Inappropriate – Part 8: A Mile High on the Boss’s Jet

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“Have you flown a lot in your life?”

At the sound of his voice, I was snapped back to reality, despite my head literally being in the clouds at that moment. I was on a plane—Victor’s plane—with Victor, headed to San Francisco as a surprise.

“Oh, uh, yeah, kinda,” I said. “Here and there, I guess. Farthest I’ve gone is New York City.”

“Ooh, it’s been a couple years since I’ve been there. Let’s plan a weekend there, too.”

I smiled in spite of how strange it all felt. To casually ‘plan a weekend’ in New York was unreal to the point where I felt like I was still dreaming, asleep in Victor’s bed. Or maybe I was in a coma somewhere, and I had gotten in a terrible accident right after I left TannerCorp the first time.

Malachi, the driver, had his own seats near the front, and he was using the plane’s WiFi to contact his family. Meanwhile, Jenny, the attendant spent time in the cockpit with the pilot unless Victor or I needed her. Victor mentioned it was a flight that was a little over two hours, but the weather in San Francisco was supposed to be absolutely perfect.

Perfect for what? I wondered.

Victor and I sipped our drinks, and I gradually felt more and more relaxed. We even snacked on the gourmet sandwiches Karoline had prepared. After about an hour, it looked like Malachi was asleep.

Suddenly Victor leaned over and placed his hand high on my thigh. I looked at him, and his green eyes were squinting slightly.

“What?” I asked, unsure what his gaze meant.

“Have you… joined the mile high club?” He asked.

My eyes got wide, and I shook my head. “Have you?” I asked.

“Technically. But are you, at all, interested in joining?” He slid his hand higher up and closer to my crotch. Suddenly my heart started pounding, and blood rushed to my dick at his touch.

There was a privacy screen, unbeknownst to me, that Victor stood up to close, separating our back half of the plane from the front, where Malachi slept. He walked back over, pulling a small bag from a nearby locking storage compartment.

In the bag was a bottle of lube. My eyes got even wider. I hadn’t said yes or no, but again, it felt like the choice was made for me. He set the lube on the table and moved our empty drink classes somewhere more stable.

“Lay your seat back as far as it goes,” Victor instructed me. So I did, and then he told me to pull down my pants, and he took his off and threw them on a couch, and I questioned why Victor wanted to do it in the seats instead .

So I undid my belt, and my hard cock sprang free as I pulled my pants to my ankles. Victor walked closer and squirted some lube on my cock before turning around and bending over, showing me his ass as he slipped a lubed finger inside. My hard cock was straining watching him.

“Oh, Victor,” I breathed. And then he turned back around and climbed over me. He faced me as he straddled, reaching down to my cock. I felt him line it up, and then he slowly lowered himself down.

The tightness of his ass was marvelous, and I let out a louder moan than intended as my head breached the ring. Staring in my eyes with his hands now on my shoulders, Victor let out a heavy sigh as slid farther down. When he came to a rest, my cock was almost overstimulated by how hot and tight his ass was. And the fact that I was having sex on a plane. Never mind that it was with the guy who owned the plane.

He quickly got to work riding me, and I was impressed with his thigh strength. He started grinding his hips in small circles, and then his lips were on mine. His heavy breaths underscored his rabid kissing, and the feeling of his ass going in circles felt like nothing I’d ever felt before.

“Oh, fuck,” I groaned between kisses. I felt his hands go back to my shoulders, after letting my hair down, of course, and he started to bounce up and down again.

Every few seconds, our lips would meet again, his tongue would slide back to find mine. The only time he wasn’t staring into my eyes was when we kissed, and in some ways, I’d never felt closer to him. That could have been because the table behind him was wedged into his back, though.

As he continued riding me, I reached between us for his cock. He’d placed the lube on the table behind him, and so I reached behind Homans squirted some on my hand and grabbed his cock again.

“Oh, shit,” he hissed. So his cock wa s basically fucking my hand as he bounced up and down, and it was very hot.

We kept at it, and before long, I could tell I was close. But suddenly, there was a bing noise, and the pilot’s voice came over the PA.

“Hey, guys. Uh, we’re about to hit some mild turbulence here, so just make sure everyone’s buckled up. Shouldn’t be too long.” He spoke with a rather flat affect that seemed required of pilots.

But Victor did not heed his warning about turbulence. He didn’t climb off of me and buckle up. Instead, he increased his tempo, bouncing more wildly on my cock.

