Secret Santa

Story Info
Holiday Party: Assistant & Boss.
4.7k words
4.47
9.8k
5

Part 1 of the 2 part series

Updated 12/13/2023
Created 12/06/2023
Share this Story

Font Size

Default Font Size

Font Spacing

Default Font Spacing

Font Face

Default Font Face

Reading Theme

Default Theme (White)
You need to Log In or Sign Up to have your customization saved in your Literotica profile.
PUBLIC BETA

Note: You can change font size, font face, and turn on dark mode by clicking the "A" icon tab in the Story Info Box.

You can temporarily switch back to a Classic Literotica® experience during our ongoing public Beta testing. Please consider leaving feedback on issues you experience or suggest improvements.

Click here
PrinDY88
PrinDY88
25 Followers

*All characters are grown adults (28-50) and are of legal drinking age*

It's that time of year, work is supposed to be less hectic because all offices will be shutting down for the holidays.

Of course, you're stuck with your eyes on the screen sending a few last-minute emails so clients don't get pissed off, not to mention your hard-to-please boss, Nick Kringle; the youngest senior partner at the age of 30, of Kringle & Associates. You've been his assistant for just over a year. He has a reputation for being a complex, motivated, playboy.

However, you secretly believe from having spent so many long hours working on files together late at night, there is more to the man who has the money, power, and success than what he shows the public. Sometimes you see him staring from his corner office overlooking the city skyline, brooding, having a scotch and he seems like he is searching for something, or maybe someone?

You can visualize him so clearly; after a long day, his tie casually thrown on the big leather couch in his office, the crisp (usually white) Armani shirt pulled from his pants with the first few buttons undone just allowing anyone a quick hint of his well-defined pecks. The lights from the streets make the natural caramel highlights of his dark chocolate brown hair sparkle, which he keeps as a nice undercut style, with always the hint of stubble neatly kept. His eyes a tantalizing aquamarine, which you sometimes find yourself lost in.

*Ring Ring* The sound of your office line awakens you from your dreams of your boss.

"Holly Berry, Kringle & Associates," your go-to standard phone voice.

"Holly, where the fuck are you? The party started an hour ago!!!" it's your work best friend, Joy Noel; already sounding tipsy wondering where you are.

"Shit sorry, you know how Nick gets, if I don't return every e-mail, I'll probably be out of a job by New Year's, I'll be right down, just have to change," You reply.

"Girl, you know Nick would never fire your sexy ass, now hurry up or I'll have drunk all the candy cane martinis!!" Joy hangs up.

You grab your garment bag that Nick let you hang up his office closet for the day, and head to your private bathroom (being the senior partner's assistant has its perks.)

Before slipping off your clothes you take one look in the mirror, at the age of 28 you still have some nice perky breasts not too big usually around a C or D cup depending on the designer, you have a classic top hourglass figure, and you are fit but not overtly so, unlike most women that you know, your looks have never been an issue.

Sadly your pain comes from your parents who always insisted that you be the best at everything, the classic parental ideology that forces children to become adults too fast and focus solely on academics and achievement. You shake those dark thoughts from your mind. Tonight is about letting go of all the stress from your job, and the pain of trying to be the best at everything you do.

You slip out of your office attire, shimmy out of your black a-line knee-length skirt, remove your black stockings, and replace them with the green and white striped ones that match your costume. You remove your red blouse and remove the straps of your matching lace red bra, unhooking the straps so that your bra is now strapless. You take out the naughty elf dress and pull it over your head and adjust it until it covers your ass so that if you bend over no one will get a full show but maybe a peak at your red cheeky panties.

Usually, at work you have your hair up, but tonight you're letting loose, you let down your mid-back length merlot highlighted brown hair and use your portable hair curler to add just a little bounce and volume.

You fix your makeup and add some sparkles and glitter to make you into a sexy elf, and normally you would wear a hat with this costume but you want your sexy locks to shine in the lights, so instead you add some product that adds a nice peppermint scent to your hair along with some glitter. You add some sparkly red lipstick and apply your favorite perfume (Sexual Noir from Michel Germain). Before you lock the doors, you put your garment bag back in Nick's closet. You take the key fob and use the hook that you bought that attaches to your garter belt so that you don't lose it.

