When my wife first told me she wanted to start wearing men’s underwear, I remember being fully opposed to the idea. But I slowly warmed up to it. It would be obviously hypocritical of me to have a problem with it considering she was completely fine with me wearing women’s underwear. If anything, she encouraged me to do it. So I felt like I had to reciprocate.
I had this image of my head of her in white men’s briefs and I kind of liked it. Unfortunately she gravitated toward boxer briefs which I found much less sexy on her. But I think this whole experience was a turning point in our individual and joint gender discoveries. When I was wearing panties it seemed like a sexual fetish, but now that both of us were wearing the “wrong” underwear, it felt more like a thing.
There was some weird pleasure I got from washing and folding our laundry, knowing that all the men’s underwear was for her and all the women’s underwear was for me.
At the same time that she stopped panties, she also switched from normal bras to wearing exclusively boring unsexy sports bras. She made this change without mentioning it to me and I remember being a little disappointed because I’ve always liked bras.
One day when we were shopping in the lingerie section of a department store for new underwear for me, I picked up a very feminine lacy bra and suggested it to her. Rather than directly respond to my encouragement, she commented about how she hated bras and wished she didn’t have to wear them. I told her that I liked them, and she responded, “You should wear them then.”
I’m not sure if she put the idea in my head or if it was already there, but not long after that I sheepishly told her one day that I’d like to start wearing bras. Her response was not what I’d been expecting. She said, “If you’re going to do that, you have to do it right. We’ll need to have rules.” As a submissive, I’ve always been a sucker for rules.
The rules we came up with were that I couldn’t wears bras only when I felt like it, but I had to wear them the same way a woman would. This meant never leaving the house without a bra. She said I could take my bra off when hanging out at home but only if we didn’t have plans to head out later. She also talked about not wearing the same bra for two days in a row to allow the elastic to rest and the importance of washing bras by hand (even though she never did that with her own bras). We agreed that I would need a minimum of three bras before I could even realistically start wearing them.
Back then it wasn’t as easy to find obscure bra sizes as it is these days online, so it took a little searching to find bras I liked in my size 36A. The more obscure the size, the higher the price, so it was also an expensive endeavor to get myself a collection and start wearing them.
The rules weren’t that difficult to follow. The tricky part was that it limited how I could dress, in the sense that I never wanted it to be obvious that I was wearing a bra in public. I could no longer just throw on a tshirt because the bra underneath would be way too apparent. I started wearing tight-fitting camisoles over my bras and under my dress shirts so I could wear bras to work. I actually found myself looking forward to the cooler weather because more layers meant I had more options for how I could dress.
It wasn’t until the springtime when we started talking about going to the beach that she reminded me that I could no longer be shirtless. This was an issue I hadn’t thought of. I asked if I could just wear a t-shirt on the beach and she said only if I had something covering my top under the tshirt. So that became my plan, some kind of tankini with a t-shirt on top. It was an awkward way to dress in public but I really doubt anyone paid much attention to me.
Over the course of the summer I got more comfortable with it and started wearing only the tankini top on the beach, which was easily the most public cross dressing I had ever done up until that point. It felt like a turning point in helping me feel more comfortable with it.
The next big step came when we stopped at a grocery store on the way home from the beach and realized only after we walked into the store that neither of us had our wallets with us. We were dressed for the beach and had left them in the car in our pants pockets. My wife had stopped carrying a purse at least five years earlier. She had never really offered an explanation but I knew it was because she felt purses were too feminine.
I retrieved my wallet so we could pay, but as we were walking out the store she blurted out her latest idea: “I think you should start carrying a purse so this doesn’t happen again.”
There were admittedly regular instances of inconvenience that would have been solved by things that she normally would have had in her purse, so the idea of one of us carrying a bag filled with random essentials seemed like a good idea. And I knew it wasn’t going to be her.
I had no choice but to agree. The rules we came up with were that we would pick out the purse together but she would have final say. She wanted me to get something that was definitely a woman’s purse, not a bag that would be seem appropriate for a man. I would have to carry it at all times when we were out together. I would have to take it with me to work but I would be allowed to leave it in the car. Same if I was headed out with friends. The exception was if I was with both friends AND her, in which case I would have to carry the purse with me.
I had noticed over the time that all this was happening that my wife’s wardrobe had gotten decidedly more masculine. This meant that a lot of her more feminine clothing was sitting in her closet not being worn. So one afternoon when we were headed out somewhere and I had complained about not having any clean jeans to wear, she produced a pair for me out of her closet.
We were fortunately approximately the same size, and other than the jeans being slightly too short for me, they fit perfectly. They fit almost too well. I found them extremely comfortable, and I told her so. She told me she didn’t wear them anymore and I could keep them as my own. This began a slow progression of me taking more and more of the clothes she no longer wore.
So it happened somewhat organically and definitely unplanned on my part that I eventually realized that I was wearing 90% women’s clothing and she was wearing 90% men’s clothing. Maybe it was more planned on her part than on mine.
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