Rags to Reunions - Cover

Rags to Reunions

by Kenny Wright

Copyright© 2011 by Kenny Wright

Erotica Sex Story: In high school, Lily was a shy bookworm, spending more time in the library than at parties. Ten years later, she's blossomed into a successful, beautiful woman. At the reunion, will anyone recognize her? Will the boy who rejected her at prom be there? Only one way to find out...

Caution: This Erotica Sex Story contains strong sexual content, including Ma/Fa   Fa/Fa   Mult   Romantic   BiSexual   Heterosexual   Swinging   Group Sex   Orgy   Masturbation   Voyeurism   School   .

Author's note: This story is hard to categorize. Without giving away too much, it contains straight sex, group sex, voyeurism, a little bit of self-pleasure, a little bit of exhibition, humor, grudges, nostalgia, longtime crushes, memory lanes, and ten years of pent-up attraction between a boy-turned-man and our female protagonist. More than anything, though, it contains love, and for this reason, I file it under Romance. Enjoy!

Lily had her chance to escape it. To resist that seductive draw to revisit a past that she didn't entirely like and flaunt her ugly duckling tale. She could have ignored the letter. The email. The Facebook invitation. Her flight was refundable and she could afford to lose the deposit on her hotel room.

As she stepped off the elevator and headed for the ballroom of the Marriott, she saw them staring -- classmates who couldn't connect the old Lily with the new, dates who wondered why she was there alone. She sauntered through the lobby feeling taller than her 5'2" frame, confident in her short green dress and sparkling clutch purse. Husbands earned elbows to the ribs. Wives vowed to start using gym memberships that had gone idle. And all of it fed an ego that Lily rarely acknowledged she had.

She ran her fingers through her loose, auburn hair, shaking it out around her pale shoulders. She felt the room arch and flex. So did her conviction. This was an unexpected turn on. Until that moment of revelation, she could have left it all behind and gone home. Now, she was caught.

"Welcome back to Good Shepherd High." The woman seated behind the check-in table recognized her, adding a knowing wink to her jaunty smile. "Well, hello there, Lily Noland!"

"Hello, Suzy." Despite the entrance, her enthusiasm was a little stiff. That would improve by the end of the night. Drinks would help. "You look good."

Lily winced at the bald-faced lie, but Suzy seemed to take it in stride. The former editor of the yearbook and president of the graduating class, who'd put on a few pounds, just smiled and said, "You've never been a good liar. You, on the other hand, really do look good." Suzy appraised Lily's slender elegance and Lily felt oddly apologetic. She picked up Lily's nametag, decorated with her senior yearbook photo and current profession (medical doctor), and smiled. "If I didn't know better, I'd say you were an impostor."

Cringing at the black and white image of her former self, Lily asked, "Why the old photos?"

"Oh, please. You know that's why you're here. Now go on and impress."

"I--"

"Go on!" Suzy giggled, sending her through the double doors and into the high-ceilinged ballroom with an extra bounce in her step.

The ten-year reunion of Good Shepherd High School's Class of 2001 was held at the same hotel as its senior year prom. This was done by design. The planners liked the symmetry involved. Two ceremonial nights on either side of their growing years, when teens became adults.

Unfortunately, Lily never made it to senior prom. She imagined what it would have been like, but only after the fact. She imagined going with Jack Waldrup, her childhood friend and unrequited crush. She imagined the dancing, the cheesy photo in front of the muslin-draped backdrop. The virginity-losing later that night.

Jack had taken a better offer: going to prom with the prom queen, Adele Blanchette. And from the way he'd raved about the crazy antics they'd gotten up to after prom, even Lily had to admit he'd probably made the right choice -- from a strictly male teenager perspective, anyway. That was also moments before she'd made him aware of her feelings, slapped him, and told him he could go to hell.

Looking around that room was surreal. She recognized faces but couldn't connect them with names. She remembered little things about them like details from a dream. The guy standing in line at the bar starred in Joseph and the Amazing Technicolor Dreamcoat. The fair-skinned blonde with a toddler clutched in her arms used to smoke cigarettes in the parking lot before school.

