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It's my first day on the job, and my boss has already thrown me in the deep end [F19/M40s] [big dick worship] [blowjob] [masturbation] [wholesome]
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TerriblyEasy is a female or a male in Wholesome
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“You could make pretty good money, you know, spending your summer working at the resort,” her big sister’s best friend Ashley told her last December at a holiday party, “It’s a bitch of a drive down the coast to this place you probably never even noticed, hidden between these big dunes, but rich people love it when things feel secret like that. Makes them feel like they can drop their guard.” She lowered her voice to a conspiratorial hush, “And when they drop their guard, out come the serious tips.”

“But what do you do there, exactly?” Kelsey was too young to legally be drinking beer from the red cup, but that had never stopped her. “Is it, like, lifeguard jobs or something?”

“They have those,” Ashley nodded, “And waiters, housekeeping, clerks at the shops, spa stuff, the like. But none of those are where the big tips are.” She leaned back, curled her lips as if guarding the juiciest secret.

Ashley’s tits, cutely displayed in her tank top, were enormous, and Kelsey raised one cynical eyebrow as to the likely source of her ‘big tips.’ But she hid her grin behind her beer and played into Ashley’s game. “Ok, so, where’s do you make the cash?”

And Ashley was of course eager to flaunt her experience. “You have to be a caddie, out on the golf course. That’s where all the rich old guys spend their day. And they’re golfing, but it’s not really about golf, of course, it’s about spending a few hours away from their wives, hanging with their friends. You just stand there smiling at them, hand them a golf club every once in a while, keep their drinks topped up, and when you get back to the clubhouse they tip so huge.”

“But I don’t know anything about golf.”

Ashley grinned, looked Kelsey from toe to head, “Girl, you’re pretty, and that’s all they care about. It’s just some harmless flirting, and they’ll warm right up to you even if you’re the biggest ditz they ever met. Those guys aren’t pro golfers, they’re just there to have a good time. So make sure that happens and they’ll love you for it.”

It had been a brief conversation with a girl Kelsey wasn’t close with, but the advice had stuck with her. Older guys are shameless in their comments already, Kelsey figures, and turning getting hit on into money sounds like a lot better deal than her previous plan of working a register at the mall food court again. Which is how, come summer, she finds herself in the resort’s uniform of beige shorts and a white polo, driving the hour down the coastal highway to the luxuriously understated property. Parking in the employee lot behind the ugly machinery building, she checks herself in her car’s mirror. A quick flick of her fingers pushes her silky brunette hair back into its deliberately casual fold over her shoulder. A swish of the brush touches up the dark eyeliner and bright eyeshadow she’d put on at home. A short tug on her shirt makes sure her push-up bra has her tits intersecting exactly so with the open buttons of her polo. Perfect, she thinks, for turning some heads, for getting some tips.

“I’m here for my shift,” she announces, walking in through the back door.

“The new girl, huh?” Mary, her boss, frowns. “Took you long enough to get here from the employee gate. Don’t do it again. I got a line of nice old ladies out there, clamoring for service. They told me you’ve worked register before. Well, this one ain’t so different. Show me what you’re worth.”

Kelsey had applied to be a caddie. Yet despite what Ashley said, the management did in fact care that Kelsey doesn’t know the first thing about golf. “But… you’ve got the look,” the hiring agent said, the woman nodding at Kelsey without once looking her in the eye, “You could apply to transfer to being a caddie, after a few months proving yourself of course.”

Kelsey deflated. “Doing what, exactly?”

“Spa attendant.”

“Spa…?”

“Mary’s the manager over there. She deals with some of our top clientele, and she’s always looking for new assistants to manage bookings and retail. You won’t have to actually rub lotion on any old ladies, most of the time.”

Kelsey tried to stay hopeful. “If I did, do they tip well, at least?”

“Stingiest bitches you’ll ever meet,” the hiring agent shook her head, leaned in close and conspiratorial. “You want my advice? Tell them about a guy you’re screwing. They love that, even if you’re making it all up. Maybe you’ll get one of them to open their wallets, if you make them think you’re using the money to buy clothes and makeup and stuff to get with a dude.”

