The Cad - Cover

The Cad

Copyright© 2001 by Klaude Smith

Chapter 18

Erotica Sex Story: Chapter 18 - 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 took his time chatting with the ladies at the bar. He wasn't in the mood to meet anyone new just then. In spite of, or perhaps because of all the excitement he'd had recently, he wasn't feeling particularly anxious to meet more of Josie's many friends. Not that he was in an anti-social mood; he just felt like he was already juggling so many thoughts already. He watched Angie pouring drinks and basically charming the socks off the other patrons. She was certainly a sexy woman, Jake admitted. Even now, after all the sexual encounters he'd had over the past few days, he still felt his desire stir as he observed her movements.

He spent a little time flirting casually with Ellen when she had a free moment or two, as well as with Rachel. It's no use denying it, he realized: he was strongly attracted to them all.

Eventually, though, he looked up to see Josie waving him over, and he went to meet her classmates. As usual, he didn't have much use for the men, but their girlfriends were something else. Still, he had forgotten their names soon after meeting them, and didn't bother to find them out that night.

Later, after more people had shown up and the bar became more crowded, he pulled Josie aside to whisper that he was thinking of calling it an early night. She grinned, leaning up to kiss him on the cheek before. "That's what I want too," she whispered.

They'd walked home hand and hand, a slow, casual stroll in the moonlight, and Josie was glad to have Jake alone again. Later, after they'd made love again and then laid in bed watching a movie, she felt incredibly happy and content. Jake felt it too.

The next morning Jake woke first. He considered waking Josie with some gentle erotic play, but she looked so blissful in sleep that he decided to let her rest. He pulled on a t-shirt and shorts and went downstairs to putter around the house. He had a phone call to make, he remembered.


"Hey, there's Jake!" Fiona said to Ally.

The two girls were sun-bathing next to the pool in Ally's back yard. Fiona had just turned over onto her stomach, and Ally was on her back. Both were wearing skimpy little bikinis, ostensibly to work on their tans; Ally's was black, which went well with her dark, olive complexion while Fiona's was a bright neon yellow. Neither left much to the imagination.

Ally looked up to see Jake walking out on his deck, talking on a cell phone. From this distance there was no way he could hear them, but it still made Ally a little nervous for Fiona to speak so loudly about him. Ally had been nursing a crush on Jake ever since he'd moved in. From Ally's backyard, Jake's house was up a densely wooded, fairly sharp incline, so even though Ally's house backed up to his there was still a good fifty yards or so between his deck and Ally's pool.

"He never seems to look this way," Fiona said, somewhat dejectedly. She too had a thing for Jake. "Sometime when your folks aren't home, we should sunbathe naked to see if that gets his attention."

Ally rolled her eyes, outwardly scoffing the idea, but inwardly she had to admit that the idea had occurred to her already. She was too shy to do something like that, though.

She rolled onto her belly too, next to Fiona, and rested her head on her crossed arms.

"We're just little kids in his eyes, Fee. He probably thinks we're still swapping Pokimon and trading cooties shots." Ally sighed, watching as Jake paced back and forth, engrossed in his phone call.

"Speak for yourself, babe." Fiona said, propping herself up on her elbows. She arched her back, causing her breasts to slide forward on her towel. "I got plenty of woman going here," she said, referring to her ample curves. "And so do you, believe me." She turned to examine Ally's tanned posterior, letting her eyes run up and down her buddy's near-naked bod. "Yeah, you've got a great body, Ally. You just don't like to flaunt it, is all."

"It's not just that," Ally replied. "I mean, thanks and all, but this town is loaded with pretty girls. Guys like Jake aren't interested in high school kids when they spend all day on campus."

"Don't be a fool," Fiona admonished. "We're as a hot as any college chick, if not hotter. Hell, this time next year we'll both be in college anyway, right?"

Ally nodded, but her heart wasn't really in it. She lay her head down and sighed. "Anyhow," she told Fiona, "there's no point in getting all worked up over Jake. He's got a girlfriend."

Fiona crossed her arms and lay her head down too. She didn't say anything, but girlfriend or no, he'd been checking them out the other day, she could tell.

