Once Upon a Halloween Ch. 03

"While that's... fucking awesome," June said, her voice high and fluttery as he pleasured her, "I want your tongue somewhere else."

Pulling his mouth from her cunt, Sean asked, "Where?"

June flexed her ass at him again, drawing attention to her tight, pink asshole. "Where do you think?"

Sean gulped. He'd done a fair bit when he was with Anna, but he'd never licked a girl's ass before. There was something about it that still felt, well, dirty, but there was no denying that it was also impossibly enticing. He'd already done a fair bit with June already, how was this any different? And yet, it still felt strangely taboo.

June read his hesitance and growled at him, "Eat my fucking ass, Sean and finger my pussy until I cum, and if you do it good enough, I'll let you fuck my ass."

Sean's eyes went wide. If he hadn't eaten a girl's ass, he'd certainly never fucked one before. Only slightly hesitant, he adjusted his aim and dove in, suckling and licking at her asshole.

"Mmm, yeah, that's it, right there... I bet Little Miss Anna never let you do anything with her ass like this, right? Well, I love having my ass played with. Lick it, kiss it, fuck it, do whatever you want with it so long as you keep doing it that well," June groaned, reaching down to finger her clit while he ate her ass.

It was a strange position for him to be in, and while the act may have felt a little wrong at first, he soon found there was nothing wrong with eating June's ass. It may have tasted different, but worshipping her tightest, most forbidden hole was strangely enticing, and the way it made June moan and shake more than made up for any discomfort on his end. Sliding a couple fingers into her pussy, he fucked her with them in time with her own efforts on her clit, thrusting into her while he licked her asshole in tight circles.

She purred, her voice weak as she moaned, "Ooooh, fuck... that's so good, so fucking dirty... you thought you needed a nice girl, a good girl, but what you really needed a good girl who knows how to get down and fucking nasty, and trust me Sean, I can get fucking dirty... stick around and we can do some nasty fucking stuff..."

That brought up a question he hadn't considered. They had been fooling around for a fair bit now in the projection room, and while it had been amazing, Sean had never considered what was going to happen once they left this room. Was this a fling where they'd go back to how things were once they were clothed and out of this room? Did June expect a relationship out of this? Was he ready for another relationship? These were big questions to consider when he had his face buried in the hottest ass he'd ever seen, and they weren't ones he felt qualified to properly answer.

"Like that, like that," she instructed as he applied more force with his tongue to her hole. "Keep going, fuck me with your tongue, fuck my tight fucking ass with your tongue..."

Sean realized that those were also questions best left for later, and that he should do what he set out to do. Straightening his tongue out, he pushed against June's asshole hard. It took a lot of force, a lot of grunting from her, but finally he broke through, thrusting his tongue into her asshole.

"OH MY GOD, FUCKING HELL!" June cried out, cumming hard as he broke in. Her asshole tightened around his tongue as her pussy did around his fingers, but only her pussy gushed and soaked his hand. She shook and cursed until all strength left her body and she collapsed facedown on the couch.

Weakly, she turned around, her eyes full of pure, unadulterated lust as she pulled Sean in and kissed him. She sucked on his tongue, his tongue that had just been inside of her ass, with some delicious, naughty glee, before parting and smiling. Without a word, she also took the hand he'd been fucking her with and sucked his fingers into her mouth, cleaning them with lidded over eyes.

"Fuck, I taste good," she groaned.

"Yeah, you do," he replied, kissing her and savoring her flavor on her lips.

June kissed him back needily, pulling him closer to her and crushing her tits against his chest. She reached down and felt that Sean was both hard and leaking precum again, and sliding to the edge of the couch, she lined him up with her pussy and guided him inside again. Kneeling on the floor while she sat on the couch, Sean fucked her like this slowly, grunting softly while June occasionally made pleasurable mewling sounds and the two exchanged long, lingering kisses and gropes.

"I... fuck, I need this in my ass... I need you to fuck my ass sooooo bad," June said, looking up at Sean with her big, expressive eyes. "Will you fuck my ass, Sean... please?"

There were some questions in life that didn't need to be asked with that kind of insistence, but it didn't hurt to hear the request put so nicely, either.

Grunting, continuing to thrust into her, he said, "Yeah. I'd like that."

"Good!" she replied brightly, kissing him and pushing him out of her. Quickly, she went to her discarded purse and explained, "Now, you've never fucked a girl in the ass before, have you?"

"No," Sean admitted, a little embarrassed.

"Makes sense. I wouldn't have thought Anna would be up for that, by the sounds of her," June said, pulling a small bottle of KY from the purse and smiling. "Well, a quick lesson, then. When it comes to a good, hard, assfuck, lube is the difference between a bad time and a very good time, and if we want to make this fun, we're really going to need to lube that monster up."

"I understand. Pass me the bottle?" Sean asked.

"Yeah, I love the enthusiasm, but I've got a better idea for how we can apply it to you," she said, upending the bottle and pouring it on her tits, working it into her cleavage before she put the bottle aside.

"Oh, I'm going to like where this is going, aren't I?" Sean asked.

"You bet! Now sit on the couch," June replied, watching as he did before first, bending down to kiss him, and then kneeling between his legs. "Fuck, this is an amazing cock... I might have to keep you."

"Not if I keep you first," Sean replied, looking on in awe as June massaged her massive, oiled-up tits.

"Yeah? You think we could make a thing of this?" she said, leaning in and wrapping her lubed tits around his cock. Sean moaned at the heavenly sensations as his cock was wrapped up in her massive breasts, the sight of the head disappearing in and out of the valley of her cleavage feeling fucking insane as she tittyfucked him vigorously.

