Well, I told my girlfriend today that I was interested in ‘dressing up’. Initially she was shocked. And, she jumped to the conclusion that I was gay, or at least bisexual. I spoke with her about it, and gave her the facts: most (90%) of crossdressing males are straight. I was a little put off that she jumped to that conclusion, and when she realized this, she understood and felt better.
Then, she asked what exactly I wanted to wear. She offered me her clothes, and I declined, thinking it would be strange to wear her clothes (although, she did accurately mention that we’re about the same size; we’ve worn each other’s pants before). I actually ordered two outfits from a Chinese store for about $15 (two skirts, two tops, stockings). She doesn’t know this yet, but she’ll find out when the package arrives (since I also ordered some clothes for her).
I told her that I wanted her to know all of this information so that she doesn’t freak out if she comes over and sees something that would make her uncomfortable. She responded with ‘Well, if I saw you wearing frilly panties, I’d probably freak out.’ I paused during this moment, and she kinda caught me. She then said ‘Do you plan on going that far?’ I replied with ‘Yeah probably…’
By the end of the conversation, she said that she will still love me regardless. I can do what I like and she will accept it. “Even if it is wearing women’s underwear.” Although she accepts it, I feel she’s still a bit uncomfortable about it. But, I think over time she will be okay with it. It’s been about two weeks since I’ve worn my boxers, and I don’t really intend on going back.
With that in mind, I’m actually wearing a pair I got in the mail today. :) I will be seeing her tomorrow, and we’ll probably get lunch. I’m almost 100% certain she’ll ask me if I’m wearing panties. We’ll see how that goes!