Joy Ride Pt. 03

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A MILF takes her son's friend to a lover's lane.
5.2k words
4.74
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96

Part 3 of the 3 part series

Updated 06/09/2023
Created 03/02/2019
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plushpeach
plushpeach
579 Followers

NOTE: You asked, and I listened! As requested, here's Part 3 of Lynn and Brad's adventures. If you've read some of my other stories, you may notice that some familiar names pop up here. This is the longest story I've published on here, so I truly hope you get as much out of it as I did. It's been a work in progress for a while, due to how long it's taken to finish, but that's half the fun! If you have any requests, ideas, or criticisms, please comment or give feedback. Enjoy!

*****

"Pull it together, Lynn!" She whispered to herself. Lynn looked at her reflection in the mirror, fixing her lipstick in the dim fluorescents of the bathroom. Her friend Jillian was hosting their weekly book club, so it was a group of moms, some bottles of wine, and a book none of them had read, all sitting in a circle, loudly gossiping about their husbands, their kids, and their every complaint.

Lynn typically enjoyed the book club, but now, things were different. This was the first meeting since her encounters with Brad, the son of her gracious host, and close friend, Jillian. In a little over the span of a week, Lynn had given Brad his first handjob, then later, his first blowjob. Now, she had to excuse herself to the bathroom to splash her face with cold water; no matter how hard she tried to focus on the drunken conversations about which bag boy at the supermarket was cutest, she couldn't stop thinking about Brad, only a few rooms away. As the other women chatted, she felt the heat between her legs as she imagined sneaking away, tiptoeing upstairs, and finding Brad in his bedroom.

"Cool it, Lynn!" She whispered aloud to herself. Last time, she'd faked a distress call to Brad, pretending she needed assistance after her car broke down. Really, she just needed an excuse to be alone with him, and in a car seemed to be the safest bet during the day. She'd lied to Brad about having been grocery shopping, she'd lied to Brad again about trying to call her husband for a ride, and she'd lied to her husband about spending the day at home while he was out shopping with their son, Kyle. Speaking of Kyle, he was a big reason she knew she couldn't do anything more with Brad; Kyle and Brad were best friends! He could never find out what she'd done.

"Lynn, you okay in there?" A voice called from elsewhere in the house. She realized that the other women had stopped chatting, and must've been waiting for her to return. Had she been gone that long?

"Oh, yeah, I'm good." Lynn called back, drying her hands off on the soft towel next to the light switch. She opened the door, shutting off the light, calling out again, "I'm good." She turned the corner, entering back into the living room with a smile.

It was getting late. Brad had been studying for almost four hours straight, feeling confident for his Spanish test tomorrow. The new teacher was giving exams every week, which meant he had to study a lot. These tests were every Friday, which meant he spent his Thursday nights studying, a challenge now that his mom was hosting her book club every Thursday night.

From his bedroom upstairs, he could hear the local moms drinking healthy amounts of wine and loudly chatting about every facet of their personal lives, occasionally pausing to laugh heartily at a punchline Brad missed. Curious, and tired of studying, he shut his textbook and headed downstairs. As he made his way down, Brad could clearly hear one of his mom's friends, Michelle, discussing a pizza delivery guy she'd heard a rumor about.

"Extra sausage, you know? Maybe we need to order a pi— Bradley!" Michelle exclaimed as he turned the corner into the living room. Lynn found it hard to swallow for a moment, caught off guard by the young man entering the room. She locked eyes with him, but only for a brief second, before he moved on, getting a look at each of the other women in the room. But all it took was that brief moment of eye contact for Lynn to remember how badly she wanted his cock again; she took a deep breath to center herself.

"Hi, ladies," Brad gave a soft smile as he looked around the room. He saw his mom, Jillian, sitting at the edge of one couch, pouring herself another glass of wine. Next to her, her friend Karen, new to the book club, nursed a half-full glass. She was in tight pants and an even tighter top that accentuated her large bust. Across from her on another couch was Diane, another friend of his mom's; she was chubbier than the other women, and she wore it well. She was wearing a yellow cardigan that draped effortlessly over her curves. In front of Diane, in her own armchair, was Michelle. She had a daughter a grade above Brad. Michelle was in a long, thin, flowy skirt that covered her ankles, and a equally thin tank top that did a poor job at hiding her hot pink bra straps beneath. However, none of these women captured Brad's attention quite as much as Lynn did. Sitting on the same couch as Diane, she had no wine glass in front of her. She held a book in her lap, and was dressed in a thin sundress that dropped to her ankles in the back, but rested just above her knees in the front. Her red lipstick was eye-catching on her tanned skin, and her natural blonde hair was pushed behind her ears. Lynn held Brad's gaze for just a moment, before he felt guilty for admiring her long, smooth legs, and looked back to his mom.

