This story was originally written for the Valentine's Day contest in February 2025.
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CHAPTER 1
This wasn't the first time he encountered a particularly stubborn case in this job. Sometimes he'd have to get really creative to accomplish the tasks laid out before him by his capricious mistress. But as arduous as those past assignments had been, none had challenged his resolve in quite the same way like this young lad right there.
After seventeen hundred years of successful tenure, laboring as Divine Matchmaker under the goddess Aphrodite, for the first time he was seriously pondering whether or not he should simply give up.
"Fate and destiny, she says..."
His whisper trailed into a long and heavy sigh. He curled up in a ball, perching his hunched-over form on the wooden bedpost of his troublesome target. The unerring eyes, with which he could pierce the mortal soul and know its most intimate thoughts, regarded the lanky male before him with the look of jaded exasperation. While these past few moths had seen some progress, compared to how dreadfully this human had carried himself so far, it was still almost inconceivable that any worthwhile female would find him even remotely appealing.
"Too little, and not swiftly enough," he muttered. "Gods! What am I supposed to do with this wretch?"
No answer was forthcoming; the young man, barely older than nineteen, slept peacefully and obliviously. He was completely unaware of the shadowy figure watching him from the corner of his bed. He let out a contended grunt and turned on the side, drawing the sheet up to his chin and burrowing his dark blond head deeper into the soft pillow.
He smiled, enjoying the unusually realistic dream which was playing out in his head. It was one of the many similar ones he had had in the recent times, each exploring much of the same raunchy themes -- and with the same, strikingly attractive young woman. Besides the happy grin on his face, it was causing a lot of excitement to build up directly below his waist. The outline of his hardening shaft was now subtly highlighted by the thin bedsheet that rested over the growing tumescence.
"You're welcome," the figure said mockingly, for such a development could not escape the crafty Matchmaker's notice. With another sigh the unseen shadow straightened up his posture, effortlessly balancing the weight of his ethereal body on just the very tip of his immaterial toe. He then spun around and vanished into the waning darkness of the night, now scattered and dispersed by the first timid rays of sunrise.
The boy stirred again and groaned. He lay on his back now, the taut sheet stretched obscenely over the prominent tent at his crotch. Thanks to his slack arms, which pinned the covers and allowed for practically no movement underneath, the steadily rising erection was meeting increasingly stronger resistance. Before long, the discomfort caused him to wake up and give out a confused gasp, his transition away from the dreamworld as abrupt as it was disappointing.
"Ugh, not fair," he mumbled, squeezing his eyes shut to let the lewd image linger under the eyelids. "Just... a little bit longer..."
He tried to fall asleep again, to chase the erotic scene he'd been pulled out of so suddenly. But he knew it was pretty much a futile pursuit. Once the sexy dream left him -- and carried with it the nubile vixen who'd been featured in it very prominently -- he could be certain that the gorgeous vision wasn't going to return until at least the following night.
Most mornings had been like this now. Every time, the dream would get very intense and excessively carnal; it wasn't unusual that the young man would cum right at the edge of sleep and waking. While he wasn't thrilled about the soiled and sticky sheets that resulted from these involuntary nighttime fantasies, it would be a stretch to say he didn't enjoy the downright pornographic scenes playing out in his mind.
Indeed, more than anything else the teenager was simply puzzled by these recurring dreams. Try as he might, he couldn't even remember when they became such a regular occurrence. What he
did
remember, though, was that each of those erotic dreams would leave him with plenty of vivid memories, an increasingly fervent longing for the object of his desires, and, of course, a straining hard-on.
"Jeez! Guess that was close, huh?"
He groaned again, as he became acutely aware of his pulsing erection. His imaginary slut might've been gone but his urgent need for a release was still very much real. He threw away the covers and exposed his rigid boner, then glanced briefly at the nightstand to read the bright red digits on the clock.
Even for a weekday, it was still very early. He realized that if he wanted to, he had more than enough time to take care of the throbbing problem below his waist. With the lurid images still fresh in his mind, it was hardly a surprise that the horny teenager made the decision to do exactly that.
"Alright then..."
With one hand already gripping his twitching shaft, he reached for a small tub of lubricant that he'd taken to keeping in the bottom drawer. He squirted a good dollop, sighing contentedly as he spread it over his hard cock in a few smooth, very practiced motions. Closing his eyes and exercising his one-track imagination, he eased himself back into the luscious scenery of his dream.
"Ahhh, yes..." he breathed, as he slowly started to stroke his lubed-up cock.
It is a hot summer day. The sun is shining bright above a large backyard pool. Some distance away there is a soft and cushy lounge chair, and a half-naked sex kitten is lying on it all by herself. She notices the strapping young man and smiles, beckoning him with a seductive flick of her finger. He walks towards her with a confident swagger, blatantly ogling her compact but very voluptuous body. She welcomes his shameless gaze, fiddling seductively with a thin strap of her scandalously small bikini.
She licks her lips as he comes closer, wide lustrous eyes fixed on the swaying staff of his erection. He is buck naked, but she doesn't mind it in the slightest. She reaches out and grabs his jutting cock: short, slender fingers wrap tightly around the rigid shaft. He groans, releasing a large volley of pre-cum that lands on her substantial rack. She giggles, watching it soak into the skimpy top which barely covers her impressive round breasts. Deciding she won't need it anymore, she takes off her bra and slides away her equally minimal panties.
She is naked now, too, and with a lusty moan she spreads her legs wide, inviting him into her wet and hairless pussy. He wastes no time as he climbs over the eager vixen, spearing her with his impressive manhood. She throws her head back and cries out in a shuddering orgasm, as the sheer thickness of his cock is enough to bring her to the breathless heights of ecstasy. But it only gets better from there, as he fucks her like a pro for what feels like a blissful eternity, until he finally fills the nearly delirious nymph with a massive load of his seed.
"Fuuuck!" groaned the furiously stroking boy, just as the first jets of semen rocketed from his spasming cock. He came and came, shooting out gobs of thick jizz all over his wiry body. A lot of it landed on the sheets but the wildly cumming boy didn't care. He was savoring the intense release, spurred by the sizzling hot encounter with his stunning but sadly fictional woman.
"Goddammit!" he cursed shortly after he finished, surveying the ungodly mess he just made. "I better clean this shit up... But man, isn't this all just crazy? "
His amazement was probably warranted. As he got up and hurriedly walked to the bathroom, he thought how watching even the hottest, most obscene videos on the internet had never made him cum so hard as he did just now. This imaginary woman, a figment of his dreams and fantasies, was more exciting to him than the sluttiest and most hardcore of porn stars.
