#newsies headcanon

Requested:  date with Bill and Darcy HC?

Warnings: none

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Bill

• You were child hood friends
• It surprised you along with everyone else when he asked you on a date
• You hadn’t expected it 
• But that didn’t mean you were complaining
• Katherine helped you with your outfit
• Both of you spending almost all day getting you ready
• Bill would have loved you dressed in anything
• But what Katherine had whipped up had the boy at a loss for words
• He found out your favorite restaurant from Katherine
• Surprising you once you’d arrived
• Even though you had tried to deny it multiple times, Bill insisted on paying got the bill
• Bill paying for the bill haha
• You both shared a dessert
• Smiling when your spoons would accidentally hit the others
• You were a blushing mess the entire walk home
• Your hands swinging between the two of you
• Bill wanted to take things slow
• Leaving you with a small kiss on the cheek to last you until you’d see him again

Darcy

• Darcy shows up as an anxious mess
• Most of the boys lecture him while you’re still getting cleaned up
• He’d brought flowers for you, and he couldn’t help but perk up when he saw you
• You’d thanked him for the flowers, putting them on your bed before you both walked hand in hand down the streets
• Darcy originally planned to take you to a fancy little place
• That had been until you explained it didn’t interest you
• But really you’d been slightly embarrassed about not having anything nice to wear
• You didn’t want to go and stick out like a sore thumb
• He took you to a little bakery
• Knowing you liked one of the pastries to death
• You’d frequently saved up for a while so you could get it on special occasions
• You couldn’t hide your excitement when Darcy brought it up once you declined his fancy date
• Both of you got your own drinks and different pastries
• You shared, going half with each other so you could try something new
• Your first kiss was on the front steps of the lodging house
• The boys cheered and whistled behind you but neither of you took notice

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Tag List: 

@mathletemadison@hats-or-badges  @theatrequeer  @snakeyboimusical  @mariah-vg @briefexpertgladiator  @the-moon-looks-old-and-gray  @neko-kaiyo

Requested: Modern time (if that’s okay) and African American! Shy!Reader… Morris is noticing kids in your grade is bullying you because of the color of your skin and how quiet you were…that All I got,let you mind go from there

Warnings: bullying

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• You never really spoke to anyone at school
• But that didn’t mean that people never noticed you
• You knew it was true for the girls that had always picked on you
• They made sure to torment you everyday
• You had been the only African American student at your school
• You never stood up for yourself
• You didn’t know how
• Morris saw it everyday
• He’d almost been waiting for you to say something back
• It hadn’t been until he saw you sitting by yourself and crying one day after school that he’d realized you never really had stuck up for yourself
• He’d sat down next to you and started to talk
• You hadn’t responded at first
• Wiping your eyes of your tears until he’d said it was okay to cry
• Morris hadn’t expected the meek little voice that had come out of you once you’d finally started talking
• You both started hanging out everyday after that
• Both of you getting closer and closer by the day
• You hadn’t asked him to, but he stood up to those girls for you
• It wasn’t long until you started dating
• You didn’t want anyone knowing at first
• You’d been worried about things people would say
• Especially if people started to say things to Morris
• You wouldn’t have been able to live with yourself if you’d been the reason he was being treated poorly too
• It hadn’t been as bad as you expected
• There were a few comments from people
• But over all everyone had left you both alone when they’d finally gotten to know you
• And that’s all you had wanted ever since you’d started going to school there

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Tag List: 
@mathletemadison@hats-or-badges  @theatrequeer  @snakeyboimusical@mariah-vg @briefexpertgladiator  @the-moon-looks-old-and-gray  @neko-kaiyo @fuck-your-fandoms

Warnings: none

Summary: What they do for you on your anniversary

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Jack Kelly: Paints a portrait of you

Davey Jacobs: Definitely the type to propose 

Crutchie Morris: Takes you on a small vacation

Racetrack Higgins: Mini golf date

Spot Conlon: He takes you to the beach for the whole day

Albert DaSilva: Amusement park date

Finch Cortez: Bakes for you

JoJo De La Guerra: Makes you a nice little video

Darcy: Gets you flowers and chocolates

Bill: Gives you a promise ring

Katherine Plumber: Takes you to a fancy restaurant

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Tag List: 

@mathletemadison@hats-or-badges@theatrequeer@snakeyboimusical@mariah-vg@briefexpertgladiator@the-moon-looks-old-and-gray@neko-kaiyo @werkwerkelizaaa@wiffle-snuffles

Drive In - TommyboyxRomeo Headcanon

Requested: *cough cough* Tommy boy x Romeo date request? Please?