You take the elevator up to the top floor, which holds the office party room, it also has access to a gorgeous patio with couches and a hot tub for the office staff to use to relax. The holiday tunes are blasting throughout the room, everyone dressed as holiday characters, which is a strange sight most of the time but for this office, it's downright unbelievable. You make a beeline for the nearest bartender and request the specialty 'Naughty Candy Cane' holiday-themed cocktail.

As you make your way through your co-workers on the dance floor and tables, you see your bestie Joy hanging with some of the other assistants. You run behind her and hug her from behind.

"Surprise!!" you say as you wrap her into a hug.

"It's about time you got your young fine ass down here" Joy replies.

These comments from Joy are common, she is in her late 50s and is the office manager, she always gets along well with all the younger female assistants, sometimes reliving her youth through their lives.

"Holly, do you want to get some fresh air?" Joy asks.

"Yeah, sure let's go onto the patio," you reply and head outside to the heated patio.

"Alright girl, let's get real, when are you going to move on up, you have so much potential, you have your law license and passed the bar, why are you still working as his assistant?" Joy asks, moving into mothering mode.

"Joy, we have been over this, being Nick's assistant will open a lot of doors for me in the future, I just got to show him I can do more and hopefully I can prove to him that he can take me on as his junior associate but I can't just ask him."

You know Joy has a point but the real reason you don't want to possibly risk your career is you have a huge crush on Nick, and you secretly think that he likes you back, the casual glances and hungry, determined looks that you secretly share while working on those files late at night, and any wrong move could wreck not just your career, but his as well.

"Speaking of Nick, where is he? he told me he was going to show up to this thing," you mention to Joy.

Joy gives you a devious stare, expecting you to say more.

"Stop looking at me like that" you reply.

"I've had enough of you not telling me the truth, you know I can keep secrets, I have been here way too long and know all the tea, so spill already" she inquires.

"Joy enough, I love you girl but nothing is going on between us, he is MY BOSS" you reply but Joy notices the spark of lust in your eyes.

"OK, OK! I won't ask again, but no one here would blame you or even throw you under the bus, Nick is hot and intelligent, I know people think he is a motivated dick but that's just his lawyer persona, I think there's more to his personality then people are willing to ask him to share...maybe... he just needs the right woman to show him that it's okay to be himself and not what is expected of him." Joy says as she gets up and goes back inside.

You continue to sit outside pondering if what Joy just said is true. You soon find yourself back inside dancing and having more drinks, some people start coupling up and disappearing either going to find private offices or returning to an apartment. As the night wears on there is still no sign of Nick.

All night you have been waiting to get a chance to see the Santa that the company hired, the line finally goes down so you go to grab a picture. He pats his knee and in a deep husky voice (he must be younger than you expect) says "Grab a seat, what's your name? Have you been a good or naughty elf this year?"

Maybe it's the four drinks you've had tonight, or that this "Santa's" cologne is delicious but you let out a naughty giggle and in a seductive voice you reply to this unknown man in a Santa costume "I'm Holly Berry, Santa, giving him a lusty look, his eyes looking familiar and to be honest, I think I've been a good girl and a naughty one."

(Santa seems to almost shift his hips at your remark, and you see his eyes very briefly look you up and down, you start to wonder, could this be... Nick??)

Santa clears his throat in a husky breath and says to you "Well, you know Santa appreciates honesty, but he can't reward a naughty girl, but if she can prove to me that she is sorry for her naughty mistakes, she may be forgiven, in which case I will work hard to give her what she wants for Christmas."

"Yes sir, I feel terrible about the 'naughty' things I've done and I assure you I will do my best to prove to you that, I am a Good Girl," you reply seductively.

You look the 'Santa' straight into his eyes at these last words, pretty sure you've figured out who is really in the Santa coat, pants, and small fake white beard. You applaud his effort but he's not fooling you, but you play along, if he wants to play this game, you can play it back just as much.

"OK Holly, what do you want for Christmas?" says 'Santa'.

"Well it's kind of a secret, can I whisper it?" you tease.

"Of course" he replies. (You see him swallow slowly, his adam's apple moves up and down).

