Actual Anal Sex

First, read all of the preliminary and finger stuff, because it all applies. In fact, it is a very good idea to start out with fingers, even if your real goal is to you a penis. This allows your lover to get used to the feeling, and to relaxing their anus in the right way.

Once you've worked your way up to the penis part, don't forget the importance of taking your time.

When working up to actual penetration, use your hands to stimulate your lover,

Don't forget, though, to be very careful about penetration. Done correctly, it's not painful at all, and can be very pleasurable. Ask any swinger.

Be careful about "hitting the hole". Enough light and a visual lining up is not that romantic, but is safest. This is also another reason to start out with finger penetration.

A fingertip already inside a relaxed lover can be the perfect guide, actually making insertion of the penis easier and less painful, believe it or not.

If the position allows, and you're both comfortable with the idea, you may also have your lover help guide you in

Go very slowly. The best method is probably to make a slight pumping motion, starting out just pushing slightly at the opening, not actually penetrating at all, and simply adding the tiniest bit of pressure each time.

A big factor, as with all of this, is your partner. The more they can relax, the better.

No amount of lubricant is too much, either, if there is any concern about pain. The big key in getting through this is the initial penetration of the bulge of the penis' head getting past the actual anus' sphincter muscle. Once this is past, sliding in (if at the right angle) should be nearly painless.

Make sure the shaft was also lubricated Once safely inside, and once you've found the right angle, and everything is going well (basic sexual pumping works fine, here, but you may need to start out slower, it may be a good idea to shift angle just slightly, so that the head of your penis is pressed more against the inside where the anus is closest to the prostate (men) or vagina (women).

Once you've done the full penetration thing a few times with your lover, and the penetrated is getting to the point where relaxation is easy, and pain not really an issue.