Alright. What was he going to wear? He was still a little unsure about this whole masquerade thing. There was a makeup booth, face paints, everything he needed for, like, a vampire. He could do vampire makeup and zombie makeup easy.
But the problem was, neither of those things were a *character*. That phrase had been emphasized all night. Simon was not very good at improv. Put him on the spot, and he’d be stumped.
He needed inspiration, he needed… a costume… something…
Simon’s eyes roved over the rest of the room.
Holy cow!
The room was full of Halloween paraphernalia. There were three more card tables set up with masks, but there was also a rack full of outfits one could change into. Simon easily spotted the literal monkey suit the wig went with.
This room had just about any disguise he could imagine.
There were some classic masks (including a werewolf mask that beat the pants off the old rubber Halloween mask Simon was on the fence about bringing), but there were also other face coverings. Simon spotted a few eye patches, and even a large bull-style nose ring. There were headbands with horns to go with it, and he swore there were some shoe boxes in the corner. The possibilities were a little overwhelming to be honest.
Choices choices choices…
Simon was pretty sure he didn’t want something that would obscure his entire face or be too cumbersome to wear the whole night. Maybe he should put the monkey suit on over his clothes? Ironically that outfit seemed to cover everything but one’s face.
He poked around a little bit more.
There was a table in the back that mostly seemed to have human masks? They could be fun if you were going for a spy movie reveal maybe? He didn’t seem to recognize any of the faces… No movie stars, no politicians, and only a few faces he’d describe as a “caricature”.
Tucked away on the edges of the furthest table, Simon could swear he saw another porcelain copy of Mister E’s mask.
Simon chuckled. He could get up to some real mischief with that. And it was porcelain, which meant it wouldn’t trigger his allergies.
But would it win him the prize? No. It might even get him kicked out.
A character… inspiration…
Simon’s eyes fell on something wedged in the farthest corner of the room.
A skateboard.
Simon's eyes widened. It had a worn, retro design, complete with neon colors and geometric shapes that screamed '90s style. The wheels of the skateboard were painted in vibrant neon colors.
A grin crept across his face as a spark of inspiration ignited within him. His character could be a persona that embodied the essence of the skateboard culture from the '90s, a time when rad tricks and baggy pants were the epitome of cool.
He approached the skateboard, a grin slowly forming on his face. This… this was his ticket to a memorable character for the masquerade! His mind raced with each step, a whir of possibilities.
Simon picked up the skateboard, feeling its worn grip tape beneath his fingers. As he picked it up, the wheels spun effortlessly, and he couldn't help but smile.
Okay, a skateboarding character. Cool.Now he needed to assemble an outfit.
He glanced around the room, looking for something that screamed ‘90’s’ cool.
Next to the skateboard, he noticed a pile of clothing. It was like a blast from the past: oversized, neon-colored T-shirts, baggy jeans that would have been on trend two decades ago, and a ballcap, the rim folded.
Simon grabbed the attire and quickly changed into it. The baggy jeans felt strangely comfortable, sagging down, revealing his boxers. He grabbed a bright pastel blue-colored shirt with abstract triangle patterns. It was like something straight out of a Saved by the Bell episode.
The baseball capo was purple and covered in tiny pepperoni pizzas. He put it on backwards. That was the epitome of cool in the 90’s.
As he finished putting on his clothes, his eyes landed on a simple pair of oversized glasses. They were quirky and nerdy, the frame chunky and lime-green. He let them rest on the top of his head so they wouldn’t be in the way.
Now, all that was left was the mask.
He glanced over at the rubber and latex masks but quickly realized that none of them would fit the character he was going for. Not to mention they’d trigger his allergies. He needed something unique, something that would tie his entire look together.
He sat down in front of the makeup booth and sighed.
What could he be that made sense for the ‘90’s vibe he was rocking? Dracula? Wolfman?
Simon paused. No, neither of those. It was cliche but not in a good way.
His eyes fell on the masks and then to a collar and leash hanging on the knob of the changing room door. The idea struck him like a bolt of lightning.
How about a dog? He was good with fur, and dogs were often cartoon characters in the 90’s. Maybe he could be a cool, skateboarding dog character!
With newfound enthusiasm, he made his way to the makeup shelf. Simon had been pretty good in art class, so the facepaint should look fairly realistic. Would it be enough to win?
