Dominating the Boss 20 (Patreon)

The dance of hesitance on Jenny’s face was a nice change from her normally confident expression, especially when she was trying to stand still, but unable to prevent herself from squirming. Not surprising, considering I had just challenged her to masturbate publicly. Jenny might be amazing between the sheets, comfortably rolling with anything Natalia or I came up with, but when it came to more irregular actions, she was much shyer. 

Normally, that included the displays of public loving. If I had challenged her in a more crowded place, I knew that I would receive a genuine scolding, but I was betting on the fact that other than our stewardess —a sexy but nonthreatening blonde bombshell— we were alone. The fact that she was still raging to go after masturbation —she had been hard to exhaust even before the additional pregnancy hormones joined the fray to boost her desires even further. 

I had no problems leveraging that situation for my tastes. I wanted my Jenny to be more adventurous, she deserved to be so with her amazing body… 

“Do you think… But I can’t…” Jenny murmured after a while. 

“It’s okay if you can’t handle,” I answered, but I made sure to keep a small smirk on my face to maintain the levity. “After all, not everyone has the courage.” 

“You think so,” she murmured, trying to mirror my smirk but unable to keep the edge of hesitancy away. She might be a ball of hormones, but her hang-ups weren’t easy to overcome. 

“Why don’t you prove otherwise,” I said, letting my smirk widen as I leaned forward, our lips separated by an inch, hers parted open readily to meet halfway. But I kept my position. “Only the brave girls deserve a reward,” I murmured in a throaty tone that I knew for a fact it drove her crazy, and burning her eyes alight with desire. I put a blanket on her lap, and pulled back. “Are you a brave girl, my little beautiful Jenny, or are you going to let your fear prevent you from having a perfectly innocent bit of fun…” 

“I’ll show you, you bastard,” Jenny murmured determinedly, though, her expression failed to match the strength of her tone, flailing badly. I let that go unmentioned, because she was carefully spreading the blanket to her lap, meaning she decided to follow my direction. I licked my lips in anticipation as her hand disappeared under the blanket, struggling a bit before stilling, 

An expression of fearful determination appeared on her face as her arm started to move, her lips pressed tight like she was afraid of an errant moan escaping, her eyes darting back and forth, making sure no one was there. “Keep your eyes upfront. You’re looking more suspicious this way,” I explained her kindly even as I caressed her shoulder tenderly. No need to spook her when she finally gathered her courage. 

“I see,” she murmured as she turned her gaze to the widescreen, acting like her attention was on the movie. A good idea, if it wasn’t for concentrated expression and glassy eyes, enough to arouse suspicion. Luckily, we didn’t have to hide anything. 

I watched her move, but I noticed her movement range was still limited. Suspicious, I moved my fingers under the blanket, exploration showing that she was still wearing her tight shorts, her hand jimmied inside. “Come on, honey, your jean shorts are too tight for your fingers to have a range of motion. You won’t enjoy it until you get rid of them. 

“But what if she comes with drinks,” she asked fearfully. 

“You’ll still have your blanket,” I reminded her. “And this is first class, there’s no way she could say anything even if by some freak chance, she notices something,” I said, misrepresenting the chances of Tanya noticing something while simultaneously removing the negative consequences. It was a straightforward manipulation, but Jenny was in a particularly vulnerable state with her arousal. 

She looked like she wanted to continue arguing, but I was ready to distract her. My hand already under the blanket, it wasn’t difficult for me to slide my hand to the side until my fingers were digging into her inner thigh. She gasped in shock, and I just smiled in response. She was coming around the idea. “Are you sure?” she still asked. 

I decided to give the answer in a better way. I leaned forward with intentional slowness, my lips already parted, ready to smother hers. She looked hesitant, but that didn’t prevent her from leaning forward, her lips shining with arousal. We met in the middle for a surprisingly chaste, lingering kiss. The situation was a bit more erotic, of course, considering her hand under the blanket suddenly picked up the speed. I let the kiss linger, boosting her arousal further and further, so, when I slid my hands under the blanket and grabbed her short, she raised her bottom, easing my job a lot. 

Free from the tight restrictions of her short, her fingers quickened significantly even as her back arched, our lips still locked together. Her tongue darted out, meeting with mine in the middle for a heated battle, her ability to keep a lid on her moans compromised. My hand free from its task, I was free to explore her amazingly fit body to my heart’s content, but I stayed limited to the kiss. 

The moment was about breaking her taboos, not fulfilling my immediate desires. 

