The First Day (is the Hardest)

I stepped into the office building with a wide smile on my face, much to the confusion of everyone else there. Perhaps it was just because I was just coursing through the high of getting my first job, while everyone else there had been there for some time, but being inside this large, open building, with nice tile floors and a receptionist up front at a fancy wooden desk, seemed almost heavenly to me. It was definitely better than the alternative, for certain. I stood tall in the air conditioned entrance area, taking the feeling in; it was the last time I would be able to feel it for the first time.

As I passed by the receptionist, I gave him, an older man with a grey comb-over dressed in a sports coat, a wave. He waved back, and off I was on my way towards the elevators.

At the elevators, there were several people, a sea of dully-colored button-up shirts and black slacks waiting for the doors to open. As one arrived, they filled it up completely; even if I tried, I wouldn’t be able to fit inside with everyone else. When that elevator went up, I pressed the call button, hoping for one to come my way, and not before long, one came to pick me up.

Stepping inside, I took note of the mirror that faced me, and the twin guard rails that ran parallel to where I was looking. It was such a minimal space, the perfect place for a worker to make sure their outfit was on straight and maybe do some last-minute touches on makeup; like there was anything else for an elevator to be. It was a perfect time to look myself over, check my clothes, make sure that my hair was right, and to see if there was any breakfast still in my teeth. After making sure everything was good, I couldn’t help but think about the interview that happened.

It went really well. Granted, I wouldn’t have been in here if it hadn’t, but the person scheduling the interview, a man very similar to the receptionist, was very fun to talk with and we hit it off personally as well as professionally. There was only one thing that bothered me about it at all, though, and that was he mentioned that Ms. Fletcher, who was supposed to be my boss, wasn’t in on account of vacation and that I’d meet her on the first day.

It left me wondering who this Ms. Fletcher could even be, but as the elevator beeped and opened, leaving me to find the open office under her direction, I knew that even my best guesses couldn’t help me figure it out. Regardless, whether she was an old woman or a greenhorn like myself with a business degree, I was ready to work for the company; any more time not working would have driven me insane.

I entered the open office, and saw a bunch of desks, almost each of them occupied not only with a computer and stack of papers, but someone already sitting down and working. The sound of clicking keyboards and the occasional discussion about work filled the air. At the very front of the office was an unoccupied desk, ostensibly for the boss that was apparently on a business trip when I was doing my interview.

The other unoccupied desk was near the boss’ desk, and as quickly and quietly as I could, I slipped into the seat and started looking at the papers that were on my desk. As I sat down, the person next to me, a man who wore a black button-up and thick glasses and looked to be a few years my senior, pulled his attention away from his computer and looked at me.

“You’re the new guy?” He asked.

I looked away from the computer and at him, and nodded. “Just got hired a week ago. It’s my first day.”

“You know what you’re doing?”

“I just have to copy all these spreadsheets, right?”

“More or less. You can probably get away with doing that for now, but eventually, you’ll have to use formulas to make sure every aspect of the company’s bottom line is accounted for.”

I nodded. As long as I got paid for doing this work, I was fine with it.

“You seem to have a pretty heavy workload, too,” he added, eyeing the stack of papers next to me. “I definitely didn’t have this much work when I started out. Now that I have some seniority, they’ve given me a bit of slack, but I didn’t realize just how much they’re giving the new guys.”

“Should I talk to the boss about it?”

“I don’t know,” he remarked. “She said that she’ll be back today, but if she was, she’d probably be back by now.”

The conversation died down, and immediately, both of us returned to work on our spreadsheets, becoming a part of the noise that filled the room. It was oddly soothing to listen to, and helped me stay productive. However, the words that my coworker had just given me stayed in my head, as if they were etched in my brain. You have a pretty heavy workload. I had expected it–they have busy work to do, after all–but hearing those words made me a bit concerned. Once the boss showed up, I’d have to talk to her about it.

However, as soon as the thought filled my mind, the clicking of keys was undercut by the sound of high heels clacking against the floor. Thinking it was one of my coworkers returning from a break, I paid it no mind, until the sound stopped filling my left ear and started filling my right. A chair rolled and someone sat down, and immediately, the coworker next to me spoke up.

“There’s Ms. Fletcher. If you have anything to say to her, you should say it.”

I nodded and stood up, walking towards the desk. Immediately, the diatribe that I had in my mind about how much work I had disappeared as I took in the sight of my boss.

At the desk in front of me, there sat an older woman. She had to have been in her mid-thirties at her very youngest, but her long, brown hair didn’t have any hint of grey in it. A pair of red glasses adorned her face, framing her dark brown eyes and bringing attention to a mole right underneath her left one. A bright lacquer of red highlighted her lips against her fair skin. And although she was sitting down, I could see her white dress shirt trying its best to hold back her curves, buttons straining against her chest not to break. She looked up from her computer and gave me a wide smile, one that seemed to rattle my very core.

“I’m Ms. Fletcher, your boss. And you are?”

I gave her my name, surprised that I almost ended up choking on the words.

She daintily stuck her hand out. I made sure to grab not too harshly, but with enough firmness. “Nice to meet you,” I said.

“Nice to meet you as well,” she said, her voice a sonorous alto. “I’m so glad to have someone like you on our team.”

I held back the nervous chuckle that wanted to come out, and kept my gaze on hers, her own shining with a mixture of enjoyment and a slightest bit of mischief (although that might have been me overthinking it all). As I let go of her hand, hers lingered, holding it there for an extra second. A rush of what felt like ice shot up my back, and Ms. Fletcher let out a small giggle.

“It’s always nice seeing people so young and energetic joining us. Now, if you have any trouble with any of your work, don’t hesitate to ask me, okay?”

I nodded. “Understood.”

She returned her attention to her computer and brought her hands back to her keyboard, the tapping of her keys almost a constant stream of noise. With her attention back to her stuff, I turned around and returned to my desk, where I was greeted by a spreadsheet that I thought I understood enough to get started on, and thus, I started typing away, trying my best to put all of my attention into typing out my assignment. I needed to do the best I can, at least try to make it look like I was there to work.