"Brad!" Jillian said. "What a treat, the ladies don't typically get to see you!" She stops and walked over to him, wobbling slightly on her first step. She, like most of the other women, had clearly had more than a few glasses of wine. She steadied herself against his shoulder, standing next to him as if showing him off to her friends.

"Sorry, I didn't mean to interrupt." Brad apologized. The women were certainly taking their time appreciating the young man standing before them. He was tall, athletic, with he had such an innocent look in his eyes.

"Oh, not a problem, honey. We're actually just finishing up." Jillian nodded to the other moms, who all murmured I distinctly about having to get home, checking their watches and phones. "Looks like I'll need to call you all a ride, huh?" Jillian asked.

"Yes please!" Karen called out, rising to her feet. The other women also stood up, visibly tipsy, gathering their things.

"Wait," Brad interrupted from the side of the room. "Why don't I give you all rides home?" Since getting his license recently, he'd been trying to help his mother out as much as possible. This seemed like a great way, saving all of them money. Besides, he needed a break from studying, and even if he didn't expect anything elicit to happen, it was still a bit of a rush for Brad to ride in any car with Lynn.

"Oh, that would be wonderful!" Jillian exclaimed, happy to see her son offering to help. Lynn perked up. All together, the gaggle of drunk women made their way out of Jillian's home, hugging her goodbye and thanking her for hosting, before piling into Doug's Jeep. Diane climbed in first, sitting behind the driver's seat. Karen slid into the middle seat, next to her, and Michelle sat behind the passenger's seat. Lynn walked up, noticing that the three others had taken the backseat, and swallowed hard before opening the passenger door, realizing she'd be sitting next to Brad as he drove.

In the driver's seat, Brad also swallowed hard, waiting until Lynn was looking down at her seatbelt buckle to adjust himself, trying his best to hide his swelling package. In his gray sweatpants, he could still make out a straining bulge, but it was better than a tent. With a turn of the key, he put the car in drive and pulled out of his driveway.

As he drove, Brad glanced at the woman next to him, then to the women in the backseat. Beside him, Lynn, sober, looked straight ahead, trying her hardest not to stare at the now-obvious bulge in Brad's pants. Her blonde hair wavered as she realized she was holding her breath; exhaling, her ample breasts caught Brad's eye. Behind him, the three drunk women chatted amongst themselves about their weekend plans.

"Thank you for—hic—doing this for us!" Karen hiccupped as she called up to Brad.

"Yeah, thanks so much!" Diane added, sweetly.

"Yes," Lynn smiled, looking to Brad. "Thank you so much." Feeling bold, she reached over, patting him twice on the thigh. In a moment so brief Brad wasn't sure if it actually happened, Lynn ever-so-slightly grabbed a handful of his hard cock, before bringing her hand back to her lap. Brad almost swerved off the road as he pulled up in front of Diane's house, feeling his cock throb in his pants.

"Diane, I didn't know you lived by Cherry Lane!" Michelle perked up, looking out the window as the car slowed to a stop.

"Oh, yeah, talk about memories, right ladies?" Diane laughed as she got out of the car. "Thanks again for the ride!" Brad watched as she made her way up her walk, opened her door and entered her house.

"What's on Cherry Lane?" Brad asked, curious. He knew of the street, which snaked around the hill behind Diane's house, but as far as he knew, it was just a dead end that overlooked the town. There was nothing up there but a few spots to park and a street lamp.

"Oh, come on, Bradley," Michelle chided in jest. "You must know about Cherry Lane. Every teen in town knows about that place." She nudged Karen, who was also smiling.

"It used to be something of a 'lover's lane,' if you know what I mean." Karen giggled. "High schoolers used to park up there to make out and, well..." She let her voice trail off suggestively. Brad knew exactly what she meant.

"But, it was especially famous back in the day because that's where you went to lose your virginity!" Michelle jumped back in. "If you were going to Cherry Lane, you were going to pop your cherry!" She and Karen giggled, whispering amongst themselves about times past.

"You've been there, now, haven't you Bradley?" Karen asked, but he didn't respond. "Come on, a strapping young man like you? You must have taken dozens of girls to Cherry Lane by now!"

