november 7th

It has already been a week since you left Matt all hot and bothered with that damned viagra pill in his system. He had to take a cold shower and curse both you and Chris as he shivered under the cold stream. After that though, he hasn’t really had any problem except in the mornings where he’d wake up with a boner.

He hasn’t touched his dick at all. He knows he probably won’t stop if he actually started touching himself and that would end up with him orgasming and he can’t lose 200 bucks over something like that—or maybe he’s just too stubborn and competitive.

It helps that you’ve been avoiding too much physical contact with him, sitting close but not close enough. Still, you can’t help but tease him sometimes, bending over in front of him on purpose or “accidentally” placing your hand on his upper thigh for support while reaching for something.

november 14th

14 days without orgasming has Matt feeling horny and annoyed. He gave in and touched himself on the 8th day but didn’t cum. Instead he edged his poor dick until it was red and raw, almost on the verge of tears as he felt himself pulse and throb.

He’s been watching you with intense eyes, not saying anything but everything about his stare screamed he was horny and you were what he desired. You avoided his gaze most of the time—but when you did make eye contact, you’d only smile knowingly and tease him silently. Like you knew exactly how much he was suffering.

Chris has been as grumpy and quiet as Matt, not wanting to lose the bet, too. He’s been avoiding being around women in general, afraid he’d get a boner from people he considers as friends because both him and Matt are at the point where they’d get hard from literally anything. Nick on the other hand? He’s been all smiles since he’s been getting himself off unlike his brothers.

november 21st

By the end of week three, Matt was so sure he’d lose. He hated how horny he was but he couldn’t help it. He needed to come; He needed to feel that euphoric sensation taking over his body even for a few seconds. Still, he was awfully determined to win this bet, even though he was so close to giving Chris 200 dollars just to relieve the frustration he’s been feeling from not cumming in the past 21 days.

He tried his best not to touch himself but failed every night when he was lying in bed alone. The silence too loud but not loud enough to drown out the dirty thoughts and scenarios playing through his head. So he touched himself, slowly at first, just palming his growing cock through his boxers until he was leaking into it.

But that’s all he did, leaving himself on edge as he tossed and turned, trying to fall asleep. It goes without saying that he hasn’t had good rest lately since he was too horny or frustrated most of the time. All that led to him being a little more snappy and sarcastic than usual. But you didn’t mind, you liked seeing him so desperate.

november 28th

It was almost the end of the month and Matt had somehow grown numb. He didn’t really feel any arousal anymore, thankfully. Chris on the other hand had already given him 200 bucks in cash, saying something about not wanting to play “dirty” and keeping to his words. Which only earned him a disgusted look from Nick and a smug grin from Matt.

Matt knew he didn’t have to edge himself anymore but something about the bet, although it ended, was more thrilling than before. There were only two days until December 1st and Matt wanted to edge himself until then, not let himself cum until the month was fully over.

He’d touch himself at night and even in the morning during the remaining two days, enjoying every bit of the orgasm denial he was giving himself like a sick pervert. He’d also casually sport a hard-on when he was in his room and you were around, knowing damn well you could see the outline of his hard cock through whatever pants he wore that day.

december 1st

You’re both back in the same position you were in a month ago—curled up on Matt’s bed with a movie playing on his laptop. This time though, you’re purposely close to him, head on his shoulder, arm slung around his middle. If a stranger saw this scene they’d probably think you’re dating.

Your shift slightly, getting even more comfortable snuggled up beside him. And after you settle, you let your hand wander south, toying with the strings of his pajama pants, knuckles deliberately brushing against his dick through the thin fabric.

"Hey..." Matt’s voice comes out slightly breathless when you continue to tease the strings of his pants. His hips almost buck into your hand, but he holds himself back somehow. You can see his jaw clenching through your peripheral vision, the sight making you smirk triumphantly.