However, even as I typed, my mind was in another place altogether. I was barely thinking about the cells I was filling out. All I could think about was Ms. Fletcher. Her warm, comforting voice, her mature body and the clothes that struggled to contain them, the way her hand felt against mine; it was difficult not to keep my attention on her when I could simply look up above my monitor and look at her instead, putting all of my attention into looking at her. It was so ironic, knowing that the one thing that was keeping me from working my best was my boss, but I wasn’t the one who decided that she should be so sexy.

I could thank whoever did later. I needed to work on my spreadsheets. Throwing my thoughts aside, I looked at the papers stacked on my desk, and went to work, typing up as much of a storm as I possibly could. I had a long day of this ahead of me, and I wanted to make sure that every sheet was done before I went home. I needed to make a good impression on this company, and more importantly, make a great impression on Ms. Fletcher.

It was impossible not to get my mind off of her, though. Every so often, I would look up and see her, sipping on the cup of coffee on her desk, or typing up a storm at her computer, or talking with a coworker about something I couldn’t care less about. The smile on her face was addicting to see, as was the intense stare she gave as she worked on her work. Each glance was fleeting, though, and before she could notice, I returned to my work, trying to be as diligent as I could be.

However, I wasn’t diligent enough, Eventually, Ms. Fletcher noticed. Maybe I stared for too long once, but there was a moment where, in my looking up, our gazes met. Immediately, my glance shot back down to my work, where I’d keep my eyes glued onto my screen for as long as I could. Even if I wanted to look elsewhere, I didn’t want to look like I was distracted. Thus, I worked, even as the thoughts that lingered in the back of my head kept rampaging, trying their best to be a distraction of the highest caliber.

Eventually, when I decided to look up again, I saw that Ms. Fletcher was staring over her computer and at me. I could barely see the corners of her lips from where I was, but I could see that they were the ends of a bright smile. It felt surreal watching the gaze come from her, and I tried my best to hide the pang that went through my body.

Her smirk grew, and then she returned her attention to her work. As did I, looking down at my computer, my fingers tingling a bit from what had just happened. I shook myself out of the stupor, though, and started typing up more of the spreadsheets.

Then, next to me, I heard some joints popping. I looked over at the coworker sitting next to me, stretching with his arms as high as he could possibly bring them.

“I’m going to go on my break now.” His words were matter-of-fact, and he stood up and walked out. I was bereft of company, but now was the perfect time to test something.

I stood up from my desk and walked over to Ms. Fletcher’s desk.

“Excuse me,” I said, trying my best to sound calm and collected. It felt weird; there was a lump in my throat, and as I spoke, I could feel my heart starting to race. She was my boss, and yet, it felt like I was talking to someone more, well, je ne sois quoi.

Regardless, she turned to face me, that plump smile on her red-lacquered lips. “Yes, honey?”

The lump in my throat grew larger, and I almost gasped on it. Whether it was just a term of affection for her coworker or something more I didn’t think about, nor could I care. I had something to do, and now that I was standing in front of her, I couldn’t back out.

“I think I might need a bit of help with these spreadsheets. Do you think you can help me out?”

“Of course,” she said, standing up from her chair. I led the way, listening to the clacking of her heels behind me. It was so percussive, breaking the quiet buzz of the workplace, but at the same time, so soothing. Perhaps it was because I knew who was behind each of those steps that I felt that way. I sat down, and she stood right next to me, looking down at both myself and the stuff on my desk.

“What seems to be the problem?”

“Well,” I said, “I’m not necessarily sure what these numbers here mean,” I said, pointing to an arbitrary place on the spreadsheet I had yet to fill out on the computer.

Pushing her glasses up with a single finger, she leaned forward slightly, glancing at the numbers that were written down. She stared at them, her gaze brilliant enough to drill a hole through the paper if she could, before standing up, and, strangely enough, bringing a hand to the top button on her shirt. Undoing it, she exposed more of her skin, her collarbones, and the slightest hint of her cleavage. I kept my focus on her face, but my attention was elsewhere, peripherals scanning her curves as she exposed more of them.

“It’s quite hot over here, don’t you think? We’ll need to get a fan for this area.” I could tell immediately that her words were bullshit, but I wasn’t going to call her out if she was going to expose herself like she did. It was definitely a lot hotter now that she was like that, so she wasn’t necessarily wrong.

“Y-yeah,” I said. There was really nothing else for me to say, and once more, she leaned in, the cleavage window growing more as her chest fell in her forward bend. I’m glad I didn’t say much else. I wondered if she even realized that I was barely paying attention to what she was looking at.

“Okay, I think I know what your problem might be.”

“And what would that be?”

As she spoke, I paid no attention to her words. I knew what she was talking about. I just wanted to look at her, and the more I looked, the more I loved what I saw. Outside of the tight shirt, she wore a black pleated pencil skirt that hugged her hips and thighs so tightly I didn’t know how she could walk in them, along with sheer leggings that covered every bit of her calves and thighs that her skirt didn’t. It was an addicting sight.

“Is there something wrong?”

I pulled my attention away from her body and towards her face. Shit. I just got caught looking at my boss like that, and by my boss herself, at that.

“No, no. Keep going.” I wanted her to keep talking so I could continue what I was doing. Perhaps it was a bit lecherous, especially for work, but I couldn’t help it. Her mature body had a level of allure I simply couldn’t put into words, and with the sonorous alto of her voice accompanying it, I could feel myself getting lost in it.

As if she knew I was staring at her, Ms. Fletcher brought her hand to her shirt and undid the second button, opening up her cleavage window even more and letting me take a peek at her bra. My eyes widened at the sight of lace, and I could see her smiling in the corner of my eye. I had no idea what she was trying to tell me, but I brought my hands to my lap, trying to hide the erection that was starting to form in my pants. She went on without a hitch, though, talking as if everything were normal.

“Does that make sense?”

I’m brought back to my senses by those words, her telling me that she was done with her explanation. “Mhm,” I said.

“Good,” she replied, standing up. “I’m glad you’re starting to get the hang of the company procedures. Keep it up.” Her smile was warm and forgiving, even for the crime I had committed of staring at her like I was an animal wanting to tear the buttons off her shirt myself. She had awoken something in me, something I didn’t want to have awoken at work, and the smile on her face was so innocent, as if she didn’t know what she had done even with her years on this earth as experience.

