Becoming Lisa


photo/Lisa Pomeroy
photo/Lisa Pomeroy

Becoming Lisa

By Lisa Pomeroy

Back around Thanksgiving of last year, divorced and forty-something and living alone, I was listing in my journal all the ways I felt I had failed as a man, and to my own surprise I wrote, “I just want to be a girl.”  

That was the beginning of my existence as a transgender person.  

Or, I should say, as a conscious transgender person. Looking back, there have been hints all along, and now that I think about it, I do have shards of a memory of a first, timid expression of femininity to my mother, probably around age five or so, and of being completely shut down by her response. I doubt it was a dramatic scene — I was, and still am, shy, easily quashed.

Emotionally, the weeks since the revelation have been a jolting pinball-machine of a ride. I have careened between exhilaration and confusion, joy and fear. The first day, I stuffed my male clothes with improvised padding to give myself lumpy breasts and hips. Looking in the mirror, I felt a part of myself I had been pressing down all my life well unstoppably upward.

Then I began to shop. The first few trips were terrifying. Panties, stockings, a bra, shoes and lipstick at Walmart; a gray acrylic sweater-dress at Reny’s. I picked checkout lines with young, female clerks and avoided eye-contact. The shoes turned out to be a size too big, because when I’d surreptitiously tried one on I was wearing thick man-socks. I also had to take the dress back, having guessed a size too small. On the drive back to Reny’s, I rehearsed lies, but once face-to-face with the bored, twenty-something returns clerk, I blurted out some version of the truth. She gave me a sharp look and made a contemptuous noise, but completed the transaction.

I came out first to a lesbian friend who lives in San Francisco. She was super-supportive, but also said that in her experience, cross-dressing men are not welcomed in mainstream gay culture, because underneath the dresses they are still heterosexual men. (I’ve since learned that’s not always true, but I gather that a majority of cross-dressing men self-identify as hetero males.)  

I then came out to a gay, male college friend who now lives overseas, and he was supportive, too, but he also said that in his circles, cross-dressers are like the little sister nobody wants to talk to on the playground. I hear a similar ambivalence, if not animosity, exists in Portland’s gay community. Every source I read confirms that “G” and “L” are completely different from “T.” G and L are about whom you desire; T is about identity.

This is not to say I haven’t been pondering the idea of romantic or erotic attraction to men, and there might be something to that. But, at least so far, I feel more pre-sexual than anything else. After all, I didn’t write, “I want to be a woman.” After a lifetime of hyper-responsible and inhibited maleness, I want to indulge the emotional, effusive and impulsive parts of me. I want to sparkle, be admired, feel pretty. I want to feel young again and do it right this time.  

It’s not just about putting a gender-bending twist on a midlife crisis, though. I also want to feel graceful and elegant, and get a wig with gray in it. (Can you tell I’m still figuring this out?) Anyway, sex seems incidental. It’s really all about how I feel as a self.

I got bolder shopping. In shoe stores and at makeup counters I began telling the sales associates I was shopping for myself. A few seemed uncomfortable, but stayed professional and helped me. Many took it completely in stride, and a few responded warmly.  (The Payless in Biddeford is particularly welcoming.) My most awkward retail experience to date was being told, while shopping “in drab” at the Maine Mall JCPenney, that I would have to walk across the store to use a men’s dressing room to try on a waist-cincher. I left without buying anything.

The Internet offers abundant resources for cross-dressers, including (of course) a huge number of products and services for sale. The site is a particularly active and supportive chat forum.  

The most active, content-rich and up-to-date of the few Maine-based sites I have found so far is Maine Transgender Network board president Alex Roan said the organization was formed a few years ago “in response to a lack of centralized information and resources for transgender people living in Maine.”

“There are a number of small organizations providing support and/or education around gender issues” in southern Maine, Roan said, “as well as pockets of trans individuals meeting informally throughout the state.”  

A Yahoo discussion group called “trans_port_me” used to promote social gatherings in Portland, but those ended several years ago and interest in the group dwindled, said Giselle Gail Moreau, who founded the group. The transgender community in Maine is fragmented, Moreau said, “because of the size and rural makeup of the state [and] also because isolation, fear, and ignorance keep people from reaching out for support.”

“My experience in Boston is much different and encouraging,” she said. “My experience in Portland has been discouraging.”

There is more support for the transgendered to the south. The Tiffany Club in Waltham, a well-established and active nonprofit,  offers regular support groups, social gatherings, and a yearly conference, among other services. There’s also a network of “Sisters’” groups that gather in confirmed TG-friendly joints to sing karaoke and dance and drink and carry on. There are active groups in Manchester and Durham, but not in Portland. Greater Boston also offers a goodly number of transformation salons, specialty wig shops, and the like.

