'I Want to Be with Women': Confessions of a Trans Trucker

'I Want to Be with Women': Confessions of a Trans Trucker
Published: Mar 07, 2021
In 2016 in Toronto, I boarded a city bus, dropped a token in the fare box and asked for a transfer from the driver, who was very cheerful. I often end up chatting with such types. This one was wearing a wig and makeup and had a low voice, and as we got talking — with a bus full of passengers around us — I learned that she used to drive a truck before she transitioned. Before I got off the bus I asked if I might interview her. A few days later we met and spent a couple of hours talking. — Whitney Smith

Janpanese cross-dressers, journal of wild culture ©2021

The tradition of onnagatas goes a long way back in Japan. [o]


WHITNEY    Let’s start at the beginning. What are your early memories of having a sense that being a boy was different for you than for other boys?

GAYLE    As a child I remember my mother catching me in the bathroom in my sister's clothing. I had two older sisters within a three-year span and a sister two years younger than me. So even if I didn't fit into the clothing, I still had it on. It gave me a sense of feeling comfortable. It gave me a sense of feeling content. I'm positive that I had ADHD or some kind of attention deficit disorder because I was extremely over-active and my mother was always disciplining me. I would dress up and it would make me feel comfortable and give me the peace I wasn't getting within my life at that point.

WHITNEY    Did your peers have any knowledge of what you were doing, or what you were going through?

GAYLE    I remember what the neighbourhood bullies would do to someone who wasn't normal. So I'm thinking, 'I don't want to be labelled not being normal. Don't tell anybody. You keep that to yourself because that would make your life harder. It would be another thing to throw in there that people wouldn't understand.' So you hide that part of it too. So you're hiding your dressing. You're hiding these thoughts of, ‘Am I gay’? You're hiding these thoughts of ‘What's wrong with me’?


I was always attracted to that feminine side of the women and I don't know why I wanted that.


WHITNEY    I’m assuming when you use the verb ‘to dress’, you also mean ‘to cross-dress’.

GAYLE    Yes, mostly. Sometimes I say cross-dressing.

WHITNEY    Was there a turning point, an incident where things changed abruptly?

GAYLE    No. It was put under the carpet. I’ve gone through my life for the most part as a male, as Richard, continuing to cross-dress and paint my nails and wear lingerie under my clothing so nobody would know, fearful I was going to get caught. I drove transport for 24 1/2 years. I used to run coast to coast and dress while I was in the truck hoping I’d never get stopped by a state trooper or provincial police or RCMP, or crossing the border. I was fearful they might find something in the truck. I never got caught.

WHITNEY    How did you feel about dressing when you were in your teen years?

GAYLE    In my late teens I was hiding myself as being a woman and being transgendered through drugs, like weed and acid and whatever we found. Then I found it through alcohol, right up until I was in my thirties. I drank like everybody else. We would call them weekend alcoholics or functioning alcoholics. I would get drunk with my friends Friday night, wake up Saturday morning, hung over and by noon time drinking again. As a functioning alcoholic I stopped the drugs, and then I stopped the drinking when I got into driving transport.

I know a lot of trans individuals that did the same thing. They get involved in their work and they basically bury themselves within their job to suppress and they work to the point of exhaustion. So I was fortunate enough that I got into a career where I was able to work long hours, 16, 21 hours, days running. You get up in the morning, get in the driver's seat and you're driving until you can't drive anymore. Stop for an afternoon nap and then continue driving until the wee hours of the morning. To me, driving truck wasn't a job, it was my life. I had clothes in my truck enough for two weeks. I had my two pair of cowboy boots. I drove in my slippers, I had towels on the floor. I had a built-in fridge, a microwave and a flat screen TV. My truck was all decked out with the throw blankets and the cushions and pillows. It was home and I lived in it.

WHITNEY    Sounds like a lifestyle as much as a career.

GAYLE    That’s right.

WHITNEY    I want return to that later. What was going on with dating and sex in your teens?

GAYLE     My first sexual experience was when I was 16. I was seduced by a 34-year-old woman. It was enjoyable.


Confessions of a Trans Trucker, journal of wild culture ©2021

When Gayle was Richard, 25. 'My first highway truck . . . running New Your City and California out of Toronto. It was all new and exciting.' [o]


WHITNEY     So you were attracted to women?

