Keep It Casual


All of the following is complete and total fiction. Not a single word of it occurred, nor would it.

Keep It Casual starring Demi Lovato

by MaxwellLord

(MF, oral, anal, exhib, cons)


It was Halloween night and Jesse could not think of place he could both rather be and rather not be at the exact same time. And it was all because of a dating app.

He'd had several installed on his phone, many against his will. Maybe one day he'd actually put a password on his phone. It was either that or have less jackass friends. Sure, it began harmless. It wasn't like he got any responses...until now.

The app was one where you had to be picked by the other person specifically. You didn't know who it was. An ultimate blind date app, at least for one half of the equation. Whoever this woman was, she chose him. She knew exactly who he was, which was how this was all going to go down, her seeing him. The ball wasn't just out of his court, but out of his entire stadium.

An app, a random woman's choice, and now he was here, waiting at a damn convenience store of all places for the date...or hook-up...whatever it was. The app was apparently meant more for casual sex than anything else. Jesse was used to not being 100% sure what was going on in his own life, but this was ridiculous. He hadn't been waiting too long, but ten minutes in the store nursing a slushy made him feel like he was a pimply high school kid all over again, minus the screamo band t-shirt.

That was the weird thing about the date, the woman told him to be dressed Halloween proper, whatever the Hell that meant. It's not like he had to scramble, he still had the stuff needed to make his Jay from Jay & Silent Bob costume he did every year work. The fact that he was just hanging around in a convenience store doing nothing dressed as someone who did that as a living was at least a little funny for him.

"Five more minutes," he said to himself. "Then I'm gone." Then, as if the god of happenstance heard him, the doors to the store dinged as they opened and in walked a crew of insanely hot women. One in particular stood out, dressed as a sexy S&M cop with an ass that didn't just not quit, but had no idea what the word meant. Her face was instantly familiar to Jesse. That face along with the entire package belonged to Demi Lovato. A small flicker of hope ignited in Jesse, one that he quickly put out.

"No, couldn't be," he assured himself. "No fucking way." And again, that wacky god of happenstance stepped in as Demi caught site of Jesse. She recognized him. "Oh dear God." he said to himself. His instant look of nervousness and disbelief made her laugh. Her saw her say something to her friends then headed towards him.

"Jesse, right?" Demi asked. She had backed him into the cooler, a predator to her hapless prey.

"Y-yeah...and you're..."

"Demi Lovato, yeah. Thanks for being stunned by the way. Lets me know the costume did it's job."

"Oh, it's not just the outfit."

"Thanks," she laughed. "Nice Jay outfit. We kind of match. You're the criminal, and I'm the one who catches you."

"Well, I surrender," he joked, getting a smile from her as she licked her lips.

"You bet your ass you do." She grabbed his cock through his pants, losing the space between them. "We're gonna fuck. I saw you on the app, thought you looked good for it. We're going to go behind the store, through that exit over there...and we're going to fuck."

"B-but what about your..."

"My friends think I'm going to the restroom. We have time." She began to unzip his pants, snaking her hand in once it was down. "You're nervous...that's cute. I like it. And you're packing. I REALLY like that." She winked at him then led him, her hand on his dick, through the exit.

Once they were outside Demi pushed Jesse against the dirty brick wall. She kissed him hard, her tongue in his mouth. She licked at his lips as the kiss broke, the look in her eyes brimming over with confident sexual heat.

"I've felt it in my hand, but now I think I need to see that cock." Demi squatted before him, level with Jesse's packaged. She deftly undid his belt and tugged his baggy pants down to his ankles, letting his cock spring free.

"Mmm, very nice," she said. She wasn't even touching him, but just the visual of Demi Lovato mere inches from his cock was enough to complete the job her hand had done, Jesse's cock was rock hard. He moaned a bit as she raked her nails up his thighs. The teasing sensations continued as her hands cupped his balls, lightly caressing them with her nails before her hand almost glided to his cock, softly jacking it with one hand while the other still fondled his full nuts.

"I think you're ready," she winked. Demi closed her lips around Jesse's cock-head, giving it something akin to a big, wet French kiss. That action alone made Jesse's eyes roll into the back of his skull. And that was just the beginning. Soon Demi had taken his entire length in her hot, wet mouth, wasting no time in building up a tantalizing rhythm in tandem with her snaking tongue.

While her mouth and hand worked in tandem, an erotically charged piston of pleasure while her other hand tugged and massaged his balls. If there was any mercy to be shown in a blowjob, Demi had no intention of showing it and Jesse sure as shit had no intention of asking for it.

Demi removed his cock from her mouth, moving to his balls. She extended her long tongue and began licking from his sack to the tip of his cock, planting another wet kiss on the head before rising to her feet.

"Time for part two." Demi smirked, then pulled Jesse close, kissing him as she switched positions with him. Her brown eyes locked on his as she reached between her legs, undoing a snap opening in the crotch of her bodysuit. Demi's hand then darted to Jesse's cock and grasped it, rubbing the head of his dick against her pussy lip.

"Mmm, do you want to fuck me Jesse?" Demi asked, her voice raspy.

"Uh huh..." he said, surprised he could even reply with that much coherency.

"What was that? I only fuck men who can form complete sentences." Demi smiled wide. She knew she could do or say whatever she wanted at this point. In a matter of minutes, he was 100% hers and she loved it. It made her even wetter than she already was.

"Yes...fuck yes I want to fuck you!" Jesse replied. He grabbed Demi's bountiful ass, making the leather clad sex freak laugh as she was picked up and pinned to the wall.

Demi grabbed his face and pressed her lips to his as he filled her cunt up with one thrust. He drew back and slammed into her again. Hard and fast was the order of the day, and Jesse had no issue serving it up the way Demi demanded. And Demi had no issue showing her appreciation.

