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mikayla

@tomhollandsboo-blog

multi fandom girl
I take requests !
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Simple minds

REQUEST: hi !! could u write a really fluffy henry x female reader fic where he kinda confesses to her all blushy and flustered and they go out on their cute first date and she’s really sweet and he’s flustered the whole time but makes a move at the end sorry if that’s too much lol but thank you !!! I really like your blog ! <3

A/N: I am a giant slut for fluff prompts but Henry Bowers is a bitch to write in character for these things. So it might not be as fluffy as you want it. This is part one of two. The second one will have cuter scenes, I promise. 

Closely linked by history and similar interests, Vic and Belch have been with Henry through every crush the boy has experienced. With many of them being superficial and almost always fleeting, they’re unsure if they’ve ever seen him genuinely like someone before. If he ever did, he hid it well behind a callous persona; a good chance why his romantic relationships never blossomed into anything more than one-sided disdain.

“The arcade got a new game.”

“I don’t get paid till Friday.”

“Take some kid’s lunch money.”

It’s a scripted conversation. One that varied depending on the news but never progressed past anything that could hold Henry’s interest when you were present. The introduction to Careless Whisper plays stagnant in his mind as watchful eyes follow your every step with a friend by your side. Just looking at you makes his stomach turn and he can’t pinpoint if it due to disgust or infatuation.

“Bowers.” Patrick hits the daze’s blonde in the arm, causing him to be abruptly jarred and defensively jaded.

“What?”

“We’re skipping next period for the arcade. Let’s go.”

Henry waves off the offer, watching you say your goodbyes to you friend then detouring through the door nearest to where his gang stood. Without much of an explanation, besides a brisk “Go without me.” He ditches them, ducking into the class the two of you shared for that period.

He takes the desk right behind yours and sets the trap. “Shit.”

On cue you turn your body towards him and quip a smile. “Lemme guess, you forgot your homework?”

He smirks. “How didja know?”

“You have a bad habit of ‘forgetting’ it every day you deign to show up.” Strategically placing your purse on his desk, you shuffle through a folder labeled MATH in crazy curly type handwriting and hand him your finish homework.  You find it remarkable how fast he can copy your notes without leaving chicken scratch in his wake. It’s the kind of ability that comes from years of experience in cheating off other students. Not that you were one to judge. Your whole middle school social life was anchored around those who would let you copy their homework. It was only fair you pay you debt to society.

He finishes in record speed and you half expect him to walk out like he’s done so many times in the past that it doesn’t occur to you that you’re staring.

“See somethin’ you like?”

Your eyes widen, slightly embarrassed of being caught, but to answer his question, yeah. Your lips part ever so slightly when you tilt your head a calculated degree. “Did you always that silver earring?” Extending your hand towards the metal jewel, the pads of your fingertips marking their path with goosebumps as they brush against his cheek and neck.

He almost wants to lean into your touch. He almost does, but you pull away too quickly at the sound of heavy footsteps entering the classroom. The telltale steps settles down the class noise signaling that class will begin shortly.

Your teacher, Mr. Allen, opens class with a vague threat about his cheating policies, though he doesn’t mention any names, Henry catches an intended glare behind the rim of his glasses directed at the two of you. He can only assume you see it too as you slouch in your sit, making yourself as small as possible. It doesn’t stop him from handing in his plagiarism, practically daring Mr. Allen to do something about it.

And he does.

The next day you find yourself in detention, accompanied by seven other students, three of them belonging to the Bowers gang, the leader himself included. You take a seat next towards the window, a good two rows away from where the boys sat.

Whispers, too low to be registered by the supervising staff’s hearing aids, come from the gang’s vicinity as Henry laments his girl problems with the only two people that have been by his side from the beginning. Unfortunately, it was very much a blind leading the blind scenario since not a single one of them have had an actual relationship with a girl since elementary.

While your ear drums were far superior to that of your authority, you still can’t quite make out what their saying and though you don’t fault Henry for getting you in this mess, you knew the risks, it irks you that he gets a social club and you’re stuck bored for an hour. Pondering what to do, you find satisfaction in making a paper football with the words ‘whatcha doin’?’ scribbled on the front. You flick it, shielding a soft giggle behind your hand when it bounces off Henry’s head.

