The Cad - Cover

The Cad

Copyright© 2001 by Klaude Smith

Chapter 39

Erotica Sex Story: Chapter 39 - Jake loves his girlfriend, Josie, but can't seem to keep from hooking up with other women.

Caution: This Erotica Sex Story contains strong sexual content, including Ma/Fa   Ma/ft   Fa/Fa   Mult   Consensual   Reluctant   Lesbian   Heterosexual   Cheating   Exhibitionism   Voyeurism   School  

Jake stepped around the corner of the garage and saw that the high school party was still going full steam. He stifled a yawn, wondering what time it was. Two in the morning? Three? He needed to go home before he got himself into any more trouble. Around the time he'd pumped his third load into Fiona his conscience had started nagging him again. He and Ally had shared a pretty special moment earlier that evening, yet despite that he'd been unable to control his selfish desire to fuck her best friend, too. Not to mention the fact that he'd just come from fucking Anna and Monica before that.

And not to mention that Josie, his girlfriend, the love of his life, would be home tomorrow night.

He ran his fingers through his hair, shaking his head to clear his thoughts. Try as he might, though, he just couldn't bring himself to regret any of it. Fiona was a hot fuck, and he definitely wanted to tap that ass again soon. Same with Ally. Between the two of them he was hard pressed to say which he liked more, and he didn't really care; he planned on enjoying them both.

But he wasn't so horny to think that there wasn't a potential problem here. For one thing, they were both barely legal (he pushed thoughts of what he'd done with little Amy aside for now). Beyond the age thing, though, he was pretty sure that neither of them suspected that he'd fucked the other one. How could they? He'd dipped his wick in Fiona right after being with Ally, so it wasn't like they could have discussed it already. But they would eventually, and there was no way to tell how they might respond. He certainly didn't want to be in the middle of some messy high school cat fight.

He laughed to himself, too tired at that point to really care. He strolled over to the keg, grabbing a cup and filling it with beer. Kenny and Danny both watched, and he nodded to them with a smile.

"Gentlemen."

"Howdy," Kenny said, wondering who the older guy was.

"Jake!"

Amy appeared suddenly and threw her arms around him, causing him to nearly spill his beer.

"Hey there, sister, hold on!" Jake laughed, wrapping an arm around the youngster and holding out his cup to avoid splashing its contents onto them.

Amy just laughed with him, giving him a hug and a quick kiss on the cheek.

"It looks like you're having a good time," Jake said, releasing her.

Amy stepped back a little, grinning. She realized she'd gotten a little buzzed over the course of the evening, and she felt good. She could tell Danny was watching her from the corner of her eye but she chose to ignore him for now, focusing her attention on Jake.

"Where have you been? Here you come to our party then right away you disappear." She gave him a pouty look but couldn't quite wipe the smile off her face.

"I'm here now, aren't I?"

"Yeah, and I'm not letting you out of my sight. Come on, I want you to meet my new buddies."

Jake let her introduce him to Kenny and Danny, shaking their hands and making small talk. He felt a little self-conscious about being the only guy there who wasn't still taking study hall, but he didn't dwell on it. So I'm a dirty old man, he laughed to himself.


The rest of the evening went pretty much the way those things usually do. The crowd of kids who could stay out late dwindled until there were only a handful of folks. Surprisingly, no one had puked or broken anything through the course of the evening, a fact which Ally and Amy both appreciated.

Jake had started to pick up around the pool as the last of the kids were making their exits, and Danny and Kenny joined him, making quick work of straightening up the backyard. Amy came out to help as they were finishing up.

Inside, Ally and Fiona found themselves alone in the kitchen for the first time since the party started.

"So," Ally said guardedly, "it looks like it was a success."

Fiona detected something in Ally's tone that she couldn't quite place.

"Um, yeah, I think so." She dumped a stack of cups into the garbage bag they were filling up. "Ally, are you mad at me?"

"Why would I be mad at you?" Ally asked, not looking up from the counter she was wiping down.

Fiona went over and put her hand on her friend's arm.

"Come on, Ally, what's up? You can tell me."

Ally looked Fiona in the face with a coldly neutral look.

"I don't have anything to tell you, Fiona. Maybe there's something you want to tell me?"

Fiona bit her lip, blushing furiously.

"You know? About me and..."

"About you and Jake? No, what is there to know about you and Jake?"

"Ally, come on. I'm sorry, I know you like him too, but I couldn't resist!" She put her hands on Ally's shoulders, a pleading look on her face. "Oh Ally, I'm sorry, I'm sorry. But I wanted him so much, you don't understand. And it's not like we had agreed he was off-limits or anything. When he came back to the party, one thing led to another and we just, he just..."

Ally pulled her friend to her, wrapping her arms around her and giving her a warm hug.

