The First Day (is the Hardest)

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.