…you wear your older brother’s tighty whiteys when he is old enough to get a job and start buying boxer shorts. Boxer shorts become a lofty goal that you will reach for for years. You walk around at school, constantly and obsessively self-conscious that all of your classmates have X-ray vision and can see straight through your Wal-Mart khaki cargo pants and know that you’re still wearing tighty whiteys! It will take you several months into your 8th grade year to even realize, to your utter mortification and adding serious insult to injury, that you are wearing your brother’s undies wrong. Unlike the rest of the world, you are too poor to put your pants on “one leg at a time”. Wasting your time getting dressed slowly is for the upper middle class. So you step into your brother’s underwear which is too small for you now and just pull ’em right up to their resting place, a little too snugly around your waist. By pulling your undies up this way, your weener and berries end up being pulled up along with your undies and pinned in a bulge between you and said undies. You don’t look at other people’s crotches (at least not yet anyway) and so you don’t know that having a weenerberry bulge in 8th grade is not common. It will take a very embarrassing public humiliation incident to call this to your attention.
When you turn 14 you can get a job and finally have money and do whatever you want with your life. So you get a job at a pizza place. With your first paycheck you make almost $40. You go to Structure at the mall and they have a sale on boxer shorts. You buy two pair and wear one out of the store. You’re free! Literally and metaphorically! You start the practice of sagging your pants because you want people to see that you wear boxers like every other man on earth. Then you realized you are wearing the same two pairs of boxers over and over again and so you stop sagging.
Ultimately, you’ve improved your life drastically in the weenerberry arena. You walk around school confidently, swaying freely in the breeze, kind of sort of hoping that someone would pants you.