Archive of Our Own

The most mortifying day of Will’s life was when his best friend walked in on him getting spanked. Butt-naked spanked. 

He doesn’t even remember the name of the guy who spanked him, honestly. He remembers what he looked like, though. Tall, with dark brown eyes that bored into your soul, and the second most gorgeous head full of dark curls he’s ever seen. 

Will’s got a type, that’s for sure. The problem is it’s hard to find a guy that fits the exact specifications that he’s looking for. The physical aspects of what he likes is actually easy to find, and he’s had plenty of one night stands with guys like that. When it comes to personality and interests, he hasn’t aligned with anyone quite like that yet. Will would love to have a nerdy boyfriend who actually cared to hear about how his latest art projects are going, or exactly how he’d like his coffee in the morning, or what his favorite eateries were in the city. 

He’s only properly dated one guy, Caleb. They only dated for about six months in his freshman year of college, but Will really enjoyed his time with him. By the end of the school year, Caleb said he had an urgent family emergency to tend back to in his hometown somewhere in Pennsylvania. The breakup happened over the phone a week later. 

Since then, Will’s been searching and searching for a stable relationship with a nice, nerdy guy who, A, actually cared about him, and B, could fuck him into his mattress each and every night he was alive. 

Will’s sex drive was, surprisingly, high. He could go for multiple rounds even after so many guys were done after just one orgasm. He was kinky as fuck too, and some of his one night stands aligned with that, and some didn’t. 

The guy who spanked him to tears did. 

Will was on all fours on his mattress, his hair pulled taut by the man who was about to fuck him filthy. He had asked beforehand if he could be spanked a few times before he put it in. And he wanted to be spanked hard. 

The guy was more than willingly, acting like what Will asked of him was the best news he’d heard all day. So, he shoved him onto his hands and knees, gripped onto his hair, and started to raise his hand down forcefully against Will’s bare ass. 

The sound of the fat of his ass getting spanked was to die for. He loved it so much, it turned him on to the extreme. He squirmed and moaned after every slap, tears rolling down his flushed cheeks. 

Will counted after every spank too, wanting to really sear it in that he loved it. He loved being manhandled and treated in such a nasty way, it made him feel so seen and appreciated. He didn’t really want someone to be too gentle with him during sex, he wanted it rough. 

The seventh spank was when both the guy and Will heard his bedroom door creak open. 

Will’s heart practically sank to the floor when he heard it. He knew immediately that it was in fact his best friend and roommate, Mike. And knowing Mike, because Will knew him so fucking well, he most likely thought Will was getting hurt. He’s so protective over him, honestly way too protective for just a best friend, but that was one of Will’s favorite things about him. The way he cared, the way he swooped into action whenever he immediately suspected something was amiss. 

But, Mike was wrong. Will was not getting hurt; he was in no pain. He was crying tears of joy from how good he felt getting spanked and treated like a ragdoll. 

So, as Will reluctantly looked over to his now open bedroom door, he couldn’t help but feel immense shame flood through him. Mike wasn’t supposed to know he was into things like this, it was not his business. But, deep down behind all of that shame, Will felt an intense, panging arousal course throughout him. 

He never really got over his so-called crush on Mike. It’s definitely toned down over the years, to the point where he now only cries about once every two months from how he’s still hung up on his best friend. The pain has since settled into a dull ache; a dull ache that Will can ignore most of the time.

So, yeah, he still had the hots for Mike, and he couldn’t help but be turned on by his best friend seeing that vulnerable, and hopefully presented as so, sexy side of him. 

He locked eyes with Mike instantly. Will was, of course, wearing nothing and leaking all over his bedsheets. But, the damage was done. Mike had seen the guy whose name he’d forgotten slap his ass hard, leaving behind a throbbing red handprint on his left asscheek. 

Mike stood there with a face equally as red as the handprint. His fingers twitched nervously at his sides, almost as if he himself wanted to get his hands on Will. He stumbled backward, knocking into the doorframe like an idiot, and spoke probably a little too loudly, “Oh fuck— I am so sorry, Will. I thought—“ He stammered, his words clearly getting caught up in his throat, “I’ll… I’ll go.” 

He bolted out of Will’s bedroom as quick as lightning, the door slamming shut right behind him. Will was humiliated, fucking humiliated, as he buried his flustered face deep into his hands. His thoughts raced a mile a minute, still processing that, holy shit, Mike just watched him get spanked. Literally watched his face as he let out the most obscene, porn-like moan because of it. 

Nameless guy did not continue on with his spanks after that, instead he lifted his hands off of Will and proceeded to ask him, “That wasn’t your boyfriend, was it?”

Will kicked him out of his apartment after that. 

Thirty minutes later, when their shared space was now finally quiet, Will still felt the most embarrassed he had ever felt in his life. He stood just outside Mike’s closed bedroom door, watching as the light spilled into the hallway underneath the door crack. He didn’t mean for Mike to see any of that, and he feels deep within him that as Mike’s very best friend, he must apologize to him. 

As much as he would like to crawl into his bed and never emerge to see the light of day again, the light of day being his Mike, he had to do this.

He brought his closed fist up to Mike’s door, and he couldn’t help but wince and close his eyes as he finally let himself knock on the wood. 

There’s a moment of silence, and then Will hears feet shuffling around on carpet, and then to his current very worst fear, Mike himself opens the door and is met with the sight of an awkward-standing Will. 

Will audibly squeaked, suddenly standing up straighter when he noticed that Mike was looking down at him with those questioning, intense eyes of his. He clears his throat, actively avoiding Mike’s gaze and decides to stare at the framed dragon painting hung up on Mike’s wall that he had gifted him all those years ago in the back of a pizza van that reeked of marijuana. 

It doesn’t help at all.