"C’mon..." He practically whines out as his hand darts out to hold your wrist in place before pushing it away gently. "I can’t focus on the movie." He complains. But how can you stop teasing him when his pants are already tented so deliciously?

"It’s already December, you know?" You sit up straighter, turning your body towards him, lips curling up with a small, teasing grin. "I know you’re pent up... I can take care of you if you just let me."

Matt’s heart begins to race, his pulse going straight to his cock, making it throb with each heartbeat. He’s never seen you so straightforward, so blunt—so wanting.

"Chris and Nick are home..." He tries to resist the temptation.

It only makes your grin widen. "And? We can be quiet."

"The bed will creak-" "They won’t care."

Matt stares at you for a moment, searching your eyes, his rational side fighting with the desire that had built up over the past month. His dick is so hard that it feels like it’ll explode if he doesn’t give it some relief, leaking precum into his boxers.

"Fuck," he curses, running a hand down his face, unable to believe he’s about to go through with this. He breathes out shakily, pushing his laptop off his lap and placing it on his nightstand instead. "So... We’re really doing this. Like, actually having sex?"

"Yeah." You start peeling off your shirt without another word, pulling it overhead, revealing your pale blue lace bra. You can hear Matt’s breath hitching audibly when he sees the skimpy lace on you, barely doing anything to cover your erect nipples.

"Fuck- Wait, wait-" Matt sputters, flustered at your sudden half-naked state. He can feel his dick jerk in his pants, as if it’s excited to see you stripping.

God, it’s as if he can only think with his dick right now.

You ignore his flustered words and shimmy out of your pajama pants under the covers and his eyes almost bulge out of their sockets when he sees the matching lace panties hugging your curves just right.

"Oh, fuck..." He mumbles breathlessly when you climb onto his lap, warm thighs on each side of his hips. His hands immediately settle themselves on your hips, fingers digging into your skin. "You’re gonna kill me." He groans softly, almost pained, clothed cock throbbing desperately under you.

Your hips begin rolling in a slow, almost sensual, rhythm, hands on his shoulders for balance. His head lolls back against the window shade, resulting in the metal bar at the bottom of it to thud softly against the thick glass.

"Fuuck..." Matt moans softly, the stimulation of your clothed core rubbing against his length through his clothes—although slowly—feels more intense than before due to how sensitive he’s become after a month of self-edging.

It’s a miracle he hasn’t come instantly because he’s really, really, close. And you know he is. So you tease him more. Your hands reach around your back to unclasp your bra, letting the soft lace fall away from your bare breasts before tossing the skimpy fabric onto his nightstand—it landing on his laptop.

Matt almost loses it at the sight of your perfect tits, his mouth watering. He looks completely undone already; his face is contorted in pleasure, lips parted, eyes heavy-lidded, and brows set in a pleasured furrow. His hips give small involuntary jerks up when you roll your hips just right, his breath getting caught between moans.

His eyes dart down to where you’re teasing him relentlessly before snapping back up to your face and then down to your boobs, seemingly unable to keep his eyes off the perfect pair of soft looking mounds.

Before he can hesitate further, his head is already dipping, lips immediately latching onto one hardened nipple, sucking gently and moaning softly around it. The vibrations from his moans against your hard peak make your back arch, feeling more aroused than you ever have before.

You keep grinding your pussy against his leaking cock through your clothes while one of your hands leaves his shoulder to grasp onto back of his hair instead, fingers curling gently around his soft brown locks as you keep his face buried in your tits.

He’s lavishing attention on your tits, his hands working in tandem with his mouth, occasionally looking up at you through his lashes as his tongue and teeth work on your nipples. You were never one to enjoy having your tits sucked like this but Matt doing it—so enthusiastically at that—is making your head cloud with pleasure.

After a while, Matt pulls back with a wet pop, his lips and your nipples shiny with his saliva. His eyes close briefly at the familiar feeling of tight coils in his tummy, curling tighter with each drag of your pussy against his sensitive cock. And even through clothes, it’s intense—or Matt’s just extra sensitive right now.