The déjà vu fog was universal. It was a speed-dating event with a bunch of people you already knew. The usual questions were asked: what do you do now? how many kids do you have? where do you live now? The inevitable judgments were made: he's going bald already? she's 28 and already been divorced twice? he came out of the closet?

The attention Lily got was also pretty universal. This time, she felt naked under the x-ray assault. Or, at the very least, stripped down to her lacy, ivory lingerie. Many didn't connect the lithesome beauty with the nerdy valedictorian. It wasn't that she was ugly back in school. Lily had always been naturally attractive with her thick hair and unblemished, porcelain skin. She just didn't care enough to accentuate those qualities. She'd never put on make-up until her senior year and hadn't really started to think about clothing style until she was nearly graduated. Ten years of experiences later and she'd swapped out her plastic-rimmed glasses for contacts and had her dark red hair cut to fall in loose, shimmering ringlets around her shoulders.

Lily scanned the crowd, wondering once again why she was here. She didn't have a clique to reconnect with, or even any good friends. As she slipped her green eyes over the familiar-yet-unfamiliar faces, she realized she was looking for one person in particular and hated herself for it. Where was Jack? Maybe he hadn't come at all.

A weird mixture of relief and disappointment filled her when she didn't see him. Nerves a bit frayed, she decided to treat it with alcohol and headed for the bar. She didn't quite make it when she finally ran into someone she recognized without a doubt. Unfortunately, it was the other person she'd been dreading to meet. Adele Blanchette.

"Lily, is that you?" the shapely blonde asked with a salesman-like enthusiasm. When Lily nodded, the blonde embraced her in a hug that completely threw her off balance. They'd never been friends back in school -- the blonde was at the center of popularity and Lily was at the center of nothing -- so at most she'd expected a quiet acknowledgement from the ex-cheerleader.

"I told you it was her," Adele said, turning to the other blonde who Lily hadn't noticed until after the hug. "You look amazing!"

Lily was half hoping that women like Adele would have let themselves go, carrying around the extra pounds of a couple kids and a fat ring that gave them the excuse not to work it off. Adele had no such ring and if anything, she was even thinner, her face maturing into a true Nordic beauty. And her body, showcased in a little strapless pink number, was still intimidating to Lily, despite the pride she had in her own.

When Lily didn't answer immediately, Adele added, "We had a few classes together. I was the dumb blonde." Adele hid her sarcasm well enough to avoid Lily's searching gaze. Girls who transformed this much always came with a complex and Adele's first instinct was to shut them down. But she reminded herself that she was going to be good tonight, and forced a smile.

"Adele! You ... I never thought of you as the dumb blonde." Lily decided to be nice, but they both knew it was a lie. Lily hoped she sounded genuine; Adele let her think she was. "We had Latin together. It's so strange, seeing all these old faces, you know?"

Adele continued to bristle inside. You might look all shiny and new, but you're still the same girl with a chip on her shoulder that you ever were... "Definitely strange to see the old faces." She turned to her companion, who hadn't said much of anything. "Do you remember Morgan?"

Lily did, vaguely. They'd never exchanged so much as a glance back in school, but she seemed nice enough now. "A little. Nice to meet you."

"You, too," Morgan said. "Doctor. Wow..."

"Thanks." She started to return the compliment when she saw that Morgan had left her occupation blank. Not wanting to pry, she simply said, "You look great. Just like your picture."

She realized how silly she'd been earlier. Girls like this didn't let their beauty soften. They'd been so concerned with appearance in high school and that kind of thing didn't just stop after graduation. Take Morgan. Lily was impressed by the vintage '40s look she'd created; it was Katy Perry complete, from the glamour of her wavy, golden hair to the open-toed Seymour Troy Troylings. Even her black dress, while considerably shorter than anything from the actual '40s, had broad, padded shoulders and a cut that emphasized her hourglass figure.

Looking around, though, she did realize that time had taken its toll on most. In the brief silence that followed, Lily added, "I can see that most can't say that."

The titter she got from the two women felt like hot coffee on a cold day and gave her a similar kick.

"Come on, let's get drinks."

"Let's get shots," Morgan suggested enthusiastically.

Turning to Lily with an arched brow and a smile from cheek to cheek, Adele asked, "You in?"

Lily looked from one woman to the other and smiled. Acceptance where she'd least expected it. "Bottoms up!"


