My entire life, I have enjoyed wearing women’s clothing whenever I’ve had the chance, but until recently I always kept it a closely guarded secret, never telling anyone and avoiding the subject if anyone ever found or observed anything suspicious (which happened a few times). My wife, was no exception.
At the time of me writing this post, my wife and I have been together for the better part of a decade. There were many times I thought about and even wanted to tell her, but I was afraid. I was afraid that telling her would cause her to look at me differently, or cause her to break up with me (or divorce me, which was the worry after we got married, obviously :p) and I was terrified of telling her, her leaving me and then having to figure out what to tell people when they inevitably asked why we were no longer together. This fear caused me to keep this part of my self, this huge, important part of myself, hidden from her for nearly 8 years. Every time I wanted to tell her, I got close enough to doing so that I started to feel like I was going to have an anxiety attack and I would end up not doing it. Each time this happened, I realized that the longer it took for me to tell her the more of a risk I would be taking, as the longer we were together the larger a chunk of my life I would have to learn to put behind me and learn to somehow move on from.
Then, fairly recently, I got to the point where I began to realize I couldn’t hold off telling her any longer than I already had. A couple of years ago, I was digging through our closet when I came across an old bra of my wife’s. I remembered her wearing it when we first started dating, but once I came across it on this particular day I realized that she hadn’t worn it in a very, very long time and had recently purchased a couple of new bras. It did not take long for me to conclude that she wouldn’t miss it, and so I took it, stashing it in a plastic storage bin that slides under our bed. Neither of us really use it, so it was the perfect hiding place for the bra (I decided I had to hide it in case she decided to throw it away, which is what I was hoping she would assume she must have already done if she discovered it was gone). For a while, wearing this bra while I was home alone sufficed rather nicely. Then, around the end of last year, I started to realize that this wasn’t going to be enough for much longer. Shortly after the new year, I went to Wal-Mart one morning when there was very few people in the store and after hovering around the general area for a while, finally went down the bra and pantie isle and grabbed an eight pack of silk, bikini bottom style panties.
For a week or so, the panties and the bra seemed enough, but only barely. Then, I realized that this still wasn’t enough, and at this point I realized I absolutely had to tell my wife, as going any further would involve either using her makeup (which I assumed she would notice was suddenly depleting quicker than usual) or, more preferably, I would have to start buying my own makeup (which again I figured she would notice, as makeup doesn’t have the natural tendency to randomly experience mitosis). I also realized I wanted to have a change or two of women’s clothing that I could wear, which again I thought would be rather difficult to hide and more importantly, if found would cause an extremely more awkward situation as I imagine she would assume that I was cheating and the clothes belonged to whatever “tramp” I’d brought home that was too dumb to remember to grab her clothes as she left. I had to tell my wife, I absolutely had too.
I started doing Google searches related to coming out to your girlfriend/wife about crossdressing (a term I use her for simplicity, I have VERY mixed emotions about the word “crossdressing”, but I’ll save that for another day). Everything I was reading involved long, slow methods that would take a very long time to build up to telling her you like to wear women’s clothing. The most common suggestion I was finding involved first talking to your wife about spicing things up in the bedroom by introducing toys and, more specifically, lingerie. If she went for it, then you would eventually get her to sleep in the lingerie, holding her close and playing with the fabric as you both fall asleep. The idea would be to get her to realize that you like the way the material feels, and then you would more or less hope that she would someday ask for you to try it on and then you would keep building from there.
There is nothing inherently wrong with this approach, but it has too many cons for me. First of all, it would take way too long. My desire to be able to more or less openly explore my feminine side was getting too strong for such patience. Also, if your wife isn’t comfortable with her body, then you could quickly run into the problem of her not wanting to wear lingerie, which seems to instantly put a hole in this plan. Next, you more or less wait for her to have the idea of you trying on the lingerie. Even if you hinted towards liking the feel of the fabric or even hinted towards you wanting to wear it, there is no guarantee that she will ever ask. She may think you would be too embarrassed, or she personally might just not have any interest in seeing a man wearing women’s lingerie. So, as you can see, there are a lot of draw backs to this approach.
What I eventually decided to do was to start “experimenting” with male grooming (or “manscaping”, if you are that type of person). I started by trimming up my pubic hair, she she was very okay with, as I knew she would be. Next, a few days later, I shaved my pubic area so that rather than having well groomed pubes, I was as bald as, well, somebody who had just shaved their pubes! Duh! Anyways, she was okay with this as well, and in fact seemed to rather much enjoy it. The next step was that, again, a few days later I went a bit further and shaved everything from my waist down (and happy trail since that just seemed odd to leave to me, personally). After she got home that night I told her about my legs and she seemed rather okay with that as well. She did have a couple of questions, the most daunting being “Were you just curious?”, so that was a pretty good reaction. Then, once again a few days later, I spent a few hours one night building up the nerve to finally tell her, and after a while, I did.
