Party Crashers [Halloween 2026]

Part 1 of 4

"So, yeah... we need your help."

Jace Holland folded his arms, glancing between four of his football teammates. Three of them looked eagerly hopeful, the fourth seemed exasperated. The three eager teammates had cornered him in the locker room, and the fourth had grudgingly followed them over. They had just finished one of their last football games as high school seniors, and the group of them had headed over as the locker room started to empty out.

"Look, guys, I can't just wave my hand and change the law." Jace protested.

"Forget the law! We're looking for some kind of secret entrance."

Jace sighed, and glanced between his teammates. On the far left was one of Jace's closest friends, Matthew Chester. He was a muscular guy who had brown hair that was usually a little spiky at the front and dark gray eyes. Jace and Matt had been best friends ever since middle school, when they'd tried out for the football team together in the sixth grade. It was Matt's inclusion that was really making Jace consider this, as if it was just the other guys, he would have said no straight away.

Well, he liked two of the other three teammates well enough, but they weren't super close. Ryan Anderson was one of the three who were looking hopeful, while Lucas Lake was the exasperated one, and Jace knew how Lucas felt. Ryan had brown skin, short dark brown hair, brown eyes, and he was a tall, lean guy. Ryan was a sociable guy, kind of the jokester of the football squad, and pretty much everyone liked him. It was a popular joke around the football team that Ryan was more interested in older women than girls at their high school, but as far as Jace knew, Ryan's pursuit of MILFs and cougars hadn't gone so well for him.

As for Lucas, he was an athletic guy with dark brown hair and blue eyes, and was one of the nicest guys on the team. Him and Jace had been pretty close on the middle school team, but they'd grown apart a bit when they entered high school. It wasn't either of their fault, it was just how it had happened. Their class schedules hadn't lined up, the football team was way bigger, and they'd just kind of stopped hanging out. Lucas often was the wisdom to Ryan's wild, and Jace was unsurprised that Lucas wasn't super thrilled with this plan.

Jace looked to his last teammate, and the one he liked least out of these four: Evan Simmons. The tall, black-haired boy wasn't someone Jace would have expected to ask for his help, but he supposed there really wasn't anyone else he could ask. Jace and Evan were neighbors, both of them living in the neighborhood of Quartz Fields, and they really did not get along. They'd been feuding for years, but at least Evan wasn't an irredeemable asshole like some of the other guys on the football team.

"C'mon, man." Ryan pleaded. "The Glassy Ike's Halloween party is legendary! It's a bunch of sexy former cheerleaders who are dressed up for the sluttiest night of the year. We cannot miss this."

"I'm not as cougar-crazy as Anderson, but you've gotta admit, this party is the place to be." Evan chimed in. "And it won't even interfere with your plans, I know you wanted to hit Skylar's party, but that's tomorrow night."

Jace sighed. Skylar Wayne, the queen bee of Violet River High, was indeed throwing a huge Halloween party tomorrow night, which was actually Halloween. As for Glassy Ike's, they were throwing their 21+ party tonight, on Friday rather than tomorrow, the actual day of Halloween. Jace was planning on attending along with his twin sister Dana and his other best friend Amy Blackson. Amy had talked him into a duo costume of Captain America and Black Widow, and he was looking forward to it.

"And we know you had that summer job at Ike's." Matt pointed out. "You've gotta have a way in."

Glassy Ike's Bar and Grill was a pretty solid restaurant and bar, but what it was really famous for was being the 'cheerleader bar.' In small town Amethyst Shore, the former high school cheerleaders were often little mini-celebrities, and nowhere in town had a bigger congregation of them than Ike's. The place was ran by Elise Isaak, a former cheer captain herself, and most of the staff were either former cheerleaders or relatives of one, which was the case for Jace when he'd worked there over the summer.

Jace actually had a lot of former cheerleaders in his family, including his mother Danielle, his aunt Daphne, his older sister Daisy, and his twin sister Dana was a current cheerleader. With the exception of Dana, all of them had been cheer captains, too, so Elise was very familiar with who his family was when he'd went to apply. Jace had gotten the job, and had a blast over the summer, seeing plenty of the sexy cheerleaders coming through the bar. Him and Elise had gotten pretty close too, and Jace suspected he probably could ask her for help getting into the famous Halloween party.