Eyebrows raise and he glances back at you, the sun casting a halo glow over your body so much so it hurts to look at you directly. Reading over the note, he writes back on loose leaf notebook paper, crumpling it up and tossing it back at you.

None of your business

Can I make it my business?

No

Must be some real embarrassing shit

You watch him struggle with his reply; Belch and Victor tussling over the paper with him in a vain attempt to ‘help’ him with a witty come back. It was only a joke but with each passing second it becomes clear that you’ve hit a nerve.

When you receive his note you’re convince they’re joking. Flustered but convince. There was an attempt to scratch out the words FUCK YOU written in his handwriting, not that it surprised you, Henry was never much of a wordsmith. Underneath it however was a more blockish handwriting , one you’ve never seen before.

Wanna go out?

There were two boxes beneath it, one labeled YES and the other FUCK YES. You look over to see Belch and Victor snickering  and pointing with both their hands at their fearless leader who was now nose to the desk and arm curled tightly around his face flushed red from anger and embarrassment. You answer back with a box of your own.

Only if you pay

Deal

Henry doesn’t talk much on your date. Whether because of nerves or lack of interest you can’t tell, but he nods at all the right moments in your stories, asking follow up questions that are never too in-depth but prods you to keep the conversation alive.

He takes you to a movie theater that—of no surprise to you, his friends also happen to be at. Belch hands you and Henry tickets he already bought. The quizzically look you gave Belch was enough for Henry to answer on the teen’s behalf, “Don’t worry, he has a job.” His hand moves to the small of your back and guides you into the theater, not allowing you time to overthink it.

The two of you share a large popcorn, Victor having the ingenious idea for Henry to use that as an excuse for you two to touch like in those cliché romantic movies. Not counting on Henry to be so engrossed with the movie he doesn’t even try to make a pass at you. During the second lull in the film, he stretches his arms above his head and you take it as a signal, leaning in ready for the classic sneak-an-arm-around-the-date maneuver, only to feel like an idiot when his arms come back down, crossing over his chest.

This motherfucker.

There was a murder in that theater that day. Your confidence had been shot and Henry Bowers was the culprit to pull the trigger. Not once has he tried anything on you. No cat calls or suggestive remarks or a forceful kiss against your consent—Not that you wanted that but—. You know what he’s like, you’ve seen him at school, on the streets, shouting lewd comments at other women. You know for a fact that he ate out Beverly Marsh in public behind an alleyway the first time they talked. So what’s wrong with you? Where you not pretty enough or was your gut right the first time and all of this was just a horrible joke that’s been taken one step too far?

For the rest of the date you mourn over the blow; talking softer, becoming more aloof and over all distant. And Henry, being the man he is, doesn’t pick up on any of it.

To be fair, he was facing down his own demons. His mind kept drifting off to that moment in class, when you so boldly reached out to touch him. You had only grazed him but he always figured your hands were soft. No amount of moisturizer could ever turn his farm labored hands into what yours were and he was constantly reminded that late at nights under the privy of his sheets.

It takes an astounding amount of self control not to get a hard on just standing next to you, the way you sway your hips or how your low-cut dress exposed the curves of your cleavage. He wanted so badly to fuck you in the alley between the theater and Aladdin’s but you weren’t like the other girls he’s been with. And not in that pseudo better than other girls bullshit way. He’s sure if he actually took the time to know those one time flings and whores he’d find you shared similar traits with all of them. In some bizarre way maybe that’s what attracted him to you, that you were a collection of traits and personalities that made his heart skip a beat with a simple smile.

“Well… this is my house.” You crack a half smile.

“Uh, yeah.”

“I had a good time, we should do it again sometime.”

“Yeah.”

There is a beat of silence, giving him plenty time to make a move on you.

Nothing.

He looks at you with a weird look on his face. Like he isn’t sure how these dates are supposed to end. Did he expect you to invite him in while your parents were staring from the windows?

“Ok…”  You swallow down you pride and fear and anything else holding you back and using his arm as a balance, place a soft kiss on Henry’s cheek. Then you make a dash for the door, face flush and burning up, you can feel a mist of sweat cover your forehead, yelling out in a broken pitch “Bye!”