I brought the subject up slowly, but steadily. I wanted to ease her into it and I wanted to “prep” her for it as much as I could, but I also didn’t want to go so slow with it that I would have the chance to back out of telling her again. When we first started dating we used to go to a local gay bar on Monday nights to watch the drag show, so I knew she was okay with the idea of men wearing women’s clothing, but thought that it being her husband might be different. I have also always been very open with her about my sexual orientation, which is that I am attracted to both men and women, but have never developed an emotional bond with another male like I have with females. I have also always been a little feminine with the way I sit and carry myself (to the point that when I first came out to my friends as being bi as a teenager, more than a few of them were not very surprised, but others were completely shocked and one had the audacity to tell me I was merely confused).
When the conversation started, she could tell there was something on my mind and had asked a few times what I was thinking about. I finally got up the nerve and started opening up about it. I don’t remember the conversation word for word, but it essentially went as follows:
Me: So… There is something I’ve been wanting to talk to you about.
Me: Have you ever noticed that I have a bit of a feminine side?
Me: Well… its not just a bit of a feminine side. I have a kind of big feminine side and there is something I do when I am alone that I wanted to talk to you about.
Her: Okay… what is it?
Me (After a short pause as I tried to find the right words): Remember when we first started dating and we would go to the drag shows?
Me: Well its kind of like that…
Her: How so?
Me: When I am alone I like to… dress up…
Then came the greatest response I have ever heard to anything I’ve ever said, she said: Okay.
“Okay.” Not, “Okay?”, not “Okay…”, just… okay. Short, accepting, loving and simply, okay.
From there, she asked a few questions and I told her about wearing her bra (funny story, she had forgotten all about that bra until she asked which one it was and I described it). She told me that it didn’t change how she felt about me at all and I wish I could have honestly said the same, but really the experience made me love and cherish her so much more than I already had. After fearing the worst and receiving the best response I could ever have hoped for, every reason I love my wife was instantly confirmed; she is one of the most caring and accepting people I have ever met, she is intelligent, funny and the greatest partner I have ever had or ever could have in my entire life.
We concluded that while she is perfectly okay with my exploring and indulging this feminine side of myself, she wants to be eased into it, and so that is what we have been doing so far. She has seen every article of clothing that I own and I put on my first outfit and showed her once, though I didn’t wear a bra under the shirt to do so because I didn’t want to pop in my “breasts” (more on that later) as I thought that would be too much too soon, especially since this was only a few days after I bought the outfit, which I purchased the day after telling her about my wearing women’s clothing and wanting to do so on a larger level. Since then I have started to wear boxers only when going to work or going out, around home I wear panties most of the time and I have worn them to bed a couple of times and I wore my skinny jeans in front of her one other time, but that is it so far. We talk about it and I even ask her questions about make up and clothing, but we seem to be going at a pace that works for both of us, and that is the important part.
When I find myself home alone and know that I am going to be for a decent amount of time, I throw on my jeans or skirt, do my makeup, throw on my bra and shirt and slip into my wig and then I just feel… comfortable.
If you are in a relationship and you want to tell your partner about your longing to wear clothes intended for the opposite sex you were given at birth, tell them. There are horror stories out there about these things going terribly, terribly badly, but there are many more cases of when the person’s partner is accepting of it. One story I read before telling my wife, and I wish I had a link to share so you could read the story as well, a man told his wife he wanted to start wearing women’s clothing. Her response was that she immediately took him shopping, buying him several hundred dollars worth of clothing, makeup and other necessities. Obviously, this is an extreme example of how well the situation can play out, and you shouldn’t expect this to happen when you tell your wife (or husband if you are a woman wanting to dress as a man), but it is a story worth noting for two reasons: 1 it is nice to know that you never know how they will react, so even though you are frightened and think they might reject you, there is always the possibility that they will have a reaction better than you ever could have imagined, and 2, its a friggin’ awesome story!
It is frightening to think you might be rejected for simply wanting to express yourself, but the reward often outweighs the risk. If my wife would have rejected the idea, and had the worst case scenario played out and she had left me, I would have been devastated, I would have been broken, but I would have had the knowledge that I was rejected for wanting to be me, and as I would never ask my wife to change anything about herself, and because I accept and love my wife for everything about her, I expect the same in return.
But telling your partner and them accepting it is amazing and to all of you reading this who are thinking about telling their partners, I hope you do and I sincerely hope you receive the caring, loving and accepting response you deserve. If you don’t, I am truly sorry, but I ask that you remember that you are not alone and that because it didn’t work out this time, there is no reason to believe you will not find someone who will accept and love you for everything that makes you you and unique.
Stay beautiful, all of you.