Just to tease him some more you wet your lips as you lean down and whisper sexy into his ear "What I want for Christmas, is for my boss to notice me for the lawyer I can become... but besides that.. (you sigh into his ear) I want my boss to take me like the naughty slutty 'elf' that I am, the one who can barely control himself when we spend late nights together, I want him in that hot tub, I want him in his office, my office and anywhere else my sexy, delicious boss wants to fuck me." You add to your teasing by lightly nibbling and sucking on his ear.

Without him saying a word you slowly leave his lap and as you slowly and seductively walk away, casually bend over just enough that you can maintain eye contact with him, so he can still see those stockings and your ass cheeks peaking out of those cheeky panties.

Another hour passes, and the catering and bartender staff have all left, the last of your co-workers have left and it's now just you and 'Santa'. You are trying to avoid looking for him, so you try and start cleaning up a little.

The husky voice behind you startles you, "You're a naughty elf!" 'Santa' grabs you by the arm and turns you around so you're facing him, still in the silly costume and feeling the need to play the game, you look up and suddenly realize he has you just under the mistletoe.

"I'm only naughty, for one person, and he doesn't seem to be here," you say teasingly.

"Maybe he is here, maybe he's not, but I do know what he wants, and what he wants is... You!", Santa says.

He pulls you in close roughly pulling your lips to his giving you a hungry kiss right under the mistletoe.

You pull away, lips still inches from each other and you moan gently and say "I think it's about time, I get to unwrap and see who my 'Secret Santa' is."

You start by removing that heavy coat, slowly slipping it off his strong shoulders and down his fit arms. Underneath he is wearing his signature Armani white button down and you slowly and teasingly unbutton each one, once they are all undone, you run your hands down his pecks and what you now know is an amazing washboard stomach, you can't help yourself, you run your hands from his collarbone down and around each peck and just around his small brown nipples, as your hands lower teasing each individual ab and watching him flex against you and hearing his breath catch in his throat.

You run your hands back up his front and then around his neck and you remove that silly hat and can see he tried very hard to hide his perfectly styled brown auburn hair. You move those hands delicately down his jawline and remove the silly excuse of a fake white beard, finally revealing that handsome face that you have been resisting for so long.

"Well, look who decided to show up" as you look lustfully in his eyes.

"I knew I could only fool you for so long, but I didn't want the others to know it was me, I am so tired of being 'the hard-ass, the one who always has to be determined and motivated, for once I just wanted to be seen like everyone else" Nick sighs deeply, seemingly unburdening his soul to you.

"I always have felt, that you were more than just the 'youngest senior partner, the hard-ass, motivated determined young playboy who doesn't let anyone stand in his way' I knew there was more underneath, but it wasn't my place to make you show me who you are, I just hoped that maybe you would," you tell him sincerely.

"I am also 'somewhat' (you wink) sorry for coming on to you, I know it's inappropriate, especially since you're my boss. I also don't want you to think I came on to you because I want some special treatment or promotion." You say suddenly as some form of logic returns to your brain.

"Holly, I would never jeopardize your career or mine, by entering into something with you for 'a promotion'. I have seen what an intelligent woman you are, and how your legal mind works. I have wondered why you have not applied to any internal associate positions because I believe you have a real knack for advocacy and working on legal issues. However, I will not deny that I have not wanted you for months, I have spent hours, days, and nights with you, getting to know you. You're so beautiful, sexy, and intelligent. Anything that may happen, between us sexually/romantically has no bearing on how I view you as a colleague." Nick reassures you.

You can honestly not believe this conversation is taking place, but suddenly the vibe between you changes. Both of you are looking at one another with a hunger and lust that has been building for months, and the hours you have both spent alone dreaming of fucking one another starting to take over your minds.

"Now, I believe you mentioned you wanted me to take you and let you release the dirty naughty girl you have been hiding from me" as Nick's voice turns into his husky sexy deep bossy tone that has always turned you on. He grabs you and cradles you into his arms and to the elevator. He presses the button for the office, and as the doors ding open, he realizes he can't get his fob while he's holding you. "Shit..." he says.

"Don't worry boss, I always come prepared" you reply, as you slowly tease up the skirt of your costume, letting him get a view of your garter and stockings, and you pull off the fob to the office door. Nick's gorgeous eyes darken with lust as he sees what's hiding underneath your dress.

