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From Overworked Salaryman to Harem King: My Ridiculous Second Life

DJgameing
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Synopsis
Title: From Overworked Salaryman to Harem King: My Ridiculous Second Life in a Fantasy world Genre: Isekai / R18 Comedy / Harem / Action / Slow-Burn. Synopsis Leon Arkwright, a 21st-century corporate slave who literally died from overwork, wakes up reborn in a medieval fantasy village with all his memories intact. Now a handsome 20-year-old orphan with zero game and one idiot best friend (Rowan “Row” Calder). Fate, of course, has other plans.
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Chapter 1 - My name is Leon Arkwright.

I died in my previous life from sheer overwork, only to be reborn in a medieval fantasy world with all my memories intact. I was born into a quiet little village on the edge of the kingdom. When I was twelve, both of my parents—accomplished adventurers—were killed by a monster horde while out on a commission. The loss crushed me; they had been loving, wonderful parents, and for an entire year I could barely function from the grief.

Because both of them had been orphans themselves, I had no other relatives to take me in. Thankfully, they had left behind a modest house, some savings, and a few valuable pieces of gear. With careful management and odd jobs around the village, I managed to survive on my own.

Eight years have passed since that tragedy. Today, on my twentieth birthday, I am officially an adult in the eyes of the kingdom, I stand at the threshold of my own adventure, ready to carve my name into this dangerous, beautiful world.

Leon was heading toward the forest's edge to gather medicinal herbs, the same quiet spot he'd used for years. He set his basket down and began carefully plucking the silvery moonleaf that grew in abundance here.

A faint rustle from the nearby bushes caught his attention. Curious, he crept closer and parted the leaves just enough to peek through.

There, in a small sunlit clearing, stood a beautiful woman he recognized from the village: Elara Veyne, a thirty-year-old widow whose husband and young children had tragically perished in a monster attack five years earlier. She lived alone on the outskirts now, rarely speaking to anyone.

Unaware she was being watched, Elara had hiked up her skirt and squatted to relieve herself. From his angle Leon caught a fleeting, accidental glimpse of her bare skin—soft pink folds glistening in the dappled light—before heat rushed to his face and lower. His cock gave an involuntary twitch, a bead of pre-cum dampening his trousers. He felt a stab of guilt for not looking away immediately, but the sight rooted him in place for a heartbeat longer than it should have.

Elara finished, smoothed her skirt down, and stood. . . started walking straight toward the exact patch where Leon had left his basket.

Panic snapped him out of it. He scrambled back, snatched up his basket, and dropped to his knees, pretending to be deeply focused on harvesting herbs just as her footsteps crunched into the clearing.

She stopped a few paces away, seemingly oblivious to what he'd just witnessed.

Elara smiled warmly when she saw me. "Good morning, Leon." 

"Good morning, Miss Elara," I answered, trying to keep my voice steady.

She set her own basket down a few paces away, then crouched to gather moonleaf just like I was doing. The neckline of her simple linen dress gaped slightly as she leaned forward, offering an unintentional but generous view of the soft, full curves of her breasts. Lower still, the hem of her skirt had ridden up just enough that I caught another accidental flash of the delicate pink folds between her thighs, still faintly glistening from moments ago.

Heat surged through me. My cock stiffened instantly beneath my trousers, the thick ridge impossible to hide in the snug fabric. I shifted, trying to angle my body away, but it was too late.

Elara's eyes flicked downward for a heartbeat. Her lips parted in a tiny, surprised gasp. A visible shiver ran through her; her cheeks flushed crimson, and a fresh bead of arousal slipped free, darkening the fabric between her legs just a little. She pressed her thighs together, but the motion only made the damp patch more obvious.

Our gazes locked. Neither of us spoke, yet the air between us crackled with sudden, undeniable hunger.

We finished filling our baskets at almost the same moment. Elara straightened, brushed a strand of auburn hair from her flushed face, and met my eyes with a look that sent fire racing through my veins.

"Leon," she said softly, voice trembling with want, "would you sit with me for a moment?"

I nodded, throat dry, and lowered myself onto the soft grass beneath the shade of an old oak. She followed without hesitation. Her fingers brushed my cheek, then trailed down to the laces of my trousers. I lifted my hips to help her, and in seconds my cock sprang free: thick, veiny, already aching for her.

Elara gathered her skirt to her waist, revealing the slick, glistening folds I'd glimpsed earlier. She straddled me slowly, deliberately, guiding the head of my cock to her entrance. With a shared, breathless look of permission, she sank down in one smooth motion. I slid into her tight, welcoming heat until the tip kissed the mouth of her womb.

