“Make Me Feel Something.” The Regional VP Sees a Little of Herself in Me– and A Lot of Me in Her! [M25/F45][Cougar][Can I Take You Home?][Cunnilingus][Creampie][Blowjob][Anal][Shower Sex][Boss][Multiple Orgasms][Lots of Cum][Work Fantasy]

(Based on image 13!)

The lights are going down on the corporate Christmas party and the last stragglers are starting to filter out. The lucky ones are wrapped in each other’s arms, bouncing off the walls as they make fools of themselves in their haste to get to a vehicle. Some of them might even make it home before they give in to the siren call of each other’s bodies.

Then there are the unlucky ones, like me, who are leaving with nothing more than a vague buzz that will almost certainly be a hangover in the morning.

At least I don’t have work tomorrow.

I’m nearly to the door when I feel a hand on my shoulder. I turn, already forming an apology for whatever it was I left behind, only to find Haley Wesser, VP for my entire region, staring at me.

“Adam.” Her voice is sharp, honed by years of board meetings and office politics. “I hope you had a good evening.”

How does she know my name? I’ve spoken to Haley maybe three times in my five years with the company, and never for more than thirty seconds at a time. Everyone knows her of course, the legendary VP who, rumor has it, defied the CEO on more than one occasion to do things her way, only to have record profits in her region to back it up. Her name is whispered at our company like a talisman and I’m more than a little starstruck to be standing in front of her after watching her from a distance all this time.

“Walk me to my car?” It takes a second or two to realize she just asked me a question.

“Oh- of course!”

A hint of a smile. “Thanks. Are you ready?”

I nod, opening the door for her and she strides past, her bob-cut blonde hair hardly moving in the stiff breeze outside. Beneath her long jacket I can see fragments of the cocktail dress I know she has on, a deep blue number with a plunging back and a neckline almost scandalously low for this kind of event. The jacket doesn’t cover her heels though, which click on the pavement as she starts to walk, her long legs like something out of an old pinup magazine. I’d watched her off and on all night, always from a distance and always knowing she was way out of my league. Still, it was fun to watch.

She peppers me with questions as we cross the long parking lot to her car:

“How long have you worked for us?”

“Going on five years now.”

“Wife? Girlfriend?”

“Neither. Just a dog.”

“Family nearby?”

“A few hours from here.”

“Hobbies?”

“I fish. Do some skiing in the winter. Camping in the summer, that sort of thing.”

“Outdoorsman. I like that.” She flashes me another hint of a smile. It feels a bit like an interview, like she’s creating a mental index card with various things about me all labeled in neat handwriting in dark ink for reference later.

“I suppose you know most of my answers. I’ve worked for this company for nearly twenty years now, met my husband here and divorced him ten years later. Haven’t had much time for hobbies or family, especially since then.”

I nod, making a noncommittal sound in response. I knew– Hell, everyone knew about the divorce, especially since her ex-husband was the CEO. Rumor had it that they had flipped a coin for ownership of the company when it came down to it. She’d lost, but her ex knew her well enough to know to leave her alone in her fiefdom, and Haley had been putting up record profits every year since.

Still, it was hard to imagine that those meetings were anything but terribly awkward for everyone involved.

By now we’re nearly to her car, a black BMW that gleams in the faint moonlight.

“Adam?”

“Yes, Miss Wesser?”

“Call me Haley. I saw you watching me tonight, you know.”

“I-uh-Haley, I certainly didn’t mean to make you uncomfortable…”

This time the smile is more than just a hint as she turns to face me, her back to the car.

“Who said anything about being uncomfortable?”

I blink, not sure how to respond to that.

“Would you believe me, Adam, if I’d said I’d been watching you too?”

“You– have?”

“Mmm. Not just tonight, but for several months now. Watching your performance, watching you work your way up– starting as a new recruit and now nearly to manager yourself.”

I’m a little taken aback by how well she knows my portfolio, but it’s all true.

“You remind me a little of myself,” she continues. “Young, ambitious, a drive in you that the corporate world hasn’t extinguished yet.”

“Thank you, Miss… I mean, Haley.”

She places a hand on my chest now, just lightly, but my skin tingles as though she’d scratched my bare skin.

“I miss that person. The person I was back then. I have a favor to ask of you, Adam. I want to make it clear you can say no, you can walk away and there will be no repercussions, no retaliation– understand?”

I nod, my mouth drying up. “What do you need?”