"I... might have somebody I could call." Jace finally admitted.

"Dude, yes!" Ryan exclaimed. "You're the best!"

"Hold on, she hasn't said yes yet." Jace protested.

Ryan carried on like it was already a sure thing, however. "We need costumes that can cover our faces. We don't wanna get outed as soon as we get in."

"Agreed." Evan nodded.

"Group costume?" Matt queried, glancing around the five guys. "What group has five members? Power Rangers?"

"Yeah, two of which are women." Evan pointed out.

"True, true." Matt admitted, rubbing his chin thoughtfully.

"We need good costumes." Ryan insisted. "Not some little kid stuff, something that's gonna impress the ladies."

"Kind of a short turnaround time for that." Lucas noted.

"You guys figure that out, I'm gonna make a phone call, I guess." Jace said, grabbing his phone and standing up. He walked over to a secluded corner of the locker room, and opened up his phone. He had to scroll through his contacts a bit, but he finally spotted the right name and pressed it. Elise Isaak.

"Hey, you." her familiar, naturally sultry voice filled his ear just two rings later. "What's up?"

"Elise! Hey, it's been a while." Jace said, smiling at just the sound of her.

"Probably because someone quit working here." Elise retorted, and he could almost hear a smirk on her face.

"Yeah, well, school comes first and all that." Jace shrugged.

"Uh huh." Elise said disbelievingly. "Well, if you're calling for your job back, I think I could squeeze you in."

Jace was actually pretty tempted by that offer. His cash was dwindling after a couple jobless months, and he wouldn't mind spending a couple of his evenings at the cheerleader bar.

"Not at the moment, but it does sound tempting." Jace admitted. "I'm actually calling about an event happening tonight at Ike's."

"Oh, God. Don't tell me you're trying to crash my party." Elise groaned.

"Well, crash implies you don't know about it." Jace pointed out. "I'm really just calling for a few invites."

"A few?" Elise demanded. "I can't have a bunch of eighteen year olds running around tonight, Jace. I do run a bar, you know."

"Not a bunch! Just... five of us?" Jace tried.

"Five?! Shit, Jace. I could maybe get you in, but five?" Elise complained.

"C'mon, Elise. Please?" Jace asked hopefully.

"Ugh. Fine. But you're working next weekend, both days, and I'm not paying you a dime for it." Elise shot back. "Sound fair?"

"More than fair." Jace nodded emphatically. "And while I'm there, maybe we can discuss me coming back part-time."

"Hmmph. Maybe if you and your dumb friends don't get me in trouble." Elise replied grouchily, but the sass and the grouch was all just part of who she was.

Jace almost stuck up for his friends, then looked over to see Ryan and Matt were arguing loudly about the merits of a ninja turtles and Splinter group costume, and thought better of it.

"We'll be on our best behavior." Jace assured her, and Elise made a noise of clear disbelief.

"I'll believe it when I see it." Elise said wryly. "I'll meet you at the back door, just send me a text whenever you get there."

"Will do." Jace nodded.

"Oh, and make sure you hide your phone when you text me." Elise reminded him hastily.

With a jolt, Jace reminded the content of some of his texts with Elise, and he had no idea what their last text exchange had been. "Oh, yeah, that's a great point. Hey, uh... what are you wearing tonight?"

"Sorry, Casanova. That's a surprise."

———

Glassy Ike's Bar and Grill was a large square red brick building, near to the center of town but not directly in the center. It was two stories and had a nice open lot to itself, far enough away from the center of town that it didn't have any adjoining storefronts. There was a pretty full parking lot tonight, but Jace and the guys had walked here tonight, just in case they did wind up managing to get drunk. They could have had Lucas drive, as there was no way that he was going to drink, Lucas hated breaking rules. Laws? Couldn't even imagine it.

Ike's had exterior sitting out back, along with some cornhole boards set up, though they were currently unused. A few people were milling around the back, but most of the party was happening inside, Jace knew. Jace led his friends to the side entrance, glancing back at them as they walked. They had eventually decided to not do a group costume, in part because it was probably better that they weren't immediately obvious as a group.

