Friday, May 24, 2024

A Tough Question, A Tougher Answer

Whenever I tell my trans life story, I always mention that I never told my wife about my crossdressing before we were married because I bought into the old wives’ tale that marriage would cure me.

When I did come out to my wife after we were married, she was initially supportive, but less so as the years passed. Meanwhile, I became better at crossdressing mainly due to her suggestion that I seek out a support group, which taught me how to be a better crossdresser. Regardless, I enjoy crossdressing a lot and would do it more often, but I still feel guilty for not telling her before we got married (41 years later), so I only crossdress a few times a month in deference to her.

During outreach a few years ago, a female asked me if I could do it over again and told my wife about my crossdressing before marriage and as a result, she dumped me, what would I do? Would I continue dating and try to find a woman that accepted my crossdressing? Or what?

That was a very thoughtful question and a difficult one to answer quickly. I replied that if I could do it over again and my wife rejected me before marriage because of my crossdressing*, then I probably would continue looking. I know that such a woman would be very hard to find and that I would probably be unsuccessful, give up and live full-time as a woman.

Truthfully, if I had to do it over again, I would live full-time as a woman and skip the formalities of searching fruitlessly for a woman that accepted me. If one came along, that would be great, but I would not put a lot of effort into finding Ms. Right.

Recently, there was a survey asking “what woman you'd actually want to be?” There were a wide variety of answers, but mine was unique: "Stana - I very much like the woman I am when I crossdress. If I could live as Stana full-time, I think I would be one heck of a woman and would not want to be anyone else.”

I really believe that!

So, do I owe it to myself to live the way I want to live? Should I burn all my bridges behind me and start living as a woman on a full-time basis? Do I abandon my commitment to my wife and become the woman I want to be? We only go around once. I won't have this opportunity again. I just don't know.

* By the way, I asked my wife if she would have dumped me if I had told her about my crossdressing before we were married and she replied that she probably would have stuck with me anyway. 

Source: Boston Proper
Wearing Boston Proper

Bert Wheeler
Bert Wheeler femulating in the 1931 film Peach O’Reno.


  1. AnonymousMay 24, 2024

    You're right, there's a lot to unpack here, which is why I see a therapist lol. But there's one point you made that I completely agree with. We would have made fantastic women! Society really missed out by not having us experience life from that perspective.---Paula G

  2. You brought it up, so here's my 2 cents worth.
    I have always said no one should enter into a marriage relationship with secrets. Breaking off an engagement is easier than getting a divorce, so I always advocate for telling her right from the start about your crossdressing. I have been married twice, and in both relationships I was honest up front. The first one ended when she decided that she "thought" she was OK with my dressing, but after 14 yars decided that she wasn't. My current relationship is alive and well - 26 years and still going - as long as I don't ask her to participate in Julie's life.
    I know it can be scary sharing our innermost feelings and predilictions, but you owe it to the other person to be honest.
    I'll get off my soapbox now . (smile)

  3. AnonymousMay 24, 2024

    That is sure the conundrum that many of us face. If we only knew then what we know now. I've been grappling with this for years and I still haven't found the answer. At times, it leaves me unsettled for sure.


  4. AnonymousMay 24, 2024

    My wife and I have been married for 50+ years. Before I proposed in a short whirlwind courtship the question did run through my mind whether I should disclose that I had worn my mother's clothing in the past, before I outgrew them. I had not worn any female attire for many years. She and I met after I had returned from Vietnam as a combat infantryman with a Purple Heart w/Oak Leaf Cluster. When my desires arose after the "I do's" she did say she would not have married me if she had known before. She wants nothing to with "her." "If I wanted to be married to a woman, I would have married a woman," she said. She suggested I find a support group. There were none in our area. She did not dump me because she also had deep dark secrets that, had those secrets been disclosed I would, some guys would have run for the hills. I can truthfully say her secrets, which still remain undisclosed, have affected our marriage more than my cross dressing desires. I guess she and I are both somewhat guilty of "lying by omission."

  5. AnonymousMay 24, 2024

    Like Stana said, I believed I'd lose any interest in crossdressing once I became a husband. Eventually I told my wife. She accepted it, but did not want it to be part of our lives together.

    For years I snuck my crossdressing in this don't ask don't tell atmosphere. Eventually, I stopped because I didn't enjoy the sneaking around and I was fearful the kids would discover my stuff. Most of my CDing was in private. I went to a couple of CD functions.

    Recently, after numerous years in "drab" I put on a pair of pantyhose and a dress just because I missed it so much. It felt nice, but who knows when I'll ever do that again.

    If a woman objects to a partner crossdressing the way some of us do I understand their feelings. These are tough questions without any one size fits all answers.

    I don't know what would have happened had I told my wife before marriage about this side of me. I know if I were suddenly single I'd find myself attracted to women and once again I'd be afraid of revealing that side of me.

    You might say that I haven't learned anything in my seventy years on this planet, but truly I don't know why I do it and sometimes I wish I didn't. Sometimes I've hoped that once I find myself no longer living that all thoughts of crossdressing will finally leave my mind.


  6. I have had three wives and the first two knew I was a cross dresser going into the relationship but I outgrew them and discovered I was transgender and wanted to live fulltime as a woman. My second wife was against me starting gender affirming hormones before she passed away suddenly following twenty five years of marriage.
    My third wife who came along quite unexpectedly told me she had only seen female in me which solved all my issues and I am very grateful

  7. I as a man have been on injectable estradiol valerate for the past 13 years and have acquired a feminine appearance, including a bust. My hair is beyond shoulder length.
    I wear dresses the great majority of the time. That include shopping, church, doctor appointments, etc. My dear wife passed away in April 2023 and she accepted me with what I was except she wanted me to wear men's clothing when I went out publicly with her. So if I find the right woman to be my wife I won't have any secrets with regard to my presentation to divulge.
    And yes, I still regard myself as a man and I have a deep masculine voice as I sing second bass in my church choir.


  8. AnonymousMay 24, 2024

    Also, I love that Boston Proper outfit!!


  9. AnonymousMay 24, 2024

    when you woulda-shoulda-coulda you are forgetting how different things were (if you're over 60) back then as compared to now.not only was society very negative about us but we also lacked the info which is available now

  10. AnonymousMay 25, 2024

    That is the ultimate question, to tell someone before marriage and risk losing her, or risk a divorce if you tell her after marriage; I opted for disclosure before marriage, and she was OK with it, but gradually faded over time, thinking it was just a phase I was in ... it never has been a phase, its a perspective on life; so I gradually dressed less, but the longing was still there ... If I had to do it over again, especially with younger people now more accepting in many settings, I probably would come out discretely but regularly on weekends, becoming identified more solidly with the LBGT community, and seeking an accepting female of a male having a 3rd sex personality.
    ... Your blog is wonderful ! Keep at it, you do great work for a welcoming and an accepting community, regardless where you start out life as

  11. AnonymousMay 25, 2024

    Too true. In the seventies I definitely wanted to cross-dress, but there was no information. I didn't even know it was a thing.
    Penny from Cambridge