“Need… that’s a good word for it.” She leans in closer, and though there’s nobody around, her voice drops to barely more than a whisper. My skin prickles as her breath caresses my neck.

“I need to be reminded what it’s like to be taken, Adam. I need to feel something again.”

A heat starts building in me, fueled by the look of raw desire in her eyes.

“I need something– maybe for tonight, maybe for longer– but I can promise you that you’ll never forget it.”

She pops the door to her car open, one leg angling into the driver’s seat.

“If you think you can help me with that, you have until the count of five to get in the car.”

I slam the door with three seconds to spare.

She floors it, tires squealing as we peel out up the hill to the part of town where the rich and famous congregate. This late at night the lights are all green and we make it in record time, but not before her hand has moved to my thigh, smoothing my work slacks over skin that suddenly feels unnaturally warm.

By the time we make it to her house I am hunching over to try to hide the tent in my pants from any nosy neighbors. Haley doesn’t seem to care one bit though, shedding her coat before we even make it into the front door and pulling me in for a long kiss on the doorstep, a kiss that makes sparks fly behind my eyelids.

Her house is beautiful but I barely see any of it. She guides me to the bedroom with urgent steps, shedding clothes along the way. Her heels lie forgotten in the entranceway, along with my belt. My tie is tossed over the back of a plush leather couch as we pass through a living room. My shirt winds up balled on the floor of her hallway and her dark blue dress drapes across the standing mirror in the corner of her bedroom.

“So,” Haley purrs, “You’ve got me right where you want me, I hope. Now, what are you going to do with me?”

For all her briskness before, there is a note of hesitation in her voice now, her eyes searching mine for hints of what is to come.

“First, I’m going to start by exploring your body– every inch of it.”

She hums approval as I pick her up and set her on the bed, my mouth already working down her neck to the paler skin beneath, finding the curve of her breasts and tracing it down, inhaling her perfume– citrus and soap and something else, something that would be frowned upon in the oak-paneled rooms where she makes decisions that move millions of dollars and thousands of employees.

The scent of her desire grows stronger as I move lower, my lips exploring her stomach now– toned from years of exercise at five in the morning before dressing for work, a body she has built through dedication and drive.

A body that shivers underneath me as I feel the close-trimmed hairs of her sex on my chin, my lips on her thighs now. They spread, welcoming me between them like an honored guest and I do my best to live up to the reception. Her scent is intoxicating up close– so is the rest of her. Her skin is warm against my cheeks as I taste her for the first time, her thighs around my head as my tongue finds the pinkness of her slit, carefully tracing it from top to bottom.

She sighs as I enter her for the first time one hand clutching my hair, the other rubbing herself as I explore this part of her too, a part of her that no one ever sees, a part of her she keeps hidden away for the vast majority of her life.

“Right there,” she murmurs, holding me in place with my tongue deep inside. “That’s where it aches…”

I do my best to soothe that ache, first with my tongue and then with my fingers too, angling them inside her to run along her inner walls, listening for the hitches in her breathing that tell me where she is most sensitive, where the ache is most insistent.

“There!” She gasps as I touch one spot in particular– a rough patch along her inner walls that makes her melt into the bed, arms and legs going limp as I massage it, my tongue taking over in teasing her clit as she groans above me.

Her first orgasm happens moments later, a long, languid climax that stretches on for several minutes, throaty gasps and deep breaths all coming one after the other to tell the story of a release too long in coming.

“That’s much better,” she finally sighs, her voice more relaxed than I’ve heard it all night. “I hope you’re not done though?”

I start to shake my head no but she’s already on the move, pulling me up to kiss her, a hard kiss that becomes even more intense when she rolls us over so that she is now on top. She never breaks the kiss as she lowers herself onto me, a low moan building deep in my throat as her pussy stretches around my cock.

I may be twenty years her junior, but that only means she has had decades longer to perfect her technique, and she rides me with the vigor of a woman half her age, her hips rocking so sensually that I feel myself clenching already, willing myself not to ruin the moment quite yet.

But she has other plans.

“We have all night,” she whispers in my ear, finally breaking the kiss. “And I want to feel your cum filling me right now. I want to feel it inside me when I suck you later. I want to feel it inside me when you fuck me again. So don’t hold back, Adam. Fill me now, and save your stamina for when it matters.”

I break. She growls her approval, nails raking down my chest as she rides me like a victorious champion, back arched, breasts proudly on display, head flung back to the sky as I empty myself into her womb.

“Yes!” She cries out to the vaulted ceiling, the word echoing in the cavernous bedroom. “That’s it! Give me everything you have!”

