Toying with The Boss

by Carley Rose

  One hand found a handle, the other soon joining it with white knuckles as the dildo continued to thrust without pause, the relentless pace making me wonder if Jack didn't bother with different levels for this toy.

  It was just so much, the large dildo fucking me at an unhuman speed unheeded, the machinery used undoubtedly one of the strongest Jack had created to date.

  Tears stung my eyes as my chest heaved, legs too weak to do more than take it, sitting on the rocking chair as Jack's dick double kept going. It was more than the machine from this morning, although whether it was because of a combination of all the other fucking I've done today or the wine in my system, I couldn't tell.

  I cried out when I came, my nerves on fire but the machine kept on thrusting. Looking at my hands, I realized I didn't have the remote. My overly sensitive clit continued to take the beating Jack's toy was giving it as I tried to find the remote, blinking away tears to clear my vision as my gaze hurried over the ground around me. It must've fallen out of my grasp when the vigorous nature of the toy surprised me. There was a good reason I didn't drink before testing products out.

  I could barely even feel stupid as the machine continued to fuck any thoughts out of me, whatever mechanics powering a force to be reckoned with to be going for so long with only battery power.

  My gaze caught sight of the remote and I leapt at it, as much as my current position allowed. The chair swung, bringing the dildo and my hips with it as my body bent and curved around the dildo. I saw stars for a moment, a line of drool falling from my lips as the toy stretched right up against my swollen clit before remembering to hit the button.

  I nearly sank to the ground in relief when the dildo stopped, turning off at the single push of the button.

  Getting myself off the damn thing was even harder, my legs uncooperative and unhelpful as I mostly succeeded in pushing myself up, falling back down on it, and making the chair swing so every time I did get off a bit the chair would just fuck it right back into me.

  I came once more before finally sliding off the large dildo, my vagina sore and done for today. Perhaps for the next few days. Looking over the mess, I decided tomorrow was a better time to clean up and simply dragged myself away from the swinging chair, forgetting the shower as I collapsed on to the couch.

  The simple comfort was enough to ease some of the ache between my legs, my body sinking into the plushness of the cushions as my mind drifted off, ready to be done with the day.

  In the tired state of my mind, thoughts wondered as I felt sleep slowly creep in.

  Jake.

  This was all his fault.

  He had to get upset at me, but for what? I didn't do anything except my job. He couldn't even stand to look at me. When we first started out, we could talk and make jokes for hours while working on the business details together. A lot of times even after finishing up with business for the day.

  When did things start to get distant between us? It had to be recently. Was it the fact we were getting more orders in? Jake was locking himself away in the basement more often, forgoing our nightly chats in lue of working. Working on orders? I doubt that. He finished in time but not a moment before then. The toys, then?

  But for what? My eyebrow twitched in annoyance, trying to remember the last time Jake had even cracked a joke around me. It felt so long ago.

  I missed him. I missed what we had. It was like a part of me had left, filling up with cold emptiness whenever Jake acted indifferent or excused himself before we could actually talk.

  My eyes shot open, staring at the back of the couch as realization dawned on me.

  I liked Jake.

  Fuck.

  +++

  End of Toys ‘in Us

  DIY: Toys Required

  "The batteries need more work, but I think it might be one of our bestsellers if you can get it to last longer."

  Jake, as usual, was sitting at his work desk, looking over the toys I tested last night. There were dark rings under his eyes as he blinked wearily at the vibrating dildos. Despite sleeping on the couch last night, I hadn't heard him walk upstairs to the guest bedroom he usually slept in when he spent the night.

  It was obvious he spent the night down in the workshop last night, but I kept my nagging back, still trying to process the feelings I realized last night while maintaining a professional persona with Jake. There was still work to be done, after all.

  "Huh?" Jake looked over the rocket that was similar to his original toy rocket. "How'd this get in here?"

  I raised an eyebrow. "You didn't put it in?"

