The First Day (is the Hardest)

"Are you kidding? Breeding me and stretching my poor pussy open like that and you don't think I'm your bitch?" Annabelle teased, bringing her fingers to her pussy to stroke herself just a bit more. Meanwhile, her other hand wrapped around my cock, slowly stroking it as if I hadn't just came. I winced at first as the pleasure coursed through my body, but the more she stroked, the more used to it I became, until it didn't even feel like a novelty.

Fueled by that sense of vigor, I wanted to stick myself between her legs and start pounding her senseless, but before I could even get to my knees, she shifted her position, resting her head between my thighs and lying on her side just conveniently enough for her sex to be pressed up against my hand, her legs slightly parted so my hand could be accommodated. She opened her mouth and wrapped her lips around my cock, moaning at the flavor.

It took everything in me not to scream out in bliss right then and there, the softness of her lips compounding dangerously with how overstimulated I was, and I diverted my attention to my hand, slipping three fingers into her pussy and thrusting them as roughly as I could. I sure as hell wasn't going to be the first one to cum twice today.

Her toes curled as she sucked me off, moaning loudly the more that I fingered her. My other hand rested in her hair, monitoring the way she bobbed her head up and down on the top half of my cock. With every exchange of gazes, I could feel myself wanting to thrust harder into her and ruin her, my middle finger already grazing all over her g-spot like it was a trophy I was polishing. Her bobs grew faster and deeper, the occasional gluk sound coming from her throat as she grazed the back of her mouth, and I fingered her even harder. It was a feedback loop of lust.

The feedback loop went off the rails once I rested my thumb against her clit and started provoking it, too. Annabelle bottomed herself out, resting my tip against the back of her mouth as she cried out in bliss, her legs quivering madly as she rode my fingers, trying to savor all the pleasure that coursed through her.

Seeing her like that, I couldn't help but add to the provocation. "You like that, huh? Like slurping up my cock while getting finger fucked, you bitch?"

I couldn't tell you how weird it was putting conviction into calling my boss a bitch, but she looked up with tear-stained eyes and nodded to the best of her ability before pulling away.

"I love it, sir. I love how--fuck--your fingers feel as I'm sucking your co--oh, fuck!--cock! Please, fuck, more!!"

And more I gave. I continued thrusting my fingers even as my hand started cramping up. Her pussy squeezed tightly around my fingers, clasping around them with somewhat of a disregard for them. She humped my hand, but she might as well have been humping the air. Her eyes rolled into the back of her head, and eventually, I could feel her trying to push my fingers out of her. I did, only to bring them to her mouth to taste herself along with whatever collection of my creampie I had as a small torrent of juices leaked from her hole, clear with a discrete stream of white going through it. I pulled out my cock and slipped my fingers in, feeling no change in how she suckled and licked them.

"God, that's so fucking hot," I huffed to myself.

"Mmmph," whimpered Annabelle, bringing her hand between her legs to give herself a second taste. She swirled her fingers around her sex, scooping up as much of her juices as she possibly could, and brought them to her lips. I pulled my hand away, letting her slip her fingers inside.

There was something about the way that her eyelashes fluttered when she looked at me, sucking her fingers off of our combined juices, but it was enough for me to slip behind her legs, hips first, and press my cock against her sex, as if to plug the stream that had leaked out of her. She was begging for this, and I wasn't going to deprive her of her desires.

However, before I could push myself in, she sat up and pushed me down to the ground, the carpet not as kind and forgiving as I thought it would be. I laid there, though, and looked down, wondering what Annabelle was thinking of while she undid her heels and threw them aside. Once they were gone, she straddled me, resting her knees against the ground, and squatted low until her lips brushed up against my cock.

I grabbed the carpet underneath me as if it would help me get my bearings, the softness of her sex incredible against my cock, and the hypnotizing sway of her hips as she danced around it while being so close was equally intoxicating. She swayed herself back and forth, rubbing her wet sex against my cock, smearing it with her and my cum alike. She let out a soft moan as she danced, one of her hands pinning my shoulder to the ground while the other one ran up and down her body.

"I'll take care of this one. You've been so good to me," she spoke, her words so syrupy sweet. Meanwhile, she pushed her elbow up to the air and grabbed her breast, tilting her head slightly as if she was going to lick her arm. I couldn't tell you why it was so sexy watching her do that, but something about it made my cock throb. As the show progressed, and she kept running her hand up and down her side, I brought my hand to my cock, finding my base and pointing it upward.

