The Free-baller in the Airport

A bit about the story... One of the best things I have found about becoming an author is making friends with readers and especially with fellow authors. One of those friendships began early in my writing "career" and that was with "trappedinthecl0set". I read his work and was hooked and he agreed to help me with editing. It was during a series of late night joint editing sessions we became good friends. Well this story came from those late night, frisky conversations. Basically what if in some alternate universe we met, at an airport... this is the story that came from that. I won't give anything away with this, but this is honestly a story of what if he and I met up and life was a bit different for both of us, but at the core we were the same people. I hope you, and he, will enjoy this story. Much love to you, my dear sweet friend.

This story is ours, so don't be a dick. I would really appreciate if you take a minute to let us know what you think of this story, it took several months to come together and I think it is some of my best work so far. Let me know.

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As if this fucking week couldn't get any worse. I had been forced into taking a meeting by a client that I knew was going to be nothing but a waste of time, causing me to have to take two flights just to get to Salt Lake City and now, sitting here in the airport at Wasatch Brewing in terminal B waiting for the airline app to update so I can find out where and when my flight was finally going to board. It seems the aircraft that was meant for us was rerouted, and we were delayed and now stuck.

I typically like for my Fridays to be spent at home, catching up on work so I can slide into the weekend and really kick back and relax. I wanted to get home to New Orleans where I would try my best to pick up the pieces to my life that have been left in shambles. My wife and I finally called it quits after 10 years of not the greatest marriage. We were, at best, friends, and never good or really settled in to being husband and wife. There was never any spark but both of us felt pressure from family and friends to tie the knot finally. At the time, we were both in our early 30s and still single. We knew better, we fucking knew better. We loved each other, we were just never "in love."

So now I was single, I kept the house as she took a job out of state. I was headed home to a big house and my 1-year-old Great Dane, Mufassa. When I traveled, my assistant stayed at the house. Ethan was great and he was incredibly good at what he does, frankly, he was more put together than I was at this stage in my life, and fuck he was only 20.

I order my second beer, this time opting for "Island Hop" which they say is a fruity IPA and I break down and order a sandwich as well, as it seems I am not going to make it out of here in the next hour at least. Airlines run smoothly when they can keep things in motion, when one of their aircrafts is pulled from service, well that sends cascading repercussions and I fear we are not the highest priority right now.

Given the delay, the Brewery started filling up, and they sat me at a table for two and I had my back against the wall which allowed me to participate in one of my favorite pastimes; people watching. Capturing way too much of my attention was this really loud blond who is reading her husband, I assume, the riot act as if he caused the jet to have mechanical issues and get re-routed. I have never been more excited to see her storm out of the bar and her whipped husband follow her with his tail between his legs. "Happy weekend", you two! I said under my breath.

At this point, the two bar stools that they were sitting at open up and in comes this young guy, no more than 24 I would guess. He caught my eye because, well, he had a noticeable cock swinging inside his sheer gray basketball shorts. You know how when you catch something out of the corner of your eye and your brain says, "Hey, something is up, check it out!" Yah, that is exactly what happened here. My brain said, there is something swinging there where normally you wouldn't see anything swinging. As he turned around to get ready to hop onto the bar stool, wow I thought, this dude couldn't be wearing any underwear! A smooth, bubble butt with no underwear line at all and no sign of any sort of boxers or even a liner in the shorts.

"Wow, bold move their young padawan" I think to myself. Wow, to be young and carefree again. Seemingly no cares in the world, at least not enough to bother with underwear! And in such a conservative city and state! Bravo.

My next beer comes out, and it's a bit sweeter than I care for, but it is nice, and frankly, anything with alcohol in it will do the trick right now. My phone buzzes and informs me that the new departure time is going to be in just under 2 hours and that we will be at gate B1 which is right here, so literally no rush for me. But bad news, I have a seat change. As I pull up the app on my phone, I see that we are on a different type of jet, and there is a smaller first class on this flight to Chicago, and I guess since I was upgraded, that didn't stick. Well at least I will get out this afternoon, and I have every chance to get a flight from Chicago to New Orleans yet today. Home in my own bed tonight, the plan is back on.

