Halloween Gangbang Double Feature

(Usual Disclaimer Time: All the characters in this story are 18 years old or older, and since we're living in the wide wonderful world of porno-land here, where clichés roam free and things might get a little unrealistic from time to time, please remember it's all in good fun.)

(Author's Note: This story is my entry to the 2023 Halloween Story Contest at Literotica. While it references characters and places from my ongoing Senior Year Memories series, this is a STANDALONE spin-off story created for this contest that does not require any knowledge of the series to enjoy; I'm trying to make it its own fun thing and aim to provide all necessary context. So, while some details may be familiar to longtime readers, it is meant to be accessible to newcomers as well.

Further, I want to thank my readers who helped select the story's cast, as well as congratulate my reader Patricio. for suggesting the name of the male lead (which I drew out of a hat, among other suggestions). As always, I want to give special thanks to fellow Literotica author Lil_kitty for her excellent work as my editor and acting as a second set of eyes on this chapter, and for letting me know what did and didn't work; if you get a chance, please check out her work and drop some stars if you enjoyed, she writes some very hot and fun stories.)

***

"Officious little prick."

All it took was those three little words. Well, two little words and a bigger one that did little to improve 18-year-old Gwen Savage's already foul mood. It was Halloween night, and with the streets dark and glowing with jack-o-lanterns and decorations, Gwen knew she should've been in the kind of festive mood that Halloween always put her in. Unfortunately, she'd drawn the short straw to be the night's designated driver, so things started off in a pretty miserable state. Though most of the trick-or-treaters had gone in for the night, there were still some out there, and she didn't need to be missing one not looking both ways before crossing the street in front of her because Sasha *fucking* Pearl had to throw out two little words, and one big one and making Gwen think harder than she wanted to tonight.

"What?" Gwen asked, lowering the volume on the car's speakers and (quieting "Don't Fear the Reaper did little to improve her mood) looking in the rearview mirror at her fellow Regan Hills High School cheerleader.

And Sasha was probably her friend, she guessed.

As ever, the willowy redhead with the unstylish glasses could've been mistaken for a fucking nerd if you didn't know how hot she was. Gwen was certain that Sasha's slutty Little Mermaid costume, combined with her hot body, was sure to get her some dick tonight. Sitting behind Gwen, she leaned forward to better get her point across.

That she was clearly already a little buzzed, even before the party, did little to settle Gwen's annoyance of having to be the "responsible" one.

"'Officious little prick'. That's what Jackie called Mr. Ullman after he tried mansplaining when she could and couldn't go to the bathroom in math class," Sasha explained. "And she's right, I mean, he had no right doing that."

"Who's Jackie?" Gwen asked, more annoyed at having to ask follow-up questions.

"Nice girl. Brown hair, decent-sized boobs, walks with a bit of a limp? She's smart, so she probably doesn't travel in your circles," Sasha chuckled sheepishly, eyeing the girl who sat next to her in the car's backseat for backup.

The stacked Latina, and fellow cheerleader, Jade Alvarez, was wearing her own take on a slutty Snow White costume (which Gwen had to say she was fucking *rocking*), looked from Sasha to Gwen, gauging the room before giving her own response. Seeing the blaze in Gwen's eyes, Jade soon turned her attention back to Sasha.

"Come on, that wasn't very nice, Sasha," Jade said, her voice friendly yet stern.

Chastened, Sasha turned her attention to Gwen. "You know I'm just messing with you, right? 'cause I'm a little buzzed? I didn't mean to make it seem like I thought you were... fuck..."

Sasha looked convincingly miserable, which gave Gwen a little thrill. She knew that people thought of her as a bitchy, big-titted blonde, and that she was hardly the smartest girl in school, and while there were times where it felt fine to joke about it, tonight was not one of those nights. As much as she was Sasha's friend, being called dumb by her, even jokingly, tempted Gwen into considering leaving her on the side of the road to walk the rest of the way to the party.

As usual, it was up to Jade to play a rather apt peacemaker. "She really didn't mean anything by it. Sasha?"

Jade eyed her redheaded friend sternly. Nodding, and understanding that she'd clearly pissed off their designated driver, Sasha leaned back in her seat.

