The First Timers Club Pt. 01

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An older man agrees to become a nerdy girl's sexual trainer.
19k words
4.5
25.8k
35

Part 1 of the 10 part series

Updated 06/11/2023
Created 11/26/2022
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Chapter 1 - Meet the Mitchells

I didn't know it at the time, but my life changed the day I met Clay Mitchell.

Clay ran the finance department at Sinclair Land Rover in Fairview. I recalled hovering just outside his office, eavesdropping as he pitted four finance companies against one another, switching between the four blinking lines on his desk phone as if negotiating a deal for a star second baseman. A master hustler of the highest order, he schmoozed and charmed his counterparts, pouring on equal measures of promise and threat, and turned each new concession against the others until one finally cried uncle and gave up the two-point-something rate he'd demanded.

As I sat with him inside his office later, repeatedly scribbling signatures on an endless conveyor of paperwork to complete the sale, I asked about the framed photo of his family sitting on the edge of his desk.

"That sexy lady right there is my wife, Erin, and those are our two girls," he said. He pointed to a blonde girl who looked like a younger version of his wife. "Chelsea's starting her...wow, I guess second year of college now."

The photo must have been a few years old, because Clay looked fitter, with a smaller gut and a little more sandy-colored hair on his head. Erin, an attractive woman in her mid-forties with a voluptuous form, had a head of thick, luxurious honey-blonde hair, and their eldest daughter, Chelsea, had inherited her mother's wavy golden locks, curvy physique, and overall good looks.

Their younger daughter, on the other hand. Well, let's just say she must have dropped from a different side of the family tree and struck a few branches on the way down. A homely, gangly, dark-haired girl with prominent buck teeth and dark-rimmed glasses, she stood awkwardly off to the side in a cringe-inducing superhero pose.

"And who's that?"

"Oh, that's Ashley," he said, but elaborated no further.

Easy going and personable, Clay and I got along like old pals during the hours-long process of purchasing the SUV, and by the time he handed over the keys, it felt like we'd known each other for years. Clay mentioned that he owned the same model Range Rover I'd just bought, which he and his wife took to the river most weekends.

"You should join us," he suggested, and I could tell it hadn't been an empty offer. He seemed a genuine kind of guy. I agreed that it sounded like a good idea, without making any specific commitments, and forgot about it almost as soon as I drove off the lot.

A few days later, I received a text message from Clay asking if I had plans that weekend. They were going to float the river with a few friends. I recalled the picture of Erin I'd seen on his desk, and I had to admit that the prospect of seeing her in something form fitting intrigued me, so I agreed to go.

We met mid-morning on a cool, clear day at a small, dirt parking lot adjacent to a narrow dirt road. When we exited our vehicles, the Mitchells greeted me like we were old friends. Despite my excitement to finally lay eyes on Erin, however, I couldn't help but feel disappointed. She'd put on a lot of weight since the photo, and it really showed on her short frame. Her hourglass figure and narrow waist had been replaced by bulging love handles and a pronounced belly. Her face had changed as well. Fuller cheeks, almost jowly, and puffy bags under her eyes. Her impressive bustline, however, had swelled with her weight gain and stood out, even under a loose t-shirt.

The parking lot would be our end point. We left two cars behind for the return trip and loaded everyone into the two Rovers to drive upriver. As we unloaded our gear and prepared for a day on the water, Erin removed her shorts and t-shirt to reveal a daring two piece bathing suit. She may have been overweight, but she didn't appear to be self-conscious about it, nor shy about showing off her plump body.

I removed my shirt and threw it into the back of the SUV, taking a moment to apply sunblock to my face and torso. From the corner of my eye, I noticed Erin checking me out from behind her dark sunglasses. When I turned my head, she pulled her glasses down and lifted her lips in a playful smile. I kept myself in decent shape, lifting and running several times a week and, as a result, looked and felt better than men half my age, and Erin seemed to appreciate the effort.

I got to know the Mitchells and their friends as we drifted down the lazy twists and turns of the slow-moving river in a small flotilla of innertubes and coolers. Along the way, we swapped stories and shared beers and a variety of potent edibles. Clay proved to be a mellow, fun-loving alcoholic who sported the broken blood vessels and pregnant gut one earns from a lifetime of binge drinking, and in no time he'd polished off a six pack and a small hip flask of Fireball. Erin, on the other hand, was a flirtatious and uninhibited blonde with a fondness for illicit drugs, who became louder and more gregarious the more fucked up she got.

