Bad Boy Road Trip Ch. 01

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Day One: Jake first score is a Family Affair.
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Part 1 of the 5 part series

Updated 06/08/2023
Created 04/26/2017
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Please enjoy this new story. It is a work of fiction, intended for adult readers. All characters are adults, eighteen or older, and unusually horny. Taylor VanCannon.

*****

Prologue

Jake drained the cold beer and slammed it down on the bar, drawing the bartender's attention. Without asking, he brought another longneck.

He looked over at his buddies playing pool. After sixty days on a West Texas oil rig they were flush with cash, and eager to party. The locals tolerated them, but would not cotton to losing their hard earned money to the rowdy hustlers. A bar fight was inevitable.

Jake was a lover, not a fighter. He gave his buddies a wide berth and scouted out greener pastures in the crowded Abilene honky-tonk saloon. It was Friday evening, and small groups took up tables around the dance floor.

A table of young ladies caught his eye, office workers ready to blow off a little steam on a Friday night. They were very attractive, hot in fact, and any other night he would have jumped at the chance to bed any one of them. But tonight, he was in the mood for someone a little more experienced... someone that could handle his equipment without a lot of drama. He was about to move on when a somewhat older woman, maybe early forties, joined the group. She was a little rough around the edges, much like himself. Her long red locks cascaded down her shoulders in a mass of thick curls.

When the younger girls got up for a line dance, he moved onto the dance floor and worked his way into their line. It didn't take long to strike up a conversation. He naturally attracted girls... especially those looking for something on the wild side. He had bad boy written all over him. One by one he raised their hopes, only to dash them by moving on to the next girl. Not ready to give up, one of them invited him over to the table.

The girls were aghast to see him focus his attention on Joan, their boss. They couldn't believe Jake would pass any one of them up for Joan.

Joan was amused, but wasn't interested. After all, she was married, and came to the bar as a courtesy to her employees.

A challenge to be sure, but one that Jake was up to; he'd done it many times before. Joan relented to one dance when a fast number came up.

She was grateful that he backed off and appeared to give up on scoring anything more than just a dance. She felt the tension flow out of her body and she began to actually enjoy dancing. To her surprise, he was a perfect gentleman, so she decided to stick around for a second dance.

The music slowed and he pulled her in close. His rugged body belied the grace he exhibited on the dance floor. He twirled her out for a slow spin and then pulled her back into him, tight.

His leg naturally fit between hers and he pressed it into her groin, sending a jolt of pleasure through her body. Uneasy, she was about to pull back when she felt pressure along her inner thigh. Momentarily confused, it slowly dawned on her that it was his cock, hanging down and pressing into her, like a long fat sausage. Her mind reeled as she tried to calculate how big it was... bigger than anything she'd ever encountered. She swooned, and stayed in tight as he guided her around the dance floor. She made no effort to push back when the music ended.

"I've got an RV parked outside," Jake whispered into her ear.

She fought hard to resist temptation... but couldn't get the image of his big cock out of her mind. She smiled and followed him out the back door.

He stood in front of the bed while she knelt and silently unbuckled his pants. She stared, unblinking, at the head of his cock, poking out from below the bottom of his shorts. He smiled down at her, patiently waiting for her to look back up.

She stood without speaking and gave him a peck on the lips. They maintained eye contact while peeling off their remaining clothes. She made the first move, cradling his soft cock with both hands. He replied with a tender squeeze of her breasts.

As his cock stiffened, it wedged up in the gap between her legs. She responded by moving her hips, painting his cock with the wet lips of her pussy. Her swollen clit protruded just enough to scrape over his cock, sending tiny jolts of pleasure though her body.

He knew exactly what she was up to, and encouraged her by pinching her hard nipples.

Her breathing quickened as her clit raked along the top edge of his monster cock.

He watched her orgasm blossom and take hold of her body.

She sucked in one last breath and bit down on her lower lip. Her legs started to buckle.

He grabbed her by the ass to keep her upright and pulled her in tight, keeping his firm cock pressed up into her gash, putting even more pressure on her clit.

Her eyes rolled back as wave after wave of pleasure coursed through her body.

He fell back onto the bed, bringing her with him.

She took several sharp gasps before her breathing returned to normal. She lifted her hips and let him guide his cock up into her very wet pussy. The monster filling her cunt was anti-climatic, compared to the intense orgasm she had just experience. She regained her composure and fucked him slowly, savoring each insertion of his big cock. "Happy?"

