I want to help my reserved friends with benefits experience new things, where to start?

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I (27F) have been sleeping with someone (23M) for a little while now – the sex is really nice, considered a little “vanilla”, but that doesn’t bother me at all.

We’ve had vague conversations about experiences – he grew up fairly repressed and didn’t date or start having sex until later in life; I was the opposite. I think I might be the second person he’s had sex with which is a travesty for women everywhere because he is extremely, kind, handsome, attentive, and gentle.

After sex the last few times, he’s casually mentioned he’d do “anything for me”. We do feel safe and comfortable with each other, but I think he feels shy expressing exactly what he would like. I have asked, and he replies mostly with a version of satisfying me. I do think he would probably like if I just took the lead with whatever it is I want. Normally I don’t have a problem with doing this – I’m not sure if it’s because he’s so gentle and kind, or if he’s slightly inexperienced, but I feel nervous.

I am more than willing to do it – we have a great connection and I think it could take great sex and make it amazing. I am just curious little things I could ask him to do for me that aren’t overwhelming off the bat. Sexy, small power dynamic things that don’t necessarily drift into kink.

Currently – just with our bodies, voices, etc. I do have a vibrator we could use, but no other toys right now. He loves my tits if that helps!!

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