So instead, they'd done a variety of costumes. Jace himself had picked Green Arrow, specifically the suit from the show with short sleeves to show off his muscles. That was important when wearing a comic book costume, in Jace's opinion at least. He wore a lot of green leather, had a quiver on his back, and wore a mask and hood. The bow that came with the costume was attached to the quiver, and the quiver was full of what looked like arrows but was really just a little plastic thing meant to look like a fake quiver of arrows. Matt, kind of matching Jace kind of not, had gone for Daredevil, the red to Jace's green. Matt, of course, was not blind, but the helmet for the suit obscured the top half of his head, and the helmet had see-through eyes. He wore a belt that Daredevil's sticks were stuck through, and Jace and Matt both thought their outfits looked pretty damn cool.

Evan had gone for Jason from Friday the 13th, meaning he was in jeans, a dark shirt, a green jacket he had gotten purposefully messy, and then the iconic hockey mask, plus a rubber machete with fake blood on it. Lucas had gone for the Dread Pirate Roberts from the Princess Bride, meaning he was in a loose black tunic kind of top, with black pants, black boots, black gloves, a long thin fake sword on his hip, a black mask over the eyes, and a black head wrap to truly mask his identity. The last member of their group Ryan had gone for a classic werewolf costume, meaning some ripped jeans he'd stuck fur to, a red flannel shirt, some more fake fur attached to the back of his hands, and then a big fake wolf mask covering his whole head.

"Dude, this better work." Ryan said urgently. "I'm way too excited for this to just fail now."

"Have some faith." Matt protested. "Jace has got this. Right, Jace?"

"Oh, we'll get in." Jace nodded. "How long we stick around for, I dunno, and I'm working next weekend for free for you guys."

"Everyone say 'thank you, Jace.'" Matt said gravely, and a chorus of 'thank you, Jace' went up, making Jace groan and roll his eyes. Matt burst out laughing as Jace lifted his hand to rap his knuckles against the side door. The door opened to reveal a busty devil, who laughed.

"Elise! Your party crashers are here!" the devil grinned, looking over the five high school boys. The woman in the devil costume, Yasmin Zima, was someone quite familiar to Jace, and he very much enjoyed the sight of her in her sexy devil costume. Yaz was in a red corset with the laces done quite loosely, showing off bountiful amounts of her light brown cleavage, along with some red fingerless gloves and red thigh high boots to match. She, of course, had a pair of red devil horns on top of her dark brown hair, and her dark brown eyes were deeply amused as she looked to Jace.

"Looking good there, Jacey." Yaz winked at him. Apparently his disguise wasn't good enough to fool people if they knew what they were looking for.

"You too, Yaz." Jace grinned. Yasmin, who was 24, was one of the bartenders here at Glassy Ike's, and one of the ladies Jace had worked with a lot during his time working here over the summer. Yasmin was the one who had trained him on most of his duties, and she was just a lot of fun to work with, even when she wasn't spilling out of a corset.

"Oh, me?" Yasmin said innocently, doing a little 360 that showed off her round, curvy ass and the devil tail coming out of her corset.

Jace heard one of the guys beside him, he was pretty sure it was Ryan, groan quietly at the sight of Yaz showing off.

"Definitely you." Jace said as another woman walked up beside Yasmin.

"Yaz, get back to work." the newcomer said, and Yasmin nodded.

"See ya!" Yaz called, heading back inside the bar.

"At least you had the brains to cover your face." Elise Isaak sighed as she took Yasmin's place standing in the doorway. The owner of Glassy Ike's, Elise was a gorgeous thirty year old woman, with long, sandy blonde hair and pretty blue eyes. She had some perfectly shaped medium sized breasts, and Jace would know. He'd gotten more than a little naughty with his boss during his summer employed here. A former cheerleader, Elise had actually been the cheer captain during Amy's aunt Sierra's senior year. Tonight, Elise was dressed up as a pale blue Playboy Bunny, and it was the kind of costume that made Jace's eyes wanna pop out of his head like a cartoon character.

Elise's C cups were shown off nicely by the cups of the little pale blue corset bodysuit that she wore. They weren't pressed together by the outfit, but the costume was working like a push-up bra, a really excellent one. Elise's smooth toned legs were bare from the hip all the way down to the black heels she was wearing, making her long legs look even better. She had the bowtie collar and the bunny ears headband on, of course, and she also wore a teasing little smirk as she looked at Jace, like she knew the exact impure thoughts currently running through his head.