A round of Jagermeister and a trio of Cosmopolitans later and Lily was beginning to wonder why she'd worried about coming in the first place. That was when Jack finally showed up. He spotted her first, weaving his way through the crowd. All Lily could do was brace for impact and curse him for still being good looking.

"Lily ... wow ... you look amazing." She was hoping for slack-jawed speechlessness, so his happy-to-see-you smile made her a little upset. How dare he? And then, before her pithy response, his eyes acknowledged his ex-girlfriend and Lily wondered all over again why she was here. "Long time, Adele."

At least her greeting wasn't so chummy.

"Jack, how are you?" The blonde's tone was cool. Lily liked that. It was good to be on this side of the fence.

"I'm good, actually. Moved back to the area."

"You're a teacher?" Lily couldn't help checking out his nametag. She thought of Jack in front of a classroom, talking enthusiastically about Milton or Shakespeare. She always imagined he'd make a good teacher.

"Senior year English lit at Good Shepherd."

"You're a teacher here?" Adele asked, her tone thoughtful. Almost scheming.

"I also look after the library." He looked up at the stage. "And, it seems, I'm to give the welcoming speech." To Lily alone, he asked, "Catch up later?"

Adele answered for her. "We might be able to use you, after all your chores are done." Suzy was on stage adjusting the mic. Lily just shrugged. What she said.

"Jack Waldrup on the reunion planning committee..." Adele shook her head and watched him leave. "I never thought he was such a boy scout."

Lily looked at the blonde, who was still watching Jack's pleasantly fit body ascend the stage, nodding at the band. The Jack that Adele knew was a much different one than the one Lily did.

"Welcome back, Class of 2001!" The murmur of the crowd died down as Jack's amplified voice boomed, proceeded by just a hint of feedback. "Does that feel good? Yeah? Come on, let's give it up for surviving." His clapping prompted applause from the others.

Lily studied him. The cute young man she'd lived just a few houses down from had grown into a handsome young man. The sideburns were gone and his light brown hair was a little more tamed than it had been back in school. The scruff was new, but looked good on him, hardening his otherwise boyish polish. Again she thought of him in front of a classroom, inspiring young students -- the female ones in particular -- with his enthusiasm for iambic pentameter. That charisma translated well to the stage, in front of the returning class of 2001.

"I know what you're thinking: what's that 'ruffian' from public school doing up here, welcoming you back, right?"

Ruffian, really? He might as well have called himself a knave while he was at it. Maybe held up a prop skull for good measure. Clearly Jack was still living a little bit in the illusion of the past. Transferring from public school to a Catholic prep school had certainly earned him a little notoriety, but no one but Jack took it beyond that.

"Well, this ruffian is reformed." Lily rolled his eyes and caught Adele doing the same. Try a little harder, Jackie. "I thought I was hot stuff coming out of here. Got into UC Berkeley. Did pretty well there. Decided to do something in business. Did pretty good at that, too."

"Someone's excited about himself," Adele snickered. Lily laughed with her.

"I don't want to get into it, but circumstances led me back home and I started questioning a lot of decisions I'd made." He paused, glancing around the room. "I took a job here, substitute teaching as I earned my certificate. Now, I teach advanced English lit, and while I don't make what I did in San Francisco, or have quite the same lifestyle, I'm doing what I love, and that's so rewarding."

This was like an AA meeting for those still addicted to their 20s. Even worse, Lily found herself buying into it.

"So I want you to look around. Every one of us has a story to tell -- and most are probably a lot more interesting than mine. Ten years is a long time. I task you all to put aside whatever biases that might still be lingering and get to know the men and women around you. Welcome back and have a great night!"

Applause thundered around him as he hopped off stage. Suzy took his place with some housekeeping announcements that no one cared about.

"He was pretty good," Morgan said, looking to Adele for validation.

She shrugged. "You really think people change that much?"

"Lily did," the Morgan pointed out. The blondes turned to the pretty doctor. Once again, Lily felt naked. She'd gone all out for the night, dressing herself in the slinkiest Italian lingerie she owned and spending the past week in and out of spas and salons. She'd come back not just to prove to everyone else that she'd changed, but also to prove it to herself. How could one flick of Adele's blue eyes discredit all of that effort? And why did Lily care so much?

