Put the cup in the jock strap and tell him to wear it like underwear...
Any boy that plays PE should be wearing a jockstrap for the support of his family jewels. If the boy has started wearing boxers before 7th grade ( Jr high) he should wear a regular Bike jock under those boxers. I would recommend however try fitting your son well before that if he skateboards often with a cup/ jock NO compression shorts.
In general, boys are no encouraged to wear bras. If he is interested in wearing a bra or if he is uncomfortable when working out because of a larger chest, then you and your son should consider it.
depending on what kind of guy he is. but usually, yes
When I was young my coaches told us a cup was not necessary for football but it was manditory to wear something for support (a jock strap/athletic supporter). it is more important in baseball to wear a cup because the baseballs are thrown and hit at high speeds.
Unless he has any disabilities or conditions - no.
Sorry, but I would say yes.
If it is formal, that will be fine. If it isnt formal, I would just suggest a shirt.
Yes. Let him but only at home. Dont let his friends find out.
No, making your son wear his sisters pants is not a good punishment.
Well I would let him wear Bras . Even take him out Bra Shopping and let him get some . But Only let him wear them around the house .
Then you should probably tell your son to break up with her...you dont want that kind of person to be with your son, right?