"I, uh, well—" Brad stammered, blushing.

"Don't tell me you're still a virgin, Bradley!" Michelle called out, shocked.

"Actually, Ms. Michelle, we're here at your house!" Brad changed the subject as he pulled up in front of her home. Unfazed, she opened the door and climbed out of the car, only tossing a drunken "Thanks!" to Brad as she walked to her front door.

As he drove off, Brad felt bold, and got an idea. He checked his rearview mirror; Karen was staring out the window, not paying any mind to anyone else. With confidence, Brad took one hand from the steering wheel and swiftly slid it onto Lynn's leg, holding a lose grip on her thigh.

Lynn felt her breath hitch in her throat as she watched Brad not take his eyes from the road, even has his hand crept under the hem of her dress. Careful as to make sure that the woman in the back wasn't paying attention, he snuck his fingers into her lap, brushing up against her silk panties. Taking a breath, Brad pushed her panties to one side. One finger traced her lips, feeling a hint of wetness escaping from them. She squirmed under his touch, and Lynn had to bite her lip hard to stifle a surprised moan as Brad inserted one, then two fingers into her warm, waiting pussy.

While driving, Brad began to finger her, massaging her folds, and teasing her clit. Lynn couldn't help but bite down on her own finger to keep quiet. She was mortified that Karen might catch on to what was taking place, but she'd be damned if she actually wanted it to stop. Brad teased Lynn as he drove, alternating between fast and slow motions, massaging her clit, bringing her closer and closer to the edge, until she just couldn't take it anymore. All at once, Lynn felt the orgasm roll through her body. She bucked hard against Brad's hand, letting out a only stifled whimper. As Brad pulled the car to a stop in front Karen's house, the woman climbed out, and said goodbye. Lynn couldn't even bring herself to say goodnight to her friend, too afraid that if she tried to speak she'd only be able to moan Brad's name.

"Well, Mrs. Lynn," Brad smiled as he pulled away from the road. "Next stop, your house."

"No, Bradley." She spoke slowly. "Drive to Cherry Lane."

-

After a quick drive, Brad got to the top of Cherry Lane, the infamous lover's lane he'd never known about. Atop the hill, there was a small clearing with a view of the suburb below. There was a row that accommodated maybe three cars, lit by a single street lamp, which cast an orange glow on the area. As Brad parked, he felt the strain in his pants throb as he imagined what might happen next.

"Get in the back." Lynn told him once the car was stopped.

"After you," Brad gestured, turning off his lights.

"Always the gentleman." She smiled back at him before unbuckling her seatbelt and climbing over her chair. As she climbed into the backseat, Brad watched her ass in the rear view mirror, perfectly outlined by her sheer dress, which was just short enough for him to get a peak at her silk panties. For just a moment, Lynn paused to wiggle her ass in the mirror as the young man looked on, and Brad felt his cock press against his pants. She finished climbing back, settling herself on the driver's side, behind Brad. He took a deep breath, removed the key from the ignition, dropped it in a cup holder in the center console, and climbed into the backseat as well.

In the back, Brad say across from Lynn, who had her back to the window. She had kicked her shoes off, and was running one hand up her smooth leg, tracing her finger along her calf, up towards her thigh. Brad watched, hypnotized, as her finger stopped just as it reached the hem of her dress.

"Bradley?" She spoke, breaking the silence.

"Y-yes, Mrs. Lynn?" He looked up from her thighs to meet her gaze.

"Lose the shirt." Lynn commanded, and he did not hesitate, pulling his shirt over his head, tossing it to the front seat. For a moment, Lynn admired his young, muscular figure, before continuing, "Now take off your pants." In a matter of seconds, he slipped his sweatpants down to his ankles, kicking them off, sitting in only his tight briefs, which could only barely contain his raging erection.

Resting on her knees, Lynn leaned in towards his lap, her face only an inch from his cock, with just a thin piece of fabric between. She giggled as Brad's cock twitched under her hot breath. No longer able to restrain herself, Lynn yanked down his briefs, dropping them to his ankles. His hard cock spring forward, lightly slapping her in the face as it bounced free of his straining waistband.

"Oh, I-I'm sorry," Brad apologized, mortified. But Lynn wasn't upset, more than anything she was elated. With his cock leaning against her mouth, Lynn puckered her soft lips, giving the underside of his cock a gentle kiss. Brad shuddered from the sensation, and then let out a small, surprised grunt as Lynn opened her mouth and took in his cockhead.