But that actually is what she was using the money for. Kelsey sighed. She almost turned down the job, but when the hiring agent named the pay rate, she had to cough to cover her excitement. “Yeah, I think…” Kelsey started, “I think that’ll work for me.”

When Kelsey steps out from the spa office, she sees a familiar landscape. No matter how organic and peaceful a store pretends to be, it’s still a store. Plastering a false smile across her face, she approaches the register and nods at the customer waiting there. The spa’s shop is dim with curved walls and brightly lit merchandise, a meticulous disarray of shelves filled with salts and sundries and ointments and ornaments. Pinkish warm tile and low-playing music lend ambiance. Stuffy aromas from essential oils thicken the air. A few geriatric women mill about in the gift shop, pawing over overpriced healing crystals and handmade soaps. A frazzled-looking masseuse is engaged in some heated discussion with another old woman. The phone is blinking with a call on hold. And a feisty-looking woman glares at her from the other side of the counter. “Can I help you?”

The customer wrinkles her eyes in disgust. “That remains to be seen.”

It’s nerve-wracking, pretending she knows what she’s doing, but Kelsey perseveres. She, somehow, makes it through her first hour, figuring out how to check the old ladies in for their appointments, ringing up their balms and candles, bumbling through the reservation system, changing appointments, canceling appointments, answering a question about how to turn on an infuser (her mother has the same model), even talking the disgruntled massage client into backing down and earning the thanks of the masseuse.

At last, when Kelsey can finally breathe again, she sighs, “Fuckin’ hell.”

“Tough day?”

She looks up to trace the voice, is surprised to see a man sitting on the low wooden bench lining the wall opposite the counter. Somehow, despite his large size, he’d blended into his surroundings, made his presence fail to record itself in her awareness. And now Kelsey realizes that he’s been looking at her for some time, gaze heavy, grin wry and impersonal.

She almost chokes on her own tongue. “I’m sorry!” The man’s middle-aged, tan, clean-cut, wearing a golf shirt and golf pants, and looks to be as broad across as a Kelsey is tall.

“Got a three-forty-five salt treatment,” he says, his gaze unwavering, his voice as big as his shoulders.

“Um, that’s, um, ten minutes ago?”

“You were busy,” he offers, “I didn’t mind waiting. But seeing as that things’ve now calmed down some…” He nods towards the hallway which leads to the treatment rooms.

She jumps nervously, picks up the handset to call Mary. “Oh, of course, sir. All of the, um, technicians are not available at the moment, but, um–”

He stands, says, “I know where it is.”

If his broad shoulders intimidate Kelsey, his great height only doubles the effect. Hand shaking, she sets the phone back down and comes out from behind the counter. “Still, um, I don’t think I’m supposed to let you back unescorted. So, err, if you’ll please follow… me?”

The intense way he’s studying her only makes him that much more imposing, his silence doing nothing to lessen his presence. Men like him smile at her all the time, make passes at her, leer at her. But this is different. His interest in her is more… disciplined. It makes her tingly.

“Err, yes, well then,” she babbles and leads the large man down the dim, wood-paneled hallway. “How was the golf today, sir?”

“Bad.”

Kelsey gulps. She guides them around the corner to the salt rooms, and holds open the door for him to room two, biting her lip to suppress her nerves. “There’s, um, supposed to be a changing area here,” she points, “And they say that the more of your skin–”

“I know,” he says, his bassoon temblor resonating against the moist, salty air, “I’ve done this before.”

“Oh, right, yes!” she stammers, “Well, um…” Tracking him with her gaze, she sees his immensely wide shoulders surge with muscle as he pulls his shirt off. He squats on the wooden bench to remove his shoes and socks. “Uh, anything else, sir?”

His eyes narrow. “Looking for a tip?”

“No, um… I mean…” The words stumble from Kelsey’s mouth, her footing lost, her brain failing to function properly. The man has unbuckled his belt, and as he slides his pants off, she drinks in the thickest, most muscular thighs she’s ever seen, taut and tan. Without realizing she’s doing it, her gaze slides to his crotch, to the tight black underwear wrapping around his seriously significant bulge.

