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Life In Bed, part 2: cross dressing

posted 6/2/2008 5:01:40 PM |
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tagged: relationships, drag, panties, cross dressing

Him: What is that you’re wearing?
Her: Your boxers and one of your t-shirts.
Him: It’s not very flattering on you.
Her: It’s not meant to be, it’s just something comfortable to wear to bed. What’s your problem with it?
Him: I like girls to be girls, not cross dressing!
Her: This isn’t cross dressing.
Him: Of course it’s cross dressing… you’re wearing the opposite gender’s clothing. Isn’t that the definition of cross dressing?
Her: Yeah, but this is different. It’s not like a man wearing a dress.
Him: Why is it different? It’s such a double standard. Why is it acceptable for women to wear men’s clothing, but men can’t wear women’s clothing?
Her: I don’t know. Maybe it’s because men who wear women’s clothing look ridiculous.
Him: Well I just told you as much about what you’re wearing.
Her: No, you said this wasn’t flattering, you didn’t say it looked ridiculous… it’s not the same.
Him: Still, it’s not fair.
Her: Why, do you want to wear girl’s clothes? Have you ever cross dressed before?
Him: No, and no.
Her: Come on… you’re telling me that you never tried on your sister’s bra or dresses when you were little and knew you’d never be found out?
Him: Well….
Her: Ha, I knew it. Every guy I’ve dated has admitted to trying on a bra or panties at least once. You can try on my underwear if you want, I really don’t mind.
Him: Gee, I don’t know. Don’t you think I would look rather, let’s see… ridiculous?
Her: Ha, ha. Seriously though, we should totally get you all dolled up. We can paint your nails, do your hair, make-up… we could have a girls’ night in.
Him: I really have no desire to be “all dolled up”. Any interest I have in cross dressing lies only in the underwear.
Her: Fine, then you can wear a pair of my panties tomorrow.
Him: As much as I would love to parade around in your underwear, I’m pretty sure they wouldn’t fit me.
Her: Well, we will buy you some panties next time we are out. Are you a Hanes or Victoria’s Secret kind of girl?
Him: Definitely, Victoria’s! However, I’m not interested in brand new store bought panties.
Her: Why not?
Him: Well, the desire I have to wear women’s underwear lies purely in being sexually stimulated by it, not because of any gender questioning issue. Thus, I would need panties that I could put a pretty face to… as well as a pretty pussy and pretty butt. In other words, they would have to be used panties from a pretty girl.
Her: Right. And would they have to be dirty, or is clean acceptable?
Him: Clean is acceptable… but dirty panties are more exciting!
Her: Ugh, you never cease to amaze me.
Him: You said the word amaze, but somehow I think another word was in your head.
Her: And how exactly do you plan on going about obtaining these used, preferably dirty panties from a pretty girl that would have to be your size?
Him: You can ask some of your friends. I think Katie or Melanie might be my size.
Her: Oh really. And it doesn’t occur to you that it would be entirely awkward for me to ask them for their panties because you want to wear them?
Him: Eh, looks like I will be pantyless for the foreseeable future then.
Her: I really do want to paint your toenails though. We will do it tomorrow. Do you want red or blue?
Him: Blue. If I have to have my toenails painted I may as well save myself some dignity and choose a masculine colour.

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Life In Bed, part 2: cross dressing
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Jun 3 @ 2:16AM  
Her: I really do want to paint your toenails though. We will do it tomorrow. Do you want red or blue?
Him: Blue. If I have to have my toenails painted I may as well save myself some dignity and choose a masculine colour.

I have painted mine red, pink, and purple before...

Good story!

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Life In Bed, part 2: cross dressing