Some jockstraps have a pouch with an opening at top; the cup is supposed to go into the pouch through that opening. You wear the cup with the narrow end pointing down.
If your jockstrap doesn't have a pouch with an opening like that, but just has a simple pouch, wear the cup inside the pouch directly against your skin (again, narrow end down). If you have a lot of pubic hair, you might find that you prefer to trim a bit to prevent the cup from rubbing or pulling hair.
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Make sure the pouch faces forward. Step through the leg straps, like they are the leg holes in your underwear. Pull the jockstrap up until the waistband sits up around your waist. Make sure your penis and testicles are completely inside the pouch. The penis can point up or down, depending on what is the most comfortable.
You need some sort of jockstrap or compression short or it will not protect you. A cup must fit tight against the body to work properly. A loose-fitting cup will only slam into the testicles when an impact occurs, which can then cause pain and injury. Even some athletic cup-shorts which are being sold do not hold the cup tight against the body. Just because athletic shorts have a pouch for a cup does not mean that the athletic shorts will hold the cup in place firmly. You can put a cup on without a jockstrap, but not a real good idea unless you wear something over the cup to hold it in place real good against your body. I suppose some guys might want to wear a cup to "enhance" their bulge. If they are not going to be playing sports or working, I suppose that would be okay for them if they just want to "enhance" their male appearance.