Warning: none? Maybe implied homophobia?

Summary: Tommy boy and Romeo’s drive in date

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• Tommy boy’s hands were sweaty while he waited for his boyfriend to come out of his house
• He would have held the door open for Romeo, but he knew he couldn’t
• They both figured out where they could have a date out in public
• They may be in the car the whole time, but many people went to the drive in as a date
• They sneakily held hands the whole way there
• Only letting go when Tommy boy had to pay for their ticket
• It was all fair game once they were in
• They had put up shirts and blankets to cover the windows
• No one would have bothered to look in the car, but they didn’t want to take any chances
• They had enjoyed the movie silently for the first half
• Their hands permanently attached
• Kisses were shared every few seconds while the movie continued to play
• It changed from quick pecks to long passionate kisses
• Tommy boy’s hand cupped Romeo’s face and pulled him closer
• It filled the two with joy to finally be able to kiss each other without fear of someone walking in and seeing them
• It was almost like a spike in their adrenalin that made the experience a whole lot better
• The movie playing in front of them had been pushed to the back of their minds
• The world surrounding them disappeared
•  It was only the two of them 
• No one else existed and they were the last two people on earth

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Tag List:

@hats-or-badges @theatrequeer @snakeyboimusical @mariah-vg @mathletemadison @briefexpertgladiator @the-moon-looks-old-and-gray @neko-kaiyo 

Warnings:  smut, first time

Summary: your first time with the boys

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Racetrack Higgins & Albert DaSilva

• Why both of them together? Threesome bitches
• It’s not any of your first times
• But it’s your first time together
• Let’s just say these boys leave you SATISFIED

JoJo De La Guerra

• Poster boy for the word wholesome
• Asks how you feel every five seconds
• It’s a bit adorable if you’re being honest
• Despite the constant check ins, he gets the job done

Buttons

• He handles your nerves like a pro
• Knows exactly what you need
• Like JoJo checks on you a countless amount of times
• CEO of aftercare

Specs

• This boy knows what he’s doing
• It’s like your toes are permanently curled the whole time he touches you
• The sheets are almost pulled off the side of the bed when he’s done
• You’d almost forgotten you’d been nervous before hand

Tommyboy

• He’s so shy but tries to act like he knows what he’s doing
• You can tell, but you let him think he’s doing everything like a pro
• But he’s not bad for it being his first time
• You both end up switching positions and the inexperienced comes out in him

Bill

• Thought it’d be wholesome didn’t you? Well its rough or as rough as a first time can be
• It’s very lovey dovey but also verrrrrry passionate
• You can’t even walk the next day
• But it’s worth it to you

Darcy 

• Your first time is very wholesome
• I’m talking candlelit room
• Darcy is very very gently with you 
• You had nothing to compare him to, but you could only assume that was the best sex you’d ever get

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Tag List: 

@the-moon-looks-old-and-gray@mathletemadison

Warnings: smut, oral

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• Jack and Spot always tried hiding their relationship with one another
• The only time they’d ever get alone time together was at night
• Jack always sneaking over, meeting Spot under the bridge
• This day in particular it seemed that both boys were filled with frustration
• It quickly turned into a fight for dominance between the two
• Even with Spot being shorter than the Manhattan leader he got Jack beat
• Jack immediately melted and gave in the second Spot’s lips touched his 
• The kiss quickly became heated when Jack ran his fingers through Spot’s hair
• Pulling him in closer, both of their tongues exploring the other’s mouth
• Spot seemed unable to hold back 
• His throbbing length aching for relief
• He grabbed a fist full of Jack’s hair
• Pushing him down to his knees while his free hand undid his pants
• Spot hardly gave Jack anytime to part his lips before his pushed his length all the way in
• Feeling Jack gag around him only made Spot groan
• His hips started to buck quickly
• Jack’s continuous gagging seemed to only make Spot go quicker
• Spot’s head was thrown back, moans and profanities slipping through his parted lips
• Jack couldn’t help but moan at how rough Spot was being with him
• There was no doubt his jaw would be sore the following morning
• But Jack couldn’t stop himself from cumming even though he hadn’t been touched
• He whimpered around Spot’s length only sending him over the edge seconds later
• To say the least the next day all the newsies were confused over Jack continuously rubbing his jaw 
• And there was no mistaking the stain that had stayed in his pants