She turned around and started walking back to her desk. I watched her strut, her hips shaking as if she were performing a sashay down a catwalk and she wanted her skirt to twirl with every step. Once she was at her desk, she sat down, all the buttons on her shirt done properly like she never even made a pit stop to my desk.

She gave me a flirtatious smile and then returned to her work.

I kept up my schedule of typing out cells and looking at her, the curiosity now replaced with more primal urges. I kept quiet, though, my breathing at most a quiet huff as I typed out the numbers, trying my best to keep my mind off her. Looking down at my screen, I re-read a few of the cells that I had just filled out.

“I want to bend her over and fuck her until her legs give out,” was filed under something about last month’s management.

“Those lips would look fantastic wrapped around my cock,” was filed under next month’s expenditures.

The more I read, the more I was shocked with myself. I was barely paying attention to the numbers. All that was on my mind was Ms. Fletcher, her curvy and mature body, and how fantastic she would look naked and begging for me to fuck her even more. Quickly, I deleted all that I could, making sure to clean up my spreadsheet as much as I could.

I brought my hands away from the keyboard for a few seconds, and took a deep breath. I needed to actually concentrate on what I was doing. As much as the fantasy of Ms. Fletcher looking at my spreadsheets, rife with the thoughts of bending her over and treating her in ways that no man should treat his boss, filled me with a level of excitement, it was dashed knowing that there was absolutely no way she wouldn’t read that and immediately fire me on the spot. It would have impressed her more if I actually did the work, and thus, I started focusing on what I was doing and plugged away, making sure the spreadsheets looked like the papers that were stacked on my desk.

I typed throughout the day, only pausing as more people started to leave the building. There were a few people who would pop into the room every so often to talk to some of my coworkers, and coworkers would walk in and out to have their breaks, but I persevered. There was too much work on my plate for me to justify having any free time like that, and there was no way that I wanted Ms. Fletcher to stand up, look around the computers, and see that I filled a cell with a lurid fantasy instead of the work I was supposed to do.

“Are you sure you don’t want to go on your break?”

I turned away from my spreadsheets and towards the familiar voice: it was Ms. Fletcher herself, standing there with her hands at her sides. “You’ve been working all day and I wouldn’t want you to burn out. I think you should relax.”

“I think I’m fine for today,” I said before turning around and doing more work. However, before I could get too far into my work, I felt something large and soft press up against my shoulder blades.

Ms. Fletcher’s fingers wrapped around my shoulders. “That’s too bad,” she said, her voice but a huff against my ear. “I was thinking of going on my break, too, but if you’re so inclined to keep working, I won’t stop you.” She pressed her body even more against mine, as if trying to turn me into a boiling pot of hormones stirred by the gentle circular motions of her fingers as she massaged my shoulders. After a few seconds, each feeling like an eternity, she pulled away, and walked off as if she had done nothing.

I considered joining her, but I couldn’t bring myself to do it. It was my first day, and I would have been dead if someone found out what happened during our collective break. Even with how hot she was, she was my boss. Hell, she was a part of the company; I couldn’t perform any misconduct towards her lest anyone figured out about it. As much as I wanted to follow those swaying hips towards whatever break room she was going to, and the invitation, I had to stand my ground.

As she disappeared, and I returned to my work, I regretted that decision immensely. Because of those actions, me typing out those lurid fantasies earlier looked like productive busywork compared to how I was working. The more I typed, the more misspellings I made, and the more those lurid fantasies kept trying to slip from my fingers. Even if I was diligent enough to erase them when I was only two letters in, I could see the full text I wanted to type out, raging diatribes about “putting Ms. Fletcher in her place” and “making sure she gargles my cum like it’s her life source” filling cells that were meant to be about things that I couldn’t even think about.

I clocked out for my break not long after and spent it all in the bathroom.

Even after I had finished my break, though, with the furious amounts of toilet flushes and toilet paper used, the moment I was back in the office, and forced to stare down Ms. Fletcher at her desk, the urges that I thought I satisfied had come back, boiling in my belly like I hadn’t used my break trying to get rid of them. I almost ran to my desk; I was in her eyesight and the last thing that I wanted was to deal with her seeing a raging erection tenting my pants.

Once at my desk, I kept typing, going through the pages of the spreadsheet. I was impressed at how much I had been able to do today, even with all the distractions around me and in my mind. I thought that the work was going to be much longer, but as time ticked by, page after page was completed. Coworkers came in and left, and not before long, as I finished filling out the pages, I was the only person left in the room at my desk.

The only other person was Ms. Fletcher herself, standing up from her seat and dramatically wiping the sweat off her brow. If only she knew the things that were going on in my head about her, and the amount of times I stared at her after she came back from her break. Our gazes met, and she gave me a warm, comforting smile. “Are you almost done with your work?”

I finished typing in my last number at that exact moment, and nodded. “I’ve just finished,” I said as I saved my spreadsheets and turned off my computer. Once it was fully shut off, I stood up and slipped a hand in my pants, making sure that the erection that hid in my slacks wasn’t too apparent. With that insurance complete, I headed towards the exit, and Ms. Fletcher followed me, perhaps a bit too close for my comfort, down the hallway.

“My, my,” she said, filling the silence between us as we reached the elevators. “I’m surprised we found such a hard worker. I’m so glad to see someone so full of energy in the office these days.”

“Why, thank you,” I said, nervously shifting my hands at my sides. I didn’t know exactly what to do, and I pressed the call button, hoping an elevator would come down soon so we could get out of here. I needed to get through a lot of relief tonight if I wanted to be any bit productive tomorrow.

“No, seriously,” she said, “in my fifteen years of working at this company, I’m so glad to have found someone who works hard and has such youthful energy.” She leaned in, subtly pressing herself against me. I barely noticed the feeling of her side against my arm, but it was enough for my skin to start burning.

Before I could respond to her comment, the elevator had arrived. I stepped in, and Ms. Fletcher stepped inside the elevator as well, turned around, and bent forward slightly to press the ground floor button. The fabric of her skirt hugged her ass tightly, allowing me the slightest glimpse of her lingerie underneath. I felt my heart skip a beat as I noticed the imprint of a thong, immediately bringing another wave of unsavory thoughts.