“So, I… uh—“ Will stammers, closing his eyes and determinedly decides he just needs to spit it out. He opens his eyes again, looking up at Mike apologetically, almost hoping he could will him to forget about what he had witnessed, “You weren’t supposed to see that. Or… hear that, at all.”

Mike remains still and silent as he just looks down at Will trying to desperately apologize. The height difference between the two suddenly makes Will feel immensely smaller, and not in the way that he usually gets dizzy with desire from. 

He continues to ramble on, hoping that will help the situation in any way, “I-I thought you were going to be back much later. If I had just known you were going to be back sooner, fuck— I wouldn’t have invited that guy over at all. Look, I’m just—“ Will huffs, feeling frustrated like no matter how much he speaks, he can’t get his point across to the other man, “I’m sorry, Mike.” 

The quiet that fills the air afterwards feels like it’s metaphorically choking Will. He can’t even begin to imagine what’s actually going on inside Mike’s head at the moment, and he hopes by some miracle that he doesn’t think Will is some weird pervert that needs to be put down. 

After what felt like an eternity and half had passed, Mike finally broke out into a fucking smile, of all things, and clasped a supportive hand onto Will’s shoulder, “Will, dude, it’s totally fine. You’re kinky, and that’s…” He swallows, his smile growing even bigger, “That’s cool. I’m your best friend, I won’t judge you.” 

Will just stands there in shock. Well, more so shock of just how well Mike is taking all of this. Will knew he wouldn’t judge him too much, always being the supportive and kind best friend that he is, but this is Will’s sex life they’re talking about here. And Mike is sporting the most happy go-lucky smile Will’s ever seen on him. 

“Well, that’s…” Will’s face is so hot right now, really not expecting that kind of reaction, “That’s good. So, let’s just forget you ever saw anything, yeah?”

Mike gives his shoulder a small, slightly unnerving squeeze, and lets go of Will completely. His smile is still big, teeth and all. “‘Course, Will. What were we talking about again?” 

Will breaks out into a smile himself, though certainly not as wide as Mike’s, and rolls his eyes at Mike’s sweet attempt at making him feel better, “Okay, okay… Night, Mike.” 

Mike chuckles, grabbing onto the door handle and begins to close it, “Night, Will.” The door is quietly shut in his face, and Will lets out a puff of air he had no idea he was holding. 

He’s so relieved, and so grateful that he has such a good friend and roommate like Mike. He knows if it was Lucas, or god-forbid Dustin, that had caught him like that he might not hear the end of it. And he was certainly glad he wasn’t rooming with some stranger either. 

Will went to sleep that night with a content smile on his face, determined to put past the intimate part of him that was revealed to his most favorite person that he knows. 

He thinks to himself, as sleep lulls him under, that Mike Wheeler is such a good best friend. 

Five months have passed since that fateful night that Will has tried his very best to forget. He’s currently standing in his pajamas in their kitchen, stirring up his morning coffee. The pajamas he’s wearing today consist of his favorite oversized David Bowie tee, and a very short pair of baby yellow cotton shorts. 

He yawns like a cute kitten, taking a sip of his overly sweet hot coffee. He’s deeply sleepy this morning, his brain working sluggishly as he starts to process the day. Luckily, he genuinely has nothing to do today since the semester had just finished up last week. Will’s been quietly enjoying his summer break since then, his free time being composed of working on personal art projects and catching up on his film watchlist. 

The time spent hasn’t been the same for Mike, however. A very long time ago, basically since they first moved in together, Mike insisted over and over again that Will getting a part-time job  was unnecessary. Mike told him to focus on commissions that Will would get from his online Etsy shop, which was actually doing pretty well lately. 

So, with Will relying on commissions for his reduced rent, which should honestly be more but Mike urges that he should pay more than half of their rent, he doesn’t have too much money left to spend on himself for personal things.

Mike has all of this covered for him. Will genuinely does not have to worry about food or non-essentials like their streaming services they’re subscribed to, or their monthly couple hundred dollars they put aside so they can have two, huge fun days at the arcade at the end of each month. 

Mike pays for all of this with the credit card he uses that his father gave him, and the money he makes from his part-time job working at their local library. And because the semester is over, they’ve scheduled Mike to come in more often and work longer hours than usual. 

Will is happy for him, of course, he’s been getting more opportunities at work and is hopefully making a good impression on his bosses. Will just misses Mike during the day, is all. He misses his overall presence, his sometimes overbearing, but calm warmth that soothes Will. 

Will is not afraid to admit that Mike is his most favorite person in the whole wide world. And speak of the devil, because Mike drags his tired body into the kitchen to join Will for the morning. He’s already dressed and made up for the day, wearing black jeans and Will’s personal favorite shirt of his, a two-toned navy and slate blue polo. 

Will glances over at him, watching as he takes the Paladin mug Will had bought and painted on for him, out of the drying rack. He feels heat instantly rise to his cheeks, really not being able to resist Mike when he’s wearing his literal favorite outfit combo.

And don’t even get Will started on his side swept hair and large round glasses that makes him look older and fucking delicious. 

“Morning, Will.” Mike speaks tiredly, not wasting any time to make his own cup of coffee for the day. Will watches as Mike puts in significantly less sugar in his than Will ever does. 

“Hey, Mike. Another long shift at the library today?” Will presumes, taking another sip out of his mug.

Mike groans, giving Will the most pleading I just wanna stay home and do nothing face. “You know it. Won’t be back until at least 8 tonight.” 

Will giggles, putting a hand on Mike’s shoulder and rubbing it there in support, “Oh, stop being such a big baby. You’ll be fine, you love the library.”

Mike smiles down at him, clasping his hand over Will’s own on his shoulder, causing Will to blush instantly at the contact. “As always, Sorcerer, you are right.” Mike huffs, and turns to stir up his coffee, taking a long sip of it after.