"I hope we find out..."

Something passed between the blondes and Morgan gave Lily a fortifying look. "I better get back to my husband. He's going to wonder where I got off to."

Morgan and Adele hugged. "I'll find you later when we relocate. I have an idea..." Goosebumps sizzled across Lily's flesh. They were gone as quickly as they came.

"Sounds fun! Nice seeing you again, Lily."

"You, too." Lily lifted her drink to her lips and realized it was empty. She definitely needed to remedy that if she was going to hang with just Adele.

As Lily went to refill her drink, Adele began to form a plan. Being good was getting old fast, and her mind was already working out a way to wrench her from this otherwise boring night. There were other experiences in her past she was much more keen on revisiting than old times with people she didn't care about -- as fun as it was to be fawned over.

Between Lily and Jack, she had a pretty good idea how to do that.


Adele Blanchette was the last person Lily thought she'd be sharing a drink with when she envisioned this reunion. She'd imagined laughter and hugs and what-have-you-been-doings, but looking back on it, when she tried to identify who those people were, their faces came up blank. Adele seemed like as good a companion as any, and remembering the challenge Jack had put forward, she realized that she didn't have much to lose.

"So you're a writer?" Lily asked, reading off the other woman's nametag.

Adele pushed her long, blond bangs out her eyes with the tips of her French manicured nails. "Well, more like a novelist." She swirled her Cosmo in its glass until the pink liquid nearly spilled over the lip. "I write romance novels. You know, paperbacks with covers of hunky, shirtless men, and women with eye-popping cleavage?" She laughed as Lily's eyes automatically dipped to the hem of Adele's dress, where her milky white skin was pushed up into a tantalizing display. Reality mirrored fiction. "I know, shameless. Anyway, I write what's behind those covers."

"Really?" Lily asked, feeling her brows rise into her hairline.

"Uh huh. Turns out I have a knack for writing about sex." This time, Lily shared her laugh.

"I'll have to look you up. You write under a pseudonym?"

Adele nodded, giving her the name as they settled into a table by the dance floor. She was single, although she alluded to being married once in bitter vagaries, and then moving to New York after her first bodice-ripper rose up the bestseller charts.

"So no men in your life?" Lily asked. She'd always been better at asking the questions, rather than answering. Even after she came out of her shell.

"Oh, I didn't say that," the blonde chuckled. "Can't very well write about wild romances and hot sex without some inspiration. I just think relationships are overrated." Lily again thought of the things Jack had described happening after his prom night. Things that involved more than two people. She still hadn't gone that far in her sexual explorations...

"I'll drink to that," she agreed, clinking her glass with Adele. How crazy was this?

"No man in your life?"

"Not anymore."

"Oh, do tell," Adele asked, a glint in her blue eyes.

"Not much to tell." But she found herself telling the other woman her life story like they'd been best friends back in school, not indirect rivals, connected by a boy who they both were over now. Or so Lily thought; Adele had a pretty good idea that Lily was not.

After spending so much of her life concerned with academia, Lily decided to make a change after graduation. She wasn't going to miss out on her college experience like she had high school. She challenged her comfort zones. She joined a sorority. She dated boys. She had casual sex. After graduation, she went to med school, where she ended up falling in love with one of her professors (this earned her a pair of raised eyebrows of her own). That relationship lasted through her residency, until just a couple months ago, when she'd caught Craig sleeping with one of his new students.

"I should have known. Guys don't change."

"No, but they can be fun."


Lily didn't spend her entire night at Adele's side -- just the majority of it. She realized how few friends she had made back then. Seemed like most of the guys she chatted with were more interested in her chest than what she had to say, unless it had to do with getting her room number. And as fun as that was, it got old pretty fast.

Adele's table, it seemed, was the nexus of the whole event. For a social butterfly, the blonde didn't flutter about. People fluttered to her. Lily could practically feel the charisma radiate off of Adele. She realized that simply sitting by her side was ten times as validating as an ex-football player telling her how pretty her eyes were, while staring at her tits.

When Jack came over, Lily pretended he was like any of the other Adele admirers. She resisted the urge to catch up on old times. She didn't even look at him, afraid that that would encourage him.

