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Tips to be a good top?
If you're both bottoms with one of you attempting to top, then all this dominant stuff is likely to be less obvious. You can also invest in a cockring to keep your erection harder if you are afraid of losing it.

I think it is possible to have hang ups about putting your penis up someone's rectum and if you were using condoms, (which I hope you were) that's an added difficulty to sustaining an erection for some men. You would probably need to find a way of having some foreplay that actually excites you, like rimming, maybe, or mutual masturbation... or fondling him while he's giving you oral, or something.

Depending on how excited he is from the start, before penetration, he may not even take very long to come once you're inside. But if this requires longevity and stamina, it's best to lay off the booze, the smokes and the grass...

Be gentle and courteous as you attempt penetration. He's tried objects, so he'll know how it feels, but you can still get hurt when you're not the one in total control.
He should maybe attempt sitting on you (astride you, facing or with his back to you) for his first try, that way he gets to control how much length he takes and how deep he lets you in. The amount of lube used is for you both to assess.

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