I depends on how far stretched out his rectum is. If he's a virgin and you're popping his ass cherry, then it's pretty tight, though you should be careful. If he's into fisting, you might as well just finish yourself off because it would be so loose (not that I have any experience with fisting and asses).

Its something you have to get used to. At first it hurts like hell but when you get used to it and your anal hole stretches out it actually feels really good. Someone who wants to be the bottom should use plenty of lube and give yourself anal fuck at least twice a week either with your BF's dick or a dildo.

This thread was about how it feels to penetrate a man's backside. Now it's turned into a discussion on how it feels to be penetrated. That is the exact opposite of the question at hand.

*drags thread back on topic*

My dear, after 30 months I think a little loosening (yes, har-har) can be tolerated~

Depends really, my experience with my boyfriend is pretty tight and it feels kind of like you stuck your dick down a just emptied bottle (assuming it has a big enough mouth, and don't tell me none of you haven't tried it) it feels moist but at the same time hard around, either way it feels good obviously or you wouldn't have your pedos =/

Topping, depending on the tightness feels really good but more so for the intimacy, imo. Bottom depending on the size can be uncomfortable as mentioned but after a few strokes you'll get use to it. As for anything else I hate rimming, fisting, all that other shit.