Ask him to whip it out

"I saw your dick in, what, seventh grade? Back then anybody with more than 5 inches was big. Doesn't mean you're bigger than me now."

Your heart is beating out of your chest. You just challenged Will. This is gonna go one of two ways: either he whips it out and dares you to get hard to prove him wrong, or he gets awkward and backs down.

"DUDE. That's bullshit and you KNOW it!"

Your heart pounds as you say the words that fill you with both excitement and dread: "Prove it."

Will's jaw drops in disbelief at your words, and for a moment of panic you're sure you've screwed the pooch, but then Will eyes you with a steely gaze, and you know you've got him hook, line, and sinker.

"Fine, you asked for it." With one swift motion he's completely nude, his rock hard dick lying against his stomach. Fuck, it's big alright. At least eight inches, maybe even closer to nine, and thick. "Your turn."

"Huh?"

"I said your turn. You told me to prove I was bigger and I'm gonna do that beyond a shadow of a doubt. Now get hard so I can prove to you once and for all that you're full of shit." You glance down, nervously, and Will smirks as he sees you already hard. "Looks like somebody was too excited to lose. Or are you gonna tell me you just 'randomly' got hard right then?" You blush deeply as he calls you out. "Well, now that I'm out of these clothes, I guess I better put them outside so we can sleep without smelling like shit." He moves toward the door, which is on your other side, but takes the opportunity to tease you mercilessly. Instead of crawling over you, he straddles your chest and leans over, unzipping the door and throwing his clothes out before closing it and looking down at you. His balls are dragging against your chest, and his eight inch cock is now sticking straight out, mere inches from your face. You have an urge to touch him, lick him, suck him, something. But even now, you're still afraid to make the first move. Will looks down at you and smirks, knowing every thought that travels through your head. He moves a hand upwards and pushes his head to the side, cracking his neck.

"Ah man I'm pretty sore from all the hiking today. I better stretch out so I don't cramp."

He arches his back away from you, thrusting his hips forward in the process. His dick is now rubbing all over your face, leaving some precum on your cheek. Suddenly, as he "stretches", you feel his hand caress your balls, and without meaning to you gasp. Your hot breath on his cock must feel good, as Will shudders visibly, before moving his hand upward to wrap around your shaft. You groan at the welcome sensation of a foreign hand gripping your member, and Will finally decides to take advantage of your open mouth. He slowly moves his throbbing penis into your mouth, all the while sensually jerking your dick. You eagerly accept the intrusion, and begin working your tongue around the head and providing just enough suction to keep everything tight. It isn't long before Will unexpectedly pulls out. You shoot him a quizzical look, but he answers it quickly by spinning around and taking your rock solid member into his mouth, leaving his own erection hanging in front of you. You return it to your mouth and resume blowing him as your hands massage and play with his ass cheeks. He moans appreciatively onto your cock, and the vibrations from the sound nearly push you over the edge. By some miracle, you manage to hold off, but you know that victory will be short-lived. Will is in a similar state, and within another minute he releases your dick and loudly proclaims his orgasm.

"Oh shit I'm about to cum. Oh fuck. Here it comes!"

His cock fires off several spurts of cum into your mouth. You've never swallowed it before, but don't get the opportunity to do anything otherwise thanks to the position you're in. Thankfully, it isn't that bad, and you make a mental note that you don't mind doing this again in the future. Will calms down after a moment of heavy breathing and swings his legs off of you. You move your hand down toward your own aching cock, eager to blow your load, but Will intercepts it and pins it to the ground before slowly dragging his tongue down your body toward your erection. By the time he arrives, the suspense itself has nearly done you in, and after a few quick strokes inside his mouth you hit your climax. Will takes the first two spurts in his mouth, before pulling off and taking the rest of your orgasm on his face. He looks sexy as fuck with your cum splattered across his mouth and cheek, and afterward he falls next to you, both of you breathless.

"Holy shit. Why did we ever stop doing that?" he asks you.

"Fucking beats me, man, but we're definitely doing that again another time."

"Fuck yeah!"

Will cleans himself up, and the two of you drift into a deep and satisfying sleep.