I Kissed a Boy
By: Robyn Sinéad Sheppard
Tags: Life, Transgender Woman, Gender Identity

I Kissed a Boy

And I Liked It

“One is not born a woman, but becomes one.” –Simone de Beauvoir

I was thirteen years old and already feeling the first stirrings of what would late be called gender dysphoria but which in 1963 didn’t yet have a name. And 13-year-old little Bobby didn’t know enough about life to even consider talking to an adult about it. But even then, I knew that there were certain things one didn’t mention to adults. Especially when the adults were your own very conservative Christian parents. Even worse, when you were a Preacher’s Kid (PK).

Anticipating by decades Jame Gumb’s scene in “The Silence of the Lambs,” I was already practiced at tucking my penis between my legs as I stood in front of the full-length mirror in our bathroom, trying to see what I would look like as a girl.

When I was born, and for many years afterward, my parents believed that they had a son. After all, I had the requisite plumbing, so they raised me — nowadays we’d say socialized me — as a boy. They gave me a boy’s name — Robert — the whole nine yards. Boy clothes, boy toys, boy everything.

I hated the name, Robert. At least they called me “Bobby” when I was younger, and that was a girl’s name, wasn’t it? Bobbie?

It wasn’t until I was about six or seven that I began to realize that something wasn’t right. It wasn’t anything in particular. There was no blinding flash of revelation, no epiphany, just the increasing feeling that I somehow didn’t quite fit, didn’t belong. And when I finally saw my first naked girl (my 6-year-old girl friend’s 4-year-old sister), I had my first clue. I looked at the nothing that she had where I had something, and asked, “What happened to it?” The answer, of course, was that nothing had happened to it; that was just the way it was. More questions revealed the fact that all girls were that way.

But more than that, it showed me what I wanted. Not to be a boy.

Years passed. By now I was thirteen and had a new best friend, Tommy. We played together a lot. Did I say “a lot”? We were joined at the hip. One day, in his bedroom, he asked me if I squirted yet. I had no idea what he was talking about, so he showed me. My first hand-job. Later we progressed to mutual hand-jobs, then to oral and anal sex. I always preferred to be on the receiving end, being “the girl.”

Finally, I met the girl who would set me free.

Kathy was my other best friend. She was my age, and we had a few classes together in junior high. She didn’t seem to treat me any differently than any of her other girlfriends. I mean, I saw how she acted with boys, and she was never like that with me.

One day we were playing in her room and she decided she didn’t like what she was wearing. So she changed into a party dress, right in front of me. I thought nothing of it; it wasn’t sexual. It was just a friend changing clothes. When she had it on, she asked me if I liked it. I told her not only did I like it, but I wished that I could wear something as pretty. Ten minutes later I was also wearing one of her party dresses. But not just the dress: socks, panties, everything. From the skin out, I was a girl.

What amazed — and frightened me at first — was that it just felt right.

This continued for a couple of years. Wearing Kathy’s clothes in her room, and being Tommy’s “girlfriend” in his. Later, when we had all parted company (growing up in a military family is destructive of long-term friendships), I had to go back to being a “boy” full-time. Bobby was hidden away and never got a chance to come out to play.

From time to time — especially when I started high school — the only comfort I got was from sneaking into my parents’ room when they were at work and trying on my mother’s clothes. Later, I found great comfort by simply sitting on the floor in her closet, surrounded by her dresses and skirts.

It’s easy, now, to see why I never told anyone about my shameful secrets. Although I was starting to realize that I would be happier as a girl, I also knew that what I was feeling was wrong, shameful, and unacceptable. I was raised in a very religious household, and there were strict rules about was and wasn’t acceptable behavior. From the comments my father had made from time to time, I knew that if my secret ever came out, it would cause serious problems.

By the time I finished high school, I had buried Bobbie and all but forgotten about her. Still, I’d find myself watching girls at school and studying them. But not in a sexual way: I watched how they walked, how they behaved with others, how they dressed, and how they expressed themselves.

With hindsight, I can see now why none of my friendships, relationships or marriages lasted: everything was built on a lie.

Photo by Llanydd Lloyd on Unsplash

It Was All an Illusion

The illusion being, of course, that I could continue to be someone or something I wasn’t.

Finally, when I was 59, it all came out. The house of cards I had spent so many years constructing came tumbling down in a storm of tears in my therapist’s office. The mask came off and I took the first steps on the path to freedom.

I’m not sure why I’m even writing this story. If I had to guess, I’d say it’s because I know that I’m not the only one to have gone through what I went through and to let you know that while it’s hard to be your true self, it’s even harder to continue living the lie.

It does indeed get better.