That's okay with me – the thing is that he wants me to masturbate him, but I'm uncomfortable with that. I'm scared of squeezing too hard, or not doing it hard enough, or pulling his hair. I know that sounds stupid, but there it is. I guess if I do it too hard he'll let me know, but then again, maybe not – he might just lie there thinking, "Dude, this sucks." I guess I'm asking what most guys like.
The best thing I can recommend is that you talk beforehand (pun not intended) and make sure he understands that he's to tell you exactly what he wants. Tell him you want to know exactly what he's feeling and what you can do to better please him. I certainly can't tell you how he likes it – but he definitely can, and he will if you coach him right.
Do you find yourself masturbating more often during some seasons than others? Why?
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