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.
18 Responses
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.
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
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!
Lisa
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.
Lisa
Amanda,
My reply to you ended up under Raquel’s comment below.
Cheers.
Lisa
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
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.
Lisa
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.
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.
Lisa
Lisa,
I read your thoughts on AGP with some interest , I first heard of Blanchard’s theory from a GG contributor on an online forum . I dug deeper and got a great deal of information from someone who continued his work and expanded it . At the time it gave me something to try and undestand myself . I did have a serious conflict at the ag of 8-9 , my T kicked in early and totally confused me , on the one hand I was filling up with male hormones and on the other a gut feeling told me something was wrong , why did I want to dress as a girl ?
I also eventually sought professional help , eventually I realised all these theories and ideas from professionals simply placed us in boxes with a suitable sounding label . It wasn’t until I went full time that I reaslied I don’t fit in one box and more importantly the only valid label I needed was my name Teresa .
Sorry to repeat myself but I now suggest we treat CROSSDRESSING as a verb instead of a noun , simply saying I’m a crossdresser explains nothing and leaves many unanswered question . If we say I crossdress because we can then accept the reason why , we can question why we do it . I do think it’s very important to know some but possibly not all the answers , it helps YOU to find YOU and it can go on to explain to others the true reasons . Understanding and hopefully acceptance may follow but eventually most of us don’t have a choice we need to lay all the cards on the table .
Why should we be made to feel guilty and ashamed of something inside we can’t change , some of our wires are crossed we just have to learn to live with that situation .
Did I have a tipping point ? Looking back I don’t feel there was a single one , they were more like stepping stones , each one taking me down an uncertain path , perhaps you could say looking for a light at the end of the tunnel , breaking out of one box and finding another with a different label .
I admit I didn’t think I would be living my life as Teresa fulltime , I have no regrets because I’ve finally found some peace in my life . Thankfully I haven’t lost as much as I feared , in fact my life is fuller now , when I see a box now I jump on it in my heeled boots and place it in the recycle bin , as I now live outside boxes !
Teresa,
I sometimes read here someone drawing a conclusion about others based on their own experience. We ought not try to generalize either from our own or from someone else’s experience. I increasingly value my ability to listen; to hear someone else’s story and find joy that they have found some important part of themselves. I feel that way hearing from you. I don’t want you to be anything but your own woman, a woman named Teresa.
Nothing I say creates a prescription for anyone else, but it is fun knowing that not all the roads Inuavr taken are poorly traveled.
Lisa
Lisa,
I know we share a common theme but I also appreciate we may need a slightly different solution to deal with it . Sharing our stories might help others , I know I wouldn’t be where I am now without listening and sharing . We may consult professionals but often they arrive at their answers by talking and listening to other transgender people and often their answers don’t correspond to others . What’s more important is helping people live their lives as happy and care free as possible , other people’s horror stories really upset me because I know how bad things can become .
Lisa,
I don’t know why I didn’t comment on this post back in 2022.
Your thought process and writing is excellent and I thoroughly enjoyed reading this post. Thank you so much for telling your story.
Some parts are very similar to my own and some parts are completely different. And, knowing you in 2025, your journey is so magnificent, while mine is at a complete stop.
I am so happy for you. The more we share with each other and our community, the more all of us gain knowledge and acceptance.
Love you a lot,
Jocelyn
Hello sweet lady,
You are always so kind. Thank you for your comments. I completely agree that sharing has value. We need a forum like Kandi has provided because it lets us share bits about ourselves. I have always enjoyed hearing your bits, and I am pleased to know you have enjoyed mine.
That being said, the original post, at 3 years of age, is showing me how much I have changed over the ensuing years — in wonderful ways that I do not regret, even though the road has not been easy.
Thank you friend for walking part of the way along that road with me.
Lisa, this is the first time I have read your post. When we first start dressing, we are not sure why we are doing this. We question if this behavior is normal, or you have a mental problem. We stumble on our presentation, and we may not be able to explain to our loved ones why we are doing this to them. The guilt of causing harm to someone we love may drive us to purge all our feminine things.