I text Ethan to let him know the plans, he quickly responds with an "OK Boss" and shoots me a picture of Mufassa. I can't wait. I play with the app a bit more and rebook myself on the flight out of O'Hare at 7 pm to New Orleans; even if we are running late, I will be fine. Ethan can pick me up at MSY just after ten and my weekend is back on track.

After playing with his phone, 'free-baller' (I mean the name may be vulgar but seems appropriate) turns his bar stool a bit so he can watch a baseball game on the TV. Again, my eyes are drawn to his crotch because I can see his dick, clear as day. It's as if he was sitting there without anything on at all. Dang, I don't think I was ever this bold. This time though, with his attention on the TV, I can check him out a bit. He seems younger than I thought, deep piercing dark eyes, almost looking like they are black. He has a devilish smile which you can tell he has been through some stuff in his life, and is wearing an older, maybe vintage Atlanta Braves t-shirt. As he reaches for a napkin on the bar, exposes his stomach a bit showing he has a bit of hair on his stomach. This has me checking him out more and as I do he catches me watching him. I quickly refocus my gaze to my phone fumbling to scroll through my twitter feed in hopes he doesn't think I am some sort of pervert.

After what I feel is an acceptable amount of time, I look back up again and 'freeballer' is staring at me and just a grin on his face. Wow, are we flirting? Surely not, I mean what could this hot guy be thinking about a 42-year-old, sitting in jeans and a polo shirt, likely with 20 COVID pounds left to shake. Clearly that is not it. I give him the straight guy "what's up" nod and go back to my phone just as my food arrives.

I suppose I should give myself more credit. Being in a sexless marriage for the past decade has kinda sucked the soul right out of me and just now I am trying to get my groove back. At 5'11 and 190#'s I certainly had some toning I needed to do but I am quite sure if you look up "dad bod" you would see a photo of me. Im rocking a 34" waist, sure it needs to get back to 32" but fuck it. I've got good hair, nice teeth, and near perfect skin. Deep blue eyes that when needed used to be able to get me anything I wanted... and should it ever get to sex, I have a nice 7-7.5" cut thick tool to work with. Fuck right, I am the entire package damn it!

I suppose that brings up the next question. I was married to a woman for 10 years, aren't you straight? Well that has not always been clear to me, frankly. During my college days I fully accepted being bi. I tended to enjoy having sex with guys more, that is for sure, but I always saw myself in relationship with a woman. Perhaps though that was programming, or just because the guys I tend to meet, well they were not really relationship material. But that was all in my distant past and frankly right now I don't know what I was looking for, or what the hell I was doing.

The food was fine, but typical to airport food it was nothing like you could get in New Orleans at nearly any small mom and pop shop on the corner of nearly any street. We are certainly spoiled. This weekend I had hoped to make my way to Cochon's or possibly Dragos as I have been traveling nearly solid for the last two weeks and I needed a taste of home. I texted with a few of my friends, a gay couple Sam and Pete and asked them if we were still on for Dinner Saturday. They were good guys and they really leaned in to supporting me and what I was going through.

Apparently, someone scored in the baseball game that was on the TV because folks cheered and a few jeered. I have never been one for any of the sportsball, except of course the Saints because that is required for residence in the City that Care Forgot, birthplace of Jazz, the Big Easy. As the crowd cheered I locked eyes again with 'freeballer' and damn I was drawn to this guy. I guess it could be his perfect ass or his cock that is clearly wanting to be seen in those shorts.

I saw as 'free baller' stands up after he pays his bill and then he heads out. Best part is I get to see that fine ass again. He has two perfect cheeks that seem to have their own gravitational pull to them. They move in perfect motion and just beg for someone's hands to be cupping them, massaging them, clapping them. Damn, I am quite sure even though I just ate, I could make a meal out of that ass.

"OK, focus Logan, can't be throwing wood in an airport!" I say to myself and I hail the waiter for my ticket.

I had enabled the alerts to come to my phone and the jet we would be boarding shortly just arrived at the gate and so before long we should be boarding and on my way home. After paying, I head over to the gate as I am ready to go.