"I'm sorry too, Fiona. I'm not mad at you. Really, I'm not."

Fiona pulled back to look in her eyes.

"Seriously? You don't hate me?"

Ally sighed. "I'd be lying if I said I wasn't jealous. But no, I'm okay with it. Really."

"I'm so relieved, Ally. I didn't know what to say, and I wasn't sure how to tell you." She sat down at the kitchen table. "Besides, it's not like I'll get to see him again. He's got that girlfriend, you know."

Ally took a seat across from her, taking a sip of her beer.

"Yeah. Josie. Lucky bitch, huh?"

Fiona laughed.

"Yeah, I hate her," she half-joked. "Although I guess he can't be a very loyal boyfriend, right?"

Ally laughed at that. "No, I guess not." If you only knew, Fiona, she thought to herself.

"Then again, maybe they're swingers." Fiona glanced over her shoulder to make sure they were still alone. "Can I tell you something? You have to promise not to ever say anything."

"Of course," Ally said, scooting closer, wondering what more there could possibly be to tell. She felt a little guilty about not 'fessing up with Fiona about her own encounter with Jake, but she wasn't ready to reveal that just yet.

"Well, I feel a little weird about this, but I went up to Jake's house last week. I was just gonna stop in and say hi, you know, flirt with him a little more. I know, I know, I'm a whore."

Ally laughed, remembering how Jake had called Fiona a slut while he fucked her silly.

"Anyway, I wasn't spying or anything, but I looked in and saw him having sex."

Ally's eyes grew wide.

"With his girlfriend?"

"With his girlfriend AND another chick!"

Ally sat back, a look of surprise on her face.

"You're kidding."

"I swear I'm not fucking with you," Fiona said, shaking her head. "There was another blond chick with them, and they were having a total three way."

"Wow."

"Yeah, wow," Fiona said, taking Ally's beer and gulping down a big swig as she looked over her shoulder again. "I tell you, it was the sexiest thing I've ever seen, too."

"Really?"

Fiona nodded vigorously.

"I've been so worked up ever since then, I thought I was gonna burst. I mean, god, you wouldn't believe hot sexy it was to see him with those girls. And they were obviously having a good time, let me tell you."

"Yeah, I can guess that would be pretty hot," Ally said absently, remembering how excited she'd gotten watching Fiona with Jake. "So you decided then to jump his bones as soon as you had the chance, eh?"

"Well, not exactly. But yeah, I've been thinking about him a lot lately. You're sure you're not mad at me?"

Ally sighed, finishing up her beer and tossing the empty cup into the garbage bag. Fuck it, she thought to herself; I should just tell Fiona what happened and see what she has to say.


"So, dude, that was really decent of you to hook the ladies up with the party supplies tonight," Kenny said, taking the bag of trash from Jake.

"It was nothing," Jake said, "just glad to help out. I'll tell you what though, I feel like I'm about to drop. Think you guys have everything under control here?"

"Sure, sure," Kenny said. "There's only a few stragglers left and we can give them rides." He held out his hand to Jake. "Hope to see you again, bro."

Jake shook their hands, then went over to say goodbye to Amy.

"You'll be back tomorrow, right?"

"At least to pick up the keg, honey. Do you need help with anything else?"

"Um, well, I guess not," she said, suddenly shy again. "I was just kinda hoping you'd come back over. Mom and Dad don't get back 'til later."

Once again Jake's conscience reminded him that sexy little Amy was jail-bait, but he pushed those thoughts aside.

"We'll see, okay? No promises."

"Good enough." She glanced around to make sure that Kenny and Danny weren't paying attention to them, then she gave Jake a quick kiss on the lips. Jake threw caution momentarily to the wind, kissing her back, savoring her full lips and wet tongue while allowing himself the all-too-brief pleasure of having his hands on her tiny waist.


"Fiona, the thing is..."

Ally was cut off by the sound of Amy and Jake coming in through the back door in the family room. They came into the kitchen to find Fiona and Ally sitting at the kitchen table.

"Hey gals, thanks for a great party, but I think I need to call it a night."

Fiona was practically glowing, an ear-to-ear grin on her face, and Ally thought she picked up a slight flash of concern on Jake's face. Was he feeling guilty about sleeping with both of them? Ally couldn't be sure. He certainly didn't lose his cool if he was.

Amy was clearly smitten with him as well, Ally realized. For a split second the idea of Jake having sex with her little sister flashed in her mind.

Jake put his hands on Ally's shoulders, standing behind her as she sat at the table across from Fiona.

"Let me know when you guys want me to come pick up the keg, alright?"

He bent down and gave Ally a quick peck on the cheek. He'd have liked to do more, but it didn't seem quite appropriate. Fiona didn't care, though, hopping out of her seat to give Jake a big hug, wrapping it up with a kiss on the lips.

