Up in the Air

An Erotic Series

Getting ready for dinner was more awkward. No big preparations, just playing it cool while smelling good and not being a fumbling mess. That didn't stop me from trimming my stubble a bit, nice cologne, no tie but a nice shirt and vest. Lining my pockets with essentials, I took my jacket and headed down to the lobby. In the elevator, my phone pinged and showed Kai's name, so I opened it.

Kai: On my way. Took forever to have a cab that goes to where we need.

Me: No worries. Take your time and I'll see you soon.

Kai: Fingers crossed you don't hate me.

Me: Hard for me to hate anyone.

Sending a smile... emoji I think they're called, I closed my phone and walked out the doors toward the hotel entrance. I'm old and not old and don't know if the moving pictures are called GIF or JIF. No sooner than I didn't, I turned to see a flush of rich charcoal grey with Kai's eyes and smile facing me. The blue in his eyes popped, as did the cross earring he had and the black of his shirt. Simple... but it's as if he were glowing without trying. As my brain caught up, I tried to find something to say.

"Wow... you look... stunning."

"Hehe... thank you. Didn't want to be too casual or overdue it."

"If seeing more of you means adventure and this glow, I think I'd crash land for once."

Kai blushed red, pulling on a lock of hair on the back of his head.

"You're really one for compliments aren't you?"

With a smile, I opened the cab door and winked.

"Depends on if you're wearing a ponytail and won't fly off."

"A yes then."

He happily sat down, taking my hand before I closed the door to get in. With a tug, I figured he wanted me to get in on that side and I managed to slide in next to him and shut the door with my free hand. Cab had more room than I thought, which is always nice when you're a big guy. As we drove, he never let me go, and I felt nervous, flustered, and a bit turned on... His hands were soft, and felt kind. Kept thinking if I should put my arm around him... or if that was too forward as a friend.

* * * * *

Glancing over, I saw Kai wearing a short ponytail, colorful bears strung through. Damn it... was everything about this guy pretty? When he caught me looking, he smiled shyly and fiddled with it.

"No one gets to see how long my waves really are. If I ever have time to straighten them, it gives me an excuse to wear this hair piece. It was my mother's... She gave it to me after seeing my first major show... Saying it'd bring me luck. Sorry if I'm talking too much about my mom or anything not... vague. It's been busy and I cope like that."

"I don't mind listening Kai. Hearing people talk at me then long periods of whirring electronics and metal for a living makes me happy I can hear a friend speak to me. You're fine... I promise."

He nodded, squirming a bit while trying not to lean on me. Putting an arm around him, hand still held in his, my heart sped up and his thumped against my side.

"You smell nice..."

"Thank you. I showered."

With some giggling, we sat in silence for what felt like an eternal car ride. Pulling to a stop, I looked out to see a restaurant that looked rather new with an open dancefloor beside it. Still holding my hand, Kai led me out and I saw the full extent of the building. Quaint, instrumentals, and secluded. I didn't get a full impression before he led me inside. Someone caught our eyes, who kindly greeted us then walked to a spot away from others. Leaving us alone, I pulled out his chair then going to sit on my seat, seeing him trying to hide his smile under a sort of pout.

"Something wrong?"

"No... Just wish I could not like you so much. If I were forward, I'd ask you to get married."

"Hehe, well, we might, and I say might, work up to that. Best not rush."

"I get it... Feels really nice though. So thank you."

"Thank me by letting us meet more often."

"If our schedules let that happen, I'll happily take you to dinner again."

"Together in Paris."

With a nod, Kai's face glowed, thinking of what might come in the future.

"Together in Paris it is."

The same waitress came back, placing some water and another clear drink that smelled floral. Putting it to my nose, I knew it was alcohol but not what kind. Taking a sip, I choked a bit, and Kai tried not to laugh but followed behind me in choking. Though we chit chatted, it was quiet between us, enjoying the company. Though I was curious about why we were brought things and not asked, Kai put my mind at ease. The way this restaurant worked was you called in advance, and were greeted by someone who'd take care of you. Making it clear what your party liked and what might cause allergic reactions, a menu was customized for a unique experience.

Pressing to hear how much it was for all of this, he shrugged and kept his lips sealed. Eyeing him suspiciously, I poked fun that he was trying to poison me and we both had to keep ourselves quiet from the loud chuckles echoing. The silence was eerie, though there were a few other parties here as well. But it didn't make the experience any less fun. Every half hour, a new small plate of something came out, some looking weird and others tasting like something entirely different.

