Dominating the Boss 18

It had been three months since the bet, and life had never been so good for me. There were times I had earned more, and there were times I had been hanging around with some spectacular women, but rarely had it happened at the same time because the former usually consumed my full time, leaving little opportunity for the latter. But now, stuck in the backwater town I had been sent to in hopes of forcing my resignation, I found myself in a rare comfortable situation. 

I wasn’t just lazing around and enjoying sex, of course. I had arranged several deals for the plant I had been working for by leveraging the old-boys network, occasionally even stealing work from the other plants. It might have damaged the overall company interest, but it beefed up the numbers of our plant, so it was all well. Of course, thanks to another small contract I had signed with Natalie using a shell corporation, each deal was netting me some nice pocket change. I hadn’t even forced her to sign that particular one despite its relative illegality, as she had done much shadier things already. What was another small indiscretion? Ultimately, the numbers for the plant recovered significantly, which was the most important thing. 

Even better, since on paper Natalie was still the general manager, it meant that she was responsible for dealing with all the pesky details like paperwork, delivery schedules, delays, and the other boring stuff, while I just traveled around, having expensive dinners with prospective clients and suppliers. In the office, I had nothing to do… Of course, I never liked laziness, so I usually found something to pass the time. One of these pastimes was currently under my desk, her raven hair sprawled over my lap as she did her best to bring me to a rapid climax. 

Seeing my boss under my desk trying to bring me into a climax hadn’t lost its luster yet, maybe because even after months of routine, Natalie looked at me with a fire burning in her eyes. The impotent kind, because no matter how much she hated her submissive position, too many metaphorical chains were wrapped around her for her to even think about trying to cut herself free. Her financial indistrections was not even important at this point, even though they were big enough to ruin her career. She knew that I was the architect of her recent success, with a button to destroy everything I had built. That was the nice thing about deals brought in by a network, they were just as easy to destroy. 

But even that wasn’t the biggest hold I had over her, I thought with amusement even as I exploded into her mouth, and she caught the result with practiced ease — I had been using our bet to the maximum effect for the last three months, turning our meetings into little romping sessions, occasionally even inviting Brenda to our little office games. Then, I received a message from Brenda, and smiled in amusement. Jenny was here. If I was a nicer man, I would have warned Natalie so that she could get under the desk. But I wasn’t, so I just wrote back to Brenda, telling her to inform Jenny that she could just walk in. 

I was ready when the door opened and Jenny’s cheerful voice rang. “Hi Nathan, are you excited for the holiday?” 

“Of course,” I said even as I pulled my zipper and stood up, sending Natalie one amused glance before standing up, leaving her trapped under the desk. Natalie was angry, but it was a wave of impotent, resigned anger lacking a will to act, because it wasn’t the first time I left her trapped under my desk. During the first three months of our bet, she had found herself stuck in a number of compromising positions, some even with Jenny. At least this time, she was still wearing most of her clothes. 

I walked toward Jenny, a smirk on my lips. I took the time to examine the exquisite view in front of me. She was wearing a loose white shirt that only left her forearms bare, though by keeping the top few buttons open, she had created a nice hint of cleavage. Her absolutely tiny shorts, on the other hand, left her legs bare, displaying their toned perfection to the world. It was a sight that tempted me to push her down and take her on the floor, ignoring everything else. Unfortunately, that wasn’t on the cards yet. “Oh, yes. With the plant surpassing all the targets, the headquarters arranged a spectacular retreat. We’re going to have some fun.”  

“You’re going to have some fun,” Jenny said with a sigh even as she put her fingers on her stomach, which was no longer completely flat, but showing a small bump. “No, you and Nat are going to have all the fun,” she pouted. “I can’t drink, I can’t party, I can’t even swim as much as I want,” she complained with a pout, but it was obviously a playful one, excitement blossoming the moment her fingers touched her stomach. 

I just smirked as I pulled her shirt up a bit before laying a gentle kiss on her stomach. “For some reason, I don’t think you’re unhappy with the obligations,” I said, and then landed several more kisses. “You wouldn’t have this perfect glow otherwise.” 

“You flatterer, this is all your fault,” she said with a giggle, pushing me away playfully, but I kept my arms around her waist playfully. “I was perfectly fine before you came poking around.” 

A chuckle escaped my lips. “Is that so. Because I distinctly remember a certain redhead begging me to fill her so that she could get pregnant, but maybe it was a different one.” 

“You better not dare,” Jenny answered with a mock warning, though her slap was a bit too hard to be entirely playful, a sign of her growing possessiveness. The last three months had been an interesting period, quite a bit different than I had been expecting. While my relationship with Natalie had been nothing more than a festival of debauchery during work -often leading to overtime, of course- at home, I found myself a part of a little twisted family, with Jenny determined to keep me in the loop for the baby. Though it was understandable, considering I was the father, and already told her that I was willing to have a limited role in their life, as long as they didn’t expect me to have sleepless nights. That part, they had to handle. 