Before I could fully parse what was going on, though, an alarm sounded for a few seconds, bringing me back to reality. If it weren’t for that, the sudden shaking of the elevator would have brought me to my senses. My eyes were just as wide as hers, however my gaze was filled with genuine shock. I could tell that she was acting, and she wasn’t even trying to make it hidden.

“Oh, no,” she said, her tone the obvious kind of faux panic that felt more like teasing than anything else. “The elevator stopped! Whatever shall we do?”

I wasn’t sure whether the words themselves or Ms. Fletcher’s tone of voice scared me more. She seemed rather happy about this development, where it was just the two of us, alone, in a small room where, presumably, we were left to nothing but our whims for a good period of time. I didn’t know what was running through her head, but it was a lot to handle all at once.

Ms. Fletcher stood up, and she turned around, noting my expression. Worry covered her face. “Is everything okay?” She asked, her voice just as playful as it was concerned. “You look a bit tense.”

Considering how she was acting, and how the elevator just gave out like that, of course I was feeling tense. It was bad enough that I learned about how hot my boss was, but to have her teasing me all day like this left me pent-up. And to make things worse, we were still in the office; I wasn’t going to tell her exactly what was on my mind now, and I still didn’t think I should even if we weren’t in the same company. And because of the elevator, it was tantamount to being stuck in a small room, alone, letting myself simmer in these thoughts.

Alas, words came out. “M-Ms. Fletcher–”

Ms. Fletcher took a step towards me, with just enough distance between us for her breasts to graze against my chest. She looked up, and with a coy smile, said three words.

“Call me Annabelle.” After that, a brief pause. Then, “we’re not in the workplace anymore.”

“Uh, Annabelle,” I said, the name weirdly rolling off my tongue given it was my boss’, “you’re close.”

Annabelle’s smile grew. “Well,” she began, “I want to make sure that all my employees’ needs are met, and considering how great of a worker you’ve been…” she stepped forward once more, pressing her body against mine, and I felt goosebumps forming on my back as she ran her fingertips against my legs.

“I’ve seen the looks you’ve been giving me all day. If you weren’t such a cutie, I would have reported you to human resources.” Her fingers started drawing curlicues as they made it halfway up my thigh, stirring more sparks throughout my body. “And even now, you’re looking at me like you want me.”

Taking another step forward, she pinned me between the wall and her body, the softness of her chest pressing up against my pecs. She looked down for a moment, saw the contact, and looked up into my eyes, a smirk forming on her lips. Grabbing my wrist with her free hand, she slowly brought it up my side and eventually to her chest, where she would rest it atop the highest button. Pressing herself against me just a bit more, I could feel the clothing growing a bit slack, the button rubbing up against my thumb.

“Come on, I know you want to,” she said, her voice low and husky.

She was right. I wanted to. I couldn’t not; it was like my hand was acting on its own when I grabbed her shirt and pushed the button through its slot, undoing it and exposing that slight cleavage window from before. However, now, I could look down without any impunity, with her large breasts pressed up against me. Her hand once more grabbed my wrist and slowly brought it to the next button, and the button after that, slowly exposing more of her bosom and the black lace bra that covered her chest.

Once my hand was at her mid-torso, and her brassiere was fully exposed, she grabbed my wrist and led my hand to her right breast, hand grazing up against all the flowery lace details. I took it in, accentuating the weight and softness of her breast as it overflowed in my hand, and I slowly squeezed, listening to the soft moan that leaked from Annabelle’s lips.

Annabelle didn’t give me any more moans to listen to, though, as she leaned in, pushed herself up as much as she could, and pressed her lips against mine. The tastes of caramel and coffee intertwined in her breath and lingered on her lips, an intoxicating bitter cocktail with just enough sweetness to keep me wanting more. Our lips meshed, and the hand on her breast started squeezing in earnest instead of curiosity, earning quite a few moans from her.

It wasn’t like Annabelle was submitting completely in the kiss, though; her hand slowly grazed up and down my side, thumb scanning my musculature. The hand on her thigh moved upwards, growing ever closer to her target, which was now easily visible through the fabric of my slacks. Before she could take a hold of it, though, she pulled her hand away, deciding instead to press her thighs into me instead. I groaned, trying to resist the appeal of the warmth of her thick thighs as she tried to use them to submerge my crotch.

After a few grinds, Annabelle pulled away, the smirk on her lips grown even more, and her eyes having grown darker. However, before any words could be exchanged, she pushed herself off of me and turned around, leaving me against the wall.

“Mmm, I think I wouldn’t mind having him as a personal assistant.”

With a slow sway of her hips, Annabelle started dancing in front of me. She ran her hands up and down her sides, tracing the pinch of her waist and the fullness of her semi-clothed bosom. Her teeth slowly sunk into her lower lip, playing with it just enough for me to notice as her lips curled upwards into a smirk. She slowly undid the final buttons on her shirt with a final pass upward. As her hands reached her shoulders, she shrugged and brought her hands down, thumbs hooking into her top and slowly pulling it down and off her body.

My mouth watered at the sight of her chest, finally free from the constraints of her shirt. Even though the struggle against her shirt was obvious, I didn’t realize how large her breasts were until they bounced against her bra, the thick straps of her bra momentarily struggling to keep themselves intact. With the bottom halves of each breast covered in a sheer black adorned with floral patterns, it felt like Annabelle had premeditated this somehow. There was no way someone would come into the office every day wearing lingerie like this.

Annabelle brought her arms underneath her breasts and pushed them up, emphasizing them even more. “You like?” She asked. I couldn’t do anything but nod ferociously.

She pushed her chest forward, emphasizing her breasts even more. “You can play with them if you wan–oh!”

She didn’t need to finish her statement for me to take a step forward and grope her. Her breasts overflowed in each of my hands, palms scraping against the floral pattern as my fingers spread out as much as I could. I wanted to take as much of them as possible for myself. Annabelle’s smirk quivered slightly, the proud presentation she had melting slightly as a deep sigh passed from her lips. She took a step forward, sandwiching my hands between our chests, and ran her hands up and down her sides, giving a show that was just in my peripherals.