"Shit- I’m gonna cum... Slow down." Matt groans, his brows furrowing further, jaw dropping slightly when you ignore him and move faster. "Oh—Oh my God--" He gasps out, hands flying to your hips to slow you down.

Your lips quirk up despite your pleasure at seeing him so sensitive and needy. "You’re gonna cum? This fast?" Even though you’re taunting him, you slow down per his plea.

"I can’t help it. I need you- need to be inside you." He throws his pride aside and admits desperately. "C’mon, pretty..." He begins peppering kisses up your neck, nipping at your skin when he reaches your jaw.

You moan softly—but then a soft huff of air escapes you, almost sounding like a breathy chuckle. "You’re soo needy, Matt."

That was his last straw and before you know it you’re already under him, legs getting spread open by his hands so he can settle between them. "You think I’m being needy? I’ll show you fucking needy." His voice is low when he talks, hands immediately going south, tugging down your panties before you can even process his words.

You giggle, not realizing you’re about to get fucked completely stupid, thinking he’s not being serious. But Matt is dead serious about making you dumb with his dick. He waited so long for this—to feel your tight pussy wrapped around him—so he cannot take any more of your teasing.

He pulls his tank top off quickly, the abrupt movement making his chain smack against his skin, glinting in the dim light of his night lamp. His hair is a mess atop his head, from your fingers and his own.

"Spread your legs wider." He commands gruffly, thumbs hooking into the waistband of his pj pants, pulling it down quickly to reveal his long, fat cock. It’s so hard that it looks like it’d burst if it doesn’t get some release any time soon.

He usually doesn’t go commando, but with how much he’s been touching himself without actually orgasming, he saw no point in wearing boxers. His dick’s hard all the time anyway, it’d only hurt more if he wore something as constricting as underwear.

Your eyes widen slightly, lips parting, taking in his size in pure unadulterated awe and desire. He’s a lot bigger than you’d expected. You could tell he was big when you were grinding on his lap, but without any clothes it’s apparent he’s huge.

Fuck... That thing is going in you???

You spread your legs wider with your arms hooking under your knees, watching him move closer, cock bobbing obscenely between his legs. He doesn’t even bother taking off his pants, gripping his cock and giving it a few rough tugs as he looks down at your pussy lips glistening with arousal.

When he runs the head of his dick through the wet mess your core had become, you barely hold back a moan, your back arching ever so slightly. Something about a dick so big entering you is making you hornier than before—especially knowing it’s your best friend who’s about to fuck you.

Matt wants to tease you and make you beg, but he knows he won’t last himself if he teases you—he’d end up being the one begging. And therefore, he decides to save that for later. He knows you’ll let him fuck you again after you get a taste of his dick.

Your sharp gasp when he slowly begins to push inside your tight, slippery walls goes straight to his balls. He watches your expression change the deeper he sinks into your heat, and the more your knuckles grow white from how tightly you’re holding your own legs apart for him.

He stops when he’s about halfway in due to how tight your pussy is hugging his thick meat, and he lets out a breathy chuckle at your whimper, finding it endearing how you’re trying your best to adjust to his size. "Too big?"

You nod, trying to breathe through the stretch, pussy fluttering around him as if it’s trying to suck more of him in even though it’s barely fitting around him. The sensation makes Matt’s eyes roll back briefly, a low groan getting caught in his throat. "Fuuck... She’s squeezing me s’tight, sweetheart."

He pulls back slowly, letting his heavy length drag across your walls, until only the tip remains, before pushing back inside equally as slowly. And he repeats it, over and over again, going deeper with each slow thrust until he’s completely sheathed inside your warmth.

"Feels so full... Matt, you’re in too deep..." You whine, hands trying to push his hips away to let your cervix breathe. His tip is literally pressing against it, kissing the opening to your womb like he’s claiming it as his own.