GAYLE     Oh, yes. After that, and all the heartache that goes with a first romance, I sought relationships with older women constantly. The year that movie came out, in the 70s, In Praise of Older Women, I had to go off and see it. I was enamoured by older women. That's all I've ever dated.

WHITNEY     No lack of attraction there.

GAYLE     No.

WHITNEY     Could you elaborate?

GAYLE     There’s something about the feminine quality of a woman that I wanted, that quality in a lady. I was always attracted to that feminine side of the women and I don't know why I wanted that. What I knew was I wanted that not only to be with them, I wanted that for myself. And again, it goes back to feeling content. It gave me that sense of security. I wasn't sure, because of the dressing, if I was gay.

WHITNEY     Am I right to assume that you were waiting for something to happen with men, with a man?

GAYLE    Yes. The first time I went downtown and into a bar a man picked me up, an older man, and I remember I was wearing cowboy boots. We were going to wherever he lived, we were walking along, and he went into the store to buy a pack of cigarettes. I remember, I just took off. I ran as fast as I could because I, as much as I anticipated what I wanted, it's also something I was afraid of. I've never performed oral sex on a man or had intercourse with a man.

WHITNEY     In your life?

GAYLE     In my life.

WHITNEY     What happened, in terms of your dressing, when you got married?

GAYLE     I was 24 and I was with her for 10 years. I was 22 years younger than her. You hide it from them, do it when they're not around. There was lots of trans or cross-dressers and their partners don't know. They hide their dressing. They keep a stash of clothing, whether it's in the garage or a crawl space, in the car, in the trunk, whatever. They dress when they're not around their partners.

WHITNEY     The cross-dressing was something you had to do, but it didn't mean you couldn't live this life with your wife in all the other ways?

GAYLE     It was almost an obsession with the dressing. I couldn't stop doing it, as much as I tried. And even though I had a relationship with her, I still dressed constantly. There wasn't a week that would go by without thoughts of suicide. I’d go months thinking about ending my life and I could go weeks or months where I wouldn't think of that, then it would come back again.


Louis XIV, confessions of a trans trucker, journal of wild culture ©2021_1.jpg

'What is the most beautiful in virile men is something feminine; what is most beautiful in feminine women is something masculine.' —
Susan Sontag. Portrait of Louis XIV in Coronation Robes, by Hyacinthe Rigaud, 1701. [


WHITNEY     Did you only have thoughts of suicide?

GAYLE     I don't understand whether it’s a disability or a form of depression, where you can't get out of bed, or where you can function but it constantly nags at you. I was never diagnosed with it. I'd never gone to seek help on it. So I wasn't sure whether I was depressed or not. All I know is that I had these thoughts. I attempted suicide when I was 16 with the son of my father’s future wife, in my father’s trailer. For some reason he and I made a pact. We turned on the gas and then we were drinking or smoking weed or whatever we were doing before we got into the trailer. It wasn't long after his mother came in and wanted to know what we were doing. We weren't in there very long to do any damage, but I remember both of us being startled and lying through our teeth, ‘We're not doing anything wrong!’ She could smell the gas and I don't remember what the excuse was, we hit it or turned it on to get some heat and didn't realize it, but nobody suspected anything. We never tried again. And then that passed.

WHITNEY     Did you know anyone who was struggling with the things similar to you?

GAYLE    In my career in trucking I had a friend. There was a big push from the AIDS Committee to get your hair cut and support and donate the money. He went and had his hair all shaved off and was wearing a knitted cap, you know, in support of AIDS. Not long after he parked his truck in Reno, Nevada and walked out in front of a train. I wish he had the nerve to tell me back then because I would've told him it was okay. Do you know? And I would have told him my secret. He lived with me for a year. We were almost like brothers.

WHITNEY     But there was no sexual attraction between you?

GAYLE     There was no sexual there. I wanted to be with women.

WHITNEY     We’ll come back to that. But first, when you were with your first wife, was she aware of the dressing?

GAYLE     No. I guess I was still young and I was still trying to find what I needed. In the first couple of years, I remember one time, she was in the bed and I said, can I show you something? I had her black slip on and her bra. She was a much heavier woman, so it didn't even fit or look good on me. She was nervous, and I came in and stood there in front of her. All I remember her saying was, I never want to see that again. I got undressed and never did it again. Another time, later, she was away for a bit and when she came back she found a pair of women's underwear in the bed. She thought I'd had somebody in there. I didn’t, so I told her the truth. I explained to her they were mine. She didn't want any part of it. She didn't want to know about it. She didn't marry a man who . . . someone who did that. I never heard anything about it after that. The relationship just parted its way and I moved on.

