Addressing the Undressed

Story Sent in by Herman:

On our date, Jessie wore a skirt that left little to the imagination. She kept tugging it down and I wondered why she chose to wear it or at least why she didn't include leggings. I couldn't help but notice that she had incredible legs.

Of her own volition she must've noticed it too. I say that because midway through dinner, she asked if I would mind if we stopped at a department store afterward to pick up some leggings.

We wound up in a Macy's and it took her an inordinate amount of time to find a pair that she liked. She also selected a blouse. Once she bought them she made for the bathroom to put the leggings on.

She came back in her new blouse and leggings and handed me her dress. "Your turn," she said.

"My turn? To what?"

She shook the dress right at my face. "I changed. Your turn."

"You want me to put on your dress?"

She said, "You have nothing else to change into. I just changed. It's only fair."

I laughed at her joke. But she stamped her foot and said, "Now! This was humiliating. The least you could do is do the same."

"I'm not going to do that."

She muttered some things under her breath, pulled out her phone, and demanded to the party on the other line that they come and pick her up.

"So I guess that's good night, then," I said. She didn't reply. An awkward end to an awkward date.


  1. A fool and her dress are soon parted....

  2. Her intentions all along were to get you in that dress. But also, if she was in a skirt, why was she also in a dress? Either she has a strange sense of style or you didn't understand something about her outfit.

    1. I think the op thought the dress was so short that it was a skirt.I suspect the real reason was because he did not have nice legs and did not want to lose the battle of who wore it best...

  3. so many questions on this one...how did the skirt transform into a dress? why did she wear it to begin with? how come he had to change since she changed? why does she want her dates to wear her dresses? are they even the same size? why didn't he just get some leggings and a blouse too?

  4. If the dress had distinctly separate top/bottom parts, it's not too unreasonable to assume he didn't realize they were connected until she changed

  5. Yeah, stomping your feet like a bratty child will really make me bend to your will. Not

  6. I find it hilarious how seriously we all took the skirt/dress discrepancy. I'm proud of us.

    1. Dudes know nothing about womenswear. Certainly don't know the difference between a dress and a skirt...

    2. Easy, easy. I know what a skirt is as opposed to a dress. Heck I can use "peplum" correctly to describe someone's flouncy skirt/blouse. Though, to be fair, most women find this creepy.

    3. Easy, easy. I know what a skirt is as opposed to a dress. Heck I can use "peplum" correctly to describe someone's flouncy skirt/blouse. Though, to be fair, most women find this creepy.

  7. Hm, did you pay for dinner? It's possible she thought you might foot the bill for some new threads. Play little miss innocent date who was revealing too much and super uncomfortable, thinking you'd feel bad and offer to buy her something to cover up to make her feel more comfortable. That could explain her taking so long to find leggings. Waiting for you to give some sort of indication you'd pay. "What's taking so long? Can't decide? Get both, I'll pay." Do you remember anything she said during this time? Maybe talking about how expensive things were or price dropping? I am wondering if she gave any hints verbal or non that she was hoping you'd pay for some shopping.

    I think she was trying to buy time and once she realized you were oblivious to her clues. (Or not going to fall for them) she purchased some leggings to save face. How else would she explain spending so much time and suggesting taking her to get some leggings. It would probably be too rude to say "I'm not buying anything because I assumed you would." The passive aggressiveness would make sense to me because she'd be annoyed she had to spend money and you didn't offer your wallet. That would explain her demanding you wear her dress.

    Honestly who goes to Macy's JUST to buy leggings? That store is expensive. (In my opinion) If I just needed leggings I'd grab some from a nearby Walmart for six bucks. This makes me think she had no intention of paying for herself until she realized you weren't footing the bill.

    Just my assumption. You what what they say about those who assume. :p

    1. That seems like the most reasonable explination for her behavior.

    2. Eh, I disagree. Guys always think that women take forever to shop. My brother used to get irritated while shopping with me, because if he saw something he liked, he would just buy it, whereas I would take the time to actually try it on, see if I could find something similar for a cheaper price, check to see if it came in any other colors, etc. His constant complaint was that I took too long, but I actually don't even take that long to shop: when shopping with my girl friends, I was usually the one who had to wait because they took much longer to shop than I did.

      Also, I personally detest WalMart, and if there's a Macy's around, I'd rather buy leggings from there than from WalMart. If I'm going to pay for clothing, I'd prefer to pay a little more (Macy's clearance rack is not really not that much more expensive than WalMart) and get something that I can actually wear more than once.

      I think this one is pretty simple: yet another case of a person pulling out their fetish on the first date and expecting the other person to go along with it. Women who like to see their guy dress up in women's clothing or underwear is not an unusual fetish.

  8. Maybe she just wanted you in that skirt so she could ask you to reach something on the top shelf for her.

    NSFW warning.


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