“Mmm,” Annabelle huffed. “I’ve been waiting for someone as youthful as you to join my team.”

“Is this about the personal assistant thing?” I asked, my voice trying to be teasing, but my tone ended up more curious than anything else. Thumbs hooking into my belt loops, Annabelle pulled my hips into hers, her lips against my neck. Tilting her head upwards, I looked down, letting our gazes meet before she tried to push herself a bit more onto her toes.

“Maybe we can consider today your interview for that,” she huffed, her breath against my neck sending a surge of shocks through my back. My gasp was the last sound between the two of us before she finished closing the distance between us and turned her head, our lips once more meeting up for a hot, impassioned kiss.

I followed Annabelle’s lead in the kiss. It wasn’t that I didn’t want to have control between the two of us. Rather, this was Annabelle’s court; she was the boss between us, and this was a so-called interview. I had to gauge things accordingly, and take control at the last moment if I wanted to put her in her place. Even if she were my boss, and two decades my senior, I wasn’t going to let that get in the way of my urges.

As Annabelle slipped her tongue into my mouth, I returned the favor, my tongue eagerly tangling with hers. She brought a hand to my hair, slowly running it through my locks as if she were trying to comfort me like a pet. I pushed my hips against hers in reply, declining the notion that she would be able to stay on top of everything without a fight.

Annabelle pulled her tongue away and broke the kiss, but not without sucking on my tongue first. Once she pulled away, she pushed herself into me even more, raising her left leg and wrapping it around my thigh. Her hands pressed against my shoulders, and slowly, she ground herself into me, trying her best to roll her hips against mine in circles while on one foot. I brought my hands down to her ass to help her balance.

Not long after, our lips were against one another once again, my hands eagerly massaging her ass through her pencil skirt as she ground her crotch against me. I could already feel the aching heat starting to form between her legs and radiate through her clothes. Her tongue tangled with mine once more, trying its best to distract me from her arousal, and I played along, twirling and twisting around hers while swallowing the soft moans that leaked from her.

And just to show her who exactly had the control between us, I slowly pulled a hand back and sent it across her ass, the clap echoing throughout the elevator. Annabelle broke the kiss just to let out a heated moan, and I took the opportunity to plant a series of kisses against her jawline and down her neck. I couldn’t help but feel proud of myself as with every kiss I heard the wanton cries of my boss, the dynamic between us disintegrating right before our very eyes.

It was so hard for this to be wrong if it felt so good. I looked over my shoulder for a second, peering at her left hand; a distinct lack of a ring on her fourth finger was equal parts relieving and confusing. I turned back to face her, her expression flushed and panting as her grinding grew more heated. Even with my hands on her ass, I could feel her balance starting to give way, and before long, she pulled back, standing back on her two feet.

“Man, I’m really not what I used to be years ago…” she mumbled to herself. Her legs quivered slightly as she regained her balance, and after a few moments, she stepped backwards, the weight of her body against mine finally relieved.

It was only at that point when I saw my erection pushed up against my pants, aching to be freed from its constraints as angrily as it was. I knew that I was aroused, but for Annabelle to have me like this made me glad I wasn’t as vocal as she was.

Once Annabelle had taken a few deep breaths and regained her balance completely, she snapped her fingers, immediately returning my attention to her completely. She resumed the swaying of her hips. In her hypnotic dance, she ran her hands up and down her body, pushing her elbows into the air as high as she could. Her hands drew circles along her torso, patterns as elaborate as the flowers on her lace. She descended down her smooth belly, and down to her hips, where her pencil skirt hung on her body.

She teased the garment’s waistband for a few moments, as if deciding what she wanted to do with it, before coursing her fingers down the fabric of it. Instead, she leaned forward slightly, her fingertips gripping the bottom of her skirt. From there, she grabbed her skirt and slowly hiked it upwards, exposing the garter straps that kept her leggings so high on her legs. She pushed her skirt up her legs, until she exposed the bottom of her panties, showcasing more floral black lace, and the top of her skirt was up against her waist, covering her navel.

The scent of Annabelle filled the air, and with one hand hiking her skirt up, the other hand slipped between her legs and started rubbing circles against her panties, right where her pussy was. She stood up, making sure any attention I had on her cleavage was now on the hand rubbing herself, and bit her lower lip to hide her moans. Her knuckles trembled as she gripped harder on her skirt, and she pressed herself up against the wall, giving herself much-needed balance as she gave her show.

As she let out a low mewl, our gazes met once more, her eyes dark with lust. She pulled her fingers away from her panties, momentarily, to beckon me closer with them, and once I took a step forward, they returned to her crotch, rubbing in slow, deep circles.

Once the distance was closed, I slapped her hand away from her crotch and replaced it with my own, running my fingers in circles around where she was rubbing. With a rough huff, Annabelle grabbed me by the belt and pulled me in, her lips hungrily pressing up against mine in a hungry kiss. As our tongues tangled, I pulled my hand away from her crotch and gave her a soft swat. She gasped and pushed her hips down against my hand, slowly rolling herself in circles while I toggled with her sex.

Through the lace I could feel all the heat pooling in her pussy, and as my fingers pulled away so I could rub up and down her lips, I saw a slight dark spot, glistening with her juices, on her panties.

“Fuck,” Annabelle huffed against my lips. One of her hands grabbed my wrist to bring it to one of her breasts, as if demanding me to fondle her, and the other let go of her skirt so she could take a hold of the bulge in my pants. I groaned against her lips as she stroked me through the fabric, eagerly gauging my size and shape. Annabelle smirked once more, as if letting me know that I didn’t have as much of an upper hand on her as I had thought.

In retaliation, I started squeezing her hefty breast, loving its weight and how her breath hitched as I toyed with her. Even if I didn’t have it as much as I thought I did, I still held the upper hand on her, and I wanted her to know that. Especially if it meant playing with her tits, I was going to have the upper hand on her.

