a very important question...

[argomac]

If you're worried about it, then yes, it will hurt.
My advice (for what it's worth): make sure you really want to; Make sure your partner understands that it's new to you; use plenty of lube. If it does hurt, then for God's sake stop.
It will feel a little uncomfortable at first, yes, that's to be expected. To that end, it's probably worth trying initial penetration a couple of times, so that your bod can get used to it. Get him to lie on his back, and lower yourself on. This puts you in control, and you can stop if you're not sure.
Don't let this worry you though. This is just my advice on the best, most appropriate, safest way to do it first of all.
Some guys like it, some don't. You'll have to judge for yourself if you like it or not. While most guys will tell you that it is a little painful initially, they'll also tell you it gets a lot better. But some guys don't like it at all.
You have to decide for yourself, by trying it with someone you trust

 

[josher]

And you don't HAVE to have anal sex to be a gay relationship. Many gay men don't enjoy it, either as tops or bottoms, and are in loving, long term relationships.

 

[hercsurf]

Yeah it hurts...

( hows that for succinct)

 

[gabriel1]

Mere words cannot explain how rewarding it can be for both the probee and the prober

 

[pkacrotjs]

You might consider reading the posts in health and well being, once of which is:

http://www.justusboys.com/forum/showthread.php?t=160269

 

[Eternaldarkness]

first, clean yourself with and enema or a douche.

second, prep yourself first. Finger yourself to loosen up a bit. You'll get use to your own fingers more.

next, let him finger you more before he goes in.

last, jerk your dick. focus on how your dick is feeling good. Somehow that always take your attention from the pain. If you prep yourself, there isn't too much pain. There will be discomfort, but if you jack off while he penetrates you, you will feel more pleasures than discomfort.

 

[KennyD]

Like has been said .... YOu DON't "Have" to have anal sex to be in a Gay relationship ... think thru your options before you do something that you might not be ready for ...