He grinned wildly, "Very."

She winked. "How do you want it?"

He licked his lips. "I like to watch?"

She sat up and furrowed her brow, unsure what he wanted.

He nodded down to her crotch.

Now she understood, and drew he knees up, keeping them closed. She leaned back and supported herself on her outstretched arms. It surprised her that his cock bent so easily to her new position. "Ready?"

He nodded enthusiastically.

She slowly open her legs, revealing her thick red muff penetrated by his cock. "You're very flexible... with your cock."

He hooked his thumbs under her thighs, close to her crotch, and slide her back until all but the head of his cock was visible.

She responded by thrusting her hips forward to take him back in. After several trips back and forth, she asked, "Can you cum like this?"

He nodded, but didn't push her back down his cock. "I want to watch you cum again."

She raised her eyebrows, asking how.

He responded by licking his thumb, and then rubbing her glistening pink gash, searching for her hard little nub.

"Good answer," she said, leaning her head back and tossing her hair from side to side in a flourish.

It didn't take long. If anything, the second time was even more powerful. She uttered a tiny squeak with each gasp for breath as her body convulsed under the onslaught of his thumb.

Sated, she sat upright on his cock and stared into his eyes. Eager to get him off, she asked cautiously, "How do you want to finish?"

He sensed her apprehension, but knew exactly what he wanted, "In your ass."

She took a deep sigh; she'd never done it before, even with a cock half his size.

He waited patiently, giving her time to adjust to his request. He was rewarded with a tentative nod. That was all he needed. He knew that despite its size, his erect cock remained flexible enough for most women to handle. He helped her spin on his cock so that she faced away from him.

She looked over her shoulder, scared, like a deer caught in the headlights.

He smile to reassure her and used his palms to spread her cheeks open. The view was amazing. Her tiny rosebud peeked out from a nest of tight red curls. He used a thumb to smear her slippery juices up into her ass crack, and then gently pressed it into her tight hole. Relaxed after two orgasms, it slipped in easily.

She lifted herself off his slippery cock and reached back to wrap her fingers around it. She rubbed the head of his wet cock along the crack of her ass until she felt it press against her asshole. She held it firmly while she let her weight drop down onto it, surprised that the head slipped in.

"Oh yeah," he said, "you're doing great... and the view is incredible."

Emboldened, she put a hand on the low ceiling and used it to force herself down, slowly, inch by inch, until his cock was all the way in. She looked over her shoulder, proud of her accomplishment.

He licked his lips. "Now, fuck me... fuck me hard."

She complied, using the ceiling for support as she rose and fell on his cock. The unexpected pleasure of having a cock up her ass left her wanting yet another orgasm. She bent forward until her tits were squashed into his legs. She reached for her clit and pumped her hips, furiously fucking him.

"Oh yeah back," he said, "just like that... get me off." His neck cramped from staring at the gorgeous view of his cock sliding in and out of her ass. He tilted his head back and closed his eyes, eager awaiting the inevitable.

He drew in a deep breath. "Oh fuck... I'm so close."

She froze, and screamed, "Don't shoot... Don't shoot."

"W-w-what?" It was too late, the first rope of cum was on its way.

She dove off the bed, leaving his cock spurting cum high into the air.

He lifted his head and opened his eyes, wide, and stared into to the business end of a Colt Peacemaker.

Day One

Jake woke the next morning, thankful to be alive. Any other husband would have pulled the trigger, but Joan's husband was a local Sheriff, a man who understood how to stay on the right side of the law. After a sizable contribution to the Police Youth Fund, in cash, and a strong suggestion to be out of the county by midnight, he made a late night dash west on I-20, to the town of Sweetwater, where he pulled into a Way-Mart parking lot for the night.

Still flush with cash, and a strong desire to be done with West Texas, he figured a road trip to California would be just the ticket. Traffic heading west on I-20 was light and he calculated he could make Van Horn by early afternoon. That would give him plenty of time to plan his trip and stock up on supplies.

Just outside of Westbrook, traffic slowed to a crawl. From the top of the overpass he saw multiple flashing lights ahead, a sure sign of an accident. It looked like all traffic was being diverted off the freeway. No big deal; he had plenty of time, and a few hours late wouldn't matter.