Jack stayed on his side of the table. He'd hoped that Lily had put the past behind her, but it was pretty clear that she hadn't. She was entitled to that opinion and respected her for that. Together yet apart, they stole secret glances at one another when each thought the other wasn't looking.

And Adele watched the exchange, growing more and more annoyed at the childish behavior. Even when she wrote characters as self-deluded as these two, it irritated her. If you like someone, tell them.

Others joined them. Adele's old gang. Some of the guys had stayed in shape, some had put on weight. No one had a trophy wife. No one had made it particularly big in stocks or start-ups. There were a few other women like Morgan, with no occupations on the nametags, carting around beefcake husbands, but most of the women had turned into mothers and wives she wouldn't look at twice in the grocery store.

And then there was Greg Monroe. Back in school, he'd been a tall and awkward kid, both physically and socially. And although his parents were wealthy, he'd never had the social cred to associate with Adele and her group.

Now, he'd rounded out his height with a body that appeared to fill his tailored black suit well, arrived with a girlfriend who looked like an Italian model, and exuded an air that screamed, 'I belong here and I dare anyone to say otherwise.' Lily immediately identified with that, and despite the aforementioned girlfriend (who was a model, although just one with Italian-American parents), Lily found herself spending most of the evening with him.

She also liked the jealous looks she was getting from Jack when she started flirting with Greg.

"You're on Wall Street? Like those traders who nearly crashed the world's economy?" Lily had had a few drinks in her, but the question had been dying to come out.

"Well, some of my less talented colleagues, maybe," Greg laughed. "The media likes the idea of blanket villainy."

Lily shook her head. Greg was certainly cocky enough to believe that. "Don't you think it's a cultural thing though? One guy makes a risky investment, gets away with it. So now, to keep up, everyone else needs to do it to stay competitive?"

Greg had beautiful eyelashes, dark and full -- enough to make a girl jealous. And somehow, they made everything he said or did ten times more intense than he probably meant it to be. Lily had remembered that back in school, a trait that kind of creeped her out then. Now, it was oddly alluring.

"In a nutshell, you got it." He held up his drink, tipping it until the cubes of ice rattled close to the lip. "But you're placing the blame in the wrong place. You think it's that first guy's fault, when all he did was be brilliant. It's all the followers who fucked up."

"And you're the first guy?" Lily couldn't help the sarcasm.

"Well, I still have my job when so many others don't. Come on, Lily, we're not so different, you and I. We never did anything just because everyone else was doing it." He gestured around. "In high school, that didn't go over so well. But look at them now. They're falling over themselves just to sit with us. This is our time."

Lily took what he said to heart. She was no longer invisible. More than that, she was now a hot commodity. It felt like a victory.


It wasn't long before things became unbearable for Adele. The blonde was over the hollow conversations about what people had done for the past ten years. That's what Facebook and Google were for. She'd already caught up with everyone she cared about, and with the notable exception of Lily Noland, she didn't really care about anyone else.

It was time to enact her plan.

"You know, I'm sad that we didn't know each other better back in school." She'd caught Lily alone, having fended off a drunk whose wife had already turned in.

"I'm pretty sure that even if we did, we wouldn't have been the best of friends."

Adele tilted her head and smiled. And unlike all those practiced ones from before, this was genuine. She surprised even herself when she realized she was actually enjoying Lily Noland's company. It made what she was about to suggest that much easier.

"You're probably right about that. I was kind of a bitch."

"And I had a chip on my shoulder."

"You sure did."

"Hey!" Lily protested. She wasn't supposed to agree with her.

Adele turned to the dance floor, where people were getting bolder as they drank. "I was thinking that later, we could move the party somewhere more exciting."

"What did you have in mind?" Adele watched the excitement climb through Lily's petite body.

"I have an idea, but we need Jack's help." Lily pulled a face. "I know, I know, but it'll be worth it. Thing is, what I have in mind, he'd never do for me. Hell, he probably wouldn't hold the door for me if the building were on fire."

"So how are we going to get him to help?"

Adele's smile set her high cheekbones off. "He won't do it for me, but unless my instincts are off, he'll do it for you..." And as Adele watched her new friend blush, she knew she had the girl.