He grabbed a tube of face paint, an assortment of various browns, some highlight colors, white, black and pink, and started to apply it generously. The face paint covered his cheeks and chin, creating the illusion of fur. He painted a black dog nose over his own, then finished his upper lip. Gave himself a few whiskers, and with a flourish, drew on a tongue lolling out the corner of his mouth to complete the look.
When he was finished, he examined himself in the mirror.
He looked like a walking embodiment of the '90s, with the skateboard slung over his shoulder, baggy jeans, pastel shirt, oversized glasses, and that tongue painted on his cheek. It was ridiculous, but it was perfect.
With a swagger in his step, he headed back to the main room. “Excuse me, Mr. E? I think I’m ready.”
“That’s Mister E-“ The masked figure’s head perked up as he spun around, “Oh! So you are! What an… eclectic choice.”
“I mostly just wanted something I wouldn’t need a straw to drink with,” Simon chuckled. “I’m pretty good with facepaint, too.”
“I… I’m not sure you’re as good as you think-” Mister E started to say, but Simon cut him off.
“Nah, don’t sweat it.” Simon preeened, rubbing his fingernails on his retro shirt and blowing on them. “I know it looks good. You don’t need to praise me.”
“I promise not to praise you.” Mister E leaned in a little closer, “So… Who are you?”
Simon blinked. He looked down at himself, then back up at the masked man, “I’m… a dog?”
“Uh huh…?” The figure nodded, “Does this dog have a name?”
Simon’s eyes lit up. “Oh! You mean a character!”
Mister E slapped a gloved hand onto his mask.
“Hoo boy…” the host murmured. “Now you’ve got *me* breaking character.”
“Sorry, umm… he’s cool… and a dog… Cooly Doggo? No, that’s dumb. Uh- Cool… no, Mr. Dog… uh…”
Mister E’s foot tapped on the floor. “My patience is waning.”
“Cool… Dog..” Simon shrugged giving up on it. “Cool Dog. I’m Cool Dog!”
Mister E stared at Simon. Sweat trickled down his back under the blank gaze.
“Okay. So. You are a persona of the ‘90’s. Cliched caricature, I presume?”
“Yes.”
“So… give me a few lines.”
“Uh… yeah, I’m Cool Dog, yo!” Simon did a weird little shuffle.
Mister E stared at Simon, somehow managing to be nonplussed even while wearing a blank mask.
“What was that?” Mister E asked.
“T-the Macarena?”
“That was *not* the Macarena. That was a seizure.”
”Then it was the, uh, the electric slide?” Simon said sheepishly.
“Perhaps you need some help getting into character?” Mister E asked.
“Uh, sure, got any pointers? I was a kid in the ‘90’s and-”
Mister E snapped his fingers.
As the sound hit his ears, Simon felt the world scrunch around him, his head feeling like it was being compressed. His thoughts scrambled, his dick hardening for no good reason, a damp spot appearing in his crotch. What was happening? Why was he so hot and horny and dizzy?!
He flung a hand out as his balls clenched, oh god, he was climaxing, cumming in his pants right there in front of Mister E and-
-Cool Dog wobbled unsteadily, grasping at the shelf nearby, his hips bucking as the damp stain on his pants spread further. “Ahhh, fuuuu~ That felt sooo good, yo!”
“Are you okay, sir?” Mister E’s voice held a note of satisfaction in it.
“Like, whoa, dude! My head’s all fuzzy, yo!” Cool dog glanced down at the damp stain on the crotch of his jeans. He laughed. “Brroooo! Clean up on aisle 6!”
Mister E handed him a couple of paper towels. “Clean yourself up, sir.”
“Thanks, bro!” Cool Dog grinned, soaking up as much of the jizz he could. Surprisingly, the paper towels worked incredibly well. The stain was no longer nearly as noticeable. “Talk about absorbent!
“Alright. Are you ready to try again?” Mister E asked patiently.
“Try what, bro?” Cool dog glanced up, cocking his head in confusion.
“Who are you supposed to be?” Mister E’s arms were crossed.
Cool Dog flipped the giant glasses down and crossed his arms, striking a pose. “Who am I? Who am I?! I’m Cool Dog, yo!”
Mister E stared at him blankly. “Cool…Dog… Really? Still? That’s really the best you could literally ever come up with?”
“Yo Yo Yo!”
Mister E rubbed his mask with a gloved hand. “…Very well. Welcome to my Masquerade… ‘Cool Dog’…”
Cool Dog swaggered into the party.