Once Upon a Halloween Ch. 05

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Double Penetration

(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: As a reminder, this story is a limited series with a light canon, meaning that while the chapters will all be related by characters and location, it won’t be explicitly necessary to read every chapter to know what’s going on. Each chapter will be its own thing, and can be enjoyed independently. I hope you enjoy! I also want to give special thanks to fellow Literotica author and SYM reader Lil_kitty for many excellent ideas and acting as a second set of eyes on this story, 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.)

***

When it came to Halloween, Richie Olson chose chaos.

It was an easy choice for him, honestly, one he’d made time and time again in his 18 years of life, and one he knew that he’d continue making in life because it was simply more fun than the alternative. Halloween was a night for mischief after all, and if everyone else in town was going to be engaging in more wholesome activities, well, he was more than happy to bring enough of that mischief to Briar’s Mill to make up for those who wouldn’t partake. With his best friend at his side, and each of them carrying a sack filled with eggs, toilet paper, silly string and firecrackers, Richie spent much of the night quite pleased that he had chosen chaos.

Unfortunately, choosing chaos wasn’t always without some consequence.

“We can make it!” Richie yelled as they ran down the middle of the street, trailing toilet paper behind them.

“Make what?” yelled Lucas Choi, Richie’s best friend and partner in crime. Wearing form-fitting black bodysuits painted to look like skeletons and skull-faced ski masks, the two were a matched set in every way. Both of them were tall and muscular, both of them were stars on the school’s track team, and both of them were currently doing a pretty good job running from a slow, relatively disinterested cop car. It was early in the evening, just late enough that most of the trick-or-treater’s were gone, but not so late that they were completely absent from the street. This alone made the cops extra cautious, and had kept Richie and Lucas safe.

“Freedom! Liberty! Mayhem!” Richie cried out.

“Dude, I think the mayhem is finished!” Lucas yelled, looking back at the car. It had its red and blue lights on, but followed behind them at barely a crawl. A police officer was angling the car’s spotlight at them, but only just.

Richie loved Lucas as if he were his own brother, but the two of them had their differences of opinions on many things. “The mayhem is never finished!”

“It will be soon if we’re caught!” Lucas exclaimed.

Richie had his doubts about that. He’d led a charmed life. Sure, he’d been busted a couple times before for underaged drinking, but his parents had always managed to get him out of trouble before any of that truly stuck. Lucas probably wasn’t as lucky on that front, because his family name didn’t mean as much in this town. While Richie may have been an admitted asshole, he wasn’t going to leave his best friend to get in trouble.

He eyed the street they were running toward, and recognizing where they were, he took a chance.

“Lucas, man, I need you to do exactly what I say, when I say it, okay? ’cause if you do, I’ll get you out of this,” Richie explained.

As someone who was used to listening to Richie even when his ideas were clearly shit because he usually knew how to pull them off, Lucas asked, “Alright, what is it?”

Watching the street sign at the intersection up ahead come into focus, Richie said, “Make a left up ahead and keep running. I’ll keep them busy!”

“You’ll what?” Lucas asked, dumbfounded as Richie stopped and turned around. Richie reached quickly into his bag and threw an egg from it at the cop car. The egg shattered, splattering the windshield. At this, they unleashed a quick burst of siren.

“Well, that got their attention,” Richie said, looking on with some pride as Lucas ran off. His friend would live to see another day of freedom, one where trouble with his family wouldn’t find him and the adrenaline rush of a Halloween well spent would give him a truly peaceful and profound night of sleep. Lucas would have a dull night from this point forward.

Richie’s night, on the other hand, was only beginning.

“HAPPY HALLOWEEN, MOTHERFUCKERS!” he roared, turning around on his feet and quickly took a right at the intersection.

The cop car had some additional speed to it now that he’d proven himself to be slightly more than a nuisance, and Richie knew that they would catch him quite soon.

Thankfully, that was where some planning came in handy. The street afyon seks hikayeleri he’d turned down, Ash Avenue, was one he’d spent a lot of time on as a kid, riding his bike around, getting in water fights with friends… he knew the houses here like the back of his hand, having spent many a night playing hide and seek hiding out in backyards. He wagered he knew this area better than Briar’s Mill’s poorly paid police force, and he was going to make their night hell.

