The Underwear Booth (Patreon)

Some days I just sit in front of my laptop, watching the cursor blink on an empty word document, and some days, I see some inspiration that has me bust out a story in one go. Today was the latter... Check out the Discord for the photo that started all of this

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Dragged into the street festival by a friend, it took me a while to feel myself relax. I'd come out late in life, and being in primarily gay spaces still felt like a novelty to me. Here, right in the middle of the roped off block, sexy men walked around wearing barely anything at all, and one guy was even clad in just a jockstrap. They probably all lived at the gym and ate nothing but grilled chicken and broccoli, but that was just the jealousy talking.

As the beer kept being replenished in my cup, I loosened up a bit and felt myself even swaying to the music piped through speakers way too close to the action. Passing by one booth selling underwear modeled by sexy men right there at the front, my friend asked me to stop.

“Rick, they do not have our size here- why would we look?”

He didn't respond at first so I just assumed he couldn't hear me over the aforementioned extremely loud music. As we walked up, he stepped behind me for some reason, and I didn't realize why until he'd already lifted my shirt up to my neck. I tried to move, but I didn't want to spill my beer on the table in front of us so I was stuck.

“My friend here doesn't think that you have anything his size, so I thought I'd ask for him.”

The young guy running the booth had to be half my age and size, but he looked at me as if I was one of the models wandering around today.

“C'mon stud, only one way to find out. Let's drop those pants and see what the tag on that waistband says.”

There was no way that I could ever do this, no way that even in my fantasies I'd be stripping off on the street, but my hands somehow worked themselves down to my waistband. As if my brain had been taken over by someone else, I had my jeans around my ankles in seconds as the man walked around behind me. Instead of simply just looking at the tag, he pulled my boxer briefs below my ass and knelt down to look. I could feel his breath on my skin as he spoke.

“What were you even worried about? Of course, we have this size.” Standing back up, he walked back to the table and started sorting through the various stacks before lifting up a red pair of briefs that looked like they could only fit a doll. As I picked them up, no one but the crowd of men starting to form behind me realized that my ass was still hanging out.

“How about we cut you a deal? We’ll give you this pair for free right now if you act as one of our models. You keep walking around the festival with your friend, but whenever someone asks where you got your new outfit, you point towards our booth. Deal?”

“But how would they see them under my jea- oh…”

The guy just smirked at me as if he could see the gears turning in my head. They hadn’t reached a conclusion yet before my mouth opened up to talk.

“Do you have a dressing room here?”

“Nope- you can change right here.”

And then, I did. My brain was yelling at me to stop, but I was already pulling my jeans over my boots and handing them to my friend who took them without a word. He took my underwear too after I took it off with shaking hands. I hadn’t realized that I’d actually done it until the fabric was pulled over my shoes.

The man hadn’t said anything about taking off my shirt, but it just seemed weird to keep it on now. One of the sexy models with oil covered muscles started to lift that off of me, and I just raised my arms above my head to let him. I was now standing here completely naked with two competing emotions waging a battle inside of me. My brain was trying to yell logic at me, but the feeling of ecstasy running through my veins shut him down. Not even the goosebumps forming on my arms despite the warm day could stop me. I should have let the embarrassment win, but I just needed to do this. I’m not sure if it was to build my confidence, or just some item that I needed to cross off of an internal checklist, but I couldn’t run now.

Taking the gifted underwear, I felt the soft material between my fingers before pulling it on. I was still worried that they wouldn’t fit, that this was just some cruel joke that they pulled on bigger guys, but the fabric effortlessly glided up my meaty thighs. There was barely enough room for my growing bulge up front, but I think that was true for any of their sizes.

There was a mirror in the corner, and as I stepped in front of it, I had to put my hand over my mouth to mask my gasp as I saw myself. There was so much skin showing, more than anyone had seen outside of my bedroom before. The red fabric was garishly wrapped over my bulge, and it had so much stretch to it that it looked like my cock was hanging free. Turning to the side, it stuck out in front of me like a sign daring guys to look my way, but I felt powerful.

“Oh my god, my ass is out!”

That shouldn’t have been the feature that surprised me the most, but as I turned around, I saw in my reflection a cutout in the back that exposed every inch of my crack. I could be walking around and giving a show to everyone, and I wouldn’t even know that they were staring. This was almost too much for me, and as I looked up, my cheeks (at least the ones on my face) were starting to turn the same color as the only bit of clothing that I was wearing.

The initial rush of adrenaline was starting to wear off now, and I wondered if I could do this. How would I walk out of here like this? Turning to my friend for some logic, I saw him zipping up his bookbag with my clothes in it, and I knew that he wouldn’t let me get those back. I was stuck here, and everyone had figured that out but me. Clenching my fists and pulling air into my lungs before speaking again, I realized that there was actually nothing to say. Returning the salesman’s smile as best as I could under the circumstances, I grabbed my drink again and stepped back into the sunshine.

I didn’t know what laid ahead of me for the rest of the day, but I just knew that I had to start walking now or I never would.