The first time I got fucked, at age 44, it hurt so bad that I thought I was going to pass out. You may as well know and be prepared for that. Some guys say that their first time didn't hurt at all, so you'll find different stories, but don't let anyone tell you that it definitely won't hurt, because it probably will.
Having said that, in the time since then I have come to understand how to prepare myself and to control the penetration to minimize the pain.
In cases where I anticipated sex, I would prepare myself in advance by slowly inserting a butt plug in my ass and keeping it there for a couple of hours at least. This is helpful even as much as a day in advance for me. The butt plug itself, or dildo, if you prefer, will not be painless, but you at least have the control to take your time with insertion and work it in until it feels comfortable.
In cases where the sex is spontaneous and there wasn't enough time to prepare yourself, an alternative would be to have your partner insert his fingers into your ass. First one finger and then two. This not only helps stretch your sphincter, it's a hell of a lot of fun for both of you.
If you worry about cleanliness (I prefer a clean ass) you should give yourself a "douche." Some doctors suggest that enemaas can be addictive, but you must decide for yourself if it's worth the risk to have clean sex.
Even though my first time was painful, I didn't give up. After I suffered through the initial penetration, the pain subsided and I was able to enjoy making love with the dear, sweet man who was with me at the time. Now I love to get fucked if it's safe, clean, and painless.
I am sure there are lots of other perspectives from people here who can add their own experiences and valuable advice.
Don't forget your condoms!
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