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Sleep Overs

Summary:

The Loser's club has a group sleepover every month.

Notes:

This contains explicit sex. All characters are aged up to 18.

Work Text:

It was sleepover night. This started back in middle school and it was now their senior year of high school. They had it once a month, where all of the losers would meet at one of their houses and they’d have a huge slumber party. This mostly took place at Bill’s house and tonight was no different.

They sat in a circle, playing the classic game of truth or dare. It was Stan’s turn to ask somebody. “Bill.” He announced. “Truth or dare?”

Bill looked up to meet Stan’s eyes. “Dare.” He replied confidently.

A few giggles escaped the mouths of the others. Stan smirked before eyeing Bill over. “Alright, come on over here.”

Bill grinned and crawled across the circle of his friends to get to Stan. Stan grabbed Bill and pushed him down across his lap. “I dare you to let me spank you, in front of everyone.”

Bill blushed a deep shade of red and nodded. “A-alright..”

Without warning, Stan brought a hand down swiftly across Bill’s ass. This made the boy jump and let out a whine.

The others in the circle giggled and squirmed in anticipation. Bill got up and rubbed his ass where Stan had slapped him before sitting back in his spot.

“Okay..” He glanced around before his eyes landed on a certain boy. “Eds. Truth or dare?”

Eddie blushed lightly. “Truth.”

“Of course!” Bill laughed. “Okay, if you have to pick two of us to sleep with, at the same time, who are you choosing?”

Eddie bit his lip and looked back and forth between his friends. “Um.. Richie and Stan because it would be funny to listen to them argue the whole time.”

“Argue and then angry fuck you.” Bill grinned, getting a laugh from everyone.

Eddie rolled his eyes. “Okay, Richie. Truth or dare?”

Richie grinned. “Dare.” He always chose dare.

Eddie crossed his arms. “Pick someone else in the group, and give them a handjob.”

Richie’s grin only widened. “God, what if I wanted to choose Bev?”

“Then finger her dumbass.” Stan snorted, causing Beverly to turn red.

Richie smirked. “If you insist.” He leaned over since Bev was sitting next to him.

Richie set his hand on Beverly’s thigh, slowly sliding it up her dress. He used his thumb and pointer finger to mess with the band of her underwear, snapping it against her hip. Bev whined and smacked his hand away.

Richie put his hand back just as quickly as it left her. He rubbed his finger against her heat through her panties. He could feel her grow wet under his touch as a small moan escaped her lips.

The other boys watched in amusement. They could all feel themselves start to get hard at the sight. Beverly pushed her hips up towards Richie’s hand and whimpered.

Richie pushed her soaked panties aside and slipped his finger inside of her. She immediately let out a loud whine. “Fuck Richie-”

Richie thrusted his finger in and out of her wet entrance, getting hard himself. “You look so pretty like this.” He whispered to her.

Beverly whimpered and pushed her hips against Richie’s hand, asking for more. Richie got the hint and added another finger into her, thrusting them in and out quickly.

Eddie was blushing deeply as he watched, his shorts growing tight around him. Bill had started rubbing himself through his jeans, and so had Ben.

Beverly arched up as Richie moved his hand faster, whimpering and gripping onto his shirt. “Richie please-” before she could even finish the sentence Richie pulled his fingers out of her.

“Look at what you did to them Bevvie.” Richie grinned, turning his attention to the boys. Beverly whined in response to the feeling of sudden emptiness.

“I think you should let them have a turn with you babydoll.” Richie pulled Beverly up in between his legs with her back pressed to his chest, holding her hips. “Come on, open up for them.”

Beverly blushed deeper and spread her legs as Richie told her to. The boys stared, Richie holding her in place. “Who’s first?” He asked.

Bill crawled over first, he was too hard that it was starting to hurt. He slid his hand up Beverly’s hip, grabbing her panties and pulling them down her legs. Bev bit her lip, watching the boy in front of her.

Bill pressed his finger against her entrance, circling it for a second. Then Richie shook his head. “I want you to use your mouth.”

Bill nodded, lowering himself between her thighs. He slowly licked her, earning a high-pitched whine. “Bill-” She squeaked.

Bill pushed his tongue into her, darting it in and out in a steady pace. Beverly squirmed, kicking her legs in pleasure.

Richie gripped her harder. “Don’t move.”

Stan groaned, trying not to touch himself. “You’re not in charge Richie.”

“Do something about it then, Uris.” Richie muttered, not paying much attention to him as his focus was on Bev and Bill, who were still going at it.

Stan got up and walked over, grabbing Richie by the hair. Richie moaned under his breath at the action. Beverly squirming in his lap didn’t help his growing erection.

Stan made Richie look at him. “You don’t own anyone here, quit acting like it.” Richie only groaned in response, digging his nails into Beverly’s side.

Beverly whimpered and tried to move away, only thrusting her hips into Bill’s face. Bill groaned and pulled Beverly away from Richie by her hips, gently laying her down on the floor.

