Ask Hannah!

I am pretty much out, my wife knows as I told her within 2 weeks after we started seeing each other which was 6 years ago and is fully supportive, some friends and family know and again have all been amazing. I also now do not care who knows about this side of me which I have only really accepted since meeting my current wife so it is thanks to her.


I have crossdressed for around 45 years, I’m now 59. The issue I have is the older I am getting the stronger and more I want to be Steph. Almost to the point where I’m thinking as you do that I’m possibly transgender. I don’t think I want to fully transition but feel more comfortable now as Steph. I have also always wanted my own breasts and absolutely hate having any body hair so that is always removed. It also feels much nicer not having any.


My main concern is will this continue to get stronger the older I get and want to transition fully?
How do you feel in yourself the older you get and is this something that you have or are experiencing?

Well, since you’re asking me, and for what it’s worth, I think almost all of us are transgender. My definition of ‘transgender’ is admittingly rather broad and I think it’s kind of an umbrella term. I think it encompasses anyone who identifies as gender non-conforming, non-binary, crossdresser, gender queer…

But the word isn’t as intimidating as many feel it is. Identifying as transgender doesn’t really have to mean, well, anything. It doesn’t feel transitioning, it doesn’t mean estrogen, it doesn’t mean legally changing your name or gender on your drivers license.

I’ve identified as transgender for over ten years and the needle hasn’t even twitched when it comes to making any physical or legal changes. 

Regarding your question about this feeling become stronger as you get older, I suppose it’s possible. Only you can make that decision. 

As for myself, I don’t feel that transitioning is right for me. I didn’t feel it was ten years ago, I didn’t feel it was twenty years ago, or, well, ever. I have no idea what the future holds but I really don’t see myself transitioning.

If you aren’t already, I absolutely encourage you to talk with a therapist. They will get to know YOU and will help you navigate your feelings. I feel they would be more helpful in such an important decision than I could ever be.

Love, Hannah

Have a question for me?  Oh yes you do.  Ask me here!

6 thoughts on “Ask Hannah!

  1. Hi Hannah

    Firstly I’d like to thank you for taking the time and replying to my message.

    In regards to your reply, I’d have to agree with all of it.
    I don’t feel that I want to transition fully along with I do not hate my body which from what I have read from others who are struggling hate their body or parts of it. They also want to be known as the opposite gender which again doesn’t apply to me.

    I think my main issue is I need to actually go out as Steph more which is something you seem to do quite frequently.

    A couple my wife and I know who we are good friends with have recently found out when I told them last August about this side of me hoping they’d be fine about it and have been amazing.
    We take it in turns every 6 weeks or so in spending a Saturday evening at each others house for a catch up and drink etc.

    They really wanted to meet Steph which was a completely new experience for me. So far I have been to theirs once as Steph which was the first time they met her and the next when they came to ours.
    I must say it really was such a wonderful experience. I felt on top of the world.
    Anyway the couples names are Ann and Mike.
    After Ann met Steph she was amazed and gave me such lovely compliments. Followed by

    “When are we going shopping then”

    I was gobsmacked and said really, you’d go with me. To which she replied of course she’d be honoured to.
    This is something I need to arrange and my wife would also like to go.

    So now I’m banging on but just wanted to reply to you and explain what I think my main issue is.
    Which really is down to the fact I want to go out as Steph more, for evenings out, shopping and what ever else us girls can do.

    So thank you again. I would include a couple of photos of me so you can put a face to my name but there isn’t an option for that.
    I can always send you a couple via email if you’d like.

    Thank you again Hannah and love your outlook on everything.

    Take care

    Love Steph

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  2. To be honest, it has been your definition of Transgender that was so instrumental in helping me become comfortable in my identity as a transgender person. Obviously, we’ve taken quite different paths when it comes to transitioning, but I fully agree with you.
    Once again, you’ve hit it out of the park Hannah!

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  3. You speak so much about transgender, correct me if I’m wrong but a person that just loves to dress up is not transgender, you have to have that special feeling to know your in the wrong body , mtf. FTM ? Transgender isn’t based on clothing , likes or dislikes . It’s the fact that one’s mind is totally different from there anatomy . Because your feelings change when your dressed up does not make you transgender . Your thoughts ?

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    1. My definition of the T word is pretty broad and I don’t feel that identifying as transgender means you feel you are in the wrong body. I linked to two different posts in my answer that expands on my perspective more.

      Love, Hannah

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  4. I’m on a different path, or at least a different outcome. I, too, had been crossdressing for decades. And I was finding it harder and harder to switch back when work, and the drab life, returned on Mondays. Like you, I had told my wife early on. We spent time out doing things on a part-time basis, but never with family or friends. We had 40 years together before they passed. I had started seeing a good gender therapist only a few months before their cancer diagnosis, so my transition was on hold while we were treating her. I never hated my body, at least in total. I couldn’t stand hair – body or facial – and had already been dealing with that long before my gender dysphoria diagnosis. And until that was mostly gone, I didn’t realize that other body parts didn’t feel right. Not “hated”, but not right. Now, as I approach 65 I am feeling so good about myself. Two surgeries down, and maybe one to go. I am loving life, loving living authentically, and happier than I thought possible. I can’t say that my path, or my outcome, is right for you, or anyone else. All I know is that this has been right for me.

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  5. Its not the sort of question that you can get an answer to unless you actually to do it!

    If you never transition you will always wonder what have I missed!

    If you do transition you will always wonder if it was worth it and what you may have missed out.

    What ever you decide to do, its your choice and nobody else’s. Good luck in making the right choice

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