He watches her ogle him, and she knows his eyes are dissecting her, picking her apart piece by piece, seeing through her insecurities and anxieties and uncertainties for the naivete they are, but she just can’t stop. His age lends him an iron-cored self-assurance that Kelsey’s never before encountered, a composure that exudes from his very being.

She should leave, she knows. She should close the door behind her, escape back to the store, forget this ever happened. Or at bare minimum, she should stop staring at his crotch.

But she can’t. It’s mesmerizing her, the immutable evidence of a huge shaft pressing out into the fabric, the swells beneath which can only be a massive pair of testicles. “I, um… I should…”

He watches her, his face impassive, his demeanor calm. “I prefer to be entirely nude in here,” he says, reaching for the underwear’s upper band.

“Oh! That makes sense. It’s, um, good for your skin and all… um…” This is her cue, she knows, but still she doesn’t leave. She can’t, and she doesn’t know why.

No, that’s not true, she does know why. As she watches the big man push his underwear off, she knows exactly why. Because, just like everything about the man, his dick is by far the biggest she’s ever seen. The most potent symbol of male virility she’s ever witnessed. The most shockingly robust totem to masculinity she’s confronted in her nineteen short years.

The salt room is quiet apart from the low hiss of the fans and the quickening breath of the young attendant. Her chest is heaving, her pussy is wetting, and Kelsey knows she’s breaching some uncrossable boundary just by being here. But the big man resting on the wooden bench doesn’t object, doesn’t say anything at all. He just spreads his legs, relaxes against the wall behind him, and stares at her, daring her to make the next move, yet unconcerned whether or not she does.

“Are you, um…” her words trail off, another nervous sentence abandoned, its destination unknown even to herself.

The man continues his campaign of silence.

His dick rests between them, long, thick, mostly limp but not entirely. It twitches, pulses thicker.

“Um…” she says again, watching his cock unaided grow slowly towards erection. His balls cling heavy at the base of his shaft. His tip swells shiny bright red. Kelsey licks her lips, shifts her weight to her other foot, grinds her thighs against each other. She’s become numb to the shame of ogling, her stare taking on a wanton lust as she imagines what a huge penis like this must feel like to touch, how fulfilling it must be to ride to climax, how rewarding it would be to give it the pleasure it seeks.

So Kelsey accepts that it is inevitable as she drops to her knees between the big man’s legs, wraps her fingers around his incredible girth.

Although his dick surges in her touch, he defies her expectations by otherwise reacting not in the slightest. He simply watches her, watches this young woman fall hypnotized by his manhood. Nor does he react when her hand begins stroking up his length, gripping him in her fist, cupping his swollen balls in her palm.

The mammoth penis strains out from his hips like an appendage all its own, thicker around than her wrists, as tall as her forearm. Kelsey massages it, slowly at first, anxiously, but growing in assurance when nothing bad happens. She wants more, knows that simply yanking him is insufficient. So she twists her hands as she strokes, teases his vein with her painted fingernails, cups and toys with his balls, runs orbits around his glans with her thumb.

Her boyfriends would be long moaning by now, would be painting her face white with their cum, yet this man says nothing, reacts only by staring deeply at Kelsey. If he savors her cute eyes, he doesn’t say. If he enjoys the sight of her cleavage, he doesn’t let on. Only the swelling stiffness of his dick betrays any appreciation for what Kelsey’s doing.

When a bead of precum surges out and courses down its under side, Kelsey automatically leans in to lick it up. And from there, she keeps licking. Fist pumping his base, she uses her tongue to coat his shaft in her spit, to lap at his balls, to tickle his tip. Only when she purses her lips and takes his bulging fat head into her mouth does he shift his jaw, suck in a quiet breath.

And that small morsel is all the encouragement Kelsey needs. Stroking him with renewed vigor, she sucks on the tip, taking his massive meat into her mouth as far as she can without gagging. She slurps down his salty arousal, breathes in his intoxicating scent, stares him in the eye.

He is, of course, unflinching, as steady as a ticking clock.