When I pulled back, she let out a soft whine. “Please, don’t go,” she whined, her beautiful eyes shining with desire. 

“I’m not going anywhere,” I explained. “But you can’t expect me to miss the incredibly sexy sight of your single-person game. It’s a milestone.”

“Do you really think it’s sexy?” she murmured shyly. 

I couldn’t help but smirk in amusement at her sudden burst of insecurity, making her look adorable. Adorable enough to eat. “Sweetie, are you kidding me?” I said, the desire in my tone genuine. “You’re a sexy redhead goddess, and watching you bravely owning your sexuality is one of the sexiest scenes in my life,” I explained, stretching the truth a bit in the second part. Yes, she was amazingly sexy at the moment, but not enough to get a seat in the hall of fame. 

“Just one of?” she said, flirtatiously. 

“Well, it’s a difficult competition,” I said, and she frowned a bit, clearly not appreciating to be compared to other girls and coming short. I continued before jealousy soured her mood. “There’s the time where I watched my seed dribbling out of your exhausted body after a six-hour marathon, or the day we spent in the private bathtub after I spent the whole day pampering you while you mewled like a little kitty, or the time…” I continued, her blush intensifying at each passing second. 

“Really,” she murmured, blushing further as I reminded her some of our more spectacular memories. “How about now?” With that, she pulled the blanket to the side, giving me a glimpse of her hand caressing her entrance, straining her flimsy underwear significantly while her other hand landed on her chest, teasing her breasts over her shirt and bra. 

“Much better,” I answered as I leaned back a bit, my gaze firmly on her body, my shaft in full mast once more despite the spectacular blowjob I had received minutes ago. “But how about if you give me a better view?” 

“That will be too risky,” she said, and for a moment, I felt disappointed, thinking I might have read her level arousal wrong, then she continued.” I need something to compensate for the increased risk, what’s in for me?” she added, and I smirked.

“How about a nice reciprocal gift in return,” I said as I pulled my zipper down while I kept my eyes locked in hers. Her breathing quickened further, showing her excitement at the idea, her fingers only a second late to follow their direction. When I struggled to free my raging erection from my pants, she raised one of her legs a bit enough to give a much better glimpse of her entrance. “Excellent view,” I said even as my hand started trailing my shaft, my eyes drinking the sight. 

“Maybe even enough to get into the hall of fame?” she murmured shyly, desire dancing in her eyes. 

“Almost,” I answered, and she frowned for a moment. I used the opportunity to lean forward and grab her panties, their fragile fabric unable to resist my pull for a second before ripping apart. I wrapped the fabric on my hand, using it to masturbate, her wetness clear against my skin. She stood frozen. “Now, it is,” I answered. She trembled in fear and arousal, trying to close her legs for a moment before I warned her. “You don’t want to lose your glorious spot in the hall of fame, do you?” I said, and she trembled once more, but her legs stayed wide open, her fingers alternating between circling her clit and sliding inside. 

“You’re a bad, bad man,” she murmured, but even if she was feeling cross, it was hard to maintain anger while she was steadily climbing toward an orgasm soon after a previous one. 

“Are you complaining?” I countered with a challenging smirk. 

“No, not at all,” she answered as she pushed her fingers deep into her entrance, her ecstasy climbing more and more, tempting me for more. 

I decided that it was time. “Do you need any assistance,” I said even as I leaned down and grabbed her feet, pulling it to my lap before she could react to it. She looked a bit put off, but when I started rubbing her soles with my empty hand, complaints melted quickly in lieu of a fresh rush of desire. I caressed her soles repeatedly, trying to force her loudly as she drove quicker toward her orgasm, but she bit her lips determinedly, keeping it hidden. She even threw a smug smirk at me as the orgasm hit, her body rocking silently. 

Unfortunately for her, her distraction was all I needed. While her attention was focused on combating the temptation to cry, she was too occupied to understand the implication when I grabbed her wrist and pulled her onto my lap. I didn’t push inside her no matter how much I wanted to, as that was something she was going to be done in her own volition. Still, I could feel her wetness on my shaft as she moved up and down, triggering my arousal. 

“What are you doing!” Jenny exclaimed loudly, loud enough to arouse attention, she tried to stand up, but my arms were already around her waist, preventing her from standing up. 

“Come on, sweetie, I need a bit of help from you, it shouldn’t be a problem, right?” 