Clay and Erin had been high school sweethearts, and their story sounded like something from a movie. He'd been a four-letter varsity athlete, she the head of the cheerleading squad, and they'd been voted the king and queen at their senior prom. They'd been, by their own account, the two most popular kids at their school. Clay went on to earn a finance degree on a football scholarship and started work at Erin's father's Land Rover dealership immediately after college.

Their eldest, Chelsea, had followed in her mother's footsteps. She'd led the cheerleading squad at the same high school, dated the quarterback, though she hadn't married him, and now attended State where she'd pledged as a legacy at her mother's former sorority. Clay and Erin spoke of her in glowing terms, their pride for her obvious.

When I asked about their other daughter, Ashley, they shared a look and changed the subject.

As the day progressed, the tone of conversation turned overtly sexual. Erin carried on about how often she and Clay fucked, their favorite positions, her love of porn, and the thrill she got from dominating men. She also bragged about the swinger's parties and orgies they'd hosted and attended. After a while, I got the sense that she was either trying to impress me or probing to see if I might be a potential guest for one of their adult functions.

From the reaction of her friends, it became clear that Erin's boisterous and bawdy talk wasn't all that unusual. A few appeared embarrassed by her outbursts, while others simply rolled their eyes, as if they'd heard it all before. From muttered comments, scoffing laughter, and hushed side conversations, I gathered that Erin's legend had become more myth than reality, and that she'd long passed her prime. She was a fat, aging, former homecoming queen whose best days were largely behind her.

More than once, Erin complimented my physique or commented on the contents of my shorts. She touched me often, stroking my arm or leg as we drifted past one another, and she laid in her innertube with her legs spread to give me a view of the area between her thighs. As the sun dipped behind the trees that lined the banks of the river, she became bolder, suggesting that I consider joining her and Clay for a threesome.

By then, Clay had become thoroughly shit-faced, but he acted amused by Erin's antics. In fact, he rather seemed to enjoy it. I suspected that such behavior wasn't entirely unexpected and that he approved of her solicitations. Each time she brought up how much fun the three of us could have together, however, I responded with a smile and quickly changed the subject.

Not that I was completely disinterested in her. After far too many beers and several hours of staring at her half-naked body while raunchy filth poured from her lips, I'd opened up to the idea of fucking her if given the chance. I had absolutely no interest in sharing the bed with Clay, however.

At the end of the day, as we packed up and prepared to go our separate ways, Erin mentioned an upcoming birthday party they planned to throw for their daughter, Ashley, and asked if I would come.

"Yeah, I don't know," I said to be polite, but I knew perfectly well. I hated kid's birthday parties and had no interest in going.

"Come on, man. It'll be fun," Clay assured as he effortlessly hoisted their gear into the back of their Rover. He may not have been in the best of shape, but his athleticism showed in the size of his arms and obvious strength.

"We throw really great parties," Erin insisted, and after the stories she'd told all day, I could only imagine.

"Look, I appreciate the offer, but drinking Kool Aid and listening to a bunch of screaming kids run around a bounce house isn't exactly my idea of fun."

Clay laughed. "Dude, the birthday's just an excuse for the adults to party. Besides, Ash is eighteen, so it's not gonna be that kind of party. A bunch of our other friends are coming. You totally should too!"

"The party's really for us," Erin explained, hanging on his arm. "One of Clay's buddies might even bring some coke," she tacked on under her breath, pressing her finger to one of her nostrils.

"Damn it, Erin," Clay muttered, sounding annoyed.

"What? I said he 'might'."

"Who doesn't love doing lines in front of their kids, am I right?" I joked, and Clay laughed it off.

"Not right in front of them. The good shit stays in the den."

"Oh, just say you'll come," Erin cajoled.

I lied and told them I'd think about it. Then we finished packing our vehicles and went our separate ways. As the week progressed, Clay sent several text messages imploring me to come to their party and, despite my reservations, I finally relented.

Chapter 2 - The Geek Squad

Clay and Erin lived about forty miles away, in a rural area outside of town. When I arrived, several vehicles already filled the front of their heavily wooded property, where colorful, mylar balloons floated from a split rail fence.

