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The good thing about this is that there are tons of tutorials out there on how to fuck yourself. Just be careful not to sprain your penis when trying this out. Now, unless he hasn't experienced getting fucked in the ass before, getting his own penis in wouldn't be that much of a big deal once he can bend it until it can reach at least the butthole. It might hurt for the first few times, but you'll get there eventually if you try hard enough. After that, he will push his penis down until the tip of his cock reaches the entrance to his backdoor. The next step would be to make himself get hard.
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