All characters engaged in sexual activity are 18 or older.
Leo
I’m buzzing the second I wake up the next morning. By the time night rolls around, I’m straight-up stoked. Yeah, Will took the first challenge yesterday, but tonight? Tonight I’m getting my win back. I can feel it.
I’ve always been competitive. It’s been baked into me since I was a kid, but it got ugly once I started showing talent in sports. Coaches, parents, scouts—they all looked at me like I was the next big thing, and that pressure turned into this constant voice in my head whispering that I wasn’t good enough, that I had to work twice as hard as everyone else just to keep up. So I did. And somehow it worked. Now I’m the star of the college football team, and the NFL feels closer every season.
A knock on the door yanks me out of my thoughts. I open it and there’s Will, standing in the hallway looking cute as fuck in a tight black t-shirt that clings to his lean soccer body and a pair of gray sweatpants that hug his thighs in all the right places.
What the fuck? Cute? He’s my best friend. I’m not gay. I shove the thought down hard and force a smile.
“Hey, come in.”
Will steps inside, glancing around. “Where’s Tony?”
I shrug. “Probably with that girl he picked up this morning. Dude’s on a streak.”
Will chuckles. “Good for Tony. He doesn’t get laid enough.”
I grin. “True.”
He turns to me, those dark curly strands falling over his forehead, and asks the question I’ve been waiting for. “So… what’s the next challenge?”
I let the smirk stretch slow across my face. “Oh, you’re gonna like this one.”
I pause just long enough to watch his eyebrows lift, then drop the bomb.
“We’re doing a cum distance contest.”
Will stares at me, stunned. “A… cum distance contest?”
“Yup.” I’m proud of myself for throwing him this off-balance already. “Here’s how it works. We jack each other off for three minutes. After the timer goes off, we take over and finish ourselves. We alternate so the other guy gets our full attention. Whoever shoots farther wins. Loser has to clean up.”
Will’s voice drops to almost a whisper. “Clean up?”
I smile, all innocent. “Yup. Clean up.” I don’t elaborate. Let him stew on that.
I clap my hands once. “Alright, let’s get started.”
I don’t waste time. I peel off my tank top, then shove my shorts and boxer briefs down in one smooth motion, kicking them aside. I’m completely naked, already half-hard just from the anticipation.
Will hesitates for a second, then starts stripping too. He’s slower about it, clearly nervous. Good. If he’s psyching himself out, that works in my favor.
When he’s finally naked, I let myself look. Really look. He’s tight and lean—defined abs, slim waist, nice pecs that flex when he breathes. His cock is already thickening, hanging heavy between his legs. Not gonna lie, the view does something to me.
I walk over to the kitchen area I cleaned up earlier and point at the strips of painter’s tape I laid down on the floor. “We kneel here. I’ve got the measuring tape ready so we get an exact distance. No bullshit.”
I toss two pillows down for our knees and grab the bottle of lube I left on the counter. “Since this is my challenge, I go first.”
I drop onto the pillow and hand Will the lube. Then I set a three-minute timer on my phone and place it where we can both see it.
Will kneels in front of me, looking a little shaky. He pours lube into his palm, then reaches out. The second his slick hand wraps around my cock, a low moan rumbles out of my chest.
Fuck. He knows what he’s doing.
He strokes me from base to tip with a perfect twist at the head, then slides back down. His thumb swipes over my slit on every upstroke, spreading the precum that’s already leaking out of me. Another moan slips free, and I hear a tiny whimper come from Will too.
I glance down. His own cock is rock hard now, flushed dark and drooling a steady line of precum onto the floor even though no one’s touched it yet.
“Play with my balls,” I breathe.
Will doesn’t hesitate. His free hand cups my sack, rolling my balls gently, tugging just enough to make my toes curl while his other hand keeps working my shaft in long, slick strokes.
The timer goes off way too soon.
Will lets go immediately. I take over without missing a beat, pouring more lube straight onto my cock. The memory of his hand is still burning through me as I stroke hard and fast. It doesn’t take long. My orgasm hits hard—one of the best I’ve had in months. Thick ropes of cum shoot out of me, splattering across the floor in long, powerful spurts.
I milk myself through every pulse, then grab the measuring tape.
“Twenty-seven inches,” I announce, unable to hide the pride in my voice.
Will looks stunned. I’m not sure if it’s from jacking me off or from how far I shot. Either way, I grin at him. “Your turn.”
I reset the timer, pour a generous amount of lube directly onto his cock, and watch him suck in a sharp breath as the cool liquid hits his hot skin. Then I wrap my hand around him.
It feels different than I expected, someone else’s cock in my fist. Hot. Hard. Velvet-smooth over steel. This is the first time I’ve ever jerked another guy off, and honestly… I don’t mind it at all. My own dick is already twitching back to life, which usually takes forever after I cum when I’m with a girl.
I stroke him the way I stroke myself—firm, steady, twisting at the head. I play with his balls too, massaging and tugging while my thumb keeps teasing his leaking slit and then moving down to play with the frenulum. Will’s breathing gets ragged fast.
The timer goes off again.
I let go and nudge him. “Finish it.”
Will looks dazed, like he’s floating. He pours more lube on himself with shaky hands and starts stroking. He doesn’t last long. Less than a minute later his hips jerk and he’s cumming hard, shooting thick ropes onto the floor.
I grab the measuring tape again and check both distances.
I win. By almost four inches.
I pump my arms in the air. “I win!” Then I do a little victory dance, shaking my ass in his face just to fuck with him.
Will gives me a nervous look. “Congrats… I guess I have to clean up now.”
I nod, still grinning. “Yes you do.”
What happens next nearly shorts out my brain.
Will drops back down to his knees, leans forward, and drags his tongue straight through the biggest puddle of my cum. He licks it up slowly, deliberately, then moves to his own load and cleans that too. Every drop.
I watch, frozen. I figured he’d ask for paper towels. I never actually thought he’d… fucking lick it.
When the floor is spotless, Will crawls forward on his knees until he’s right in front of me. He looks up, takes my half-hard, messy cock in both hands, and without a word wraps his lips around the head.
I stammer, “What are you—?”
He pulls off just long enough to smirk. “I’m cleaning up.”
Then he licks me clean—long, slow strokes of his tongue over my shaft, around the head, sucking off every trace of lube and leftover cum. When he’s done, he pulls off with a wet pop, leaving my cock rock-hard, glistening, and throbbing in the air.
Will wipes his mouth with the back of his hand, stands up like nothing insane just happened, and offers me his hand to shake.
“Congrats again.”
I shake it on autopilot, still speechless.
He starts pulling his clothes back on, calm as ever. “I look forward to the next challenge tomorrow. Now that I know what kind of games you want to play.”
With that, he leaves.
I’m left standing in the middle of my dorm room, completely naked, cock still hard as fuck and pointing at the ceiling.
I laugh, low and a little stunned.
I may have won this challenge… but clearly the competition is nowhere near over.
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