A low, throaty moan escaped her lips. She wrapped her arms around my neck and held perfectly still, keeping me buried to the hilt, our bodies locked together.

"Don't move yet," she whispered against my ear, her inner walls fluttering around me. "Just… stay right here inside me."

She pulled back just enough to gaze into my eyes, pupils blown wide with desire, and asked in a husky voice:

"Leon… may I have all of you?"

Elara stayed perfectly still on my lap, my cock buried deep inside her pulsing heat. She cupped my face with both hands, her emerald eyes searching mine, voice low and serious.

"Do you know why I'm doing this with you, Leon?" she asked, a faint smile playing on her lips. "Answer honestly… and if you're right, I might just decide to become yours for good. Answer wrong, and we pretend this never happened. I walk away, and you let me."

My heart hammered. The only thing my lust-fogged brain could come up with slipped out before I could stop it.

"B-because… I have a big cock?"

The moment the words left my mouth I knew I'd failed.

Elara's expression softened into something between pity and disappointment. She let out a quiet sigh, lifted herself off me in one slow, deliberate motion (my slick length sliding free of her warmth), then smoothed her skirt back down over her thighs. Without anger, without another word, she picked up her basket and walked away through the sunlit grass, hips swaying gently, leaving only the faint scent of her arousal and crushed moonleaf behind.

I sat there beneath the oak, trousers still around my ankles, cock cooling in the breeze, feeling like the biggest idiot in the entire kingdom.

Elara walked away, hips swaying, still flushed from what had almost been.

Halfway down the forest path she crossed paths with my best friend (and fellow twenty-year-old orphan) Rowan "Row" Calder. Row, never one to read a room, spotted her and flashed his usual cocky grin.

"Damn, girl, that's one hell of a fat ass!" he called out, loud enough for the birds to hear.

Elara stopped dead. Her face went perfectly blank. Then—CRACK!—her open palm cracked across his left cheek like a thunderclap. Row spun, stumbled, and ate dirt in one spectacular motion.

She didn't even break stride, just kept walking.

A minute later Row scrambled up, rubbing his stinging cheek, and spotted me still sitting under the oak—trousers around my ankles, cock out in the open, staring into the void like a lost puppy.

His eyes went wide. He sprinted over, dropped to his knees, grabbed my shoulders, and wailed at the top of his lungs:

"Brother! Leon! What did that demon woman DO to you?!" 

Tears and snot everywhere. Actual waterfalls. 

"She—she violated you, didn't she?! My poor innocent brother! Who's gonna marry you now?! Your purity—gone forever!"

He sobbed like the world was ending.

I blinked twice, sighed, and delivered a mirror-image slap across his right cheek—BANG. Row kissed the ground again, symmetrical handprints glowing red on both sides of his face.

He lay there clutching his cheeks, looking up at me with huge, teary, betrayed eyes like a kicked chick.

I stood, pulled my pants up, and dusted myself off.

"Come on, idiot. We're going home to finish sorting the herbs."

Row sniffled, wiped his face on his sleeve, and nodded rapidly like a baby chicken pecking rice.

"Y-yessir…"

We barely made it ten steps before Row started hounding me like a clingy girlfriend who just found lipstick on my collar.

"Spill it, Leon! What really happened back there?!"

I sighed and gave him the short, embarrassing version (the peeking, the almost-sex, my legendary dumb answer, Elara walking away).

Row listened with growing horror. When I finished, his face turned tragic, eyes welled up, and he actually started bawling.

"B-bro… when we were kids you promised! You said brothers share everything!" 

He flopped onto the grass, kicking his legs like a toddler. 

"Hoes before bros, man! You got to third base with the hottest widow in the village and didn't even save me a turn? I'm wounded! Betrayed! My heart is broken!"

He rolled around, fake-sobbing loud enough to scare squirrels, while somehow still stuffing moonleaf into his basket.

Ten minutes of this nonsense later I finally bribed him to shut up.

"Fine, fine! Next time we find a girl who's into both of us, we share. Deal?"

His tears vanished instantly. He sprang up, wiped his face, and punched my shoulder with a huge grin.

"Deal! Pinky swear on it, bro. Now let's go sell these herbs before the apothecary closes."

Sniffling one last dramatic sniff for effect, Row slung his basket over his shoulder and marched beside me toward the village pharmacy like nothing had happened.

Row pushed open the pharmacy door and we stepped inside. The front room was empty, the counter unattended.