Just hang out for a couple hours, have a few drinks, and bail out when everyone's too drunk to notice. It seemed a solid plan.

I found a spot to park and grabbed my backpack and the case of hard seltzers I'd brought with me. Loud music and raucous conversation carried from the backyard, along with the smoky aroma of grilled meat. I found the front door locked. A note directing guests to the backyard, so I made my way around the side of the house.

As I turned the corner, I realized I'd gone the wrong way, but had stumbled upon a group of teenaged girls hunched down by the fence near the AC condenser. I'd surprised them and, when they saw me, they hastily tried to hide whatever they'd been doing.

"Hey," I said.

A well-endowed, red-faced girl discretely blew smoke out the side of her mouth, the pungent scent of marijuana carrying back to me. She looked me up and down.

"Who are you?" she asked, her tone wary. The timber of her voice was low and somewhat raspy. A smoker's voice.

"Just a friend."

She eyed me suspiciously. "Uh huh."

She stood medium height and, like a lot of girls her age, carried a bit of extra weight. Somehow, she'd managed to squeeze herself into a red and white, candy-striped swimsuit that she'd clearly outgrown some time ago. To the point where the tie strings of her bottoms sank into the doughy flesh of her soft midsection and caused her love handles to muffin out. Her strappy top looked equally inadequate to its task, barely able to contain her large chest and forcing her breasts to bulge from the sides.

"Gate's on the other side, right?" I asked, stating the obvious.

She stepped forward and put her hand on my forearm. At first, I'd thought she had a sunburn, but up close I saw that her face was covered in severe acne that carried down over her shoulders and chest. Her short brown hair, a messy, choppy bob with wispy bangs and blonde tips, hanged damp from a recent swim.

"Yeah...um, look, could you do us a favor, guy?"

"Depends on what it is."

"Just don't say anything, okay?"

Her beseeching, wide-set brown eyes were ringed by faint smudges. Evidence of mascara or eyeliner that had bled in the pool. Despite that, and beneath all the skin blemishes, I found her round face to be kind of cute.

"Please," she added, softening her voice.

I found her obvious attempt at manipulation amusing and couldn't help but smile. She didn't need to worry. I wouldn't rat them out.

"Say anything about what?" I asked, playing dumb.

"Dude, come on," she pleaded, not getting it. "Be cool. It's my bestie's birthday, you know?"

Her three friends hung back, waiting anxiously to find out if they'd been busted or not. Only then did I recognize one of them as Ashley.

"Oh shit," I muttered under my breath.

Besides being a couple inches taller than she'd been in the picture on Clay's desk, her body had matured in a remarkably disproportionate way. Above the waist, she looked mostly the same. The same medium-length dark hair and fringe-cut bangs, the same long, horsey face, with the same prominent buck teeth and dark-rimmed glasses, and the same narrow shoulders atop a long, slender torso, with only the barest hint of a bustline.

Below the waist, however, the changes were dramatic.

Gone were the skinny, gangly legs I'd seen in the photo. Instead, her narrow waist flared to wide, contoured hips, with thick, shapely legs and a large, round bottom to match. Her figure looked so outrageously disproportionate that it seemed as if someone had cut and pasted her head and torso onto someone else's lower body

Ashley noticed my reaction and the unusual way I looked at her and she furrowed her brow, appearing confused. I smiled at her and she returned my smile and waved awkwardly, so I waved back. She giggled.

She was high as fuck.

"You must be Ashley, right? Happy birthday," I said, and her smile widened into a buck-toothed grin.

"Thanks."

"Did I hear right that you just turned eighteen?"

Ashley's busty friend moved her hand from my forearm to my tricep and answered for her. "We're old enough," she said, tugging on my arm to regain my attention.

What an unusual thing to say. Then I noticed a scowl flash across her face. She must have clocked the way I'd checked out her friend and decided she didn't like it. Either that, or she didn't want anyone else outcompeting her for my attention.

"So, how about it?" she asked tersely.

"How about what?" I snapped back.

Despite the edge in my tone, I'd returned my attention to her, and that seemed to satisfy her. The corner of her mouth turned up and she rubbed my arm.

"Sorry. I just meant, you're not going to say anything, right?"

Well, I guess that answered the question. She was the jealous type.