As you hold the fob up the reader, he takes you into his office and lays you down on his nice soft couch.

He immediately starts running his hands hungrily all over your body, he leans his body on top of yours and says "Fuck, you are so sexy", as he kisses your lips and down your jaw "You know," he says with a determined look and laugh, "I have a secret apartment connected to this building, that no one knows about, would you like to see it?"

As turned on as you are, you are also shocked, "Why do you have a secret apartment, is it some sort of sex dungeon?"

He laughs "No Holly, I am not into that, I have another apartment that is my home, I keep the other one for the media so that I am not hounded all the time."

"Oh, well then...okay, is it far?" I ask.

"Nope, not far at all I can show you where it is, come to the window." He says as he grabs your hand pulls you up and takes you to the window, he shows you a moderate-sized glass building, that is basically across the street.

"I always thought that was an office," I reply.

"Good, that's how I want it to look, the bottom floor is a large underground where I store my cars, but it also has a tunnel that connects to this building's company underground parking lot. No one knows about it because I designed it to look like just a service entrance.

The lower level is a lobby, where I have 24/7 security staff that monitor that building as well as this one for extra precautions. The security staff employed solely at this office building do not know about the other one. The main level is my apartment as well as a private office, and there is a floor above with an indoor pool, hot tub, sauna, and gym." He says.

"So would you like to take a short ride with me?" He asks.

As he wraps his arms around you, your back pressed against his still naked chest.

You thought if you and Nick ever hooked up it would be here at the office, taking a risk about being caught, but he wants to show you his home, this is becoming more intimate than just an office party hookup.

However, there is a voice inside your head that says maybe it's a good idea to have your working relationship and sexual relationship in separate places, that way no one will find out and you can still keep your professionalism.

"Show me!" you reply.

He takes your hand and guides you down to the underground parking lot, there is no one around luckily, he takes you to what you assumed was an emergency exit, but as Nick opens the door, you realize, it's a tunnel but not a grey concrete tunnel, it is adorned with the most amazing professional street art murals, there is also a small golf cart, he takes your hand and guides you into the cart and you travel through the tunnel, it's only like a three-minute ride. You exit the other end and see an array of high-end luxury cars and some older classic cars, he takes you to a private elevator and taps a button, the elevator opens straight into the most high-end yet still modern manly type apartment you have seen.

"Now that you have me here all alone, what are you going to do with me?" you ask mischievously.

He grabs you by the waist and lifts you, you wrap your legs around his waist as you begin to make out hot and heavy, finally allowing your bodies to one another. He expertly walks you to his bed and lays you down onto silky sheets and the softest pillows you have ever felt.

"What I want to do Holly, is get you out of that dress and leave you in just those stockings for the moment, then I intend to devour your body giving you the pleasure you deserve, I want to take you upstairs to the hot tub and sauna, and then back down here to this bed, where we can either continue if you're not too tired or sleep and by the way, I have no plans for the next few days before family obligations for the holidays so I do intend to make this last for as long as you want."

My mind is spinning, with desire, and hornyness but also melting in the respectfulness and intimacy he is showing you.

"I am not going anywhere, you can have me all day and night until you need to leave" you reply, you're not sure what is going on here, this is more than just naughty sex with the boss, but you would be an idiot to not see what happens.

He grins lustfully and says "Now, despite what you may have read or heard, I am not a Dom, I like to be in control sometimes but I like it when a woman knows what she wants and asks for it.

I will only respectfully call you dirty names, never in a degrading or humiliating way. For me sex is not about one person's pleasure over another, it's about giving and receiving pleasure from one another, wanting and desiring each other. I will never intentionally hurt you, nor do I want to be intentionally hurt, I get pleasure from pleasuring my partner, knowing I'm making her feel good gets me hot, I would hope it would be the same for my partner in reverse. If we continue any kind of personal relationship we will discuss other fantasies and kinks but for right now I just want to make sure you are okay with what I've discussed."

To many people, this may seem like it's killing the mood but you know this is just his lawyer mentality trying to control and be aware of all liabilities, which for you, is why you're so attracted to him.

PrinDY88
PrinDY88
25 Followers
12