I got a jock with a cup today ..
Was wondering do you put jock on first and the put cup in?
Or do you put cup in the pouch first then put jock on..
Like others mentioned I too put the jock on and pull up to my thighs then get the cup in it right, then pull it on up and get myself adjusted in it. Usually wearing the cup jock next to my skin.
I have somewhat double jocked in the past, but I learned a little trick way back in my high school/college days. Cut the leg straps off the cup jock. Usually left the cup in the pouch of it then (since it didn't get washed much). put on the cup jock and cup, minus the leg straps, then put on a regular jockstrap, this keeps the cup pulled back and snug even with the cup strap missing the straps. Then depending on the weather or personal preference, can put on sliding shorts or compression shorts over that.
The when the need for the cup is over simply pull the cup strap up and slide it down over your other clothes and off.
Recently I noticed some jockstraps in a lockerroom with the pouch cut off of them leaving just a waistband and legstraps. I took a couple of them to the equipment manager and ask if he knew what was up. He said he wasn't sure but he had had several requests for both a jockstrap and a cup jockstrap from several of the baseball guys and lacrosse guys. So my assumption is they are wearing a regular jock more and just shoving the cup, covered in the cup pouch missing from those jocks, in the pouch of the regular jocks to hold in place. Seemingly great idea for easy in and out of their cup and it means more of them are now wearing a regular jockstrap.