i am a year and nine months into my transition to feminine presentation… i have completely replaced my masculine leaning clothing with decidedly feminine garments… i have invested a small fortune in cosmetics, mostly nail polish and lipstick… my morning ritual includes belly, chest, breast and face shaving… face and neck moisturizer/sunscreen… deciding on my foundational garment, then accessorizing… jewelry, headbands, scarves… and finally, lipstick… i haven’t developed a nightly face cleansing routine but i have the products for it…

during the past 21 months i became progressively bolder with my look… i moved from garments walking the line between masculine and feminine to garments, like flowy maxi dresses, that are unmistakably women’s clothing… i moved from barely noticeable flesh tone lipstick to shades of pink, copper and then bold red… it has been an extended normalizing process… for my wife, my family, my community, myself… i needed to get used to being womanly… wearing lipstick, jewelry and dresses in public… i needed to figure out how safe i was presenting as a womanly man in public…

i am lucky… wife, family, friends, community… all have been able to embrace this new me… my wife misses more masculine me… but she knows i am not a substantially different person in my thinking and beliefs and that feminizing myself makes me happy… my mother and sister don’t fully understand it, but both of them have been able to make peace with it because they see how happy i am… both have given me jewelry and/or scarves from their personal collections… my brother fully embraced and supported it from the beginning…

my father passed away a few years ago, which is fortunate because i am certain he would not have embraced my feminine… i would not have… did not… challenge him with it… to do so would have cut me off from my mother… in part, because of him, i kept my masculine facade longer than i might have… his death weakened the dam to my feminine, which then burst…

thinking about my life… i realize that feminine expression lurked in the shadows from an early age… i can recall my preteen self trying on my mother’s bras, which my sister saw and ratted me out… i don’t remember any serious consequences… my parents probably thought i was exploring as kids do… i wonder if my father even knew about it…

in high school there was reason to don a toga garment in latin class… i loved the dress like flow of fabric around me and decided to stay dressed in the toga as i went to other classes until my latin teacher caught up with me and suggested it wasn’t playing well to my classmates…

i recall my high school girl friend giving me shirts she got from a relative’s business that were essentially blouses… there was a floral and completely transparent one that i was prepared to wear to school… my mother talked me out of it… i was not a kid that ever fit in very well… she had worked hard over the years to help me avoid being picked on…

during my first marriage i collected women’s hat pins, beaded purses, and other feminine accessory collectables… my second wife carried one of my beaded purses on our wedding day…

before i fully blossomed into trans-feminism, i purchased a couple of unisex maxi tunics from Rawganique, which i wore on ceremonial occasions… weddings, baptisms, etc… for a niece’s wedding i wore a long sleeve off white tunic and white, Truman Capote style summer hat… i was declared the best dressed man at the wedding by more than one of the young women attending… when i started using the same hair stylist my wife used i discovered the joys of a french braid, which became my signature hair style to wear with the maxi tunic garments…

as i said, all of this stayed on the borderline between masculine and feminine until my father died… the year after his death, a compulsive fascination with female mannequins and women’s clothing began to build… i wrote about it… i also read numerous books by women about being women… i photographed women’s shop mannequins on my daily walks… i was not conscious of where it was leading until i found myself ordering my first lipstick… flesh colored… barely noticeable when i wore it in public… shortly after that i ordered my first sweater dress which i wore over jeans in tunic fashion… my desire for feminine presentation mushroomed… finding clothes and accessories became an obsession consuming all my available creative energy for more than a year…

recently a woman friend shared a link to a facebook post written by a dad about his pre-teen son who liked wearing dresses… he was supportive and proud of his son’s courage… for the time being, he wrote, they are still using he/him pronouns to refer to him because, as his son put it, “i am just a boy that likes to wear dresses”… that is where i seem to have landed… i am a man that likes to wear dresses, jewelry and lipstick… i love to feel feminine… womanly… it’s hard to describe how good and complete i feel in feminine presentation… still, as i assured my mother, much to her relief, i don’t feel a need to become a woman physically the way i did to become a womanly man (wo-man?)… i literally could not control it… while i am sometimes sad i don’t have a woman’s body (ooh the tight fitting sexy dress possibilities!) i make the best of what i have… i am happy with that… true transitioning to a woman’s body is not compulsively essential to me… or worth the expense and risks of hormone therapy, surgery, etc…

