So I am 30 years old and have been dressing (primarily in stockings and high heels) for about 18 years.
It took me a while to figure out exactly who I was, but by my mid-20s I kind of figured it out. I'm a straight man who basically feels sexy to wear skirts and stockings and high heels, and that while unusual, and perhaps socially unacceptable, there is nothing ethically or morally wrong with that. So from that point (about 5-6 years ago) I would basically wear these kinds of things occasionally at home alone. Even in that case it wasn't all the time, maybe a couple hours once a week.
I started dating my wife 5 years ago and I did not initially tell her about this. One time after we had been dating for about a year she discovered my shoes. I explained to her what it was about and she said that she was very uncomfortable with that and asked me if I could stop doing that. At the time I was very much in love with her and figured it wasn't really a big deal to me, so I said sure.
A few months later though I started up again, just occasionally, and only when I was alone, but I didn't tell her.
This continued on in this way for about another year and a half, during which time we got married.
few months into our marriage there was one night where a bunch of things had happened and we were basically trying to come clean to each other about everything. In short we had both cheated on each other while dating before we were married, but only sexual flings and we both only wanted each other.
Perhaps because she was feeling guilty and starting on a clean slate, she asked me about my dressing and said that maybe she could try to see if she could deal with it.
So we tried it for a week. I never got fully dressed around her but I did shave my legs and wear high heels around her. I even ordered a cocktrail dress. (Prior to that the only thing I had in the way of women's clothes was cheap French maid's outfit I had worn for Halloween years earlier.) After a week she said she couldn't deal with it. She said she loved my hairy legs and that she just couldn't stand to see me in high heels.
From that point and for about a year and a half, up until about a month and a half ago, things existed in kind of a limbo state. She knew I still had my shoes but we didn't talk about it, and I would occasionally wear them when she wasn't around.
In that year and a half I had acquired some new shoes and even a pair of skinny jeans. Also in that year and a half we moved from a conservative part of Florida to Los Angeles (relevant later).
Sometimes when at home alone (which was frequent because she had gotten a job as a flight attendant) I would take pictures and post those pictures to Craigslist (in T4M) saying I was just looking to dress up. I never actually intended to meet a man for that, I just liked the attention and the compliments that were coming my way.
In the most recent 6 months my wife and I had both started working out regularly and we've both gotten much more fit. I've also noticed that when I would dress, I look much slimmer, my legs look sexier, and, even though my chest grew with muscle, it actually filled out the bust area of the dress better than before.
So I was thinking to maybe finally go out. I had dressed and worn high heels at home for a long time, but it had been a dream of mine to actually go outside, feel my feet in my favorite shoes on the street. However, I had never done makeup, have no idea how, and would be DEATHLY afraid of being an obscene object of attention and judging. However, having moved to Los Angeles, I had heard (through some of the people I chatted with on Craigslist) that West Hollywood at night was a pretty fun, accepting, safe, and relatively unassuming place that I could try.
So I made another post on Craigslist, strictly platonic this time, looking for a woman to perhaps help me dress and go out with me (no way I could do this alone). I got a response from this fantastic woman (we'll call her Bev from this point). We passed a few e-mails, and then one night after work we met up just to talk. So we talked about what I wanted, what I hoped to accomplish, and she also had some issues in her own family life (she and I are both married) that I helped her discuss, since she also didn't have anyone else to talk about them with.
Over the couple weeks Bev and I would text a lot about lots of things, most of the time not even dressing and after a very short time it was like we were old friends who'd known each other for years. So we talked about it and I decided I was going to tell my wife about my new friend, including the circumstances under which we met, because I didn't want to have to sneak and secretly hide this really wonderful new friend of mine. I didn't want my wife to think I was sneaking messages to another woman, or that I was cheating on her, and I didn't want to have to lie about Bev. So I told her, and she was not happy about the dressing. But she didn't get totally upset or irrational, but she was kind of surprised and disappointed to hear that I was still dressing up. But she left it there. She was a little bit quiet and distant for the rest of that evening, but the next day she seemed back to normal.
Then a few days later, on a Friday, she got called for a trip. I let Bev know I was free and she said, "Great, let's go out tonight!"
So she came over, she helped me do some makeup, which I did NOT have high expectations for, but came out better than expected, got dressed up, I had a couple shots before heading out, and we went out to some bars in West Hollywood, starting with Hamburger Mary's. We had a blast! We drank, we talked, we joked, we walked, we bar hopped, it was a fun night all around. I felt sexy dressed that way and wearing those shoes, but even aside from that I had found this awesome new drinking buddy (Bev is ex-military, so she can drink).