In addition to finding social life, another challenge I encountered was finding a qualified and open-minded counselor in Maine. I eventually did connect with someone in Portland who has at least a little experience with transgender clients, a non-judgmental attitude, and no apparent agenda, but it took dozens of calls and several failed interviews to find her.

The only time thus far that I’ve dressed outside the privacy of my home was at the Tiffany Club’s annual conference, held last January at a hotel in Peabody. That’s when I first experienced what my sisters on call the Pink Fog: an uncontrolled plunge into feelings of femininity.

At the end of a session on feminizing one’s voice, the presenter invited her star pupil to demonstrate what she had learned. This pupil was my first face-to-face example of how completely — if you have the time and money and determination — you can have yourself changed from a man into a woman. Body, face, hair, voice, carriage and mannerisms … she was absolutely a woman, and she was gorgeous. Instantly, and with disconcerting intensity, I yearned to be her.

In a daze, I wandered into the ballroom where vendors had set out their wares. I tried on wigs. I bought one. I bought my first pair of fake boobs and the special bra to hold them. I picked up some clown-pink, under-layer makeup for concealing the telltale blue of even my closest shave. I told the T-gurls (as some male-to-female cross-dressers call themselves) around me this was my first time out, and they gushed and hugged me and kissed me on the cheek. It was overwhelming and wonderful, and very strange.

For a week afterward, I came as close to crisis as I have since this adventure began. I really felt I needed to come up with $100,000 for hormones, laser hair removal, vaginoplasty and facial-feminization surgery, and then figure out how to tell my family, friends and co-workers I was going to be turning myself into a woman.

I have since backed waaay off from that (thank goodness). The key to backing off was realizing there is a stage beyond which you really are killing off your old male self. I was, and am still not, ready to do that. I don’t think I ever will be.  

So, as is the case for many others, I fall somewhere in the middle of the gender spectrum. I dress when I can. I’m planning my first excursion to the mall en femme — a rite of passage of sorts. My wardrobe will keep growing. I plan to get my ears pierced, and I want to start going out more. Some in my position have opted for permanent beard-removal, by electrolysis or laser. I might look into that someday, if I can afford it. Covering the beard with makeup is a tiresome chore. So is all the body-shaving — an epilator is a definite future purchase. And I plan to buy a “Veronica,” a custom-made, padded garment to round out my skinny man-hips and ass.  

That’s plenty for the time being.

My big secret is not that I am a cross-dresser. My big secret, the revelation I tremble to share with a few carefully selected friends, is that I feel feminine, at least in part. The cross-dressing is just an expression of that. It is not a hobby, and it is not an addiction. It is the long-delayed flowering of an inner truth.

Naturally, I dressed to write this account. Before I change back, I am going to put on Suzanne Vega’s Nine Objects of Desire and practice dancing in heels. “One thing I know / This pain will go…”

So, if you see me out in the world, doing my best to strut my stuff, please don’t mock or laugh at me, and please don’t feel embarrassed, either. I’m just trying to figure out how to be my natural self. And if I smile at you (my only alternative to flight), how about just smiling back and passing on by? What’s the big deal? 

Or, if you are of an old-fashioned, courteous bent, you could hold the door for me. Hon, that would absolutely make my day.


Other Voices

Pre-revelation, I thought I was reasonably well-informed about LGBT issues, but I was wrong about the “T.” I knew almost nothing. Ask me to name three transgender people, and I would have said J. Edgar Hoover, Dr. Frank-N-Furter, and the villain in The Silence of the Lambs. Isn’t that a lovely list?

Since I’m still such a newbie, I posted a thread on asking my more experienced sisters for comments to pass along. Jess, from somewhere in New England, wrote, “[Transgender people] lead normal lives just like everyone else…. We are just born a bit different, but [are] overall nice and decent people.”  

“We are all perfectly happy being this way,” wrote Samantha, from the Midwest. (Not all forum members agree with her.)  

Lorileah, in Denver, wrote, “We are not what you see in the media.  We are not buffoons who use giant water balloons to make outrageous breasts, nor are we all desperate psycho killers or bank robbers. We are not all gay. We definitely are not child molesters. We are husbands and lovers, doctors, firefighters, teachers, scientists, politicians, truck drivers, store clerks, and any other profession there is. We care for our families, our neighbors and our communities. We are not ogres, we are people just like you.”


Lisa Pomeroy is the femme identity of a writer in southern Maine whose male identity The Bollard has agreed to keep anonymous.


Offers chat rooms, infor-mation, products and more.
Local site with information, resources and helpful links.
Web site of the Portland-based Trans Youth Equality Project, offering information, support and advocacy to transgender and transsexual individuals ages 2 to 22.