Never before have I been happier that I only brought this small carryon and my briefcase, this way I won't have to gate check any bags and when we arrive in Chicago I can just make it directly to the bar for another drink before catching my connection to New Orleans.

Well there he is again, freeballer is apparently on my flight to Chicago. As he leans up against one of the pillars holding up the roof and scrolls his phone it provides me yet another opportunity to check out the VPL (that's Visible Penis Line, just in case. I may be old, but I try to keep up). I just can't believe that he wore shorts this thin with no underwear. Did he do this on purpose, or was it just a happy accident? I am not noticing the head print coming through so holy shit, maybe he is uncut. Fuck, I have always wanted to play with an in-tact guy. Shit, I can NOT bone up in these jeans as everyone here will be able to see it. First pair of tight jeans I have possessed in quite some time and while I know I look good in them, shit my bulge is already substantial in these. Soft, I am not much to scream about, but I have huge nuts and so they make for an ample package no matter what underwear I am wearing. Newly single Logan now wears sexy underwear that lifts up your cock and balls and thrusts them forward.

I got an alert that my seat has changed again, this time they moved me up into premium economy right behind the smaller first class section and I got my aisle seat back. Sitting in a window seat is too claustrophobic for me, so this is much better. I am surprised they didn't find me a seat in first class, I have been carrying a United Visa black card for nearly 10 years. I am assuming the ones that got the seats were all paying full freight on their tickets.

Soon we are boarding and when they call for the elite statuses to board, I hold back. I don't need the overhead space for my small bags and I would rather not play back and forth with someone needing to get into the window seat. It will already be cramped enough, I'd rather not add the slow dancing of seat shuffling to the agenda. Scrolling my phone I see Freballer get into the boarding line and head down the jetway and I decide to follow, a few more glances at his fine ass won't hurt anyone and may add to my nearly depleted spank bank.

I make it onto the jet bridge and get to watch him some more, which is so much fun. Damn he has a great ass. I would love to use those cheeks as pillows or better yet, peel them open and slide 7 1/2 inches deep inside him.

I lose sight of him as he makes his way onto the jet thinking I have lost him to the belly of the plane, make my way onto the jet and move my way back until I get to my seat and boom, he is sitting in my row, window seat. Holy shit. Having a small space above my seat I throw my small overnight back up top and slide my small briefcase in as well and close the overhead bin having used every single inch of space. I go to sit down in the seat and I notice that he hasn't lowered the armrest between the seats and he is busy on the phone talking with someone as he watches out the window at the ground crew loading up the luggage.

I slide into my seat and buckle up, scrolling through my phone one last time. Shooting Ethan a quick text:

Me: "Boarded the replacement jet, should be airborne shortly. Off to Chicago!"

Ethan: "Sounds good boss, let me know if you need anything. You have wifi on this flight right?"

Me: "Stickers say we will, so fingers crossed."

Ethan: "K"

I flick over to the airline app and I see that we have been updated and should be landing 10 minutes earlier than we were supposed to so they are making up for some of the lost time. Plenty of time to make the shuffle through O'Hare. The best news is the arrival gate is very close to my departure gate and there is a bar in between the two.

He hangs up his phone and starts to stow his phone and looks over and sees me.

"Oh, hi! I didn't realize... I am sorry if I was too loud on the phone." His voice is softer, but still manly, generally showing he was sorry, you could hear that in the tone. Wow, a nice guy, you don't see many of those lately.

"Not a problem at all. We all have been juggling today, just glad we are getting out and that I should get home tonight." I say, being a bit more talkative than normal on these flights.

"Cool, umm... you live in Chicago?" he says, clearly wanting the conversation to continue or out of nerves I really can't tell.

"Oh no, I have to connect. I live in New Orleans. Are you headed home or going on an adventure?"

"Ah, an adventure, really. Meeting up with some friends, going camping and going to see some games." He says, clearly lighting up a bit. I ask some probing questions about his friends, what they plan on doing and what sorts of sports he likes. Both of us relax a bit in our chatting as the flight crew goes into their presentation and their cabin checks.

