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Make sure you start out slowly and each time you will notice it gets a little easier. I can remember bottoming for the first time — I had absolutely no idea where to start. They act like a dick in ass first time and allow you to apply lube consistently deep inside. Note that there are really two distinct muscles in the anus — the dick in ass first time one you can control, and the interior one, which is an involuntary muscle. James 3 Apr Reply. YOU lube up your asshole, sticking your finger s inside, and you or he can lube up his cock. Donald Wallace 14 Jan Reply. Is there a reason for it? As you gain more experience and want to begin exploring more vigorous anal penetration, be sure and read the follow-up article on enemas.