At this point, my sister was in college and was living in a dorm during the week. On weekends, however, she would come home usually from Friday night till Sunday night. We’d moved on from our childhood fighting and had a decent friendship. Usually during the week we would text back and forth about something fun for us to do together on the weekend.
I was at a point where I really just wanted to admit to her that I was wearing panties. I was very tired of keeping it a secret, and I was so comfortable with it that I didn’t think it would be a big deal to her. I was no longer wearing her panties, which I think may have freaked her out, so I thought she would be fine with it.
I just had no idea how to tell her. I wasn’t just going to come right out and say it. And any thoughts I had to intentionally have her catch me in panties just felt forced. So I eventually had the idea these weekly text conversations might be my best chance. It was easier to type it to her than to say it to her.
One week after she texted me asking if I had any ideas for something to do on Saturday afternoon, I responded that it might not be the most exciting thing, but I needed to go clothes shopping. That was the set-up I had fantasized about using to start the conversation, and I’d finally put it out there. I was hoping I had the courage to complete it.
her response: not a bad idea actually, I need clothes too. Were you thinking we’d go to the mall?
me: yeah, the mall would be good. I need a little of everything haha
her: I mostly need jeans and bras lol
I was so excited that she brought the conversation to underwear without me needing to push it that direction. I wasn’t going to pass up on the opening.
me: where you do buy bras? I really need underwear too
her: theres a bra store at the pru center that I like. I forget what it’s called. It literally only sells bras lol
me: haha not even panties? Just bras?
her: I think they may have a few panties but really theyre all about bras
I had never imagined that within a few short texts we would already be talking about panties. This was going much better than I expected.
me: I’m sure there is a place I can buy underwear at the pru
her: no doubt. where do you usually buy them?
me: I wear a lot of jockey, but I’m not picky.
This was a completely true statement, although I had a lot of panties from various places, I was particularly fond of the Jockey brand.
her: don’t know if there’s one there.
me: I’ll find out.
Some time passed. I had felt like we were close, but I hadn’t quite confessed anything. I was trying to think of the right thing to say that would lead to me admitting it. Finally I decided to say this, with the intention of sounding playful:
me: No jockey store there, I checked. Maybe I’ll just shop at your bra store haha
her: definitely no mens underwear there lol. and maybe only like 5 types of panties.
me: you don’t wear their panties, even as much as you like their bras?
her: honestly never considered it. bras are their thing. I get panties at Victorias Secret usually.
me: I’m sure the pru has one of those, every mall does
her: most likely, but I don’t need panties really just bras
me: I was thinking more for me
There, I said it. I wasn’t sure if she would pick up on it, but at least I’d gotten it out there, the most direct thing I’d ever said to her about me wearing panties.
her: pretty sure they don’t have mens underwear there either lol
me: I know. they have nice panties though.
I was almost physically shaking with nerves as I sent that. My palms were sweaty. I couldn’t wait to read her response.
her: true. If youre going to buy panties, thats a good choice.
Really? It was almost like she didn’t think anything of it. I wasn’t sure if she was just going along with what she thought was a joke, or if she was being serious.
me: I actually really do prefer Jockey panties, but VS is nice too.
Nerves again, I made it even more clear that time.
her: I don’t wear jockeys. Don’t think I ever have. Maybe I should try.
I was actually starting to get a little annoyed. Could this be so unimportant to her that she doesn’t even react to the news? Or was she not getting it? Before I could respond, she wrote:
her: this may be the most Ive ever talked to my brother about panties lol. what other brands do you like? lol
me: Maidenform makes some good stuff, but part of me feels like it’s for old ladies haha
her: I had a maidenform bra that I loved! I’d always wanted to get another one, but couldn’t find it again.
me: Too bad there’s not a Maidenform store at the pru.
her: yeah, why do I have a feeling we’re going to be spending the whole day shopping for underwear? And we haven’t even figured out where to get mens underwear.
Well, I guess that explained it. I came to the conclusion she was thinking I was just expressing my opinion about panties, not that I was wearing them. I thought I had made it clear, but maybe she just wasn’t reading my words too carefully.
me: meh, no need to find men’s underwear
her: just panties for you? lol
me: pretty much. Is that weird?
I thought asking that direct question would probably drive the point home, and I was right.
her: that you like panties? or that you wear panties?
me: both I guess.
her: Do you really wear them?
me: yeah, I kind of thought you knew.
Not sure why I said that, because I didn’t think she knew.
her: honestly I don’t give much thought to your underwear lol
me: probably a good thing haha
her: we can definitely go panties shopping for you, doesn’t bother me at all
Well, that went about as good as possible, even thought it took longer than expected.
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