My intimidating co-worker made me into her boytoy [M24/F38] [redhead] [seduction] [oral sex]

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This is back on my first company trip I ever took, when I am only a year or two out of school. I’m in a hotel in Cincinnati I think, or maybe Cleveland, or Columbus? One of those Ohio cities that starts with ‘C,’ at some industry conference. I’d spent all day withering away in front of our exhibit, my lanyard chafing my neck while my starched shirt scratched my shoulders, unable to gather any serious interest from the attendees. I’d spent twelve hours failing in every regard to be the successful go-getting buoyant company development professional I keep telling my business I am, and I slink upstairs to my hotel room. The heavy click of the door sliding closed reverberates and for the first time since waking, relief descends, a full-body sensation. Safe and sequestered from the misery of social interaction, I feel my shoulders droop and forced grin relax and face go slack.

My suitcase lays knocked over beside the bed, a note of welcome from the housekeeping staff on the nightstand beside it. I kick off my shoes and, still in my company attire, collapse on the bed. My head bounces off a rough and uncomfortable pillow, a decorative blue-green square with tassels, and I yank it out from behind me, holding it over my face. I scream into it, a litany of curse words and frustration.

When I get it all out, I slowly realize someone is knocking on the hotel room door. My weariness returns in a flash, and I whimper to myself as I roll off the bed and past the bathroom. I lean into the door, peering through the peephole. I swallow a groan.

It’s my co-worker, Kathy Kaplan, the other half of our business’s delegation to this conference. She’s still got her badge on, still in her clever company suit with dark navy blue jacket and matching skirt. Telling this story now, with the gift of retrospective, I can tell you that she’s clearly attractive — cute, redhead, and busty, so very busty. But back in the moment, in the there and then she intimidates the bejesus out of me, and the fact of her being hot just makes her that much more frightening. She’s not my boss, but as Associate Director of Engineering she far outranks me at the firm. And she’s also a good decade or more older than me, speaking with clients and on discussion panels with a learned confidence that stems from true subject expertise. Her serious demeanor pairs well with the ease with which she navigates technical topics, and my tactic when she’s at the booth is to shut up and get out of her way.

I run my hand across my face, wiping off my misery, placing back on my face the best smile I can manage. It’s not much, but at least I’m not scowling as I unlatch the door and wrestle it open. “Kathy, hey. What a day, huh? You ready to do it all again tomorrow?”

She pushes past me, walking in and eyeing the decor critically, as if I had any choice in its selection, and frowns at my suitcase. She spins around, gaze narrow. “What’s going on in here? I thought I heard you talking to someone, that I was missing the party.”

“Huh?” I can make my innocence look sincere, I’m good at that at least. “Nope. Just me here. Lot’s of weird noises in hotels, right?”

“Right. Whatever.” Doubt shades her face. She clearly doesn’t believe me. “John. We need to debrief, talk about what we’re doing tomorrow, et cetera et cetera. And we also need to eat. Unless you have other plans, that is.”

Confused, I shrug. “No, uh…”

“Good. Grab your coat. There’s a Peruvian place two blocks from here, very chic, getting a lot of attention, you know? I made reservations.”

I do not know. Fine dining isn’t something I have any experience with, and like a schoolboy going on a field trip, I follow behind Kathy as she leads from the hotel to the restaurant.

The wind whips at us, pulling at her hair. But it remains in place, tightly locked down beneath her clips. I shove my hands into my jacket pockets, pulling it in snug, and when we arrive, I hold the door open for her.

“Put your badge away,” she says, pointing at the lanyard hanging from my neck, “You look like a doofus.”

If I look like a doofus, it’s because I am a doofus. I am very much out of my element, surviving only by mimicking Kathy, doing whatever she does. We’re seated at a small table, squeezed in between an array of other small tables, all seats occupied by famous and fashionable people. The lights are down low, the noise of conversation loud, and despite the close proximity of others, I am ignored, nobody notices how unsuitable a patron for this restaurant I am.

“What’s your grape?”

“Huh?” I am wide-eyed.

“Don’t look at me that way,” she says, “This is a business dinner. The company’s paying. Pick a bottle, anything reasonable.” She passes me a stiff sheet of paper.

