What Are You Wearing?

Can we discuss the nuances of this question?

Sometimes men I talk to online will ask me what I plan to wear on a date. I find it slightly offensive. It puts a lot of pressure on me to wear something really slutty and sexy–and frankly, I don’t see why it matters. If we are meeting for sex, my clothes will be hitting the floor soon enough.

Not only that, but the one man I met who asked me this repeatedly (Mr. IT, if you remember that trainwreck), would show up looking less than stellar himself. I would show up in a tube top and short skirt, mostly because I felt like I had to, and he would show up in a wrinkled t-shirt and shorts–one vertically striped, one horizontally striped. I’m not one to judge based on wardrobe, but if a man is going to imply that I need to look hot, then he should make an effort to look equally presentable. Throw the clothes in the dryer for five minutes, and pick out a top that matches your bottoms. Just sayin’.

My Dom also frequently asks what I’m wearing. I feel like he has more of a right to do so because his job is to sexualize me, not to make me feel comfortable. However, I’m never quite sure what to make of the inquiry. He doesn’t ask me what I’m going to wear on a date, unless he specifically tells me what clothes he wants me in (he has promised to tell me to wear old clothes sometimes so he can rip them off me–yum), but he will randomly ask what I have on at any given time. Does he want what I’m wearing to be sexy?

I’m a stay at home mom who works with children part-time. I hate to shatter the illusion, people, but I’m usually decked out in jeans and a t-shirt. In the summer if I’m hanging out at home I can often be found in nothing but my undies, but I can guarantee you I am not dressed in slut-wear unless there’s a specific reason for me to do so.

So I wonder, does he want the real answer? Or does he want to hear what will turn him on? Should I admit I’m wearing cut-offs and a white wife-beater? Or does he want me to say I’m in stockings, a garter, a skirt and see-through blouse?

What is the correct answer to this question? Men and women both, chime in please!

7 Comments on “What Are You Wearing?”

  1. daredodie says:

    It can be annoying at times. It depends on the guy that asks. If I really want his attention I’ll say its sexy no matter what. If I don’t care either way I’ll say jeans and a tshirt but then I’ll say no panties or something. I don’t blame you for being bothered by the question itself though.

  2. I’m sure you’d look hot as hell in cut-offs and a white wife-beater too! So I’d go with the honesty…

  3. micklively says:

    Isn’t it just part of the build-up, titilation, and anticipation? Seems like a good thing to me. Your clothes might soon hit the floor but it’s still fun taking them off. The moment you tell me about stockings and lacy knickers, I’m imagining kissing the skin in between the two.

  4. thosebadshoes says:

    I usually lie about what I’m wearing when asked. I’m a SAHM mom too so I’m generally not walking around in latex and lace either. I think it’s just part of the fantasy, why not indulge?

  5. I think the “stockings, a garter, a skirt and see-through blouse” is a major turn-on but it should be said only if thats the honest thing to say. I always like to know, but for me its like micklively says…its all about the titilation and anticipation for the build up! Bottom line is be honest, but the flirtation is always fun!!! But I am sure you are stunning wearing anything…confidence is truly the best outfit!!!

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