Scenes From My Feminine Transition

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.

an update on my feminine blossoming + my fear of men’s capacity for violence

… i continue to grow my feminine out into the world… my rollout has been measured… i think carefully about each step and work out half steps if any step seems too scary… each step is marked by a question, “do i have the courage to do this?”

… last weekend i came out to my family… i had been thinking about it for a while… waiting for the right moment… i sent them a link to a post i wrote in January of this year, saying i had been going through some changes and i’d been wanting to share it with them for a while… they all read it… they were pretty cool with it… i talked with my mom about it the other day… it turned out she was imagining me as a drag queen… i had a good chuckle about that… “no mom, it’s not like that… in fact, i wore a sweater dress the last time i visited… just add lipstick and some jewelry to that memory”…

… becoming a person who expresses themselves differently from most of the people around me is fraught with fear of rejection… i am aware that there are places i probably shouldn’t go in full feminine bloom… i choose carefully when and where to present my femininity… i am finding acceptance for the most part… people i know are curious, i can tell by the way they look at me when they see me in feminine mode for the first time… they are reluctant to ask me about it… they don’t realize i want to be asked, so i have decided to state the obvious so we can talk about it…

… the other day, my wife and i went shopping for cosmetics at Sephora… i wanted to start experimenting with eye shadow and she wanted to find a new blush and lipstick… i suggested the joint adventure… she was all in… i know it can be weird for her sometimes… but she has been way more supportive than i have any right to expect…

… as with each of my steps forward into feminine presentation, i will start subtilely with the eyeshadow… i wore it for the first time the day after i bought it… i barely noticed it when i looked in a mirror… i doubt anyone else did either… i will slowly work up to bolder shadow statements… i am hot to try shiny metallic shadows… Shye, the saleswoman who indulged and educated me at Sephora, showed me a wonderful color pallet from Danessa Myricks… it’s on my want list… but first, the basics…

Love Is Love eye shadow color pallet from Denessa Myricks Beauty

… the day i started writing this i wore a black linen mini dress from Everlane… it stops a few inches above my knees… for the first time i wore no leggings underneath… leggings, even though worn mostly by women, give the left brains of people who see me an out… “oh, he’s wearing a long shirt and pants”… a mini dress and bare legs is impossible to construe as a pant and shirt combination… in the brutally hot weather we’ve been experiencing, my minidress outfit was soooo comfortable… and can i say, i have very good legs?…

… each escalation of my feminine presentation is planned carefully… i have to imagine it in detail for days… until it becomes so much a part of who i am that i have to do it…

… i was nervous walking down Main Street in my minidress with bare legs… especially when i passed men… i am anxious when i pass men in a way i never was before… most mornings i pass the entry to a martial arts studio… often, there are a number of pickup trucks parked on the street outside… samurai war lords loiter on the sidewalk after class yakking… i haven’t walked past them in full feminine bloom… i think i will avoid that…

… it is strange to be so anxious about what men might do… i fear their potential to be violent… women, i think many of you know this anxiety well…

… i have had a couple of close calls with cars at a particular intersection… both involved male drivers… one was definitely being aggressive… the other… hard to know… It’s not impossible that it was distracted driving…

… the other night my wife and i met a friend at an event featuring Lucy Sante… Lucy transitioned to feminine presentation late in life, as i have… in fact, we are about the same age and her transition happened only a few years ago… during the event, she described true gender dysphoria which she had been experiencing since childhood… i have been aware of the strong feminine currents of my being for a long time… i have always been comfortable with them, though i don’t think they ever rose to the level of true gender dysphoria…

… at the end of the program i walked up to Lucy and told her i was in the process of finding my feminine and that it helped me to see another trans woman who has undertaken a similar journey… i thanked her for being public and frank about that experience… she thanked me and wished me luck with my journey… i bought her book and look forward to reading it…

Coming Out to a Larger Circle

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.

Trans feminine person with wood bead necklace, black cotton top, bold green crystal frame glasses, black and white batik headband, hair cascading in curls to her shoulders and red/pink lipstick.

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.