Passing the first house, he put an extra burst of speed that had served him well at track meets, leaving the cops behind as he quickly darted between a pair of houses. Knowing the gate between the two houses to be locked, he quickly jumped up and over it, cutting left through the backyard as he hopped another fence. Somewhere in the distance he heard a couple of confused cops talking, debating what the hell to do next. Hopping from yard to yard, he knew he would soon be out of their search radius, and that they would give up before long. He and Lucas would be free to seek mayhem and chaos another day, and life would go on as it always had in Briar’s Mill, with the two of them acting as kings of the keep.

It was as he sprinted across the fourth yard and toward the Meyer’s backyard that Richie was given pause. The Meyers must have redone their fence, because where the top was once smooth, now the wooden slats had pointed tops. They weren’t so sharp as to mangle, but if he wasn’t careful, he could get hurt pretty easily.

He couldn’t see a ladder or anything he could use to climb over in a hurry, but there was a trampoline that was pretty close to the fence. It reminded him of a really old movie his dad made him watch once, Ferris Bueller’s Day Off… yeah, it had worked there, Richie couldn’t see any reason why it wouldn’t work now.

Lining himself up, he took a running leap toward the trampoline. His feet hit the springy material, and quite soon he was flying. That was it, he was making it over the fence! He was doing it! He-

As he had mostly cleared the fence into the Meyer’s backyard, the cuff of his right costume leg hooked on one of the sharpened fence posts. Quickly, his whole world went sideways, and he soon found himself slamming upside down into the Meyer’s side of the fence, the wind knocked out of him and thoroughly unconscious.

***

Richie didn’t know how long it was before he came to, but it couldn’t have been long. The flimsy material of his bodysuit hadn’t held with him hanging upside down on the fence, and he lay now on his back in a flower bed. His bag lay beside him, spilled open with toilet paper and broken eggs, and his costume was a complete loss, with the tear in its ankle having ripped all the way up to his crotch, the leg now flapping next to him. The flashing light of a backyard motion sensor light brought him to some form of reality, Richie tried to sit up.

He wasn’t quick enough.

“Son of a bitch,” the woman said, her voice about as angry as Richie had heard anyone be.

Knowing where he was, Richie knew who it was right away, not that it improved his situation any. A friend of his mom’s, Richie knew Emily Zhang-Meter to not be a very imposing woman. At barely over five feet tall and 120 pounds, Richie dwarfed her most of the time. However, sitting in her backyard, dazed and with her standing over him, she looked like a giant to him.

A pretty woman of Chinese descent, her beautiful face looked considerably younger than her 40 years. She had sort of dressed up for Halloween, wearing a short, black cocktail dress and a pair of cat ears, a tail pinned to the back of the dress. Though her big brown eyes were pissed and her soft, pouty lips were pulled into a vicious sneer, Richie’s eyes were pulled to what the cocktail dress showed, namely her wide hips, round ass, and utterly enormous tits. Richie had only ever seen her in the context of being his mom’s friend, wearing professional or mom clothes that weren’t the most flattering.

He found he preferred this view of her, even though she seemed considerably less fond of him.

“Richie!” she yelled with recognition. “What! The! Fuck! Seriously, what the fuck are you doing in my backyard, to my flowers… and are those eggs?”

The way she swayed slightly on her feet and her words had a slight slur to them, Richie imagined that she might have had a couple of cocktails tonight. He could now faintly recall hearing his mom in a conversation that Mrs. Zhang-Meyer’s husband took their kids out of town for the holiday to visit his family, while she was stuck here due to a business concern. By the look of her, she might have been having her own one-woman Halloween party between handing out candy to trick-or-treaters.

Thinking hard about the best possible response to the tipsy MILF standing above him, Richie said, “It’s… not what it looks like?”

“The fuck does it look like, then?” she demanded, her voice so full of anger that Richie practically expected steam to be pouring from her ears.

“I… don’t have a good answer for that,” he admitted.

Mrs. Zhang-Meyer rubbed the bridge of her nose, then looked over her shoulder. “I’ve heard sirens. Let me guess, that’s because of you?”