WHITNEY    What happened after the end of that marriage?

GAYLE    After my first wife and I split up I dated half a dozen women within a year's time, looking for that piece that I was missing, looking for that feminine part that I wanted. I was on my own so I was free to walk around my house in whatever clothing I wanted, as long as I didn't go near the windows where my neighbours could see me. Now I'm free.

WHITNEY    Was it in that period of dating you met your second wife?

GAYLE   Yes. And the day my second wife — my current wife — first came to my house I had gladiolas everywhere. I had just come from a town on Lake Huron and one of the farmers was selling gladiolas. I picked up a whole bucket full of them. So when she came to visit I had gladiolas everywhere. She admitted to me later that she thought I was gay because of the gladiolas.

WHITNEY     It happens.

GAYLE     Yeah. So when I first met her, and the sex was good and she was so pretty, very petite and pretty. I couldn’t believe she would want me. I thought I was an average guy and she was extremely feminine. When she first invited me over for dinner she had the table set with all these cheeses and paté. She also that night got me a kitten. So when she went off to the bathroom or bedroom, and came back a few minutes later, the paté was sitting on the floor. She said, “That's my expensive paté!” And I said, “That's cat food now.” I said we’re going out to dinner. So here she's a proper sophisticated woman and I'm feeding her paté to the cat.


So you stop and go back. Suppress your feelings. Back to working long hours. Back to hiding what you're doing.


WHITNEY     So when did the subject of your dressing come up with her?

GAYLE     I've been with her now 21 years, but I didn't tell her for the first ten. I hid my dressing. I didn't tell her anything about it. At that point in my life — I was 33 or 34 — from past experiences I assumed how it would turn out, which would be not good. I liked my relationship with her, I didn't want to spoil it. I didn't want to upset it. Then something happened that changed things. Every so often she’d come with me when I was driving. We were on our way to Kentucky and we stopped at an outlet mall. As we’re window shopping, I saw a beautiful rose print with flowers, on a cream-coloured nightie. I really was taken back by it. We walked around the mall and we came back to it and I said to her, I really like that. She said, if you really like it, buy it. Buy it for yourself.

WHITNEY     Wait. She didn't say, “You want that . . . so you can give it to me?”

GAYLE     No. She said, “If you really like it, then buy it.” She didn't know what she was getting into.

WHITNEY    I believe you.
GAYLE    So I bought it and the first time I put it on in the truck I was embarrassed. I wasn't sure what to do and she never said nothing. But after awhile I would come home and it would be almost like my security blanket. The first thing I would do was come in the door from work and I get into my nightie and after a while she became upset about it. She wouldn't want to have sex. She didn't want me to put it on. She was upset that I was obsessing. So I stopped and again I go back, suppressing, suppress your feelings. You go back to working long hours. You go back to hiding what you're doing. So I take it with me in the truck and I would do it then and then I would come home, when I was home and I would only wear it after she'd gone to sleep because I was used to staying awake. She'd go to sleep and then I would put it on.

WHITNEY    And you'd put it on and walk around the house?

GAYLE    I walk around the house. So we did that for a while. And that would make me feel better. And I bought a couple more of them and she allowed it. And over time I collected quite a bit of women's clothing that she allowed.

WHITNEY    You said that she was upset.

GAYLE    She was upset, but still allowed it.

WHITNEY    And then it changed for her?

GAYLE    No, it didn’t change. She allowed it, she allowed me to purchase items and have them in my closet and I would dress after she'd gone to bed.

WHITNEY    Did you have a conversation about it where it was more out in the open?

GAYLE    Not for awhile. Then it was to the point we did talk, and she said it's not her thing. She didn't really want to know about it and didn't want it thrown up in her face. So we went through our motions of our relationship. I would try to dress only when she was asleep, even though when we would be out shopping, I would say I really liked something and again, she would say well, get it. Or I would come home from work and she would say, I bought you something today. And she would have a piece of woman's jewelry for me or an item that was feminine. I would think, okay, is she going along with me or is she going to drop the other shoe? I was always waiting for that other shoe to drop.

WHITNEY    Through all this you seem to display a great deal of patience.