The seats are rather small and while we are talking with each other, our knees and legs keep touching each other. When I first noticed this I jerked away really quickly, clearly the long-engrained programming in me to not physically touch another man like that. But the seats are so damn small, this is bound to happen and so when he didn't pull back this next time, I didn't either and so our legs to knees were touching, and I am sitting here wishing that I would have worn shorts. Our arms were touching as well, since neither of us had pulled down the armrest between us our arms were sorta free floating and landing in our laps. His skin was warm and he had a light dusting of darker hair on his legs and on his arm which I found extremely sexy.

As we kept talking, several times he reached down to re-arrange his junk in his sorts, fuck it was hot to see him do that, and apparently, I had no qualms just watching and focusing on him doing it too.

Finally, I couldn't help myself and I said "Hey, I really like those shorts! They must be super comfortable!"

He smiled really big and said, "They really are, they are super soft, here feel this" and he took my hand and placed it on his cloth covered thigh and moved it back and forth a bit bringing my hand up shockingly close to his junk.

"Wow... they are... wow... they are super soft, I will have to get me a pair, though I don't know if I would be brave enough to wear them out in public, well done you!"

"I like how freeing they are, I also like the looks I get when I don't wear any underwear beneath them." He says with a quick wink at me. Well, if I had any doubts that this guy was flirting with me, I think those have all evaporated... now is my turn to blush.

Airborn, we keep talking about nothing really, and everything. I shared with him what I do for work, he shared with me what he likes to do in his freetime and that he was working on becoming more serious about life and career as he shared he was 22 years old and not completely sure where the future was taking him. I in turn shared with him that I too was on a bit of a discovery mission as I had just divorced a woman and now trying to find myself after I tried to live my life to make everyone but me happy.

He leaned over at that point and offered his hand, "My name is Scott by the way," he said and his hands were so very soft, warm and shot a bold of electricity through me.

"I'm Logan," I say, "It is really a pleasure to meet you Scott! Turns out I guess I am old enough to be your father! Yikes!" I say to him ultimately confessing that I had just turned 42 a few months earlier in May.

"Well, Logan, if it is any consolation I spend almost all my time with slightly older people, like you. I find kids in their 20s to be so boring and aggravatingly predictable." Well I certainly understand where he is coming from there, but wow, for 22 this guy was rather impressive.

"From the cockpit, this is your captain speaking. Folks I am not going to sugar coat this for you but we are having some mechanical problems and while I am nearly sure it is just some malfunctioning gauges here in the instrument panel, I don't want to risk it and so we will be making an emergency landing in Lincoln Nebraska and it looks like we may be staying the night there due to this. I am sorry, but my main goal here is getting everyone safely to their destinations and to do that, I wanna have these checked out before we continue our way. If you need to use the restroom, please do so now as we will be making our initial descent into Lincoln in about 10 minutes." The number of sighs and "oh no!" and other remarks was a lot.

Having been through this 100 times before I immediately text Ethan -

Me: Find me the nicest hotel room possible in Lincoln Nebraska for the night,

Me: appears we are re-routing due to mechanical issues.

Ethan: On it boss

Ethan: Wow, not much available, working

Me: Grab anything then

Ethan: Boss, best I could find, ONLY I could find is booked

Ethan: Embassy Suites, downtown, should be fine

Ethan: Appears their is some sort of sports game or something

Ethan: You are booked and pre-paid

Me: Better than nothing, thanks E

"Well this sucks," Scott says.

"Yeah, it really does!" I say as I set down my phone, at least knowing I will be able to take a hot shower tonight, maybe have a nice meal and get a decent bit of sleep.

"Looks like we will be sleeping in their airport tonight, fuck!" Scott says.

"I just asked my assistant since he is on the ground to find me a hotel room, so I am super glad we found one. We still have WiFi if you wanna search for one, though Ethan did tell me that there was some sort of sports thing happening in Lincoln and so there were no rooms available."

"Good idea, but damn I won't want to blow my money on a hotel room here when I am supposed to be using this money on my vacation."