"Well, we didn't want to get immediately kicked out." Jace explained, and Elise nodded.

"Yeah, you boys better not blow any of your covers, or I'm going to be very pissed." Elise warned, her smirk dropping as she looked at the other four boys. "I get it, you're probably all looking for some hot cheerleader action, but no drinking, and most importantly: do not get caught. Run out the fucking door if you have to, but if any of you get the cops called on this party, I'm going to kick your asses personally."

"Aye, aye, ma'am." Evan said, saluting, making Elise roll her eyes.

"Green Arrow, Daredevil, Dread Pirate Roberts, Jason, and Werewolf." Elise recited. "All the bartenders are going to know you five, understood?"

The boys chorused that they understood, and Elise nodded. "Alright, the four of you who don't work for me are free to go mingle."

Elise stepped out of the way, and Ryan was the first one up, bounding through the door excitably. Lucas followed, looking sheepish, then Evan. Matt turned and mouthed 'good luck' at Jace before following the guys through. Jace saw Yasmin pop up and direct them out from behind the bar one at a time, but then Elise stepped back in front of the doorway, blocking his view.

"You..." Elise said as she stepped out of the doorway, her hips swinging as she walked towards him. "...have brought me one very big headache for this Halloween party."

"And I'm very grateful." Jace said with a hopeful grin.

"Uh huh." Elise said with a glare. "You better be. Even with me getting a free weekend of work out of you, this is not worth it for me."

"I can sweeten the deal later tonight, if you'd like." Jace said, waggling his eyebrows.

"Nuh uh." Elise waggled her finger. "Tonight's a busy night, you'll have to find some other kitten to entertain you."

Jace sighed. "Well, that sucks. I might have told my friends no if I'd known you were off the table."

"You mean this wasn't your idea?" Elise gasped in dramatic shock. "This seemed like such a Jace Holland idea. Color me stunned."

"Yeah, this wasn't me, actually. The four of them came asking for help because they knew I had an in with you." Jace shrugged.

"You do not have an in with me." Elise scoffed, then she reached out and poked his chest hard. "And not a single joke from you about having been in me."

Jace, who had just opened his mouth, closed it sadly. "I... would never?"

"Uh huh, sure." Elise smirked knowingly. "Get in there and enjoy the party, alright? I'll see you later."

"Is that a promise?" Jace asked, and Elise shrugged lightly, making her tits bounce rather enticingly.

"Who knows?" Elise said, turning to walk back into the bar, revealing the cute little cottonball tail on the back of her corset bodysuit. "Oh, but Jace... when you work next weekend, you better believe you're staying late."

Jace's face split into a big grin, but Elise had turned and walked off as soon as she said it, her hips swaying way more than they needed to as she went back into the bar. Taking that summer job had been the best choice of his entire life, he decided at once.

———

Matthew Chester was damn glad he'd remembered Jace had worked here over the summer.

Ryan's initial plan had just been to sneak into the party, which wasn't really the smartest idea. Lucas was fully out of that plan, and Matt himself had been waffling a bit, though Ryan and Evan were sure they could pull it off. Fortunately for all of them, Matt had remembered that his best buddy Jace had worked here over the summer, and reportedly had had a great time. Matt had visited him a few times, as during daylight hours, this place was a normal restaurant, just with a bar. It was only during nighttime that the place became 21+.

Jace had told Matt how great his boss was, and so Matt had hoped that Jace would be able to get this plan off its' feet without anyone winding up getting in trouble for trying to sneak into a bar. So far, it had been a fantastic success. The stupidly sexy devil bartender had waved them through, Jace's super sexy Playboy bunny boss had been fine with them coming in, though she'd handed out some harsh warnings. And now Matt was in a party with the highest concentration of scantily-clad sexy older women that he'd ever been to. By a lot. Matt didn't even really know where to look, and he was damn glad that his mask covered his eyes. His eyes slid across a sexy group of ladies dressed as Disney princesses, all of them sitting at one table, and he'd been checking them out reflexively before he realized with a jolt that he knew those women! Hell, half of them were his teachers!

