Once Upon a Halloween Ch. 05

When he heard Emily's friend send her children to the sidewalk a distance away so "the adults could talk for a few minutes", Richie felt an opportunity for further fun was in order.

While Emily and her bitchy-sounding friend talked about neighborhood gossip (and the friend questioned why Emily looked a mess), Richie reached up underneath the back of her short dress and squeezed her ass. She hadn't put her underwear back on, giving him free access to her luscious cheeks as he first massaged each, then ran his middle finger down the center. He massaged, gently, her tight little asshole, enjoying the look on her face as she tried to hide her anger and arousal while talking about neighborhood banalities as if nothing was wrong. Even so, she arched back onto him, and he felt her ass open up, and, well, when opportunity knocks...

With only a little effort, he pressed his middle finger inside her asshole. He couldn't reach into her much from this angle, but it was the act that counted, as he fucked it into her for close to a minute while Emily tried to quickly wrap things up with her friend. Finally, she was able to wrap the conversation up, and the moment the door was closed and locked, she turned hard, pulling his hand from her ass as she looked up at him furiously.

"I told you to stay in bed," Emily said, eyes blazing.

"Yeah, you did, didn't you?" Richie replied with a smirk.

Though it looked like she wanted to slap him, instead she grabbed his head and pulled him in close. The two of them kissed fiercely as he pinned her to the wall next to the door, hoisting her up just enough so he could bury his cock deep in her pussy once again. Pulling down the top of her dress to better see her tits, he fucked her against the wall, hard, grunting and kissing. Sex with Emily was unlike anything Richie had ever experienced, and it was quickly becoming a drug to him. He never in his life would have expected the best fuck he had ever had in his life would have been because of one of his mom's best friends, but good sex was good sex, and he wasn't going to turn down an opportunity like this if it kept presenting itself.

"You gonna cum for me again? I know you were close, you gonna cum in my tight little cunt again you little sonofabitch?" Emily moaned, squeezing her nipples and biting her lip as she looked up at him lustfully.

He smiled with some pride. "Yeah? You like the thought of getting knocked up by your friend's son while you cheat on your husband?"

She groaned from deep within, her eyes rolling back with pleasure before turning to him again. "God... it sounds so awful, and so amazing... I'm always so fucking horny when I'm pregnant, and while I hate a lot that comes with it, the sex... god, the sex even with my husband is amazing then, and with you around... fuck, you little shit, you better fill me up nice and deep and get me knocked up, because once I'm pregnant I'm going to show you what real fucking is."

He liked that promise, and rather than come up with something witty in response, he fucked her against the wall harder. His balls boiled, his cock throbbed, and when he felt the need to cut loose, he didn't hold back in the slightest. Pleasure overwhelming his body, Richie came inside of Emily, setting off her own orgasm as the two of them fought to stay standing. He filled her deep with an impossibly thick load, feeling his whole body overcome with pleasure and joy as he slowed and thrust his final thrusts into her.

He pulled out of her, watching the small river of his cum leak down her legs as she collapsed to her knees. Richie worried Emily might have passed out for a moment, but kneeling there she simply attacked his cock, licking and sucking and jacking, massaging his balls and trying to get him hard once again. She was a ravenous animal, a beast come from the darkness of Halloween, but when it felt this good that hardly mattered. She looked up at him hungrily, needily, her eyes having none of that edge that she'd had for the entire night and only holding want.

Richie was hard again in no time, and at that, she rotated on her knees so her hands were against the door.

"There's one more thing I want from you," she said, reaching back and pulling her short skirt over her ass.

"Oh yeah, and what's that?" Richie asked.

"I think you know," Emily replied, flexing her ass and squeezing her asshole for his hungry eyes. "My husband never wants to play with my ass, but I don't think you're held back by such hang-ups, are you?"

Richie barely needed to think before kneeling down behind her and answering, "Nope!"

He lined up his cock, rubbing his lubed-up head over her asshole and enjoying the feeling as her cheeks embraced him.

"Good... now, be a good little asshole, and show me what you can do with mine," Emily groaned, arching her back so she could kiss him.

"You got it," Richie answered, kissing her and forcing his cockhead against her tightest entrance.

He pressed in hard, her saliva and his precum offering a fair bit of lubrication, but nevertheless he was trying to fuck an ass that hadn't been fucked in a very long time. No matter how much Emily demanded it or how much he wanted it, it was tough going as he grunted and thrust, and she moaned and pleaded, looking back at him as he tried to fuck into her. It was not easy, but he knew it would be worth it when he succeeded.

Soon enough, Emily's asshole opened for him, and though she was almost so tight it hurt as much as it felt good, he felt his cockhead pop inside of her.

"MOTHERFUCKER!" she cried out, pounding on the door so hard and screaming so loud someone might well have thought the house to be haunted.

"Yeah, that's what I am right now," Richie grunted, forcing more of his cock into her ass. He knew he should have gone slow, that it had been a while for her, but he wanted this ass, and she wasn't fighting with him. Emily just looked over her shoulder at him with the hottest look in her eyes that Richie had ever seen, biting her lip and whining through the pain as he fed inch after inch of his huge cock into her.

It had only started to hit him again how different this night had turned out than when he had started it. It was supposed to be him and Lucas, showing this town who its true kings were while they got into some Halloween fun. It was going to be a night of freedom, liberty and mayhem, and then it had almost fallen apart when the cops had chased them.

Forcing the last of his cock in until he was buried in her ass, Richie smiled. From getting chased by the cops to being balls deep in the ass of one of the hottest MILFs in town, it was one hell of an improvement. The best sex of his life with this tight Asian minx, filling her holes and knocking her up... Instead of wondering what he was going to tell his parents when they freed him from the cops, he was wondering just what sounds Emily would make as he railed her ass, and whether he should cum inside of her or pull out and shoot all over her face and immaculate tits.

Why pick, honestly, when they had the whole night ahead of them?

Leaning down, he grabbed her tits and kissed her, whispering, "Happy Halloween."

Emily smiled into his kiss, then reached back with one hand to smack his ass. "Enough of this Halloween bullshit, asshole... you're gonna fuck my ass until I scream."

He thrust into her roughly, driving her into the door. "Such a needy cunt."

"Motherfucker," she grunted, her voice getting higher and louder as he started to fuck her ass hard. "Oh, GOD, YES! HAAAAPPPYYYY HALLOWEEEEEEEEEEEEEEEN!!!!!!!!"

"Happy Halloween, slut," he groaned, leaning in to kiss her again.

***

(Author's Note 2: Writing this story is something I do in my spare time for fun, so if you're enjoying this, please, please, please drop some stars, reviews or shoot me some feedback, as they really keep me going. Though I may not always respond, I do love hearing from all of you and seeing that you're enjoying the series. It motivates me to continue writing more. You've all been wonderful and I can't thank you enough for all of your kind words and encouragement and yes, even the constructive criticisms!

And after some recent crises and battles, I want to add one last note on a more practical concern. When it comes to mental health, I hope everyone out there is taking the time to take care of themselves. Mental health may seem like a never-ending battle, but it's a never-ending battle that is always worth fighting, and one that there are plenty of resources to be found to help with should you ever be struggling. Be good to yourselves, and to everyone else.)