I leaned forward and captured Jenny’s lips hungrily, my hands caressing her body, especially focusing on her breasts which became even more spectacular under the effects of her pregnancy. Her tongue readily met mine for a couple of minutes, before she pushed me back. “Natalie is not here,” Jenny said sharply, once again rebuffing my advances, but this time, it took more than two minutes for her to remember that particular detail, so I was making progress. 

That was the only small annoyance for me during the last few months. After the fateful night, threesomes with Jenny and Natalie had become a weekly affair, usually starting with a homely dinner and turning into a night of debauchery. They were fun, especially after Natalie abandoned her delusions of being the dominant one in the bed, but Jenny was still adamant to keep our sexual interaction restricted to Natalie’s presence. Even warming her up for anything other than chaste kisses took some time. She claimed that anything else would have been cheating. Of course, I could have made Natalie convince her but I didn’t, mostly because slowly grinding her resistance down was much more fun. 

“Are we ready to go?” she asked, trying to act nonchalant, but her hastened breathing and her blushed face suggested it was nothing more than a desperate attempt to change the topics. 

“I am, but Natalie had an urgent meeting, so she had to change her flight for tomorrow morning,” I said in a sudden burst of inspiration, informing Jenny about an imaginary change of schedule. Also informing Natalie, who was still stuck under the desk, and had no option to come out unless she was willing to answer some pointed questions about her presence under my desk. 

“Really,” Jenny said, disappointed. “But I already arranged everything. I don’t want to wait until tomorrow morning.” 

“And we can’t,” I countered even as my hands were still wrapped around her waist, holding her tenderly. “Since it’s a work event, the company is paying for Natalie’s ticket change, but we have to pay from our pocket if we want to change to tomorrow’s flight. And it will just simply waste a night of pampering. It’s better if we just take the flight, and Natalie joins us tomorrow.” 

“I don’t know…” Jenny murmured as she moved uncomfortably in my grip, but still stayed close. 

“Don’t worry, I’ll be there to protect my little girl,” I said, once again leaning to kiss her belly. 

“It’s going to be a boy,” she giggled, but her distraction was just what I needed. I dragged her out of the room, not even bothering to text Natalie about the changes. She was smart enough to understand her tasks from the snippets she heard. Unfortunately, while walking through the building, I had to stay away from her to avoid the gossip, but the moment we were in the elevator, my arms were around her waist once more. 

“Nathan,” she murmured, the silent walk giving her time to realize the dangers of an early holiday. Understandable, because it wasn’t the lack of attraction that kept her away from me, but a misguided loyalty to her girlfriend, a loyalty that Natalie had never reciprocated even before my arrival on the scene. 

“Honey, I’m the father of your child,” I said even as I pulled her even closer, putting a chaste kiss on her lips. “There’s no harm in us taking an earlier flight rather than wasting all that money. Natalie already agreed that it was the best idea.” 

“I guess,” Jenny murmured after a brief consideration, her red hair creating an exquisite pattern as she shook her head. Then, she turned determinedly to me, and waved her finger warningly. “But there will be no sex before Natalie arrives! Clear?” 

“Of course,” I lied. After all, the whole point of the scheme was to break her silly commitment. She looked a bit dissatisfied when I sealed the promise with another kiss, but only after I pulled back. She had no problem with our tongues battling while it lasted, nor when my hands slid down to cup her bottom. Unfortunately, the elevator ride was too short to do anything else. We maintained a light chatter as she took the passenger seat while I drove. It was a pity that asking for a little road head was not an option. 

Things once again became interesting when we reached the counter to drop off our luggage, when the agent informed me that once again I was lucky enough to get an upgrade to first-class. “Good news, but you wouldn’t let my lady fly in economy, right?” I asked, pointedly putting my hand on her belly while I laid a gentle kiss on her cheek, making Jenny blush while the clerk giggled.

“Oh, I can’t do that to such a nice couple, especially when they are pregnant. How far along are you?” 

“Three months,” Jenny managed to murmur, dipping her head, but still, a huge smile adorned her face, still unable to resist the temptation of cheering up when someone pointed out her pregnancy. Never one to miss such an obvious opportunity, I wrapped my arm around her waist, pulling her close. She hugged me back reflexively for a moment, creating the ideal picture of a happy couple. Then, I used the opportunity to sneak down and leave a playful grope on her bottom. “Cut it out,” she whispered, though anger was noticeably absent from her tone, just a playful frustration. After our weekly threesome sessions, a little grope only registered as impatient. 