Ms. Kayla Roberts, his Chemistry teacher, was a very sexy Cinderella, wearing a little light blue dress that cut off quite high up her thighs. She wore white stockings up to about mid-thigh, and white gloves up to just below her elbows. Her long blonde hair was pulled up into the classic Cinderella bun with a pale blue headband, though a few strands at the front had escaped, and she wore a black choker. She'd done some sparkly blue eyeliner, and her lips were a bright cherry red. The dress she wore had quite a low-cut sweetheart neckline, showing off some incredible cleavage from her tanned large breasts, which made for a fun contrasts with the little princess-y puffs of fabric on her shoulder. Suffice it to say, the hot 29 year old blonde was looking incredible.

Also amongst the Disney princesses was Ms. Jessica West, who was by far the MILFiest teacher at school. She was rocking it as Snow White tonight, Matt had to say. She wore her dark brown hair down, with a cute red bow at the back of her head. Like Kayla, she wore a tiny, sexy version of Snow White's dress, with a tight dark blue bodice decorated with red laces and a yellow skirt that only just about covered her bubble butt, revealing the fishnet stockings adorning her legs. Her dress had a flared lace collar, but her hair covered most of it. Jessica already had quite naturally pale skin, but the smoky eye and bright red lipstick she'd done only exaggerated the paleness of her skin.

There was one last teacher among the group of Disney princesses, and this one frankly stunned Matt. Ms. Grace Marsden, the health teacher, was wearing what was definitely the most modest Disney princess outfit of the bunch, though her little Belle dress wasn't covering a whole lot. She had her long brown hair elegantly styled like Belle's in the movie, and the yellow dress she wore came down to about mid-thigh, the lowest skirt of the bunch. The dress was off-the-shoulder, revealing a hint of the cleavage that her perky, smallish-medium breasts created. Unlike her friends, Grace wasn't dressed up as a slutty princess, just a sexy one. For some reason, Grace was really rocking the Belle costume too, it looked perfect on her. Maybe the fact she was also a cute, bookish brunette... OK, so maybe Belle was his favorite Disney princess growing up.

As for the last three Disney princesses in the bunch, they were somehow even sluttier. Two of them Matt knew well, the last he barely knew at all, though he did recognize her. The two that Matt knew, Daphne Franklin and Sierra Collins, had gone all out. Daphne wore a golden tiara and her sexed up Sleeping Beauty outfit was in two pieces. The bodice of the pink dress had been turned into a crop top, while on her lower half, Daphne wore a pair of lacy pink panties and a very sheer pink tutu that didn't even go down far enough to cover all her panties. Daphne's plump, very large tits, which were bigger even than her elder sister Danielle's, were practically spilling out of that bodice crop top, looking like they might bounce free if Daphne jumped. Her gorgeous tanned legs were covered by sheer white stockings, and there was garter straps attached from her panties to those stockings. She looked fucking hot, and that was even without taking into account Matt's personal weakness for women of the Franklin bloodline. They were all just so sexy, but Matt had kept a respectful distance, considering Jace being his best friend and all that.

Matt's gaze moved to the pale ginger beside her, as somehow Sierra Collins had squeezed those very large tits of hers into a purple seashell bra, though like Daphne's, that situation was looking a little precarious. She'd also matched Daphne in another way, doing her bottoms as a pair of lacy green panties with a see-through green tutu to match. She didn't wear any stockings, showing off her pale legs, and she'd put a little starfish clip into her hair, to add to the Little Mermaid costume, Matt supposed. Sierra was currently sipping a green margarita while chatting to the last Disney princess of the group, the one Matt barely knew.

He knew she was a member of Kayla Roberts' cheer squad, but he wasn't all that familiar with the sexy Latina who was dressed up as Jasmine. Her name was Sarita Ramos, that much Matt knew, but that was about it. Well, he knew something else, and that was that she looked damn sexy as Jasmine. The black-haired Latina had done her hair in the Jasmine braid, and it looked like she had long enough hair to do it pretty much perfectly. Her medium-to-large olive breasts looked fantastic in the tiny little teal top she had on, embellished with golden chain jewelry that adorned her stomach, which was flat, toned, and gorgeous. She wore a pair of tiny teal shorts that emphasized her incredible bubble butt, but the shorts did have light separated skirts flowing from it that gave the impression of a more modest bottom, though whenever the skirts moved, it was obvious that it was just some tiny shorts. Sarita had dolled up with lots of jewelry, Matt noticed, and she looked like a desert princess, despite the fact it was the devilishly sexy Yasmin behind the bar who had traces of Arabic heritage.

