On The Naughty List

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This one is for the Literotica 2021 Winter Holidays Story Contest. As always, your votes and comments would be much appreciated. Thanks for reading, and I hope you enjoy it.

And thanks to No1Ukno for his invaluable editing skills.


Ooh, I can hardly wait. Just another few days, and we’ll all be off for ten whole days for the holidays.

I’ll be enjoying Christmas with my family in snow country in Hillsdale. And from what I’ve heard, my boss Noah, aka as “Hot Stuff” around the office, will probably be off to some warm, sunny destination in the Caribbean, or some posh ski resort up north, probably with a gorgeous woman or two to entertain him.

I know it’s really none of my business what he does, except for one tiny little thing — I’ve been head over heels in love with him from the day I started working for him just over two years ago.

The man is absolute masculine perfection. Tall, sandy-haired and ridiculously handsome, with just a touch of gray at the temples. He might be forty-seven, but he sure doesn’t look it. So delectably toned and fit, he can really fill out a suit. Whenever he looks at me with those big, slate blue eyes, I can actually feel my panties starting to melt.

Sadly though, most of the time he’s all business. Considering he owns the company I can’t really blame him. Especially since he built his privacy protection firm up from nothing on his own. Though he’s done really well for himself, he’s not the type to sit back and rest on his laurels.

Aside from being wickedly smart, he’s also got a heart of gold. Which in my books, is a pretty lethal combo. Though hardly anyone knows how kind he is, because he’s not the type to brag. But I’ve seen so many organizations writing to thank him, for not just his generous donations, but also the time he puts in to help out.

Maybe just as well he’s been kind enough to give us this time off over the holidays. Then I can go and recuperate at my parents’ place. Where I can finally think about something other than peeling him out of his suit, and having my naughty way with him. It makes me so crazy sometimes working together side by side, and not being able to even touch him.

Silly thing is, I know it’s just a fantasy. Noah would never be interested in me. Outside of the office, he’d never look at me twice. So, obviously it’s never going to happen.

I’ve seen the type of woman he’s into; typical snooty, blonde-haired blue-eyed, rake thin models. Whereas, I’m a little on the curvy side with a full 36-24-36 hour-glass figure. And fiery red hair, with a dusting of freckles across my nose and breasts, along with what I consider, overly big brown eyes.

I also know it’s not exactly fashionable to have a little junk in the trunk, although my last boyfriend never complained. I imagine it would give a guy something to hang onto whenever we made love.

When I walk into boss man’s office in the morning with his coffee, I always smile and give him a cheerful, “Good morning, Noah.” With the holiday so close, today I decided to add a plate of Christmas cookies I baked, hoping he’d like them.

Without even bothering to look away from his computer, just like always, he mumbles, “Morning, Kendra. Thanks for the coffee,” without skipping a beat, or even taking note of the cookies I took hours to decorate.

I’m pretty sure I could send his morning coffee into his office with a drone, and he’d probably say the same thing.

I’ve come to accept the fact that as far he’s concerned, I’m invisible, and he barely knows I’m alive.

I know one day I won’t be able to take it anymore. But before I give up and hand in my resignation, I think it might be fun to strip off and wander in with his morning cup of joe, wearing nothing but my sexiest bra and panties, and a smile, just to see if he’d sit up and take notice.

If I’m going to be on my way out the door, once I’ve had enough and finally decide to quit, I figure I’ll have nothing to lose. Except for maybe the last of my dignity. If I do get up the nerve to wander in there wearing nothing but a few scraps of lace, and “His Hotness” doesn’t even bother to lift his gaze from his monitor, it’ll crush me.

Today, I was just about to turn and leave his office and he shocked me when he turned his head and actually asked, “So, what are your plans for the holidays, Kendra?”

Now that he’d spoken to me, I nearly swallow my tongue, trying to get the words out. “I’m uh, going to rent a car and drive up to see my family in Hillsdale.”

He nods, and I feel his gaze slowly slide over me. Deciding to be a little festive, I’m wearing a red body-hugging sweater, that really shows off my girls. Along with a black pencil skirt that hugs my tush like a second skin, and black heels, that give me a little height, considering I’m only five foot two.

Just from the look in his eyes, I can feel my nipples growing embarrassingly hard. I know he’s gotta notice, too. Damn things are poking out hard enough to make him wonder if I’m trying to smuggle Escort Yeşilköy pencil erasers out of the office in my bra.

