The only time I have worn a cup or box has been when playing cricket. (Though when my children were young and like most other dads I functioned as a useful piece of gymnastic apparatus for them I could have done with one. )

If I had played cricket regularly I would have had to search for a custom made box big enough for me; as it was I made do with what was available by keeping the family jewels inside the box and making room for them by letting my penis point outside (there wasn't any other choice in any case). A very high risk and extremely uncomfortable strategy; luckily for me I took no hits and have three children to prove it.