He will never forget that first time his cock felt a hot, wet pussy envelop him and the scent, sounds and intensity of his first orgasm inside her… I sure recall mine with Linda…
I once met a 40-ish woman who got special satisfaction from taking young boys' virginity, giving him his first fuck, and teaching him how to pleasure a woman.
Yes, she will take him bare. And she will make it happen quickly, almost by surprise, before he has time to think about what's happening and get self-conscious about his performance. Virgin boys often need several orgasms before they feel truly de-virginized (I needed three) so there will be plenty of opportunity after his first release for him to explore and appreciate all the sensations of fucking a woman.