The kiss, no matter how chaste, was enough to push him over the edge. A bulge swelling in his pants on the way back home, pressing against the seams, and he reaches down to adjust himself in his jeans. He knew it. Even your lips were soft. Henry could only imagine what other parts of you felt like.

Next time, he thinks. Next time he won’t have to imagine, he’ll know.

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1. Henry Bowers Imagine

this is my first imagine ever on tumblr! I hope you guys enjoy! My twitter is @lilthachtyy ! word count: 1387 ••• I stood in the hallway with Richie, Eddie and Bill talking about a science project we were assigned. "You g-guys wanna come to my h-house after school? " Bill asked because we had to create an experiment with directions and all that scientific bullshit. We all nodded. "Yo where's your girlfriend Bill?" Eddie teased shoving him and Bill shot him a dirty look. They never told me this type of stuff. "Who's his girlfriend? Beverly? " I asked with a smirk. "S-shut up Y/n." He said, his face turning bright red. I laughed then glanced down the hallway to see Henry Bowers, Vic, Belch, and Patrick walking down the hallway, picking on kids as the passed. Patrick made eye contact and whispered something to Belch and started coming our way. "Ew what the fuck do they want?" Richie asked rolling his eyes. "Maybe we should just pretend they're not there?" Eddie tried to reason and we all shot him a look. "That is one of the worst ideas I have ever heard from you. Yeah we pretend they're not there? Then they beat the shit out of us." Richie said with an attitude, like always. I let out a chuckle and Eddie flipped off Richie in the process. Then Billy got shoved into the lockers, very harshly may I add, by Patrick. "Hey loser." Patrick laughed as Billy picked up all the books he dropped. "Look who it is, the nastiest who from Whoville. I loved you in the Grinch!" I teased Patrick based on his appearance. I heard Richie and Eddie stifle a laugh. (a/n I really think Patrick does look like he's from a dr. Seuss movie ok next ) "Shut the fuck up slut." Patrick said looking down on me. He was pushed right up against me. Henry was staring at me with a blank expression on his face. Henry typically was the one to pick on me and all my friends but for some reason he was all quiet today. I cringed at the feeling of Patrick leaning up against me. "Back off , you perv." I said using all my strength to shove him off of me, which he stumbled into Henry. "Who the fuck does this bitch think she is? I do whatever the fuck I want, when I want, with who I want." Patrick said to his friends, including Henry who stood there staring at me. "Want me to fuck her up?" Victor asked with a smirk. My friends stood paralyzed with fear. Eddie took out his inhaler and started using it vigorously. "Nah, Bowers I'm letting you do this one. You seem pretty sad maybe this will cheer you up." Patrick said patting his friend Henry on the back. I gulped as Henry began walking toward me.

"Fuck off Henry. Don't fucking touch me." I said as he came closer. He still didn't say anything. He grabbed my waist and shoved me against the locker. He looked super hesitant and was doing this all very slow. He raised his fist and went to punch me but then Richie , Eddie, and Bill threw their books at his head. "Oh now you wanna fucking do something? I'll beat your asses." Henry threatened chasing after my best friends as they sprinted down the hall. I gotta make sure I thank them later for that. "Damn, what was taking him so long? I'll just do the job myself." Patrick paused before raising his fist and punching me in the eye. My head throbbed as it fell back against the locker. I had never been in so much pain. "Lemme jump in." Belch said as he kicked me in the stomach, adding a punch to my nose. I put my hand over my nose and looked down to see my hand covered in blood. "Our work is done here, let's go find Henry." Patrick said leading his friends away. I felt a tear escape my eye, I didn't even realize I was crying. I had never been in so much pain before. Wishing Eddie was here to clean me up and tell me it was going to be okay, were the only thoughts going through my mind. Unfortunately he or any of my friends were no where to be found. I felt like I was gonna pass out, so I closed my eyes hoping someone would find me soon. I had little strength to even get up from the floor so I just sat there. Hoping someone would stumble across me , school had ended 20 minutes ago so basically no one was still here. "You look terrible." A voice said from above me. I pried open my eyes to see Henry standing above me. "Please don't hurt me." I said covering my face, hoping I wouldn't get punched again. "I'm not gonna touch you. What happened?" He said sitting next to me. I had never had a real conversation with him, the only ones I ever had consisted of insults and curses. "Your prick friends beat me up, Patrick did the most damage." I truthfully said as I wiped blood off of my nose. "Yeah you look like the shit was beat out of you." He said in his normal asshole voice. "Wow, you're so observant. If you're here to insult me or throw me in the dumpster behind school, can you just get to it? I'm sick of you wasting my time." I replied with a very snippy attitude. "Listen, I-I uh I wanted to tell you something." He began but I rolled my eyes. "What Henry? If this is that 'I totally feel bad about bullying you' bullshit I don't wanna fucking hear it. You're just trying to make me vulnerable just before you do something completely cruel." I was not taking any of his lies.

