I have a question to ask…

If you are going to transition and wish to pass as a cis-gendered woman, where and how do you find your frame of reference? Women that are my age have been mothers and many grandmothers as well. They have had to contend with periods and menopause; they have lived all of their lives and grew into the role I yearn to play. They’ve received help and guidance from their mothers, grandmothers, female relatives, and girlfriends. How can one make up for all that time and experience they have on their side?

I’ve always believed that I should have been born a girl, many times over. I have had many dark days, and I have purged countless times. My wife knew; she found out by accident and didn’t really approve or offer encouragement. As a trans woman, I would become the person I believe I should be, thought I should have been all my life. My crossdressing has always been a temporary fix, those stolen moments which have always been spent alone. There has never been a girlfriend around to confide with, one who might tell me a particular shade of lipstick or eye colour doesn’t suit me. Girls/women have that inner confidence, and they can chat away with other girls with ease. Yes, I know that there are shy girls, but the majority have developed the confidence to chat away, regardless.

The truth is that I have never really had the typically male perspective on life; my ability to converse with peers has always been hard. I’ve always felt uncomfortable making small talk and the ultimate male experience “At the urinals” has always held a certain terror. Yet with women, chat has come easier, although more cautious and safer. Subjects such as clothes, makeup, and boys are to be avoided.

How on earth do I suddenly get 60+ years of experience and put it into practice as I transition? Where can one turn to find help? As a woman, who at this point, has never even been seen dressed by anyone, let alone venture out of the house, where should I turn? My life has reached a turning point and I want it to be one that heads in a positive direction. There will be good days and bad days. I know that by becoming Jenny, I will create issues within my family and grandchildren. I know I will need to take the leap of faith in becoming Jenny. By doing so, I will finally be the person I should have been all along.

I appreciate you reading my thoughts and look forward to reading your responses.

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    Clarissa Cross
    1 month ago

    I think you should make an appointment with a crossdresser service.You might have to travel at bit to get there but I read of some here at the forum who have tried these services and they all report that they got a lot of help about dressing and makeup

    Cassie Jayson
    Trusted Member
    1 month ago

    Hi Jennifer. It sounds to me you need 2 things. First a counselor to help find a direction. Second come out to someone, in my mind a GG, who would be happy to help you with clothes and makeup. I think this person would be someone to share all kinds of girly talk –don’t make it ALL about you.


    Trusted Member
    1 month ago

    Hi Jennifer, I can relate to your wife finding out about your CD by accident… that scenario happened to me too… Kathy was (is) not supportive to this day…she first met Leonara about 10 years ago…. In processing my CD revelation she realizes it is a part of me and prefers that I dress when she is not home which is 2-3x a week..we have a “don’t ask, don’t tell understanding ( doing housework en femme is very satisfying). Kathy encouraged me to seek counseling…it was the best experience for me to accept and balance my feminine alter egos. on… Read more »

    Jane Mansfield
    1 month ago

    Hi Jennifer, to reveal your inner Jenny is a leap of faith. A long time to think about outcomes, people being emotionally hurt loathing. Once you reveal Jenny to those you love they will understand or at least begin this journey. You are still the same person just changing clothing style, and presenting a feminine persona.
    Take one day at a time, make some notes on what you want to say. Make a time that suits your partner and you, and allow time for reactions.
    I wish you all the best Jane

    Active Member
    1 month ago

    I have a local Meetup group with cis women spouses, transmen, transwomen, CDs, gays, straights, every flavor. I haven’t gotten the nerve to ask, but I’m feeling more comfortable around them so I will ask some of them for opinions. Do you have a daughter or niece or younger cis woman you can confide in? Try Ulta or Sephora for makeup help. YouTube is a wonderful source if your search string is limited enough. Lastly, ask some people here or on TGH for help. I’m no fashionista but PM me and we can chat! For frame of reference, my therapists,… Read more »

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