She got the cue, and she lifted her hips up just enough for me to point it upward, and then she sat down, putting her entire body weight on my cock.

It felt phenomenal having her on top like this, her warmth pressed up against me in such a novel way. It felt much more suffocating like this, with her hips pressed against mine instead of the other way around. I let out a groan, trying my best to hold everything in as my cock pulsed inside of her crazily.

I didn't even notice how her fingers were grabbing her breast, squeezing it and letting the flesh seep through her fingers, nor did I notice how she bit her lip trying to hide her own lust from me. Not that it mattered; this was going to be her third orgasm of the day.

It wouldn't be, though, if I couldn't manage the way she started dancing on top of me. Between slow rolls of her hips and the way she gyrated and stirred my cock around inside her, I couldn't help but throw my head back to the ceiling. I wanted to keep my gaze on her, though, and watch as she danced and swiveled herself around on top of me. I knew it was a sight just as hot as it felt with her pussy around me like this. But I couldn't; I was too caught up in the throes of my lust, coursing dangerously hot through my body like sparks through bad wiring.

I couldn't see how she felt, but I certainly could feel it, the way her pussy squeezed against me with every pull back and how she ground her clit against my crotch as she bottomed out inside of me. Her thighs quivered dangerously around me, but it didn't stop her from lifting and dropping herself on top of me. Her breaths were ragged pants dotted with long, lusty moans, but she didn't stop. The pleasure was just too much for her.

"Fuck, Annabelle!" I groaned. My cock pulsed deep within her confines, and my toes curled as she picked up the pace.

I finally was able to find the energy to look down and observe her dancing on top of me, and I felt myself growing harder if it were even possible. She focused both her hands on running up and down her sweat-coated body, fingers eagerly tracing the soft suppleness of her mature curves. Her tongue ran barely across her lower lip, as if soothing the teeth marks from the many times she bit herself. Her gaze was dark and lusty, her face the same shade of pink as her pussy, and her glasses were slightly fogged from her exertion.

However, most of my concentration was on her body, the way she swiveled and thrust herself, the way she quivered when she was as high as she wanted to go, as if her body was spent of all its energy. It was impossible for me not to adore the sight as much as I did, hungry to see more of it. I let go of the carpet and reached forward, letting my hands join in on fueling the fire inside her.

I spanked her. I spanked her hard, feeling it in my hand, and she yelled out before picking the pace up just a bit. I gave her another, and I could feel her rhythm grow just a bit uneven. The more I spanked, the more uneven she became, until, eventually, I could feel the telltale vice-like squeezes warning me that I needed to pull out of her now.

And when I did, my lower thighs were treated to a literal shower of her cum as she squirted all over me.

Her thighs were tense as she sprayed me, her entire body bar the bend in her knees completely upright as pleasure coursed through her. She said nothing; she didn't even moan. There was nothing in her face but pure lust, coursing through her and relieving herself through her pussy and onto my body. It was a sight to behold, and as the drenching of my cock from her squirting came to a close, she fell limp on top of me, taking deep, heavy breaths as she recovered from the strongest orgasm of the day.

"Fuck..." Annabelle huffed, looking down at the mess she made, either unaware or uncaring that she was staining her skirt in sex. "That felt so fucking good..."

"I bet," I replied, running my hands along the curves of her body, giving myself a moment to explore the woman whom I fucked, and the one I'd call my boss tomorrow, and maybe my bitch tomorrow as well.

"It's not often that I do that, at all," she added before letting out a slight giggle, her fingers reaching down to take a hold of my crotch. "I think I need to give you something extra special for you to remember this moment."

"What do you mean?" I asked, but before I could finish my question, she was slowly slinking down my body, not caring that the pool of juices between us was smearing her clothes. It wasn't like there was anyone who could see any of this. We might as well have been the only two people in the building given how long we were in there.

And given how Annabelle was between my legs, her heavy bosom pressed up against my thighs, we knew that neither of us would have preferred it any other way, especially as she slowly moved herself up and let her breasts wrap around my cock.

