The first time he does it, takes an ad out in the daily newspaper that says something along the lines of '20 y.o. male seeks 18-30 y.o. male with which to cuddle contact 123-4567 for more', he does it because Scott dared him to. The reason he actually puts in a number is because he realizes that it's actually a good idea and he wants someone to cuddle with. The number goes to a prepaid phone so he can sort out the weirdos and crazies and doesn't have to give out his real number. He eventually settles on someone named Isaac to be his cuddle buddy.
He lets Isaac know that this is in no way romantic and only because he is sick and tired of cuddling with his pillow and he would rather do it with a real person. Isaac is perfectly fine with this and Stiles learns later that he suffered from a severe lack of affection as a child. His therapist had recommended he try and find someone to form that kind of bond with, and then he saw Stiles' personal ad, and decided to try it out.
Stiles isn't a therapist but he can see the logic behind it and they meet about three times a week and just lay and talk and hug and sleep and it's just what both Stiles and Isaac need. Sometimes Stiles wakes up in the middle of the night and calls Isaac and he comes over and other times it's Isaac who calls and just needs someone else to be there with him. They start hanging out outside of cuddling and they become really good friends.
This continues on for six months and Stiles has been sleeping better than he ever has which means he's also doing better in school and concentrating more and he's perfectly content for this arrangement to last forever. Then one day Isaac starts bringing up a girl in his class while they're laying together and Stiles encourages him to go for it.
Three weeks later Isaac is lying on Stiles' stomach as Stiles runs a hand through his hair and he tells Stiles that he's going out on a date with her this Friday and Stiles suggests that he wear his black collared shirt and pack a picnic and take her to the park because girls like odd dates. A month after that Isaac tells Stiles that Erica, the girl he's been seeing is amazing and wonderful and doesn't care that he'd rather cuddle than have sex and Stiles sees where he's going and tells him to go home and that he wants to meet this girl sometime. Isaac smiles at him and leaves.
The next day Stiles puts the same ad in the newspaper.
The second person he decides on is named Jackson and the first time Stiles sees him he asks why he hasn't seen him in porn, which gets a little awkward but thankfully Jackson is conceited and takes it as a complement.
Jackson was adopted as a child and even though his adopted parents liked him, they never loved him, or that's what Jackson thinks even though Stiles is pretty sure he was loved and cared for by his adoptive parents and he just has the lowest self-esteem he's ever seen in someone who is so narcissistic. But Stiles doesn't really care because that means he gets to lay against the not-model's model abs and can wrap his arms around something other than his pillow, something that can hold him back.
They talk sometimes, never as naturally as it was with Isaac, and somewhere along the line they start having sex but they don't hang out like Isaac and him used to do and whenever Jackson brings hanging out up he avoids the topic. Or he reminds Jackson that this isn't romantic but purely needy and slightly primal and Jackson gets angry and leaves and Stiles is left annoyed and un-cuddled and he wonders if he should end things with Jackson.
Jackson is the one who ends it only two months after it began, and it isn't amicable and Stiles just lets Jackson yell at him while he sits on the bed with a stoic expression which just pisses Jackson off even more and he leaves, this time for good, saying, "Don't call again, and I won't!" And he doesn't and neither does Jackson but Stiles doesn't put the ad back out there yet.
He meets with Isaac for lunch one day with his girlfriend and it's the happiest Stiles has ever seen Isaac and he's a little jealous but more of their relationship like he is with Scott and Allison and less because a tiny part of him wishes he cared about Isaac as much as Erica does. They talk about school and classes and potential graduation times and Isaac always has his body pointed towards Erica and she is always touching Isaac in some way and Stiles is so happy for them.
When they leave the couple gets up at the same time and Isaac put enough money down for all of them and Erica laces her fingers in Isaac and Stiles wonders if that is what he needs. That a girl might be less 'something' and more 'everything' and the next day Stiles puts out the same personal ad but adds the letters 'fe' before the male.
The girl he chooses to cuddle with is named Lydia and Stiles swears the sun shines out her ass. She's as close to perfect as Stiles has ever seen, being both ridiculously smart and ridiculously good looking. Stiles finds that he loves to rest his head between her perky breasts and loves the way she strokes his head. He wonders if this is how Jackson felt before they stopped.
After a month he thinks he might be in love with her, he tells her thusly and she merely giggles and tells Stiles to go back to sleep. He's never sure why Lydia wants to be cuddled. Why she wants someone to sleep with, but not sleep with, but he figures it's the same reason as his and it makes him even surer that he's in love.
When they're together he likes to push up her shirt or camisole or dress to show off the taut skin of her abdomen. She'll giggle as he kisses around her belly button but if he strays too far up or down, or if he adds too much tongue she'll push him away and then rest on his chest where he can't help but draw lazy circles with his fingers on her back.