"No...that's not the case. I-I want to apologize for being such a dick. I know what I've done to you is pretty bad-" he began but I quickly cut him off. "Pretty bad? You and your friends fucking locked me in a locker for the whole school day, you broke the window to my room, you vandalized my locker with 'slut' and that's only just a few of the evil things you've done. Save your lies." I sharply responded. He sighed and stood up. Thinking he was leaving, I closed my eyes and sighed, leaning against the lockers to rest. But within seconds I felt him grab my waist and throw me over his shoulder. "Put me the fuck down." I whined while trying to pull myself out of his grip. "I'm taking you to the bathroom to clean you up." He stayed as he walked into the boys' bathroom with me and put me on the sink. He began cleaning up the blood off my face and I stared into his eyes. He was attractive. His messy blonde hair and his piercing eyes complimented him so nicely. I guess I had always had a slight crush on him, but it was masked by his nasty demeanor. I know, how could you like someone so scary? I asked myself the same question all the time. "Stop staring at me." He said with a smirk and I felt my face heat up. "Where the fuck am I supposed to look? You're literally standing right in front of m-" I complained but was quickly cut off with his lips on mine. I immediately kissed back, grabbing his hair. I felt him stand in between my legs and put his hands on my waist. I felt his hands start to go up my shirt when the bathroom door opened. "WHAT THE FUCK!?" Richie screamed, his eyes wide with Billy and Eddie mimicking his actions. "Uhhh I-..." I stuttered for an explanation but I quickly hopped of the sink. "Are you okay? Why were you kissing him? that's disgusting." Eddie said making a grossed  out face but looked at me with concern. "Yeah what Y/n. E-explain." Bill said crossing his arms and giving me a confused look. I sighed and pushed the three of them out of the bathroom, ready to explain what happened. Before leaving I glanced over my shoulder and looked at Henry. He sent me a wink and I quickly turned around, blushing like crazy. What the fuck did I just do?

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A Little Less Worse

Henry Bowers x reader

This fuckin’ sucks.

That’s all you could manage to think as you walked up to Derry High School.

This town sucks, this dinky little school sucks… That guy over there with the mullet looks like he really sucks. What the hell is he even doing?

You decided to get a little closer to take a better look.

“We know you’re sexually frustrated, Bowers, but that doesn’t mean you should take it out on us,” a small boy with a fanny pack all but screamed as the mullet boy pushed another kid with glasses onto the ground, earning an eruption of laughter from the three other guys.

“Hey, he kinda looks like a girl… An ugly girl,” the kid with glasses pointed at the lanky guy with dark, shoulder length hair, “Why don’t you go blow him and leave me the fuck alone?” The kid stood up bravely, but you could tell he was terrified of what mullet over there was gonna do to him for mouthing off.

He had a disgusting smirk on as he approached the boy and suddenly, you found you couldn’t fucking stand this guy.

“Hey, mullet!” You called out, causing him and everyone else in the near vicinity to stop whatever they were doing and stare at you. Everyone had a look of horror plastered on their faces as you took a few more steps forward. That is, except mullet guy and his friends. “They’re just kids,” you pointed out, motioning to the two boys he was about to beat the shit out of, “If you need a thrill, why don’t you take glasses’ advice.”

If everyone around wasn’t terrified for you already, they were now. No one had ever stood up to the Bowers Gang like that before.

