IT characters x reader

The bookstore ( henry bowers )

a henry bowers imagine where he meets the reader at a bookstore but she's richie tozier's older sister and she's just like him but flirtier?

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You wracked the many bookshelves, looking for a book for your history class. You came to this book store in particular, because it was in a quiet area of town, and not many people came here. Here was of course the town library, but the chance of finding the book you needed was slim due to the rest of your class likely already have taken all the copies. Finally, after about an hour of searching the bookstore, you found the book. Grabbing it, you pulled it out of the shelf carefully, smiling down at the cover.

You'd been stressing over and procrastinating doing said history project for awhile now, and now you'd finally get it done and out of your way. You knew once you had it done it would be a relief.

As you glanced up to where you recovered the book, you saw through the crack someone walk by; they looked oddly familiar, almost like... no, it couldn't be him. Why on earth would he come to a bookstore? He had no purpose here, and he always teased kids and/or bullied them for stepping foot into a library, so he wouldn't be here. Though that boy looked so much alike him, and it was a small town..

Your suspicions were answered as a focused Henry Bowers came around the bookshelf separating the two, scanning the row. He hadn't noticed your presence, which was probably for the best, because you had an awestruck look on your face. Henry Bowers, in a bookstore. That's something you never thought you'd see. "Never thought I'd catch you at a bookstore, Bowers." He jumped, eyes blown wide when his gaze fell upon you. "Tozier.." He greeted, not at all seemingly happy to see you.
You weren't exactly his biggest fan; nor was he of yours. Mainly because of your little brother, Richie. He was a primary target for the infamous Bowers' gang, and tended to get bullied a hell of a lot. You, being his big sister, took upon standing up to Bowers, not only for Richie, but for all of his friends as well. Henry tried to pick on you, but no one backed him up, and you had no reaction, because frankly you didn't care. It bored him, and he gave up that idea quickly.

"So what brings the infamous Henry Bowers to bless a small bookshop with his presence?" You teased, approaching him slowly. "I-" Henry started, but he nothing followed. He didn't know what he could say, or if there even was anything he could say, to excuse what he was doing here. The real reason he came here was too embarrassing to share with his friends, let alone someone like you, who could easily ruin his reputation.

"Aww, the all powerful Henry Bowers like to read?" You mocked, laughing slightly at your horrible impression of him. He only scoffed, but avoided your gaze. "No need to be embarrassed, Bowers. Nothing wrong with a little book from time to time." You said, looking down at your history book. You glanced back at him, only to see a nervous, unsure expression on his face.

"What?" You asked, genuinely confused. "You aren't going to run and tell everyone that THE Henry Bowers was found in a bookshop?" He asked, and by the tone of his voice, you could tell he thought you'd actually do so. "I'm not like that, Bowers. I know we don't know each other that we'll, but I expected you'd know not everyone cares about tearing each other down to make themselves feel better." You said, seriously.
Turning on your heel, you went and checked out your book. Henry followed you out of the aisle, and waited patiently for you to make your check out. He thought about what you said, and you were right; he hardly knew anything about you. Usually, it wouldn't matter to him, but something about the way you'd just acted now, refusing to expose his secret to the whole town.. he felt like he owed you.

He'd caught you just before you exited the building. "Hey, Y/N.." he called, and you turned, looking at him with eyebrows raised. "Thanks. You know, for not telling everyone." You stood there, mouth agape. "Did the Henry Bowers just apologize?!" You exclaimed, and he chuckled. It wasn't a maniacal cackle like he usually did, it was a real, genuine laugh. That's a sound you never thought you'd hear, but.. surprisingly, it warmed your heart.

"I want to make it up to you. Friday, after school? I'd say during school, but you don't seem like the type to ditch." He said, calmly. You cocked an eyebrow. "Is that a challenge?" You tested, and Henry looked taken aback. "I didn't mean it like, actually, yeah. Yeah it is a challenge." Henry said, smirking. "You're on, Bowers. Friday before school, meet me at the Quarry." You said, and he nodded.

You smiled, walking over to him,quickly pecking his cheek. "Great. See you then." You said, giving a quick wave and with that, you were gone. Henry, gently with his hand, touched the spot where your lips had met his cheek in disbelief. He'd never thought in a million years would he have a date with you. You weren't feeling much different. It was overwhelming; Henry Bowers, the boy who bullies your brother and his friends, asked you on a date. And you said yes.

Let's just say, that history project was long since forgotten.