It was the summer of 2012 and I had just graduated high school. Me and my best friend Miles were enjoying another late summer afternoon at his parents lakehouse, enjoying the perks of having graduated school and being treated like adults by our parents for the first time. My name is Isaac and I was 19. I'm 5'10, 175 pounds with short but shaggy dark brown hair. I was in good shape with lean muscles from playing on the varsity football team for 4 years. I was a 4-time all-district safety but it wasn't like I was some football prodigy. I just developed early, was older than most in my class and haven't grown an inch since 8th grade and probably only put on 15 pounds (at least it was of muscle). And I was incredibly bitter about that.
My best friend Miles was practically the opposite. Still a month from turning 18, we'd been best friends since 6th grade and he was scrawny until our senior year. He was 5'6 at the end of 11th grade but had a growth spurt that summer and came back to school 6 ft tall (something he enjoyed bringing up all the time now that he was taller than me) and about 160 pounds. He had short and curly light brown hair, the kind that's now popular with all the tik tok fuck boys. He always had talent in lacrosse but was never anything special until his physical transformation when he'd suddenly become the best lacrosse player in the state at our small school level and got a scholarship from a small division I school. Another sore spot for me, as I'd received no such offers in football and would be attending the local community college to get my grades up before moving on to university.
Yeah, it seemed in just a years time, miles had come out from under my shadow and seemingly outperformed me in all areas. Don't get me wrong, he's always been a good student, a good athlete, popular with the ladies and really had great charisma. But he was always my sidekick growing up. As a result of his puberty seeming to kick in to high gear late, however, we had become equals. Or so it seemed. Its funny how everything changes as you enter into young adulthood. And this particular summer night is about to change everything for me.
We were having a few beers and blasting Drakes album Take Care that had come out earlier in our senior year. We'd wanted to throw a party to celebrate having graduated the previous week but decided there was just no way to do so without the neighbors calling Miles' parents. So we just sat around the pool, shooting the shit.
"Bro, I think I'm gonna add Miss Gray on Facebook...we aren't her students anymore, and she's only a few years older than us" Miles said to me, talking about the super hot English teacher with the fat ass that all the guys were obsessed with.
"Dude, she's not gonna be interested in you. A chick like her is dating some rich doctor or lawyer around her age. She ain't got time for a little boy like you" I teased him.
"I don't know who you're calling little, short stuff! Ain't nothing little about me anymore" came Miles reply.
Normally, I'd be agitated about him calling me short stuff but it was the second part of what he said that I took notice of. All of the sudden, I felt a curiousness I'd felt a few times over the past year that I quickly pushed out of my head as I always did.
"Quit calling me short bro, you're only a couple inches taller than me and in case you haven't noticed, im still bigger and can beat your ass!" I said back, only half joking.
"Yeah that may be true but I'm bigger where it counts" miles retorted, an extremely odd thing for him to say. Sure, like all horny teenagers, we talked about sex and what we've done with girls but we never talked about our dicks with each other.
I laughed and said "That's so gay man, I'm not trying to talk about your dick!"
Miles paused and just smirked at me before saying "Uh, I was talking about being taller. But it's interesting where your mind went...queer!"
I felt my face get hot and knew I was flushed red. I tried to give a humored smile to hide my embarrasment and said "Whatever dude, we both know what you meant." Miles smirked.
"Nah man, how would I know how big your dick is! We haven't been naked around eachother since freshman year!"
Fuck, i thought. This was true, back when Miles was on the football team (riding the bench, I might add because he was a little guy). And even then, we were in the early stages of puberty. Once again, images I didn't want to think about start going through my mind. I tried to shake it off but it's obvious to me now that I was definitely thinking about Miles in a different way. Ever since he came back looking completely different from his visit to europe the previous summer.
Thoughts of Miles seemed to creep into my mind whenever I was laying down at night to sleep, or when I'd jerk off. I honestly forced myself to not think about why that kept happening throughout our senior year. I was in the strongest denial about having any physical or sexual attraction to him.
"You right, you right. I don't know what I was thinking" I said nonchalantly with a chuckle as if it was funny and not part of a legitimate identity crisis that was going through my head.
"Sure you do, you were thinking about my dick! I don't blame you, I'm hot as fuck" Miles said, wearing a knowing smile.