The rest of the boys watched, growing harder and harder. They couldn’t sit and watch forever or they felt like they’d explode.

Stan shoved Richie down, straddling his waist. Stan started undoing Richie’s jeans before pulling them down his legs.

Eddie whimpered, starting to grind himself against the floor. He desperately wanted attention but didn’t know how to get it. That was until Stan turned his attention over to him. “Eds come here.”

Ben and Mike shared a glance before standing up. Nobody was getting left out tonight. Ben made his way over to Bev and Bill. Mike walked over and pulled Stan off of Richie.

Mike laid Stan down on his back and crawled on top of him. Stan pulled Mike down into a heated kiss, running his hands down his back. Mike groaned and began grinding his hips down against Stan’s, earning a moan against his own mouth.

At the same time, Richie pulled Eddie over to him. “Get these off. Now.” He tugged on Eddie’s shorts. Eddie nodded and pushed his shorts down before kicking them off into the corner. Richie grabbed Eddie and pulled him into his lap, instantly grinding up against the smaller boy.

Eddie whimpered in response and gripped Richie’s shoulders. “Please.” Richie knew what Eddie meant, and he didn’t want to wait any longer to give it to him. He pushed down Eddie’s underwear, then his own. Gently he lowered Eddie down onto his hard cock, causing him to whine in both pain and pleasure.

Beverly looked up at Bill, still exposed when Ben came over. Bill looked up and met Ben's eyes. “Help me with her.” He made Beverly get up, putting her on all fours. Ben nodded and stood in front of Beverly.

Beverly looked up at Ben nervously before he cupped her cheeks. “You’re okay princess.” He mumbled before kissing her. While she was distracted by Ben’s kiss, Bill undid his jeans and pulled them down with his underwear. His erection sprung up.

Bill grabbed Beverly by her hips and rubbed himself against her wet warmth. Beverly moaned into Ben’s mouth, gripping the carpet. Bill slowly pushed himself into her, causing her to whimper. Ben pulled away and took his own hard cock out, holding it in front of Bev.

Beverly took Ben into her mouth, moving her small hands to his thighs. Ben groaned and grabbed Bev’s hair, moving her head with the rhythm of his hips. She moaned against him as Bill began thrusting into her from behind.

Mike lowered his hands, getting Stan’s jeans off and pulling his cock out. He wrapped his hand around him, stroking him slowly at first and then picking up the pace. Stan moaned and dug his nails into Mike’s back, thrusting his hips against his hand.

Richie thrusted gently into Eddie, feeling his ass tighten around him. He groaned, holding Eddie’s hips and moving him up and down. Eddie whined loudly, his voice going across the room.

Bev whimpered in unison with Eddie, though it was hard for anyone to hear with Ben’s cock shoved down her throat. Ben tugged at Beverly’s hair, whispering sweet nothings to her as he face fucked her. Bill didn’t slow down at her whimpering, it only got him more turned on.

Bev could tell she was close, even if she had never come before as this was her first time with her boys.

Mike pushed his own jeans and boxers off, still using his other hand on Stan. He lined himself up with Stan’s ass and slowly pushed his way in. Stan whined and jerked his hips up. Mike leaned down and connected his lips with Stan’s once again in another heated kiss.

With all of them together it was getting harder and harder to hold back. Even with their attention on the ones that they were currently fucking, they couldn’t help but glance at each other.

It wasn’t long before Beverly came, being the first one that night. Bill couldn’t hold back much longer either, pulling out and releasing onto the backs of Beverly’s pale thighs. She whimpered and held onto Ben’s legs as he kept his pace.

Richie gripped onto Eddie’s thighs, letting him ride his cock at his own pace. He had his eyes closed tightly but his mouth open in an almost constant moan. And fuck, Richie never saw him look better.

Eddie started bouncing, moving his hips quicker before he let himself go, releasing all over Richie’s stomach. Richie groaned and not a moment later he came inside of Eddie.

Mike thrusted roughly in and out of Stan, Stan’s choked moans echoing through the room. Stan came on himself, thrusting his hips up towards Mike. Mike watched as he came, filling Stan up. Both of them moaning together.

Ben pulled out of Beverly’s mouth after he came. He grabbed her chin, keeping her mouth shut. “Swallow for me princess.” Beverly obeyed, swallowing all of it as she looked up at Ben. Somehow she looked so innocent still.

Bill panted and sat back, trying to catch his breath. Ben wiped Bev’s mouth with his shirt and gently sat her down next to Bill before sitting next to her.

Eddie whimpered as he lifted himself off of Richie, all of his cum leaking out of him. Richie helped Eddie to sit down and rubbed his back as he whispered praises to him.

Mike pulled out, allowing his cum to flow from Stan who was still on his back panting. Mike pecked his lips before sitting back and looking at everyone else. They all stayed in the circle, staring at each other in slight disbelief they’d gone all the way.

They hadn’t planned to go all the way until much later once they could all move out and be together. But it was what it was, and now they had to get the place cleaned up before Bill’s parents got home.