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Tag List: Let me know if you want to be added to the list :)

@mathletemadison@the-moon-looks-old-and-gray@theatrequeer@snakeyboimusical@mariah-vg@briefexpertgladiator@neko-kaiyo

Requested: you dont have to do this but its lgbt so i hope you do. hcs of Oscar (Delancey ofc) slowly getting a crush on a guy but he has internalized homophobia??? i hope that makes sense ♡

Warnings: internalized homophobia, homophobia, mentions of bullying and fighting

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• You were new to being a newsie
• Your parents kicking you out the second they’d found out you were gay
• When you showed up to the circulation the next day Oscar’s breath seemed to catch in his throat
• He always tried ignoring this feeling but something about you made those feeling stay on his mind all day
• It didn’t take long for everyone to realize Oscar was treating you a whole lot nicer than everyone else
• As soon as it was brought to his attention he seemed to completely change
• You turned into the most picked on newsie of the entire lodging house
• It hadn’t been until a week later that you found out why
• Walking back from a long day of selling you found yourself pinned up against the wall in the alley
• You weren’t surprised to see it was Oscar but your heart started to beat out of your chest nonetheless
• You’d never been this close before and you were sure Oscar was finally going to lay a hand on you
• The entire alley was silent
• Nothing but the sound of people walking by filling your ears
• Oscar didn’t say anything 
• Only staring at you with a look of confusion on his face before his lips met yours
• Your eyes almost popped out of your head
• But something about the passion that had been put into the kiss made you melt and kiss back
• The second you started to run your fingers through Oscar’s hair he pulled away quickly
• He gave a small smile before leaving you there
• This had continued on for weeks
• It confused you at first
  
• Until you realized Oscar was trying to hide who he was
• You couldn’t blame him
• All the times you were pinned up against a wall with both of you speaking quietly to one another made up for it
• A few times you almost forgot about your relationship with each other
• Forgetting that you understood why Oscar would always pick on you along with the other boys
• But one day it seemed to be different
• It seemed as though something pushed Oscar over the edge
• Fighting out in the open leaving you with a good shiner for weeks
• He tried making up for it the night you walked back to the lodging house
• Explaining his father’s suspicions of his late night adventures
• You hadn’t accepted it
• Wanting him to figure out what he truly wanted before ever coming near you again
• To everyone’s surprise a few weeks later Oscar visited the lodging house
• It seemed he figured out what he had wanted
• Kissing you in front of everybody
• Willing to be a newsie just to get you to believe him
• But you were too keen on having surprise visits in your favorite alley to ever allow Oscar to become a newsie

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Tag List: Let me know if you want to be added to the list :)

@mathletemadison@the-moon-looks-old-and-gray@theatrequeer@snakeyboimusical@mariah-vg@briefexpertgladiator@neko-kaiyo

Warnings: homophobia

Summary: Your senior year prom

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• Crutchie had the biggest crush on you ever since freshman year
• Now that it was senior year and prom was around the corner he finally decided to do something about it
• With Katherine and Davey in ASB Crutchie had the perfect plan with perfect connections
• It had been over a month long affair but everyone was sure to keep you out of the loop
• Crutchie was ready to ask you to go as friends until you were asked by someone else
• It had been a surprise to everyone when Oscar made a promposal just for you
• No one would’ve thought Oscar was gay
• Crutchie had his doubts, but everyone reassured it was probably his feelings for you getting in the way
• That was until Crutchie had delivered a note to the gym teacher and overheard something he shouldn’t have
• Oscar had been boasting to his friends about getting the gay kid to go with him to the prom
• They had all started planning any and every prank they could pull on you at the prom
• Crutchie tried to get out as fast as he could
• But being on a crutch he could only go so fast
• Oscar had pinned Crutchie up against the wall
• Swearing him to secrecy of everything he heard
• This only fueled Crutchie’s original plans for the prom even more
• By the night of prom Crutchie’s plan was in full swing
• Everything seemed normal until it was time for the queen and king to be announced
• To everyone’s surprise your name was called for prom queen
• You tried not to show that it bothered you
• Going up and getting the crown as if it was a normal thing to happen at the school
• You stood there and awkwardly accepted the crown
• The second the crown was placed on your head you were covered in glue and rainbow colored glitter
• Everyone was in a state of shock, and that’s when Crutchie came out
• On the spot he’d confessed his feelings for you
• Willing to stand in the gooey mess with you
• Explaining just how much he wish he got to you before Oscar did
• You were almost as shocked as everyone else in the crowd
• Confessing you wished he had been the one who asked you the whole time
• Crutchie pulled you in for a kiss, the glue and glitter starting to rub off on him
• The entire venue erupted in cheers