When he didn’t come up with a lie quickly enough, she spat, “Get the fuck inside. We’re going to have a talk about this.”

Richie gulped. Though he could have gotten out of most of the trouble if he’d actually been caught by the cops, getting caught by one of his mom’s friends was a whole different kind of trouble entirely. This… this could be hell. He could have tried running some more, made it into the next backyard, but that wasn’t going to help this time. Mrs. Zhang-Meyer knew who he was, and she wasn’t going to let him get away that easily.

Knowing he had to take a little of his medicine here if he wanted to get out of this, he followed her into the house.

“So, what have you been doing? Fucking shit up for a few laughs?” she asked, spiteful, looking back at him briefly before she opened the back door.

“Nothing… too bad,” he admitted. “Just throwing some eggs and TP, maybe filled a few jack-o-lanterns with firecrackers. It’s no big deal.”

“No big deal for little shits like you, but for people who take pride in their Halloween and have to clean all this shit up afterward, it’s a big fucking deal. You’re lucky my husband and kids are out of town, they practically live for this holiday; they’d have ripped you limb from limb if they thought you were gonna fuck it up for them,” she said, angrily.

Having never seen this side of Mrs. Zhang-Meyer before (cursing and reasonably undressed), Richie had a hard time fighting an erection. She may have been pissed, and threatening him with trouble, but damn if she wasn’t hotter than hell.

They stepped inside the kitchen, and though he couldn’t take his eyes off her swaying ass in her short, black dress, he was still nervous, especially when she turned around.

“You know, I’ve got half a mind to just wave down the cops out there and hand you to them. Maybe that way you’ll learn a fucking lesson for once,” she growled. Mrs. Zhang-Meyer ran a hand through her hair in annoyance, shifting her dress enough to give him an amazing view of her deep, deep cleavage. He might have stared a little too long, because she caught him quickly.

“Are you leering at me?” she demanded.

“No!” Richie lied.

“You little asshole… I take you into my home, and you’re fucking leering at me?” she said, looking him up and down. Though she still looked pissed, Richie caught something in Mrs. Zhang-Meyer’s manner that seemed… strangely softened. It was hard to say what for sure, but there was something in her slightly tipsy eyes that felt… promising.

“I don’t know what you want me to say, or do… just, please don’t tell my mom?” he asked, hopeful that they might be able to clear this up in time for the street to be clear of police cars.

“If there’s something you need to say, it needs to be better than that,” she said, looking him up and down again. “And if you’re gonna do something, you better take off that dirty costume, right now. You’re fucking tracking dirt into my house, and don’t you fucking dare expect me to clean up your goddamn mess!”

Richie looked at her, wondering if she was serious about him stripping off his dirty and torn costume. Again, she looked at him with a certain curiosity hiding amidst the fury, enough that he was willing to see where this went. Finding a corner near the door, Richie removed his shoes and socks, then pulled off his ski mask and set it down atop them. Without taking her eyes off of him, Mrs. Zhang-Meyer backed up and sat on a stool at the kitchen island, watching him disrobe. A glass of wine was already on the island, and she took it into her hand, taking a long sip as she watched.

Delicately, Richie removed the stretchy material of his bodysuit, pulling it off his muscular, toned frame and setting it aside with the rest of his clothes. As a frequent visitor to the gym and a star on the school’s track team, Richie was quite proud of his well-defined, lean muscles, including an impressive six pack and pecs. Though he was somewhat nervous standing in only his boxers in front of a woman he’d known much of his life, he did take a certain pride in the kind of reaction he got out of her. Especially when she was looking down at his boxers, and the erection straining to break free.

“Is this some kind of fucking joke to you?” she asked.

“I don’t know what you mean,” Richie replied.

“When I said take off your costume, I meant take it *all* off,” Mrs. Zhang-Meyer said, her voice somewhere between furious and playful. “Do you want me to call the fucking cops over here and tell them I got their man?”

Now, at heart, Richie considered himself a man with reasonable expectations, and by those reasonable expectations, he knew that there were about a million ways for her request to go bad, and maybe one where it would go well. However, when the way it could go well was as good as this one could go… he thought it better to err on the side of “fuck it” and did as he was told. He hooked his thumbs into the elastic of his boxers and pulled them off, leaving him naked in front of his mom’s friend.