"See you tomorrow, Jake," she said softly, winking at him.

"Yeah, yeah," Jake said, slipping away. "See you tomorrow!"

Amy and Fiona grabbed seats at the table with Ally and watched as Jake left.

"Mmm," Fiona sighed happily. "Say, what were you saying Ally?"

"Oh, never mind," her friend said simply. "Nothing important."


It was nearly 4:00 a.m. when Jake stepped out of the shower, quickly toweled off and fell into bed. He'd almost just gone straight to sleep but had wanted to clean up a little before hitting the sheets; Fiona had been quite an enthusiastic partner, as evidenced by her remains on his crotch and thighs.

He stretched out in bed, sleepy but wired. Despite all the fun he'd had the past couple days, when it came down to it he really missed Josie, and the bed felt empty without her. Just thinking of her caused his cock to stir once more, imagining the look on her face when she came, the sounds she made and the way she shook and held onto him when they fucked. Of course, that wasn't why he loved her; she was also his best friend. But the sex was great.

Then why am I always sleeping around? he asked himself for the umpteenth time, not really bothering to rationalize an answer. His thoughts returned to the delicious variety of women he'd recently enjoyed, savoring the memories of each of their distinct bodies and personalities. What man wouldn't take advantage of such delights?


Morning came quickly, and Jake woke to find the bedroom bathed in bright sunlight. He rolled out of bed, feeling stiff but energized, and after a quick snack he threw on some sweats and headed to the university gym for a quick work-out. He half-expected to run into Darcy or Brittney there, but the place was pretty dead that morning, just a fraction of the usual throng of coeds milling about.

He kept his focus, ignoring the ubiquitous young hotties in the machine room, and was done in less than an hour, feeling even more energized and alert than when he'd woke up. Biking back he was struck by just how nice the weather was, enjoying the gentle breeze as he pedaled through campus. Then he remembered his date with Rachel. Smiling broadly, he steered his bike downtown.


Rachel was wheeling in a keg on a hand cart when she heard a rapping at the front window of Fat Teddy's. She looked up and saw Jake peering in, waving to her.

She took a deep breath, willing her nerves steady. Rachel had been anticipating this moment all morning, wondering if Jake was really going to show and what might happen if he did. Now he was standing just outside, ready to come in, and Rachel's heart was racing at the prospect of being alone with him once more. She took another deep breath, smoothing her jeans out by rubbing her hands down her thighs, and then adjusted the baby-doll t-shirt she wore. "Hey there, Jake," she said after she'd unlocked the door for him. "I wasn't sure if you'd show."

"What do you mean?" Jake asked in mock surprise. "We're in business together, aren't we?"

"Hee hee, not yet, mister. Come on and help me swap out this keg."

Jake easily removed the empty barrel and man-handled the full one into place, then Rachel connected the taps, trying to hide the fact that her hands were shaking.

"Deja-vu," Jake said.

"What are you telling me, Jake? Did you have another kegger?" Rachel asked, leaning back against the bar and wiping her hands on a rag.

"Well, no, not exactly."

Jake followed Rachel upstairs to the office and told her how he'd purchased a keg for his high-school-aged neighbors. Rachel just shook her head in mild disapproval.

"You're gonna get yourself in trouble, buddy. I assume these 'kids' you speak of are female?"

"What makes you say that?" Jake asked with a grin.

"Uh-huh, that's what I thought."

She sat down at the desk and pulled out some paperwork, spreading the papers out for Jake to examine.

"You're all work today, eh?" he asked in a sly voice.

Rachel swallowed and looked up at Jake, smiling despite herself. She'd been practicing her resolve all morning, trying to convince herself that she could keep this meeting professional while fighting the urge to throw herself at him.

"Jake, this is really important. I know it's not any big deal for you, but I really want to make this work, and I need your help."

Undeterred, Jake stepped closer to her, reaching out to take her hands in his.

"And you've got it, babe, I promise. But I can't get down to business right away."

He pulled the buxom brunette to her feet, turning her so that her ass was against the edge of the desk, stepping close so that his body pressed against hers, his hands at her waist. Rachel grinned at him, draping her arms around his neck and licking her lips.

"Jake..." she began, tilting her head to one side and giving him a coy look.

Jake's lips cut Rachel off before she could finish her protest, though, and she kissed him back, pushing her tongue into his mouth to meet his.

Jake's cock was already rising to the occasion, encouraged by the sensation of Rachel's voluptuous body pressing against him. He unabashedly caressed her figure with both hands, stroking her slender, curvy torso, her round hips, and moving up to cup her generous, firm breasts through the thin fabric of her baby-tee. Rachel groaned appreciatively, hungrily kissing him back.

