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I'm thinking of trying bottom anal sex with a friend. I've played with objects before, so it isn't really tight. My main question is, does it really feel good? Can you feel it at all? Should I masturbate before we start?

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It seems to me you've already answered your first question. Does it feel good? Well... I can't imagine it not feeling good if you've played with other objects in there. You wouldn't do something more than once if it didn't feel good, right?
Although, the girth of the objects you've been using vs the girth of your partner's penis will feel differently - I'm assuming he would be bigger, so you'd feel it more, unless you've been using some really large items to play with.
Another thing I'd like to note is that random objects people tend to experiment with around the house are hard, and while we call a man's erect penis "hard", it is still very soft in comparison to, let's say, a fat marker, carrot, plunger handle, etc. and in my opinion, the penis feels better than the unbending, stiff, hard objects one might use.

As for masturbating before anal sex - I'm not certain why you ask such a thing. But then again, I am not the gay male you ask for to answer your question. And so, I'm sorry for butting in (no pun intended), but noone else had answered at the time and well, I have had quite a bit of anal sex and experimentations myself.
I realize porn is just for show and entertainment and a lot of it is faked, but most often in gay male porn, the bottom is masturbating while receiving anal action - I don't see why not, if I'm being aroused and feeling good from something, I'd want to masturbate, too. Or better yet, having him reach around and do it for me, lol. (I have done this both ways)
But again, I am female, not male - so maybe masturbating during anal isn't the same for guys. I don't know why it wouldn't, since so much of the same stuff turns men on as women... the sucking, licking, stroking, teasing, etc. of the ears, neck, nipples, genitals, anus, etc.
I've done alot of experimenting, but using a strap-on on a guy while jerking him off isn't one of them so I have no experience to say how it went.

Anyway, I don't masturbate before sex, be it vaginal, anal, oral, whatever - maybe afterwards if I'm not satisfied enough, lol, but never before. Never heard of anyone doing so, either. So that one catches me off-guard, really. %-)
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Dude it sucks I stuck me fingers up my ass, and it hurts! Ive even tried a toothbrush handle it sucks trust me.
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Why ask just gays? Straight couples also enjoy anal sex, just as much as homosexuals men do. Being gay means you like other men, not just anal ;-) Anyways, in my opinion if you are relaxed and prepared for it, it can be enjoyable. Might take a few times to get it right.
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