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2025-01-19
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upskirt

Summary:

sometimes an outfit is all it takes. originally posted as day fourteen of kinktober 2023.

Work Text:

It was always the skirts that did it for him.

Not the ponytails, not the sparkly pom poms, not even the acrobatics. It was the small skirts that had his eyes wandering, following long legs and pretty thighs along the hallways of his former high school. His friends used to make fun of him, tell him how stupid he looked pining over the cheerleaders who would never even look his way.

Eddie used to tell them he wasn't pining, he was merely just… looking, for lack of a better word. He wasn't thinking about them, the little skirts in green and yellow swishing around soft looking thighs, when he was alone later, under the shower. Of course not.

Imagine his surprise, then, when he saw you — his favorite customer, wearing a red, white and black cheerleader uniform. You were in the corner of the room, chatting with your local college friends, sipping on a plastic cup. Hair in a high ponytail tied with a neat red bow, as red as the fake blood sprinkled on your body.

He might have choked a little on his beer, but he didn't pay much attention to it, concentrating it all on you. Not until Jeff elbows him on the ribs, scoffing at his friend. "Man, you're gonna catch flies with that mouth hanging open."

"Shut up." Eddie grumbled, looking away from you and back at his friends. "Do you think she saw?"

"You're not exactly subtle, Ed." Gareth points out. The younger boy turned to your group of friends and waves, and as Eddie did the same, he noticed you waving back.

Burying the urge to smother Gareth in his sleep, he managed a rather strained smile, and a three finger wave in your direction. He saw you hide your giggle behind your hand, and all of his worries faded away for a second. It must have been your pretty smile, barely concealed by a delicate hand, or the mixture of glitter and fake blood on your skin, making you glint in the dark. Either way, he decided that he didn't want to look away, not really.

As his friends engaged back in conversation with each other, and your friends remained entertained with whatever was the subject between them, your eyes met yet again. You gave him a discreet nod of your head, pointing to the glass doors that led to the backyard of the house. Eddie nodded back, and waited for you to go first before following you closely.

 

Eddie had met you when he decided to expand his side business after he graduated. No longer wanting to associate with the high school kids, no matter how well some of them would pay him with their daddy's money, he went for the college students next. Lingering around their parties, taking a stroll through the campus with his ever trusty lunchbox on days off of work.

It was on one of these strolls that he met you — clumsily sitting in front of him at a picnic table that resembled his old selling spot, dropping your bag on the table and asking him for a rolled joint because you were terrible at rolling, and you'd even pay extra if needed.

He decided that, from that moment on, you wouldn't have to roll your own joints ever again.

There was just something about you, something that Eddie couldn't quite put his finger on. Maybe it was how comfortable you made him feel, how easy the conversation flowed between you. How you would always rant about your day or infodump on the latest subject that caught your interest in class, or the last book you were reading. It was like you didn't mind that Eddie was virtually a stranger, you just accepted him in your life with open arms, and he did the same.

You started walking a thin line between merely a business relationship, and an actual friendship. Eddie started never letting you pay, telling you that your company was more than enough reward. After that, you came up with more creative ways to thank him. A mixtape, freshly baked sprinkle cookies, a new bracelet, black nail polish.

He wondered if he asked for a kiss as payment you'd give it to him.

Through the small crowd in the living room to the small back porch, he couldn't help but let his eyes wander over your form from behind. The way your skirt moved side to side when you walked, in perfect sync with your hips. The bag of your legs, the curve of your neck. It made his heart race, and his hands ache to touch.

Finally, you both passed through the doors, — you first, Eddie making sure to slide the door behind him close — breathing in the cool night air. The outside of the house was empty except for the two of you, and the neighbor's cat waltzing around the top of the fence.

"Got the good stuff, Munson?"

You were smiling as you sat down on an old, beat down couch to the left of the porch. He tried not to make it obvious he was staring at the way your thighs spread out as you sat, looking good enough to bite into. Instead, he looked down and fished out the smokes carton from the pocket of his leather jacket, and smirked right back at you.

"For you? Always."

That night, neither of you spoke much as you shared a spliff between the two of you. The silence was not awkward, nor was it uncomfortable. It was just the two of you and the chill October air, and the shitty music that came from the inside of the party.

While he took the last drag, you scooted closer to him, bringing your arm to the back of the couch. "I noticed you looking, you know."

Holding his breath, he asked, "What?"

"At me, silly. I noticed you looking at me the whole night."

