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I don't wear undershirts when I am wearing dress shirts. Wasn't the point of wearing an undershirt so that you could wear your dress shirt several times before it needed to be laundered?
When I was a little kid, I used to tuck my dress shirts (on the few times I would wear them) into my underwear to keep them from riding up. I wouldn't dream of doing this today.
As for the penis thing... I just let it go where it wants. Beisdes, I wear boxers, so even if I wanted it to lie "up" it would go where it wants in the end.
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"My hands are on fire. Hands are on fire. Ain't got no more time for all you charlatans and liars."
- Old Man Luedecke
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