He's more awkward with Lydia than he ever was with Jackson or Isaac but Lydia seems to find it endearing and he doesn't really try to change it. Eventually though, she gets bored of him. She starts coming less and less and when she does she's distant and always leaves just a little too early. He feels her pull away and even though he thought he loved her, he doesn't pull her back in. Just waits while it fizzles out. One day, seven months into their cuddle fest, she comes in, tells him she met someone, and then she leaves.
Stiles lounges around his house for three days wondering what he should do with himself. He wonders if he should bother putting the ad in the paper again, if he does he'll take off the two letters he added the last time, one girl is enough for him. Scott finally comes over to see him as he hasn't contacted the outside world in three days and convinces Stiles to place another ad, if only to raise his spirits a little. He changes his age, as he turned twenty-one five months ago, deletes the letters 'fe' and sends the ad into the newspaper, whose editor is probably laughing himself silly because of how many times he's seen the same personal ad.
He picks out someone named Danny for his next cuddle. The first time they meet it is at a hotel, which is where he's met all of his potential cuddle partners because he's not stupid enough to let someone into his house who he's only talked with on the phone. They're awkward at first, as all of his meetings usually are, but they strip to their boxers and Stiles gives him the "this is only cuddling" speech that he's basically memorized and Danny nods, says he knows and they settle into bed.
He tells Danny he can talk about whatever he wants and Danny starts going off about some guy that he's known forever but doesn't even think about him the way Danny thinks about him. Stiles presses for more details and Danny lets slip that his crush's name is Jackson, and then memories come flooding back to him about the rare times Jackson talked about his life and they were always about a guy named Danny and Stiles shoots up in bed. He gets Danny to give him Jackson's last name and it's the same person who stormed out on Stiles eight months ago.
He gets up from the bed, calls Jackson telling him to meet him at the hotel and giving the room number, basically begs Jackson to come over, and fifteen minutes later he's answering the door.
Jackson pushes past him then, noticing Danny, looks back at Stiles but Stiles just motions him forward and starts to spew off a bunch of word vomit that basically boils down to "You two should get married and have babies." Jackson looks at Danny and Danny looks at Jackson and it takes everything Stiles has not to push the two together. Eventually though Danny takes a step closer and then Jackson does and finally, finally, Danny kisses Jackson and Stiles slips out, because staying would be rude.
This time Jackson is a lot more amicable to Stiles and they even hang out with Danny sometimes. Not as often as he hangs with Scott and Allison, not even as much as he hangs with Isaac and Erica but there is hanging out and it makes him feel good because anyone hating him is like a knife to his chest. The only problem is that everyone he seems to be hanging out with is in a relationship and it sucks being the third wheel. Even with those he isn't hanging out with, Lydia, those who he keeps in touch with on Facebook or through email he seems to be third wheeling. Maybe he's just at that age where everyone's in a relationship while he's ten chapters behind just trying to figure out who he is.
Stiles doesn't put another ad in the paper.
He still gets calls from the one that Danny called for. That's how he meets Derek. Oh God. Derek. The first time Stiles sees Derek, he feels like his life has been coming to this. That every moment before that one was just preparing him for that one. If that were true, though, his life did a shit job of preparing him because the first words out of his mouth weren't actually words, more a jumble of letters and sounds. In comparison, Derek's first words were an elegant, "You must be Stiles."
Derek is a brooding brood monster who never cracks a smile. Or he doesn't crack a smile in the first ten minutes that Stiles knows him which greatly concerns Stiles. He feels resolved now to make this person (this brooding, perfect person who Stiles feels inexplicably drawn to) smile. So he talks. And he talks. And he talks. And Derek doesn't tell him to shut up but he also doesn't give Stiles the smile he wants so desperately and even Jackson smiled before the one month mark. But Derek keeps coming back and Stiles takes this as a good sign, is desperate to take this as a good sign.
Stiles is drawn to Derek even more than he was drawn to Lydia, although they both have a habit of not sharing much about themselves. Stiles doesn't tell Derek about his feelings, won't make the same mistake as he did with Lydia, he doesn't kiss the abs that are on display every time they sleep together, he doesn't let his eyes linger on the waistband of Derek's underwear. He just lies across Derek's chest and talks about everything as Derek draws figures into his back.
Even though Derek doesn't speak much, there are some things he gleams from the information he does give. First, he's about five years older than anyone he's ever done this with and six years older than himself. Second, his family is either not a part of his life or are dead because he always refers to any of them in the past tense. Addendum to the second: never mention anything about his family because it turns his face from passively to actively angry. Third, he's a firefighter and knows Stiles' father, the Sheriff. Fourth, he likes to tease Stiles and does not know Stiles' father but does know of him. He isactually a firefighter. Fifth, he pretty much doesn't talk with everyone he knows.
Stiles is okay with all of this, with all of the things he knows about Derek, with how much he wants to know more about Derek. Sometimes he wonders if it would be weird to look him up online. Sure Stiles did a cursory look at Derek when he first decided to cuddle with him but that was mostly checking his Facebook and seeing if he has a criminal record.
