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Out of necessity, Derek has fine-tuned a few simple tests for anyone he goes on a first date with.
First, he shows up driving a slightly dented ‘90s sedan that he borrowed from his housekeeper. It’s too easy for people to like a guy in a shiny new Camaro.
Second, he wears his Walmart clothes—a plain black t-shirt, ordinary jeans, and twelve-dollar black-and-grey tennis shoes. He leaves his expensive watch, a birthday present from Laura, in his bedside drawer.
Third, if Derek is paying, he spends less than twenty dollars on the meal. They have a picnic, or they go for burgers, something like that.
Fourth, if things are going really well, like really really well, they don’t go back to Derek’s house. They go to his date’s place, or to a hotel—not a dump by any means, but not a fancy one, either.
Stiles passes every test with flying colors. He doesn’t seem to take much note of what kind of car Derek’s driving or what clothes he’s wearing. His gaze is interested, sure, but not evaluating, not calculating. When Derek suggests burgers, he fist-pumps. He talks all through the date, chewing enthusiastically on his straw and drawing Derek into a heated discussion about Harry Potter, and he never once mentions money. At the end of the date, he doesn’t play games, just draws Derek into a heated kiss in the parking lot, and there’s no doubt they want the same thing.
At the hotel, Stiles is crowding up against his back, kissing down Derek’s neck, before Derek even gets the key in the door. Once they stumble inside, he doesn’t even look around. He just jumps Derek, wrapping his legs around Derek’s waist and sealing their mouths together, confident Derek will catch him, and Derek does.
The sex that follows is… memorable. Stiles tries to fling off his shirt and gets his arms trapped over his head, giggle-snorting as Derek rescues him. The moment he’s free, though, he manages to rescue the moment by shimmying sinuously out of his jeans and going for Derek’s belt, nuzzling in at Derek’s stomach and groaning, low and perfect, against his skin.
That pretty much sets the mood for what follows—one moment Derek is rolling his eyes in fond exasperation as Stiles goes for the lube bottle and accidentally flings it across the room, and the next Derek’s gasping, overcome by how good it is, as Stiles pins him to the bed and sinks his mouth onto Derek’s cock, all the way to the root in one go, smirking up at him as he does it. Through it all, Stiles is creative, impulsive and unpredictable and loud, and it’s fun in a way that sex for Derek usually isn’t. Derek forgets about trying to impress him or judge him, forgets about anything but enjoying it and making sure Stiles enjoys it just as much.
Afterwards, that’s when Derek sits up, sheets sliding low on his hips, and says, “I—I have something to tell you.” He’d meant to say something before things got so intense, but… well, things got intense fast.
“Okay?” Stiles says, cautious but not quite wary. He doesn’t stir from where he’s sprawled comfortably on his back, hands pillowing his head. “Is it the werewolf thing?”
“What? No. You weren’t supposed to know about that.”
“You should do a better job of hiding it, then. I caught a glimpse of fangs and flashy eyes when I was blowing you, and even without that I still could have guessed. Anyway. So it’s not the werewolf thing. Oh god. Are you secretly a drug lord or something?”
“No, I—I just have to tell you I have a lot of money. Not from anything illegal. I inherited it. But yeah. I’m rich. Tonight I’ve been acting like I’m not, but I am.”
Derek holds his breath, wondering if Stiles is going to be irked, or if—like some of Derek’s previous dates—he’s going to look a little too interested and start asking some suspiciously specific financial questions or ask Derek to buy him something.
Stiles, though, doesn’t react. After a long silence, he finally says, “Oh, you’re done? That was it?”
Derek nods.
“Oh. In that case… Dude, I know. That’s not even your car you’re driving. Do you seriously think I didn’t google you and run a background check, the whole nine yards, before getting in a car with you? The last person I dated turned out to be an incubus, and the one before that turned into a lizard sometimes. You just never know with people you meet on Tinder.”
Derek is seriously going to ask to hear that story later, but… “How did you look me up when I never told you my last name?”
Stiles shoots Derek an unimpressed look. “Yeah, like that’s a real mystery. I went to school with Cora. I knew who you were the instant I saw your photo. Well, okay, that’s a lie. It took me a few seconds, you look a little different than you did back in high school. But you get my point.”
“Oh.” Derek is thrown. This has never happened to him before. Does this invalidate his whole first date test?
Stiles sighs and scratches lightly at the dark hair on his stomach, unconcerned. “Look, dude, I won’t lie, it’s nice to have money, and it’s especially nice to have a shit ton of money. You’re probably not going to find many people who would disagree with that. But I have enough money of my own to be comfortable. Do you know why I really wanted to go out with you?”
“I assume it’s because you liked my picture on Tinder.”
“Well, yeah, I’m not blind, but… Okay, I don’t know if you even remember this, but there was this one time in high school that Cora invited me over, along with a bunch of other nerd kids from our grade? It was a board game night, and in the middle of it you wandered in. You were in college by that point, but I think you were home for winter break and bored. We were playing Trivial Pursuit, and until you walked in, I was wiping the floor with them. Then you sat down and beat me like it was nothing. You were such a cocky shit, and you made me laugh. You could think on your feet, and you obviously knew a lot. You could keep up with me.”
Derek frowns, thinking hard. All he can come up with is a vague image of a kid in a plaid hoodie and buzzcut. “I remember that night, but I’d forgotten that was you.”
“Yeah, well. I was a lot skinnier and weirder back then.” Stiles shrugs, unbothered. “What I’m getting at is, I always thought it’d be cool to hang out with that guy again sometime, and you know what? So far it’s been supremely cool. I’ve had a great time. I like you about as much as I did then. Well. More, actually, now that I know how well you give a blowjob, but if you’re the romantic type you can forget I said that.” He winks. He’s impossible. “So, that kind of stuff matters a whole lot more to me than whether you’re sitting on piles of cash.”
Derek believes him, and when Stiles asks him out again the next morning, Derek doesn’t even hesitate to say yes.