Both questions at once. I think it can be worn pretty easily under cloths. You would want them to be a little baggy. I have worn mine at work during different intense times of Penis Enlargement. Mind you I have an office. But I have had to get up in front of people in my office to shake hands and I have walked down the hall to the water fountain and no one has noticed. My place of business is predominately women so they may have thought I had a boner rofl . But all kidding aside I think it will hide itself pretty well.
Also, I have never had a problem with the base hurting me because it did not have a cushion. I use a pretty thick piece of PVC for the base so it does not cause many problems. Obviously, if you use a tremendous amount of tension it might get uncomfortable after a while but I bet you would say uncle to the noose before the base started hurting you.
I don't see why we can't ship to an army post office unless you think they might check the box. I can see the headlines now, private JO5 caught heading an illegal penis stretching ring smuggling [words=https://shop.mattersofsize.com/products/sizegenetics-penis-extender]extenders[/words] onto base :blush: .
All kidding aside, I don't see a problem, but you know the Army better than me.