(One surprising side effect, Monday at work (dressed as a man of course), which was my first time in a public place again since dressing up and going out, I was surprised to feel that I actually felt more secure and confident in myself AS A man. Perhaps having that outlet to express my feminine side allowed me to ease some of my insecurities.)
The next day, after my wife came back, I told her about it and she was very upset. I tried to talk to her about it, tried to understand where she was coming from, what bothered her about it. I tried to explain that this was something that was a part of me, that it was an activity, a completely safe activity (safe from the perspective that it's not cheating with a person, this activity isn't a threat to our marriage and doesn't bring risk of STDs etc) that I enjoyed, but that I understand that she would be uncomfortable seeing me as anything but a man. I said, I would only do it occasoinally, perhaps once a month, and only when she was gone anyway, so that way she wouldn't have to see me, wouldn't have to help or support me, and also, when she was home, I wouldn't leave her to go do that. But despite all this she just seemed to get angrier and said "You can NEVER "talk" me over this, I will NEVER be ok with this!" It got to the point where I left to take a walk for a couple hours because I was just devastated.
She had cooled off a great deal when I got home and she essentially said briefly, "I guess this is something about you that cannot change. You can do that if you want, but don't tell me about it. I don't want to know about it. Unless I ask you, and then I need you to be totally honest. Also if I happen to find evidence that you had done it, or if I ask and you have, I will be upset. But please just give me a day or two and I'll be over it."
She was much more reasonable than she had been earlier and I felt that maybe we reached a decent state of equilibrium.
Until this weekend. I have still chatted a lot with Bev, and my wife (Jane) knows it. But she also knows I'm not trying to hide anything and I've even offered that she can read our texts if she wants. She has declined, and so I believe she trusts me with Bev from that standpoint. However, it seems that merely mentioning Bev reminds her of my dressing and that begins to upset her. Normally I wouldn't go out of my way to mention Bev, but for example two weeks ago Bev invited me to have lunch with she and her family (they have a daughter). I invited Jane to go with us, but she declined.
So, up till now, I had only dressed up and gone out one time, and that was about a month ago. Since then, I haven't even dressed at home.
Finally this last weekend, on Saturday night, Jane asked me if I could stop dressing for her. I asked her if she NEEDED me to stop, and she said yes. I hesitated. I told her, I've tried to stop in the past. Even if I did stop, I can't stop thinking about it. It's been with me even through my teenage years when I was really religious and thought God cared about such things and I thought it was morally wrong. Even through that I couldn't stop thinking about it and I wouldn't be able to stop thinking about it now. She said but you could stop doing it? I paused and then said "... I could" I asked her then did she also want me to end my friendship with Bev. She asked me if I thought being friends with Bev would make it harder for me to stop. And I said no because while that was the initial reason for our friendship, it's not even something we talk about most of the time. So Jane said, “ok, if you can stop dressing and you and Bev stop talking about that, then I would be willing to meet her and try and make friends with her." I asked her again, "do you NEED me to stop?" and she said yes. I said ok, and I immediately felt deflated. She asked "Are you mad? are you sad?" And I said I wasn't mad but I was sad.
After thinking about that and feeling down all evening, the next morning I said to her, "Why can't you accept this small thing? I'm not talking about a life-change here, I wouldn't dress in front of you, you'd never have to see it or know about it. It would be infrequent (once a month), it wouldn't change our relationship or how I feel about her. I still want to be a man, I'm not looking to have a sex change."
She immediately got upset and turned away from me and said "Fine you can do what you want but I can't say for certain if it will change how I feel about you. Also that you want to continue to do this makes me think you are gay."
Anyway, this is where I'm at now. She has been on a trip the past 3 days and I've just been stewing over this. The fact that she's asked me to stop dressing but that I haven't dressed in almost a month makes me feel like she's creating a much bigger issue in her head than what things really are.
I feel like I'm rationalizing that my request (once a month, only when she wouldn't be around anyway) isn't unreasonable, that she is being somewhat selfish. But I can't help shake the feeling that I'm the one who's being selfish by not considering her feelings.
Can anyone else shed some light or advice onto my situation? Am I being unreasonable? Because I want to know if I am. I actually suggested at one point that maybe we should see a marriage counselor, but she immediately shot that down saying "that would be a waste of money."
-Jenn
up... been there, done that, joined a forum (this one)... took me a few years to get my head around it, but now I help run this place, so it must have worked 
Originally Posted by jennarac
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