Stiles wants to know everything about Derek, but he channels that into telling Derek everything about himself. He tells Derek his hopes and dreams, how he's worried about graduation, how he's worried about getting a job, how he thinks that Scott and Allison will get married before he turns twenty five, how he sometimes dreams about his mother, how he worries that he may never find someone who will love him.
One day, three months and thousands of secrets in, Derek asks, "Do you do this with everyone?"
Stiles looks at his shoes, he is about to leave Derek's room for class, "Do what?"
"Say all your deepest secrets? I've seen your ad before. You've told me about the others. Do you talk them to death too?" Derek takes Stiles' hand in his and starts making slow circles with his thumb.
"I'll stop." Stiles says, unusually frank in a stressful situation. He pulls his hand away from Derek.
"Try not to regret those words." Stiles says with a laugh, running his hand over his face. When he turns to look at Derek, he sees that the brood monster has a smile on his face. Stiles dance his fingers over Derek's lips. "Careful, you might hurt yourself." At first Stiles thinks that maybe he's dreaming but he's pretty sure that Derek kisses his fingers.
Stiles moves closer to Derek and slips his hand from Derek's lips. He pauses just above Derek's head but then Derek's hands move him closer. They share a light, tentative kiss and its perfect and Stiles never wants it to end, but then Derek's licking at his lips and he thinks that he likes this even more. When they finally pull away, Stiles has repositioned himself on the bed and kicked off his shoes. "Tell me your deepest secrets," Stiles pushes because they've kissed and he feels he can do that now.
Derek pauses for the longest times and Stiles begins to worry and then he feels awkward and he gets up to leave again, because really he does have classes and that's better than feeling awkward about Derek. He gets stopped half way up by Derek who pulls him back down and frowns at him. "Ju..." Derek begins but then retracts and shakes his head, "I'm trying to figure out where to start."
Eventually Derek finds a good beginning and Stiles learns about everything, about the fire, about living with Laura, about Laura's death in a car accident, about getting a job in the fire department, about finding Stiles' ad, about the instant attraction to Stiles, about how he too is terrified of what the future holds, and how he sometimes wonders if he should go back to school and get a degree in something other than EMS, about how he wonders if he'll come home every time he gets a call. In between the confessions there are make out sessions and Stiles is more than happy to miss his classes for this.
And something within him knows that he'll never have to take out an ad again.
A year later finds Isaac a father-to-be with his girlfriend Erica and Stiles knows that it's the best thing that could happen to Isaac. Stiles also knows it's the most terrifying thing for Isaac since his own father was such a bastard. The most important thing though is that Stiles knows Isaac will be the best dad in the world, as evidenced by the way he treats Erica and the unborn baby right now.
A year later finds Jackson and Danny in a rather tumultuous relationship that is only slightly more on than off. They don't fight so much as Jackson yells at everything but Danny and Danny slowly slinks away from Jackson. But when Jackson isn't mad at the world, and Danny realizes he gives more than two shits about Jackson they're fairly happy and everyone else in their life is pissed that they don't realize that they are perfect for each other and should just get married and adopt babies and live happily ever after. Okay, Stiles is really the only person who gets mad, but he also thinks that he's almost convinced Allison to feel as mad.
A year later finds Lydia with her fifth boyfriend, seventh lover, since the one she left Stiles for. All Stiles wants is for Lydia to be happy, for Lydia to find someone as intellectual and beautiful as she is. They don't talk that much, only send emails and Facebook chat occasionally but he can tell she's not ready to settle down. So even though he wants the fairytale life for her, she obviously just wants to date around and enjoy her youth.
A year later finds Derek staring at a ring in the palm of his hand. It was his father's: a simple, thick gold band with an infinity sign inscribed on the inside. He'd heard the story of ring a thousand times. How his mother and father had dated for years, years, and his father was dragging his feet on the proposing thing, but they already talked as if they were going to be forever, and finally his mother had gotten tired of waiting and bought the ring and proposed to his father. It was one of the few things that had survived the fire. One of the few things Derek truly treasured in his life. So he inspects the ring in his hand and thinks about giving it away. He thinks about giving it to the one thing he cares about most.
A year later finds Stiles as the Best Man at his best friend's wedding, he totally called it. It also finds him graduated and heading to law school, which is probably the last place he ever thought he would be, but it also sort of makes sense because lord knows he's broken enough laws to defend against them.
A year later finds Stiles so much happier than he was before. And he didn't even know he could feel any better. There was always something missing and Derek wormed his way into his life and filling all the missing pieces.
A year later finds Stiles where Scott and Allison were six months ago, where he knows Erica and Isaac will end up, where he wants Jackson and Danny to end up, where he worries that Lydia will never be.
A year later finds Stiles crying and nodding and taking. Taking so much from Derek, but also giving so much.
A year later finds Stiles engaged to Derek.