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The Actual Anal Penetration with your COCK
First, read all of the preliminary and finger stuff, because it all applies.
The following applies to both the penis and a substitute such as a Vibrator. We will only refer to the penis. Having prepared your partner using your fingers or another small device you are ready for penetration using your cock.
The Slow hand principle applies to your cock also. Be very careful about penetration. Done wrong, this can be more painful than, well, just about anything...childbirth, getting kicked in the 'nads, whatever. Done correctly, it's not painful at all, and can be very pleasurable. Be careful about "hitting the hole". This is far more difficult to target than a vagina, if that's the experience you're going on. 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. There tends to be a slight softness, in some people, above or below the anus that can fool you, no matter the amount of care, into pushing at slightly the wrong angle or spot, so that neither of you realize it's wrong (yes, that's right, this mistake can be made even from inside your lover's body).
Don't miss my mention of angle, either. Because of the number of positions you might be using and the variety among individuals, I can't even begin to advise you on a specific angle as being the one to use...you need to figure this one out with a lot of care and observation. Just remember that most angles are the wrong one, so you need to make an effort to make it better than random.
Prior experimentation with fingers, again, would settle this problem before it even started, especially when they are also applied before (or even during, if fingers are turning out to be enjoyable) penile 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 (bearing in mind that they may not be able to tell, perfectly, either), which is helpful because they know what hurts and what doesn't. But you should still be using your own hand as well, so you can feel what they're doing and when to do what yourself.
Remember my admonishment about a millimeter at a time, for fingers? If not, go back and read it, because I'm skimming over things here that are vital, but which I covered in the finger section.
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, and I do mean tiny, bit of pressure each time. It should literally take you minutes to make any real progress.
A big factor, as with all of this, is your partner. The more they can relax, the better. This means both their mind, and their sphinctor/anus. The part about making what feels (but is not) a "push" like when you relax your anus to have a BM is a huge help. Again, not a real push, as one might do when constipated or in a hurry, just the relaxation of muscles which is actually what many people do when having a BM.
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' sphinctor muscle. Once this is past, sliding in (if at the right angle) should be nearly painless. There are guys, though, whose penis is shaped in such a way that it still gets wider along the shaft, but for the average penis, which is about the same width all the way along except the head/glans, the difficult part is past once the head is inside.
Make sure the shaft was also lubricated, by the way, in case a "snag" from a dry area might cause discomfort. 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 (though that's a good idea with coitus, too) and gentler), 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). If you don't know where that is, you should have read the finger segment. il.
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