"Ohhh oh fuck that tight pussy...fuck it..fuck it with that big fucking cock!" she yelled. She squeezed and flexed her cunt around Jesse's cock, making each thrust new, unique, and another dent in his endurance. She grinned like a woman possessed as she saw each thrust bring him closer to a climax he desperately needed but didn't want just yes and moaned like a woman lost in the moment, every thrust also bringing her closer and closer to an amazing crescendo.

Needing to taste more of Demi's lusciously thick body, Jesse took the zipper on her bodysuit between his teeth and pulled it down. With that obstacle out of his way, Jesse got to fully experience what he always thought was an underrated part of Demi's anatomy, her perky tits.

"Mmm, suck those titties," purred Demi. "Suck 'em." Demi hissed in pleasure, her lips pursed in a kiss as Jesse massaged and sucked on her tits, What began as a massage turned into a lustful maul, much to Demi's intense pleasure. Lips, tongue, teeth and fingers, teasing, nibbling, pinching; all the sensations on her tits along with the cocks filling her pussy made Demi tingled with pleasure, goose pimples all over her flesh.

"Ready for the real fun?" Demi said. "Because it does get better than this, baby." She pulled his mouth to her, sucking his tongue as Jesse set her down and pulled out. Demi gave him a wink then spun around and bent over. Her back arched to make her amazing ass look even more appetizing. "Three words...fuck my ass. Oh, and Happy Halloween."

"Oh...Happy Halloween indeed," Jesse said, gasping in happy disbelief as he stared at what considered to be the greatest ass in existence, waiting for him to experience it, right in front of him. He knelt down behind Demi, his hands rubbing and massaging her phat booty before burying his face in it.

"Oooh, we have ourselves an ass man," Demi laughed and moaned. "Mmm..b-big...surprise...ooooh fuck yes...I love ass men." Demi moaned more, loving the feeling of her ass being worshiped.

Her cheeks being massaged as her starfish was licked and probed with Jesse's tongue. It felt so good, but she knew it was just a teaser for something much bigger and better. The moment Jesse stood up, Demi knew that bigger and better thing was coming.

Demi braced herself against the wall as Jesse pressed his slick cock against her tight backdoor. With a slight bit of resistance at first, Jesse moved into Demi's asshole with ease. It was a tight, snug and amazing fit, but Demi had taken up the ass enough to know how to take a cock with ease.

"Mmmm...fuck that thing feels even bigger up my ass," Demi said, her voice happily dick drunk. "Don't waste time baby...fuck my ass...make me cum with that big fucking cock up my ass."

"Oh fuck," was Jesse's only response. Not that anyone, Demi included, could blame him. This was pretty much a fantasy fulfilled for so many men around the world, Jesse included. Being balls deep in Demi Lovato was not something he ever expected to happen, let alone behind a convenience store while she's dressed as a slutty S&M cop. All things considered, as much as the lustful side of his brain screamed to slam her ass, he fought the urge, savoring every moment he had his cock up her backside.

Demi tried to contain her moans, but with every thrust Jesse made, they got higher and louder in pitch. The struggle against herself was all part of the thrill to her, the sizzle on the steak. She couldn't hold back a yelp when Jesse slapped her ass. She loved that, she loved when men slapped her ass during sex. She understood why they needed to do it...she knew she had an amazing ass. She'd smack it too.

"Do it again," she said. "Slap my ass!"

SMACK! Jesse geared back and did it again. "MORE!" SMACK! Another one in reply. Jesse leaned forward and pressed his mouth to Demi's neck, licking her while his arms wrapped around her.

"Mmmm...yeah baby...oh fuck your cock feels so good in my ass...ooohhh don't stop...don't...fucking...uh..uh...stop..."

He pulled her up, her back to his chest and began driving into her as fast as he could, both of them moaning loudly into the night, lost in the moment. His hands were at his breasts, cupping and kneading them while his cock hammered at Demi's ass. Jesse nearly got weak in the knees when Demi squeezed her ass tight. She looked over her shoulder at him, a sexy little sneer on her face before their lips met in a sloppy kiss once more.

Soon, painfully, soon, all the activity took it's toll on both of them. Demi leaned back over, bracing against the wall once more as Jesse got closer and closer to his orgasm. SHE couldn't wait to feel it, his cock pulse in her well fucked asshole, the cum filling her up...she loved it. It felt so dirty but so right. And it always made her cum. Always.

"Oh FUUUUCK!," Jesse growled, thrusting on more time, to the hilt, in Demi's asshole.

"Yessssss baby," she hissed, already feeling her orgasm ready to explode when the first stream of Jesse's cum filled her bowels.

"Oh fuck baby keeping my ass!" Demi moaned right as she started to cum. Jesse complied,thrusting through his own orgasm, making him shiver and shake from the intensity of it all. Intensity that only increased as Demi's asshole clamped down on his cock, forcing out the last few streams of cum he had to give.

"Oh fuck that was amazing," Demi said, a gigantic grin on her face. Jesse pulled out, sweaty, wrecked, and utterly out of breath. Demi turned around, satisfied in every single way, laughing a bit as she saw Jesse every bit as satisfied as well. "Now that's what I call trick or treating."

"Yeah." a very dazed Jesse replied. With the grace of a drunk half a fifth deep, he tugged his pants back up. Demi walked up to him, giving him one last kiss on the lips.

"That was great," she said. "I mean that. Takes a lot to get what you're about to get." She reached down to her boot and took out a card. It simply said "DDL" and had a phone number beneath it. "Next time you want to have some fun like this, give that number a call, sweet face. Just remember, keep it casual. It's all I want right now."

"Yeah...definitely...fucking definitely."

"Good. Until then...happy Halloween."

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