"So you want to use me."

Adele grinned. "I do, yes. But it'll be fun. Trust me." And maybe you two will stop acting like kids and realize you want each other, she didn't add.

She guided Lily over to Jack, who was looking at his watch, ready to leave. "So Jack, you're in charge of the library now?"

Jack knew something was up almost immediately. Adele wouldn't waste her breath making small talk with him. She had something in mind. "Yes..." he said slowly, half in question.

"And you have keys?"

Comprehension finally dawned on him. "Oh, no. No, no. I don't think so, Adele."

"Please? For old time's sake?" Adele looked over her shoulder. Looked right at Lily. "And if not for me, how about your old friend?"

For the first time that night, Lily was looking right at him, listening for his response. Jack sighed and looked back at Adele. She was biting on the tip of her tongue as she smiled, an expression he recognized: I got you.

He had two options. He could either tell his prissy former flame exactly where she could go and what she could do when she got there, knowing full well that she'd already dug her claws into Lily and would take the sweet young woman down with her. Or he could play along just so he could stay by Lily's side. He chose the latter.

"OK, Adele. For old time's sake. But if we get caught, I'm going to say you ruffied my drink and tricked me into doing it."

Adele batted her eyelashes dramatically and put a hand to her chest. "You forget, Jack, I'm a reformed 'ruffian' now."


Lily felt like she'd been caught up in something. It had snatched her up the moment she walked into that ballroom in her short green dress and spiky heels -- and now it wasn't letting go.

Things were moving faster. In fact, they were literally moving. She was squeezed into the back seat of Jack's little Honda, packed tight enough that she felt her dress ride up her legs and couldn't maneuver enough to pull it down. A whisper of lace peeked out from under the hem, betraying her nude stockings. Greg, crowded in next to her, raised an eyebrow at the discovery and she blushed.

"So what's your story with Jack?" Greg asked as the car pulled out of the hotel's lot.

With Morgan and Mitch in the passenger seat, Greg's girlfriend Vivian in his lap, and Adele squeezed in somewhere on the opposite side of the car, Jack's A/C had to work overtime to cool things down, and that question wasn't exactly helping matters.

"Well, uh..." Lily glanced into the rearview mirror, where she caught Jack watching her before his eyes flickered back to the road. "We kind of grew up with each other."

Greg nodded thoughtfully. "So you were friends in high school? I don't really remember that."

Lily soured. "Me either."

"Oh, come on, Lily. You're not exactly being fair."

"Don't whine, Jack," Lily snapped. "It doesn't suit you." She heard Adele's laugh.

"We grew up on the same street. Went to school together until high school. Lily's parents put her into Good Shepherd. I went to West Fairfield..." Greg watched Lily as Jack rattled off their history like he was a PowerPoint slide. "My parents got divorced. My dad moved away..." Greg's hand climbed up the inside of Lily's knee. Her breath caught. She glanced up at Vivian, who was sitting in his lap, and the woman's roguish smile set Lily's face on fire. She looked out the window, biting on her lower lip. "My little brother started acting out. Got himself expelled..." Large fingers tickled across the inside of her thigh. Streets flew by; familiar houses. She didn't see any of them. "And my mom moved us to private school."

Greg stopped just short of her dress, resting on the lacy edge of her stocking. Lily felt a cry build in her throat. She stopped it before it could escape. "And you were all excited to have a friend move to school with you, but it didn't work like that," Greg said to her.

"No..." It was the only word she could manage, and she was pretty sure she didn't convey the bitterness behind the word. She was too busy thinking about Greg's hand -- or rather, trying not to think about it.

"He thought you were too nerdy for him," Greg finished for her.

"Yes!" There was that connection again. The social rags-to-riches story that they shared.

"Look at you now." Greg's voice made her tremble. He pushed his hand a little higher. The dress receded, unveiling the champagne-hued strap of her garter belt. His dark eyes flashed with approval.

"That's not really fair." His anger seemed more directed at Greg than at Lily. "My life was a mess. When my mom enrolled me at Good Shepherd, I saw it as a chance to start over. New school. New pool of friends. I could be a new me."

The anger finally broke through her heady daze. "You didn't have to be such a douche to me!"

 
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