How I Lost My Virginity and Found Love: A Story of Masculinity and Manhood

When I was a boy I once tried walking in my mom’s heels.

My father told me to get out of them and not do that again (I am quite fortunate he did not handle it as the situation played out in Empire).

I often wore a pink shower robe even when my friends came over.

I did not masturbate and I did not seek to have sex even when all of my brothers and friends began to.

Had it not been for being peer pressured in college, it is highly likely that I would still be a virgin today.

I did not like the sport of football as my brothers did.

I often found myself being friend-zoned by women because I would listen to their emotional relationship challenges and offer quality advice.

I can remember a girl who I’d liked for sometime around a year between the 7th and 8th grade. We became very close friends and dated for 3 days before she broke up with me. She said it felt weird to date someone who she was such good friends with.

I did not see it coming and I was emotionally distraught although I never expressed so externally. I was embarrassed and did not know who I could talk to about my heartbreak. My parents had forbid me from having a girlfriend until I was 16, and it was an unspoken rule with my guy friends that we did not talk about our feelings with one another.

I never cried about the incident.

Instead I suppressed my emotions and vowed to never be vulnerable with a woman ever again. I would become distant and emotionally unavailable.

And for many years it worked for me.

I had forged it as a part of my masculine identity. Many more women became attracted to me and would use words such as “mysterious” to describe me. They would tell me they wished I would be forthright about my feelings, but I had seen the results in my newfound stoicism — I knew that to let them past my mask would be to expose myself to the same danger I had experienced in the 8th grade of not being perceived as masculine enough.

I had torn out my ability to feel and had no intentions of putting it back.

While the incident itself was quite abrupt, my transition to emotional disconnection was a rather progressive process.

It was the exposure to a hip hop culture that spouted the ideology of “we don’t trust these hoes.” It was my friends and I bragging about how many girls we had hooked up with and ridiculing one another if we seemed to be developing a connection with one of our female partners.

I have never been one to much succumb to peer pressure, but as I reflect I can see the many ways it seeped into my values and decisions. After a night out, the guys would link up the next day or talk in a group chat about who did what. Who hooked up or had sex with girls from the party or bars.

My freshman and most of my sophomore year I remained a virgin and my friends would often laugh about it or make fun of me. For a long while I did not mind — I have always maintained a high self confidence and image — but late in my sophomore year I had decided I no longer wanted to keep what had become more or less my secret amongst the guys, and something I certainly did not want any girl to find out for fear of being seen as a prude or less the masculine patriarch they might have perceived me to be.

I decided to have sex with a white girl who had been pursuing me at the time. I did not have any feelings for her.

I did not feel bad afterwards, nor did I regret it the next morning. I proudly announced it to my brothers and friends who all congratulated me.

I no longer had to live with the secret of being a college boy who was still a virgin.

I was officially initiated into manhood (or so I was told).

To this day, I can count on two hands how many times I have had sex, but society does not much care as long as I have ridded myself of the shameful label of virgin.

It was a year later that I met a girl a few years younger than I, who I thought was both cute and nice. When we first began talking, I’d had no expectations of dating her. How could I when I’d stripped myself of my ability to feel or engage in emotional intimacy?

We began to text and hang out frequently. So much so that I began being questioned what was up between her and I more times than I would have liked. Female friends of mine began to ask if I liked her, to which I’d quickly respond “no” for the simple reason that I no longer even knew what it felt like to like someone.

I liked to be with her and around her, I liked her sense of humor. Yet, I could not possibly fathom being completely emotionally vulnerable with her. As the weeks passed, however, that is exactly what happened.

I had somehow let down the wall that I spent many years building up. My mask of emotional stoicism had began to crumble. It was not that I felt forced to, but rather than I wanted to (which was a strange and inexplicable feeling in and of itself).

When she first asked me about my feelings I went silent; the former debater, student government senator, rapper, “good public speaker,” in all other things articulate but yet could not find the words to describe how I felt.

I could not remember the last time I had even tried to.

She would tell me she did not need an answer then, just that I think about it. We would have to do this many times and even today I still struggle to do so.

It is her though, the woman I am with now, who taught me that real masculinity is not formed by faux-strength, emotional distance or being perceived as an aggressive and fearless protector.

Healthy relationships do not work when one person is emotionally withholding or unable to express how they feel.

Today, not only is our relationship’s foundation stronger, but I have and still am becoming a more wholesome, creative, and loving human being.