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Tag List: Let me know if you want to be added to the list :)

@mathletemadison@the-moon-looks-old-and-gray@theatrequeer@snakeyboimusical@mariah-vg@briefexpertgladiator@neko-kaiyo

Requested:  if it’s ok, could u maybe write a Katherine x Fem!Reader NSFW headcannon? Katherine is literally the best and I’m so gay for her it’s unreal lmao

Katherine x reader going lingerie shopping? I think them picking out lingerie would be cute. happy pride! ️‍

Warnings: smut, oral, sex toys

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• It started off innocent
• Katherine had invited you to go lingerie shopping with her
• It was the first friend date in a while and you couldn’t turn it down
• The whole way to the store you both sang loudly in the car
• You both decided to pick out everything for the other
• Both of you running around the stores trying to find anything
• Giggling like school girls when you would bump into each other
• Trying to hide what you were holding in your hand
• You couldn’t help but blush when you thought of Katherine wearing the things you were getting
• Little did you know so was she
• You kept your bags a secret until you’d gotten back to your apartment
• That was when the sexual tension started
• You had picked out a bright blue lacey set for Katherine
• It was hard to hide your blush that seemed to get deeper with each set
• It got even deeper once it was your turn
• Katherine deciding to stay in her favorite pick from you
• You felt her eyes burning into your back while you changed
• You shyly asked for help once you got to something you’d never seen
• There was no hiding the gasp that came from you when Katherine ran her fingers across your back
• Moving her arms around your front as her breath fanned your neck
• A small moan left you once she lightly pressed her lips against your neck
• She pulled you closer to her
• Making sure to mark you as hers before she let go
• When you turned around she immediately pulled you in for a kiss
• Pushing you up against the wall making you let out a whimper
• You already felt your knees going weak just from the kiss
• Your entire body feeling like jell-o when she started kissing down your neck and chest
• She gave a small wink before pulling down your underwear
• Teasing you with light kisses on your thighs
• Waiting until you were squirming against the wall to finally go where you needed her the most
• You would’ve fell to your knees if it wasn’t for Katherine holding you up
• Her tongue sent you to cloud nine
• Hitting all the right spots 
• Making you let out the most needy moans you ever had before
• Once she added her fingers you were done for
• Your body shook above her
• Your orgasm washing over you not long after
• When Katherine came back up for a kiss you were in a daze
• This was a shopping trip you would never forget

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Tag List: Let me know if you want to be added to the list :)
@mathletemadison@the-moon-looks-old-and-gray@theatrequeer@snakeyboimusical@mariah-vg@briefexpertgladiator@neko-kaiyo

Requested:  Modern time! Davey x bisexual!reader. What if the reader was Davey’s girlfriend and they go to a pride parade and Davey’s confused about the LGBT community so she tries to explain everything the best she can. And just fluff

Warnings: none?