  "Well, I guess I must've, but it wasn't ready..." Jake looked at the dildo in the box, but didn't pick it up for inspection like the others. "Did you test this one out, too?"

  "Uh, of course," I replied, blinking when Jake rolled his chair back towards his desk so he was facing away from me. "It was one of my favorites, actually. Reminded me of that toy rocket you made."

  Jake remained quiet, setting the box on the work table before sitting back and running his hands over his face.

  "I don't think I can work with you anymore."

  I blinked once, twice, the words taking a moment to process even though I knew I understood him properly. English might be my second language, but I started learning it as a toddler. My eye twitched.

  "Jake, that isn't something you can joke about," I said, careful to keep my voice steady despite the emotions raging inside. How can he say something so frivolous? Was it the lack of sleep? Did he know how painful it was to hear that, not just as a business partner but as a friend? And perhaps... something more?

  "I'm not joking," Jake replied, turning the chair back around before standing up, the bags under his eyes standing out even more as he finally looked up at me. "I can... I can keep making the products, but I just don't think I can work directly with you anymore. Maybe we can rent a space or hire someone else to-."

  "What the hell?!" I snapped, any maturity from my two extra years on Jake be damned. He was just being irresponsible now. "I get that you need your space, Jake, and once we can afford it you'll get it. But you can't just say things like you don't want to work with me! We started this business together, we are co-owners. We can't just ignore each other for- for no good reason!"

  My fists were shaking against my sides, staring down at Jake as I tried to control my breathing. It was slightly pleasing to see the wide-eyed look Jake had as he was obviously not expecting the outburst. Instead of coming to his senses, however, he shook his head.

  "No... We have too many creative differences, I'm glad I could help you as much as I did but maybe you should find a different partner-."

  I strode forward, yanking on the collar of his shirt so his much taller frame would bend down to meet mine before crashing my lips on his. It was a closed kiss, and more of a desperate attempt to stop him from talking more nonsense than anything, but it did the job.

  "You," I breathed out as soon as we broke apart, relishing in the clear shock on Jake's face, "I like you, as a friend, as a co-worker, and as a... romantic partner. I understand if you find these feelings unacceptable, we can work through it, but I'll be damned before I just let you walk out of the life we've both worked so hard for together without a really fucking good reason."

  I kept my eyes on his as Jake opened and closed his mouth, obviously having trouble processing what I said. It almost made me worry that I over-did it, but then the tell-tale blush and excited gleam in his eyes that took over his face calmed those fears.

  "I... I didn't realize you saw me like that," Jake said, making me life my eyebrows in surprise. I loosened my grip on his shirt, letting him stretch back up to his full height.

  "Really? I mean, I didn't really realize it myself until last night, but I thought that maybe you had noticed...?" And that’s why you were trying to get out of this company we worked so hard to build?

  "Uh, no, not at all," Jake replied, a small laugh bubbling up his throat. "Quite the opposite, really."

 
; I took a step back, looking at Jake with a questioning stare.

  "I mean, I thought, well." Jake's face was now redder than a tomato, his eyes desperate to look anywhere but me as he kept his body rooted where he was. "I... like you. And I thought you didn't see me as anything but a kid brother... and my feelings were getting in the way of work, like I was getting possessive... I didn't want anyone else to see you."

  My mouth formed a silent 'oh' as he finally confessed the reason for why he had always been so adamant against the demonstrative videos for the sex toys. Glad to figure that one out.

  "And, I mean, you obviously didn't see me like that, or at least, I thought you didn't," Jake said, his voice getting quiet until he was muttering, looking down at his shoes with his face still red.

  I gently tipped his chin back up so he was looking at me, which didn't take much since I was nearly a foot shorter than him. "It's understandable. Like I said, I didn't really realize how I felt until last night. Even if I was giving off the right signals, that still would've been confusing."