* * * * *

One looked like a tiny lobster and I felt weird for having it stare at me. I showed it to Kai, who made a face at the eyes too. We didn't really touch that one. After a lot of food, we started with desserts. No chef can mess up dessert. As we waited, I stared at Kai, profile of his face looking dreamy... Is that a crime to say that? I feel that after you're 20 something, you can't have schoolboy crushes or wonder anymore. Sometimes I don't think I fit in that phase of life at 42.

I looked away before he caught me, but when I looked over again, he moved over to me, eyes staring his down. Leaning down, I tried to kiss him without thinking. He was surprised by it... but accepted as his hand reached for the back of my neck and our lips pressed over and over. That kiss felt like it'd gone in slow motion... no matter how short it really was. When one of us pulled away slightly, the other tried to have the kiss go on longer... But I gave in to stopping first.

This wasn't what we were here for... and the hard feeling that pressed in my pants wasn't meant for right now. Looking over, his pants were tight on him, cock pressing through as he tried to cross his legs and cover his face. Adorable... I tried to say something that wasn't stupid but stuttered through it.

"Uh, I'm sorry. Really sorry. No idea why I did that."

Kai whispered loud enough for me to hear, still not looking up at me.

"Don't be... I liked it... But this feels so quick. And it's right to me at the same time."

"Emotions are complicated like that."

"Yeah..."

"I understand if you don-"

"I feel the opposite... I want to see you more... But don't want to make promises with how our schedules are."

"There's no harm in trying, right?"

After some quiet, Kai looked at me, eyes shining, laying his hand over mine.

"No..."

Leaning down, I put my forehead to his, a soft smile on my face.

"Then I'm okay with that."

* * * * *

Once we'd gotten to the hotel, everything screamed in me to fuck Kai... Coax him upstairs and let myself melt into each other without thinking. His body said the same, eyes spelled it out to me, but he resisted the same temptation that danced around my head. Kissing his hand and stealing a second kiss to his lips, we said good night and hoped to meet sometime soon.

Loosening my tie in the elevator, I was dazed. Felt like I'd be drugged or given a lot to drink. In truth, it's just been a while since I had a good time going on a date. Getting inside, my phone started ringing and I looked at see it was a first officer I worked with often. Pressing talk, I pulled off my tie.

"Talk to me Engh."

"Good. You picked up. One of the Captains dropped out at the last minute. Can you fill in from Kennedy?"

"When's the plane take off?"

"A few hours."

"I'll be there. Sit tight."

Ending the call, I sighed, kicked into gear to pack up everything, change and check out. Captain's hat on my head, I made sure everything was in my pockets or in my small bag then rushed off. The last drive through the city was relaxing as I dropped off the rental, tipped the attendant, and went to check in with the crew. Meeting Engh, we fist bumped and he caught me up to speed.

"Who was the dropout?"

"Wendell. Claimed he had food poisoning but someone saw him hitting a casino. Boss is talking to him now."

"Guess I was the closest."

"No. I just trust you over anyone. Have you had a drink lately?"

I thought for a bit and remembered I had a drink or two with Kai. Though it's been over four hours and I'd had tons of water.

"Should be fine. Straw me if you like."

"Nah. I trust you. Let's get preflight done before we board."

Nodding, we headed to maintenance and assessed everything from year make to model, last inspection, and any repairs. Checking the manifest, I saw that there were celebrities aboard, so had to keep a low profile. Checking the destination, I saw we'd be switching timezones to London then to Germany. It wasn't anything I couldn't handle, just wished I could stop at home for a bit. Grabbing a last minute snack, I added an espresso hot chocolate, one that the late night staff get right, to it.

Thanking them, I sat at a small table with my cream cheese bagel to enjoy the last minutes on the ground. On cue, Engh flagged me down to board for more prep. With more prechecks, passengers boarded and I was there to greet them. A lot of them were surprised I fit in the plane, which I get a lot. A lot of looks and winks, making me shake my head inside. Making the announcements before take off, I heard the normal groans from passengers about the slight delay and the crew having a chuckle to themselves.

