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Midnight Monopoly

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Stiles wakes up, the sun shining on his face. It’s probably somewhere in the afternoon, but he still feels tired. Plus, his mouth feels and tastes kind of gross. He needs a tooth brush. He rolls out of Derek’s arm (which is something he’s going to think about when his brain is fully operational again) and goes to the bathroom.

Wow, he really looks like shit. He’s paler than usual and there are bags under his eyes. There’s a crease on his cheek, probably from Derek’s shirt. Derek, who he was using as a pillow. Derek, who let him use him as a pillow. The same Derek he’s been crushing on for a while and has been making for to ask out. Big plans. He hopes his drooling on Derek hasn’t ruined those plans.

Stiles snorts when he finds the extra toothbrushes. Derek tries to discourage them from crashing at his place, and nobody has the heart to tell him that Hello Kitty toothbrushes really won’t do the job.

As Stiles brushes his teeth, memories of the night before start seeping back in. Finals were over, high school was over, they’re finally free and they wanted to celebrate. It started out pretty normal, with movies and pizza. Malia got bored after two movies, started wandering around the apartment and found a box with board games. It didn’t take long for them to decide that they would be playing monopoly.

The thing about monopoly is that it can take a while. Hours, in fact. Scott and Kira fell asleep on the couch around three, and the rest of them decided to start a new game. It soon became obvious that Stiles was winning, he was loaded and owned quite a few of the more expensive streets, so Lydia and Malia started working together. It became a vicious battle between Stiles and the two girls, but the only person who started losing was Derek. Partly because he kept ending up in jail. It had seemed logical for Stiles to help Derek out, become his “sugar daddy” (Stiles can’t believe he actually used those words).

After weeks of nothing but studying and finals, Stiles couldn’t be blamed that his brain was fried. No, every horribly embarrassing thing he did and said last night was because of the American education system, not Stiles.

So he bought Derek streets, and houses, got him out of jail (‘Just like old times!’). And during the game, he moved closer and closer to Derek, until he was practically sitting in the guy’s lap. At that point Stiles barely paid attention to the game anymore, all his focus on Derek. They started talking about random things. Well, Stiles talked, Derek mostly listened.

Stiles wants to bang his head against the wall when he remembers all the things he told Derek; like that he can fit an entire packet of Twizzlers in his mouth (he’s pretty sure he also added a wink), had a unicorn obsession when he was five, which was followed by a dragon obsession. He hadn’t gotten obsessed with werewolves until he was sixteen, though (another wink). He whispered to Derek about breaking into the school library and getting stuck reading about Louis XIV in the biography. He told Derek that he can’t sleep facing his room, because it feels too big, and about the time Scott made him laugh so hard he’d squirted milkshake out of his nose. He told Derek he never locks his window, in case Derek needs to hide in his room again. He told Derek about his obsession with the Mets (although Derek already knew that), what his favourite porn is, that he’d once almost accidentally bought a Faberge egg in an online auction.

Stiles had whispered most of his secrets to Derek last night, some things not even Scott knew. But, of course, it didn’t end there. Stiles starts thinking up escape plans as he remembers what happened after the game.

Despite Lydia and Malia’s best efforts, he won. He had most of the money and was dancing around with it. He danced around Derek, raining the money down on him. Derek smiled (gods, that smile) and congratulated him. Stiles demanded kiss for a prize and Derek obliged.

Oh god.

He kissed Derek.

He kissed him while he was sleep deprived and tasted like pizza, Twizzlers and Cola.

He kissed Derek.

‘Stiles, you okay?’ Derek asks from the other side of the door.

Stiles’ heart is going crazy. Derek must’ve been able to hear it from the living room. Stiles quickly spits out his mouthful of toothpaste and takes a deep breath. ‘I’m fine, just… almost choked on the toothpaste.’


Stiles sighs, rinses his mouth and splashes water in his face. He can do this. He needs more sleep and has grease stains from the pizza on his shirt, but he can totally be cool around Derek.

When he steps out of the bathroom, Derek passes him, smiling at him and brushing their fingers together before he closes the door. Stiles stays frozen, staring at the bathroom door until giggling from the living room catches his attention.

He finds Malia, Lydia, Kira and Scott hunched over, watching something on someone’s phone.

I make it rain! I make it rain!’ Stiles’ voice sings over the tiny speakers.

Stiles almost runs for the door, but the pride in Scott’s eyes when he looks up at Stiles keeps him in place.

‘Dude, did you really kiss Derek? And ask him out?’

Stiles groans. Amongst the thousand confessions, Stiles also told Derek about his plans to ask him out. They weren’t fully formed yet, but Stiles had confided in him that it would involve a lot of flowers, music, possibly a dance number, and a poem. And Derek-

‘Yes, he did,’ Derek says from behind him. He wraps an arm around Stiles’ waist and pulls him close, nuzzling into his cheek.

Stiles goes willingly. He remembers everything now, including how he’d ended up sleeping in Derek’s arms. After the kiss, they’d curled up on the floor, Stiles telling him all about his plans for Derek. And Derek confessing the plans he had for Stiles. Their voices had gotten softer, the pauses between sentences longer, and eventually they’d fallen asleep.

‘I still can’t believe you said yes after all the weird crap I told you,’ Stiles says, shaking his head.

‘At least now I know exactly what I’m getting myself into,’ Derek smiles.

‘Doubt that,’ Scott snorts.

‘Ha,’ Lydia and Malia say at the same time.

Kira tries to hide her laugh behind her hand.

‘They’re kinda right, you know,’ Stiles admits.

‘I know.’