"Just breathe, baby." He coos but pulls back slightly per your request, taking away from the pressure. But before you can breathe out in relief, he pushes back in again sharply, bursting out laughing like it’s the funniest thing when you gasp sharply in return.

You mock glare at him, watching his eyes crinkle at the corners in amusement, gums showing slightly as he laughs like he hasn’t laughed in years, wheezing softly. You can’t help the laughter bubbling in your chest. After all, Matt’s laugh is contagious. "You’re such an ass..."

The mood is broken momentarily as you two laugh at the ridiculousness of the situation. But neither of you would have it any other way. Plus, it helps you take your mind off the fullness and pressure of him stretching you out.

"Shit... What are we even doing?" Matt chuckles, his laughter dying down slightly as he gazes down at you with something so intimate it makes your heart beat faster, your own laugh subsiding into a small smile.

The way his eyes sparkle with leftover mirth and love—something more deeper than just affection for a close friend—fucks with your head and heart. You can’t possibly fall for him, can you? This is supposed to be sex. But why did you two even have sex in the first place? Because you promised him? Because of that no nut November bet and the Viagra pill?

Before you can keep overthinking the meaning behind his actions—and yours—Matt begins moving, his cock throbbing as he feels you clench around him at the suddenness of his movements. His jaw ticks as he bites back a moan, inhaling and exhaling shakily as he murmurs. "Look at me... Only think about my dick inside this pretty little pussy, ’kay?"

His forearms cage your head in, face inches from yours, as his hips slap against yours with soft, wet smacks. His icy blue orbs watch your expressions intently, as if he’s burning them into his mind while simultaneously trying to find your favorite angle.

"Oh, fuck--" Your eyes roll back, words tumbling out as a breathy moan, as the tip of his dick hits your g-spot just right.

Matt grins slowly, dick throbbing. He thinks your reaction is the sexiest thing he’s ever seen. No porn or woman has left him this horny. "Right there? That your spot, baby?" His words are laced with a subtle taunt that he doesn’t even seem to notice, it flowing out naturally.

And with each thrust after that one, he makes sure to target that spongy spot inside you, watching in pleasure as your mouth opens in a silent scream, hands desperately clutching onto his biceps like it’d ground you from the intense pleasure he’s giving you.

Matt loves the way you’re falling apart on his dick, and how good he seems to be making you feel. Your pussy squeezing him like it wants him inside you forever is getting him closer to the edge faster than he wants. He doesn’t want to end this so quickly—He wants to stay connected to you.

One of his arms caging you in reaches down toy with your clit, determined to make you cum before he does—because he’s really damn close to nutting inside you. Jaw muscles ticking, he clenches his teeth, hard, trying to hold back his orgasm.

But his jaw goes slack when he feels your pussy flutter around him desperately, his eyes rolling back briefly at the feeling of you orgasming so hard around his fat cock. Your own eyes are rolled back, tears brimming against your waterline as he pounds you through your orgasm, barely letting you get down from your high.

"M-matt--" You choke on a moan when his hips picks up pace, fucking you in shallow but deep thrusts. Your vision is barely focused, blurring with tears, stars exploding behind your eyes. And the sight of you so fucked out with tears beginning to stream down your face makes Matt’s balls draw up tight against his body.

"Fuck- I’m gonna cum-" Matt warns, gasping, quickly trying to pull out. But your legs wrap around him tightly and suddenly, making him groan and grunt as he tries to hold back his orgasm. "Sweetheart—fuck—I’m not kidding- I’m about to fucking come inside you!"

But you don’t let go of him, even as his hips twitch and jerk against yours, arm veins bulging, knuckles white as he clutches onto the sheets on either side of your head tightly. "Come inside me, please...? Wan’ you to cum inside-" You hiccup, brows knitted together, teary eyed. "Wanna have your babies- Please?"