returning to my community, i have been amazed by how embracing people have been… women especially… i have been gifted jewelry, clothing and scarves by many of them… some men… strangers, acquaintances and friends… have embraced me with friendliness… just the other day, two male acquaintances made a point of sitting down and talking with me, even as i was wearing a black linen mini dress, brass bead necklace and bold purple red lipstick… i am grateful… there are towns north, south, east and west of me that would not be so accepting… i moderate my feminine when i travel outside of Beacon…

The difference between the sexes is not whether one does or doesn't have a penis, it is whether one is an integral part of a phallic masculine economy.

–bell hooks, Feminist Theory: Margins to Center

i believe in the power of feminine… having learned that women are every bit as capable of exercising the power of patriarchal structure, in dominating patriarchal ways, i realized it was the egalitarian and nurturing qualities we associate with the feminine that were important and sadly withered across much of human history… i am trying to puzzle out why masculine has been so dominant since time out of mind almost… there are, i believe, some examples of matriarchal societies that deployed the power of feminine to organize and manage themselves, but they have not been common… in the world today there is a testosterone contest of powerful men going on… i want masculine to rebalance with feminine, yinyang fashion… both qualities are important but masculine is far too dominant and running amok in the present moment… if the rebalancing is half as positive for society in general as it has been for me, the world will be a much better place…

when Donald Trump was elected president, i worried i would have to return to the closet… i am still not sure i won’t… we appear to be in the early stages of constructing a police state… they have built an ICE detention facility in the middle of the Florida everglades… there appear to be plans for more facilities across the country… the big ugly bill just passed by congress contains billions of dollars of extra funding for ICE and immigrant “management”… if we are moving to worse case scenario authoritarianism, this police state apparatus will be turned to other uses when the administration is done with immigrants… LGBTQ+ people in general, and trans people specifically, have been targeted in far right rhetoric… it will be constant reassessment as things continue to unfold… for now, it is both my happy place and my anti capitalist, antiauthoritarian statement of defiance to wear dresses, skirts, jewelry and lipstick for all the world to see… resistance is essential, and not yet futile…

It is almost ten months now since I began to manifest my feminine being to the outside world. I grew my hair longer, started wearing lipstick, began scouring women’s clothing sites and buying a new wardrobe. Then I began presenting femininely in public. I was very anxious about the pushback I expected to get and rather surprised when it didn’t happen. To be sure, there have been disapproving looks from strangers, men mostly. Most significantly, there has been pushback from the women who have known me the longest. My wife, my mother and sister. They’ve had to adjust their idea of me which has been a process for them.

The most pleasant surprise of all, however, has been the number of relative strangers who have gone out of their way to affirm my feminine forward presentation. A neighbor from a few doors up was driving by and stopped to tell me he thought I had been rocking my outfits lately. Another neighbor I often pass during early morning walks made a point of telling me how cute my outfits were. A vender in the farmer’s market told me she had been noticing me for a while and that she loved my style.

I am not naive. I know I can expect some ugly moments in the future. But for now, I am basking in the warmth of loving acceptance.

I had a brief text conversation with a family member yesterday. My trans-feminine explorations are not sitting well with them. They haven’t exactly disapproved, but it is clear it makes them uncomfortable. I think anything outside the box gender/sexual makes them uncomfortable. They indicated that, as a woman, they aren’t interested in makeup or getting their nails done. They can’t relate to my interest in them as symbols of the feminine. Furthermore, they feel that feminine comes from within. It surprised me that they seemed to lack the very feminine quality of empathy, the ability to see things from another’s perspective. I told them I had strong feminine currents inside me and that the outward expression of feminine through nail polish, lipstick, jewelry, etc. was a way to connect what I feel inside with the outside world and reflect it back to myself.

…

Last week, I attended a literary event featuring Lucy Sante. I bought and have been reading Lucy’s autobiographical account of her transition, which she undertook at age 65. I was 68 when it started to surface that I wanted to present femininely. I am a few months into my 69th year now. She seems to have been more fraught about it than I have been. She also seems to have experienced full-blown gender dysphoria. She is doing hormone therapy. I don’t know anything about the changes that one can expect from hormone therapy, but Lucy looked to me largely like I look to myself. A man presenting femininely.