Both girls heard the sliding glass door opening and turned to see who was coming out. Ashley waved as she stepped out of Ally's house. She said something they couldn't hear to Ally's mom, who was inside in the kitchen, then closed the door behind her and walked around the pool to where her friends were laying out.

"Hey guys."

"Hey Ashley."

"Perfect timing, Ashley," Fiona said with a grin, pointing up towards Jake. "Look who's hanging out on the deck."

Ally suppressed an urge to tell Fiona not to point, conscious of the fact that Jake could glance down at any minute.

"Oooh, good!" Ashley said, unrolling her towel next to Ally's. "Where are the binoculars?"

Ally playfully poked her in response, and all three girls laughed as Ashley pulled off her shorts and t-shirt to reveal that she'd worn her bikini as well, a baby-blue number just for sunbathing; it was much too small for her to wear in public.

"Hey, is that new?" Fiona asked, noticing Ashley's sexy new suit.

"Yep. You can't tell anyone, though. My parents don't know I bought it. My dad would have a conniption if he saw me in this."

"I'm about to have a fit too, babe -- you look hot in that thing!"

Ashley just laughed, laying down on the other side of Ally and stretching out.

"Well, I had some extra cash from baby-sitting last Friday, so I..."

Ally and Fiona both had shocked grins on their faces, but Fiona was the first to interrupt her. "You mean from Mr. Davis?!"

"Please, I like to think of him as Karl," Ashley said, trying to suppress her pride.

"Did you do it with him again?" Ally asked, stunned to hear what her friend was saying. "He's, like, married with a bunch of kids and all."

"Wow, Ashley, you're such a little slut!" Fiona teased.

Ashley just giggled. "You're just jealous, that's all."

Ally gave Ashley a serious look. "You just better be careful, Ashley. You could get in a ton of trouble if anyone finds out, and so could he. You don't turn seventeen for another two months!"

"One month, three weeks," Ashley corrected. "Besides, I don't think it's going to go on much longer. He's already getting tired of me. After this last time he told me all about how what we're doing is wrong, and I should be with guys my own age, and all that nonsense that he didn't think to say before he fucked me."

Ally was too shocked to say anything right away. Fiona just waited for Ashley to go on. Ashley rolled over onto her back, trailing her fingers lightly across her flat, tanned tummy.

"But, boy, does he know what he's doing. I thought I was just going to die last night, literally pass out with him on top of me." She turned her head to look at Ally. "I know what you're thinking, and you're right. I shouldn't keep seeing him, but I can't help it. He's like a drug."

Ally was about to say something, but Fiona beat her to it.

"So, what exactly do you guys do? I mean, do you use protection?"

Ashley rolled onto her side, a grin on her face.

"He doesn't, but I do." Ally's eyes went huge then.

"You went to the clinic?"

"Yeah, can you believe it!"

"Why didn't you tell us?" Fiona burst out. "I would have gone with you!"

Ally and Fiona had both been on birth control for a couple years. Ally's Mom knew, but Fiona had never told her parents, instead just going to the local clinic on campus. At the clinic it was easy for her to get affordable birth control, and it didn't seem like a big deal for her. But both knew that Ashley had been hesitant to go on it herself. She was a year behind them in school, and she'd been too afraid her parents would somehow find out.

"Yeah, me too," Ally said. "You didn't have to go alone."

"I know, and I appreciate that, really. I guess it was sort of something I wanted to do on my own, you know?"

"God, my mom's talked about having the Davises over for dinner," Ally said. "I'd never be able to keep a straight face!"

Fiona suddenly lept up and jumped on top of Ashley, giggling as she straddled her friend.

"Welcome to the club, you little tart!" Fiona laughed, tickling her. Ashley squealed and tried to squirm free, but Fiona had her pinned down.


From the kitchen window, Ally's mom watched the girls horsing around as he finished drying some dishes. Ah, to be young again, she sighed to herself. She dried her hands on her apron. Though she still had a quite stunning figure, she no longer thought of herself as a sexy woman.