“Oh, I’m close,” I groaned softly.

“Good,” Victor said, pulling up my shirt. “So am I.”

But then came the turbulence, shaking the entire plane. There was a deep rumbling sound as the plane shuddered, like all the plastic and wood paneling was vibrating. It was quite loud, really, but the noise was loud enough to cover up whatever noises we were making. And the turbulence shook it just right where Victor’s tight ass was squeezing my cock in the most perfect hug, and I was suddenly on the edge as he bounced involuntarily on top of me. I couldn’t hold it back, even as I tried to hold on.

And so, as the plane rocked with turbulence, I started unloading inside Victor’s ass.

“Ohh! Oh fuck, I’m cumming!” I moaned loudly, the sound covered up by the deep rumbling of the trembling plane as Victor stared into my eyes.

I jerked his cock as fast as I could as my own dick twitched inside him, and I watched his eyes squeeze shut as he moaned, “Ohh, shit!”

I felt his cum splatter on my chest, the plane still shaking. He leaned forward, grinding his hips in little circles again as he came, and then finally, the plane stopped shuddering and creaking.

“All clear, guys,” came the pilot’s voice. “Feel free to get up and do cartwheels if you so choose.”

I looked into Victor’s eyes as he caught his breath, my cock still inside his marvelous hole. He had ridden my dick like I had only ever dreamed, so I reached up and grabbed his face, pulling him in to kiss me for a moment as my cock softened inside him. He soon climbed off of me, reached my I a different compartment for a towel, and wiped himself clean before tossing the towel to me.

I wiped myself clean, too, and we both re-dressed before Victor opened the privacy screen. Malachi looked back at us, but I assumed he’d woken up from the turbulence. Victor and I sat down on the couch, now, so I got bold.

“Why didn’t we just do that right here? This seems easier to maneuver than those seats,” I said with a smile. “Not that I’m complaining. That was so good.”

“Spur of the moment, I guess,” he replied. He looked at his watch. “We still have about an hour if you’d like to…”

I considered it, truthfully, but I knew my body needed a bit of time between rounds. But I did know we’d be flying back soon.

“How about I bottom on the flight back?”

“I’ve never topped on a plane, actually,” he admitted.

“Then we have to,” I grinned.

——

The plane landed, and Malachi and Jenny made quick work of clearing us and our things from the plane to a waiting car. I thanked the pilot, whose name, I learned, was Clark Browning. Clark had his own accommodations, as did Jenny and Malachi. And Victor and I did, too.

The hills in the city were insane. This was my first time in San Francisco after seeing it in movies and on television for so many years, and it really looked just like I expected. Soon, Malachi drove us into the parking garage of a hotel on a very busy street.

“Let me guess… Your dad is friends with the owner,” I smiled.

“Actually… Aaron is an old friend of mine from college,” Victor replied. “And he’s quite the hotelier. Rest assured, our suite does have a jacuzzi.”

We were escorted to our room by two well-dressed and polite bellhops who unloaded the car in no time. We took a small elevator up to the highest floor, and the bellhops unlocked a door to a long, ramped hallway leading to a room labeled Exec. Suite. Once inside, I was agog—the room had endless sunshine streaming in from every angle with windows on nearly every wall.

There was, as Victor said, a jacuzzi that as even larger than the one in Seattle. I could spot a few beds and smaller rooms, as well as a walk-in closet where the bellhops were delivering our bags.

Soon they were gone, leaving Victor and me alone in the sun-bright suite.

“Welcome to San Francisco, Garrett,” he grinned. “I haven’t been excited to be here in years, but I’m really excited today.”

He walked up to me and grabbed my arms, leaning in for a kiss. I kissed him, inhaling the scent of him, wrapping my arms around him to hold him.

“I don’t think I know how to say thank you properly for all of this,” I breathed.

“Well, tomorrow you are technically here for work.” Victor’s voice was light, airy like he was laughing.

“That’s fine. I don’t mind working. What’ll I have to do?”

“You’ll sit in the meeting with me. You’ll take notes down for me to review later, and you can help me and get me anything I might need during,” he explained.

“Like coffee?” I raised an eyebrow.

“Garrett, the only way you could come on this trip without having to stay completely hidden is if you’re here as my assistant,” Victor reminded me. “It’s just how it has to be right now.”

“I know,” I replied.