When she sucks his balls into her mouth, tugs on them with her lips, she doesn’t know what’s overcome her. She’s never done anything like this before. Never fucked a stranger, never been with an older man, never had a partner who seems no closer to cumming despite all she’s doing to please his dick.

And yet, she needs it. From the moment she saw this man, she felt the need to give herself to him. And his penis was love at first sight. She knew she could have it and she knew she’d forever regret it if she didn’t. And so as she returns her mouth to the head of his massive shaft, she sucks him with a devotion which comes naturally to her and strokes his girth with an enthusiasm she doesn’t have to feign.

It shows in her eyes, the energy passing between them. Kelsey knows that for all his impassiveness, that she’s pleasing him how he likes, that her attentions are well-received.

So she sucks like a devotee, her head bobbing at his crotch, her fists tugging and squeezing with muscles quietly straining. She’s rewarded with another surge of precum, one which she instantly sucks clean, swallows down.

When her hair knocks loose, she tucks it back into place. When spit drips down her chin, she wipes it away. When she feels her tongue grow tired, she ignores it.

Grinding her thighs together in a fruitless attempt to satiate her own deepening arousal, she sucks and sucks and sucks. Well past amazement at the man’s stamina, she is determined to keep blowing him as long as it takes, to keep going until–

His jaw clenches, his hand tightens on her wrist. And like that, he’s cumming. His mighty balls tighten against his shaft and Kelsey’s mouth fills instantly with semen. She swallows, but it keeps coming, blast after blast of his seed, his orgasm continuing on, until finally it’s merely oozing from his bulging dick.

Kelsey pulls her lips away and wrings empty the last drops onto her outstretched tongue, watching the big man relax against the bench, lean into the wall behind him, seeing the relief wash over his face.

“Um… ok…” Kelsey says as she sits back, realizing she wasn’t as tidy about his spunk as she thought when some drips from her chin and onto her hand. “I, um…” she stammers, glances again at the man, seems him looking back just as impassively as ever, his dick resting limp and red against his belly. “I should, err…” She should leave, she knows.

But she is so fucking turned on, and simply squeezing her legs together isn’t cutting it. Squatting before the man, watching him watch her, she slides her hand into her shorts, slips her fingers beneath her panties, and flicks her clit until she’s moaning with orgasm.

The beginnings of a smirk have curled the man’s lips. “You’re new here, aren’t you?”

“Uh-huh,” she pants, trying to regain some sort of composure.

He breaks into a rare grin. “You’ll do well. You run along now, before Mary misses you.”

Mary! Oh no, Kelsey panics, scrambling up, scampering for the door. Mary is of course frowning, but she apparently doesn’t expect much from a lowly new girl, because Kelsey gets no reprimand.

But the next day, when she arrives for work, Mary is waiting for her. “You made an impression, Kelsey.”

“Oh no! Am I fired?”

“Fired? No, girl. Mister Crenshaw heard you had applied to be a caddie, and now he’s asked for you by name, said he would train you.”

Kelsey is in disbelief. “Mister Crenshaw?”

“The man you helped yesterday? He’s our biggest client. And he’s not an entitled jerk like some of the others, but he’s definitely hard to impress. Yet, somehow, you managed. So get your ass over there before you let him down before you’ve even started.”

Kelsey nearly scampers across the property, flying through the hallways and down the winding paths as quick as dignity will allow. When she arrives at the golf clubhouse, she’s out of breath, and the big man is already perched on a cart. Golf clubs lay behind him and he’s dressed in a smart golf shirt and pants, one amused eyebrow raised.

“Mister–” she sucks down a breath, “Mister Crenshaw?”

He grunts. “Kelsey.” Sitting back in his seat, he spreads his knees deliberately, makes her breath catch, makes her eyes slide to his crotch. Not unfriendly, he pats the empty cushion next to him. “Let’s get started, shall we?”

She sits. His hand curls around her knee as his foot presses the pedal, and as the cart zips off, the dragging of his rough fingertips against her soft bare thigh send tingling shivers up her body, making her cheeks blush, making her pussy warm. “Whatever you need, Mister Crenshaw,” she says, “I’ll do for you.”

“I’m sure you will, Kelsey. I’m sure you will.”

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