Annie Night 01 - Initiation

Business trips have their positives and negatives. Positives include a company paid for hotel room, maybe a lounge with a bar in the lobby, and sometimes free porn if the department P-Card is on file. Negatives include having to be away from your home surrounded by coworkers you don't particularly care for, eating the same terrible scrambled eggs at the continental breakfast (often times with said coworkers), and awkwardly running into your boss at the ice machine at 9PM. Over the course of a few days, this can be fatiguing and have you ready to leave faster than you can click out of a Zoom call.

The final few days of a full 5 day business trip are usually the most difficult. When the one coworker you genuinely click with asks if you'd like to have a drink to end a long day, it sounds like an innocent salvation of comfort. You simply don't say no.

--

The hollow knock of her hotel room door echoes down the brick hallway. I look around as I wait for Annie to let me in.

"One second! Just uh... throwing something on!" I hear her attempt to yell at a moderate volume. I can tell she's a bit frantic. The sounds of her rustling through her belongings are faint yet audible. As she continues to scramble, I wonder if coming to her room may end up being a mistake. Annie is my coworker. This is a business trip. My job could be on the line if I take something the wrong way and cross boundaries. It doesn't help that I've had thoughts about Annie before.. desires, even. She's just never quite shown the slightest interest in me other than laughing at my jokes or simply being kind to me. To some men that might be enough.. but I need certainty. Clarity. An undoubted consent.

After a few more seconds, the door of her Hilton hotel room begins to crack open until it slowly comes to a stop.

"Come on in!" Annie excitedly exclaims, stepping to the side and rotating her arm in towards the room to wave me in. I smile, oblige, and enter.

Her room is identical to mine, which in all honesty shouldn't surprise me as my room is next door. It's different only in the fact that Annie has decided to throw her clothes in a pile on the dark leather couch under the window sill. I imagine this may be what she was doing while I was waiting to be greeted. "Cleaning".

My eyes graze across her room as Annie bends over to get a bottle of champagne out of her small mini fridge towards the bottom of the entertainment center. The first thing I notice about her is the first thing anyone notices about her when they see her - that long, curly hair. It's unique, and gives her a style all her own. Her outfit remains unchanged from our meeting earlier today: a snug black pencil skirt that hugs her frame perfectly and a white blouse, with a white bra underneath to keep things professional. Classy. And yet, as my eyes wander, I notice her suitcase laying unzipped on the floor next to her bed. On top of it rests something colorful that my eyes curiously lock on to. A maroon red bra with a matching thong next to it, both made of delicate sheer lace. I glare for what would be considered a "long second". Annie's professional demeanor has never spoken to me in the way her choice of displayed underwear is at this very moment. Maybe she's just as good at dividing her professional presentation with her personal desires as I am. An innocent business trip, I would imagine, wouldn't require a nice set such as these.

"And here you go," She says in a friendly manner, extending to me a wine glass filled to the top with champagne, "they're the only set of glasses I could find in my room. I hope you don't mind?"

I take the glass in hand and a little bit spills over.

"No, not an issue at all." I reply, chuckling as I do. Annie laughs in return. Her laugh is contagious and I've always been astounded at the sound of it riding the fine line between cute and quirky.. perhaps it's a bit of both.

We did a cheers. And another. And another. And one more, because "fuck work" and "fuck management". Before I knew it, I was nicely buzzed and actually having a good time on a work trip. Annie and I had much more in common than I anticipated. We shared the same type of humor, the same favorite stand-up comedians, and even a lot of the same views on how men and women make friendships difficult or awkward. We had finally made it past the "coworker friend" phase, and entered into the "friend" phase.

Or so I thought.

"So, what does the misses think of you being out here on a work trip? Does she mind at all?" Annie asks, sipping more of her champagne as if it's a hot cup of tea and I'm going to spill the beans.

"No, actually. You'd be surprised. I think she enjoys the alone time." I reply, as we both laugh.

"I don't know how she does so well without you for a week, then. At least for me, if my husband was gone for a week I'd go crazy."

"In what aspect? Missing him?" I ask curiously.

Annie smiles, nervously. A mental debate on what answer to give me ensues, but the champagne gets the best of her.

