The First Day (is the Hardest)

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.