Life as a Crossdresser is a Series of Small Steps

Part II

This is a continuation of Pondering Life as a Crossdresser.

Last week I began my response to some questions asked by another CDH member. Come with us again as we explore more of those questions that we ponder as we make our way through this transgender life.

Making those changes to our bodies that take us to a more feminine appearance, such as removal of body hair or letting our nails and head hair grow longer, are simple steps to take but can also be a challenge to accomplish without creating problems. My approach to it was to do so in small steps. The first thing I began doing was shaving those areas others rarely or never saw; legs, chest etc. After a while, in winter, I shaved my arms too. Eventually I became so used to it that by the time summer rolled around I was ready to answer questions (with a rubbish but plausible story if necessary) but I was never asked. I can only assume my workmates noticed but never said anything. By taking those steps a little at a time I found that no-one seemed concerned, perhaps just putting it down to a mid-life crisis. The important thing was that I achieved what I wanted to achieve without making waves.

Wearing makeup is another big step, one that is difficult to do well initially because in reality we have not had the upbringing and nurturing that most girls have. Observation and then trial and error is usually the way but thankfully these days there is so much info on line that we can learn from experts with no-one ever the wiser. I love wearing makeup, even when I admit that the time it takes to do well can be a pain. I see it as the step that takes me from my male self in women’s clothes to being Jane. That is especially the case now that I have my ears pierced and have my own long hair. There is not a lot of difference, facially, between Jane and the male me so the makeup is the refining touch.

Being ‘outed’ before one is ready to do so under one’s own terms is a fear many of us have. I managed to survive being exposed by someone else but I believe that the secret is to assess realistically what impact people can have on your life if they find out. For some it’s fear of dismissal from work, or of rejection by friends and family. For others, like me, the realisation that I no longer have a job to lose makes life much easier. I began to tell family members a few at a time so that there wouldn’t be a huge reaction either way. We (my wife and I) also took that approach with friends and told them a few at a time. In fact my wife told more of our friends than I did.

My final ‘outing’ came from a post I agreed to on a public Facebook page, dedicated to suicide prevention. I shared my story in the hope of helping others realise that suicide is not an answer and to encourage them to reach out for help. The post also had a photo so even though it was a couple of years old some people still recognised me from it. Even with all that the response was overwhelmingly positive.

Next week I’ll finish looking at the questions that have vexed many of us over time and hopefully help to provide some answers for those still seeking them.

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  1. Joanne Johnson 1 year ago

    These stories fill me with lots of emotions when I read them. Feeling that I am not alone, how wonderfully people cope, that searching and find your own way is ok. I have been cross dressing on and off for 50 years. I am more accepting now of myself and have a hidden wardrobe of clothes. I am less and less happy as a man. I just get on with it. I feel flat as a man. It’s lovely to put on a bra and panties and pantihose and slip into a dress. Only takes a few minutes. The hurt of not being a female affects me greatly. As I have grown older, it is clear to me that my being male is a mistake. I will be Joanne as often as I can and feel grateful that this website exists and I am in wonderful and loving company.

  2. JENNIFER 2 years ago

    I too, am grateful for this site, talking to others who enjoy wearing nice silky ladies underwear, nylon panties, lace cup bras (44A), lacy garter belts, stockings, (Never Pantyhose!), then sleeping in a lacy nylon nighties and nylon panties, PURE HEAVEN!! Whenever I have to go out, underneath my shirt & pants, I’m wearing lacy pastel nylon pettipants or panties, garter belt, stockings and a matching lace bra. I just wish I could find someone who enjoys the same things, here in Dallas, Texas, I should say “East of Dallas, in Mesquite, Tex.
    Just another ‘young girl’ of 66 years..

  3. marty56 2 years ago

    my dressing is pretty basic…lingerie..under my shirts.. still have a beard,so full dress isnt an option here!.lol..just love the feel of a bra and forms..and wear panties cd’ing was a partial cause of my last present wife washes my girl complaint there!..thankfully!..i havent had a dress on in a cpl years..just enjoying my lingerie!

  4. Jamie 2 years ago

    Thank you Vanessa for such a great site I to am looking for a way to be able to be the woman I want to be.I have been crossdressing when I can and getting ready for makeup lessons and looking forward to be able to fit in.I know I need a lot of encouragement and support and friendship with the other girls on crossdresser Heaven who are in my place also.

  5. Samantha Jane 2 years ago

    Nice story Jane, thanks for sharin. I agree, small steps worm better, u dont have to tell everyone, but havin some support is impt, espec for those who struggle to the point of ponderin ending things. Its a dark place to be, but there is always support. I wish i could go out wearin makeup, but not that point yet. I practice at home, however im findin that i dont always need to be madeup to feel pretty, its the clothing and the attitude. It does look nice though, just dont like to have to take it off again. Maybe it gets easier with practice.

  6. Kelci Norris 2 years ago

    Such incredible insight and commentary by one of the most wonderful women I have ever met.

  7. vvvv 2 years ago

    small step be best for feminine look, due to free from shame. Your friend gradually adjust your look.

  8. jamey Trusty 2 years ago

    Have been crossdressing off and on for years been married 22 years she accepts my duel life even though don’t venture out of the house too often looking forward to reading up on tips to make me more lady like

    • JaneS 2 years ago

      Jamey here at CDH you’ll find lots of tips and suggestions that can help you achieve the goals you set for yourself. There are also many people who will share experiences with you that can help you on your way There are even things that be of benefit to your wife should she be interested to learn more.

      Enjoy what you find.

  9. janis newton 2 years ago

    Hello JaneS, it is great when other people can recognise the person we are rather than the mask we wear. I have found so much from having one or two people who can see the real person that lives inside and even if I am in the male persona they call me by my feminine name. The small steps for Me came from being invited to take part in a ‘girlie’ night where my friends gave me plenty of help and advice about being the real me and the confidence to shine.

    • JaneS 2 years ago

      Thank you Janis. You’ve found the crux of the issue – confidence. We are frequently our own harshest critics but with the help of friends like yours we can develop the confidence we need to be who we are.

      Best wishes.

  10. Vanessa Law 2 years ago

    Another wonderful post Jane! I love the emphasis on small steps that will eventually get you there. Coming out is a process.

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