It could be sexual thoughts (horny) or an attempt to steer the conversation that way... but, seeing your 40? (ie, he's not likely immature, young and horny looking for strictly sex) and you really like this guy (assuming things are going well between you), it could also just be a random question he's throwing out there (ie, nothing to read into, it was just something that popped into his head so he asked, especially if he couldn't think of something else to ask). It may have been a bit of both?
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He's turning the conversation into a sexual conversation, it's a classic tactic and a very obvious one.
I find that to be highly inappropriate, and you should simply ask him why. 9/10x he just wants to have sex or is fantasizing you sexually out of lust. And I suggest that you set boundaries or cut him off. Unless he has a serious question concerning that, that is not his business.
Your guy friend is physically attracted to you and he wanted to picture you like that in his head.
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He's having sexual thoughts, and expressed them verbally.
he is showing interest for bed purpose. you know what I mean.
That question has come up for me in a silly jokey way but because I'm in high school. If you're 40 like it says you are I would be concerned
I'm guessing you already know.
he's curios to imagine you naked.
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