Will smiles too, feeling gratified because Mike still hasn’t let that nickname go after all these years. Nor does Will want Mike to let it go, he loves that his best friend is nerdy, and incredibly sexy. The two greatest combinations known to man. 

Mike’s face changes a little after he’s done sipping his coffee, a touch of worry now gracing his eyebrows. “So, um, today’s the day we get our grades back for the semester.” Mike speaks in a softer tone, the tone he reserves for Will and apparently for no one else, according to Max. 

Oh. Will had momentarily forgotten about that little detail of what was coming in his day. It shouldn’t be as big of a deal as it is to Will, but his grades and overall how he’s been doing this semester could have been better.

Will gulps, his smile dropping from his face. He glances back over at Mike, a knowing look passing between their eyes. Mike knows. Knows just how much Will has been worrying about this, knows how much he fears this kind of failure. 

“It’s gonna be okay, Will. Everything will be fine.” Mike says to him reassuringly, giving him a sympathetic smile. 

Will looks away from him, staring down at the cooling coffee in his mug. He remembers this one time his Figure Drawing professor had actually yelled at him for making a mistake, causing Will to come back home with tears in his eyes and his current project for said class crumpled up in his palm. 

Mike comforted him that night, by doing what he always does: rubbing a sweet hand on Will’s upper back, making him his favorite tomato soup and grilled cheese recipe he had gotten from Will’s mom, and putting on Will’s ultimate comfort movie, Howl’s Moving Castle. 

Will looks back up at Mike, with some of the saddest hazel eyes he has ever beared at him, “What if… what if I didn’t do good? What if everything just went wrong, Mike?” 

Mike immediately shakes his head, putting his Paladin mug down and gently grabs Will’s Cleric mug to take out of his hands, putting it next to his own. He puts a hand on either one of Will’s shoulders, turning him so he’s facing Mike directly. 

“Nope. We’re not gonna even entertain that idea. You’re gonna get all passing grades, Will. I know you sometimes struggle with self-esteem, but I also know you.” Mike smiles softly, “You’re so smart. And so good at learning new things. You make a few mistakes here and there, but, fuck, Will… that’s what being human is all about.”

Will feels a shiver wrack throughout his body. Mike always knows what to say to make Will feel better.

Will looks up at him, hoping that the absolute love and adoration gleaming in his eyes aren’t showing too much, and gives him a sad smile. Mike, of course, notices and Will hears a sharp click of his tongue.

“How about you focus on something else… like…” Mike trails off, clearly lost in thought for a moment. Will immediately notices when Mike has an idea pop into his head; his eyebrows twitch a little, and his lips curve up into a small grin. “What if I give you a reward if you get good grades?”

Will furrows his eyebrows at him, confused but honestly, intrigued to say the least. Reward? Like he’s some kind of dog, getting his favorite treat if he brings back the stick.

Will stores that thought to the back of his mind, not wanting to delve deep into how that had turned him on just a little.

“What kind of reward?”

Mike chuckles a little, “Nope. Don’t ask. It’ll be a surprise. Something I know you’ll like. Something you won’t ever fucking forget. Trust me, I’ve…” He visibly gulps, suddenly looking a little tense, “I’ve seen it first hand just how much you like it. It’ll be perfect.”

Will feels a little lost, wondering what idea could have possibly popped its way into Mike’s brain. He thinks through just about everything he has ever liked or enjoyed. A few things make its way to the forefront of his mind; maybe a surprise DnD campaign, but that takes months of planning. Maybe a new set of paintbrushes? Will has been needing some, his brushes looking worn and rusted at this point. 

Mike just laughs, taking one last big gulp of his coffee before rinsing it out and putting it back on the drying rack. He grabs his wallet and his keys, stuffing them inside the pockets of his jeans. He flashes Will one last toothy smile before grabbing the front door handle, “You’re cute when you’re confused. Bye! Text me how it goes, so I have some time to prepare for that reward of yours.” He winks at him. 

Before Will can even think about responding to that comment, Mike is out the door as quick as lightning and Will hears the click of the lock turning. He soon realizes he’s blushing like crazy, heat creeping up into his cheeks pretty much as soon as Mike called him cute. 

He takes one last shaky sip of his coffee, wondering about just how far Mike would go to give Will a reward he will never forget. 

Will spends the remainder of his day doing what he’s been doing since summer break started: nothing of significance. He gets to work on his own art at his own pace. His current project, which he tells himself over and over not to stress out about, is a detailed landscape of Lucas and Max’s decorated open-concept apartment. Today, he worked on sketching a perfect recreation of their thrifted couch and Max’s various skateboards hung up on their living room wall.

Okay, and sue him, he did play a little bit of Minecraft and maybe just a little bit of the first three Five Nights at Freddy’s games.

The point is, he was enjoying his break to the fullest, by doing the things he didn’t really get to do while he focused on his coursework throughout this past semester. 

Until 3:00 pm rolled around.

He knew it was coming. He felt butterflies fluttering around in his stomach as he opened up his laptop and pulled up the login website for his school's student portal.

He nervously chews on the edge of his finger as he navigates to the page where his grades have finally been posted. 

He feels his heart leap out of his chest.

All A’s across the board.

Relief floods Will’s body instantly, easing him to relax his shoulders and let out the breath he’d been holding in for about a minute now. 

His highest grade comes from his Graphic Design class, which of course, he was expecting. He excelled at it tremendously, as he had always loved using computer programs and applications to create his art. After all, most of his best art had been his digital media. Mike doesn’t disagree with this, but he does mention how much he loves Will’s paintings. 

His lowest grade was in Figure Drawing, one he had struggled with several times this past year, and yet he still passed.

Will is shocked, but so, so relieved. The first thought that comes to his mind after shutting his laptop is to text Mike the good news. He grins down at his phone as he pulls up Mike’s contact on his messenger app.