Then my jaw almost hits the floor when he casually says, “I’m driving north for the holidays, too. So, I could give you a ride if you want. Save you having to rent a car.”

I look around, wondering if I’d heard him right, or could be, I was still in bed, dreaming. We’d ridden in taxis before and usually chatted on the way to meetings, and realized we shared the same sense of humor, whenever we took a minute to joke, but never gone anywhere that wasn’t work related. So, this would be a first.

Suddenly, it dawned on me that he was waiting for me to answer. So, I cleared my throat and took a breath. “Well, if it wouldn’t be out of your way.”

He shrugged. “No, I’m driving up north for some skiing with a few friends. So, I could drop you off and circle back to the resort.”

“Sure. That would be great. Thanks, Noah.”

Then he looked down and smiled when he noticed the cookies. “Did you make these?”

I nodded. “I did. I always like to bake around the holidays. Makes it feel more like Christmas.”

When he just nodded with an odd look in his eyes as he reached for a shortbread, I smiled and went back to my desk outside his office. Sitting down in my chair, staring at my computer, I could hardly believe that he’d offered to give me a ride. We’d be at least two hours or more alone together in his car, so he’d have to talk to me then. At least I hoped.

Otherwise, it was going to be one long, disappointing drive.

Day before Christmas, Noah showed up at my apartment with his big, black SUV, with his skis secured on top. I’d never seen him in jeans and a sweater before, and I gotta say he looked every bit as hot as he did in a suit.

I winced though, when he cocked an eyebrow at my two suitcases and all the other bags with gifts and cans of cookies that I was bringing for my family. “It’s not too much, is it?”

He shrugged and actually chuckled. “No. The trunk’s pretty big, so I think it’ll fit.”

Once we were settled in and were driving north for a while on the highway, I was so zoned out, and feeling so comfy, I nearly jumped out of my skin when he broke into my thoughts and asked, “Are you warm enough?”

“Yeah, I’m good.” So good, now that I was getting to spend a little alone time with my hunky boss. I kept stealing glances at his handsome profile from the corner of my eye, and could still hardly believe that we were together like this.

He had the radio playing and my all-time holiday favorite came on, Mariah Carey’s All I Want for Christmas is You, which had me wanting to sing along. But then he disappointed me when he changed the station.

“You don’t like Christmas music?” I asked, looking across at him, surprised.

It took him a long while to answer. Finally, he heaved a breath and shared something I never knew. “It reminds me of when I was a kid, and stuff I’d rather forget.”

“Oh.” He didn’t elaborate, but it was obvious that Christmas wasn’t exactly his favorite holiday. My heart sank, so sorry for the boy he used to be, wondering what he’d gone through.

We drove for a while in silence. Then his mood obviously had lifted, the way he looked across at me with a little smile playing at his lips, and asked, “Apples or oranges?”


“Thought we should get to know each other, since we work together every day and never really talk much, at least nothing personal. So, which do you prefer?”

“Oh then, definitely apples. There are so many different kinds, and they can be super sweet or nice and tart. Oranges,” I shrugged, “are just oranges.” Then I smirked. “Although, given the choice, I’d much rather have a sweet, juicy mango dripping from my chin.”

Playfully waggling his eyebrows, he smiled across the car at me, chuckling. I felt a little flutter go through me, just seeing his face light up. He was normally so serious; I was really enjoying seeing his playful side.

“Okay, then,” he asked, “Chocolate or vanilla?”

Smirking, I eyed him and told him, “Actually, some warm, sweet caramel would do it for me.” Especially if he was painting me with it, and then slowly licking it off.

He looked a little surprised, I think realizing I was flirting, though I was just glad that he couldn’t read my mind.

“Okay. Your turn,” he said, and waited.

I don’t why I said it, knowing I should have asked him something he’d expect like, Dog or cat? I guess thinking it would be fun, I asked, “Top or bottom?”

That sure as hell surprised him. He choked out a laugh, and then laughed so hard he started coughing. Once he caught his breath, he narrowed his eyes on me. “I hope you’re talking about bunk beds.”

I gave him a little wiggle of my eyebrows and lied, “Of course.”

Then his eyes went dark as sin as he leaned closer and murmured, “Since you asked, I prefer to be on top. But I’d be just as happy to be on the bottom.”

