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The Sexy Supervisor

"A work related road trip ends with an amazing orgasm."

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3.6k words 3.6k words

Author's Notes

"This is pure fantasy, based on a very real desire for the boss."

I work a boring office job. Don't get me wrong, I don't mind it. It's not a bad gig. It pays well, it isn't very demanding and I enjoy the time with my immediate coworkers. The only problem I would have to confess to is the sexy distraction, I refer to as my supervisor.

I'd known him for a short while before he became my supervisor and I'd known of him for longer. He had a reputation throughout the firm as a hard worker and someone who'd worked his way up from an entry-level position. He's one of those good people we all wish worked everywhere because he cares about his employees and he likes to reward hard work with promotions and/or recognition of some sort. He's a consummate professional at work but he knows when to have fun, too. He's also cursed with humility, a great sense of humor and stunningly sexy good looks.

I've had a crush on him since the first day I laid eyes on him, to be honest. His piercing blue eyes, the smattering of freckles across the bridge of his nose, his strawberry blonde hair and a set of beautiful lips. The fact that I know his torso and upper arms are toned and tattooed add to his physical allure, as well. I try not to think about him in any way other than 'the boss' while we're at work however, that's not as easy as it should be. Not for me, at least. The problem isn't just that he's a coworker and supervisor. It's much worse. We're both married to other people.

Neither of us has ever had an affair but for the chance to be with him for just one night? I can't say I wouldn't do it.

Today, he's been informed he has to take a company car to one of our smaller branches, to check on some complaints another employee has launched regarding a broken office chair. He needs to replace the chair which isn't a big deal but, it involves a stop at the office supply store and an additional hour and a half of travel time to the branch. I want to go with him but I'm not sure he'll let me. I don't really have any reason to tag along but, I want to and it never hurts to ask. I knock on his office door and hear him respond affirmatively. I walk in and see him gathering his things and putting them in his messenger bag.

"Good morning," he smiles.

"Morning," I reply.

"What's up?" He asks as he leans over the back of his tucked chair to scroll through a few urgent emails. "Just checking for anything I need to wrap up before I head out." He looks up at me and continues, "I don't want to leave you with a pile of stuff to take care of while I'm gone." He smiles again. Those eyes. That mouth. His strong-looking hands.

"What are the odds you'll let me come with you?" I speak in the same casual tone I always use. Over the last few years, I've become adept at hiding any arousal I feel in his presence.

"I mean, I guess you could?" He shrugs, looking up at me again. "You just looking for some time out?" He smiles.

"Maybe," I reply. "It's Friday and nothing's going on here. Plus, I never get to just galivant across the state, so..."

He puts his hand up in a 'stop talking' gesture and chuckles.

"I get it. Go get your shit. We leave in five," he nods his head and starts typing a reply to an email that's caught his attention.

"Seriously? Sweet!" I smile as I turn to leave. "Thank you!"

"Thank me by meeting me at the car on time. I don't want to be on the road all day, I got some shit to take care of this afternoon."

"Yeah, yeah, yeah," I playfully mock, as I shut his door behind me. "Which car, by the way?"

"The SUV, silly," he smiles. "I don't think the chair we need to pick up will fit in that tiny hatchback."

"Right," I nod and make my exit. The firm has three company cars they maintain for travel purposes; an SUV, a Prius, and a tiny antiquated hatchback. The Prius was in the shop due to a 'parking mishap' as explained by the mailroom supervisor. We suspected there was more to the story but the firm owners didn't seem overly concerned about it.

I walk into my office, gather my belongings and check through my own urgent emails in need of responses before I leave to meet him at the car.

When I get to the car, he's already there and checking the oil.

"You a mechanic now?" I joke as I open the passenger door to throw my purse in the floorboard.

"Dude, you know how people treat these cars, right?" He spoke as he slid the oil stick back into its place. "I told you, I got shit to do this afternoon and I have no intention of being stuck in the middle of nowhere with a blown, smoking engine," he winked.