“Ah, the new girl,” He smirked, walking closer to you, “I’m Henry. What’s your name, sweetheart?” His tone was sickeningly smooth, seasoned with the gross laughter of his dumbass friends behind him. You just glared at him with a raised brow, not being able to take him seriously.

“And why do you think I care what the fuck your name is,” you asked rhetorically. His smirk somehow got worse.

“Thought you’d wanna know whose name you’d be screaming later-“

HOLY FUCKING SHIT.”

The kid with glasses looked like he had just won the lottery as soon as the back of your hand landed on Henry’s cheek. You just smiled to yourself and walked to class.

As soon as you got to the classroom, you took a seat in the far back corner. No way in hell the teacher was gonna make you introduce yourself as the new kid in front of the whole class as far as you were concerned. You kept your gaze focused on the door, analyzing everyone that entered the classroom. They all looked relatively normal and uninteresting. Well, until Henry walked in.

This fuckin’ sucks.

You tried to look away as fast as possible, but he was one step ahead. His eyes locked on to you like a gun aiming for a target; which was exactly how he saw you.

“You gotta be fucking kidding me,” you said loud enough for him to hear as he took the open seat to your right, “What the fuck do you want, mullet?”

“To finish what you started,” he was smug and you hated it, “You left me real turned on out there-“

“I’ll slap you again,” you spat without hesitation.

“Only if it’s in bed,” he countered, giving you a wink.

“I’ll smother you with a pillow,” you retorted, getting more and more irritated

“Only if it’s with those pillows,” Henry wiggled his eyebrows as he glanced down at your chest.

“Oh my fucking god, I’m going to kill you,” he could hear the venom in your words, which just made him want more.

“Talking dirty to me at school?” Henry was enjoying every second of this, “Save some excitement for the bedroom, would ya?”

You had become so annoyed at this point that, without even thinking, you grabbed his shirt angrily and pulled him towards you. As much as you hated admitting it, the way he countered everything you said without that smirk faltering kinda turned you on as well. “Listen here, you motherfu-“

“Hands to yourself, please, miss (y/l/n),” the teacher walked into the room, already looking forward to the end of the year, “I know teen hormones ‘fly free’ over the summer, but you’re going to have to keep it to yourself in class.”

At that point, you calmly took your hands off Henry and straightened yourself in your seat, your eyes burning holes into the chalk board. You didn’t dare look at Henry after that. You could only imagine how much bigger the smirk was now. How he would be eyeing you, his expressions satisfied in all the right ways. Man, just thinking about it made your cheeks hot, which he was obviously was taking pleasure in.

“So… Miss (y/l/n)…” Henry leaned over, whispering slyly in your ear, “What time you wanna come over?”

“Gonna have to try harder than that,” you let yourself glance over at him, offering a small smirk, “Bowers.”

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I kind of like you too.. | Eddie X Reader

Request:can you do one where the reader is older than Eddie Kaspbrak? But she really likes him and the bullies make fun of her for it but he likes her too? Author’s note: older!reader ( just by one year tho). Hope you’ll like ittt @tomhollandsboo 💓

