The First Time I Had Sex in My Correct Gender

Losing your virginity isn’t necessarily the biggest first in your life. Here, one woman shares her most significant sexual first

(Art: Leo Tapel)
(Art: Leo Tapel)

“I knew something was off as soon as I could comprehend gender. Like how most people have never gone a day questioning or feeling dysphoric about their gender, I’ve never gone a day without. I remember how I felt as a kid, 7 or 8, looking in the mirror wearing my mom’s clothes, putting my little feet in her heels—it was the best and worst feeling at the same time. It was putting down one weight and picking up another.

Through my teens, into my 20s, I would go through the typical process of binging and purging: buy clothes and makeup, throw it all out, buy more. Then, eight years ago, I met my wife, and I told her I liked dressing up before I told her I loved her. The first thing she said was, ‘I’m never going to let you throw out this stuff again.’ It was really the first time where I was like, Oh, I can have a normal relationship with someone and not hide this huge secret about myself. She was 21 at the time; she thought it was fun. We went to Victoria’s Secret and bought each other a pair of undies. There were moments where I was like, Holy shit, my girlfriend and I are having sex, and I’m wearing femme stuff and my nails are painted and we’re both totally aroused by this. It was good enough at the time.

But if I wanted to go home and dress up or paint my nails, then no one could come over. I felt like I was making her lead the double life I had, and she was getting used to having this secret. Transitioning only recently felt within reach: I had been on a two-year waiting list at CAMH [Toronto’s Centre for Addiction and Mental Health]. I finally got the appointment and they were like, ‘Yeah, you clearly have gender dysphoria’, and I started hormone treatment. I got cold feet just before our wedding in the fall and stopped for a month, but once I stopped, I knew it was wrong—I knew there was no alternative. I went back on a regular dose and everything felt really clear. I wish I had done this 10 years ago.

Since transitioning, my wife and I have way more vanilla sex. There was always something between us before: a nightie, makeup, sex toys, a prop. But now, I don’t need breast forms because I’m growing real boobs. Before, it was like, ‘I’m home, better put on my bra.’ Now it’s like, I’m home: take off the bra. The experience now is more about two bodies having sex, rather than costumes and stuff. Before those clothes were part of my normal wardrobe, they represented an escape, and after I had an orgasm, it meant that I had to take the clothes off again and go back to guy mode. So orgasms were weird—I’d get really depressed or ashamed afterward. But now I don’t have those feelings. I love coming now, it physically feels better, and I don’t feel screwed up or confused afterwards. It’s just, That was a great orgasm. I feel better in general.”—As told to Danielle Groen 

More firsts:

The First Time I Had Sex After Getting Sober
The First Time I Had Sex After Opening Up My Relationship
The First Time I Had Sex After Giving Birth
The First Time I Had Sex After Being Assaulted
The First Time I Had Sex with Myself
The First Time I Had Sex After Major Surgery
The First Time I Had Sex After Coming Out
The First Time I Had Sex After an Abortion
The First Time I Had Sex After My Marriage Ended