Turning on the tarmac then down the runway, I went into the same zone I always seem to. Relaxed, calm, and focused. While I left into the night, I sipped a warm tea and saw the sun come over the clouds. Some things you see here can never stop being amazing... especially a sight of sunrise up close. At times like this, I don't find fault in the choices I made in life. Do I have things I regret? Of course I do. Every man does. Do I still have dreams in my 40s? Always. You should never stop having them.

Finding them is a bit harder. In the sky seems to be a good place to start.

* * * * *

From my night with Kai to 4 months later, work hasn't left much room for a personal life. I got some nice resting and relaxing in my own bed after what seemed like a long time away. The local shopkeeper thought I'd gotten ill from not being there a while. I met with some old friends I'd made in Galway, Dublin, and Belfast, who happily picked my brain on who I'd been dating or if I took any pictures at new places on my travels. I gladly visited an area with a lot of pets to see more happy faces and think more on if I should get a cat or dog.

On and off, Kai and I would talk on the phone. Though texting was how we talked more often than not. I had to learn to be a fast texter and use my thumbs and not just one finger. I have gotten better at typing with one hand with the phone lying flat. He showed me some outfits he'd gotten from shows or designs he had to choose for the runway. The pictures were innocent but how he posed for some of them made me use them for... other reasons. Corny as it is, Kai looked good and what he sent made me cum.

Despite the pictures I sent, he admitted how he'd done the same, especially after a workout in clean clothes. Or in a dressed down uniform during a layover or two. On an off week, yah fucking hoo, Kai was in Italy while I was back home. We had enough of a gap in the night for a phone call this time, me going around my flat with a book and he was pacing his hotel room with a view.

"What's the night sky like over there?"

"Clear with a bunch of stars. Wish you were here to see it with me."

"I'm piloting a flight to Milan day after tomorrow. Maybe you'll be on the flight from Milan to Morocco."

"I just might be. Hope I can hold my nerves until then."

Knowing I could see Kai made me wiggle my toes, and my cock burned a tad. Playing it off, I made a dirty joke.

"I sensed a disturbance in the worm force... Your message has been received."

Giggling madly, Kai answered shyly once he calmed down.

"Sometimes I hate how you know what I can feel..."

"Feelings are mutual when both of us have them."

"...Caleb?"

"Yeah Kai?"

"Have you, ever uh... had- Nevermind... It's... silly."

"No no. Tell me sweetie. What's on your mind?"

"Have you ever had phone sex?"

I paused, thinking if I actually had anytime recently before we met. But I couldn't recall.

"I probably have at some point. But not recently since we met. Have you?"

"Once or twice. I'm bad at talking dirty. That's what Peyton used to say."

"Forget about him. You have me now Kai."

That pause held a while... as if he were trying to ask something but not knowing what to say.

"Can... you?"

"Can I what sweetie? You gotta help me out."

"Phone fuck me... I know we've met once, and we're trying to be slow... But I haven't shook the feeling of your kiss the whole time."

Feeling a kiss is one thing... wanting more to go by... was something we both wanted. This being the closest for a while, why deny our lust?

"Since you asked so nicely, I have no problem saying yes."

"God, hearing you say yes got me hard..."

"You and me both Kai."

I sighed, both discomfort and horniness setting in. Even my hand brushing through my jeans felt intense.

"How... do we start exactly?"

"Been a while since I've done this. But I know we need a toy each. Do you have one?"

"I should."

"Lube to go with that?"

"No."

"That's alright. We'll remember that for next time yeah?"

"Of course hehe... Mind if we play a fantasy this time?"

"Will that make you comfortable?"

"Kind of... lets me get relaxed."

"I get you."

We chatted more as our short notice list was checked off and we rummaged for what was needed. I had a stroker, which stood at home while I traveled, and a bit of lube for more 'chill' factor as you sped up. Sure that neither of us needed anything, we relaxed and started.

Our theme: A dark club in red lights. I looked mean and solitary by myself near the bar. Kai walked over, shades of red highlighting him, and we found a quiet spot to speak in each other's ear.

"Loud place like this doesn't fit you big guy."

"I can say the same for you. Who'd leave you all alone?"

"Takes a bit to handle me. You might know nothing about that."

"Bold of you to say that since you just met me."

"People earn my time. And I'm not cheap."

"Anyone worth my time better give me something good. Or else, this conversation is over."

"There's a quiet room around here. Guess I should show you what I have."