Will didn’t even realize how much he was smiling to himself like a lovesick idiot while he was texting back and forth with Mike. He’s just appreciative of his best friend's support, that’s all. Mike is genuinely the most amazing person Will knows, always uplifting and encouraging him to be the best version of himself that he just knows Will can be.

Even though it was mid-afternoon, Will is feeling on top of the fucking world, so he’s stopped caring about wanting to “be dressed” for the day when he knows he’s not gonna leave to go anywhere. He makes his way over to his bedroom to fish out a light blue pajama set from his dresser. A loose fitting spaghetti strapped tank top, and airy shorts that left nothing to the imagination. It’s made out of the softest cotton, with little flowers embroidered in the fabric. He smiles to himself, always feeling the most him when he can wear and stylize himself in more feminine clothing and accessories. 

He’s even thrown out every single pair of boxers he owned, now opting to wear the most comfortable panties underneath his clothing instead. He shuffles around in his underwear drawer for a bit until he finds the most perfect pair of panties; white cotton with the most delicate lace dawning the sides of it, and a small baby blue bow centered in the front of the fabric. It was a bit see-through in the back, but Will liked it like that. Made him feel desirable and sexy all the time. 

He pulls on the panties and his clothes, admiring himself in his full-length mirror attached to the back of his bedroom door. He can even admit to himself that he looks good; having all the right curves in all the right places, and dawning some of the softest skin he’s ever personally felt. Looks like his efforts of putting lotion on morning and night really have paid off.

He plops back down on the couch a few minutes later, feeling like his entire day, no— year had been made because of his passing grades. He needed to tell his mom, his brother, the rest of the party— but it could wait.

Will is still thinking about what Mike could possibly be giving to him later that night, that he doesn’t even want to talk to anyone else.

Harsh light filters in through Will’s eyelids, stirring him awake from his slumber that he accidentally took while lounging around on the couch. He lifts his head slightly from the crocheted pillow that he had been gifted by Jane. He blinks his eyes open, making out a tall silhouette standing in front of their apartment’s front door. The door closes, and the space grows dark once again.

Will sits himself up on his elbows, rubbing the sleep away from his eyes as he squints at the figure, “Mike..?”

The lights hanging above the kitchen island suddenly illuminate to life, and Mike is thankfully standing there, putting his keys and wallet on the marbled counter. 

Will can see that his darkened eyes are just boring into his, a look passing through them that Will can’t decipher just yet. Mike stalks over to the living room, his hands hidden inside his pants pockets. Will furrows his eyebrows at him in curiosity as Mike stares down at him, practically burrowing himself deep into his soul.

Will doesn’t know why, but he feels rooted down to the spot. Mike’s never, ever, looked at him this way before. If Will didn’t know better, he might even mistake it for pure, unadulterated lust. There’s no way it’s that, though.

He gulps nervously as he gazes back over at the Mike looming over him, “Is… is everything okay?” 

Mike’s own gaze travels down his body very slowly. Will suddenly feels exposed, wondering if he wore too little clothing than he should have. Will lets out a tiny squeak when Mike’s fingertips drift against his thigh ever so gently. Why is Mike touching him?

“Everything’s just fine, Will. Are you ready for your reward?” Mike speaks softly to him for the first time that evening.

Will feels like his heart is about to leap out of his chest with how fast it’s beating right now. Mike just barely touched him, barely said two sentences to him, and Will feels his tiny cock start to stir to life in his panties. Oh god, this is humiliating.  

He nods almost instinctively, wanting so badly for whatever Mike might give him, “Yes… please, Mike.”

Instead of giving Will whatever he had planned on giving him, he sat down on the very end of the couch where Will’s feet currently lay. He looks at Will, his eyebrows twitching the way they do whenever he’s thinking intensely about something.

“Okay, but first, Will…” He takes in a shaky breath, pushing his glasses up the bridge of his nose, “Do you remember that one time, I—uh… walked in on you? In your room?” 

Will shakes his head slightly, not understanding what Mike is referring to. He’s walked in on Will in his room without permission loads of times. “…No?” Will replies hesitantly. 

Mike just looks at him, unblinking, “…When you were getting spanked, Will? By some fucker who shouldn’t have had his hands on you?” 

Will’s heart sinks to the floor. Color washes away from his face in an instant. Fuck, why is Mike asking about that?

Will doesn’t even want to answer him, he already feels so embarrassed just thinking back on it. And he can’t believe Mike is bringing this up now. He wanted to just forget about it completely. “Mike, I thought we agreed not to ever bring that up again? This is…” He gulps, his face growing hot, “This is embarrassing for me.”

“No, Will, just—“ Mike groans, clearly feeling frustrated as he slaps a hand to his face, “Did you like it?” He blurts out.

Is Will hearing things right?

He’s sitting up now completely, pulling his knees up to his chest as he rests his back against the couch’s outer edge. He stares at Mike, his blush growing deeper and deeper by the second, “Did I like… what?”

Mike just shakes his head, closing his eyes for a second as he huffs out a breath of even more frustration. “C’mon, Will. I know you haven’t been fucked dumb in awhile, so stop acting like you have been. Did you like getting spanked?”

The tips of Will’s ears are now just as flushed red as the rest of him. Mike is asking him questions that are genuinely none of his fucking business. Will does feel like he’s been fucked dumb, but just missed the fucking part. Because he’s so utterly confused as to why Mike is asking him this. 

“I— what the hell, Mike?” Will spits out, displaying false anger as he gets even more embarrassed as the seconds tick by and he’s still not out of this situation, “Why are you even asking me that? That’s not… That’s not something you can just ask me. That’s…” Will huffs, looking away from him shyly, “That’s private. Something I only discuss with people whom I'm intimate with.”

Mike wastes zero time to say the most absurd thing Will’s heard spill out his mouth this evening, “Then be intimate with me. And let me spank you.”