"Yeah, missing him. His voice around the house. Cooking for him. Watching our TV show. The sex." She laughs and sips her drink. "Sorry, probably not the most appropriate comment, but it's true! A week is a long time!"

At this point we're both laughing obnoxiously.

"Well, if it makes you feel any better, I made sure to fuck her good before I left. Always do." I assure her. It seems she isn't the only one over sharing.

"Cheers to that!" Annie yells, raising her glass to the air towards me. I raise mine as she adds, "to getting fucked good!"

As our laughter calms, silence fills the room and I worry things have become awkward. That is, until she cracked open the door of possibilities for our night.

"Ah, man. I don't even remember the last time I was fucked good. I mean- I remember the last time I had sex, obviously. But good? Leg-shakingly good? That's been awhile. I know that." She explains, and looks down at her drink. I look down at mine and smile.

"Well, would you like to be reminded?" I ask, calmly. My eyes still staring at my drink.

"Huh?" Annie asks, genuinely confused.

"I'm sorry, I'm a direct person." I explain, as I look up from my drink to see Annie staring at me.

"I asked if you'd like to be reminded of how it feels to be fucked good. 'Leg-shakingly good', as you put it."

"I don't understand. Why would you ask me that? You're married."

"Annie, I'm in a bit of a special relationship. You see, my wife and I.. we have this arrangement. I'm her Daddy. I am the dominant to her submissive. She does as I say, in certain aspects of our relationship. Mainly sexual aspects, and almost always for her pleasure as much as mine. We've been this way for some time. In our adventures there came a point where we figured out that she enjoys it when I have sex with other women. With.. or, without her. As long as I tell her about it in great detail that way she can enjoy it as much as I did. Interestingly enough, videos are her favorite."

"I'm confused. She just lets you have sex with other women?" Annie asks, astounded.

I can't help but laugh in response.

"Annie, she doesn't 'let' me. She asks me to. Hell, sometimes I make her beg. Again, I'll be direct. My wife enjoys it when I fuck other women." My bluntness leaves a bit of astonishment on her face, but I can see a part of it makes her blush as well.

"Wow, I've never met anyone in a relationship like that. It sounds kind of crazy. I don't think I could ever do that!" She remarks as she bursts out laughing.

"I know it does, but my question remains unanswered. Would you like to be reminded what it's like to be fucked good?" I ask again, only more firmly this time. Rarely do I ask twice when I'm in this mindset.

"If what you're saying is true.. then yes. I would. God yes, I would." She responds, firmly.

"It's true. Trust me. But are you sure? Once we cross this line, there's no going back. I do value our friendship and wouldn't want to ruin that. I would hate for you to regret your decision due to the champagne and want to take this back in the morning."

"If I'm being honest, I've had some thoughts about you before. Seeing you around in the office, you just have this.. presence. I don't know how to describe it better than that. It's a very masculine aura that isn't trying to prove anything by its existence. It's sexy, and it's always turned me on. I just knew you were married so- you know what.. I'm talking too much. Yes. I'm absolutely sure." She answers, confirming any doubt.

With the clarity I needed now provided, the initiation begins.

"Then kindly go change into that maroon set you brought and we'll start there." I order, pointing at the bra and thong I spied earlier on her suitcase.

"Wow.. you really pay attention! I tried to remember to put these away before you came in, too!" She giggles as grabs them and goes into the bathroom to change.

"Do you want me to put my work stuff back on over it?" She hollers from behind a closed door.

"No. If I did, I would have told you to."

I can tell this is Annie's first time being led by a truly dominant personality. The champagne seems to be helping her get over the newness of it all. She may not know it, but her time as a sub begins now.. and I have hopes that she'll catch on quickly.

A few minutes pass and Annie comes out of the hotel bathroom wearing her sheer maroon bra and thong set just as I ordered. Her body language says she's nervous, but the slightly visible wet spot on her thong says she's very willing.

Annie notices the interest in my eyes as I look her up and down and decides to give me a twirl. Her body is beautifully lean and curved at the same time. Flat tummy, belly button piercing, and thighs that look as though they're begging to be gripped by my large hands.

"Sorry, I get wet really easy.. and like I said it's been a while." She nervously explains as she looks down at the wet spot she's made.

"Don't apologize for being who you are around me. Not now, not at any point of this. I'm accepting you just as you are and my main goal is to ensure that you're happy and satisfied. That is, if you do as I say. You will do as I say, correct?"

