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What’s The Point?

I realize how little I know and how much I learn when Lisa blesses us with her thoughts.

By Lisa P.

Tina Davis had a wonderful post on her tipping point as a crossdresser (Tina’s Tipping Point — December 13, 2021), explaining how her 2016 adventure out fully dressed to the Tiffany Club helped her to feel better about herself and has allowed her to progress to the point where she feels comfortable and enjoys her time out with others in public places. We all applaud her for sharing her journey so honestly. She reminded me that I have never shared my journey succinctly for this audience. The big difference between us is that I have no one point that I would describe as a tipping point. I have experienced a lot of different points on the gender compass that has guided me on this journey.

The First Point

I believe I first became aware of a bit of gender disconnect when I was 4-1/2 years old. That was a time when I loved being with my older sister, playing with her and wanting to be more like her. By the age of about 9, when she told me one day that she wished I was her sister, I found myself wishing the same thing. That was a bit of an “aha” moment, as I look back on it. Sometime around that same age I remember trying on some of her clothes secretly and loving the colors, textures and fit.

The Puberty Point

Puberty convinced me that my interest in female clothing was linked to sexual gratification and from that point on for many years I tried to control my urges (with a couple of purges) because I wanted to have a “normal” sex life. As a heterosexual, I thought it was a kink and I came up with my own theory of what “autogynephilia” (being sexually attracted to yourself as a girl) meant for me. But I can say honestly that I no longer project that misdiagnosed term on to my adolescent self. It is completely normal for a heterosexual to be sexually attracted to images of women wherever they may be found (including in the mirror). Moreover, it is completely normal for cisgender women to look at themselves in the mirror and enjoy seeing themselves and thinking of themselves as sexy. If you take someone assigned male at birth who realizes that they enjoy (or even prefer) being feminine, it should be no surprise what happens during puberty, when a human’s sexual drive is at it its peak. As a result, I am in retrospect a lot less hard on my adolescent and younger self.

The Marriage Point

In any case, for many years I operated in complete stealth mode, hiding my inclinations from everyone (even myself) and thinking that I was just that rare guy who enjoys wearing women’s clothes on occasion. I came out to my fiancée (now wife) before we got married, but I played it down based on how little I thought I needed it (and I needed her in my life more than I needed it, I was darn sure) – she was so unaffected by the news that she promptly forgot most of what I had told her. During our first year of marriage, she decided to put makeup on me for fun one evening. Thinking that it gave me license to show her how I looked in one of her dresses, I ran to the closet and put it on. When she saw me, she became extremely distressed – so much so that she explicitly said (and she has consistently maintained that) she never wants to see me again that way, ever. I immediately slunk back into the closet, hiding from her and the rest of the world every attempt at femininity. We were poor as church mice, so I couldn’t buy anything (some of you know the feeling – if you have $10 for food, you aren’t going to use even some of it on something other than food), but I did “borrow” clothes from my wife to help me feel feminine when she wasn’t around.

The “My Own Clothes” Point

It wasn’t until I had a steady income that I slowly accumulated my first set of clothes – a pink bra and panty from Victoria’s Secret, a blue jean miniskirt, some white high heels and a cute white top to match with the outfit. That was it. Not much of a tipping point. No makeup, no jewelry. None of that made sense with my facial hair. I was limited to dressing at home, and because of 75-hour work weeks and little ones that needed constant parenting, my dressing for about three years was limited to getting up in the middle of the night when everyone else was sleeping, creeping into the attic (not easy, as that required pulling down the creaky ladder first), pulling down the box with my secret stash and then taking it downstairs to wear in the backyard or living room.

The Post-Purge Point

When my daughter was born, I decided that the entire stash had to go. I thought that to be a good father to my daughter I needed to give up that part of myself. I told myself that self-control was all that I needed. It worked, sort of. After purging (sadly, I threw everything away in a moment of decision rather than donating the clothes to a charity), I managed to stop crossdressing for five years. I can’t remember exactly what it was that made me do it, but when she turned 5, I suddenly had a very strong desire to buy and wear women’s clothes again, and the urge was much stronger than it was before. That point was nearly 30 years ago. I promptly visited a neighboring mall and found a store for teenagers. I told the clerk that I needed to buy an outfit for a niece and told him exactly which outfit I thought she would like. When I got home the skirt fit well, but the top was too small, and I somehow got up the courage to exchange the top, with the excuse that I realized that I had bought the wrong size for my niece. From there, I began to buy more and more clothes, but I was still only a distance along the way toward my personal version of femininity.