I study it, and realize it’s the wine list. I don’t recognize anything, I’ve never even seen half these words before. I goggle at the prices — a bottle listed at one-fifty is the cheapest thing on the list, the next lowest is two-twelve. “Uh, the Rhone looks good…” I suggest. It’s two hundred and eighty dollars. I pick it because I’m fairly certain of the pronunciation.

She arches an eyebrow. “Good choice.”

The sommelier opens the bottle at the table, pouring me a sample. I taste it, pretending I have even the slightest idea what I’m doing, and give him a nod. He fills my glass. I sip it, happy to have some scripted role to play.

But the role ends there, and I can’t take the silence. “So, err,” I begin, “For tomorrow, what were you thinking?”

“No, no,” she says, “None of that work stuff at least until we have our food. What’re you thinking of ordering? The spatchcock I’ve heard is the chef’s specialty.”

I don’t know what a spatchcock is. “Uh, yeah, I was thinking of getting that, too.”

The waiter takes our orders, possible and exceedingly professional.

As she walks away, Kathy’s eyes blink up and our gazes meet. The candle on the table flickers, the small shadows it casts dancing and shifting. “So, John. Your first conference. What do you think?” She rests her chin on her hand.

“Uh, it’s fun–”

“Oh, bullshit. You look about as happy to be here as a cow at a hamburger factory.”

My throat drains of words. I cough and manage to stammer, “Is it obvious?”

“Don’t sweat it. Nobody’s expecting you to be anything more than you are. We all have to start somewhere.”

“Oh, uh–”

“Although, I’d appreciate it if you could be a little more familiar with our business, with what services we provide.”

I sip the wine. It’s powerfully rich, thick on my tongue. “Sorry.”

“I don’t want your apologies,” she says, “You’ve got a natural charm. You’ll go far once you get some experience under your belt.”

The waiter sets plates down in front of us, and I am relieved to find that spatchcock appears to be nothing more exotic than a chicken. We eat.

“Who’ve you got waiting for you at home?”

“Oh, uh,” I swallow my bite, “Just my mom and dad, you know.”

Her eyebrows raise. “You still live with your parents? Oh, you sweet child.”

I shrug meekly. “It’s not that bad–”

“But how do you, uh,” as she pauses, an impish grin spreads across her face, “Entertain company?”

I don’t find out her question, not at first. “I don’t… I mean, we just hang out in the living room or whatever.”

She clucks her tongue. “I figured, young man such as yourself, you’d have lots of girlfriends.”

I blush as her meaning dawns, averting my gaze, focusing on eating my food. “I’ve been too busy, with the new job and… everything.” My words sound weak, even to myself.

Her grin spreads. “I’m sure someone will come along.”

The people at the next table over stand to leave, and as Kathy shifts to get out from their way, her leg brushes mine. I’m sure it’s an accident, and I don’t think anything of it.

“Let’s get some dessert,” she declares, “Have you had pisco?”

I shake my head, and before long the empty wine glasses are replaced with goblets of some yellow concoction. I sip the sour mixture, the tendrils of alcohol’s Buzz curling into the edges of my consciousness, swirling all the time just beyond the limits of my vision. The Buzz unleashes from the noisy chaos of the restaurant crowd a glow I hadn’t before noticed, from Kathy an effervescence I had earlier somehow missed.

When we leave the restaurant, I again hold the door for Kathy, allowing myself for the first time to catch the tightness of her blouse over her chest, the sway of her hips in her skirt. I push the inappropriate thoughts from my mind, but The Buzz follows me back to the hotel, and I walk by her side, no longer trailing behind her like a meek puppy.

When she says, “Come to my room,” I nod, not questioning that of course she means for us to finally hold our postponed planning conversation, to set forth our schedule for tomorrow.

We take the elevator to the twenty-third floor, where the hotel doors are spaced far aside. I’m not jealous to learn she has a suite, her clout obviously earns her respect. “Make yourself comfortable,” she says, draping her jacket over the back of the desk chair, bending over to inspect the contents of the mini-fridge.

I sit on the bed, my eyes happily drifting over her ass. Her round cheeks press their shapeliness into the tight linen.

“I’ve got, uh, let’s see… vodka…”

“I like vodka,” The Buzz makes me say, suddenly beset with a flashback to my school days.

Ice cubes chirp as they ricochet in the glass, and she presses it into my hand as she sits down next to me. I welcome the old familiar burn. Yet, her hands are empty, her lips dry. “Nothing for you?”