Your voice was pure honey, but there was a malice in your eyes Eddie had never seen before. Swallowing hard, he shifted on his seat, incidentally closing the distance between you. "It's just that, uh… You look really pretty tonight. Not that you don't look pretty any other day," he panics, disgusting it with a flare of his hands, "but you look especially beautiful tonight."

"It's the outfit, isn't it? Never would have thought you had a thing for cheerleaders, Eds. Would have told you I used to be one way sooner if I'd known."

"This was yours?" His eyes felt like they were going to pop out of his head.

"Yeah. All the way through high school. It was fun while it lasted."

He hummed, but on the inside, Eddie wanted to scream. "Whoa, sweetheart. Gotta show me your moves one of these days."

"I could show you a few right now."

You got impossibly closer, your face inches from his own. Instead of kissing him like he expected you to do, you took one of his hands and placed it on your waist, not breaking eye contact with him. "You can touch me if you'd like, Eddie. It's okay, I want you to."

He sat up straighter, grabbing your waist earnestly now. "Can I kiss you, baby?"

With your nod as confirmation, he did. He kissed you long and deep, stealing the breath away from both of you. He tastes you on his tongue, smoke and cheap vodka lingering there, as you straddled his hips, pretty pleated skirt flaring around your hips.

Hands wandering over layers, mouths wandering over skin. Eddie kissed every spot he could find, from your mouth to your neck, sucking and biting bruises that knew would still be there in the morning. He squeezed your boobs through your tight top, massaging them in his rough hands, making you moan in his mouth. He drank each strangled moan, each sigh, fueling his want for you.

Your hands soon found the buckle of his belt, expertly opening it, and palming him through his boxers. He could almost feel embarrassed over how hard he already was, but he could sense that you were equally as eager, applying pressure on his cock, running your nails through the length of it just to feel him shiver under your ministrations.

You didn't break the kiss as you pulled him out of his underwear, stroking him slowly, pumping his cock with your hand, running your thumb over the head of it, slicking him with his own precum. Eddie bit your bottom lip to stay quiet, making you look at him through hooded eyes. "Feeling good, handsome?"

"Too good. Too fucking good to be true."

You chuckled, low and sexy. "It is true. It's all for you."

As you kept stroking and squeezing him in your hand, moving your thumb from the sensitive underside to the head, and down again, making his hips jerked and thrusted into your grip, he kept kissing you, pouring all of his adoration into it, sucking on your tongue, bruising your lips with his own.

A chill ran down his spine with a particular tug of your hand on his cock. At the feeling of it, Eddie put a hand on your wrist, stopping you. "Angel, I'm not gonna last long if you keep doing this."

"But I wanna make you cum, Eds." You pouted, looking down at him.

"You can make me cum inside of this perfect pussy, how about that?"

"I think I like that more, too."

Without warning, you pulled yourself up, standing in front of him. As if you were putting on a show, you bent down at the waist, and slowly removed your panties from under your skirt, tossing on the couch right next to him, and mounted him again. "You're gonna kill me, aren't you? Was that your plan all along?"

"I don't know. Is it working?"

This time, he grabbed your hips and helped you align yourself above his cock, rubbing his head along your entrance and letting it catch on your clit a couple of times before you sat yourself on him, taking him in slowly, accommodating the stretch inside of you.

It was heaven, right there, under that tiny cheerleader skirt.

"Trust me. It's working really damn well."

You lost yourselves in that moment, moving your hips in sync. Eddie was hypnotized by the way you bounced on him, each slide of your slick, warm pussy went straight through his whole body, making him hold tightly onto you, wrapping his arms around you.

All he could hear was your heavy breathing, your little whimpers better than the music that muffled his own stubborn moans that made their way out of his gaping mouth. He felt you squeeze him with your cunt as you pulled his hair, hips growing more and more reckless with each movement, signaling that you were close.

Eddie started to fuck up into you, making you bounce harder on his lap. He felt the way you lost balance, holding onto his shoulders and shutting your eyes hard.

"It's okay, pretty girl. You can let go. I'm right here with you, you can cum for me." He pleaded, "Please? Cum with me."

You came almost at the same time, squeezing each other's bodies, trying hard not to make too much noise. While you rode out your orgasms, Eddie left kisses all over your shoulder, to your neck, to the side of your face. A last kiss on your cheek, on the side where you were hiding your face on his neck.

"We should get out of here before someone catches us."

Your voice tickled the sensitive skin of his neck, and he ran his hand over your back. You were still joined under your skirt, his cock growing soft inside of you, but still terribly warm. "Your place or mine?"

You raised your face from its hiding place, and pushed a strand of his wild hair behind his ear. "Wherever we don't have to keep quiet like this."

"My place it is."