“Play along, or we will lose our nice first-class seats,” I reminded her, followed by a gentle kiss on her lips. She tried to look angry, but the giggle that escaped her lips readily ruined that image. With a sigh, she surrendered and left a sloppy kiss on my cheek, earning a cheerful smile from the agent while she processed our information and printed out our boarding passes. 

We walked away from the desk, but I kept my arm around her waist, which she didn’t have any inclination to complain about if the way she leaned against me was any indicator. “There’s still time before the departure, should we drop by the lounge. Maybe we can drop by the spa?” I offered. “A massage would be good in your condition.” 

“Not for me,” she murmured. “I never liked the spa. It feels weird when a stranger touches my body,” she answered.

“Who said anything about a stranger,” I said, my smirk widening as I caressed her back. “You know that I’m not a bad masseuse myself,” I added, my smile blooming as I remembered a few encounters where I had displayed my massage skills for her, though I hadn’t been able to do anything more than a preview with her inclination to jump in my bones the moment she started to feel aroused while Natalie watched helplessly from the side. 

She looked indecisive, biting her lips as she considered the offer. But she also didn’t put up any resistance when I gently led her to the small massage room, leaving her in front of the dressing cabin. I would have liked to watch her undress, as seeing her naked body never lost its excitement, but I made a beeline for the employee responsible for the spa instead. A bit of fast-talk -and a generous tip- later, she allowed me to step into the massage cabin with Jenny despite it being highly irregular. 

When I stepped into the room, Jenny was sprawled on the massage bed, on her back, her red hair contrasting with the white of the towel, which, unfortunately covered her torso completely. And as much as I would have liked to pull the towel off and seduce Jenny into a sexual encounter, it wasn’t realistic for two reasons. First, we didn’t have much time before the boarding, and second, Jenny was rather loud when she got started. I doubted that the walls would have survived her cries. 

So, I was careful as my hands danced over her naked back at first, avoiding most of the sensitive spots. Instead, I focused on her spine and her upper back, earning soft gasps whenever I found a particularly annoying knot, the massage oil making the task even easier. 

Of course, the vanilla version of the service was short lived. I was working on a clock, and neither missing the flight, nor cutting the massage before it reached to a level that satisfied me. So, my hands wandered down, focusing on the small of her back a bit, though I was rather careful considering her circumstances. Still, I stayed there for a while, until her attempts to keep her moans in start to fail. 

At that point I moved even lower, knocking the towel that was covering her spectacular bottom to the side. “Nathan,” she said. 

“Come on, honey, it’s not like I hadn’t seen it before,” I said even as my fingers dug into her bottom, attacking several sensitive points repeatedly. 

“But-” she tried to say, only to fell into silence when my fingers passed dangerously close to her slit, which was starting to get wet. It was amusing to see just how easily her protests died under pleasure despite her earlier comments, stiffening in anticipation whenever I passed close to her wet lips. But despite her anticipation, I avoided the final contact. 

Several minutes under the pressure of near-misses of pleasure, it only took the slightest push to make her turn, giving a full-frontal view of her beautiful body, glistening with a thin layer of sweat, tempting me to push for more. And I could see her that she was not too far away from agreeing to it. 

Unfortunately, we had a plain to catch. 

I leaned down slowly, aware that she was watching my every move. Her heartbeat thumped strongly under my fingers, signaling her excitement. I leaned further, and her lips parted open, ready for a kiss that would doubtlessly lead into more fun activities. It was a pity that we needed to board. “We need to catch the plane, princess, so get up,” I murmured, and placed a mocking, chaste kiss on her forehead before leaving the room. The last thing I heard as I closed the door was a frustrated growl. 

I had to knock on the door a couple of times and remind her that we were about to miss the plane before Jenny walked out several minutes after me, with a glow on her face unrelated to her pregnancy. It was obvious that she tried to handle her burning need herself, but obviously failed due to lack of time. After months of non-stop high-intensity encounters, reaching a quick climax with just her hands was a challenge, especially when interrupted several times by my reminders about the departure.

“Let’s go,” she said, trying her best to maintain a displeased frown, but I put my hand on the small of her back, gently caressing along her spine just like she liked. Already close to an orgasm, she shivered, biting her lips to prevent herself from moaning. She sent me an angry glare, but it was met with an amused smirk. “Let’s go,” she repeated as she grabbed my hand, dragging me along. I just chuckled. 

With priority boarding, we easily passed the last checkpoint, walking into the first class cabin. My face shone with excitement. The first-class cabin was completely empty other than us and a stewardess, but it wasn’t the only reason for my smile. No, I smiled because the stewardess was rather familiar, though it had been a few months since our last encounter. 

“Hi, Tanya,” I said with a smirk.