I had a friend who was sort of in the same position and real down about it. I've been his go-to lady for talking about girl frustration for many years now. When I started working in a sex shop I would just ramble on about products despite his obvious discomfort, and like all my friends/family that I've subjected to this technique, he eventually became desensitized and could actually consider the products for what they were rather than just embarrassment items. Long story short, with my help he decided to get a Fleshlight and was very pleased about it. I don't know if I'd have gotten him one without his input, though. Possibly, but only then it'd've been because I've known him for a decade and we're close enough that he wouldn't have taken it the wrong way.

So, maybe bring it up in a sly way, but don't go out and get him one without warning. Start by talking to him and finding out what his situation actually is, and whether this kind of a product even interests him. I'd do it over a couple conversations, you might freak him out if you bring this up all at once. For me it was easier to ramble on about how interested I am in toys and then sort of side-note, "I'm so ridiculous, I just want everyone to have awesome toys. Oh man, have you heard of the Fleshlight?" and go from there, because then it seems like they're doing you a favour for listening rather than you bringing it up out of pity.