GAYLE    Thank you. I have a male pattern baldness issue, so I wear a wig. I wish I didn't have to, but it's part of life. So I went and I bought my first wig. I drove down to the city and purchased it and I came home and she wanted to see it. So I put the wig on and she started crying. She said, “It's over. I need to go for a walk”.


Gayle Hollett, journal of wild culture ©2021.jpeg

No more two week runs with two days off. [o]


WHITNEY    It’s over.

GAYLE    It’s over. About a week later, she moved out. She moved in with her brother and I was devastated. I started crying constantly. I didn't think I'd ever cried. Never cried for anything.

WHITNEY     Really?

GAYLE     In most of my life I never cried. You know, you grow up with that, you know, you boys aren't supposed to cry thing. I wasn't that emotional. I grew up in a hard neighbourhood and a hard life and driving truck, it was very masculine and very dominant. Men don't cry, so you don't cry. I spent all my time crying and I lost a whole bunch of weight. I would walk around the city of Toronto when I wasn't working in between runs. I had given up runs in the highway and I was driving a bus in the city. So in between pieces of work, I had two, three hours splits, I would walk and my eating was down to minimal. So I lost a bunch of weight and the one morning I had a handful of sleeping pills, I put them in my mouth and the phone rang and it was her . . .

WHITNEY     Was this the first time she called you since she had left?

GAYLE     She had been calling constantly through the three months we were apart. I'd called her basically crying and asking her to come back, telling her how much I missed her and loved her and and she missed me and she missed our house. She missed the cats. She missed her life.

WHITNEY    And the sleeping pills?

GAYLE    I had them in my mouth. I was tucked up in bed. It was early morning, the sun was out. Around 9 am. The phone rang and I picked it up and she said, “What are you doing?” I was crying. She said, “I'll be there in an hour.” I spit the pills out and they were all a big blue goo in my hand and I just put them on the night table. All I remember is her showing up and I never did end my life.

WHITNEY     Two near misses. Each time a woman shows up and says, “What are you doing?”

GAYLE     You’re right.

WHITNEY     Since you’re still together, we know something got patched up.

GAYLE     I promised her I would pack everything up and live the normal life again, you know, go back to being Richard. All my clothing and a black fur coat, some of the clothing wasn't cheap. Two boxes full. I wasn't ready to throw it out and give up that part of my life, but I wanted it gone so I put it in the crawl space. And a few months later, I called home one night and she said, “I have a surprise for you.” I thought she'd bought me something, and I come home and there's a card sitting on the table.

But I have to tell you something first. I had stopped drinking way back, for about twenty years, but she liked her wine and it didn’t take her very much. It’s not that she’s an alcoholic, but it was an issue for us at times.

So, I come home and pick up the card and open it and on the card it said “Life is a journey.” In the card she's telling about her drinking and she said, “I have my life and you have yours and you won't judge me for mine and I won't judge you for yours. Life is a journey and you need to lead it. Don't stop being yourself.” And at the end of the card she had written, “I’ve managed to get all your clothing out and hung it up in the closet, and all your personal items are in the drawers. You need to follow your heart.” She made the ultimate sacrifice, as far as I'm concerned, because she didn't know where that was going to lead. How she got it out from there because they were heavy boxes is beyond me, but she allowed me to go back dressing again because she knew that made me happy. That gave me that sense of contentment.

WHITNEY    So you now had what you wanted?

GAYLE    I did. Even though I said to her, back there after the pills, I would try to be different, I don't know if I ever was.


It’s not like I’m in a midlife crisis and I want to wear women's clothing. You don't ask for this.


WHITNEY    Many of the things you’ve said relate to how you felt inside yourself, but also, I think, how you wanted to see yourself and how you wanted others to see you.

GAYLE     Yes. I can say that it's not something that you wake up with when you're five years old and think, “Oh, I want to dress in girl's clothing.” All I knew is that I wanted to be a pretty girl. I liked the clothing, I liked that feminine part. But I would look at myself in the mirror and I couldn't see any resemblance to female. Yet when I put the clothing on, I could see it in my eyes. I didn't see it in the rest of my features other than the eyes and the clothing. I felt it inside of me, but externally it didn't match. So I started putting on makeup and now I was looking in the mirror and I could see something more feminine than I had seen before.

WHITNEY     Did you go out in public when you were dressed?