And Annabelle made that easier as she pulled her hand away from my pants and slipped both of them behind her back. With her elbows high in the sky, she squeezed and relaxed her shoulders a few times before bringing her hands to her sides. As she shrugged, her bra fell off her heavy chest and fell to the floor. I pulled back from her lips to marvel at her breasts. Large and heavy, her maturity had let her breasts age well, their size further accentuated by her large, pale-pink nipples. Resting one of them against my palm, I gauged her breast and how it felt, as soft and delicate as it could possibly be, and gave it a squeeze, loving the feeling of it overflowing between my fingers.

I leaned forward to press my lips against hers, but she had ducked, leaving me to kiss the air. Looking down, I saw her face pressed up against my chest, her hands eagerly running up and down the buttons that kept my shirt together. And much like how she teased each button on her own shirt, she would slowly undo them, one by one, and pull my shirt apart to expose more of my bare torso.

“Mmm,” hummed Annabelle. “You should tell me what gym you go to sometime.”

I flushed slightly as I heard those words, my silence only breaking as I felt warm lips pressed up against my pecs. Her kisses were wet, and, as I looked down, each of them were marked by that familiar red lacquer that covered her lips. She never nipped; the most she did in her kisses was suck, leaving slight pink marks coated with her saliva.

The more buttons she undid, the more skin she exposed, and the more skin she covered with her lips. My body twitched as she descended, not only from the stimulation of her lips against my torso, but also as her soft breasts pressed up against my thighs, nipples grazing distinct paths against my legs. My toes curled in my shoes, the erection raging in my slacks straining the cloth to its limits.

As Annabelle undid the last few buttons, exposing my abdomen to her, she leaned forward, letting her breasts press up against my groin, suffocating my clothed cock in her warm softness. I could feel each breath of hers, her chest rising and falling against me in a slow, almost-calculated manner. Her lips tickled my abs, ensuring to mark each one with its own discrete mark. And then she looked up at me, her lips pouted as if she had just been pulled away from a kiss, and immediately, the pout turned into a devious smile as she pushed herself into me even more, slowly rocking her torso up and down to grind her breasts against my cock.

I groaned and threw my head back as she toyed with me, even if there were the few layers of clothing that separated us. Even though I couldn’t see her face, I knew that she was smiling even wider. Even while she was on her knees, after worshipping my body, she had the upper hand on me. The suffocation was impossible to resist, and she could feel every throb of my cock as I struggled not to explode right then and there.

Once I finally found a rhythm of breathing to keep me from cumming early, Annabelle pulled back. “My, you’re a patient one,” she cooed as her hands found my belt buckle. Undoing it with the haste of a salesperson late to their job, my belt fell to the floor, and immediately after my pants and boxers alike followed suit.

Annabelle’s eyes widened as my cock flopped out from my boxers, smacking her with a gentle downward blow. The dollop of precum on my tip smeared across her cheek, which she was quick to collect with her finger and clean up with her lips. She saw the veins at my base pulsing, and she wrapped her hand around them, giving my cock a slight squeeze. Her lips parted; my cock didn’t give at all to her squeezes.

“You’re so hard…” She tried to make herself sound innocent, but her voice was dripping with lust the way I expected her pussy to be dripping with juices. Not that I could see, though; she was too busy admiring the sight of my shaft for me to even think that much about anything else.

And once she pressed her lips against my tip, I couldn’t think about anything else. The softness I felt against me with every kiss translated perfectly into her welcoming my cock in her mouth. Her lips parted as she pushed herself forward, eagerly swallowing me whole and forcing her jaw wide open to ensure that not a bit of tooth scratched me.

I grabbed the back of Annabelle’s head, making sure she familiarized herself with the way my cock felt in her mouth. She replied with a low moan, sending shivers from my tip to base and up my spine. I grabbed harder, taking the best handful of her hair that I could, but even then, my hand was following the motions of her head as she established her own rhythm, the sounds of her slurping up my cock and gagging as my tip hit the back of her throat filling the space around us.

It was beyond intoxicating. My entire lower body quivered as she pushed and pulled herself, loving both the vice-like grip of her mouth as she gagged against my cock to the way she eagerly and dutifully sucked on my tip. The parts of me that she didn’t push in her mouth were treated by her hands; one of them eagerly circulated around the base of my cock, and the other massaged by balls with the same fervor. I wondered if she was able to feel the tightening in my balls the same way I could, a cloud of white starting to fill my vision as I found myself succumbing to my desires.

And before I knew it, I was the one in charge. With a gagged yelp, I pushed my hips forward, feeling the warmth of her mouth transition into the tight sliminess of her throat. I groaned at the newfound pleasure of Annabelle deep-throating me, and I pushed her further, until my balls pressed up against her chin. I looked down at her gaze, tear-stained and amorous, and held her there until she tapped against my leg, beckoning for air.

Even as she gasped for breath, she smiled. Looking down and seeing the faint red rings that had formed midway around my cock, and the thicker ring that was pressed up against my hilt, I couldn’t blame her for smiling. However, while I smiled because of the utter delight of how her mouth felt, her smile was wild and lost, lust having taken over every one of her senses. The stroking of her hand along my cock was rhythmic but at the same time an afterthought. It was like something had changed in her mind entirely, and any thoughts she had about the job were now about being fucked nastily in this elevator, to treat her not with the respect of a co-worker or an older woman, but with the absolute nastiness that service can possibly provide.

And much like her inhibitions, my trepidations had melted away. So what if she were my boss? “Good girl.” The words felt weird coming from my mouth; calling Annabelle, someone nearly twice my age, a girl. Annabelle cooed nonetheless, and with one hand grabbing my cock, she brought the other to my hip, giving herself the leverage she needed to stand up.

Once she got onto her feet, she stumbled forward and pressed her lips against mine. I could feel the sloven hunger radiating from her lips, hungrily meshing and leading the way in our kiss. I pulled slightly on her hair, letting the groan that came out rub up against my lips, and my other hand reached around to grab her behind, the skirt being hiked up just enough for me to evade its clutches. I paused momentarily as I gave her a squeeze, her ass feeling just as heavenly in my hand as her breast did, the same softness and weight that gave her body such a mature feel swallowing my fingers as I dug them in.