There are almost no words to describe how shocked Will feels after hearing Mike just declare something like that out into the open. Will feels like he’s fallen into another dimension, where everything is opposite and all of his years of longing have finally meant something. 

“You…” Will laughs mid-sentence, at just how absurd this truly is, “You want to spank me? Mike, are you sure you’re okay?”

The problem is, Mike looks dead-serious about this entire situation. And it’s making Will nervous as hell, but also making an ache start to form in the deepest pits of his stomach. A desire he cannot stop from rising up all the way through his small cock.

“I want to spank you. For doing so good in your classes this year, Will.” 

Will gulps, feeling like the temperature in the room had been increased by a thousand degrees. He cannot believe this is happening, he feels like him and Mike have officially lost their minds. 

“W-Why..?” is all Will can ask with reluctance looming in his voice. 

Mike gives Will a soft smile, and it unnerves him even more. “Because, baby, you deserve it. Wanna make you feel so good you’re crying and begging for more.”

Baby?

Will’s breath hitches instantly after hearing that, his heart beating so fast he feels like he might just pass out. Mike’s been quite direct, and a little pushy too. But, fuck, Will likes it. Will wants to be controlled and told what to do and how to act and wants to be a sobbing mess as he’s fucked stupid into a mattress. 

Can Mike give that to him? Does he want to give that to him? 

“I’ll spank you so good, baby. You’ve just gotta let me.” Mike pleads more, his voice breaking just a little. He sounds desperate, a kind of desperation Will’s never really seen from Mike before. It turns him on just to see how much Mike really wants him. 

Will licks his lips hungrily, his eyes flitting down briefly to how fucking good Mike’s arms look in that polo of his. His eyes trail down to his hands, fingers long and slender. His cock twitches in extreme interest as he thinks about Mike’s palm coming down to strike him, his fingers digging into the flesh of his ass and pulling his cheeks apart to expose his needy hole to the bare air.

Oh my god, Will’s too far gone. He cannot be helped now. His fate now rests in the hands of a very eager, and downright sexy to the core, Mike Wheeler. Will feels like he might just start moaning at the thought of it. 

“Spank me, Mike.” He hears spill from his lips. 

The next thing Will knows, Mike is moving over to the center cushion of the couch, and grasping tightly onto Will’s forearms and pulling him straight across his lap. 

Will gasps at the manhandling, the way Mike situates him perfectly so his stomach lay across Mike’s thighs, his hard dick pressing incessantly against the side of them.

And now, Will’s perky ass is sticking up in the air. He should be mortified; mortified by how he’s laying almost all of his weight on top of his best friend and exposing his butt to him, but he’s not. 

He’s fucking leaking in his panties at this whole situation, at Mike bending him over his knees and showing him a good time. Will squeezes his eyes shut and bites harshly down onto his lower lip to suppress a humiliating whimper. He’s too turned on for his own good.

“Pretty baby, look at you in your matching pajama set. And it’s my favorite color? Did you wear this for me, Will?” He hears Mike coo from behind him. 

A hand rests itself upon his right ass cheek, and he feels the tips of Mike’s fingers slip underneath the hem of his shorts. Short nails scrape across the skin of his buttocks, and Will feels a tear already slip from the corner of his eye. 

God, how he loves to feel small like this. He’s already teetering on the edge of that headspace where he feels warm and fuzzy and everything is right with the world. 

He tilts his head to the side so he can look back at Mike, who's already staring right back at him through his round glasses like he’s the most beautiful thing in the entire universe.

If Will was standing up he would have fallen down to his knees and took him right into his mouth right then and there. 

“Maybe…” Will whispers back to him, earning a small, earnest smile from Mike. 

“You’ve been a very good girl, Will. But, I think you should be bare when I spank you, don’t you think?”

Will visibly shudders at that, jutting out his lip as he nods in response desperately. He feels pathetic, wanting Mike to undress him and treat him like a plaything. 

Mike moves a palm to the back of Will’s head, stroking the tufts of his soft hair gently, maybe even lovingly, “That’s my good girl. Knew you’d want it just as bad as I do.”

His hand slides from the top of Will’s hair down to the nape of his neck, resting there for just a moment. Will feels like his eyes are going to roll back into his brain just because Mike has a gentle hand pressed to his neck, to an area of his body that had always been so sensitive. 

After a while, the hand on his neck slides down over the fabric of his tank, goosebumps popping up across Will’s skin as Mike practically runs his hands all the way down his body. Fingers hook into the hem of his shorts, pulling them down over his ass in one quick swoop.

Will’s shy as he knows Mike’s eyes are raking all over his body, and especially on the white lacey fabric adorning his hips and butt. The panties are opaque, so he knows if Mike wanted to, he could spread his cheeks apart to see his hole sitting right there in the middle through the fabric. 

The next thing that happens is something Will had been secretly craving ever since that fateful day Mike walked in on him. Mike strikes one of his palms down onto Will’s right ass cheek, and Will honest-to-god moans right then and there. 

Mike soothes the aching skin of his butt with his hand, chuckling to himself behind Will. More tears stream down Will’s cheeks, and he dares to glance back at Mike.

He’s got this wide, conniving grin on his face as he asks Will this next question, “What was your highest grade you got today, Will?” 

Will’s eyebrows crunch together in confusion, “Um… 97, I think.” 

Mike just keeps smiling, his soothing ministrations never stopping, “Hm, 97, you say? You think 97 is enough spanks to reward you for your good grades?”

Will’s eyes bulge out of their sockets at Mike’s completely insane request. He tenses up a little bit under his touch, his cock weeping in his panties. “M-Mike, that’s way too much…” Will stammers out, hiccuping a little. 

For too long of a moment, Will thinks he’s dead serious. That is until Mike is laughing, his smile wide and his slightly crooked teeth being barred just for Will. 