GAYLE     I would seem more feminine when I would go to my dinners or the Pride marches. I would get dressed a couple of times a year. The first time I ever did, I was very nervous about leaving the house dressed. Not only because I didn't want to upset my wife, even though she knew where I was going. I asked her if she wanted to come. She wanted no part of it.

WHITNEY     So when did it change?

GAYLE     It was a while later. We went away to Las Vegas and she allowed me to dress pretty well much the whole vacation as Gayle. I was on top of the moon. I came back and booked an appointment with my doctor and went without even telling my wife and I went to my family doctor who had no clue about me. Before I got to see him I was with the nurse practitioner and I said to her, I need to transition. And I explained a bit of my story to her and we started hunting. She made an appointment with an endocrinologist and in the meantime, I got on the computer and through trans friends that I had in the province I was looking for a doctor that would see me to prescribe hormones. I explained what I was doing to my wife.

WHITNEY     You wanted hormones, but was there any expectation you would have surgery?

GAYLE     I didn't know. I just knew that I wanted to change. I wanted to be more feminine. I wanted breasts, I wanted softer skin. I had started going for laser treatment on my face to get rid of my whiskers. Then I got the call from CAMH [The Centre for Addiction & Mental Health] and they said they had a referral to bring me in to have an assessment done for gender dysphoria. Not too long after I was on hormones and on a waiting list for gender reassignment surgery in about two years.

After that, I was feeling more content about myself and more at peace. I don't know whether it was losing the testosterone. And I think that has something to do with it because you don't have all that aggression, all that male hormone running through you.

WHITNEY     Did you ever have second thoughts?

GAYLE     I had struggled all my life with it. It's not something like, 'I want a sports car! I want a vagina!' It’s not like I’m in a midlife crisis and I want to wear women's clothing. You don't ask for this. It's within you and you either deal with it or you commit suicide or you suppress it and hide it.

WHITNEY     How was it for you to have the surgery?

GAYLE     So my wife and I go up and we're sitting in a waiting room and there's myself and another man having what I’m having and a woman who was there for breast implants. The operation was fairly quick, like an hour and a half, two hours. In the surgery this gauze is sewn in on the V, all the way from top to bottom. And what they've got, and I didn't know at the time, they have a condom in your vagina. And they use the skin from your testicles to make the labia for the vagina. They use the head of the penis to make the clitoris. You can have an orgasm with it too.

WHITNEY     Functional.

GAYLE    Oh, yes.


Live your life. Be yourselves. Life goes by way too quick.

WHITNEY     How does your family respond to it?

GAYLE    Some of my siblings don't believe in what I needed to do, so we don't talk. The only person in my life now is my older brother. He has been great. My mother still talks to me and my father passed away. I never did get a chance to tell my father. I think he would have been okay. But those siblings who are not with me, they are gone and that's okay. I'm good.

WHITNEY     What would you say to young people who are having the kinds of feelings you’ve had?

GAYLE     What do I tell them? Live your life. Be yourselves. Life goes by way too quick. I don't want to be 78 and have a regret. I don't want to regret not being who I really am. I want to be a happy person. And that's doable, it's functional. Life is functional. But there was always that nagging question, where do you fit into society? Am I gay, am I straight, heterosexual? I am now looking at joining a lesbian group. I really do see myself as a lesbian. I am attracted to women, I am with a woman. I don't want her to have a label, that isn’t fair. She didn't start off liking women, and if anything happened to me, she said she would rather have a companion as another woman, not a man anymore since being with me. But that doesn't make her a lesbian. And if we're going to label something, I would have no problem. But now . . . whether they're going to accept me, that's my question, right? Would they accept me as a woman? ≈ç


WC para break


GAYLE is a bus driver with the Toronto Transit Commission. She lives north of Toronto with her wife.

WHITNEY SMITH is the Publisher/Editor of The Journal of Wild Culture. He lives in Toronto.





Submitted by Joseph (not verified) on Tue, 03/30/2021 - 11:25


Whitney, I read this article just before Time Magazine published their cover story, "Elliot Page is Ready for this Moment" https://time.com/5947032/elliot-page/ . I enjoyed both articles equally. The experiences of Gayle and Elliot were interesting to read side-by-side. Both share their struggles with gender identity, disclosure, acceptance and community. There are many similarities shared by Gayle, a trans female trucker, and Elliott, a trans male actor.

Tue, 03/30/2021 - 11:25

Add new comment