"Good point," I nod in agreement and ask him if he's checked the tires yet. He rolls his eyes and tells me to get in the car, as he closes the hood. I smile and obey. As I buckle the seatbelt and situate myself, I see him looking at me. "What?" I ask self-consciously.

"Nothing," he laughs and he starts the car.

As we walk through the store to pick out the new chair, I try to keep inappropriate thoughts at bay but to no avail. He's wearing jeans and he's walking ahead of me, leaving me with an eyeful of his very cute rear end.  We approach the office furniture and he asks if I remember what kind of chairs that branch has. He says he wants to keep it uniform.

"I've never been there so I wouldn't be able to answer that. This is the first time you've actually let me leave the office with you," I reply, shrugging.

"Oh, you poor thing," he rolls his eyes. He takes his cell from his back pocket and dials. "Claire? Hey, it's Chris. Do me a favor and text me a picture of the broken chair, would ya?"

I start looking at the products in the surrounding area. Pens with quotes on them, markers in fluorescent colors, notepads, all with an advertisement for printing company names free if a certain number are purchased.

"Laurel, you ready?" I hear him call. He's standing a few feet behind me, propping a large box in front of him.

"Is that the magic chair?" I ask as I go to grab an end.

"Apparently. What're you doing?"

"I was going to help you carry it."

"No need, it's not heavy," he smiles. He heaves the box onto his shoulder and nods for me to follow him. I may have drooled a bit but I can't be sure. I've never been alone with him in this kind of environment and my desire for him is growing.

On the way to the branch, all goes as one would expect during an hour and a half long drive. We agree on a radio station, discuss the music and artists, I play games on my phone, he talks about the demands of being a supervisor at our firm. As we reach the rural branch, he pulls into the small parking lot, turns the radio down and looks over at me.

"Here's the plan: I'll put the chair together and you keep Claire busy," he states as we exit the vehicle. He opens the rear door to retrieve the boxed chair, "She's a talker and easily distracted. Plus I think she has a crush on me so if you don't keep her busy, she'll follow me around and jibber-jabber the whole time." I chuckle and close the rear access door as I watch him walk toward the building's entrance.

That spectacular little ass in those jeans has me completely distracted. I realize he's almost to the entrance so I speed up to get ahead of him so I can open the door for him. He thanks me and maneuvers through, carefully avoiding hitting the glass doors with the box.

I look at my phone to check the time and see that it's 11 am.

"Chris!" Claire's nasally voice penetrates my ears. And my brain.

"Morning, Claire," he smiles politely. "Where am I going with this?" He indicates the box.

"Marla's office. Room 4," she smiles, wide-eyed. Claire's a nice woman. About my age but a few inches shorter, about fifty pounds heavier and a little goofier. But a nice lady, nonetheless. And yes, she does have a crush on him. I can see it in her face as she buzzes him through the inner doors. "Hey, Laurel! How's it going? I haven't seen you in forever!" Her attention is on me now.

"Well, you know how it is," I smile. "Boss is a hardass who never lets me out."

"I heard that!" He looks back at us and shakes his finger at me.

I talk to Claire, as instructed, listening to her ramble on about the divorce she's going through, about her son's horrible new girlfriend and her daughter's extraordinary academic abilities. I don't really mind. I always got along with Claire and honestly, I'm not really paying attention to what she's saying anyway. My mind is on Chris. I know he'll want to get lunch when we leave which I hope is soon. I'm not sure how long I can keep this desire for him under control. Tagging along may have been a mistake.

"Alright," he says as he walks back through the doors. "You ready, Laurel?"

"Oh, are you done already?" Claire asks with a hint of disappointment.

"Yeah," he replies, "turns out the old chair was entirely fixable. So, Marla's happy and I left the new chair in the storeroom just in case." He reaches for his cell and texts something to someone while fishing his keys from his front jeans pocket.

"Oh, ok," Claire smiles. "Thank you for all that and sorry you drove all the way out here for nothing."

"No problem. Besides," he started, "you heard her," pointing keys toward me, "I have to let her out of her cage once in a while or she gets restless." Claire chuckles. "And in a super cranky way," he adds for presumably, good measure.