"What's your name?" I asked.

"Courtney."

I looked to where the other three girls stood and shrugged my shoulders. "I don't know, Courtney. What's in it for me?"

I'd meant it as a joke, but the blank look on her face told me she hadn't taken it that way. Her eyes narrowed.

"What do you mean?" she asked.

Despite the concern in her voice, she hadn't take her hand off my arm. Instead, she tightened her grip. I decided to have a little fun with her.

"I mean, you want something from me, so what do I get in return?"

She must not have anticipated I'd respond that way, because she stood at a loss for words. After a brief, awkward pause, she responded in a voice filled with trepidation.

"What do you want?"

I raised my eyebrow. What does anyone want? I casually put my hand on her hip, her bronzed skin warm to the touch. The move surprised her, and she flinched.

"I don't know, Courtney. How much is my silence worth to you?"

She stared at me with glassy eyes, scanning my face for the meaning behind my question. Her three friends stood by silently and held their collective breath, waiting for her to answer. I watched Courtney's pot-addled mind turn over as she worked to divine what it was that I wanted her to say.

Before she could respond, I smiled and laughed out loud, startling them all.

"Nah, don't even worry about it. We're cool. You guys want some White Claws before I go in?" Courtney opened her mouth when I held up the case and shook it. "I have, like, a ton."

When she'd finally put two and two together, her face broke into a relieved smile.

"Dude, seriously? I mean, yeah! Fuck yeah!" she said, then added in a more serious tone, "Hey, thanks."

"No doubt," I said with a smile.

Courtney's hand still clutched the back of my arm, and mine still rested on her hip. She held my gaze for a long beat and then did something I never would have expected. She lifted herself up onto her tiptoes and pressed her lips against mine.

Her sudden kiss felt warm and soft but also tentative. When she pulled back, she noted the bemused look on my face. For whatever reason, this must have emboldened her because she went in for another, and her second kiss was far firmer, and more purposeful, than the first.

Without thinking, I glided my hand over her back, then down over the swell of her ass to cup a handful of her exposed cheek. For the life of me, I don't know why I'd done that, and a split second later, when I realized what I'd done, I braced myself for an immediate and forceful reaction. To my great surprise and relief, however, instead of pushing me away and slapping me across the face or screaming, she responded by digging her nails into my back and sliding her wet tongue into my open mouth.

The passion and ferocity of her kiss short circuited the rational part of my brain that knew I probably shouldn't be making out with her. Especially not out in the open and in front of other people. She was young enough to be my daughter. Yet it was the very nature of such a taboo act that excited me and sent a sudden flood of blood rushing to my groin. Courtney responded to my arousal by grinding her pelvis against the growing bulge in my jeans which, in turn, only heightened my desire for her.

Then as suddenly as it began, our lips parted, and we slipped from each other's embrace. Courtney stood still, swaying and staring into space with a surprised look on her face. The hushed murmur of her friends' voices finally broke whatever spell lingered over her senses.

"Woah," she muttered under her breath.

Her eyes fell to the erection straining in my pants and they widened with alarm, but also something else, though I couldn't be sure what. Before she reacted or said something else, I tore open the top of the case and handed her one of the cans.

"You're a really good kisser," I said, and then immediately regretted it. Why had I said that? I suppose I'd wanted to make her feel a little less awkward about the whole episode, but I'd probably done the opposite.

Courtney stared at the beverage dumbly before finally taking it from me, and I couldn't be sure if she'd even heard me or not. Either way, she didn't respond. I passed out more cans to the other three girls and took one for myself. When I cracked mine open, it gave tacit approval for them to do the same. I raised a quick toast to Ashley.

"To the birthday girl."

As we quietly hung out and sipped our beverages, the girls couldn't stop themselves from stealing furtive glances - or outright staring - at the stubborn bulge in my pants. I took the opportunity to return their stares with appraising glances of my own, and I also got to meet Ashley's two other friends.

Kayla was a short, flat-chested girl who wore a perpetually stolid and mercurial expression on her face. Her thick, dark eyebrows nearly connected in the middle, and, like Courtney, she carried a small amount of pudge on her petite frame. She wore her straight, chestnut hair tied up in long pigtails and, in the rare moments she smiled, I spied flashes of metallic and green braces hidden behind her thin lips.