The Shaving Point

After several years of wearing clothes in hotel rooms or at home when no one was around, I knew the facial hair needed to go. Once I had shaved it off, I began to experiment with makeup. As an amateur stage performer, I was ahead of most cross-dressers, but I still had a lot to learn. Thereafter, I ventured out of my hotel room while on business trips – down the hallway, then down the stairs, right by the front desk and outdoors into the night – freedom! Eventually, I realized that to wear what I wanted, I would need to shave my legs and arms as well. I was on a business trip down under when I managed to do that, and on that same trip I went to the hotel pool and lounged on the pool deck (and even took a dip in the pool). I also walked along the harbor and went to a major shopping center. I was amazed at how much I was able to do on that trip, although I felt terribly guilty for not being 100% focused on work. Over the years, as I traveled more throughout the US, Asia and Europe, I kept right on crossdressing at each destination. Going out among the people was intoxicating, although not always safe, I am sure, especially since I often boldly visited the women’s rooms in places that have laws against it. The fact that I took risks should tell you something about how strong the need to be accepted as a woman was for me. Plus, I found so much joy in it. Sometimes I would visit the women’s room just to see how nicely appointed they were (historical footnote: the Waldorf Astoria in New York City pre-renovation had the most incredibly beautiful baroque-inspired and gilt-fixtured women’s room off the lobby, with individual toilets along a corridor that stretched up a couple dozen steps – a very unique set up).

The Free-to-be-Me Point

Finally, with children fully grown I had the opportunity during long weekend trips away from home by my wife (to visit girlfriends or family) to live full-time for two, three and even four days. I planned makeup lessons, had my nails done, visited the beach, went on bike rides, went clothes buying and did a lot of personal photoshoots. I also joined groups of women and started to socialize more as a female.

Accepting Myself as Trans Point

Eventually, I realized that being female was more “me” than being male, even if I was still a male at work, with my family, at church and with my friends and neighbors. That realization led me to seek a professional assessment. I went to a gender therapist 15 months ago. She confirmed that I have gender dysphoria (big surprise). She described me as a transwoman (a bit of a surprise, as I was rather expecting that I was exactly in the middle between male and female — even if that is as rare as a unicorn — so that I could eventually enjoy both sides of myself equally). That diagnosis from a dispassionate third person has led me to accept myself more and, interestingly enough, it has also led me to want to express myself as a female more. I still do not see myself transitioning to being a female full-time, as the price to pay for that would be too high. But who knows if that balance will tip in the future?

In the final analysis, I don’t know which one of my points was the most important tipping point, because there have been many new points in my journey and another one no doubt is just around the corner. So, what is my point? My point is that we each walk a pathway that has byways and highways, low ways and no ways. As long as I don’t give up on myself, I don’t need to make one point more important that another point, at least for now.


9 Responses

  1. Lisa, there is so much overlap between your story & mine and, I suspect, many other girls who read it. Your description of the time you were dressed and made up in front of your wife was particularly poignant as my wife encouraged me to do similar with pretty well identical results. It’s something I’m going to dig into in my next few posts here but I think it lays bare the moment when wives start to understand what is really going on inside us. I would go as far as to say that they had a far better understanding than we did at that point in time – it’s the moment that any assertions made that it was only a bit of dressing up fun go out of the window and the realisation sets in that there’s a lot more going on than was realised. Wives understand that quickly but it can take us years to catch up.

    What is the situation with your wife now? I get the impression there’s an uneasy truce but is it discussed at all between you?

    Thank you for a wonderful post.

    1. My ex saw me a few times as Rachael and unfortunately for her it just wasn’t what she signed up for
      We went to Vegas and agreed to let me be her and during that time she shared that she saw how happy I was
      She was right but I would give anything to have her back.
      I say that now of course but as time has moved on I know this is part of me and I just have to deal with the bumps

      1. Rachael,

        I almost missed this comment. It made me pause, because of the personal pain reflected in it. If there was one part of my essay that was less than honest, it was my failure to admit the “pain points” along the way. I am sure there will be more, and the thought is disquieting, to say the least.

        I am sending good thoughts your way!


    2. Amanda,

      Thank you for your comments. My hope was that something from each “point” would resonate with every woman out there (maybe even some of the “cis” persuasion). As I think I have mentioned in some other posts, my wife is mostly DADT, but about once a week I make her talk about it even for a little bit. Fortunalely, she realizes her internal conflicts — she is an ally of the LGBTQ+ community generally from a social justice point of view particularly. She has made minute progress over the years, and although I give her a nudge frequently, I have no desire to push her over the edge.


  2. Lisa, thanks for sharing your story and not totally unfamiliar to many of us.
    Like you I went through many ups an downs of my gender expression until I finally understood it was just who I was, a bi gendered trans person and I’m good with that
    God bless Rachael

    1. Rachael,

      Bless you as well! Lord knows this path is not easy, but as Kandi tries to teach us, that doesn’t mean it can’t be filled with fun along the way.

      Thank you for your reply.


  3. Lisa, thank you for referencing my “tipping point” post and using it to show that we are all different in our approach to this life that we lead. In some ways, I am still very much in the closet and do not have many opportunities to get out. I do identify with the term “bi-gender” and will either be totally male or totally female in my presentation. Self-acceptance was a big step, but it is just as important to be accepted as who you are. That’s the next point I am reaching for.

  4. Tina,

    Well said. I definitely admit that I have my own biases, including fundamentally liking the gender binary. That is awfully unfair to those who aren’t on the poles, like we are. But, as you point out, we all have another point we need to be reaching for, if we want to continue to grow.

    Thank you for your original post, and your reply.


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