Embarrassment
So the straps were a requirement for engaging in the sport. I suppose it made as much sense for the school to provide the straps as it did for the school to provide the uniforms. But another issue might have been that the guy felt more than a little uncomfortable going to (probably back then) the local drug store to purchase one. And even telling your parents what you needed and letting them make the purchase was another potentially embarrassing situation.
The guys who were getting a strap for the first time were probably scared stiff. If the other guys said "Large' that is what you should say. But in straps a men's Large is a very different size from a boy's (aka "Youth") Large. The other problem strap manufacturers have is the lack of correlation between waist size and penis size, and straps are sold by waist size which assumes that as the waist gets bigger then the pouch size should get bigger too. But guys with a small waist may have a large penis. And vice versa. You see the fitting problem here.
I am reminded of the classic scene from the movie "Summer of 42" where the coming-of-age lad (actor Gary Grimes) decides he needs to have condoms. He goes to the drugstore and meets a friendly druggist and then hesitates to explain to the druggist what he is really looking for. It's a classic and funny movie scene as his predicament plays out relating to the embarrassment in just saying "I need a pack of condoms". In 1942, condoms were kept behind the counter in drug stores.
I can see guys in need of their first strap potentially facing a similar situation which is probably one reason why coaches passed out the straps.
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