Will can’t help but smile himself too, although he has no idea what Mike is laughing about. He feels like he’s falling further for him with every passing second and he didn’t even know that was possible. He thought he’d already reached that point in high school.

“You’re so cute, Will. You looked like you really believed me there for a second.” Mike says, giving his ass a little pat, “How about 20? Is that more… manageable for you?” He smirks at him.  

Will lets out a faked annoyed breath, rolling his eyes a bit at Mike. “Much more manageable, actually.”

“Then can you count for me, baby?” Mike asks in the sweetest voice. 

Will begins to nod, but is interrupted by Mike clicking his tongue a few times, “Ah, words, baby. That’s how this works.”

Will licks his lips a little, looking back up into Mike’s eyes with a hint of a blush on his cheeks, “Yes, I can count.”

Mike gives his ass a light squeeze, causing a small whine to escape from Will’s lips, “Perfect. And um, and just because I’m putting in so much work to do this for you…” He teases, “After every count can you say something else for me?”

Will would practically do anything for Mike. He doesn’t even care what he might make Will say, probably something silly like, “Thank you, Dungeon Master.” 

“What do you want me to say?” 

“I want you to say ‘Thank you, Daddy.’”

Will’s jaw drops to the couch cushions beneath him. Wow, his guess was pretty close. But, still, Mike is into that? Will can’t even judge him, his cheeks heating up more as the thoughts of calling Mike “daddy” in all sorts of situations brew into his mind. 

Mike doesn’t even look embarrassed about what he just said. God, Will wishes he could be like him and say whatever he wants and just look completely fine with it. 

He swallows, Adam’s apple bobbing intensely, “Okay… daddy.” 

The nonchalant look on Mike’s face suddenly vanishes, and is replaced by something much more hungrier and filled with desire. Will isn’t mentally prepared for what comes next.

Mike is suddenly yanking down his panties, pulling them and his shorts all the way down his legs and throwing them somewhere across the room. His hand comes down fast, striking him right across the middle of his ass, pushing a loud, strangled moan from Will.

Will looks back at Mike in shock, and all he is met with is Mike, with his eyebrows raised expectantly, glasses sliding down the bridge of his nose. 

“Count.”

Will’s lower lip quivers as his mouth forms the words, “…One… thank you, daddy.”

Mike groans low, and Will swears he could feel a twitch of Mike’s own cock against his lower stomach. 

Mike’s hand strikes down again, this time even harder, a stinging pain that wrings wet, fat tears out of Will’s eyes, “Two… thank you, daddy…”

Another slap lands this time on his left ass cheek. Will’s eyes roll into the back of his head, “T-Three, thank you, daddy…”

Mike decides to alternate his next few spanks from one side to the other: “Oh fuck— Four, thank you, daddy…” and “Ahh— F-Five…” Will breathes heavily, noticing that Mike is not playing gentle with him at all, “…thank you, daddy.”

On the tenth spank, Mike’s palm strikes against the tops of Will’s thighs a little, and he yelps back in a mix of pain and pleasure, “Ten… fuck, thank you, daddy.” 

Mike coos after that one, rubbing the skin of his thighs a little, “You’re doing so good, baby. Such a good fucking girl for me.” 

On the seventeenth hit, Mike’s hand lands hard against the fat of his ass, and grips harshly onto it as he pulls his cheeks apart. Will shivers underneath his touch as he hears Mike spit and a sudden, wet coldness lands on his exposed hole. “S-Seventeen, oh daddy— thank you…”

A few spanks later, and they’ve reached number twenty, and Will’s ass is so red and in so much pain, he feels like he needs to sit in a tub of ice after this. But, fuck, this is what he dreams about at night. Being spanked to fucking tears by his hot roommate, and it actually happened. 

Mike strikes down on his ass one last time, right in the middle, the sound of it echoing across the floorboards in their living room. “Twenty… t-thank you, fuck, so much, daddy…”

For around one full minute, neither Will nor Mike say anything as he just rests spread across Mike’s knees. He’s spent, his ass and face redder than a tomato. He honestly probably should feel more humiliated, with how wet his cheeks are from crying so much. He feels too good to care, too satisfied with the spanks to his backside that he feels like he’s so deep inside that blissful state that he doesn’t get to reach nearly as often enough. 

There are hands suddenly gripping either side of his waist, and he’s being pulled up to his knees. Mike manhandles him so he’s situated snug in his lap, his cock that’s covered in pre-cum pressing against both of their stomachs. 

Will is blushing as he just looks at Mike for a moment, eyes wide and full of wonder. Mike himself is pretty pink too, panting heavily even though he really didn’t do much overall. Will can feel something hard press against his own cock, and can tell immediately that Mike is aroused. Aroused from this whole situation, he wonders, or aroused from the state Will is in? 

Mike’s eyes dart between his for a brief moment, and his lips curl up into a small smile, “Hi.” 

A giggle bubbles out of Will at that, at the Mike he knows and loves coming back out to say hello to him. “Hi.” Will responds back, trying to fight a wide grin from forming on his face, but ultimately failing to do so.

“How… how was that?” Mike asks him, his hands still on Will’s waist, thumbs rubbing small circles into the soft skin there. 

God, Will is so in love with him. Mike just treats him so, so good. He must be making it quite obvious just how much Mike’s words and touches are affecting him, by smiling like a lovesick puppy all the time. 

“It was so good, Mike. Actually, it was the best I’ve ever had. I needed a good spanking.” Will laughed a little at that last part. 

Mike just smiles up at him with the kindest eyes Will’s ever seen him bare, and it almost makes Will want to cry some more, but for different reasons entirely. 

Mike’s eyes flit down to Will’s dick, which is still standing to attention and in desperate need of relief. His eyes revert back up to Will’s, and Mike’s hands slides down to his hips and squeezes the flesh there, “Can I touch you, baby?”