"I'm sorry, Gwen. I didn't mean to piss you off, or be a bitch, or, fuck, man, I'm sorry. I just wanted to share the moment and let it make me stupid, but don't let my stupid make your night worse, yeah?" Sasha said, smiling that huge, goofy smile that Gwen always claimed to hate, even though it secretly warmed her heart.

Gwen rolled her eyes. "Whatever. It's Halloween. Good night for some fuckups, and you could've fucked this one up worse."

"Well, I'm still sorry," Sasha replied, leaning forward to squeeze her friend's shoulder. "And you're still the best, and making a huge and awesome sacrifice for us tonight, and we love you for it, and I'll do whatever it takes to pay you back."

"You can start by telling me, uh... that thing she called him?" Gwen said, trying to steer the conversation back on course.

After a moment of trying to remember where they'd left off, Sasha suggested, "Officious little prick?"

"Yeah, uh..." Gwen said, trailing off in her bitchiest tone, not wanting to admit that she didn't know a word.

Thankfully, without having to say it, her friends understood that side of her.

Jade reached up behind Gwen and put a calming hand on her shoulder. "Officious means an asshole, like, a guy who can't stop sticking his nose where it doesn't belong and thinks that he's the end-all, be-all of hot shit and big ideas."

That helped it click for Gwen, and though it did little for the bitchy sneer on her face, as she lined up the word with her impression of Regan Hills High School's least favorite math teacher, she agreed, "Yeah. He *is* an officious little prick."

"Fuck yeah, he is," Jade agreed, leaning back in her seat and smiling.

"See? Something we can all agree on. And we taught Gwen a new SAT word!" Sasha said teasingly, rubbing her friend's shoulder from behind again.

"Do you want me to poke her for you, Gwen? Because I'll *totally* poke her for you," Jade suggested.

"Poke away. Bitch's just asking for a good poking," Gwen replied, amused.

Jade was good to her word, poking Sasha in the side of her bare midriff enough to make her squeal in surprise and delight. Soon there was a full-fledged tickle fight going on in the backseat, full of enough laughter and gropes that Gwen wouldn't have been surprised if Sasha and Jade had just started getting it on back there.

It wouldn't be the first time, after all.

Gwen rolled her eyes and turned the volume back up on "Don't Fear the Reaper" so she wouldn't have to linger on her friends. Sasha was already a couple drinks in to enjoying Halloween night and not afraid to let it show. Jade was going to be a good girl, as always, and wait for the party before she got drunk and started slutting it up with Sasha. It wouldn't even take more than a drink or two for them to get lucky, by Gwen's estimation, while even a light buzz wasn't in the cards for her this Halloween.

She'd have to find another way to cause some trouble tonight... and oh, would there be opportunities. Halloween was an *excellent* night for mischief, after all.

As long as she could remember, her small hometown of Regan Hills, California, had always taken Halloween seriously. Even though October in Southern California was more like an extension of summer with every passing year, things looked enough like a spooky kind of Fall tonight that you could easily ignore the heat. It wasn't uncommon to see streets where every house had multiple lit jack-o-lanterns and other assorted decorations, with some homes going fairly over the top in an effort to attract as many trick-or-treaters as possible. There were entire blocks known for giving out top quality candy, meaning you'd get kids trucking in from several towns over looking for the best damn trick-or-treating you could find.

When she was little, Gwen loved to go trick-or-treating, and then maybe go for a good scare or two at the Halloween Scream carnival they held over at Regan Hills High School. The cheap, hastily thrown together haunted houses of the carnival used to scare the hell out of her, but now seemed to her the stupidest damn thing that someone could do with a night like this.

Growing up, Halloween had become less about seasonal adventure, and more about one thing and one thing only: parties. There were always a few good Halloween parties being thrown in town by one of her classmates, and after a few bad experiences at mediocre celebrations, Gwen had finally narrowed down the best, and for that matter, *only* party she was willing to attend.

"There's Scarlett's house," Jade instructed, pointing to a large suburban house up ahead.

Gwen's eyes widened on seeing the place. "It's lit up like the goddamn Fourth of July."

Projectors threw images of ghosts in windows, while the front yard itself was made up as an elaborate graveyard, with a number of static and moving figures of zombies used to further accentuate the scene. Dozens of lit jack-o-lanterns seemed to be crammed into every crevasse, while a smoke machine gave a decent foggy effect to the darkened cemetery. It wasn't exactly "scary", but spooky enough that the Halloween spirit was pretty thick around the place.

