..Oh and if you need a good non-obvious sex toy, most drug stores that I've seen all sell this same little toilet plunger with a plastic handle. The handle has four or five little evenly sized balls at the top. It's as if it were made for anal play and there's nothing wrong with storing it the bathroom ready to go at any time.

This doesn't sound stupid at all. It's a very real problem for a young person who still lives at home.

Probably more important than lube, is learning how to relax the muscles in your ass. This is not especially difficult but it does take some practice as the normal condition of these muscles is to be at least slightly tensed to keep the anal opening closed.

With practice, just about any anus can relax enough to open up enough to take just about any penis or penis size object. Some can open much larger. This takes a LOT of practice and stretching, however. Look around the internet, it's not hard to find photos of fist fucking or of guys with two liter beverage bottles in their asses.