe one time out of five, and honestly, I was starting to feel like I was performing instead of actually wanting it.

He listened like he always did. Didn't judge me or try to give me some big speech. Just nodded.

"You ever just want someone to take over for a night?" he asked, cracking open another beer. "Like, not have to think about the next move?"

I laughed.

"Yeah, but that's not really how it works with girls. You still gotta put in the effort or they check out."

He shrugged.

"Not always. Sometimes the other person just knows what they're doing and you get to shut your brain off."

I didn't answer right away.

For some reason, that stuck with me.

We kept drinking. The conversation moved on to random college stories, stupid shit we'd done, people we'd known, all of that. Somehow, we ended up talking about the fact that he'd never actually seen me fully naked, even after all these years of living together.

I called him a creep.

He called me a prude.

And somehow that turned into the kind of dumb dare that only happens when you're already half drunk and the house is empty.

"Fine," I said. "I'll strip if you do. Equal playing field."

We both stood up like idiots and started taking our shirts off..

His chest was smoother than mine. Less hair. He'd also gotten a lot more serious about the gym over the last year.

I looked him up and down and snorted. “Damn, bro. When the hell did you start taking the gym seriously?”

Mateo pulled his shirt off and tossed it at me. “When the hell did you start taking being a loser seriously?”

“Fuck you.”

“You first.”

I laughed and yanked my own shirt off. “Dude, you’ve gotten annoying as shit since you started lifting.”

“Jealous?”

“Of what? Your stupid little biceps?”

“They’re bigger than yours.”

Okay, Arnold... Calm down.”

He laughed. “You still look like you get tired carrying groceries upstairs.”

“That's because I make other people carry them.”

“Yeah, I know. I've lived with you for three years.”

“Well at least… I don’t spend twenty minutes oiling up in the mirror before I leave the house.”

“Please... You wish you had something worth oiling.”

We both laughed at that, the dumb kind of laugh that only comes out when you’re already a few beers deep and the room feels a little looser. Pants came next. I kicked mine off without thinking too hard about it. He did the same. Then we just stood there in our underwear staring at each other like a couple of idiots who’d talked themselves into something and didn’t know how to stop.

“Alright, prude,” he said. “You first.”

“Hell no. Equal playing field, remember? We go together.”

He rolled his eyes but hooked his thumbs in the waistband of his boxers. I did the same. On three we both shoved them down and stepped out.

There was a second of pure silence.

His cock was thicker than I expected, already half hard and resting heavy against his thigh. Mine was longer, thinner, and very obviously interested in whatever the hell was happening.

Mateo let out a low whistle.

Jesus Christ! You’ve been hiding that thing this whole time?”

I felt my face get hot.

“Shut the fuck up, man.”

“I’m just saying. Nancy’s lucky. Or maybe not, if you’re only getting her off one out of five.”

Wow… Real supportive.

He grinned and took a step closer. Not touching yet, just close enough that I could feel the heat coming off him.

“You ever think about it? Like, actually think about it?”

“About what?

“About shutting your brain off for once. Letting someone else run the show.”

I should’ve laughed it off. Should’ve grabbed my clothes and made some joke about him being a horny bastard and left it there. Instead I heard myself say,

“Maybe.”

"Want to see what it's like…?" he asked. "No strings, no labels. Just getting off with someone who already knows you?"

My mouth went dry, I whispered… “Maybe..

His hand wrapped around my cock like it was the most natural thing in the world. First stroke was slow, testing. My hips jerked forward without permission. His hand was rougher than any girl’s.  He watched my face the whole time.

“Feel good?”

“Yeah.”

He kept stroking, thumb sliding over the head every few passes, spreading the precum that was already leaking. I reached for him without thinking and mirrored the motion. His cock felt solid, heavy, the skin shifting under my palm. He let out this low sound that went straight to my gut.

We ended up back on the couch, still facing each other, hands working in the same rhythm. He leaned in and kissed me, not so soft, and it wasn’t testing… It was full blown on tongue and everything. I froze for half a second and then kissed back harder than I meant to. His free hand grabbed the back of my neck and held me there. The kiss got messy fast… teeth, spit, both of us breathing hard through our noses.

When he pulled back he was already moving down. He dropped to his knees between my legs and took me into his mouth without warning. His warm mouth and the pressure, the flat of his tongue pressing along the underside while he sucked. I grabbed the edge of the couch cushion and stared at the ceiling because looking down at him doing that felt like it would short-circuit something in my head. He didn’t go slow. He took me deep, gagged once, adjusted so fast and kept going like he’d been waiting for permission.

I lasted maybe two minutes before I had to push him off or I was going to finish right there. He wiped his mouth with the back of his hand and grinned up at me.

“Your turn if you want it.”

I did. I didn’t even pretend otherwise. I got on my knees and wrapped my mouth around him. The taste was clean, a little salty at the tip. I took as much as I could, used my hand on the rest, tried to copy what he’d done. He threaded his fingers into my hair and guided without forcing. Every time I looked up he was watching me with this half-lidded expression that made my stomach flip.

We switched again. Then he pulled me up onto the couch and turned me around so I was on all fours.

“Spit on my fingers,” Mateo said, voice low right behind me.

I turned my head just enough to look at him over my shoulder. He held his hand out, two fingers already close to my mouth. Something about the way he asked it… casual, like it was nothing, like he’d done this a hundred times… made my cock twitch hard against my stomach and a thick bead of precum leak out and string down onto the cushion. I spit.

He didn’t wipe it off or anything. Just rubbed his fingers together once and then pressed the tip of the first one against my hole.