"Haha," I mock, as I say my goodbyes to Claire and follow this beautiful man out of the building.

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"You hungry?" He asks as he starts the car. "Because I'm starving."

"Sure," I shrug. "I could eat."

As we pull into the fast-food parking lot, he shifts into park and pulls his phone from his back pocket. "Goddammit!"

"Everything ok?" I ask gently. I think it's his wife and by the tone in his voice, they're in the middle of one of their fights.

"No, but it will be. She's just being a pain in my ass," he states as he tosses his phone in the back seat. "You ok with this place or did you want something else?"

Oh my god, something else! "This is fine. I'm really just thirsty, to be honest." I can't eat around him. I'm too aroused which has, in turn, made me nervous. I really want to nibble on his ears. Kiss his lips. Taste his neck. Lick his nipples. Suck on his...

"Laurel," he says a little louder than his usual tone. I see he's half out of the vehicle.

"What?" I instantly know he's aware I'd let my mind wander.

"You ok?" He raises a brow. "Felt like I lost you there for a second."

"Sorry! I was thinking about something else," I reply as I step out of the car and reach for my purse.

We walk in and head straight for the bathrooms. A few minutes later, we meet at the counter. I order a large soda, he orders a salad and a water. He pays for all of it and we find a table.

"You sure you don't want food? We still have a couple of hours before we make it back."

"I'm fine," I smile and thank him for paying. He eats his salad while I stare out the plate glass windows, looking at passing cars and trying to keep my face neutral.

Back in the SUV, we place our drinks in the cup holders and he retrieves his phone from the back seat. The way he stretched back, the proximity of his body to mine, the way he smells. I touch him. I put my hand directly on his back just so I could imagine what it would be like to hold him. Or pull him inside of me.

"What's that about?" He smiles as he readjusts himself in the driver's seat.

"You were in my bubble," I answer, scrolling through my personal emails.

"Oh. Wouldn't want that," he mocks.

"Or maybe I would," I smile and turn away attempting to be less obvious by being overtly obvious. He laughs and starts the car. Hmmm. I feel encouraged. Or maybe it's the desire/hunger/boredom combination?

As he pulls onto the interstate ramp, I feel him look at me. "What?" I say, wondering if I should have ignored my overtly obvious plan.

"Nothing," he turns to check for oncoming traffic. There isn't a lot at this point. It's just after lunch and we're in a less populated part of the state. I could probably try something? He wouldn't fire me if he wasn't interested, he would just ask me to stop and I would stop. It might make things weird between us, though so, I ponder the fantasy in my head and continue playing on my phone.

"Thanks for coming with me," he smiles.

"Thanks for letting me," I reply. "I didn't think you would when I asked but it was nice to get out of the office for a while."

He nods and pulls his phone out of his pocket.

"Hey, no texting and driving," I state and take his phone from him.

"What are you doing?" He asks, with his hand out. "Give it."

"No."

"Laurel, give me the phone," he isn't angry. His tone is playful. His face is passive.

"I'll give you something but it isn't going to be this phone," I reply as I toss his phone in my purse.

"Oh, well now, this just got interesting," he looks at me in a way I don't recognize. Is he flirting with me? Is he aroused? Is this all in my head? "What are you planning on giving me?"

Oh my god, oh my god!

"Good question," I turn in the seat to face him. I see his cheeks going flush. I reach over and put my hand on his thigh, slowly working my way toward what I imagine to be a silky smooth dick. I feel his body stiffen against my hand but he isn't stopping me. He, instead, moves his thigh toward me. I undo the seatbelt completely and lean toward him. He glances over at me. I kiss his ear. He lets me.

I nibble on his lobe and he lets out a soft moan. I'm extremely turned on and I don't know that I could stop myself if I wanted to at this point  I begin kissing his neck while gently rubbing his upper thigh. I can feel his dick getting hard. I'm turning him on! My fantasy is coming true!

I continue kissing his neck while I caress his other ear with my free hand. His moans are getting a little louder. A little more guttural. Way more arousing.

"You ok with this?" I whisper in his ear while continuing to massage his thigh.

