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Pennywise x (Facepainter) Reader

  I painted a kid's face at this local fundraiser the school was having. They needed volunteers to raise money and so I volunteered.  Once I was done painting his face to look like a clown the little boy thanked me then ran off.

"He is quite happy with his new face, isn't he?" A voice spoke from behind me.

I turned my head to look at who was talking, my eyes met someone's chest so I had to look up to meet their eyes. It was a much taller man dressed as a clown.

"Yes, quite so," I smiled, "Though He'll probably smear it or get it on his clothes."

"That's for sure," He extended his hand out for a shake, a Cheshire Cat grin spreading on his painted face, "I am Pennywise the Dancing Clown!"

"Y/N. nice to meet you, Penny."

I assumed he was one of the performers walking around. We had some stilt-walkers roaming about taking pictures with people. I hadn't seen any clowns yet, him being the first one I had ever seen during this fundraiser. This Penny guy really went all out. Was he wearing small stilts? He was unusually tall. It had to be stilts or something.

"Y/N, would you like to join the circus?" He beamed With a wide smile, "You could help paint children's faces!"

"Join the circus?" I lightly chuckled at the idea as another kid approached me to get her face painted, while I painted her face I continued speaking to Penny, "I've never thought of doing that, I don't think I'd make a lot of money."

He leaned down to me, "It can be a great adventure, Y/N. Besides, what is more important? Money or experience?"

"Right now in my life?" I asked, "Money."

He held my gaze, "That is a good point. And yet...How many people can say they have worked in a circus?"

"You make a good point," I said as I dabbled my brush in more paint to make a lion on the kid's face.

"That's right, Y/N," he towered over me, "Follow your dreams and don't let anything hold you back. Do you know what my dream was?"

"First off, back up, buddy," I held my hand in front of him, lightly pushing him away by his chest, "Second, what was your dream?"

"My dream was to be..." he slowly approached me again. He was still smiling broadly, but a sinister gleam filled his eyes. He grabbed me by the shoulders and stared deep into my eyes, "The clown that everyone fears."

"Good for you, buddy," I shook his hands off my shoulders, "Though I think you're not scaring anyone—"

I was cut off by a certain voice. Henry Bowers. He approached me with his little gang of bullies trailing behind him. There was a hint of worry that he would come looking for me during this event. I had humiliated him a while ago and he held a tough grudge against me.

"Hey, bitch," He sneered, "Painting little kids faces? What? Have nothing better to do?"

Penny was unfazed. Henry Bowers was not the first bully he had ever met and will most likely not be the last.

"Oh, Henry. What a surprise to see you at a charity event," I said with a mocking tone. I turned my gaze to the little kid I had been painting, "Why don't you go play with your friends now, bud? This is not something you're gonna want to see."

The kid ran away quickly to his parents and left. Henry Bowers glaring daggers at me. He intended on beating me up, but first he had to get me away from the charity event.

"How about you come with us, Y/N?" Henry grinned.

"They're lying~" Penny spoke near my ear.

"I know," I said.

"You know what?" Henry asked.

"I wasn't talking to you."

"Then who the hell were you talking to?"

I turned my head to Penny who simply smiled at me with a deadly look.

"They can't see me!" Penny told me in a sing-song voice.

"Ah," I nodded before focusing on Bowers, "Can we do this some other day?"

"Nah, I'm bored," Bowers walked up to me and was about to throw a punch before his fist was caught mid air. Penny grabbed his fist and twisted his arm.

Bowers shrieked and his gang backed away in confusion and fear. Bowers could now see Penny who made himself known to the screaming brunette. I looked away as he screamed in agony, a quick snap and his wrist was then broken.

Something picked me up and before I knew it, I was on top of the school building. The roof to be exact. Penny had somehow gotten us here in the blink of an eye. He set me down in front of him, Penny sitting crisscross.

"How did you—?"

"Knowing everything is not always a good thing," Penny cooed as he placed down a bunch of items to the side of him.

It was my facepainting supplies. He pulled me closer to him, knees practically touching, as he took a wide paintbrush and dabbed it in white paint.

"What are you doing?" I tilted my head, confused.

"Painting you, silly~"

"Well, I figured that," I shook my head in amusement, "I mean why are we up here?"

"So no one can bother us."

He placed his hand on the side of my face, bringing it down to hold my jaw in place so he could paint easier. Penny was probably making my face look like his.

"Hold still," he said as he focused, "We'll be done in no time..."