As she rocked her body up and down, I let out a low moan, trying to hold my composure as I throbbed between her breasts. She brought herself up as much as she could, sticking her tongue out to add a bit more lubrication by spitting on my cocktip as she rubbed it between her breasts, smothering me in her impossible softness. It was impossible for me to think with how she was treating me. It felt softer than her mouth, softer than her pussy, and as her hands squeezed them together, tighter than both.

It didn't take that long for her to pick up a pace, and suddenly I understood exactly how she had felt throughout the entire fucking. Perhaps she would never feel how it was to be able to do it to a boss, but I understood the other aspects of it, how it felt being treated so well and having a moment to relax as all the tension from the day pent up in my body, drawn out by her pebbly nipples rubbing up and down my shaft with every rock of her torso. She was driving me mad, madder than she had throughout the day, and for her actions I gave her a small spurt of precum.

She let go of my breasts to run her fingers along the stain on her neck, and brought it to her lips, humming delightfully at the taste. And once she brought her hand back to her breast, she tipped her head down and opened her mouth, taking as much of my cocktip as she could while massaging my shaft with her tits.

My hips started moving on their own, rocking more of my cock into her waiting, moaning maw while enjoying the warmth of her breasts. Sparks coursed through me like mad, the hums less heard and more felt as they stimulated me and brought me to another level of pleasure. I wasn't able to handle it for very long, but I rode it out the best I could, just so I could see the sight of her taking my cock in such a lewd manner.

When she felt my lower body throb, she pulled away, letting me coat her lower face and neck with a load that shot out of me. I was surprised; some of the cum from the first shots managed to pass her head and get into her hair, but most of it, especially as things settled down, landed on her chin and neck. She recoiled at first, especially as her upper face got a slight coating, but as things cleared up, she looked down with amusement, loving every spurt I gave until the final one lamely dribbled out from my tip and into her cleavage.

I pulled out and watched as Annabelle cleaned herself up the best she could, taking the cum off her body with her fingers and scooping it into her mouth. With every scoop, she let out a low moan, either to appreciate the taste or to tease out a third round. My cock stayed limp, as much as I didn't want it to; she had, for the time being, drained me, and my cock wasn't wanting any more stimulation. It was unfortunate, but it was something that I had to deal with.

Once she cleaned herself off, she looked at me with a warm smile, but not before lecherously scanning my body like it was some sort of trophy. "You said that this was your first day here?"

"Mhm," I said, nodding. "I just started today. Why do you ask?"

She crawled around, collecting her garments that were all over the place with a distinct wiggle in her hips. Whenever she got around me, she emphasized it, but not without getting a spank which she teasingly rubbed and pouted about.

"Well, I'm glad to know that you're more than qualified for the position."

"Is that because of, well..." I asked before gesturing around the place, particularly pointing at the mirror so she could take a good look at the damage that we've done to not only each other, but the carpet and the elevator itself.

After a few seconds, she laughed. "Of course not. This wasn't part of the job, but all those spreadsheets you did today? That was a lot of work for someone new to our company. I'm sure you'll be rising through the ranks in no time." As she spoke, she kicked her legs out and slipped on her panties. However, before putting them on, she gave herself a quick rub.

"That said, this might go on your record if you ever want to be my assistant."

Even if it were an open office, it would be interesting to see what that would entail, but I kept my mind off of it. "I should see how I fit with the rest of the company first," I said. "Maybe someday I'll be your assistant, though."

"I hope you are," she said as she slipped on her bra and shirt and did her buttons up. Her body was a mess, and her clothes were stained, but outside of that, she looked fine. I still couldn't help but look with a bit of concern.

"Don't worry," she said. "I have a change of clothes in my car, so I'll be fine going home. Plus, you should probably get dressed so I can get the elevator running again."

"It wasn't broken?" I asked, a bit incredulous as I picked up my clothes and sloppily put them on. There were stains, but it wasn't anything like Ms. Fletcher, who thought to wear her clothes during the sex.

"Nope." She said, "I just saw that you were alone and wanted to get to know you better."

"You could have done that over coffee."

"I saw the way you were looking at me at work. I thought this might be more fun," she laughed. Giving me a once-over, she turned around and got the elevator running once again, moving downward until it hit the first floor.

And then we stepped out, said our goodbyes, and parted for the night like nothing had happened.

On the drive home, I did wonder about what poor janitor would have to clean that elevator up, though.