Jake merged right and threaded his way into the single line of cars exiting the freeway. In his left mirror, he saw a big pink caddie coming fast. The driver jammed on his brakes and swerved into the tiny space in front of him, almost plowing into the big rig in front of him. The caddie was old, maybe 1968, pink with a white interior, a convertible with the top down. The skinny driver sported a black cowboy hat. A woman in the passenger seat had long blond hair trailing out from under a rumpled brown cowboy hat, flying in the wind. Fucking idiot cowboys! He couldn't wait to get out of Texas.

Jake caught the driver looking back at him in his mirror, so he flipped him off. But the cowboy just gave him a friendly wave, and the woman turned back, shrugged her shoulders and gave him a wide smile. She was all Texas, and Jake could almost hear her drawl as she mouthed an apology

"Jeez Dwayne," Daisy said to her brother, "you could have killed us. What's the fucking hurry?"

"Wait a minute," Dwayne said, exasperated, "you're the one trying to catch a flight."

"So," Daisy said, "I miss out on a weekend with Jimmy... At least I'll still be alive."

Dwayne shook his head and checked his watch. They were cutting it close. The police directed traffic onto a narrow two lane road. It was stop and go, barely moving.

"Check the map," he said, "and see how far before we can get back on the freeway."

Daisy tapped on her phone to bring up the map app. "At least 15 miles," she said.

That could add two hours at this rate, there was no way Daisy would get there on time. "We're not going to make it," Dwayne said.

"Oh well," she replied, wistfully.

"I can tell you're broken up about it," he said, "what gives?"

"No big deal," she replied, "it wasn't going to last."

"Problems?" he asked.

"Wouldn't you like to know?" she replied, slightly annoyed.

"Come on Sis," he said, showing genuine interest, "I care about you. Tell me. I thought you liked Jimmy."

"Okay, you asked for it," she said, "he wasn't very good in the sack."

"Maybe your standards are too high," he managed to say between fits of laughter, "after all, I helped you set them."

"Cute," she replied, smacking him on the shoulder, "I'm sure that's what it is, you're just too damn good."

Dwayne leaned back and stretched his arm out on the seat back, patting Daisy on the shoulder. "Hey, I'm always here to help."

"In your dreams," Daisy replied, "besides, if I miss my flight it's going to fuck up your weekend too."

"Huh?"

"I know what you and Mom had planned," she replied, poking a finger at him, "just as soon as I was out of town."

"She told you?" he asked, surprised.

"No," she said, unable to contain her glee, "but you just did."

"Fuck!" Dwayne said with a wide grin, "I've had the beginning of a hard-on ever since we left the ranch."

Daisy glanced down and smiled when she saw the bulge in his pants. "Really? What did Mom promise you?"

"A blow job," he said, "just as soon as I got back."

"Too bad," Daisy said, "that's not going to happen now."

"You could fix that," he said, giving her a wicked grin.

"In your dreams," she said. Just the suggestion of sucking his cock triggered an itch between her legs, one that might need scratching. They hadn't fucked since she started dating Jimmy, more than six months ago. No matter how many guys she dated, none of them quite measured up to her brother.

"Come on," he pleaded, sensing her resolve was weakening.

She was tempted. Jimmy's tiny cock just didn't get the job done for her. But Dwayne's, that was another story. Unlike his skinny ass, his cock was big and fat, just the way she liked 'em.

"What about Mom," she said, toying with him, "If you can't get it up when we get home, she'll know it was me."

"She won't find out," Dwayne said, pulling her over close to him, "and I'll never tell."

She reached down and squeezed his cock. "Okay horn-dog, find some place to pull over, someplace private; I'll do it."

"Sweet," Dwayne said, "but, that will take too long in this traffic. Do it now."

Daisy looked around. There was a big truck in front of them, so nobody could see from that direction, and the oncoming traffic was light and moving too quickly to be able to see much of anything. She glanced back over her shoulder and took a quick look at the driver of the RV behind them. His eyes were masked by a pair of mirrored aviator sunglasses. "What about the guy in the RV? He's sitting up high and looking right down on us."

"What's he look like?" Dwayne asked.

Daisy looked back for a closer look. "Hard to tell, a little older than us, maybe late thirties, pretty good looking... for a redneck smoking a stogie."