Upstairs, Ally's little sister, Amy, sat on her bed and played cards. She heard the girls outside and got up to look from her bedroom window. Amy was fifteen, but she was following in her older sister's footsteps with a strikingly cute face and a nicely curvy figure. She wore her hair shorter than Ally, just shoulder length. They got along alright, but Ally never invited Amy to hang out with her and her friends; the age difference was just too big. Or, at least, that's what Ally thought. Amy found that she was getting bored with kids her age, and more and more interested in what Ally's friends were up to. This was her first year at high school, and she already felt more in common with the older girls than with the kids she'd hung out with all summer.

She watched Fiona and Ashley playfully wrestling, and she wished she was down there with them. She imagined herself dressed in a skimpy bikini as well, writhing around as Fiona's bare legs pinned her down, their smooth skin rubbing against each other... She wanted to be with the big girls. She cupped her perky little breasts, assessing their size in comparison with her sister's. Amy figured she'd probably have larger breasts than Ally eventually. Ally was taller, and though she had a curvy body she'd always be slender. Amy was shorter, only around 5'5", and her body was a little more rounded. She'd really started to blossom this summer, and she liked the way she was filling out. But she was anxious to grow up, to stop being seen as a little kid.


After Fiona was satisfied that she'd made Ashley suffer enough, she relented and stopped tickling her, though she didn't get up right away, continuing to sit on her stomach. She wasn't resting her full weight on her, but enough that her crotch pressed firmly against the younger girl's midsection. Ally had her head propped up on one elbow, laying next to them.

"So, he calls you up to babysit, and then afterwards you guys fool around? Is that how it works?"

Ashley was still catching her breath, but she rolled her head over to smile at Ally.

"Yeah, that's pretty much how it works."

"Don't you ever talk to him other times?" Fiona asked. She found she liked her position, straddling Ashley, feeling her bare thighs against her friend's warm flesh. She absentmindedly started lightly tracing her fingers over Ashley's stomach, causing her to shudder as goosebumps formed.

"Well, I did try to call him once, but his wife answered and I kinda freaked." Ashley liked what Fiona was doing, and she casually put her arms down so that they gently brushed against her smooth thighs. She could feel her nipples stiffening in response to the sensation of Fiona's fingertips. "That's one of the things that's weird for me. I really like Kathy, his wife. And, of course, I love the girls."

Fiona thought about that for a moment. "I guess that is pretty sleazy of him to be sleeping with the baby-sitter behind his wife's back."

"Thanks a lot!" Ashley protested, bucking up to knock Fiona over.

"Hey, I didn't mean anything by it," Fiona pleaded, wishing she hadn't said anything. "I just don't want to see you get in trouble."

Ashley sat up, looking sheepishly at her hands in her lap. Ally sat up too, wrapping her arm around Ashley's shoulder.

"Yeah, we're just looking out for our buddy," she assured her.

Ashley shrugged her shoulders weakly, putting on a brave face.

"I know, you're just looking out for me." She smiled, first at Ally then at Fiona, who was rising to her feet. The blond girl reached down with both hands to pull Ashley to her feet.

"Come on, let's get some sodas from Ally's mom."


"Cool, that sounds perfect. I'll talk to you later, Simon. Thanks again."

Jake hung up his cell and slid it back into his pocket. He never really enjoyed talking to attorneys, but he knew he had to touch base regularly with his, if only to maintain a rapport with him. He was a basically good guy, even if he was a lawyer, and Jake was glad that Klaude had introduced him. He kept Jake's affairs in order so that he didn't have to worry about the money or his parent's estate or any of that bother. Talking about his past with Darcy had got him thinking more about both the past and his future. He'd been gliding through life so far, and even though he was now in school, he still felt a little aimless. But he didn't want to dwell on it right now.

Jake took a swig of beer and stretched his arms. It was another pleasant day. He considered going for a swim, but he didn't really feel like leaving the house just yet. He set his beer on the ledge and leaned forward, looking out at the woods in back.

Through the leaves he noticed some motion, and he moved a few steps to his left to better see what it was. He saw the three girls down by the pool and remembered that they'd told him they liked to lay out there. They looked to be horsing around now, wrestling and tickling each other. Jake recognized Ally and Fiona, but he didn't think he knew the third girl. Whoever she was, her suit was as tiny as the others', and Jake was enjoying the show.