“But for today, you’re my boyfriend,” he smiled. But then his eyes got really wide.

“Oh?” We hadn’t put a name on anything yet; we hadn’t labeled what we were yet.

“I’m sorry,” Victor said, taking a step back. “That’s a big word.”

I closed the gap, stepping into him, grabbing his waist.

“Don’t be sorry,” I told him, leaning closer in, so our faces were touching. “I can be your boyfriend. Do you want to be mine?”

“Very much,” breathed Victor. “If you’ll have me.”

“Of course, Victor.” I grinned. “I think the matching PJs were already enough to know we were something special.”

“I really believe we are,” said Victor, leaning in to kiss me again.

As he pulled away, he walked over to a phone in the largest bedroom and buzzed the front desk to ask for a bottle of wine. One of the same bellhops arrived minutes later with a chilled bottle and some glasses, so Victor and I sat down to enjoy them.

“It’s barely noon,” I said after a big gulp of wine. “What do two boyfriends have to do in San Francisco?”

“Well, it’s one of the gayest cities in the country, so we could explore the Castro district.”

I’d heard of the Castro. But I’d never been, and I didn’t know what to expect.

——

Malachi dropped us off, and Victor gave him some money and told him to return in three hours. And then, Victor and I walked around together, in broad daylight hand in hand. It was nice to just spend time in public with him.

But in doing so, I realized how being so secretive had made me felt. By keeping it a secret, I began to feel like a dirty secret. I knew Victor had his reasons, but I wasn’t accustomed to hiding like that. And now being in an area where so many people were unapologetically themselves, surrounded by people they chose, I felt a little sad, wishing things could be different.

I hoped that one day they might be. Victor, Sr., should be fine. Just because I wasn’t made of money didn’t mean I was undeserving of Victor’s affections. I hadn’t asked for anything other than what was offered. I wasn’t a gold digger.

But in the meantime, I decided to have a nice day with my boyfriend. We walked the streets, we even went to a museum all about queer history. There were a couple gay bars we stopped into, too, and even though it was midday, we still managed to have some fun and get a light buzz.

Eventually, Malachi arrived to pick us up, and he drove us across the Golden Gate Bridge to a beautiful restaurant just north of the city in a beautifully wooded area. Victor encouraged me to try some fish, and I ended up really enjoying it.

After dinner, Victor had Malachi drop us off at the northernmost point of the Golden Gate.

“We’ll find you on the other side,” he said as we hopped out of the car.

Then in the golden light of the sun, Victor and I started to walk the length of the bridge. We were on the side overlooking the bay, and I pointed out Alcatraz.

“We can go there if you want. Maybe tomorrow after the first meeting,” he said, his hand on my lower back as we walked.

The deep red color of the bridge made a beautiful backdrop for a picture of Victor and me, which I saved forever.

By the time we reached the midway point, the sky was a beautiful, breathtaking golden-pink. I stopped in my tracks, and Victor almost breezed past me. But he turned back, and I grabbed him for a deep kiss.

“Thank you, Victor,” I said.

“For what?” He smiled at me and kissed me again.

“For seeing something in me. I’d started to believe I was destined to take on the rest of this life alone… But now I don’t have to.”

“That’s so funny, because I thought the same thing. Until that day you came into the office, I thought I’d be content as a bachelor until I died, like my father post-marriage, but when I saw you, I saw hope. I felt a desire for a future. I know that’s crazy, but it’s true.” We kissed again as crowds passed us by, as several lanes of speeding cars breezed by.

The stillness of that moment was what stuck with me as we left. We were completely still, for what felt like the first time, was the world passed us by. I felt like I had a chance to breathe, to get caught up. Victor was a tornado, and I was Dorothy’s house, plucked away from everything I knew. But a moment like this was slow, it was special, and it was for us.

We found Malachi soon after completing the trek, and he drove us back to the hotel for the night. The sun had set before we got upstairs, and the suite was now illuminated by white LED lights and fluorescents. Victor pressed a button on the wall, and all the blinds closed at once.

Victor ordered up some more wine and some desserts, and he got the jacuzzi going for us. I managed to figure out how to play some music on the surround-sound speakers, and we took turns giving each other a lap dance as we undressed for the jacuzzi.