“Fuck,” Annabelle huffed before leaning forward and pressing her hips against mine. With only the lace fabric separating us, I could feel the hunger between her legs, wetness dripping down her inner thighs and smothering my dick with every roll of her hips. I bit down on her lower lip and pulled back, pushing my hips up against hers, and listened to her mewl in pleasure. I kept pushing my hips upward, my cock rubbing up against the lace that covered her pussy.

“What do you want?” I asked, letting go of her lip. I basked in how shallow Annabelle’s breaths were, as if she were realizing that the advantage that she so wished for was still outside of her grasp, and that she would have to beg to get what she wanted from me.

Annabelle took a deep breath and brought a hand between us, slowly slithering down my abs. “I want this big, fat cock,” she huffed, taking hold of my dick, “deep inside my tight, wet cunt.” As she spoke, she stroked me, up until that very last word, where she pulled herself away and brought her hand to her panties. Slowly, she slipped her hand up her skirt, and once it came down, so did the waistband of her underwear. The rest of her panties followed, the thong quickly falling to the ground once she let go of it. The wet splat that filled the elevator made my cock throb; I was ready to fill her up. Bringing a hand to my cock and pressing it up against her shaved sex, she, too, was ready to be filled. Annabelle lifted one of her legs and wrapped it around my lower back, making sure I could slip into her without a problem.

And with one thrust of my hips, I pushed my cock into my boss’ waiting pussy.

I watched with delight as she bit down on her lip as I plunged into her, trying her best to hold in her moans. If it felt as good for her as it did for me, I understood her struggle. Her walls were so wet and accommodating; I didn’t even realize that I was all the way inside of her until my hips pressed against hers. I silently cursed myself, wishing that I could push myself into her forever.

“Fuck,” she groaned, “you’re so big inside me. I’m not sure I’ve had anyone this big before…”

“God,” I huffed right back. “Maybe it’s just because you’re so tight.” Slowly, but surely, I pulled my hips back, readying myself for another push inside of her. Once I had only my tip inside of her, I pushed into her, and she reached back, grabbing the railing behind her for stability.

The first few pushes I gave were slow, exploratory; I wanted to know every bit of her that I could feel. I wanted to feel her as her pussy spread, accommodating every inch she possibly could. I pushed in different angles, trying to find the sweetest spots inside of her, and I listened to how her breathing hitched and how loud her moans were with every push and pull I made. As I grew more familiar with her, and the feeling of her pussy grew more intoxicating, I sped up, making sure to give each thrust the same amount of depth and roughness as I had at first.

As we fucked, Annabelle leaned in, pressing her chest against mine and her lips against my shoulders. She planted a string of kisses down my collar, nibbling slightly at my skin. As she pulled away, I could feel the moans that wished to come from her lips that she suppressed. Each kiss grew deeper and lingered for longer, slowly pushing herself into a space in my neck where she could moan with impunity, and without me seeing her.

With her supporting herself, I pulled a hand away from her ass and I gave her a harsh swat. She pushed her hips back into my hand, trying to please both my gropes and my cock. Giving her a second spank, she pulled away from my neck and let out a long, low moan. Her pussy squeezed my cock, and I moved faster, making sure to take a handful of her hair so she kept her head back.

As she leaned forward once more, I yanked on her hair. The gasped groan from her lips was intoxicating, as was the way her entire body quivered. I looked into her eyes, and she looked into mine. No words needed to be exchanged; rather, we just stared, my growing smirk matching the libidinous grin that was forming on her face. Her lips parted, only to quiver and let out another delicious moan. I leaned in and pressed my own against hers, muting her and letting myself continue to have my way with her.

As we made out, I slipped my tongue into her mouth, tangling it with hers, exchanging moans with one another as our bodies burned and jostled against one another. My hips kept pistoning, feeling the wet vice of my boss holding me tighter and tighter, squeezing with ever-deepening ferocity until she pulled a hand away from the railing and between her legs, immediately finding purchase on her clit.

The sounds of her pussy squelching grew louder as she started toggling her clit, rolling her fingers in small circles around the nub, and her moans grew harsher. What were once pleasured mewls felt like they were being ripped from her throat. I could feel her growing heavier in my hand, the one leg holding her upright wobbly from supporting herself. I stepped forward, pushing her into the wall, and started thrusting even rougher, making sure to pin her between myself and the elevator.

She let go of the railing and wrapped her arm around me before pulling her lips away from mine. “Fuck, I’m gonna cum…”

As I heard those words, I slowed down, the rampant jackhammering that I was doing now deliberate, rough thrusts sinking myself into her so quickly that I could feel my balls swinging against her taint, or pulling out so quickly I was surprised I had the discipline to keep my tip inside her. Each was punctuated by stillness, bar the rampaging rolling of her hips and her body quivering. Annabelle’s breathing grew uneven, and as I tried to push myself into her, her pussy rejected me wholesale, keeping me out and drenching me with a coat of her cum as she let out her loudest moan thus far.

Even though I pulled away, she still rubbed her clit, although her hand was moving back and forth in a very uncoordinated manner; whether she was touching it or not I couldn’t see from there. What I could see, though, was a network of juices connecting my cock to her lips, strands of which broke as I pulled away from her to observe the spectacle of my boss post-orgasm.

It was like looking into a mirror dimension. At the beginning of the day she looked so well-mannered, so mature, so involved in her work and professional; she actually looked like she could have been my boss. And now, there she was, panting, her body all pink and covered in a thick layer of sweat like she had just ran a marathon. A trail of spit was between her breasts, a leftover from her sucking on my cock, and even then drool leaked from the corner of her lip as she plunged two fingers into herself, giving me not just a show but a sign that she was ready for another round whenever I was ready.

And I plunged right in. I was going to take advantage of this situation in every way I could.

The way that she felt around me the second time around made me shiver, the unspeakable warmth and tightness of her cunt milking me senseless causing me to groan. I grabbed onto her shoulders and she pulled her fingers out, yielding them to my hips’ slavish jackhammering. I was so focused on the way she felt around me, the telltale throbs of a woman in heat wanting more, that I hadn’t even realized the fingers in front of me until the scent hit my nostrils. I gave her fingers a lick, collecting the taste off of them.

