We send our nude pictures to each other but how can I tell him I want more?

A female age 36-40, anonymous writes:

This guy I knew from school almost hooked up once (almost a year ago) but didn't because I was not single at the time. Now I'm single and I'm pretty sure he is too. We still talk and he often sends semi-nude pics of himself and asks me to do the same via IM which is great and all but... he doesn't seem to want to actually hook up now? Or at least, he's not initiating it, so how can I... you know, without seeming like a creep lol?

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A male reader, anonymous, writes (7 February 2010):

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