Once again, I felt myself turning red. And I was also pitching a tent in my bathing suit. Thankfully, we were standing in the shallow end of the pool and he couldn't really see. Curse teenage hormones, I thought to myself. That's all this is. Looking back, my face had probably been a dead giveaway both times that what he was saying was true...but at the time, I was a little shocked at the things he was saying.
"Wha - no - dude! You know I'm not gay bro, shut the fuck up" I replied with genuine frustration. Yet another giveaway I'm sure. I suppose the natural reaction would have been to simply laugh it off.
"Whoa there short guy, I never said anything about you being gay. I mean, it's natural to be curious about how you measure up to the competition."
I normally would have threatened to punch him in the face if he made another smart remark about my height again but at this point, my mind wasn't functioning right.
I hazily responded "I mean, that's true," then saying a little more forcefully, "but I'm not worried about you. I know I got you beat there!"
I thought that was a good retort, thinking I'd just turned the tables on him. However, his response shocked me.
"If you're so confident, why don't we find out?"
I'd always been comfortable with my size, I was 6.5 inches and while I wish I had more girth, I'd never had any complaints. But the truth is, I was a little intimidated by Miles. It was impossible not to notice he had a decent bulge every time he wore sweatpants. So I just said "Ha, yeah right dude. You wish you could get a look at my dick!"
Miles had a totally straight face and with a serious tone, responded "I guess little man is worried about just how little he is compared to me."
This immediately got to me. Good judgement out the window, I said "okay then, let's find out." Subconsciously, I probably really wanted to see his dick but in my mind, I was just being my usual competitive self.
Without another word, miles made his way out the pool and I followed him. My hard-on had thankfully gone down by now but I still had a bit of a semi. Which I figured was a good thing, since I was a grower and not a shower. We dried off and walked inside into the living room.
As soon as we got into his living room, miles turned around and said "Okay, so what's the forfeit for the loser?"
"I don't know man, winners choice? No gay shit though" I answered him.
He flashed the shadow of a smirk and responded "Deal, same time?" as he grabbed his waistband. I nodded my head, and as I did I looked down and saw his bulge for the first time that night. It seemed bigger than I remembered and I all of a sudden felt nervous. Correction: I had butterflies, like some schoolgirl with her crush. Not that I'd thought that at the time.
"On 3 then, 1....2....3" and Miles made like he was going to pull his shorts down. He faked me out. I pulled mine down to my ankles, realized he wasn't pulling his down and went to pull mine back up quickly, rather pissed off. Why had I been so eager to get them down??
Miles laughed and said "wait, I'm going now. I just thought you were tricking me." And he slowly pulled on his bathing suit, not from his waist band but from his thighs. I was watching intently, as my best friend pulled his dick out. Its obvious he did this on purpose for affect, wanting to see my reaction. It seemed to take way too long for his dick to completely pop out and when it did, my jaw dropped slightly. Not in a shocked way, but in an intrigued, slightly confused way. His dick had to be 6 inches soft, about the same as mine would be hard and even thicker than mine is hard.
Immediately, my dick rocked up. It went from staring at my feet, to staring right at Miles. And Miles definitely noticed. He smirked and said in a voice barely above a whisper in a confident but not braggadocious way "I knew you wanted to see it." It sounded almost seductive.
It wasn't in a joking manner but it wasn't accusatory either. It was just matter of fact. It made the hairs on my arms and legs stand. And my face was burning yet again, my eyes unable to look away from his dick. There was no point protesting it, I couldn't find my voice to even if I wanted to. I was embarrassed, I was disappointed...and I was turned on.
Miles said, in the same confident quiet tone, "you know, its rude to stare." This broke me out of my trance and, still unable to look him in the face, I just looked down at my feet. Miles stepped toward me, but I didn't move. I was no longer in control of my now raging hard cock nor, apparently, was I in control of anything in this situation.
Miles put two fingertips on my chin and raised my defeated face to look up into his face. It was like a spark went from his fingers to my face and I refused to meet his eye. In that moment, I could almost feel the power radiating off of him.
"You know what this means don't you?" Once again, he didn't sound excited or particularly happy he'd won our little competition. He was calm cool and collected, speaking as if he was a parent trying to explain to their young child that they were being punished.
"Look at me Isaac." It didnt even cross my mind to disobey. For the first time, I looked him in his eyes. His green eyes were piercing through my brown ones and for a moment, I simply held my breath.
