[Patreon Exclusive] CHEER FOR THE TEAM: Chapter 1 (Patreon)

It all started with a dare when I was hardly a teenager. Had my friend, Eric, not dared me to put on my sister’s cheerleading outfit, none of this would have ever happened. That idea would have never found its way into my head where it would lay dormant for years until I would make, quite possibly, the biggest mistake of my life.

We were living in North Carolina, the state where I was born, where all of my friends lived. My sister was a cheerleader for our high-school’s football team and the highlight of my week was going to those games and watching the cheerleaders take the field between plays. Those girls were hot—the hottest girls in our school, maybe even the hottest girls in town. They all had long, blonde hair that they would flip up and toss around throughout their routines. They all had nice, perky tits that would bounce up and down, loose-fitting belly shirts that would show off their perfectly flat tummies. Occasionally you would catch a glimpse of one of the girls’ under-boobs as her shirt rose up—oh, the days when young ladies’ tits were so perky they didn’t even need to wear bras.

And all of the men would stare at their perfect little bodies, transfixed, no one noticing the excited bulge that would creep into my pants a dozen times every game.

Every guy in the school wanted to date those girls, but it was usually only the football players that got the opportunities. I was looking forward to the day that I would have my growth spurt, when I was big enough to tryout for the football team. Oh God, I wanted it so badly. It seemed like every month, another one of my friends would show up for school a foot taller and fifty-pounds of muscle heavier. When was my turn?

It never came.

I was the runt of the litter, the smallest guy in the school. I was the only guy who couldn’t grow a single facial hair—not one little hair. I would get slapped on the ass walking through the halls, and my attackers would yell, “Sorry, thought you were a chick!” and then they would all laugh. Every night I would go to bed and pray that I would wake up with that football body that the girls all fawned over. But sadly, that day never came. The only sport I could ever play was bowling, if you can even call that a sport (and I was pretty good at it, by the way).

The benefit of being terrible at sports is that you put more focus into school and studying. I was at the top of all of my classes, nearly-perfect grades. I was looking at Ivy League schools and big-money scholarships (which were highly competitive, but I had a pretty decent shot). But when you’re a teenaged boy, you don’t care about that stuff. You just care about girls and being popular—two things I didn’t have.

I was in the eleventh grade and my sister had gone off to college. There was a girl I liked, a cheerleader (naturally), named Emma. Emma was gorgeous. Every guy wanted Emma, and Emma was single. The idiot inside of me was convinced I had a shot. Every idiot in the school thought they had a chance. But I had an in; I was best-friends with her brother, Eric.

“Ask her if she likes me,” I said to Eric, and he rolled his eyes.

“I doubt she even knows your name,” Eric said. “No offence.” I didn’t take any offence. I was totally used to girls not knowing my name.

“Well, tell her my name. Put in a good word for me. Build me up—you know—help me out, here,” I said. I was a dumb kid, like all kids, too shy to actually face Emma myself. The thought of introducing myself and having a conversation with her was absolutely terrifying. Yet still, I wanted her to be my girlfriend so badly. I was willing to do anything, and that’s what I told Eric.

He smirked. “Anything?” he said. It’s every teen boy’s dream to torture their friends, to humiliate their buddies for a good laugh. And I was all his to do whatever he wanted with. I was too stupid to realize that ‘putting in a good word for me’ would do little to nothing (more likely nothing) for my cause. And then Eric made that fateful dare—the dare that would change the rest of my life. “I tell you what—Wear your sister’s old cheerleader outfit to school tomorrow and I’ll tell my sister you’re the coolest motherfucker on the planet.”

My heart sank into my gut and my face became bright pale. It was an absolutely demented deal and I took it. Isn’t that a testament to the stupidity of a teen boy—I’d sooner wear my sister’s skimpy little cheerleader outfit than introduce myself to Emma.

So the next day, after my parents took off for work, I snuck up to my sister’s bedroom. My sister was living across town in the university dorm-house but she left most of her things behind. I went into her closet and found it—red with white stripes, short skirt that hardly reached my mid-thighs. I put it on and looked in the mirror and then the nausea really kicked in. It didn’t help that I was in serious need of a haircut, my shaggy mop nearly touching my shoulders.

Why couldn’t I have been blessed with a football body? Then everyone would think it was a big joke. I could have played it off as a silly joke, with my big shoulders stretching the little shirt out, my thick legs extending down from the skirt… But instead I was built like a girl—thin arms, thin legs, thin body. My lack of body hair didn’t help anything, and neither did my perky butt, which made the short skirt ride up.

I couldn’t tell you what was going through my mind that morning. I must have really wanted Eric to put in a good word with his sister, because I actually went to school in the outfit. I actually stepped through the doors in that little skirt, walked past hundreds of students towards my locker. I didn’t even bring a change of clothes in case of emergency, in case I came to my damn senses. Once again, a testament to the stupidity of a teen boy.

I felt a firm hand slap my ass and I jumped into the air. I was used to the odd hallway-spanking but I wasn’t used to the reaction I got. When I turned to face the slapper, his expression dropped. “Holy shit,” he said, eyes wide, lips parted. He actually thought I was a girl. That slap wasn’t just some mean joke. It was an advance.

Just a few minutes later, I heard a whistling behind me. When I turned around and faced the crowd, one of the men said, “Hey babe. Looking good.” The moment I replied, they all made that same wide-eyed, lips-parted expression. Hell, from twenty feet away, staring me in the face, they couldn’t even tell I was a man. They needed to hear my voice, and even then it took a moment for them to figure it out.

And it happened over and over that day. But something deep inside of me liked it. When Eric came up to me, laughing, nearly in tears, I had to pretend like it was torture, like it was so humiliating. I couldn’t possibly tell him that I was actually enjoying the attention, that I liked the way the catcalls and ass-slapping made me feel, filled me up with warm energy. For once I felt like my body was good for something; and sure, a part of me hated that I wasn’t ever going to be a football player and score the winning touchdown, but here was an outfit that fit—and I liked it.

Eric, the bastard, never went to his sister and told her about how awesome I was, not that it would have mattered anyway. A month after the cheerleader costume incident, my parents got a divorce and my dad took me away with him to Canada—just me and him. And soon enough it was just me. His job was on an oil rig and required that he was out of town for three weeks at a time, back for one. Half of the time, he just ended staying up at the rig for his week off, and I hardly ever saw him. I had the house practically to myself, which would have been great had I known anyone in the whole country.