The sound of your voice, so whiny and desperate and needy and literally begging for his semen, makes his dick twitch inside you, his shaft swelling larger. He tries—he really does—to hold back his impending orgasm, but it’s inevitable as he loses himself in your tight, wet warmth, slowly giving in to your tempting pleas.

"God... You want my cum? Want me to knock you up?" He begins thrusting hard and fast, loving how good you look with your legs wrapped tightly around his waist and taking his big dick like a good fucking girl. "I’ll fucking give it to you. You’re gonna be such a pretty mama, y’know that? You’d look so beautiful with your tummy swollen with my fucking kid."

His dirty talk, how sensitive you are after your orgasm, and the feeling of his dick hitting all your sweet spots, is pushing you closer to another orgasm. And Matt notices, chuckling breathlessly as he keeps fucking you, about to climax himself.

Your second orgasm crashes over you in strong, unrelenting waves, making your back arch and nails dig into his biceps, legs tightening around his waist. You coming around him the second time is what pushes Matt over the edge, the bands in his stomach snapping so hard it makes his vision spot.

"I’m filling you up... Fuuuck..." He groans, his hips grinding against yours, hot cum filling you to the brim. "Keep squeezing me like that and you’re not leaving my bed until morning."

Your heavy-lidded eyes lock with his dark ones, your heart pounding in your chest and pussy throbbing around him. The way he’s staring down at you, with such a loving gaze, is making the line between friends and something more blur.

His hand comes up to gently cup your face, thumb brushing over your cheekbone tenderly. Neither of you say anything for a while, just staring into each other’s eyes, heartbeats matching in rhythm. And when he finally leans down to kiss you, it’s much softer—more intimate—than before. Like he’s pouring out his feelings before he can even tell you through words.

And just as you’re making out slowly, his softening dick still buried inside your warmth and cum oozing out around his shaft, Matt’s phone vibrates on his nightstand. Both of you jump slightly in surprise, the intimate bubble bursting, and he groans softly in annoyance against your mouth.

With a soft grunt, Matt pulls back just enough to take his phone, not bothering to pull out even as his brother’s name flashes across his phone screen.

Nick’s voice immediately goes through the moment Matt takes the call, sounding exasperated. "Are you serious? You couldn’t be quieter? Both me and Chris could hear you guys."

Your face burn in embarrassment as you listen to Nick talk, petrified at the fact that his brothers heard you two fucking. But Matt seems to find it amusing, even though he probably is embarrassed as well—judging by the way his cheeks seem to flush a deeper shade of pink than it already was from exertion.

When he ends the call, you immediately groan softly, hands coming up to cover your face. "I can’t believe this." Your words are slightly muffled behind your hands, and you feel his hands gently prying them away from your face.

"Next time, I’ll bend you over your bed." He says casually, like he isn’t making plans to fuck you, in your bedroom to be specific.

"Next time? My bed?" Your lips quirk up at the corners with a subtle smirk, amused, your earlier embarrassment temporarily forgotten. "And who says I’ll let you fuck me again? Let alone let you inside my house and my room knowing you’re thinking about bending me over like some pervert?"

Matt laughs at your words, his eyes crinkling in amusement. "Oh, I know you’ll let me fuck you again." He pulls out slowly, both of you hissing softly at the sensitivity and the sudden exposure to cool air, before he rolls onto his back beside you. "And you live alone, so no one would complain if I fuck your brains out."

"I have neighbors-"

"Fuck your neighbors. Matter of fact, why don’t we move in together in a soundproof apartment-"

"Matt, be serious."

Matt laughs again, pulling you into his side so you’d be snuggled against him, a cheeky grin on his face as he looks down at you. "I’m just messing with you." Is what he says, but he doesn’t sound like he is.

But it’s not like you’re really complaining.

In fact, you might already be planning what kind of house you’d live in after marriage.

Well, you’d never tell him that though.

Not now, at least.

© 𝒄𝒉𝒓𝒊𝒔𝒔𝒔𝒊𝒓𝒆𝒏