“No.” Her eyes gleam as they study mine. She doesn’t expand on her answer, doesn’t explain why I’m drinking and she’s not.

And as the silence stretches on, and I sip my drink, and The Buzz warms my mind, I spot that at some point, she’s undone the top few buttons of her blouse, the beginnings of what promises to be some amazing cleavage sitting right there in front of me. I swallow heavily.

“How old do you think I am, John?”

I know she was in one of those ‘Forty under forty’ industry features recently — I’d submitted her user account to the magazine for consideration myself. But beyond that… “Uh, thirty-five?”

“I’m thirty-eight.”

“Oh. I’m twenty-four,” I announce.

“I know.” She squeezes my knee.

I look down at her hand, frowning, confused as to what it’s doing there.

She says, “I think we should get to know each other a little better.” She licks her lips hungrily.

And I’m still lost. “What?” But then, “Oh.”

Because even though I’m slow, Kathy’s hand is sliding down her chest, her fingers slipping between the overlapping folds of her blouse, popping buttons free one by one. My eyes widen, a little whimper escaping my lips, as more and more of her breasts come into my view. And I don’t find out how I’d earlier missed them, because they’re fucking huge. Her black bra strains to contain them, twin mountains of delicious flesh.

I’m panting, my jaw slack.

“Do you like them?”

I nod pathetically.

She smiles, reaching behind her back, popping the clasp. And as she shrugs free from her bra, she grabs my head and pushes my face down into her cleavage. My drink spills on the bed, the ice sliding over the blanket. I don’t care. I’m in tit heaven. I suck a hard, tan nipple into my mouth, my fist squeezing the other. I coat them in my slobber, licking and drooling and nuzzling. I shove my face between them, holding them against my cheeks with my hands.

I don’t even notice her squeezing my crotch, her unzipping my fly. Not until her fingers wrap around my shaft, thumb stroking my vein in a long, sensuous tug, do I fully find out what we’re doing.

“Aren’t you a healthy young man?” she giggles, pulling her hand back, just for it to return in a playful slap.

I gasp. My dick loves the censure, surging stiff.

“Get rid of these pants, John. They’re annoying me.”

I take off my pants, my shirt too.

Kathy takes me in, a thirsty grin pinching her dimples tight. “Has anyone ever told you,” she says, “That you’ve got a nice cock?” She grabs it, pulling me to the bed. “Don’t answer that. It’s rhetorical.”

She lays me back and gets on her knees at my side wearing the smile of a conqueror. Her fists discover my dick, wrapping around it so wonderfully, taking ownership of it. She strokes cock like an expert, firm and slow and steady and impossible to withstand. She watches me with interest, building me up and up. Her tits bounce.

“Let your hair down,” I pant.

She rolls her eyes, but grins and pulls the clips out. Silky, deep red locks spill down her shoulders.

Her fist is quick to rejoin it’s twin, pumping up and down the length of my roaring shaft. As much as she works me towards crescendo, she keeps my peak easily at bay, showing a mastery over my arousal that not even I possess. She’s precise, exact, the engineer even in sex. I’ve never had such pleasure, never had such a skilled partner, never been taken in by something so elemental as a handjob.

And she’s so stunning, so powerful. She’s a gorgeous, fiery goddess, busty and bewitching and seductive. She knows exactly what she’s doing to me, knows exactly how deep into her sway I’ve fallen. I can see it in the gleam of her eyes, in the brazen smile on her red lips.

I don’t know how long she keeps me this way. Could be twenty hours, or maybe twenty seconds. All I know is, my dick’s in heaven, riding a torrent of ecstasy that demands the surrender of all other wondered. Until she says, “I think it’s time you give me your cum.”

Her thumbs discover my glans, running tantalizing, merciless circles around the sensitive underside of my dick.

I whimper and wail.

My balls tense, heavy and full and willing for release.

Kathy arches an eyebrow.

And that’s all I can take. Orgasm explodes inside me. Cum explodes from my dick. I can feel it as it courses its way down my shaft, an intense and massive load, spraying up into the hotel suite in an obscene demonstration of potency. She squeezes my balls, urging more semen out.

I’m a moaning mess, drained and covered in my own spunk.