With music blaring from inside and a few of their classmates milling around out front, Gwen would've found the right place even without Jade's directions.

"Fuck yeah," she muttered to herself, grinning darkly.

It took a minute to find a decent parking spot, but when they did, the trio of cheerleaders exited the car with a determination that seemed more appropriate for storming a castle than it did approaching a local Halloween party. In their respective Snow White and Little Mermaid costumes, Jade and Sasha stepped out and straightened themselves, strolling toward the party with a clear eagerness.

As hot as Gwen could admit those two looked, she knew that tonight she was easily the hottest of the trio. At 5'0", Gwen was quite the stunner, in a vaguely trashy sort of way. Her long, dirty blonde hair fell about her pretty face, with sultry brown eyes that were lively in the way of a predator looking for their next prey. She wore slightly too much makeup even for the night, with heavy eyeliner, fake eyelashes and a crimson shade of lipstick that she mostly managed to pull off. Years of dance had given her a tight body, offset only by her impressive ass and full, D-cup breasts that looked all the more impressive in her slutty Little Red Riding hood outfit. Her corset was tight enough to make her boobs look fucking awesome, and the skirt short enough that it barely covered her ass. Combined with her flowing, hooded cloak, and she knew she looked positively gorgeous.

Yeah, there was no fucking way she wasn't getting some tonight.

"Anyone wanna take a bet on who's gonna get laid first tonight?" Gwen proposed, smirking as the trio crossed the street.

"Bets make things mean," Jade said, shaking her head.

"Yeah, but that's part of the *fun*," Gwen shot back. "And I'm all about *fun* tonight. Fun, or trouble, whatever's easier to find."

"If I say yes and then make a bet that you're gonna get laid first, then I can do nothing and still make some cash, right? I mean, Jade's looking fucking hot, but, you're gonna get it in like ten minutes, right? Yeah. I'm betting on you," Sasha said, toying with her purse as if she actually meant to pull out money.

"No, that's not how this fucking works," Gwen said, shaking her head. "I mean... fuck, why do I even try with you guys anymore?"

"Because we're your friends and we love you?" Jade said, fluttering her eyelashes playfully.

"And we know how to make you have fun even when you're determined to be a grumpy bitch, and it always, *always* works because we know you so well?" Sasha suggested.

Gwen shook her head in annoyance, mostly because they were right.

"Whatever," Gwen grumbled, hiding her smile.

Deciding to change the topic to brighten her friend's mood, Sasha said, "So, Gwen, you finally gonna seal the deal with Jason Torrance tonight?"

The busty blonde shivered slightly at the mention of his name. Jason Torrance was a certified hottie, six feet of toned muscle, a dreamy fucking face, and she had it on good authority from a couple other cheer sluts that he had a big fucking dick. She heard from even more people that he was also an actual dick, but that never stopped Gwen from giving a guy a chance if he was hot enough.

Gwen had been playing coy with him for a while now, teasing him and enjoying when he pursued her just long enough to tease her back, something that he was *very* good at. For a cocky bastard, there was something about him that was naturally intoxicating, and the back and forth pursuit between the two of them had been a lot of fun. But while it had been a game for the last couple weeks, Gwen thought that they were past the point of playing games.

She wanted some serious cock from Jason Torrance, and tonight she planned on getting it.

Playing it cool, she said, "I'm thinkin' about it."

"Correct me if I'm wrong, but, won't Jason fuck anything that moves? How is it sealing the deal if all you gotta do is ask, 'hey, wanna see my pussy?' Not exactly like there's a ton of challenge to him," Jade stated.

Gwen rolled her eyes as they approached the front door. "Fuck, you don't gotta be such a bitch about it, alright? I know he's easy, that's part of the draw... kind of makes us a matched set. It's just that getting with him's something I've been meaning to do for a while now, alright? And tonight's gonna be the fucking night."

"If you can pull him away from his bros," Sasha said, noting a problem that Gwen hadn't considered. "Have you ever seen those guys party? These guys can put a frat party to shame at the best of times, and tonight it's frickin' Halloween. They're gonna be *fuuuuuucked* up."

Now, Gwen was not a girl who backed down from a challenge easily. She also wasn't exactly one who was at her best when faced with a challenge, since many of those she faced usually ended in some kind of physical altercation, but her inability to back down was often considered one of her more admirable traits. When presented with the likely problem that Sasha noted, Gwen was quick to respond with a solution, however ill thought out it might have been.