I swallowed hard, Yeşilyurt escort my cheeks burning, as I pictured him with his weight on his hands, looming over me, naked and hard.

Seeing that he’d gotten me back for teasing him, he chuckled and turned up the radio. While I sat and blushed.

Finally, he broke the silence. “So, do you come from a big family, Kendra?”

Like I always did, I smiled as I thought of them. We were all so close. “Yeah, there’s five of us. Three girls and two boys, and I’m the baby of the family.”

When he just nodded, I asked, “How about you?”

“There’s just me.”

“Oh.” When he went silent, I didn’t know what else to say. But I thought I’d ask, “Do you ever go home for Christmas?”

I felt so bad for him when he said, “No. There’s no one to go home to. So, I usually just spend the holidays with friends.”

I never realized he led such a solitary life. And I really wished he had someone to call his own.

A few hours north of the city, as we drove deeper into the snow belt, it was starting to come down so hard, he had to put on the wipers. The way the wind was picking up, and blowing the snow around, was making it nearly impossible to see where we were going.

I could see Noah hands gripping the steering wheel pretty tight, while I was biting into my lip, praying we’d get there in one piece.

The snow plows hadn’t come out yet, and the road was getting slippery. Just in time, thankfully Noah managed to put the brakes on without sliding. When up ahead, we saw through the driving snow, two cars had slid into the ditch. Thankfully, there was a police car stopped to help them with its emergency lights flashing.

Twisting my hands in my lap, starting to feel anxious, I whispered, “This is getting bad.” He nodded when we saw that straight ahead, two more police cars were stopped in the middle of the road blocking traffic with their full light system on.

One policeman standing in front of the squad cars had a flashlight, and was waving everyone off the road onto an exit ramp. It looked like they’d closed the highway because of the whiteout conditions that were starting to make it really hazardous to drive.

Not long after we got off the highway, Noah pointed ahead when he noticed a motel with its ‘Vacancy’ sign lit up, that thankfully had a restaurant attached. “I think we’ll stop and grab some lunch and see if this blows over.”

I nodded. “Yeah, probably a good idea to get off the road until the snow plows come around.”

When we stepped inside the old motel decorated with a single strand of multi-colored Christmas lights strung along the length of it, we noticed people were lining up to get a room. Noah nodded his head at the lineup. And I think we both realized if it kept snowing the way it was, if we didn’t get a room soon, we’d end up spending a chilly night in the car.


I knew I should never have offered to give her a ride. Now we were going to be stuck together, probably overnight. But I’d hated the thought of her driving up on her own, especially this time of year when the roads could be treacherous. So, of course I opened my big mouth, and look where it got me. Stranded at a motel with my sexy assistant.

It was hard enough working with her every day, thinking how much I’d love to peel her out of her clothes to finally get a peek at her gorgeous body.

Around the office, I can’t even look at her if I want to get anything done. Super smart, funny and so cute. And good god what a body. Curvy in all the right places. I get hard sometimes just thinking about her.

Now I’m hoping we can get separate rooms, or things are going to get awkward.

Just my luck, the old guy at the reception desk smiles and tells me how lucky I am, because they’ve only got one room left. Resisting the urge to roll my eyes, I look over at Kendra and she just shrugs, so I tell him, “We’ll take it.” Though I’m kicking myself, knowing how crazy this is going to be, having to spend the night with her, while trying to keep my hands to myself.

Biggest problem with her, aside from the fact she’s that basically half my age at only twenty-five, is I can tell that she’s a nester. I know she’s the type who’d love to settle down with Mr. Right and have a bunch of babies. But I never plan to marry, nor would I ever dream of having kids. Considering I never had any role models growing up, I wouldn’t know the first thing about being a father.

I don’t think it would be fair to her to even consider starting anything. Plus, the fact that she works for me, so I shouldn’t even be going there.

Once I unlocked the door to our room and we took a step inside, Kendra always willing to look on the bright side, looked around at the dated décor, smiled and said, “This looks okay. At least it’s clean.”

Only one bed, though. Shit.

I watch her unzip her coat and toss it aside, and my eyes of their own volition make a slow journey over her luscious body. In a body-hugging black sweater Zeytinburnu escort bayan and skin tight black jeans, and over the knee leather boots, with her long red hair curling down her back, she looks like sex on legs, and no surprise my dick’s already twitching to get at her.