My mind and body both obey and she smiles as she drains me, finally lowering herself to me again and kissing my neck, my lips, my ears.

“That was just what I needed,” she murmurs. “But I hope you have more in you…”

The way she moves is like nothing I’ve ever felt. Within moments my cock is twitching again, and when she slides down my body to take me in her mouth her tongue feels absolutely magical.

“Good, I was hoping you weren’t done yet,” she says, her words muffled by my rapidly-growing shaft.

“Not with you doing that.”

She hums her approval, quickly bringing me back to full hardness, but once again she does the unexpected. Instead of riding me again, or even changing our positions once more, she reaches into a nightstand, pulling out a bottle of lube.

“The ache has shifted,” she explains, her voice husky. “I hope you can make the adjustment.”

Wordlessly I pull her toward me as she runs her hands over my cock, coating it in the slick lube. She doesn’t resist when I turn her away from me, bending her over her own bed and lining up my head with the entrance to her ass.

“Show me where it aches.”

She spreads her cheeks for me, her tight hole winking in anticipation. My cock slides inside her slowly but inexorably as she breathes in deep, pushing back against me until her ass meets my thighs.

“Are you going to stand there all night, or are you going to fuck me?” She challenges, and whatever reservations I have about taking it slow disappear in an instant.

“That’s it! Make me feel it!”

My cock plunges into her, shaking her entire body as it does, but she is a wild creature now, the long-repressed emotions rising up like a thunderstorm inside her. She meets my every thrust and more, and when I pull her arms behind her, using them as leverage to go even harder she screams her approval into the mattress, a long, wordless cry of primal release.

It takes longer for me to cum this time and in that time I lose track of how many times I feel her ass clench around me, how many times she cries out my name into the bedsheets. When I finally do feel the familiar ache in my balls I lean down, still thrusting heavily, and growl into her ear.

“Haley, I’m going to cum in your ass now. Is that what you want?”

“Yes! Fucking do it!”

“Say it again.”

“Cum in my ass! Let me feel it inside me!”

I push as far as I can into her, grunting as I feel yet more of my seed shoot into her. Haley moans too as she feels my cock pulsing deep inside, and when I finally pull out a dribble of cum follows, trailing down her thigh.

“It feels… so good…”

“You’re amazing.”

She turns her head to face me, a languid smile playing out across her lips. “Help me to the shower.”

I carry her to her bathroom where the large walk-in shower is big enough for both of us. By the time we have finished washing each other my cock is hard for a third time and I take her right there in the shower as the water sprays across my back, holding her upright with her legs wrapped around my waist.

“I haven’t done this since I was your age,” she confesses as I use my hands to move her up and down on my cock. “I missed feeling passion like this. I missed so much…”

I kiss her before she can say more, bringing her back into the moment just as I release one more load into her. This time my orgasm sets off hers and I hold her tight as her pussy flutters around my cock, not letting go until I am sure that she can stand on her own again.

Both of us collapse into bed and are asleep in minutes, but when her alarm goes off at four-thirty the following morning she is up immediately.

I watch her in the mirror as she gets ready– of course she’s working on a Saturday. Her body in the morning light looks heavenly.

“You’re sure you don’t want to stay?” I say, my voice raspy with sleep.

“I can’t,” she responds, and I note the way her voice has shifted back into work mode, focused and crisp. It’s an odd feeling to hear that voice when I can still see the aftermath of last night leaking out of her.

“I’m off to work now,” she continues, putting in a pair of earrings as she speaks. I watch her breasts rise and fall with the motion of her arms. “Make sure you’re gone by the time the cleaning lady arrives.”

“All right.”

She finishes dressing, settling on a blouse and a pair of dark pants to go over the bra and underwear she fished from a drawer. Before she leaves, she sits on the side of the bed next to me, cupping my chin in her hand.

“I’m going to be feeling you inside me for a day or two at least,” she says, a hint of the desperate passion I’d seen last night returning to her voice. “If you can keep this a secret between us, maybe there can be a repeat performance after the quarterly earnings report.”

“My lips are sealed,” I murmur, wondering how many days there are until that report and whether I can last that long without seeing her again.

“Good.” She pecks me on the cheek and strides to the door, all business once more. “Until next time.”

I watch her go before rolling over and trying to catch a few more hours of sleep. I dream of her underneath me, her wild eyes boring into my soul, begging me for more, more, more!

It’s seventy-eight days until the quarterly reports, I find out later that morning.

Time to start counting down.

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