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Transforming from a hairy caterpillar into a butterfly

11:55 am Wednesday, 6th January, 2021

I was happily married for decades to my soulmate. She was an amazing person and her love remains with me to this day. I have moved forward with my life knowing that she would approve of where I am now.


When I was raised you were either a man or a sissy. You were forced to never show your feelings and always internalize your pain. You could never appear weak or demonstrate affection. As a small child I did not understand why I could not have long hair like my sister and her friends. I left home as soon as I was able to earn enough to pay rent and never looked back.


Then I met my soulmate and we became a team. She was both my lover and my best friend. I told her about my crossdressing habit and she understood and allowed me to have my clothes and dress up because there was no sexuality involved. Since I had always been “in the closet” anyway this was an acceptable arrangement given that society frowned upon crossdressing in public and still does.


When our daughter was born my maternal side emerged and I became the parent I never had during my own childhood. I would take personal time off work to attend her sports events and go with her on field trips to museums.


My wife was diagnosed with cancer and the next five years were stressful to say the least. After she died the grief was of a magnitude that has to be personally experienced to know what it is like. The hollow emptiness inside is something I would not wish on anyone else. I did not know that it was possible to feel actual physical pain from grief. Screw hiding my emotions, I cried openly and I didn’t care who saw my pain.


Then my maternal instinct emerged again and came to my rescue. My feminine side took over and instead of internalizing my pain I started sharing it openly the same way women do. I began dressing full time and sleeping in a nightie and panties. I let my hair grow long and used depilatories to rid myself of body hair. I took my clothes out of storage and hung them up so I could choose my outfits.


My daughter, now an adult, is very supportive and made me a beautiful necklace. That was the first time that anyone had ever given me jewelry. Her present made me appreciate that she has fully accepted me and we share an interest in clothes and make up.


So now I am a widower who is learning what it is like to live dressed as a woman. The time spent grooming and taking care of my skin and hair seems almost normal and the routine is comforting. Looking for shoes and dresses and deciding what to wear are still novel experiences for me. The bras and panties that I originally purchased because they were pretty turned out to be uncomfortable to wear for extended periods. Now I prefer soft cup bras and cotton panties instead. Wearing a bra and breast forms gives me confidence in my female persona.


One day while standing in line there was a couple ahead of me who were holding hands. Both were wearing jeans, t-shirts and sneakers and one had long hair and the other had very short hair. They were both female but there was no disapproval that one of them was essentially crossdressing as a male. When a man wears feminine clothes in public he is judged by society whereas the same judgement does not apply to women. Why is crossdressing only a fetish when men do it? While there can be no doubt that the feeling of something soft and silky can be arousing is that not the case for both sexes? What is the difference between a women feeling the sensation of freshly shaved legs and a man feeling the same sensation after doing the same thing? My own need to wear dresses predates puberty so I do not perceive these feelings as being sexual in nature. Instead I consider them to be ordinary pleasures that both sexes can enjoy but society considers it taboo for males to partake in them.


For some cross dressers there is a direct sexual arousal connotation which fits the definition of a fetish but it is wrong to apply the term universally to all cross dressers in my opinion. For many of us our female clothes are an expression of our inner femininity. To be wearing a skirt and blouse means that I recognize myself as having a female aspect to my personality. I am not doing it to attract the sexual attention of anyone else either male or female, instead I am doing it for myself as a means to express who I am. In this respect it is not a fetish but would be more appropriately called a cross dressing lifestyle instead.


I cannot be what I am not since I am neither 100% male nor 100% female, instead I am both male and female that combine to form the whole person that I am now. I can appreciate the strengths that these different aspects of my personality provide. Since opening up I have encountered several women who acknowledge the masculine aspects of themselves and we have formed close bonds of friendship based upon our shared understanding of the duality of our personalities.


Allowing myself to become warm, caring and compassionate makes me realize that out of those depths of loss and sorrow it is my female side that has enabled me to become this better person that I am today. If we can find a way to enable public cross dressing as an acceptable lifestyle choice in society then there could be fewer hairy caterpillars and more butterflies around. Would that be a bad thing?



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Curious about crossdressing and finding clothes and shoes that fit me.


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