hey, nothign hard about it, i do it all the time, never had an issue. zipper, trust me yoru just carefull, its natural, i've never caught it.
hard ons, are hidden just like normal by tucking it in yoru waist band and letting the t--shirt hang over
Chaffing, never had it, and i'm a 7.5 inch guy
The outline of your dick through your pants, i wear slim jeans (not tight but slim) and i've never had an issue
Baggy short when sitting down, ok, i wear jeans and only jeans so yeah, i dunno
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