Y/N always thought that her crush would be a cute boy with messy hair from her year, or even one above, so when her heart started to beat faster whenever Eddie Kaspbrak was around she knew she messed up. Of course, Eddie was only one year younger than her, and there wasn’t even a height difference so you would guess Y/N was older. It still scared her, and the thought of Eddie not liking her was the first that popped into her head. Of course, they hanged out, talked a lot , and they were best friends but she was pretty sure he saw her as an older sister. And let’s not forget the age gap, that made things a little awkward. She thought it was a weird thing, and never told anyone except one person— her best friend. She trusted her best friend with everything, so she considered her crush on Eddie wouldn’t be a big think. Boy, she was wrong. Y/N and Y/F/N weren’t the most popular persons in their year. The Bowers Gang usually made fun of them, sometimes even bullying them when the Losers weren’t around, so when Y/F/N found an opportunity they took it. Offering information, or just making fun of the kids Henry Bowers did got you some sort of immunity. He would leave you alone, and even “befriend” you, so one day after Y/N told Y/F/N about her big secret , they went to Henry and ratted it all out. The Bowers Gang found it very amusing, thanked your friend and told her it was a good thing that they came to them. And that’s when the bullying started. Y/N walked down the hall and stopped at her locker, which was near her best friend’s. She looked at the locker and gasped. With red paint, there was written the word Freak. Henry usually just pushed her or made fun of her, but he never did things as this. Quickly, she tried to wipe the ugly word on her locker before more people started staring. Funny thing that she noticed was that Y/F/N wasn’t there. “ Maybe they didn’t come to school today.” She said to herself, hoping that what was written on the locker didn’t have to do with her crush on Kaspbrak. She could only hope. The classes finished faster than Y/N thought, and nor the Bowers Gang or Y/F/N showed up today, or bothered her. She found that weird, but let it slide and enjoyed the last day of school, or her first day of summer Holliday. As she walked into the schoolyard, she saw none other than Henry Bowers and her best friend laughing at and mocking Richie Tozier. Her fists clenched and her eyes narrowed. Of course. Y/F/N was too tired of being made fun of and not being popular , so she decided to throw Y/N aside, their only best friend, and be Bowers’ bitch. Y/N quickly found her way to where her ex friend was standing. “ How fucking dare you?” She screamed at them. “ my , my , my. If it’s isn’t the freak, am I right Y/F/N?” Bowers smirked and looked at the buffoons that stood beside him, and dropped Richie to the ground. “ that’s right “ they smiled at Henry. “ it’s the one and only pedo in this school. You know, my little brother would be interested in you, he’s what? Five?” they laughed mockingly at her. Henry and the others laughed, and he continued to walk towards her. “ Think you look so brave, standing up to me for these Losers, hm? Or maybe you just want a certain Kaspbrak to give you attention?” he smirked looking at Eddie and then at Y/N.

Y/N didn’t even dare to look back at Eddie or the rest of the Losers. She was ashamed, betrayed and hurt. Her best friend, the person she trusted since she was five , the first person to be her friend, the first one who found out about her crushes or about anything important in her life was now staying beside Bowers and laughing at her. And what was worse is that Eddie knew about her crush on him. Oh fuck he knew. “ Cat got you tongue,huh? Well since you like Eds here maybe you liked little Georgie Denbrough too, right? I saw you smiling and helping him with school. Maybe he was your boyfriend, right? You still grieving him?” he smirked. Y/N was as angry as ever. She didn’t even care about Eddie anymore. How dare he talk like that. Within a matter of seconds, she slapped Henry with all the force she had. “ You are the only fucking pervert here, Bowers. Don’t you dare talk about Georgie again! And you , Y/F/N, you’re his bitch now. Congrats!” She said, then running away from the Bowers Gang as fast as she could, going into the woods at her secret place , where they couldn’t find her and where she would cry. She lost two friends today— Y/F/N and most probably Eddie. After a good half an hour she heard footsteps near her. She knew this was the end. The Bowers Gang found her and they were going to either beat her to death, or torture her and then kill her. She prepared for Henry’s face to pop out in front of her, but instead of that he heard a voice. “ Y/N? Are you here? Come on! I know this is your secret spot.” Eddie’s voice echoed into the woods. “ go away Kaspbrak.” She said, her voice breaking. “ oh god, have you been crying? Come out Y/N. So we can talk.” he pleaded. Finally, she came out of her hiding place, finding a worried Eddie? “ Do you want to tell me something or..?” She said, her shoes suddenly becoming interesting. “ yeah. Slapping Bowers in the face was pretty cool” he laughed. “ that and I kind of like you too and I don’t think you’re a freak.” He said with a blush on his face. “ wait, are you kidding me? Because if you are…” she started. “ I’m not! I’m not why would I? “ he said looking at her and smiling. Y/N smiled back and hugged him tight. “ Thanks Eddie. For everything. “ “ Why thank me? You saved our asses today and you slapped Henry in the face. My girlfriend is a badass.” “ your girlfriend?” she smirked, arching a brow. “ I, I… I mean not my girlfriend, I..” he stuttered, avoiding her gaze. “ I would love to be you girlfriend.” She smiled and kissed him on the cheek, leaving him a blushing mess.

This so soooo cute

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Tom at the baby driver premiere just gave me a baby

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