Deciding I needed some air, I nodded at the door and told her, “Be right back.” I headed outside, where it’s snowing like mad. And thankfully cold enough to make my cock deflate.

With a brisk wind nipping at my face, squinting against the blowing snow, I opened the trunk. Glancing around at everything inside, I decided I’d better tuck the wine I’d brought into my suitcase so it doesn’t freeze.

As I’m lifting out our suitcases, and locking up the car, I already know this going to be one long night. Maybe the longest of my life. Lying next to Kendra in bed, staring up at the ceiling, with her close enough to breathe in her intoxicating scent, without being able to lay a finger on her, is going to be absolute torture.

It’ll sure as hell test my resolve. A few years back, I managed to complete a grueling Iron Man challenge, that I thought at the time had really tested my mettle. But I already knew this is going to be ten times harder to get through. Sleeping beside the woman who haunts my dreams, and makes me question nearly every day that I work with her, why I even hired her.

Though if I’m going to honest, I know why. I took one look into those big, innocent brown eyes, and I knew I didn’t want her to walk out the door. So, being a sucker for punishment, I hired her on the spot. Lucky for me, she’s so good at her job, I don’t know what I’d do without her.

So, there’s no way do I want to screw up our professional relationship, just for a little fun between the sheets. No matter how incredible it would be to finally connect with her like I’ve only ever dreamed of.

I notice on the way back to the room there’s a lineup now for the restaurant, and I think I’d better grab us some lunch.

I knock on the door, about to hold up the bag and say, “Lunch is here,” when Kendra opens up, and I can’t believe my eyes. She’s shed her wooly sweater and now she’s in a little white skin-tight tank top, that really shows off her perky twins. And with her butt-hugging jeans, and her hair up in a messy bun, she just looks so damn sexy, I wonder if I should turn around and head back out into the blizzard.

Fanning herself with her hand, she explained, “It’s so hot in here, but I couldn’t see any way to turn down the heat.”

I hand her the bags of food. “I got us some lunch. Let me get my stuff off and I’ll see what I can do.”

She flashed me a pretty smile. “Thanks, Noah.”

After pulling off my coat, and slipping out of my boots, I take a look around and can’t see any controls for the heat, imagining it’s all centrally controlled from the office. So, there’s no way I can adjust it. Which is not good. I had planned to keep my clothes on all night, but that’s not going to happen when the room’s as hot as a sauna.

“I think it’s all controlled from the office,” I finally told her and she just shrugged, I guess accepting the fact we’re be boiling all night.

I notice Kendra rummaging around in her suitcase, before she disappeared into the bathroom. When she came out, I can barely breathe. Still in the skin-tight tank top that really shows off her gorgeous breasts, now she’s wearing a tiny pair of silky baby-blue boy shorts, making her legs look amazing. And she’s got such a beautiful round ass, that I’m almost tempted to bend her over my knee and take a bite.

Resolved to a night of torture, I took a seat at the little table in the corner, and opened up the two containers of veggie soup and unwrapped our tuna sandwiches. Not exactly gourmet fare, but luckily neither of us is fussy.

Kendra came and sat across from me, and said, “Thanks for lunch, Noah.” And now we’re eyeing each other as we eat, both of us kind of smirking. Deciding, ‘What the hell, why not?’ I get a bottle from my suitcase, a couple of glasses from the bathroom, pour us some wine, and settle in for a night I have a feeling I’ll never forget.

I notice the remote control on the edge of the table, and turned on the TV. And I smiled at the way Kendra’s eyes lit up when she realized the original Miracle on 34th Street was just starting.

“Oh, I’ve always loved this movie,” she said, curling her delicate little feet under her to watch it as we ate, making her look so tiny and cute.

I’ve never really enjoyed this time of year. It only reminded me that growing up, Christmas was never exactly a happy occasion. Living with my no-nonsense grandmother, there was no joy in our house. No tree, no lights, nothing. It wasn’t her fault, though. She just wasn’t into kids. Especially at her age, having to start over at nearly 60, when she’d been looking forward to retiring from her job at the library, and then got saddled with me.

Every year, I remember quietly waiting by the window, peeking through the curtains, hoping with everything I had that my mother would surprise me and show up on Christmas eve. I didn’t care about her bringing me a present, I just wanted to see her, I guess to know she cared. But she was always too busy partying with her friends to think about the kid she’d left behind for her mother to raise.

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