Will bites back an involuntary moan at that, something he’s been wanting so bad for so long is finally happening. He nods a little, but then suddenly remembers what Mike had asked of him earlier, and says, “Please… please touch me, Mike. I need you.” 

Mike’s right hand lifts off his hip, and barely touches the side of his cock. Will can’t help but buck his hips up into the air, letting out cute whimpers as Mike runs his fingers down the length of him, which wasn’t very much. 

Mike glances back up at Will’s ruined face, and presses the pad of his index finger directly onto the tip. Will fights back the urge to squeeze his eyes shut, as he really doesn’t want to miss eye contact with Mike. He truly looks so hot right now, looking at Will through his lenses like he was a piece of the most beautiful artwork, and it was doing things to him. 

“Can I eat you out?” 

Will chokes back on air, coughing a little as Mike’s words register with him. He really did want to do a lot of unexpected things with Will tonight. 

“Fuck… please, daddy.” Will moans out like a slut.

Mike smirks, collecting a bit of Will’s pre-cum on the tip of his finger and bringing it up to his lips. He sucks it off promptly, his gaze never moving from Will’s shocked own. 

“How about I lay down and you sit on my face?” Mike questions.

Jesus Christ. Is Mike trying to kill Will? Of course he wants to sit on his face. He wants to ride Mike’s big nose until he’s coming all over himself. 

“Yes, oh, yes… God, please, Mike.”

And that’s how they end with Mike, laying down on his back with his head propped up on a pillow, glasses cast aside to the coffee table, and Will looking back at him a little nervously with his fat ass about to plop down onto Mike’s face, “Are you sure this is okay with you, Mike? Will you even be able to breathe?”

Mike fondles with the flesh of his asscheeks, spreading them apart so he can get a good look at Will’s pretty pink hole, all untouched and dry, but it’s about to not be. “Will, I actually don’t want to be able to breathe. Think I’ll just lap at your needy hole forever.”

Will huffs, a pink blush spreading across his face, “Just tap me twice on my thigh if you need me to move, okay?” 

“Move as in ride my tongue for hours and hours?”

Will’s eyes widen, what the fuck has gotten into Mike, seriously?  “Mike, be serious.”

He just smiles a little, giving his ass a little, teasing squeeze. “I know, I know, I was just messing with you, baby. You get so damn cute when you’re all flushed and confused like that. Makes me wanna fuck you stupid on my cock.”

Will doesn’t say anything, doesn’t think he can say anything when Mike just said he wants to fuck Will.

He begins to lower himself, watching as Mike's face disappears below him. He makes sure not to sit fully on him or anything, but enough that his hole is centered with Mike’s mouth. 

Mike wastes no time, his wet tongue already prodding against Will’s entrance. It makes Will jump a little at the sensation, but he immediately melts back into it, circling his hips a little against Mike’s tongue. 

Mike groans against him, licking and sucking at and around Will’s hole. Will quickly becomes a moaning mess, and the waterworks start to come back too, not even realizing he’s crying so much because of Mike’s tongue. He’s way too good at this, and Will briefly wonders if he’s ever eaten out a girl like this before. He shakes that thought out of his head, not wanting to upset himself. 

Mike’s right hand comes around his thigh and wraps around the base of Will’s cock, stroking him in time with his movements. His tongue is now practically fucking Will’s hole, and the noises are absolutely obscene. 

“Daddy—oh! Right there, daddy…” Will moans noisily, probably way too loud, wondering if their neighbors can hear him. Oh well, at least they get to know how well Mike can treat him. 

Mike pushes his tongue deep inside, and Will yelps when he feels a finger being pushed in beside it. His hole is wet enough to be fingered, yes, but fuck, Mike is insatiable. And he’s a messy eater too, sloppy and a bit uncoordinated but Will is having the time of his life. 

Mike rubs his thumb against the tip of Will’s leaking cock, and shit, he already feels close. Mike’s only been eating him out for a few minutes and he feels like he could come just from his tongue. 

The finger inside of him pushes in deeper, and it curls within him, causing Will to let out a punched out moan into the air. Mike’s finger pushes and prods at his prostate, and it feels so good that Will’s gone nonverbal.

He can’t speak any words, can’t even warn Mike that he’s about to come, but just moans and whimpers as Mike’s finger and tongue fucks inside of him, and his hand strokes his dick. It all becomes too much, and Will practically screams when his orgasm finally hits him.

He does kind of end up riding Mike’s tongue, after all. He pushes his hips back against him, letting out little whines as he rides out his orgasm. He feels Mike groaning underneath him, and that makes everything feel a hundred times better. 

He collapses on top of him, his ass moved away from Mike’s face a bit so he can finally get some air. Mike presses one last gentle kiss to Will’s rim, which is now puckered pink and dripping in saliva, and a bit stretched out too. 

“Did you like that, baby? Cause, fuck, I did. Felt like I was about to run out of oxygen with your ass in my face like that. Felt so nice, baby.” 

Will looks back at Mike, feeling completely dazed and ready for another nap, but sees how buzzed out Mike looks. He looks like he’s ready to do more, and Will realizes that Mike’s cock is still poking against the zipper in his jeans. He’s still hard. 

“I loved it, Mike. Felt so fucking good…” He trails off, running a hand down the front of Mike’s jeans to cup his bulge. He gasps when he feels rough fingers wrap around his wrist and yank his hand away. 

“Baby, what are you doing?” 

Will frowns a little, looking back at him with furrowed eyebrows, “Touching you. Is that not okay..?” 

Mike’s face is stiff for a moment, but he then lets go of Will’s wrist and gently rubs the skin right over where his pulse is, “Of course, it’s okay. But I don’t want you to have to lift a finger tonight, yeah?” 