Hormone therapy, so far, doesn’t appeal to me. My body will have enough challenges coping with getting old. I don’t think adding hormone engineering to the mix would be doing my body any favors, and my psychological health around my feminine emergence is just fine. I am content with feminizing my body with clothing, accessories, makeup, etc. As much as I would like to have woman breasts, and I would, I don’t feel the need to fake them or get surgery. Getting my nails done. Wearing women’s clothing. Wearing lipstick and jewelry. Whatever promotes a feminine impression to the outside world and, most importantly, to myself, is where I am at. Basically, I am a cross dresser. It’s ok if the world sees me as a womanly man and not a woman. Of course, I don’t mind it if anyone wants to acknowledge my womanly presentation with a “mam.”

…

An important realization for my wife in all of this was that, fundamentally, I am still the same person I have always been. Yes, I am presenting femininely. Yes, this exploration has made me a little more feminine on the inside, too. But I have always had feminine inside me and have never presented as anything close to macho masculine.

Lucy Sante talks about coming out to her partner who felt betrayed, lied to. Lucy had been so repressed for so long, that she actually was living a lie and the breakage of trust was a real thing. My wife had a similar reaction initially. I explained to her that I hadn’t been hiding anything from her. That I had shared it with her as soon as I started feeling it. Which was true. In a series of blog posts that turned out to be precursors to the “cracking of my egg,” as the trans community seems to call it, I wrote about what was emerging, though I didn’t realize it when I wrote the posts. I shared all of them with my wife before publishing. I was preparing both of us.

I have, to this day, a collection of beaded purses and hat pins that I developed during my first marriage. My wife carried one of the purses when we got married. She acknowledges there were indications of my feminine nature back then and that was probably part of what she fell in love with. I didn’t present femininely back then. I didn’t present femininely at all until it began to surface last year. So I can truly say to my wife, I didn’t lie or hide anything from you and I started letting you know as soon as I began to know, before I was conscious anything was going on.

Lucy seems to have burst out in a big gush. I am blossoming in a steady flow. Taking careful steps. Testing each new escalation carefully. I am now fully rolled out to family, most friends, and the public. I am pleased about it.

Just now, I read a section in which Lucy talked about dealing with her fascial hair. Laser removal wasn’t available as her beard was gray, and the machine can’t find the gray hairs. She had to do electrolysis, which took a year of weekly sessions in which each individual hair was pulled and the follicle cauterized. That is a kind of dedication and expense that I am not up for.

On my way home from the coffee shop where I was refining and adding to this post, I ran into a friend I haven’t seen in a while. I was in full feminine mode, which they hadn’t seen before. Even a few weeks ago, this encounter would have made me tense. I am much more confident and relaxed now. I opened up the space for him to ask about it by saying it was ok to ask about my feminine presentation. We chatted about various things, and he did circle back to ask me about it. He gave me a hug as we parted.

I have come a long way.

I have been thinking a lot about what it is I am becoming. It seems more and more that it is less about becoming a she, than a feminine he. When I think of myself in the third person, I think of myself as he. He is wearing lipstick. He is buying necklaces and wearing them. He is buying dresses and wearing them. He is wearing colors more often associated with she. My longings sometimes run to being a woman. Like when I see a beautiful dress that would require having breasts, hips, and a waist to wear, but mostly I am he in my mind. At least for now. I continue to evolve.

The women’s clothing I wear is feminine, even when I wear it. But it is almost unisex because whether I wear it or a woman wears it, it has substantially the same drape. I have a cotton shirt dress which is really an oversized, overlong, crewneck cotton shirt. It fits loosely on my body, as it would on a woman’s. It is really comfortable. Of course, on a woman it hangs differently, off the breasts for example. But when I wear it, I don’t need breasts to get a good hang.

