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What to wear!

One of my loyal readers wrote me this morning to ask,

I had an interesting first meeting w/a potential hookup recently that brought up a question for you. We were ogling each other over drinks and the topic of clothing choice for a hookup date came up.

Specifically, the question of how much skin to show. She preferred tight shirts that showed the definition of pecks (for men) and breasts (for herself). I tend to go with a button-up shirt that shows a little neck and like seeing ample cleavage on a woman (not that she necessarily needs to be well-endowed, even cleavage on small women works for me).

What are your preferences, for yourself and the men you "see"?

This is funny timing because just last night one of my lovers and I were talking about clothing and what's sexy. Some friends bought me a custom corset for my birthday, and almost everyone I know thinks I look particularly good in corsets, but he was saying that corsets leave him cold. Go figure.

The thing about clothing is that there are, as usual, several things happening. First, you obviously want to wear something that feels good, comfortable, flattering. And you want to wear something that's going to attract your (potential) lover. When your date is someone you don't know, though, you don't know what will be attractive to them! So, what to do? Fall back on what's attractive to you, of course.

This makes sense, and I think it's a good approach. Alternately, there's always the choice of wearing an outfit that nets lots of compliments.

Personally, I like to wear an outfit that looks good (to me), but, more importantly, that feels sexy. I'm pretty sure that when I feel sexy, I project sexy, and that's a good thing to do on a first date (and even better on a second date!) So, what am I likely to wear? In the summer, which is, I must say, way better for flirty attire, I'm fond of flippy skirts and a lacy camisole. This ends up showing a fair amount of skin and being rather clingy, at least on top. I also have a couple of fun little dresses that I like. And, depending on how I want/expect the date to go, I may or may not wear panties. But that might be another post.

As for my dates, I'm not sure I care a whole lot about what they wear. For a first date, I like to get the impression that he's put a little effort into his attire, but it's far from a deal-breaker if he hasn't. I mock men whose pants fall off their hips at the slightest provocation, but I like it when I find that my date's pants needs only the most gentle encouragement once we're in the bedroom. I love touchable fabrics, as they give me an excuse to put my hands on him. And I really like my date to look comfortable in whatever he's wearing. That sexy thong isn't doing you any good if you spend the whole evening squirming as a result of wearing it, after all.

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