"Jake, Jake..." she moaned, letting go of her inhibitions and letting herself enjoy the feel of his hands on her. Rachel wanted to resist him, to make him take her seriously, but her resolve was quickly slipping away.

"Mmmm, oh Jake," she sighed, running her fingers through his hair, her eyes half-closed, dreamy. "Jake, what about Josie?"

"You don't need to worry about her," Jake said in a low voice. "You just worry about me."

He roughly pulled her shirt up, causing her heavy breasts to rise and then pop out, bouncing on her chest as he yanked the small garment over her head. He flipped the center clasp of her black lacy bra and it flew open easily, rewarding him with a grand view of her wonderful tits. Jake wasted no time in cupping them both in his hands, squeezing and kneading them, rolling her fat little nips between his fingers.

"Aghhh!" Rachel gasped, surprised by how quickly Jake was moving. "Jake, wait, I want to talk to you about this..."

Jake ignored her and bent down to suck one of her firm round globes into his mouth, taking nearly half of the precious flesh into his mouth as he continued to tweak its neighbor. Rachel's tits were plenty large but he was pleased to find that they were quite firm and perky despite their heft, and he was enjoying playing with his new toys. He snaked his free hand down the smooth warm flesh of her flat tummy, slipping his fingers into the waistband of her jeans and fingering the snap at her fly.

"Jake... Ohhhhhh!"

Rachel was torn between wanting Jake to take her seriously as a business partner and needing him to fuck her as soon as possible. Her body was working against her, the carnal tension quickly building as Jake worked on her sensitive breasts, and she sucked in her breath when she felt his hand at her jeans, flipping the snap and pulling them open to dip into her lacy panties.

"Jake, mmmmm! Oh Jake, baby, mmmm, that feels so good!"

Jake grinned, luxuriating in the soft, pillowing cushion of her breasts as he negotiated her jeans open and began working them down her round hips. He slid a hand around to cup her ass, pleased to find her thong gave him ready access to her firm round cheeks, and he cupped them with one hand while his other pressed against her furry mound. Already he caught a whiff of Rachel's sweet musk, and her hands in his hair held him tightly, stroking him as he sucked her sexy tits.

"Jake, please, wait..."

Jake looked up at her, grinning as he worked a single digit between her thick, swollen pussy lips to wiggle into her slippery folds, aware that she was already quite moist in anticipation.

"Shhh, Rachel; less talk baby."

"What? Jesus, Jake, you think you can just come in here and -- Ohhhh!"

Jake brushed the length of his finger across Rachel's stiff little clit, gently worrying the sensitive bundle of erotic pleasure and setting off a sharp reaction in the sexy bartender. She arched her back suddenly, pushing her breasts once more into Jake's face as she shuddered. Jake drove his finger once more between her lips, penetrating her sweet, wet passage while keeping pressure on her swollen nub.

"Rachel, if you want me to stop, I'll stop, but I don't think that's what you want."

"Jake, please, just give me a minute," Rachel gasped, suddenly feeling quite out of control. Her heart was racing and she couldn't focus her thoughts, not while Jake was setting off such an incredibly titillating rush of delight in her center. "Mmmm, oh fuck, Jake!"

Her hips bucked, and Jake straightened slightly to kiss her open mouth as she let out a squeal, arching her back further. He wrapped an arm around her waist to hold her steady, all the while working a second finger into her snug, warm tunnel. Rachel kissed back at him, moaning in a low, almost pleading sound, and Jake didn't know how much longer he could wait to get his cock into her.

The two girls before her had been quite sexy little things on the verge of maturity, but Rachel was a grown woman, and Jake appreciated the difference. Although she was holding back her urges still, Rachel was clearly a deeply erotic woman, self-assured and in touch with her sexuality. Already Jake was drinking in the way she moved her fabulous body against his, opening herself to him in the knowledge that he would satisfy her every need.

Rachel was already pulling at his sweatpants, pulling them loose and pushing them down, well aware of the turgid pole within straining for release. When his cock finally sprang free from its confines it slapped her thigh heavily, and she wasted no time in grasping it in both hands, guiding it to her.

"Fuck, Jake," she giggled breathlessly. "You really are shameless, aren't you?"

Jake just chuckled, grabbing Rachel's hips as he positioned himself for entry, pushing her slightly back onto the desk. She lifted her legs and he yanked her jeans off her legs, dropping them to the side as she spread her thighs wide, placing her small feet on his hips. She grinned at him through eyes half-closed with lust, tossing her long, raven-dark hair back in a gesture that Jake found incredibly erotic.

"Mmmmm, Jake! Oh yeah, yeah, I'm ready," she growled as she felt Jake's swollen fat head at her entrance, squeezing its way into her wet snatch. His girth spread her lips wide, eliciting a series of high moans and cries from her as he slid slowly into her, burying himself to the hilt.

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