"Yes." Annie responds.

"Yes, sir." I firmly assert, correcting her.

I can see a switch turn in her head as she smiles.

"Yes, sir." She answers, this time staring me in my eyes. Her body relaxes as Annie begins to settle into her role as my sub.

"Come sit on my lap. I'd like to feel your body against mine." I order.

"Yes, Sir."

Annie quickly steps over to me and sits on my lap facing me. I take her chin in my right hand and bring her mouth a mere inch from mine, causing her eyes to close in anticipation for a kiss. I can smell the remaining perfume from her work day lingering on her skin. It's intoxicating, but intimacy is something my subs must earn from me.

I press my index finger against her lips and she naturally opens her mouth and wraps her warm lush lips around the tip of my finger. Her tongue gently rubs against the meat of my fingertip as she begins suckling on it. Without a word, Annie takes my index finger completely into her hot mouth. She begins slowly working on it as if it was what she really wants. Her use of her tongue and her willingness to let drool accumulate wherever it wants makes me slightly weak in the knees. Her lips are already glistening around my finger.

I remove my finger from her mouth and grab Annie by her hips. I spin her around in my lap and wrap my left arm around her waist so she can't move, even if she wanted to. My right hand begins running up her curves, from her thighs up past her waist and finally to her breasts. A gentle caress of her supple B cups gives a friendly reminder that a woman's chest doesn't have to be large enough to cause back problems for it to turn me on. Annie's modest breast fits perfectly in my hand and I can even feel her hard nipple grazing my palm through the lace as I sensually feel up what was once "just my coworker".

Annie quietly whimpers as I take my time. Her breathing gets heavier, and I can feel her body getting a bit warmer. Her head rests on my right shoulder and her eyes remain closed, taking in all that's happening.

"Good girl. Let me take over. Let everything go. Allow me to take you as I please." I calmly whisper in her ear.

"...yes, Sir." She quietly responds between breaths.

My hand releases her breast, and reaches downward. Annie twitches the moment my finger comes in contact with the top of her thong. The excitement continues to build. I begin slowly running the tips of my fingers around the inner of her thighs, and it becomes evident just how ready Annie is to serve me.

The small wet spot on the front of her thong is now much larger and is moist to the touch. I tease a little bit, running my fingers to the end of the soaked material and back up again. Annie's unpredictable twitching increases in frequency as I do so.

But alas, I've had enough. I'll wait no longer. I'll save the long foreplay sessions for a possible future adventure. She's mine, at the very least for the night, and so I'll treat her as so.

I slide my hand into her thong and am greeted with her smooth pubic area. As I continue and lift the fabric from her skin to create room for my hand, I can feel strands of her sweet grool stretch away with the lace and break apart. Simply gliding my hand over her lips feels like someone put a liberal amount of lube all over it, but we both know that isn't the case. She seems to have been truthful in admitting she gets very wet, very easily.

With my left arm still wrapped around her waist, her head still restless on my shoulder, I begin playing with Annie's slick clit. My index and middle finger begin softly teasing, causing her to quietly moan and squirm. Her head begins turning side to side slowly on my shoulder as she truly begins to let go.

"Sir, I'm going to.. cum.. if- if you keep going." She stutters.

I stop my every movement and use this as another teaching moment.

"I will give you permission to cum. When you get close, you will ask if you may. Whatever my answer is, you will obey. Understood?" I ask, firmly.

"Yes, Sir." She responds, taking a deep breath of preparation. Where she's going, she'll need it.

I continue taking my sweet time playing with Annie's clit with my index finger whilst my middle finger occasionally teases the entrance in her lips. Her moans begin getting louder. She begins muttering words of affirmation such as "yes" and "please" where she can find breath to do so. Words I've heard in her voice only in meetings are taking on an entirely new meaning tonight.

Annie's body begins trembling, my left arm tightens around her waist.

"Sir, may I cum please?" She asks quickly. It's clear she's approaching her peak.

"No, you'll wait. I'm having my fun and I don't want to stop quite yet." I respond, eager to see how serious Annie is taking all of this.

"Mmm!.. Sir I don't know how much longer I can.. go.. before I cum." She pleads.