“Breathe,” he muttered.

I did. He pushed slow. The burn hit right away, tight and sharp, but at the same time his other hand slid down the front of my hip and started rubbing along the V-line, slow and steady, like he was trying to distract my body from the stretch. His mouth was right at the back of my neck. Not kissing hard, just soft little presses of his lips, warm breath, the scrape of stubble as he nuzzled in closer.

I closed my eyes.

Everything narrowed down to that. The slow push of his finger, the way he kept rubbing that sensitive line on my hip, the heat of his mouth against my nape. I stopped tracking what he was doing. My head dropped forward and I just floated in it. The burn eased into this deep, open feeling, like my hole was getting wider without me even trying. I felt the stretch increase and somewhere in the back of my mind I knew he’d slipped a second finger in and crooked them.

That was when my cock jumped hard and a sound came out of my throat that I’d never made before…low, broken, almost like a moan I couldn’t hold back.

Mmgggaaahhhh….”

“There it is,” he said, almost quiet. “That’s the one.”

He kept working me open until I was pushing back onto his hand. Then he pulled his fingers out, lined himself up, and pressed the head of his cock against me. The push in was slow, steady, no sudden force. I felt every inch. When he was fully inside he stayed still, both hands on my hips, letting me adjust.

“You good?”

“Yeah. Move.”

He did. Short strokes at first, then longer ones once the burn faded into something deeper. The angle hit that same spot over and over. My cock was leaking onto the couch cushion. I reached under myself and stroked in time with his thrusts. The wet sound of him fucking me filled the basement. His breathing got heavier. He leaned over my back, chest against my shoulders, and bit the side of my neck hard enough to leave a mark.

“Fuck, you feel good,” he muttered against my skin. 

I didn’t answer. I just pushed back harder, matching him. The orgasm built differently than any I’d had with a girl…lower, thicker, spreading through my whole lower body instead of just concentrating in my cock. When it hit I came hard, shooting across the cushion and my own hand, clenching around him so tight he cursed and drove in deeper.

He followed a few seconds later, hips stuttering, cock pulsing inside me as he came. He stayed buried for a long moment, forehead pressed between my shoulder blades, both of us breathing like we’d just finished a sprint.

When he finally pulled out I felt the warm slide of his cum following. I stayed on my hands and knees for a second longer than necessary, then collapsed onto my side. He dropped down next to me, one arm thrown over his eyes.

Neither of us spoke for a while. The TV was still on mute, some commercial cycling through. My body felt loose and sore in places I didn’t know could feel sore. My mind was quieter than it had been in months.

Eventually he turned his head and looked at me.

“You okay?”

I nodded.

“Yeah. You?”

“Yeah.”

He glanced over at me again.

“So… how’re you feeling?”

 “Honestly?”

“Yeah.”

“Pretty damn good.”

He laughed quietly. “Yeah?”

“Yeah. I don't know. My head's just… quiet.”

“You ever get that feeling,” I said, “where you don't even wanna do anything? Just sit there and not think about shit?”

“All the time.”

I looked over at him. “Yeah. That's kinda what this feels like.”

He gave me a little smile. “Then don't do anything.”

Wasn't planning on it….”

I swallowed slowly and finally said what was sitting in my chest.

It’s weird…Mateo.. I feel… quiet. Like my head finally shut the fuck up for once. With Nancy it’s always this pressure, you know? Gotta make her finish, gotta last, gotta do it right or she’s gonna get that look. Here I didn’t have to do shit. You just… took over. And somehow that felt better than anything I’ve done in months.”

Mateo was quiet for a few seconds. Then he reached over and rested his hand on my lower back, not sexual, just there.

“That’s what I meant earlier,” he said. “About shutting your brain off. You don’t always have to be the one running the show.”

I turned my head and looked at him.

“Does it feel different for you? Doing it with a guy who’s never… you know.”

He shrugged one shoulder, but his eyes stayed honest.

“A little. I kept waiting for you to freeze up or tell me to stop. When you didn’t… yeah. It hit different.”

We both went quiet again. Mateo’s thumb moved in a slow circle on my back without him seeming to notice he was doing it.

We cleaned up with paper towels from the bar fridge. Neither of us put clothes back on right away. We just sat there naked on the couch that now had a wet spot we were both pretending not to notice. He grabbed two more beers and handed me one. The silence felt different this time… not awkward, just full.

I thought about Nancy, about the fights, about how I’d been going through the motions for months. Then I looked over at Mateo, his face lit up by the blue glow of the TV, and something in me settled that I hadn't expected. 

“So…” I said after a long pull of beer.

“So?”

“So what now? We just… go back to normal tomorrow?...Umm…That happen again or was it a one-time thing?”

He didn’t smile exactly, but the corner of his mouth twitched.

Up to you, Mate... We can try… Or we can not pretend this didn’t happen. Either way I’m still your friend. That part doesn’t change.”

I nodded once. My throat felt tight for some reason.

“Okay.”

He gave my back a light pat and then pulled his hand away.

“You want another beer or you just wanna lie here for a bit?”

I thought about it.

“Lie here.”

“Alright.”

I just leaned back, let my knee rest against his, and watched the muted game. The weekend was still young. His parents weren’t due back until Monday. And for the first time in a long time I wasn’t already planning the next excuse or the next fight or the next half-hearted round of sex that left both people unsatisfied...

I took another drink and let the quiet sit between us. For once, I wasn't thinking about what came next 

~(^_^)~

-Haha💦🍑


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