Will frowns even more, because that’s not what he wants. Even though, yes, he is tired and would love to fall right back asleep, he wants to help Mike. He wants to see what his face looks like when he comes. 

“But… I want to make you feel good, daddy.” Will says to him quietly. 

Mike runs his fingers up to Will’s own, interlacing them together with such tenderness Will feels like his heart is about to burst. 

“You can make me feel good, baby. You can make me feel good all while you lay there and look pretty for your daddy, now hm?” 

Will smiles, watching their interlaced fingers together and how perfectly they look interlocked as one. “How?”

Mike’s other hand comes up on his other thigh, running his palm across the skin there, “Let me fuck in between your thighs?” 

Will couldn’t say no to that, in fact it made his tired dick twitch a bit in interest. He had crawled off of Mike, and Mike had stood up to go fetch some tissues for Will to clean him up with.

Will laid back down on the couch where Mike was laying before, his cheeks heated as Mike cleaned him up with the utmost amount of care. 

Will had shyly told him to go get his lube from his bedside table in his room, and Mike came back with the biggest grin on his face, glasses now back on, twirling the half empty bottle around in his hand. 

He unzips his jeans, and pulls them off with his boxers in one fell swoop. He’s fucking eager, and Will’s eyes bulge out of their sockets when he realizes how huge Mike actually is. 

He realizes very quickly it won’t take very much for him to get fucked stupid by Mike.

Mike kneels on either side of Will’s legs, wrapping a hand around his ankles and pushing them up a bit. Mike pops open the cap to the lube bottle, and slathers a generous amount over his aching cock. 

“How about you hold your legs up for me, baby? And keep your thighs closed too, so it’ll feel extra good.” 

Will nods, and grabs hold of his thighs with both arms, pulling them up a bit to his chest and to the side a little. Mike looks like he can take him here and now, but that’ll happen a different day, Will hopes. 

“You ready for me?” Mike asks softly, rubbing a soothing hand over the skin of his thigh. 

Will smiles back at him, “Yes, daddy.”

Mike presses a gentle kiss to one of Will’s knees, and grabs hold of his cock. He guides it towards the opening of Will’s thighs. They both hiss at the same time when they make skin-to-skin contact there. It feels wet, but his cock feels so good rubbing against his thighs. After Mike has fully settled in between them, Will closes his thighs together tighter and squeezes. Mike groans above him, putting his own hands on either side of Will’s head as he begins to rock his hips back and forth. 

The sight is obscene, and so, so close to what it would actually be like if Mike was fucking him. In fact, if someone walked in on them right now, it would look like exactly that was happening. 

Will moans as the tip of Mike’s dick grazes against his balls, and he really doesn’t want to get hard again, so he fights it off. 

“Oh, fuck, baby… you feel so good. Your thighs are incredible. And you’re squeezing me so tight. Fuck, baby, you really know how to make a man feel good.” 

The praise is kind of overwhelming, and now that Will is much more coherent, he’s able to actually answer Mike back. 

“I-It feels like you’re actually fucking into me, Mike. Oh god, I want your cock so bad, I need it, daddy.” Will whines needily. 

Mike seems to love the sound of Will’s begging voice, because his thrusts against him speed up exponentially, “Yeah, you want daddy’s cock? Want me to fuck you so good and so rough you won’t be able to walk? I’ll just keep you home with me all day, stuffed full of my cum. We’ll have to get a plug for your hole to keep it in.” 

Will moans obscenely at that, Mike’s dirty talk is just downright filthy to the bone, “A-Already have one…” Will moans out through the thrust Mike pushes against him. 

Mike groans, a hand snaking its way to Will’s hair and pulling a little bit, “Fuck, baby, you’re a bit of a slut, you know that?” Mike bites down on his lower lip, looking directly into Will’s blissfully fucked out eyes, “That’s okay, though. I’ll just make you my fucking slut. Daddy’s fucking slut. The only cock you’ll be worshipping is mine. Not some assholes who you find in those clubs of yours you and Max like to go to. You’re mine, okay?”

Will loves the ownership, the way Mike doesn’t even hesitate to stake claim as to what’s already been his for years. “Y-Yours, daddy. All—nghh— yours…” 

Mike squeezes his eyes shut for a split second, before he opens them again to look back into Will’s with the same desire he’s been looking at him with all night. “Shit, baby, I’m gonna fucking come. You want my cum? You want my cum all over those milky thighs of yours? They’re so soft and thick, fucking love this body you have.”

Will feels so loved right now, completely over the moon in fact, that he nods profusely, not caring about having another mess made of him again, “Oh, please daddy… want your cum. Come for me, please.” 

Mike’s thrusts get sloppy and faster, chasing his orgasm like crazy. He finally does come with a choked out groan, Will feeling the thick spurts of it land in between his thighs and even a little lands on his own exposed dick, too. 

Mike collapses on top of Will, panting into his ear. Will closes his eyes, basking in the bliss that was this entire night. He couldn’t believe all that had happened, and what a fucking reward he had actually got. 

Mike presses a gentle kiss to Will’s cheek, and it’s so sweet and soft, it seems like Mike really means it. Will turns his head to look at him, and they just smile at each other for a few more moments. 

Will moves his hand to Mike’s cheek, stroking the smooth, freckle-cladded skin there, “Sleep with me tonight?” 

After taking a shared shower, filled with longing glances and shared cheek kisses, they crawl into Will’s twin-sized bed together, getting comfortable underneath the yellow sheets. 

Mike doesn’t even have to ask, already knows what Will wants, and spoons him from behind. A gentle, caring hand strokes against his tummy, and Will sighs dreamily at the touch. 

They don’t speak much for the rest of the night, probably because they’re both so tired from the day they had, but also probably because they’re unsure as to what they are right now. What to make of themselves. 

But, hey, now that the semester is over, they’ve got all the time in the world to figure that out.