"You will go as long as I say you'll go." I assure her.

Annie turns her head on my shoulder and buries her face into my neck. She releases a big hot exhale onto my skin, which only fuels my flame. I begin to feel her teeth press against me, but she's not biting me. Rather, she's biting her own lip in an attempt to hold her orgasm for me. Suffocated moans escape her clenched jaw as she fights her urges for me.

"What a good girl." I think to myself, as Annie continues to breath heavily into my jawline.

"What a good girl.. you may cum now." I advise, granting permission to my very needing sub.

My hand quickens, stimulating her clit even more than I already was. Annie's body stiffens and begins lightly jolting in my locked arm as she reaches a loud and much needed orgasm. I slow and come to a gradual stop as she tries to get her heavy breathing under control. While she recovers with her face still buried in my neck, I kiss her forehead for a job well done. A taste of intimacy for a new sub who obeyed me well.

"What do you say?" I whisper in her ear.

"..thank you, Sir?" She answers, unsure if she guessed correctly.

"Perfect. It makes me happy I didn't have to explain that to you. It means you're beginning to understand what I expect from you."

Annie smiles. My positive words of encouragement seem to mean a lot to her.

"Take your fancy maroon lace off and bend over the bed for me. I'd like to see you bent over really well for me." I order.

"Yes, Sir." She responds, still collecting herself.

As I release both arms I had around her, Annie stands up in front of me with slightly uneasy legs and begins unclasping her bra. It drops to the ground like a heavy feather from a beautiful bird. Her freed tits are perky, nipples are just the perfect size for her frame, and together they're making a great case for B cups to be my new favorite bra size.

Annie grabs each side of the lace thong she has on and begins bending over whilst pulling it down. I get a quick glimpse at the darker shade of maroon fabric directly covering her pussy just before it leaves her skin and also gets left on the floor.

She stands in front of me awaiting my next command, like a good sub. But I want to take a moment to take this in. Looking at Annie completely naked, I recall all the times I imagined her with no clothes on at work. In all those moments in my mind, I don't think she ever looked quite as sexy as she does standing in front of me now. My mind could not fathom a body this perfect under her modest work clothes.

"Sir?" She asks, looking at the floor.

"Yes, my good girl?"

"Will you fuck me hard and rough? I like it hard and rough. As rough as you'd like."

My eyes widen as Annie slowly raises her head and locks eyes with me.

"Yes, I'll fuck you as hard as I think you deserve. So far, you deserve a good hard fucking." I answer.

Her smile lights up this dimly lit hotel room being paid for on our work's budget. Annie turns around, walks to the bed and gets on her knees on the edge of the mattress. As her feet lift off the ground, her ass raises and her face goes down onto the comforter. I stand up and begin taking my shirt off. Followed by my pants. Then my boxer briefs. My hard cock excitedly flops out and sits exposed, and I see Annie move her head to the side and catch a glimpse of what she's about to be given.

"Your cock looks amazing, Sir. Mm, I can't wait to feel you inside me... over and over again." She says, in a confident and sexy voice. She bounces her bent over ass a few times in front of me, begging me to enter.

"Yes my good girl, I know you're going to love it. However, before I do, there's something I must punish you for."

Confused, Annie lifts from her bent over position and looks back at me.

"Punishment? Did I not follow instructions well enough? I'll do better, I promise. Just tell me how, Sir! I really really don't want this to end." She begs.

"We've worked together 10 years. It took 10 years for us to finally make it here. For making me wait that long, you'll be getting a spank for each year you made me wait. So bend over once more, and this time don't break that position again without my permission or you'll have even more spanks."

Annie smiles, and bends over as she was.

"Yes, Sir. I'm sorry for making you wait so long. I promise I'll do everything I can to make it worth-"

*clap*

Stopped mid-sentence by a hard spank from my right hand.

"Mm!" She exclaims through an open mouth as she tries to shut it for silence.

*clap*

Harder this time. Another yelp, but muffled this time.

*clap*

Same strength, teaching her that I am not only her first dominant, but the best dominant she will find.

*clap*

*clap*

*clap*

*clap*

Four in succession all in the same spot as the first three. The last spank being the hardest yet, and as it lands her body jolts slightly forward out of shock. Annie's right cheek quickly turns a flush red.