Kathy stretches out next to me, laying on her side. Her tits spill off her chest, rub against mine. “Good god, John. If you needed release that bad, you shoulda said something.”

I know she’s just teasing me. But The Buzz gives me an idea — makes me aware that an opportunity may soon be slipping through my fingers. “Take off your skirt,” I say.

“Why?”

“Because I said.”

She laughs, but she reaches down to unzip it, shimmying out of the tight fabric.

Her panties are black, wrapped taut around her round ass. I grab and squeeze it, but it’s not why I’m here. I roll her onto her back, laying down between her thighs, smearing the cum on my belly onto the quilt.

“You’re not going to–” she says, “Oh! I guess you are.”

I’ve pulled her panties to the side and am sliding my tongue over her pussy, dragging it past her clit. She loves it. Her chest heaving, she pets me. “Oh, fuck yes…”

Two days later we’re back at the office, back to reality. I’ve been avoiding Kathy, not trusting myself to keep cool if I see her. I don’t know… I don’t know what I’m feeling. Confused, definitely. Horny? Yeah, that too. Intimidated? Yes.

“John, come with me.” It’s Bob, my supervisor. He curls his finger, not even bothering to look at me. He leads me away from my desk, away from our open-office area, into the recesses of the building.

Bob knocks on a door.

The response is muffled, “Enter.”

It’s Kathy’s office, of course. Bob points at a chair, and I sit, eyeing only the floor.

“How’d he do?” Bob’s tone is gruff, “Worth his salt?”

I sneak a glance, see Kathy’s eyebrows raised, an amused smirk on her face. “Not too bad, for his first time.”

I blush.

“But I’ll keep working on him,” she continues, “See if we can’t get something out of his winning smile and ability to distribute company pens.”

I wince. Bob frowns. “That bad, huh?”

“Wasn’t his fault,” Kathy says, “Our competition was giving away free lunch, and I’d kept him up late into the night. Making him get more familiar with our material, I mean.”

“Right,” Bob says, not even batting an eye, “Those assholes keep undercutting our bids, doing all that crap work that we inevitably get called in to correct at the eleventh hour.”

“Right,” Kathy agrees, her eyes twinkling as she sends me a private smile.

Bob stands. “Well, thanks for putting up with him. These junior guys gotta cut their teeth somehow, right?”

“Yeah, yeah.”

I stand, too, but then turn to Bob. “Actually, hey, I’ll catch up with you. I have something I need to follow up with, with, um, Ms. Kaplan.”

Bob narrows his eyes, but shrugs. “Whatever. Let me know if he pesters you, Kathy.” He leaves, and I close the door behind him.

I’m standing in front of Kathy’s desk, and she’s looking up at me from behind it, an expectant, mocking grin on her face. “Yes?”

“I need to see you again.”

She bites her lip, considers. “There’ll be future conferences.”

“No, sooner than that. Like, way sooner. Like, now.”

Her dimples curl her cheeks, her red hair accenting them in waves. “I’m too old for you, John.”

“That’s not what you said in Cincinnati.” Or maybe it was Toledo.

“That was just some fun,” she waves it off.

I need her. “You don’t let yourself have fun at home?”

The protest forms on her lips, but she says nothing, pausing as if she’s actually listening to what I’m saying. As if she’s actually tempted by it. “What exactly are you proposing?”

What am I proposing?

Ten minutes later, I’ve got Kathy leaning back in her chair, moaning my name as she runs her hand through my hair. Her legs are spread wide, her pants on the floor. I’m under her desk, my face buried between her thighs, my tongue lapping away at her clit.

“Ok,” she pants, “This is fun, too.”

She presses my head down, grinding her hips against my mouth.

We didn’t end up dating, not exactly. But starting then, we fucked near constantly, getting up to some wild stuff. It lasted over the next year and a half until she took a job in another city, and although now it’s been five years since we’ve spoken last, just today I got a text message from her. She’s going back to that same conference where we’d first gotten together, wants to know if I’ll be there.

I’ve got some seniority now, and had planned on staying home, sending the new junior guy. But now I’ve told him to cancel his plans. He’s surprised, but I don’t care, I’m taking this show for myself. My dick is getting hard already…

NSFW: yes

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One Comment

  1. TerriblyEasy

    If you like this story, my post history is nothing but sex stories, and I’ve got a lot more collected on a free blog: terriblyeasy . wordpress . com