I went first, pulling out all my best sexy moves, and once I was naked, I sat down on the chair and watched Victor. But in that moment, I became convinced he had been a stripper or a go-go boy. My eyes widened as he slowly took off his shirt first, revealing an inch of his body at a time. Then he turned around and bent over, winding his hips before straddling my legs. His pants came next, and I had to fight all my urges not to rip them off and bury my mouth in his ass. There was a sensuous fluidity that Victor displayed that was really turning me on.

By the time he was naked, I was rock hard.

“You’re so hot, Victor,” I explained when he grabbed it with a raised eyebrow. “I can’t help it.”

“Mmm,” he moaned softly. “Come in the water with me.”

“Won’t that be hard to clean?” I winked at him.

“Not at all,” said Victor as he sank down into the water. I could’ve sworn I saw his cock hardening before it dipped under.

This time, I climbed in on Victor’s lap to face him, tow bottles of wine right next to us. I still couldn’t get over drinking wine by the bottle, as if it were Gatorade at a track meet. But I definitely wasn’t going to complain.

And I was right. Victor had an erection, and it was poking my ass as I draped my arms around his neck and kissed him. He squeezed me around the waist, and I giggled.

“This is so… unreal,” I said. “Like, since the day I met you, I’ve felt like I was dreaming.”

“Not to be cliche, but I feel the same way,” Victor whispered in reply. “You’re a lifelong wish come true, Garrett.”

I felt myself blush yet again, so I leaned in for another kiss so I wouldn’t cry. It was as if I had found someone who genuinely wanted to be with me. But we had to hide from everyone at the very workplace he’d pigeonholed me into.

I, obviously, felt torn. Was Victor just preying on someone he knew was desperately alone? Was he tempting me with greener pastures, only to fence me in?

Instead of worrying, I leaned in to what I could physically feel. I could feel the hot water bubbling around me. I could feel Victor beneath me. His hard penis pressing into me. His lips against mine. His hand reaching for my dick.

He’d given me no real reasons to be doubtful yet. So I also felt guilty for questioning him when he’d been nothing but generous. So I kissed him deeper, my body’s apology to him.

He was jerking me under the water, so I reached beneath me and grabbed his dick, too. I stroked him, lightly riding up and down, tugging the skin of his dick as I went.

“Hey,” he said suddenly, shifting his grip back to my hips. “Did you ever go in a hot tub or a pool when you were younger?”

“Yeah?” I looked in his eyes, confused. “Of course.”

“And did you ever… explore the jets?” He raised an eyebrow.

“What do you mean?” Of course I knew there were jets in hot tubs and pools.

“You know… like…” He stuck his pointer finger out and wiggled the three long fingers in his other hand against the tip. “Explored the jets.”

I understood. “No, not really. I mean, maybe?”

“You never just… posted up in front of a jet and pretended someone was touching your wiener?” He laughed.

“I guess not,” I chuckled. “Is it… nice?”

“I mean, not as good as your mouth, but it definitely feels nice. I thought it might be fun to, like, turn around and let the jets do all the work.” So I climbed off of his lap, and he stood up and turned around. We moved the wine closer to us, and we both perched on our knees.

After some maneuvering, I managed to line the head of my cock up with a strong, pulsing jet of water.

“Ooh!” I sighed.

“Right?” He laughed and took a swig of wine.

We kept kneeling as we continued to chat and drink. But I couldn’t focus on much other than the intense stimulation on my cock. I felt Victor reach back, and his hand found my ass. He squeezed it before walking his fingers toward my hole. So I reached back and found his too.

We teased each other’s rings as the jets blasted the front side. He managed to get the tip of his finger in me, thanks to the water, and so I tried my best to do the same.

“Oh, wow,” Victor gasped. “I’ve never finished this way.”

“Let’s do it,” I whispered. And his face turned toward mine.

We kissed and fingered each other as our respective orgasms continued building. Before long, I knew I was close.

“I think I’m gonna cum,” I hissed. “Where should I—“

But it was too late. I looked down and saw as a jet of cum spewed from my dick and was immediately caught in the forceful jet and washed away.

“Ohh! Oh my god!” I shouted. It was really intense.

Then Victor suddenly grunted, “Mm! Shit!”

We were both cumming, hands-free, in the jacuzzi. It was definitely far from sanitary, but I was too turned on to care. Victor kissed me again, and we got out of the jacuzzi and drained the water.

He held my hand as we walked, wine in our other hands, to the shower. We rinsed off, toweled dry, and slipped into our silken pajamas. This truly was a life I never dreamed of, but I liked it. I liked it a lot.



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