"Fuck it. If they're glued to each other, I'll take 'em all on. It's fucking Halloween! Everybody knows that's the perfect time for a gangbang!" Gwen exclaimed, squaring off with the front door.

Keeping her voice low, Sasha replied, "Nobody says that, or knows that... but, you could still be right..."

Aware of the seasonal playlist booming loudly inside, Gwen repeatedly pressed the doorbell to make sure they were heard.

And then, for emphasis, she pressed it in another intense barrage, just to make sure they were heard, and that their entrance was known, because they were motherfucking Regan Hills High School cheerleaders, and they were going to make a fucking entrance.

The door opened soon after, held by a beautiful, 5'1", light-skinned black girl. With dark, curly hair that fell about her shoulders held back by a cat-ear headband tonight, a domino mask, and a skin-tight black bodysuit, Scarlett Bishop didn't make the fanciest retro Catwoman, but that didn't stop the party's host from owning every bit of her costume. Even though Gwen wanted to stay in her foul mood, it was hard not to find Scarlett's positive attitude slightly infectious. As probably the biggest party girl in school, and a damn fine mistress of ceremonies, Scarlett always threw the best parties in town, something that Gwen was looking forward to making their senior year exciting.

"Gwen! Jade! Sasha!" Scarlett exclaimed, offering each of them a quick, polite hug before beckoning them inside. "Come in, come in! God, I was wondering when we'd get some cheerleaders in here!"

As the trio of girls followed Scarlett inside, Sasha explained, "Yeah, a lot of the rest of the squad were roped in to helping out those school paper kids at the Halloween Scream, but, we're here!"

Gwen had to admit that Scarlett had gone all-out for the occasion, with the party's interior being lit by a number of blacklights, more Halloween decorations translating the darkened cemetery from outside to inside, and one of the tech geeks from school working a DJ table to keep the seasonal tunes flowing. The house seemed packed with almost everyone who was anyone at Regan Hills High wearing their most revealing and elaborate costumes, dancing, making out, getting drunk and high...

Fuck, this was gonna be an awesome night.

"Got snacks and drinks in the kitchen, games going on in the rec room, dancing wherever, y'all know where the bathrooms are, have fun and don't fuck my house up, alright?" Scarlett declared, raising her high voice over the music. "Hey everyone, the cheerleaders are FUCKING HERE!"

A cheer went up around the party, and for the briefest moment, Gwen basked in the attention, loving the feel of all the eyes on her, even if most of those eyes were peeking out from behind Halloween masks. Still, their introduction was brief, and soon Jade and Sasha filtered into the crowd looking for drinks and excitement.

Gwen sought to join them, but was stopped in place when Scarlett grabbed her by the elbow.

Before Gwen could say anything, Scarlett explained, "Look, Gwen, you love to party, I love to party, I think we get each other more than most, so I'll be real with you. I fucking love Halloween, and I put a lot of work into this party, and I don't want it ending in a fight, alright?"

"Why would it end in a fight?" Gwen asked, knowing full-well that she'd been in at least three fights at Scarlett's parties in the past, and that she was lucky that Scarlett still invited her.

"I know there's some bad blood between you girls and the color guard, and they're here in force tonight. They're my friends, and I told them to be on their best behavior, so now I'm telling you to be on yours, alright. I don't want you and Daphne starting anything again..." Scarlett continued.

Regan Hills High School's cheerleading squad and color guard had always been natural rivals, but that rivalry had only seemed to increase when Daphne O'Connell, the bitchiest of bitchy redheads in the world, had taken over as team captain for senior year. As arrogantly bitchy as she was leggy, stacked and gorgeous, Daphne was a particular pain in the ass for most of the cheerleaders in general, and Gwen specifically, because she wasn't willing to take that redhead's shit. They'd had their share of arguments in the past, but hadn't had the chance to throw down just yet... but the night was young.

Still, since she liked Scarlett, Gwen said, "I won't start nothing if she won't start anything."

Smiling nervously, Scarlett replied, "I'll hold you to that."

Gwen smiled politely, knowing full well that neither of them actually believed that Gwen wouldn't start something with Daphne if the opportunity arose. Still, she couldn't see the red-haired color guard captain, and there was every chance their paths wouldn't cross in a party this packed.