I had a feeling that, if it wasn’t for the after-effects of the spectacular arousal she had just gone through, I would have received a sharp negative. Instead, she turned to face me, her expression wavering. “But, wouldn’t Natalie be angry about it?” she asked. 

“It’s not that different what we have been doing moments ago,” I said. “You just need to caress me a bit to make me climax easier.” She still looked undecided, so I put my hand on her hips casually before trailing toward her inner thigh, my touch awakening her arousal once more. “Come on, Jenny, you owe me that much,” I added in a pleading tone, trying to push a decision to her. 

However, before she could answer, she stiffened because she saw Tanya walking from the other end of the corridor. I reacted much quicker, grabbed the discarded blanket, and pulled it on her lap, hiding her nakedness from the sight. She looked at me, panicked, because my erection was forcing the blanket to make a tent between her legs, making the situation extremely obvious.

“We need to hide this, quick,” I reminded her.

“How?” she answered panickedly. 

“How do you think?” I answered, giving her a glare, but didn’t make a move to actually make her move. After all, if worst came to worst, I knew that Tanya would act like she didn’t notice it. However, Jenny didn’t know that, and the sudden rush of embarrassment and the panic from the risk of being caught impaired her rationality quite a bit. 

It took everything I had not to break into a snigger as she raised her hips for a moment, though the heat that covered my shaft as she lowered herself was a good distraction from it. I tightened my grip around her waist, and when she sent me a nervous glance, I nodded reassuringly. 

Then, Tanya was here, carrying two drinks and some light snacks. “How’s the flight? Any updates?” I asked Tanya cheerfully while Jenny tried her best to act nonchalant, but betrayed by the thick blush that covered her body.  

“Nothing noteworthy,” she answered. “We are on schedule, and will take two more hours before we’re at the destination.” 

“Excellent,” I said as I shifted in my place, which, considering Jenny was still on my lap, pushed my shaft even deeper into her core. She looked at me angrily, but from the way she clamped around me, I knew that despite her protests, I wasn’t the only one enjoying the moment. Not surprising, considering that she decided that taking it fully inside was the best option to hide our situation. 

The way Jenny stiffened on my lap while Tanya played the food on the tray was spectacular. Luckily, she was distracted by her own situation, because she failed to notice Tanya’s spectacular cleavage —two buttons open, leaning forward, bra absent— therefore didn’t get suspicious. I winked at Tanya in a moment of eye contact, and she blushed further. 

Meanwhile, I decided to amp up the challenge for Jenny as well. One of my hands was under the blanket, close range to her clit. A push later, I was circling around her sensitive spot, adding another layer of arousal to her game. She tried to look at me angrily, but she was helpless. The authenticity of her anger was in doubt as well with the desire burning in its depths. 

“Can you please get me a glass of fresh pineapple juice, urgent,” Jenny said, trying to send her away, which would give her the opportunity to gather the situation. Smart, but I was one step ahead of her. Her shorts were dangling around one ankle, so while Tanya walked away —with a rather excessive sway on her hips, I noted with interest— I stepped on it so when she tried to stand up, it stayed in place. 

“You’re pushing your luck,” she started, but I had no intention of letting her finish her frantic statement. I grabbed her ripped panties and stuffed them to her mouth before pushing her forward. She pressed her hands against the next seat, which gave me the perfect access to her bottom. 

Her moan was muffled as I slid inside her, invading her insides in a display of dominance I usually tried to keep away from her, saving it for Natalie. “The sooner we finish, the less chance we get caught,” I explained to her even as I slammed inside her again and again, her hips rising to follow the demand. Soon, her moans rose enough that I had to keep my hand on her mouth, preventing her from alerting the rest of the plane.  

I was caught flat-footed by the sudden shudder followed by her walls clamping around my shaft, finally triggering a climax of my own. Her legs trembled, but before she could stumble, my arms were around her midsection, and I pulled her back with me as I sat back down, once again pulling the blanket on, my shaft still inside her. 

Truth be told, I was slightly afraid about the consequences, but when I pulled off her panties from her mouth, the only thing that left her mouth was an appreciative mumble. “That was … amazing. Now, I can understand the big deal about the mile high club…” 

I snorted, not bothering to inform that it was far superior to the usual fare. After all, why would I, when she was mine, and was going to experience the high-quality version again and again… She had no need for the mediocre stuff. As she slid down to slumber, exhaustion catching up with her, my mind was on how best to leverage Jenny’s loosening sensibilities. We had a full night in the hotel alone, and I wanted to use that to the best of my ability.