"So this is where I find you, eh?" Josie said, wrapping her arms around Jake from behind.

"Oh, er, hi honey, I didn't hear you come out," Jake joked, pretending to have been caught in the act. "Nothing to see out here, I swear."

She giggled as she hugged him, leaning into him so that her body pressed against his back. Jake sighed and pulled her arms tighter, enjoying the feel of her sexy body against him. Josie put her head on his shoulder as she looked to see what had caught his eye.

"Mmm, watching the little neighbor girls, are we? My, they look like little nymphs, frolicking around like that."

Jake laughed, nodding in agreement. Josie slid a hand down the front of his shorts, gently cupping his flaccid penis and balls through the fabric.

"Guess they're too far away to see all that well, hmm?" she teased. "Or have you just started watching?"

Jake's cock began to swell in response to Josie's actions, and he grinned.

"Well, it sort of killed the mood when my girlfriend caught me," he laughed, and Josie playfully slugged him in the stomach.

Jake spun around and grabbed her wrists, holding them up, and Josie giggled, struggling playfully to escape his grip.

"Oh no you don't," she laughed. "If you'd rather watch the little girls, I'll just go back inside."

Jake pulled her to him, leaning down to kiss her forcefully, and she opened her lips to meet his. After a minute Jake released her slightly, looking in her eye.

"Don't you go anywhere," he said quietly, before pulling her back to him. He let go of her wrists then and grabbed her slender waist, caressing her sides as Josie moved to wrap her arms around his neck, her tongue in his mouth. She kissed him for another minute or so, loving his hands on her body. She was wearing an over-sized t-shirt that hung down to mid-thigh over her bikini bottom, and it felt wonderful to feel her body sliding against his through the thin fabric.

"Mmm," she whispered as she kissed his neck, "I guess you did get a little hot and bothered after all. Did watching those little high school sluts give you some ideas, Jake?" She ground her pelvis into him, rubbing herself up and down over his rising erection.

"You're the one giving me ideas, beautiful." He reached down to cup her wonderful, tight little ass, pleased that she was only wearing her swimsuit under her shirt. She let out a small moan as he squeezed her ass cheeks, massaging her smooth, firm ass.

"Mmmm, you're giving ME some ideas, too, Jake. Mmmmmm, why don't you see if your little friends are still putting on a show for you."

Josie kissed down his neck, one hand on his chest now, pinching his nipple through his shirt while the other came up and unfastened his snap, pulling his zipper down. Jesus, Jake thought, Josie's really in the mood!

She was. Josie knew those girls were aware of Jake. Hell, they probably thought he was as hot as everyone else did, and they probably were putting on a little show for his benefit. She was used to it, the way Jake attracted the ladies, and she didn't really mind. In fact, the idea of those little high school hotties getting all worked up for Jake kind of turned her on.

She pulled up his shirt, running her hand over his muscular torso as she went down on one knee, kissing his stomach and rubbing her face across his skin. She pulled his pants down, releasing his turgid pole so that it bounced up towards her, and she grabbed it at the base, tightly gripping it with her small fingers. She pumped it a couple times, just kissing the sensitive skin around his crotch, and Jake gasped. She smiled up a Jake with a devilish look on her face.

"Look at them, Jake," she purred, slowly pumping her hand up and down his thick shaft. "Look at those little tramps prancing around for you. They want you to go down there and fuck their hot little boxes silly, Jake. They want you to stick your fabulous cock in their wet little pussies and fuck them all."

Jake grinned, looking down at Josie as she slurped his tool into her hungry mouth. God, she was sexy. She continued running one hand across his chest and stomach while she greedily started sucking on his cock, holding him by the base as she bobbed up and down. She let him pop out of her mouth and licked his swollen, glistening head, a delightful sensation.

Josie was imagining Jake with those little girls, bending them over and fucking them from behind one by one, their hot little bods quivering with the intensity of his fat cock entering their tiny little pussies, and Josie ran her lips up and down his shaft, worshiping him, coating him with her saliva.

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