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Will I get less nervous to touch him "down there"?

I gave my boyfriend a handjob for the first time tonight, and I had never done it before. I didn't let him touch me under my pants as I was much too nervous. We have been together for a little over a month now. I'm afraid that I wasn't good at it, we are both rather new to this and when I told him I didn't really know what to do, he told me it was okay, that we will just learn together.

Will I get less nervous to touch him down there the more we do it? Will it feel more natural, like I know what to do?
Also, why when he was going to cum did he shove his penis back into his pants?
Will I get less nervous to touch him "down there"?
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