"Guess we wait," I shrugged. Row nodded, already fidgeting.

Two minutes later he was bouncing on his heels. "I'm bored." Before I could stop him, he wandered toward the half-open storeroom door at the back.

He froze. I walked up behind him and looked over his shoulder.

There, on a thick wool blanket spread across crates of dried lavender and valerian, were Elara Veyne and the village pharmacist, Mira Thorne (both gorgeous, thirty-something widows everyone in town quietly lusted after). 

Mira's blouse was tugged down just enough to free her heavy breasts; Elara's skirt was bunched at her waist. The two women were locked in a slow, hungry kiss, tongues sliding together, soft moans muffled between their lips. Elara's fingers pumped steadily between Mira's thighs while Mira returned the favor, three slick fingers curling deep inside Elara, thumb circling her swollen clit in tight, practiced circles. Their hips rolled in perfect sync, breasts pressed together, nipples grazing with every breath. The air smelled of crushed herbs and raw arousal.

Row's jaw hit the floor. Mine wasn't far behind.

The women finally noticed us. Elara broke the kiss, cheeks flushed crimson, but she didn't stop the slow thrust of her fingers. A sheepish, wicked smile curved her lips.

"Well," she said breathlessly, glancing at me, "looks like someone finally figured out the right answer after all."

Mira laughed low, gave Elara's clit one last teasing flick that made the younger widow shudder, then gracefully withdrew her hand. She stood, straightened her blouse (not bothering to button it yet), and sauntered over to the counter. She weighed our baskets, and slid one shiny copper coin to each of us.

"Shop's closed for the afternoon, boys," she purred, eyes sparkling with amusement.

She ushered us gently but firmly toward the door and flipped the sign to CLOSED.

Row and I stood on the street like a pair of kicked puppies.

Row recovered first.

"Hey!" he called through the door, "at least let us watch the encore!"

The only answer was the soft click of the lock and two sets of muffled, delighted laughter from inside.

A few minutes of standing there like idiots was enough.

I sighed. "Come on, Row. Let's hit the brothel. At least someone there will take our money."

Row perked up instantly. "Now you're speaking my language!"

We stopped at the bakery first, spent our two hard-earned coppers on a couple of still-warm honey loaves, then headed to the eastern edge of the village: the Lantern Quarter, better known as the Red Veil.

The whole street glowed soft pink and gold even in daylight. Paper lanterns hung from silk cords, music and laughter spilled from open windows, and the air smelled of jasmine, spiced wine, and warm skin. Courtesans in sheer robes leaned over balconies, waving silk fans and calling playful invitations to passers-by. It was loud, colorful, and shamelessly inviting.

At the very end of the lane stood the biggest establishment in town: the Crimson Lotus Pavilion. Three stories tall, painted deep red with black lacquered beams, golden lotus flowers carved into every doorframe. A wide veranda wrapped all the way around, crowded with plush cushions and low tables where clients smoked hookah and drank plum wine while beautiful women and handsome men kept them company.

We pushed through the double doors and stepped into paradise.

Inside was pure sensory overload: low amber lighting from crystal chandeliers, thick burgundy carpets that swallowed every footstep, the constant thrum of a lute and a sultry singer somewhere deeper in. Perfume, sweat, and sweet incense hung heavy in the air. Half-dressed courtesans glided past like living works of art, laughing with clients on velvet couches.

Row and I marched straight to the long mahogany counter at the back.

Behind it, asleep, head pillowed on folded arms, was the madam everyone simply called Lady Seraphine. Easily in her late thirties, she was the most stunning woman either of us had ever seen: long silver-white hair cascading over one shoulder, full crimson lips, and a deep violet robe that had slipped open just enough to reveal an absolutely sinful amount of cleavage. One long, shapely leg was stretched out on the stool, the slit of her robe riding high on her thigh. She looked like a goddess who'd decided to take a nap in the middle of her own temple.

I cleared my throat and gently shook her shoulder.

Seraphine's golden eyes fluttered open. She took one look at us, yawned delicately, and smiled like a cat who'd spotted two particularly entertaining mice.

"Ahh, my favorite little brothers," she purred, voice warm and smoky. "Right on time."

Before we could say a word, she slid two brooms across the counter.

"Second-floor hallway and the Sapphire Suite need sweeping. Get to it, sweethearts."

Row and I stared at the brooms, then at each other.

We bowed politely, took the brooms like the broke twenty-year-old virgins we were, and shuffled off to start cleaning.

Some dreams, apparently, come with chores attached.