It was hard for Matt to pull his gaze off of the sexy Disney princesses, but he did his best. Daredevil might be blind, but he was pretty sure people would be able to guess he was seeing what it was his head was turned towards. Realizing he needed a drink, Matt approached the bar, where he was greeted by a friendly dark-skinned girl dressed as an angel who looked to be about 28. She had long curly black hair, which tonight had a halo coming out of the top of it, one that started wobbling whenever she moved her head even slightly. As for her outfit, it was considerably more modest than Yasmin's devil. This girl wore a feathery-looking white dress (with wings coming out the back) that went down about midway down her smooth brown thighs, with a neckline that showed off the cleavage of her medium-sized breasts.

"Hey! What can I get for you tonight?" the angel asked, a smile on her face. Then she looked at his outfit and glanced over towards Yasmin, who was serving a guy with spiky blonde hair and an asshole kind of smile dressed like Cupid, which meant he was wearing essentially just a loincloth. The guy looked athletic, but he also looked like a major douche. It practically oozed off of him.

"Yaz, is this-"

"Yup! Keep an eye on that one, Francine." Yasmin called back, pointing two fingers at her eyes and then shooting them back towards Matt in the age-old 'I'm watching you' gesture.

"No alcohol." the angel, Francine, said with a good-natured smile. "Do you still want something?"

"Yeah, I'll just do a Coke." Matt nodded.

"Coming right up!" Francine smiled, and she grabbed a glass. As the angel made his drink, Matt looked around. He spotted a MILF blonde in a cop costume, one who looked really familiar, but he couldn't quite place her. The cop outfit was skintight, showing off her large breasts, wide hips, and her perky, shapely ass. The cop uniform had a nice open collar too, revealing some fantastic cleavage. The familiar blonde woman wore aviator sunglasses and a cop hat, as well as some fishnet stockings coming out of her knee high boots.

"One Coke." Francine said, setting it down on the bar. "You want to start a tab of Cokes, or do you just wanna pay now?"

"I'll just start a tab, then I only have to fish some money out of this thing once." Matt said, patting his costume.

Francine laughed, nodding. "You got it, Daredevil."

———

"This party is everything I dreamed of." Ryan Anderson exhaled. He was sitting at a table beside his best friend Lucas Lake, who might have been the smarter one when picking a costume for tonight. Lucas wore a Dread Pirate Roberts costume, which was both cool and a lot less restrictive than this stupid werewolf mask he'd picked. It didn't help that he couldn't even take the mask off for fear of being found out.

"Really? You dreamed of sitting in the corner and looking at women instead of actually talking to them?" Lucas asked with a faint smile.

"Well, I guess my dreams do typically have the MILFs closer than they are currently." Ryan allowed. "In my lap, or right next to me, you know?"

"Unfortunately, I do know." Lucas sighed. "You've told me all about the older women of this town, including my own mother, which is why you don't get invited over to my house anymore."

"Hey, all I've said is that your mom was pretty!" Ryan protested. "I've said a lot worse about other guys' moms. I think Jace would kill me if he heard even half of the things I've said about his mom."

"He'd kill you twice if he heard half." Lucas said wryly. "He'd kill you once if he heard a quarter of the things."

"Oh, come on. I know you're all about 'girls your age' and lame stuff like that-"

"Normal stuff." Lucas said mildly, but Ryan just kept talking.

"-but even you have to admit that Danielle Holland is prime fucking MILF material." Ryan finished.

"She's certainly an attractive woman." Lucas agreed. "I think you might take it a little far though."

"Pssh. You should be glad I haven't ditched you to go be best friends with Matt. I bet Matt has seen a lot more of Danielle than I have." Ryan scowled. "But this party has lots of great MILFs, even if Danielle Holland isn't here tonight. Which is a tragedy, but it's something I'll just have to live with, you know?"

"Do you think about anything other than MILFs?" Lucas sighed.

"Yes! I also think about cougars, which are equally as good as MILFs, they just haven't had kids." Ryan said firmly.

Lucas buried his face in his hands. "Why are you like this?"

"Maybe we could do some kind of two-man here." Ryan suggested, casting his gaze around the room.