“My, my, my…” she said, taking in a quick, short breath as she took in his thick, nine and a half inch long, cock. “I bet you’re popular with the girls, aren’t you?”

“Pretty damn popular, Mrs. Zhang-Meyer,” he said, cocky and proud.

“You’re standing naked in my kitchen, Richie; call me Emily,” she said, unable to peel her eyes from his cock. Her breathing had gotten heavier, and Richie saw with some pride that she licked her lips.

“Then, yeah, the girls fucking love me, Emily,” he said, still quite cocky and even prouder.

Emily sneered at his confidence. “Your mother was always an arrogant bitch too.”

“Probably why you two are such good friends, isn’t it?” Richie shot back.

She barked a short laugh. “You’re probably right about that.”

“So…” Richie said, deciding to take a gamble as he flexed his muscles slightly. “You’re not really going to call the cops on me, are you?”

“That depends,” she said, thoughtfully setting down her glass of wine.

“On what?” he asked.

Emily sighed, then parted her legs slightly on the stool. “Look, Richie, I’ve been the primary breadwinner and the most responsible parent for four kids under the age of fifteen since… well, pretty much forever. I haven’t had a lot of time to be foolish and stupid.”

“Not enough time for mischief and mayhem?” he said, raising an eyebrow. She was speaking his language now.

“Exactly,” she said. “Exactly… I thought tonight would be boring, paperwork, handing out candy, drinking, and then you fell into my yard. I’m still fucking pissed about that, by the way… but if you get down on your knees and eat my pussy well enough to make me cum, and I mean cum *hard*, then I might be convinced not to call the cops in on you.”

Now, when it came to porn, Richie had long considered himself a connoisseur of the genre and its many intricacies. At the same time, he also firmly understood that it was incredibly fake and heavily choreographed, and situations like these never happened in real life.

He also understood that in those one in a million chances when they did occur, that you fucking jump in and have fun, lest you regret *everything* later.

So, when Emily asked him to kneel, he knelt. When she motioned for him to crawl over to her, he did exactly that. When she pulled up her short skirt and showed him the lacy black panties she wore, he licked his lips in anticipation.

When she pulled them to the side and revealed her full, moist pussy lips and the dark, well-trimmed hair above them, he knew exactly what to do. Richie dove in, eagerly licking her pussy, searching her folds for what really got her going before he settled in suckling at her clit. She tasted different from all the high school girls he’d been with, but still sweet, still savory in a very distinct way. He had never been with an older woman before, let alone one who was friends with his mom, and he was going to enjoy every minute of the naughty encounter.

Emily seemed to agree with much of this philosophy, grabbing his hair and holding him in close while she groaned and cursed. “You always were a little asshole, Richie, getting everything you fucking wanted because your parents spoil you fucking rotten, well not now, now you’re here to fucking serve me… down on your knees is where you fucking belong like this… fuck… you really know how to eat cunt.”

Richie smiled into her pussy at the compliment. Though he may have been a bit of a lothario, he’d gone out of his way to learn as many tricks to please a woman as he could. After all, it wouldn’t do if every girl told every other girl that you were shit in bed, right? No, Richie sought to be good at what he did to keep the fun times rolling in, and those skills came in handy with Emily.

“Yeah, you like that, don’t you?” she moaned, keeping one hand in her hair while running another up her chest to grope her tits. “You like being my little pussy eater, don’t you?”

Coming up for air, he said, “I like a lot of things.”

“Did I say you could stop?” Emily said, forcing his face back into her pussy. “No… I’m still not fully settled on the police thing… keep eating me, like that… fuuuuuuuuck… so good, that’s so good, that’s it, just like that… play with my clit, fuck, it’s been so long… fuck you’re good at this…”

“I know,” he said, smirking and continuing to eat her out. Emily was different from the girls he’d been with before, she liked it slower and more methodical, and seemed to be enjoying her position of authority almost as much as she loved his attentions. He adjusted accordingly, slowing his technique and focusing on eating her out to not just her instructions, but also to how her body responded to him. By this simple adjustment, he found that she was soon quieting, her body tensing as she could only whisper encouragement.

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