AN: This story came to me from a friend about his real life experience. I'll admit I embellished a bit but a large chunk of this story is true. Enjoy!
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So, I'm a pretty submissive guy and get occasional 'dares' or 'challenges' from friends online. They've been pretty harmless and easy to accomplish in the past and mostly involved me doing something a bit embarrassing at home.
The last one though, was the first time it had me taking a challenge on the road. Or, in this case, in the air.
I mentioned on my blog that I'd be traveling for the first time in over a year and was excited to visit friends out West. The next day, I had an anon request saying that I should fly without underwear.
Honestly, the thought kind of excited me. I don't tend to go commando and so the little nudge to do something outside of my usual routine was nice. I posted their request with affirmation that I'd take on the challenge. The rest of the day was spent packing and preparing for the trip.
The next morning I decided to check my page one more time before heading to the airport and, wow, some guys really liked the idea of me traveling sans-underwear. I had no idea being commando was such a turn on for some guys, although when I stopped to think about it, I found myself thinking the same thing.
In the thread among my online friends and fans though, guys kept trying to add to the challenge. That, "just going commando wasn't enough." "A ton of guys do it, and with jeans you can't even tell." "That's not hard enough."
They did have a point. I took a quick once-over at myself in the mirror and my jeans and t-shirt. The jeans were in fact dark and thick enough that you really couldn't tell if I was wearing underwear, no underwear, or even a few pairs to be honest.
Returning to the thread, I saw a few suggestions of how to up the ante, so-to-speak. One dude recommended just going bottomless which obviously wasn't going to happen. Another said I should wear those leggings girls buy that show off their asses. I didn't own any leggings like that in the first place but I knew I couldn't have the balls to wear something tight like that anyway.
It wasn't until I read one guy's suggestion on just wearing some loose gym shorts that piqued my interest. He said he loves to wear loose gray shorts out and about. It gives some definition to his cock if people are staring but if you're not actively seeking it out, most people won't notice.
That seemed like a reasonable challenge and definitely outside my comfort zone but within the realm of 'willing to try.'
I went back to my dresser to find a pair of blue shorts that I've had for a while and held them up. They were a thin nylon material but also dark, unlike the gray shorts the dude who commented talked about. I thought that would be better for me anyway, as I didn't really want anyone to see my junk.
I stepped out of the jeans and boxer briefs I had previously decided on and pulled the shorts up my thighs. Looking back in the mirror I felt pretty good about the challenge. I mean, without my boxer briefs to contain my stuff, you could see my cockhead push against the material a bit.
They had these tiny holes throughout the fabric but I couldn't actually see my skin through them so I knew it would be fine.
Stowing the jeans and undies into my suitcase instead, I headed to the airport while the sun began to rise.
Arriving at the airport I was already starting to get nervous. The confidence I had about this funny and stupid challenge was becoming a rising fear. I found myself playing through all the ways this could go wrong from probable to insane.
What if the escalator ate my shorts off my body? What if someone spilled something on me and I had to change? What if they had to do a body search on me?
The thoughts were mostly terrifying but a bit of a nervous turn on. The bumpy drive to the airport didn't help the realization that I had gotten hard during these thoughts. I looked down to my lap as I parked and gasped as I saw my hard dick pressed up against the shorts.
Even in the dimly-lit airport parking deck I could make out the entire shape of my dick straining against the material.
"Fuck..." I whispered to myself.
I thought about bailing on the challenge, but that would have been a first for me. Instead, I took a breath. I willed my boner to go down over a few minutes and just decided that I'd need to not repeat that until I safely arrived in my hotel a few hours from now.
Looking back at my now-soft package, I was reassured by it's obfuscation. Did I certainly have a dick between my legs? Yes. But you had to be looking.
With that, I got out and headed into the airport with my suitcase behind me. Little did I know how badly I should have just bailed on this whole thing...
Check-in was pretty uneventful. I felt like people were staring but honestly that was more in my head than anything else. Also, no one wants to be at the airport, especially not early in the morning. I handed my bag over to the front desk lady and took my ticket, phone, wallet, and book for the ride along to TSA.
This is where the nerves started to bubble up again. What if they had to search me? I was pretty confident that wouldn't happen since I only had shorts and a t-shirt on and no bag, but my mind was jumping to the worst case scenario.
As I got in line for security check-in, I got frustrated with the pre-check people. Their line was so short while I was stuck here behind at least a hundred people. There was one guy, sort of young and a little cute who seemed to be checking me out. When he caught me looking at him, he gave a little smirk. Okay, he was definitely checking me out.
I started to feel a familiar lust tingle traveling down my spine and quickly looked down to my shorts. The good news, I wasn't hard and would not be getting hard anytime soon because the bad news: my shorts were more transparent than I thought.
In my dim-lit apartment and in the car earlier I couldn't make out any detail of my skin underneath; however, in the bright fluorescent light of the airport that was very different. Between the blue fabric was dotted with the color of my skin peeking through all those little holes. And with the all-around lighting of the airport, the outline of my cock, especially the head, was pretty fucking visible.
Panic had set in, but I had no options. I was stupid enough to not take a bag with me with any other clothes and my clothes and keys were in my suitcase, checked and already heading towards the plane. I literally had no options but to continue onward.
Fuck me.