Over time we realize these feeling are real and we are not trying to hurt our loved ones. I hope over time my wife will be more tolerant of my gender identity. I now why I enjoy expressing myself in a feminine manner. I have come to realize that my gender identity is more complex then most men and women. I feel comfortable and confident in expressing both my gender identities. I need to be both genders, it is good for my mental health. I have grown and evolved as a woman, and I feel I cannot give this up. I could not give up my gender identity as a male and I feel the same way as a man.
Accepting who we are is a most precious gift, and being able to communicate our feeling to other girls in this community is such a wonderful thing.
I love each and everyone of you for your support and listening to me. This community is a treasure.
Love all
Julie
Julie,
Thank you for commenting. My post feels a bit dated, yet I think my observations in the post remain relevant for many readers.
You will see a post from me soon that pushes my boundaries further. I am still madly in love with my wife, and don’t want to do anything to hurt her, but I do wish she could inch a bit closer, so that I am not the only one bridging the divide.
There was a time when I believed I was equally comfortable as a guy. Sadly, that probably never was really true for me. I remember going to my gender psychiatrist in the UK expecting her to say I was right in the middle of the gender divide. That would have let me keep my transphobia intact. Imagine how it rocked my world when she concluded I was a trans woman, and she would recommend me to the NHS for hormone therapy! It took me a year, but I finally overcame my fears. I’ve been on an incredible journey since then. But I would never mislead anyone on this site to think that it is been an easy road, especially since I have always wanted to keep my marriage intact. It certainly would have been easier on my lovely bride if I could have stayed in the middle of the room, instead of choosing a side.
Keep up the good work. You seem to be in a good place in the middle. I am happy too, even if choosing a side has meant the road has had some ruts.
Lisa
Hi Lisa, you article has made me reflect with some questions. Can I identify my tipping point(s)? What are my tipping points?
As I look back on my life I realize there are several though until reading your thoughts I didn’t see them as tipping points.
My biggest & most recent was about 2 years ago when I finally yielded to what I always sensed, but mainly out of faith conviction was determined to fight it; I am trans. Once accepting that, it was relatively easy to put all the pieces together and understand what drives my desire to express as a woman. I am driven by the same thing that drives every cis woman. Their sense of identity as a woman drives them to express themselves as the kind of woman they see themselves as. I want to express as a woman because I am one, biology (yes I read another of your articles addressing this) notwithstanding.
In Amanda’s reply she makes a point about our wives having their own “tipping point”; that of recognizing just how fundamental our own womanhood is to us. That point being, their understanding that we, as their husbands having something going on much deeper & foundational than just a desire to dress in woman’s clothes.
My wife is OK with my dressing around the house, but there still is plenty of male me showing through, so that in her mind I am just a man who likes to wear woman’s clothes. I truly appreciate her acceptance at that level, however I long that she could understand how foundational womanhood is to me. She loves her husband, the man, and out of love for her I fill that role for her, my children (all grown), and grandchildren. However should she come to that point of understanding and accepting me as I accept myself that would probably be my tipping point to HRT.
Charrie,
Thank you for sharing your tipping points. Your final paragraph caught my attention, as I could have written it, up to the HRT conclusion. I finally sat down with my wife four years ago and told her about the conclusion from a professional, and that I had taken no action for a year. I said I felt like I was getting worse, not better, and that I wanted to try HRT as a therapy. She reluctantly agreed, because she knew my struggle was an honest one and that I was fighting for “us” not just “me.” She hasn’t been pleased with her acceptance of my decision on HRT, for one fact — my breast growth displeases her. Otherwise, she would be fine with the hormones. Perhaps that truth proves nothing except that good communication is a key. At least she knows I have been taking her into account. I’m sure your wife on some level feels the same. She (like my wife) simply doesn’t want to lose her husband, the father of her children, and the grandfather of her grandchildren. I would say that one of my most important jobs is to put her first as much as I possibly can.
A final thing is that I loved your comment that what drives you is the same thing that drives every cisgender female. In fact, although my wife would be loathe to admit it, I know she appreciates how much the post-HRT person she lives with shares her most fundamental needs and therefore understands her better than most cisgender men ever could understand their wives. Of course, that hasn’t led her to embrace my bi-gendered existence!
I continue to think about all the things we have discussed in private. The worst thing about being transgender is the feeling of being all alone.
Lisa