  "Ha, confusing, yeah," Jake said, his eyes flicking down to my lips before settling back on my own eyes. He was still nervous, still unsure where we stood with each other. I sighed, feeling the slight gap between our ages and experience that appeared every once in a while.

  "It doesn’t have to be," I told him, closing the distance between us again, this time less hurried. His eyes glanced down at my lips once more as I wrapped an arm around him.

  Smiling, I tilted my head up, standing on my toes as I waited for him to bridge the gap. He did.

  His mouth was soft against mine, the kiss unlike others we had shared in the past. It was sensual, but with more warmth than heat, allowing us time for our hands to drift over one another. The touches were gentle, questioning, and soft. They were nice, but after a few minutes my neck began to strain.

  "Do you want- should we-?"

  "Yeah," I replied, happily groaning as I was able to stretch out my neck. Jake took my hand, leading me over to the couch I had brought down to the basement so Jake could get a nap in when he didn't make it up the stairs to the guest bedroom.

  I laid down first, tugging him along with me. Honestly, one of the beds upstairs would be better equipped at handling two adults making out like teenagers, but I was impatient and didn't want to bother with the steps.

  His lips eagerly found mine, any reservations he had earlier gone as his larger body pinned mine down to the couch, surrounding me with his long limbs that didn't even fit on the couch.

  His hand stroked through my hair as our kisses got hotter, tongues tasting one another while more body parts started to get interested in what was going on. It felt right, better than right- it was like it had been a long time coming.

  From Jake being the pushy marketing employee to the co-owner and inventor of our business, as well as something much more to myself- it was such a change. The time spent ignoring his requests for me to look over his toys before almost felt wasted, putting off our potential future together.

  Knowing that without the slight miscalculation on my part with my old office door’s lock that none of this might've happened... It made me enjoy the current moment even more.

  My hands roamed over Jake's body, enjoying his small grunts and moans of pleasure as I found his more sensitive spots. The feeling of another living, breathing body on top of me, one of flesh and heat, was something I didn’t realize I missed so much. The fact that it was my best friend, Jake, made it all the sweeter.

  He knelt down, shifting so that one of his feet were on the ground by the couch while his knee sunk into the cushions between my legs. Taking advantage of the closer position, I bent my own knee, bringing it right up to his crotch and the heat that was starting to gather there. His breathing sped up, head falling on to my shoulder as his hips rolled desperately against my knee.

  "It's been a while for you, huh? I get off almost daily while you're just tinkering away down here," I said, wondering where all the pent-up energy was coming from.

  "N-no," Jake said, his voice wavering ever so slightly before I rubbed a hand on his back for reassurance, wondering what he meant.

  "Actually, um, I usually get off after w-watching you, with the toys," he confessed, biting back a moan as he began to practically thrust against my knee, the growing heat rubbing against me making me wet. That, and the new mental image of Jake downstairs, thinking of me and getting off, was making everything so much hotter.

  "Really?" I purred, wondering if he had done such things on the coach we were currently using. "And here I was thinking you were just working the entire time."

  Jake looked up from my shoulder, shooting me an unimpressed look that made me laugh.

  "You do work really hard, I know," I said, running a hand down his back. Jake returned the favor by nuzzling his lips against my neck, sucking on the skin until I was sure there would be a sizeable hicky later. It went straight to my crotch.

  "But I have to wonder," I began, trailing my hand down his stomach now, using teasing touches that stayed just out of reach where our bodies were connected, his hips still making small movements to roll against my knee, "If you jerk off in here... Have you ever used any of the toys on yourself?"

  Jake tensed over me, the redness that spread from his face down to his neck all the answer I needed. My own face felt slightly flushed as I grinned, delicious mental images of what I had been missing out on in the basement at night causing me to consider taking up nightly visits whenever he spent too long down here.

  "It-it's nothing too much, just, you know, testing them out," Jake muttered, averting his eyes as his groin moved away from my knee. I sighed, cupping his cheek and gently pushing him to face me again. There was embarrassment in his eyes, but uncertainty too.

