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What should I have in mind when asking this kind of quite a delicate question? Any suggestions? Is it appropriate at all?

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    Seems legitimate to me. If you use proper terms, I don't think there is any room for complaint. – michael Sep 8 '11 at 0:43
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    Can you actually post what your question is? That will give more context for people to answer and may even yield some suggestions or improvements on how it should be asked. – Matt Chan Sep 8 '11 at 4:20
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    Ok, question would go like this: "When I run longer distances I get some problems with placement of my scrotum. It seems to me that my ties are slightly pushing it from the sides so it goes a bit up and keeps going in that direction more, as I run longer. It is uncomfortable (not painful at all) and it happens mainly on the left side. Should I try to change my underwear or try to run in a way that I don't push my left leg as forward as I do now? What might help me with the situation?" – user1653 Sep 8 '11 at 6:38
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The fitness industry makes special clothing to deal with this sort of thing, and no matter how embarrassing or somewhat "crude" the topic may seem, I think it's a valid part of fitness. It wouldn't be disconcerting at all to see a question about how to prevent getting blisters on the hands when beginning rowing or something, but people are a little shocked or taken aback when they see questions about the genitals and such. My suggestion would be to make it as polite as possible, using proper medical terms, and leave it at that. I believe the example question you have posted in the comments of your question is adequate in that regard.

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