The gender implications of clothing, jewelry and makeup are interesting. The culturally defined messaging of various forms of dress and adornment are just that, culturally defined. As are the expectations of what gender message one is to send with their clothing and adornment. In the United States, we are steeped in a myth of masculinity and femininity represented by the Marlboro Man and Marilyn Monroe archetypes. It’s an extreme and, let’s face it, toxic masculinity and femininity. In reality, we play out in a much more diverse way. But the basic myth of what man and woman should be remains Marlboro Man and Marilyn Monroe.

As I have said before, I am not the Marlboro Man. I have never been and have no desire to be. I prefer feminine to masculine, in my expression of self, in the things I am happy doing and in the people I surround myself with. I don’t seek to be a woman, so much as I seek to be a womanly man. Of course, in toxically masculine/feminine society, this is a display of extreme weakness by a man. It is the incomprehensible-to-some preference of emulating the femininity of Marilyn Monroe instead of possessing and fucking it. I love smashing the patriarchy!

Last night was my friend’s birthday party. I went with my wife in full feminine mode. As I wrote last week, I was both excited and anxious about this party. Even though I have been presenting my feminine self for eight months now, it was the first time we have socialized with our friends with me in full feminine mode. I wasn’t sure how this would be for my wife or how it would be received by heterosexual friends. I think my wife might have been a little anxious too. We quickly relaxed once there. I came home feeling it had been a successful evening, and my wife said she thought so too.

The photo above was my look for the evening, though I did change my lipstick to something more subtle and peachy. My garment is a black cotton shirtdress. I also wore dark gray leggings, black leather sandals from Banana Republic, a buffalo horn bracelet on my left wrist and a guitar string bracelet on my right wrist.

I chose this party for coming out to a larger circle of friends and acquaintances because my friend is lesbian. I figured the crowd would be a mixture of straight, gay, and lesbian people. That is, it would be a friendly audience. I also expected there would be a few people that we have socialized with over the years, before I began presenting femininely or even knew I wanted to. I was right. A woman my wife regularly goes to the gym with was there. She was the first person I talked to at any length. She took feminine me in stride. If she missed a beat, I didn’t see it. I was glad she was there. Last fall, when my feminine presenting self began emerging, my wife told me she had no one she could talk to about it. Hopefully, my wife now has at least one friend in on my changes and can talk to her about it.

A heterosexual couple we have known for some time came too. I spent a good amount of time talking to the husband, and my wife did the same with his wife. They didn’t miss a beat either.

A woman artist friend rounded out the people we saw who knew me in the pre trans feminine days and hadn’t seen me present femininely before. Several years ago, she and her husband divorced. At a party about a year ago, she showed up with a new girlfriend and last night she told us they were getting married.

At the end of the night, my artist friend’s fiancé and I had a conversation about an article I had read that morning making the case for lesbian separatism. It suggested it was good for lesbians to form lesbian only communities, separate from the dominant, hetero-patriarchal society, to be in a safe place free of its oppression and thus be unfettered in establishing their lesbian identity. We mutually agreed that we preferred the stance of being who we are within the context of the dominant culture as a means of holding space for that self. I certainly have no desire to spend my time only with other trans-feminine people. I have carefully and deliberately been weaving my feminine self into my community with the hope that I will be embraced, appreciated and loved for who I am. I also want to exist as a demonstration that there are other ways of configuring one’s self. I intend to help smash the patriarchy.

As we were leaving, my artist friend’s fiancé asked me what I planned to do for pride month. I told her I hadn’t thought about it, but that now I would. It was only a little while ago that I came home and realized that the pride flag we have been flying for years supporting the LGBTQ+ community was now flying for me as well. I’m not sure if I can join a parade yet. I am still a work in progress and still rolling it out to my friends and acquaintances. But I will find a way to quietly celebrate my entry into this community and to honor those who came before me and created the space for this new me to be.

PS: I have decided two things to do in celebration of Pride Month. I want to bake some sort of pride cake and have some friends over to help me eat it. And, I would like to come completely out to my family, which is my Mother, my brother and my sister at this point. I don’t think it will come as a total shock to them. On my last couple of visits, I have worn “sweater tunics,” aka sweater dresses, and other casual tops purchased from women’s clothing sources, as well as wearing my hair in more feminine ways. There has also been an essay or two shared with them which certainly pointed at it.