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• You had to beg Davey to go to pride with you
• He wasn’t sure about going at first
• Asking why you wanted him to go if he was straight
• You explained how it was him showing his support
• You’d even gotten him wear matching makeup with you
• Davey had been a bit confused on the drive there
• But you made sure to fill him in
• You knew Davey wasn’t the crowd type
• But to your surprise once you were there he loved it
• Davey tried getting you anything and everything
• Even picking up a condom off the floor and winking at you
• You couldn’t help the blush on your face 
• Davey handed it to you so nonchalantly you couldn’t help it
• You bought both of you dick shaped ice popsicle as a joke
• But Davey ate it like it was an ordinary popsicle
• Being at the parade helped Davey a lot
• You tried answering all of his questions the best you could
• Being around so many different people was new for Davey
• But by the end of the parade it was different
• You were going home with a few flags
• Davey got a bunch of stickers
• Some bracelets
• And he’d even bought you both hats
• Begging Davey to go with you turned out to be a good idea

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Tag List: 
@mathletemadison@hats-or-badges@theatrequeer@snakeyboimusical@mariah-vg@briefexpertgladiator@the-moon-looks-old-and-gray@neko-kaiyo

Requested: Can you write gay Davey oneshot please

Warnings: internalized homophobia

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• Davey had known he was gay for as long as he could remember
• He hid who he was for the longest time
• Not knowing how his friends or family would react
• It wasn’t until he’d met you that he started feeling more comfortable with who he was
• Davey had seen how comfortable you were with your sexuality and he couldn’t help but admire you
• He fell for you and he fell hard
• There was no question about it
• Everyone around the both of you could see just how infatuated Davey was by you
• You were Davey’s first kiss, and it surprised you to say the least
• Davey had initiated it, and no one would have ever guessed he would have done that
• You couldn’t deny that you felt the same way about Davey 
• Your relationship with each other started not long after your first kiss
• Davey learned how to be comfortable with himself from you
• Finally seeing that him being different didn’t have to define who he was
• There were still times when Davey was a bit insecure
• But it was nothing a small kiss and some reassurance couldn’t fix
• Davey had some getting used to
• But you were his first after all

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Tag List:  @mathletemadison@hats-or-badges@theatrequeer@snakeyboimusical@mariah-vg@briefexpertgladiator@the-moon-looks-old-and-gray@neko-kaiyo

Requested:  hiii! i rlly love ur one shots, so i was wondering if u would do a Katherine x Fem!Reader? it’s oki if u can’t :)

Warnings: some smutty(ish) stuff 

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• You and Katherine always had an on and off relationship
• One minute you loved each other 
• The next you were trying to rip each others throats out
• None of the boys eve paid much attention to it
• Knowing you both would get over it soon enough
• It wasn’t uncommon for one of you to come to the lodging house a day after an argument with hickeys littering your necks
• You’d always find your way to your favorite alley
• One of you pinned against the brick wall while the other went to town
• Both of you tried to be stubborn and keep quiet
• But the arguments melted away once the first moan left either of your lips
• It had almost been a way of both of you giving in
• You couldn’t remember all the times it would take almost an hour just to get the smallest noise to come from either of you
• You couldn’t stop loving Katherine no matter how much you argued
• You couldn’t help but think that had been the only thing that kept you both together
• It wasn’t ever big arguments, only arguing about the smallest things
• It had seemed that any real problem you both had would actually be talked about
• On the other hand you remembered you’d argued about a sock left on Katherine’s floor
• There was no doubt that both of you loved each other to death
• No matter the reason for arguments, you both still slept peacefully in each other’s arms at night 

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Tag List:  @mathletemadison@hats-or-badges@theatrequeer@snakeyboimusical@mariah-vg@briefexpertgladiator@the-moon-looks-old-and-gray@neko-kaiyo

Jack Kelly: full blown bisexual

Davey Jacobs:bi-curious (once he met Jack haha)

Crutchie Morris:gay (I don’t make the rules :p)

Racetrack Higgins:trans guy (cause lots of people have this headcanon for some reason)

Albert DaSilva:ace/aro(just because of the headcanon I’ve written for him)

Spot Conlon:closeted gay (with tons of toxic masculinity)

JoJo De La Guerra:pansexual

Finch Cortez:queer (because I can’t think of anything else lol)

Romeo:drag queen (again, I don’t make the rules)

Bill Hearst:gay for Darcy

Darcy Reid:gay for Bill

Katherine Plumber:our lesbian queen

Les Jacobs:we support our questioning boy

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Tag List: 

@mathletemadison@hats-or-badges@theatrequeer@snakeyboimusical@mariah-vg@briefexpertgladiator@the-moon-looks-old-and-gray@neko-kaiyo