Andrew smiled at me as he held up two pairs of skimpy speedos, one for each of us. "So we've got to wear these," he said. "That's the condition they've laid down."
My jaw pretty much hit the floor. "Are you
serious
?" I asked. "No fucking way am I wearing a fucking speedo dude! That shit's fucking gay."
I'd been so into the idea of going round to Andrew's house for this pool party. He'd convinced a couple of girls he knew to come along too, and had assured me that they were both seriously hot and there'd be a chance for me to get some sweet pussy. How could I refuse?
"They said that since they'll be wearing bikinis the guys would have to wear speedos. I'm sure it'll be cool dude, it's just a funny idea they've thought up." He handed me the blue one and kept the red for himself. I looked at the thin shiny material in my hands and shook my head. There was just no way...
"But we'll look like total idiots in these things!" I complained. "They're so dorky and lame."
Andrew sighed. "Look, Simon, there's two smoking hot girls downstairs in their bikinis. If you want to argue about this up here all afternoon then you can do it alone."
He took off his shirt and started to unbuckle his belt. I was panicking on the inside, but couldn't really fault his logic - I did want to get laid after all. I was eighteen and still a virgin; it was getting embarrassing. Andrew had several girlfriends over the years, and I'd never even had one - spending my time jerking off alone in my bedroom all day thinking about hot girls with big tits instead. I took off my own shirt and watched as Andrew turned around to remove his jeans and jockeys and slid on his red speedo.
"Hey, they fit pretty well!" he said, smirking as he turned around to face me. I tried to hide my surprise as best I could, but I was genuinely shocked at the size of the bulge in Andrew's speedo. It looked enormous! I began to regret coming to his stupid pool party in the first place.
"Uh... well, yeah I guess they're a good fit," I said, stammering. Trying not to stare at the outline of his obviously very large cock and balls.
"Hurry up and get yours on," he said now, turning to check himself out in the mirror.
"Okay okay..." I struggled out of my jeans and turned around to slide off my jockey shorts, quickly slipping on the speedo and pulling it up around my hips and over my butt. It felt very smooth but really tight as well. I looked down at my own bulge in the front of the speedo and immediately felt a wave of embarrassment flow through me.
"I should wear these more often," Andrew was saying now. "I mean these were made for me." He was still admiring himself in his large bedroom mirror, turning around to look at his profile.
"Um, yeah, they're pretty cool I guess," I muttered distractedly. I was still looking down at my tight, light blue speedo, equal parts embarrassed , jealous and annoyed at just how much smaller my bulge looked compared to Andrew's. I hadn't been aware that he had a big dick, or at least not
that
big.
Frustratingly, and to my shame, my own penis hadn't grown much over the course of puberty and was basically the same size as when I was a little kid - something I didn't exactly like to broadcast. The bulge in my speedo was just a tiny little bump sticking out above my small, tight balls, while Andrew looked to have some serious equipment in his. Frankly, my entire package looked to be around the same size as just one of Andrew's nuts, and standing next to him at the pool, it would be extremely obvious who was packing more. I wondered if anyone would notice.
"You done, dude?" he asked, finally abandoning his reflection and turning to face me.
"Yeah yeah, I'm ready." I said, slowly turning so that we were facing each other. Andrew, smiling, looked down at my crotch and immediately stifled a laugh.
"Oh, dude, sorry, I didn't mean to laugh. I just hadn't... I mean I guess they do show everything, it's just kinda funny." He raised a hand to cover his mouth as he continued smirking.
"What's so funny?" I asked, getting defensive.
"Nothing! I just hadn't expected to see... well,
that
."
I couldn't pretend that I didn't know what he meant, though I hadn't expected him to be so direct. Hell, I hadn't expected us to be wearing tight little speedos and standing together almost naked in his bedroom. I looked down at my pathetic little bulge and winced.
"It's just... it's cold okay, it's cold in here."
"I'm not cold," he said, glancing down at the impressive package in his speedo. I checked him out again and then looked back at myself and made a noise somewhere between a sigh and a whimper. We were both young, handsome, gym fit teenagers, but Andrew happened to have been blessed where it counts (and then some!) while I had an obvious baby dick.
Andrew tilted his head and smiled, "Well, we can't really go down with you looking like this, can we Simon?"
"What do you mean?" I asked, fighting the urge to cover my crotch with my hands.
"We need to make you look a bit more... fuller, if you get what I mean. Like, a
lot
fuller."
"Dude, what are talking about?" I was wildly confused.
"The girls aren't even going to talk to you if we both go down like this," he said, gesturing to my speedo and then to his. "You'll just embarrass us."
"It's not that bad, is it?" I felt ridiculous standing their in the tiny speedos, my buddy openly acknowledging that I had a small dick. He was still trying not to laugh as he continued staring at my crotch.
"Well let's just say speedos aren't a good look for you. But I've got an idea."
I squirmed uncomfortably as Andrew walked over to his dresser and opened the top drawer. He rummaged around for a moment and came back holding a pair of gym socks and, extending his arm, handed them over to me.
"What are these for?" I asked.
Andrew pointed down to my tiny speedo bump. "Just call it frontal enhancement."
"Aw, dude, fuck that! I'm not going to stuff my speedo!" I shouted indignantly.
"Shh! They'll hear you. Seriously, just try it out. I bet it'll work great. It's either that or you go downstairs and say hi looking like this, and you know speedos are basically just a big arrow pointing to your dick, right? Now, what would you rather your dick looked like, big?" he grabbed his bulge and squeezed it, "Or... well..." he gestured to my own bulge, "Small."
"But I'm not
that
small!" I whined.
"Dude, it looks
really
small to me. Sorry, but it does." Andrew looked sympathetic, but I could tell he was privately amused by my situation. I looked at the gym socks. They were white and thick and made out of cotton. Andrew probably wore them when he was doing track or at the gym.
"But, stuffing? Isn't that like, pretty risky? What if the girls find out?"