My head fogged up even more with lust. She tasted delicious and needy, like the musk of Aphrodite herself had landed upon my tongue. Collecting the ambrosia from her fingers, I licked them clean and pressed myself into her, letting herself have a taste with a tongue-kiss. Her hands grabbed my shoulders and squeezed, eagerly swirling her tongue around mine as I kept pounding her.

I pulled away from the kiss and looked aside, at the mirror and at our reflection. I watched as my sweat-covered, messily-dressed self slammed my own hips into my boss’ quivering body, and the way her curves jiggled with every impact. From the way she cried out and moaned, it provided the perfect soundtrack to this quasi-porno I watched. Only being caught in her warmth reminded me that this was truly happening, and I looked away, wanting to take it in for myself once more that this wasn’t like any pornography. This was a real thing happening, and I needed to enjoy every moment of it.

“Fuck! Fuck! You make me feel like a real woman!”

Annabelle’s cries rang out through the elevator, and the grip that she had on the railing behind her, despite her best squeezes, grew weaker. With every thrust I could feel her growing less balanced, and before I knew it, she slipped, my cock removed from her with a quiet popping sound moments before she hit the ground. Her legs quivered violently as she laid down on the carpeted floor, her hips wiggling as she whined needily.

“Ms. Fletcher!” I don’t know what led me to call her that at that moment, but I knew lust wasn’t what I was feeling. I felt, instead, concern. I squatted down. “Are you okay?”

She nodded. “I’m fine.” Slowly, as she spoke, she spread her legs, exposing her flushed, wet core to me, and brought a hand to her sex, not to hide it, but to finger herself. “Now come here and give yourself what you want.” As if to make her case clearer, she wiggled herself slightly and brought her other hand to her breast, giving it a rough squeeze.

Slinking between her legs, I rested my hips against hers, letting my cock rub up against her swollen, sodden folds. With a thrust up and down, she let out a mewl and removed her fingers, instead deciding to run them along the underside of my cock before wrapping them around my shaft wholesale. I kept stroking, watching her fingers run up and down as she slowly adjusted the angle until my tip pressed up against her entrance, and I slipped into her once more. I brought my right hand to her left shoulder and my right hand to her breast, and as I sunk into her, I gave her tit a squeeze, relishing in its softness as I filled her up once more.

As I gave a few exploratory thrusts in the new position, I looked at Annabelle, her eyes rolled into the back of her head and her teeth squeezing at her lower lip, trying to block me from hearing the moan that leaked from her lips anyways. The more I gave, the more she looked like she was trying to hold everything in, bar the hand which now rested on her clit, which she rubbed messily. I kept going, watching as her body quivered and she tried her hardest not to let me hear what was on her mind; I didn’t need to, given how I could feel her lust as she squeezed my cock tightly.

Once I finally stopped teasing her and started using gravity, it didn’t take long for her dam to break.

Pushing my hips down into her, I could feel how much I was using my body weight to fuck her, each impact pinning her between my body and the floor. Her cries were louder the moment she let go of her lip, her breathing hitching with almost every slap of my hips against her thighs. I found a rhythm, one slightly slower than the one I used when we were standing up, and committed to it, the push and pull of my hips followed with a slight up and down of her own, trying to keep me inside her as long as possible.

“Oh, fuck! Fill me up…”

I followed her cry, picking up the pace just a bit and making sure that I fit every bit of myself into her. Her thighs flexed and I could feel her legs wrapping around my body, making sure I couldn’t leave her now that she was like this. Not that I wanted to leave the warm heaven that surrounded me, her squeezing sex leaving me throbbing deep inside of her. I could feel the first rush of bliss starting to course through me, my balls tightening as I kept thrusting deep, and I knew she could feel it against her taint.

“Fuck, Annabelle, I’m gonna–”

“Are you gonna cum?” Annabelle asked, putting heavy emphasis on that last word. “Do it, give me your cum… Cum in me…”

The more she begged for it, the more I could feel myself going into overdrive. I could feel the coordination in my thrusts giving out in lieu of rougher, quicker thrusts deep inside of her, which was greeted to a celebrational few cries as her body quivered dangerously around me. The way she milked me didn’t help in keeping my orgasm at bay. I was growing white hot, and as her legs tightened around me, I knew that I wasn’t going to have a chance to do anything else but breed her.

“Don’t worry,” she reassured, “I’m on the pill, and nobody will have to know.”

That calmed me down a bit; I didn’t know what would happen to me if this little affair that I didn’t even know would happen when I started work would end up with me having to take responsibility for a child. Maybe in a few years, once I climbed up the ranks of the company and had the seniority and the maturity, but not as a greenhorn.

And yet, there was something so alluring about the thought of spilling my cum so irresponsibly into this woman twice my age, my boss, the person whom half the company looked up to as inspirational. There wasn’t any way that I could describe it outside of naughty and a fantasy, and there I was, living up the kind of life I didn’t even know I wanted.

My cock throbbed violently and I could feel the cum rushing through my balls and out my tip. I bottomed out and let her feel the waves of spunk that left my throbbing member, the low moan she let out one of pleasure as her walls were coated in a good coating of my cum. Her walls kept squeezing me, as if wanting to milk out every last drop my balls could give her. I provided; it felt like it took minutes for my orgasm to finally subside, and as it did, I slowly pulled myself out of her, cock limp from overstimulation.

Annabelle looked down at me with a smile and brought a hand to her folds, clearly not quite done with me. She let out an overly-pleased hum, though, as she ran her fingers along her now-fucked sex. “I can feel how thick it is inside me…”

Just for show, she slipped a finger inside herself and scooped a slight bit of it out of herself. I watched as the white rivulet dribbled down her fingertip as she brought it to her mouth. I could already feel myself starting to harden as she wrapped the digit around her lips and started sucking on it. When she pulled away and stuck out her tongue to show she swallowed it, I was already at half-mast.

“God, you fucking minx…”

“You shouldn’t be talking about your boss like that…” Annabelle teased, “but you can talk about your bitch like that.”

“My bitch?” I asked, incredulously. Surely, there was dirty talk, but between the moments of heat, it felt weird to hear her say that. Maybe it was just because of how horny she was, but for me, post-nut clarity was starting to hit. My hearing was clouding up just a bit, and I couldn’t help but think that I misheard her there.