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His first was because he was Done. Capital D, no exceptions, and all-encompassing. Done with werewolves, done with lying, done with mountain ash and wishful thinking, done. So, when the hunter burst into the tattoo parlor just after the artist finished the second M, he was surprised to find he felt more adrenaline than annoyance, even once the pack came crashing through the door a few minutes later. Sure, he still shouted at Derek (following him, rogue hunter suspicions or no, without at least giving him a heads up text was Not Appreciated At All), but he postponed his carefully worded explanation of how very done he was.
Even the aftermath was more satisfying than he expected -- the flash of guilt/sadness/memory from his dad when he saw "MOM" in bold across Stiles' arm was quickly overwhelmed by shock and anger that he'd used a fake ID and gotten it done in the first place. It was good, though, it was something he'd done, something he could admit to and look his father in the eye after. That didn't mean it was anything less than a year and a half of sharpie'ing the heart in before he was able to get it finished, but he had enough going on that it wasn't exactly a hardship.
By that time, he'd already found out from Deaton that there were things you could write on your skin to strengthen your will, or for luck, or protection, or any of a hundred other things. That they could be done with less permanent means helped, and let him practice while he was still "too young" to finalize anything.
He got the triskelion the day after he turned eighteen. Scott hadn't so much joined Derek's pack as stopped insisting he wasn't a part of it, and Stiles needed to say he was in this for the long haul without actually confronting Derek with feeling words. College was at the forefront of everyone's minds and Derek twitched almost as much as his dad did when the acceptance letters started dribbling in. Coming home with his hand stinging was the easiest way to show he would be coming back, that his roots were too far set in Beacon Hills to ever let him fully leave.
But he was leaving. He needed it, they all needed it. To learn more than what they had in their little comfort area. Stiles met Harrison at college, who convinced him to try gauging about a month before they broke up. It was a good exercise in patience, and helped him keep track of how long he'd been away -- how much he'd grown. He got into the habit of picking up two or three tattoos each time he moved up a size. Mostly useful ones, for healing or protection, but also piecing together a larger image underneath the somewhat clichéd "mom" he'd started with. It was haphazard progress, and he just shook his head and grinned when anyone tried asking what it would be. He'd made a deal with himself that he couldn't finish the wolf without explaining everything to his dad, and he held his hand over the still-warm skin as he did his best to look anywhere but his dad's face and tried to find the right way to unravel all the lies he'd been telling.
Scott joked that Stiles was the only person who could get a mohawk and have people consider it a long hairstyle. He let it grow out evenly, at first, for just long enough that it almost felt normal. Stiles had gotten into the habit of snatching Derek's sunglasses, because fidgeting with them or hopping out of Derek's reach was better than twirling his hair like some fourteen year old girl. The first time Derek grabbed his hair to keep him from ducking away, his mouth went dry, and he nearly dropped both the sunglasses and his keys. Neither he nor Derek moved until Scott ran up, rambling excuses for his tardiness, and he found himself reaching to touch his hair even a few days later. At the end of the week he buzzed the sides, not sure if he wanted more or less of the nervous feeling Derek had inspired.
Derek, it seemed, had better things to do than get caught up in mixed messages, though, and he slammed Stiles into a convenient wall that night, apparently so that he could better breathe heavily on Stiles' face. Stiles tolerated this for all of a minute before he kicked at Derek's ankle. "Not that this isn't cozy," he said, raising his eyebrows suggestively, "but did--"
Derek cut him off with a kiss, and things quickly escalated from there. The rest of the pack (sans Scott, who was still not-quite-committed anyway) made just as many married jokes once Derek and Stiles were going out as they had beforehand, and even Stiles' dad wasn't hugely surprised. Pretty much the only change was that Allison kept lighting up with a huge smile every time she was in the same room as they were, and Scott made the most ridiculous faces, like he kept forgetting and re-realizing what "hey, okay, I'm going out with Derek, don't be weird" meant.
They didn't exactly talk it out, what being together means, but what they have works for them. They've been doing it forever, in one way or another, just like Scott and Allison's star-crossed lovers on-again off-again is somehow working, and Lydia and Jackson's power couple thing has been going strong. Scott finally proposes to Allison in the summer, and Stiles insists on a not-bachelor-but-pack-party in Las Vegas, because all of them need a break and who is he to turn down gambling and alcohol?
He's maybe a little trashed (hanging with people who couldn't find a buzz if you ran beer into their veins is not good for him, it still feels like a challenge) when he brings it up, but standing outside the tattoo parlor with Derek and matching "rings" newly inked on their fingers feels like a new beginning and the best decision he's ever made.