There was Eloise Nelson, looking fucking fantastic in a cop costume. The cop costume, however, was a reminder of her husband Lawrence Nelson's job, which was as an actual cop... probably not the kind of guy Ryan wanted to piss off by sleeping with his wife. So, with one last longing look at Eloise's fantastic body, he moved on.

His gaze shifted over to another beautiful MILF, the lovely Ivory Yorke, a pale woman with long, dark brown hair, some pretty hazel eyes, medium-to-large breasts that sat nice on her chest, and a lovely curvy ass. Tonight, Ivory was dressed like a pirate captain, with a big black and red tricorn hat, a ruffly white top under a black corset, with brown leather shorts, black fishnets, and thigh high boots. Golden bangles adorned her arms, and a big emerald necklace glittered on her chest, right above her creamy cleavage. Ivory was the cheer captain the year before Danielle Holland, and Ryan believed there was a rivalry of some kind between her and Danielle, but he wasn't privy to all the details. He did know a lot about who MILFs were, though, and more importantly, who their husbands were. In Ivory's case, that little husband sitch came in the form of Reginald Yorke, a big time lawyer who put the Yorke in Chase, Sigler, and Yorke. Literally.

Ryan scanned the room, but he saw no sign of Reginald, or Ivory's hot best friend Portia Zenner. Maybe the sexy Mrs. Yorke had come to this party alone tonight. While wary of Reginald, Ryan decided to put Ivory down as a maybe. Other MILFs, other MILFs... ooh, not a MILF, but a cougar!

There was none other than Ryan's own teacher Jessica West, dressed up as a very sexy, nay, slutty Snow White as she headed over to the bar wearing stripper heels. Ryan took a long minute to commit the memory of his teacher wearing a outfit like that to memory, because damn! Ryan followed Jessica's path back to her table, and was awed by the view of Kayla Roberts, Daphne Franklin, Sarita Ramos and Sierra Collins all dressed up just as sexily. That was fucking cougar central over there or something, and Ryan was infatuated. Grace Marsden was there, too, but she wasn't really Ryan's type. He liked them wild, barely clothed, and preferably busty. Grace, though cute, was none of those things. She was also only 27, which, while meaning she was definitely an older woman, didn't really put her into prime cougar status.

Ryan was aware he was unique in this, but he did genuinely prefer his women to be in or around their 30s. Some might say that was indicative of mommy issues, and while Ryan's own mother Faith Anderson was a buxom MILF in her own right- Ryan squashed those thoughts down hastily. Unbidden, though, his brain began concocting images of Faith in a slutty Tiana costume amongst all those other sexy Disney princesses, but he squashed that thought down too. Nope! He was not opening that particular box of worms tonight. Box of worms? Can of worms? Whatever.

"So... we just gonna sit here at the party you were dying to get into?" Lucas finally asked.

"I'm strategizing." Ryan protested.

"You strategize a lot, you know." Lucas mentioned. "In fact, I don't think I've ever seen your strategizing lead to actual action."

Ryan winced. "Ouch. Low blow there, Luc."

"It's a lot less intimidating approaching girls our age, I'm just saying." Lucas held up his hands.

"As it should be!" Ryan maintained. "The girls our age, they're great, you know? But these women... they've got the experience, they've aged like fine wine, and I've come looking for a glass of them."

"Alright, well, I can see Evan talking to some college girls. I know they're not twenty years older than you, so maybe you're not interested, but I think I'm going to go join him." Lucas said with a shrug.

"Lucas Lake, interested in talking to girls?" Ryan gasped. "I thought you were too boring to do anything except sit around at parties."

"Usually I am." Lucas agreed. "But Jace put himself out on a limb to get us into this party, nobody knows who I am, and I dunno... I'm feeling brave."

Ryan nodded slowly. "Well, hey... I hope your bravery works out for you. Good luck, man."

Lucas looked disappointed, but he nodded slowly. "Good luck to you, too."

Ryan watched his best friend go, feeling even more like a fish out of water. It was one thing talking a big game about busting into a big party full of sexy former cheerleaders and their friends, but actually being there... it was a little overwhelming. Just a little.

Which was why he needed a good strategy! He wasn't insecure or worried, he was just... plotting. Yeah... plotting.

He nodded to himself a little, and went back to surveying the room. Recon was an important part of strategizing, and probably any minute now, Ryan would find a golden opportunity, and he'd go get with his first MILF...

Any minute now...