As our scene changed to that quiet room, Kai sighed and groaned, overexcited by just what we heard. As I rubbed a bit of lube on the tip of my hard cock, the precum made me drip more as I grabbed my stroker.

"Hope you're not leading me on sweetie."

"If you fuck me right... I won't have to on our second date."

"Pretty sure you're a tease sweetheart... Even if you are, I'll set you right."

* * * * *

In that moment, our brains synced, both breathing hard as the stroker slipped over my tip and his toy likely teased at the rim and slight inside of his ass. I bit my tongue to not moan aloud, the chance to tease with that isn't here yet. Despite the heat in my body, I remembered I had someone else waiting.

"For such a smart aleck, you like someone putting you in place."

"How would I lure you from across the room otherwise daddy?"

Hearing Kai murmur 'Daddy' made me shiver. So much that my hand slipped and made the stroker slip farther down. Grinding my teeth, I nearly let him on to how what he said was working. Getting back in my head, I chuckled a bit before answering.

"Mmm aren't you a sweet baby? Want more?"

"Yes daddy... So much more."

"What's the magic word sweetie? C'mon you know it."

"Please..."

"That's my baby. I'll remember to tie you up. That way, you can't run off until I'm done."

"Keep me..."

Even with my eyes closed, I grinned and didn't need prompting to move the stroker in a certain way. Letting my groans, moans, and hand fuel me, I in turn heard the same from Kai. In the background, there was a slight buzzing sound and the bed frame creaking. Thrusting faster, my breath made him get louder, the buzzing more intense, the creaking more noticeable. An almost whimper grazed my ear as Kai spoke up.

"Daddy... please... I need your cum."

"Shh shh. Be patient. You can't have it just yet."

"I can't take it. I'm gonna... fuck... I'm dripping. Give me your cum."

"Shh that's no way to ask. Only good baby boys get cum if they know how to wait."

He sounded as if he'd cry but turned it to a near growl. Voice and groans muffled into something to concentrate on listening to what I'd said. What felt like hours packed into a few minutes, I felt myself shaking, sweatpants popping past my knees as I felt ready to cum. The shakes even trailed into my voice.

"Think you waited long enough?"

"Yes, god please Daddy. I'm dripping everywhere..."

"Alright then. You better keep it all inside."

Not holding back, Kai heard me moan and groan, nearly screaming as I came, him doing the same as I heard him roll on the bed a bit, some creaking, and sighing into the pillows most likely. Feeling finished, I slipped the stroker off, still a lot of cum, lube, and mess dripping down my shaft and balls. Still panting, I spoke soft into the phone.

"Still with me stranger?"

"How could I not be? I'm lighting up the room with my afterglow."

"Hehe glad to hear. Can't wait to do it again so I remember it."

"I won't say no to that offer."

"You'll be able to feel me for real this time."

"Mmm wouldn't say this was bad for phone fucking... Your voice was definitely hypnotic Caleb."

"So was yours Kai. Pretty sure I need a second shower."

"I might... actually need to call for fresh sheets. Seems I enjoyed myself a little too much."

"There's no such thing when you're in the heat of the moment. If it costs anything to change the sheets, I'll pay you back."

He let out a soft giggle, making me smile from ear to ear.

"I think you've given me enough Daddy."

"Still. It's a courtesy."

"You're too good to me. And we're not even in the same room.... I'm sorry we aren't."

"I can say the same sweetheart. Comes with the work. And I can't ask you to just quit."

"You'd be the first to not want me to quit and be a house husband. Or a live in friend with benefits."

"Tempting. But that would mean nothing if you weren't happy."

"Not many people consider being happy compared to being attractive, compatible, or being comfortable. I feel sometimes that the older we get, people stop caring. Not in a good way but in a way that makes it harder to keep friends... date, or even feel that we'd know them in passing. Like everyone's closed their heart and focused on boasting their ego or life."

"It's little things that build up big things. Without a foundation of them, you might not move past the basement to even be on the first floor."

"I'm sorry if I ruined the mood with a strong statement or-"

"Baby, no worries. It's not just about being sexy. I love pillow talk and serious conversations, even after fucking."

"God, why are you perfect?"

"If I were a millionaire, had a huge dick, and shrunk a little, I might be perfect hehe."

"You don't need any of those things. And you've showed me a picture of your cock. Probably the prettiest one I've had the pleasure of seeing."