This is a really interesting topic.
There's something about the closeness of the relationship and mutual "ownership" (for want of a better word) in having her wear my clothes. lurkette "has" several shirts that used to be mine, and would still fit me, but they live on her side of the closet and she's the only one to wear them in several years. They've sort of become hers.
When she wears them, there's sort of a charge around it for me. Some deep part of my reptile-brain gets tweaked, and thoughts like, "She must love me, she's wearing my clothes." start showing up in my head.
Now, when our girlfriend D wears my clothes, that's just sexy. She wore my bathrobe one morning a few weeks ago and DAMN. It was all I could do not to drag her back to bed. Several months ago (before the sexual part of our relationship had really started, but after we started sleeping in the same bed) she wore a t-shirt and a pair of my boxers to bed. I got very little sleep that night.
Those boxers are still sort of special to me. Every time I see them or (shudder) wear them I think about her.
So the thing to notice is, with lurkette it's about love when she wears my clothes, and with D it's about sex. Which is sort of appropriate, given how those two relationships are right now. Having one of them wear my clothes is a casual expression of closeness and intimacy. It's an expression of the relationship itself.
Why don't I wear either of their clothes? I wouldn't fit. And I don't look very good in skirts or tank tops.
I'd be interested to hear lurkette's take on having D wear her clothes. They share clothes all the time--the other day, the only thing D was wearing that
didn't belong to lurkette was her bra. (They're basically at opposite ends of the Bra Size Spectrum.) I'd like to know how that was for lurkette. I'll PM her and ask her to weigh in.