How I Lost My Virginity As A Transgender Woman

We’re expected to lose our virginity on a special night with someone we love, so we can remember it forever. Like many high schoolers, I couldn’t wait to lose my virginity. But unlike any high schooler I knew, I had extenuating circumstances that prevented it: I was born transgender.

Ever since I was six years old, I fantasized about what my life would be like as a woman. I had no interest in losing my virginity — or doing anything sexual — as a “boy.”

Having sex with the body I was born in didn’t feel right; I was uncomfortable with myself, and I knew I wasn’t “gay.”

So while I had opportunities to have sex prior to transitioning, I was disinterested, and I’m proud that I waited.

 

Our story started in middle school.

I was in 8th grade; he was in 6th. I was his homeroom mentor. The first day of school, I remember thinking how cute he was. Even then, I appreciated a good piece of eye candy. At our respective young ages we could feel the strong energy we shared, but neither of us knew how to act upon it.

While he was making the transition from middle to high school, I was beginning a transition of my own: from male to female.

This didn’t prevent me from having many of the same experiences as my peers, including hooking up. He was the first person to kiss me with passion. The first to kiss my neck, my chest, up and down my body. The first to try unbuttoning my shorts — and the first to be denied. The whole experience was invigorating. But as excited and anxious as I was to release all that built-up sexual tension, I was still wishing I could fully experience a “normal” hook up.

 

Fast forward three years.

It was the summer between my freshman and sophomore years at Hofstra on Long Island.

I had undergone the painful and extensive process of gender reassignment surgery. I was nineteen years old.

Regardless of the unpleasant healing process, I was ecstatic to get up every morning and put on whatever clothes I wanted. Especially thongs! After wearing a Victoria’s Secret bikini, it was time for me to conquer my next big step as a woman: have sex with a man.

I had to wait at least eight weeks to do any physical activity, so as I counted down the days, I planned. My high school fling and I had kept in touch over the years, making out a couple times, and he was intrigued that I had completed my surgery. He was my first choice to take my virginity, and when he invited me over, I rushed to his house. We made out for a while, and I took pleasure in pleasuring him. Then, finally, he fingered me…and…

It was nothing special.

I had waited so many years to be played with yet all I felt was an awkward tickle. I think he was nervous to go farther, but I couldn’t wait any longer. I knew the opportunity to have him as my first might not happen again. Plus, I had no interest in going back to Hofstra a virgin; decent guys were slim pickings there. So after some hesitation, he put on a condom.

Eleven minutes and two positions later, it was over. And it was…weird.

Not painful like I expected, but it definitely didn’t feel as good as I thought it would.

On the drive home, I sang as loud as I could to the song “I Just Had Sex,” which was probably the most enjoyable part of the night.

With the weight of virginity finally off my shoulders, I began to make up for lost time, having sex with practically any attractive guy who looked my way. Sex was great, and a lot of sex was even greater. Although I know now that most of them were never deserving of me, I don’t regret it. I learned so much about myself through my sexual explorations in college.

I haven’t hooked up with my first since that night.

The timing was never right. And though on occasion we Snap each other, I have no plans to see him again. If our paths do happen to cross, and the timing is right for a fun night, I will absolutely have sex with him again. For the story. And the orgasms.

Yes, the orgasms. There’s a big misconception about how transgender people have sex. Some never have surgery and are satisfied with their natural born parts, but want to be perceived as the opposite gender. Those who have surgery, like me, sometimes don’t have the same positive results. Some may never be able to get wet on their own. Some can’t open up their vagina without dilation (they use a dildo with lube to stay open). Some don’t have any vaginal or clitoral feeling at all.

In general, the younger someone properly identifies with their preferred gender, the better the results of hormone therapy and surgery.

I’m lucky to have gotten the surgery when I did. Lucky to not have any of those complications. Lucky to be able to have and enjoy sex. Like many women, it takes a lot to get me off, but I feel blessed to have a beautiful vagina with feeling.

I’m now waiting for the day where I meet a guy, we start dating, and I can express to him (or he could read and know from this) that I want the first time with him to be romantic, I want it to be special. I want to get to know him, make that connection, enjoy our sexual tension, and then finally be able to have him in me, and then have him forever (or until our relationship runs its course). I long for that. I am so lucky to be able to have sex as a woman, and now I can’t wait to have it with the right man.

xxoo,
Corey Rae

Ps. Because we’re accustomed to identify as either boy or girl when we are very young, we transgender individuals often say “I’m a girl trapped in the wrong body,” etc. But really, we’re just transgender, something that has been around since the cavemen.

The Aztecs, Incans, and Mayans, all had gender nonconforming or all-gender sex-related beliefs and fetishes (examples of this can be found on their pottery and other art made from clay.) The Indonesians recognize a third gender, “Intersex.” It is recent in our history that we’ve become so closed minded to anything besides “straight and male and/or female.” Gender is over, and someday transgender individuals will be treated like everyone else.

I wasn’t born a boy, and I wasn’t born a girl; I was born transgender, and that in itself is a very real lifestyle.