  "Jake, I literally test out the products every day, there's nothing wrong with that. If anything, I'm glad you got to enjoy them as well." I took one of his hands, leading it down, right over my crotch before popping the button and leading his hand to feel my wet mound. "Just thinking about you using them, pleasuring yourself on them, makes me so wet. We've already seen each other in completely and utterly fucked up states- this is no different."

  "But it is," Jake said, his fingers spreading over my opening but not doing much more than that. If anything, he was simply cupping it, holding the warmth in his large hand. "Back then, you were simply my boss, but now... It's different. I'm different, you're different, and the way I feel about you is different."

  "Different isn't bad, you know," I said, giving him a sly grin. He smirked in return, but it quickly faded as his negative thoughts took over again.

  "It's just, when we had sex to test out that toy, one of the first custom-mades for our regular customer, I wanted more. I wanted more than sex, I wanted your love but I knew you didn't feel the same way and... I don't know. We were still friends, and close, but I've spent the last few months wondering if that was all this would ever be, and it... It hurt.

  "You don't owe me any feelings, but I'm glad you told me how you feel as soon as you figured it out," Jake said, flashing me a thankful smile before placing a chaste kiss on my cheek. "I'm just trying to wrap my head around this. I mean, I had been so sure only a half hour ago that I was going to have to quit or something before my feelings could mess everything up, but... now you want me too? It's just... It's a lot."

  His head found its way between my head and shoulder against as his body dipped in exhaustion. The bags under his eyes weren't just for show; he really didn't sleep much at all last night. I patted his back, the mood from earlier almost gone now that his hand had snuck out of my pants to wrap around me and his hard-on was considerably less hard.

  "It's okay, Jake, being human is confusing enough and feelings aren't always clear cut when we need them to be. I know it isn't exactly anyone's fault, but for what it's worth, I'm sorry you had to go through the last few months alone feeling like that. I hope we can be more open with each other from now on," I told h
im, my voice low and almost a whisper in the basement, only the hum from the fridge upstairs and Jake's shaky breaths accompanying it.

  "I like you, I really, really do, and I want to see where this can go. Both us and this company, because no matter what happens it will always be a link we will share," I said, my hand reaching up and playing with soft pieces of his hair before frowning. As nice as the warmth of his body was, it was much heavier than mine and I was starting to feel to strain from bearing the brunt of his weight in my lungs.

  I patted his back a few times, breaking the solemn mood that had taken over. "Okay, big guy, no falling asleep here. You're going upstairs and you're going to sleep in that nice guest bedroom I so graciously allowed you to take over."

  Jake groaned, complaining as he got up but offering me a hand when he did. I smiled as I took it, recognizing my friend's normal self as he trudged up the stairs after turning off his work light. I followed behind him, right after I quietly grabbed a few things from the toy box we have on standby for over orders.

  Oh yes, I was going to make sure he understood the new development in our relationship very well.

  When Jake woke up some hours later, I was already in the kitchen, trying my hand at making an omelet. He paused at the kitchen's threshold, his eyes wide as he looked me over. In an effort to make sure he was fully awake, I had decided I only needed an apron over my bra and panties today. It made things a bit cooler, but it had the desired effect.

  "What? I might not be as good of a cook as you, but I can at least make an omelet," I said, my lips curving into a smile as he tried to tear his eyes away.

  "U-um, you're naked?" He said, waving a hand towards me as if to remind me.

  "No, I 'm not, I'm wearing underwear and an apron. You've seen me in much more compromised states," I said, working the spatula under the eggs as I turned my back to him, showing off more skin.

  I had to contain a laugh from the shaky breath behind me, Jake obviously enjoying the view.

  "I just mean, after last night..." Jake trailed off, his voice dripping with insecurity. I blinked, wondering if we weren't on the same page.