"Only if you are," he answers with need in his voice. That was all I needed to hear.

I begin gently rubbing his dick and I can feel its hardness. I go to undo his belt but his hand is already doing it. I instead undo his zipper and stick my hand directly in his pants while still kissing his neck.

"Oh god," he whispers.

"Keep your eyes on the road, Chris,' I whisper to him. "Don't kill us, we got shit to do, remember?"

He nods. I have his dick in my hand. It's as smooth as I imagined and bigger than I expected. I'm as wet as he is hard and I really want him inside of me. I stroke it slowly but intently as he moans and moves his hips to the rhythm I'm setting. I lick his ear lobe and whisper, "Isn't there a place we could pull over?"

"I'll find one," he states, not hesitating to look for road signs indicating a turn-off. I bend down and take his dick deep inside my mouth. He squirms while letting out a grunt. I move up and down the shaft, as deep as my throat will allow while using my hand to massage the shaft in a corkscrew motion. His grunts are louder. He has a hand full of my hair in his fist and his hips are fully in tune with the rhythm I'm keeping as I suck him in and push him out. I feel the vehicle slow down and I quickly pop my head up to see where we are.

He's pulled off into a rest area and attempting to park the SUV in a more secluded location, away from the shelter house. He turns my head toward him so we're face to face and kisses me. His lips on mine, his tongue in my mouth, his groans still affecting me in a visceral way. I continue moving my hand up and down the shaft of his dick while he fondles my breast. I grab him, pulling his mouth to mine. He kisses me hard. I love it. I want to taste every inch of him.

He finds the seat lever and uses it to maneuver his seat back. He then pulls me onto his lap where he continues kissing me before he pulls my hair back, exposing my neck. He kisses my neck and follows the line to the breast he's released. His tongue is on my nipple, he's still pulling my hair and I feel like I might come before he even gets to fuck me.

"Oh god," I exclaim while I grind myself against his groin. His moans are getting louder, faster, less controlled. I free myself from his grasp and take his dick into my mouth again. He grabs the headrest of his seat with his hands and lets me have my way with him.

I remove my pants and straddle him while I unbutton his shirt.

"Today would've been a good day for a skirt," I joke while I fight with my pant leg. He agrees while he unbuttons my blouse and unhooks my bra to release both breasts. I pull my panties to the side and slide his hard dick inside myself. He gives a good thrust to assist and the pleasure is exhilarating. I almost can't hold back. I want to come so badly, I start grinding him to get his dick as far inside me as it will go. He sucks my nipples while squeezing my breasts with his hands. I'm holding the seat to steady myself because I can feel the orgasm building. He quickens his thrusts and encourages me.

"Yeah, baby... just like that... come for me... come on my dick..." And I do. I come hard. I come so hard, my body shakes and I lose myself for a few seconds. He kisses my mouth in the middle of my orgasm which keeps it going. "You got another one in there?" He smiles salaciously. I return his smile knowing he wants to come, too. I climb off his lap and take his dick back into my mouth, sucking hard and fast, corkscrewing the shaft with my hand. I hear him talking again. "Yeah, like that... oh god, don't stop... just like that... fuck, I'm gonna come!" And he does. Loudly. Explosively. I can't take all of it and I feel some of his come dripping from the sides of my mouth. I swallow what's in my mouth and I gently keep sucking. I feel him squirming and I hear him gasping.

He pulls my head up to eye level. His hooded eyes staring into mine. I smile knowingly and return to the passenger seat. I pull my pants up, fasten my bra and button my blouse. I readjust myself in the seat while he does the same. I take a few drinks from my fast food soda and catch my breath. That was the longest most intense orgasm I've ever had. I don't know if it will ever happen again but I'm glad it happened now.

"I didn't even know I could come that hard!" He says when we return to the interstate.

"Me neither!" I agree. "I'm still shaking. You should be proud of yourself," I smile. "And you still have time to get whatever shit you needed to do, done."

"Oh yeah. Nah, fuck that shit." He smiles and takes a few drinks from his water.

We continue the drive as if nothing has happened. But it has. And now I wonder if it will again?

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