As they sat in the back of his car, Lynn began to slowly nurse on her son's friend's cock. Lying across the back seat, her head in his lap, she teased his cockhead, sucking softly on the smooth skin, and massaging his balls with her delicate fingers. On occasion, she pulled back to lick the tip, lapping up any dollops of precum he produced, tasting the sweet pearl as it burst across her tongue. Brad couldn't help but let out soft moans as he pushed further and further into Lynn's mouth, grabbing onto the side of the door with white knuckles as he fought back blowing his load in this MILF's mouth.

Finally, Brad thought he couldn't hold back any longer, and was about to warn the hardworking woman of his impending orgasm when she pulled back, dropping his throbbing cock from her warm mouth. She wrapped a loose fist around his shaft, beginning to stroke him slowly as she spoke.

"Honey, tell me, were you being honest earlier?" Lynn's voice was low, but innocent.

"What do you mean?" He responded, feeling the previously-building orgasm slowly subside, his balls unclenching.

"When you said you've never been with a girl before." She stopped stroking, looking up at him from his lap. He had trouble looking down at the mature woman holding his cock.

"Oh, um, I— uh—" He stumbled over his words, embarrassed.

"Bradley," she cut him off. "Are you a virgin?" Her bluntness caught him off guard, and he couldn't help but answer her just as bluntly.

"Yes." He blurted out. Immediately, he felt his face flush red, and wondered if Lynn could see his blushing in the low light.

"Well, Bradley," Lynn began to slowly stroke his hard cock again, slowly, teasingly, with a loose fist. "Would you like me to help you out with that?"

Brad could barely hold back, and again almost shot his load right then and there. This woman had been a family friend, someone he'd known for years. Then, a few days ago, she offered him a life-changing ride home, and now she was offering him something he'd only dreamed of... Though, admittedly, he'd dreamed of this quite a bit. On more than a few nights, Brad had turned off porn to instead imagine Lynn's hand wrapped around his cock, her warm and wet mouth, her soft lips and tongue, and, of course, he'd fantasized about what it would be like to fuck her brains out. Now, as he sat in his car in the empty lover's lane, in the low light of the single street lamp, he looked into the eyes of his best friend's mother as she licked a drop of precum from his twitching cockhead, and nodded.

"Allow me." Lynn rose from the floor, kneeling on the cool leather of the backseat. She bunched up two handfuls of the bottom of her dress, and Brad watched in awe as, in one swift move, Lynn pulled her dress up, over her body, over her head, before balling it up and tossing it to the front seat.

Lynn couldn't help but smile as she noticed Brad's cock throb as he got a look at her near-naked body. Even in the dim light, Brad could tell her tan was even, and his eyes poured over her natural curves. As he'd noticed on their car rides, she had thick thighs and beautiful love handles, with a hint of chub in her stomach. Brad's jaw dropped as he finally got a look at her large breasts, barely covered, pressed together by a sheer, black bra, creating a soft cavern of cleavage. He'd seen her in a bathing suit at one or two pool parties, but had never really paid attention. Lynn reached back and effortlessly undid her bra, letting the straps fall from her shoulders, as the cups smoothly released her heavy breasts. Ina moment of boldness, Brad reached out, feeling his cock twitch in his lap as he cupped one breast in his inexperienced hand, resting his other on her hip. Her skin was soft in his hand, and she cooed to his touch when he grazed her nipple with his fingers. He so desperately wanted to ask to fuck her motherly tits, but chose to hold back, instead letting her take the lead. She was, after all, much more experienced than he was.

"Lean back," she told him. They shifted, and Brad slid down, lying on his back across the backseat bench, still slightly upright with his head against the side of the door. Lynn stood to a crouch, and, as Brad looked on in amazement, slid her panties to her ankles, stepping out of them, until she was completely naked in front of him. Brad drank in the sight of her pink pussy, practically dripping wet from how turned on she was. Lynn loved the feeling of being ogled by this young man, and couldn't help but blush. Regaining her composure, she exhaled, before climbing back onto the seat, straddling Brad. With one hand, Lynn steadied his rock hard cock, and he watched with baited breath as his friend's mom slowly lowered herself onto his cock. His breath hitched as he felt the warmth of her pussy surround his cock, and she couldn't help but gasp as she felt his fat cock push past her swollen lips, through her folds, until she was sitting on his lap, his cock fully inside her.

plushpeach
plushpeach
579 Followers
12