Dwayne thought for a moment, "Sounds like a guy that might appreciate a good show." He pulled her in tight and let his hand drift down to her tit, giving it a firm squeeze.

"You'd love that," she said, "wouldn't you. Fucking show off."

Jake watched the couple not more than ten feet in front of him. It didn't take a rocket scientist to figure out what they were discussing. His cock stirred ever so slightly and strained against his pants. The girl looked down and fiddled with the driver's lap. Jake let out a low whistle. Oh yeah baby, just do it!

He watched her turn back and look him over for the third time. He tipped his cap and raised his mirrored sun glasses to stare back at her with his gunmetal blue eyes. She smiled and then rolled her eyes. What did that mean? He gave her a thumbs up... he definitely wanted to see more. She nodded, and then got to her knees, giving him one last look and licking her full, succulent lips. Her rumpled hat partially obscured her eyes, giving her a sultry look. He caught her wry grin just before her head dropped out of sight, into the drivers lap.

Oh yeah baby, suck that cock!

Daisy swirled her tongue around the head of her brother's hard cock, and then took him into her mouth. Her wet lips coated him with saliva as she took him further into her mouth.

Jake strained forward trying to get a view of her head in the driver's lap and gave his cock a firm squeeze. It wouldn't be long before he was hard.

Dwayne rolled his head back and enjoyed the gentle sucking his sister gave him. He reached over and caressed her ass, squeezing her cheeks, pressing his fingers into her crack.

Daisy moaned and wiggled her ass, then lifted her head and said, "Oh yeah Dwayne, I like that, slip a finger into me,"

Jake watched her black panties come into view as the driver pulled her dress up. When the dress was clear of her panties, his hand slipped under the waistband and into the crack of her ass. She lifted her head and kissed him on the lips. His fingers must have found their way into her cunt.

Jake unzipped his pants, and pulled his cock out. Traffic was still moving at a snails pace, so little concentration was required to drive.

Daisy rose up and whispered into Dwayne's ear, "Your fingers feel so good... but, you shouldn't have done that..."

"Why?"

"Because, I want to get off... now... before you blow your load in my mouth."

Dwayne laughed and said, "Now who's horny? Hop on Sis, I'll give you a ride."

Daisy slipped her panties off and climbed into his lap, easily guiding his cock into her wet cunt. Once she got past the initial pleasure of his cock sliding into her, she looked over Dwayne's shoulder and made eye contact with the redneck staring at her, his mouth agape.

Jake was wide-eyed, watching the blond bombshell fuck her cowboy, moving up and down on his cock. Holy fuck! He tried to stay cool, but could only imagine the look she must have seen on his face.

Daisy leaned back and stretched her arms out along the top of the windshield, pumping away on his rigid cock. Dwayne unbuttoned her tiny denim vest, freeing her large breasts. He took a handful of each, leaning forward to suck on her hard nipples. It usually took a little time to get off fucking her brother, but there was something about performing for the stranger that unexpectedly drove her over the edge, unleashing a powerful orgasm.

Jake watched it happen. Her eyes rolled back and closed at the same time her face turned to a grimace. Her body went rigid and she pressed herself down hard on his cock, rocking herself in his lap. Her expression softened to a smile as her orgasm subsided and her eyes opened, once again looking back at the rugged stranger.

Fuck! Jake almost blew his load right there, all over the dashboard. He wondered if the girl knew what he was doing?

She held her fist up and gave him several short pumps, answering that question. He nodded. She raised her eyebrows, twice in rapid succession. Did she want to see him?

Jake waited a moment for the traffic to stop, set the brake and then lifted himself up in the seat. He flopped his big cock over the top of the steering wheel.

Her eyes went wide when she saw it.

Jake knew what was going through her mind, "I've got to have that big cock". He gave his cock several long strokes, to set the hook, so to speak. Oh yeah! He had her now.

Traffic started moving, so Jake sat back down to drive. She gave him one last smile before getting back on her knees and going down on her cowboy.

Daisy sucked Dwayne in, taking him all the way down her throat. She desperately wanted to finish and get back to the stranger. She could hear Dwayne moaning, and sucked even faster. She felt him tense up and eagerly caught his load in her mouth.

She rose up and opened her mouth, ostensibly showing Dwayne his load of cum, but knowing that the stranger would see it too.

Jake watched her swirl the load of cum in her mouth and then swallow it in one gulp, licking her lips to show him it was gone.

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