I don't think it is required that ALL rimjobs involve penetration. Seems to me that lots of guys are happy just to have their ass eaten... It also seems to me that the large majority of guys who rim me don't actually get inside, either. Nor is it necessary. A bit of stimulation to the anus with the tongue is nice enough, at least in my book.
A tongue isn't always long enough or shaped properly to penetrate a guy's ass. And all tongues are different, to a degree. Some are short and squat, some are long and pointed, some have round, blunt ends, etc. Logistically speaking, when your face is pressed against a guy's ass, it may not always be possible to get the right angle or be deep enough between his cheeks to get inside. Clearly, ass cheeks will vary, too!
The best thing you can do is to just keep doing it, if you and the other guy enjoy it. The more you do it and the more you practice, the better you'll get. And there's no reason why you can't ASK the guy what feels best to him, if the circumstance provides enough comfort level for you to do so. Not everyone wants to be rimmed in quite the same way, I'm sure.
I've had guys who CAN get a LITTLE bit inside, I've had guys who can't do much more than lick around. I've had some who kind of nibble the whole area -- done gently, this is OK; done roughly, it isn't fun at all.
It seems that lately, at least over the last two years, more and more guys are asking if they can rim me as well as suck me. Gay porn at work here, telling us once again that this is the formula to follow? Or more likely, just another aspect of sex that men enjoy. For me, I'm fine with it, but it doesn't usually keep me hard. This is not to say that I don't enjoy it, but I sure don't require it. If a guy wants to do this, I never turn him down, as long as my dick gets plenty of attention, too. Yeah, it feels great, but I don't live for it.
Just keep doing what you enjoy and what the other guy enjoys. Don't worry about HAVING to do it any certain way. If he asks for something, give it a shot. Try another angle. If he seems satisfied, probably you're doing a good job as it is.
Since you didn't ask about potential hazards that might be involved, no need to get into that now -- just use common sense. There's good info from Doctor Danny already posted here about medical risks involved with rimming; check it out.
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