"A thing of tittyfucking, or, us?" he asked.

June thought about this, but stopped meeting his gaze. "Dealer's choice?"

Though it was hard to argue with a huge-titted girl who was tittyfucking him so well, Sean thought it best to let cooler heads prevail. "Can we talk about this when we're less horny? I think that might be best."

"Right," she replied. "Sorry, I can get a little crazy when I'm horny."

"Don't we all?" he answered, groaning.

June laughed, squeezing her tits harder around his cock as she bounced them up and down. "You'd be surprised. Some guys, they look at this and just go at it like they're on a mission. Not a hint of passion."

For all of her teasing, Sean decided to turn the tables on her and asked, "I got them beat, don't I?"

"Handily," she said, pulling her tits from his cock and then quickly kissing the tip. "It's not every guy I let fuck my ass. You should feel special."

"I do," he said, watching attentively as she stood back up and turned around. Her magnificent ass was on full display and after shaking it from side to side briefly for his benefit, she slowly began to lower herself.

As an idea struck, he stopped her and said, "Wait."

"What?" she asked.

Standing up, Sean took her by the wrist and guided her over to the window where they could look out onto the theater.

"Don't you want to watch the rest of the movie?" Sean teased.

June raised an eyebrow at his suggestion. "You know what... I think I do."

Turning to face the window, June bent over at the waist and braced her hands against the wall. She jut her ass out toward him, flexing her cheeks enticingly as she showed him her tight asshole.

Sean grinned, a little nervously. "Good."

June looked back at him encouragingly. "You've never done this before, right?"

"No," Sean admitted, approaching her slowly.

"Don't stress," she said. Reaching back, she gently grabbed his cock and urged him forward until he was pressing up against her tight hole. "Just take it slow, and easy. It will take some force, and it might hurt me some, but I can take it. After that, then it'll feel really good for both of us."

Sean found it rather surreal to be in this position, June bent over, his cock about to penetrate her ass as they both looked out over the theater and watched Halloween. Below them was a reasonably full audience watching a masked killer stalking babysitters, and here they were only feet away about to get into some truly dirty fucking.

"Do it, Sean..." June urged, biting her lip as she looked back to him. "Fuck my ass."

With his cock lined up, Sean held his cock and pressed forward. June grunted and groaned, and though she talked like she was experienced with her ass, Sean doubted she'd been with any guy as big as him. Nevertheless, he pressed forward, rocking back and forth as her asshole first held firm, and then began to slowly open for the tip of his cock. With only a little more fucking, he felt her definitively open up for him, accepting more of the head.

"Almost, almost..." he grunted, savoring the tight embrace of what he could fit into her ass.

"You got this, just a little more, just a lit- FUCK!" June cried out, closing her eyes tightly when his cockhead finally entered her ass.

"Oh my god, ohmygod, hooooly fuck," he grunted slowly, looking down at the seemingly impossible sight of his cock disappearing into her ass. Never in a million years would he have expected to do this with anyone, and here he was, inside June's ass.

"Keep going," she whimpered. "Sooo fucking good..."

Beyond words himself, Sean continued forcing his cock into her impossibly tight ass. He had thought he'd known tightness before, but inching inside he began to understand that there was still much he had to learn. Her ass embraced him so firmly it quite hurt, but in that pain there was an undeniable burning pleasure deep within him. He needed to fill her, to claim her, and he pushed forward insistently to give her every last inch.

With every slight push forward, she squealed and moaned, reaching down with one hand to finger her clit as he filled her. When Sean had bottomed out in her ass, his balls resting against her pussy, she looked back at him and smiled weakly.

"That's... that's some awesome cock," she said, almost giggling from her giddiness.

Weakly, he replied, "Wow." Then he leaned down and kissed her. He held her close, his hands reaching around and squeezing her lubed-up tits as he rested buried in her ass for a moment.

It was not a moment that would last long. June grunted, "Come on, Sean, I told you I wanted you to fuck my ass and I need my ass fucked now!"

Chuckling, he grabbed her hips and replied, "So demanding."

"And you love it, don't you?" June challenged.

Pulling his cock most of the way out of her, Sean just as quickly slammed home, making her moan. "What do you think?"

"Fuuuuuck..." she moaned, bracing herself while Sean properly fucked her ass.

Pumping his cock into her ass hard, Sean felt well and truly good for the first time in what felt like a long time. He was happy with himself, and where he was, and couldn't have been happier for the company. He wasn't worried about his phone, or Anna, or missing out on the night, he was living in the moment with his cock buried up June Poole's ass, fucking her for everything she was worth. When she looked back at him, her face screwed up in the greatest look of passion and lust he'd ever seen on someone's face, Sean could only smile back at her and fuck her ass harder.

It was an unconventional approach to Halloween, he had to admit, but when in a matter of minutes she was cumming so loud he worried the audience might have heard her (thank god for an even louder sound system) and he filled her ass with his own cum while looking on at the horror classic, he realized he was not one to complain.

Still buried in her ass, he bent over to kiss her while she did everything to stay standing on wobbly legs.

"Happy Halloween, June," he whispered to her, smiling sweetly and kissing her again.

Smiling back and squeezing his cock with her ass, she said, "Happy Halloween, Sean. We should really get cleaned up and back to work."

"I know," he said, wrapping his arms around her and holding her close. "But can we stay like this a little longer, watch a little more of the movie?"

Smiling up at him sweetly, she kissed him again and said, "Sure."

Sean sighed pleasantly. Earlier today, he would have said this Halloween perfect was impossible. Thinking on how it ended up, he realized he'd never been happier to be wrong.

He grinned. "Happy Halloween."

***

(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.)