Confessions Of A Socially Awkward Lover

Reflecting on my many awkward sexual moments — and the lessons learned from them

“Stop trying so hard to be someone you’re not.”

American Actress, Issa Rae

For the vast majority of people, we tend to let external events define us. Whether it’s our past, our careers, or the people in our lives, we often struggle to define ourselves and master our own confidence.

Well, I was no different.

While I have grown much in 27 years of living, I have had plenty of socially awkward mishaps. Especially in the realm of sex — it’s been one, big socially awkward learning experience. Despite what TV would have you believe, sexual moments are rarely sexy. When the topic of sex is brought up, there’s no telling how it could play out.

The many taboos and insecurities regarding sexual matters has lead to a lifetime of learning experiences — and regrettable thoughts.

As a Black man with socially awkward tendencies, I live in a weird state of duality when it comes to attraction. On one hand, due to the sheer nature of just being black with a muscular build, I’m immediately seen as hyper-masculine by virtue of my physical attributes. I’m black, muscular, with a bald head, and I’m often told that I can come off as intimidating when I’m silently observing my environment. On the first impression, I’m immediately defined by my physical form instead of my character.

On the other hand, the truth is a bit further from expectations. I’m nerdy and introverted but will talk at a hundred miles at an hour once I feel comfortable enough. However, for many women, I have encountered they often prefer the built-up image of black stoicism in their heads instead of accepting me for who I am.

There were many “moments” where I nearly lost my virginity. Growing up, I was also shy which meant I was a late bloomer when it came to my own sexual awakening. Ironically, each of those moments almost happened because I was being pressured into it by one woman or another. The extreme discomfort it caused me was a big reason for holding out.

These moments of sexual pressure had a much greater, compounded effect that would follow me for the rest of my life.

A deep, discomfort with sexual intimacy and my own sexual confidence.

Over the years, I had a lot of guy friends and homies try to get me to open up to various women. Suffice to say, when you’re a socially awkward mess, not even the best wingman can get you laid.

Real confidence has to come from within.

When I did lose my virginity at the age of 19, it was also due to being pressured. It was from a woman I met during my brief stint in college. She was insanely beautiful, and for reasons that elude me to this day, she saw something in me. (No joke, I tried to convince her to go for other guys. Didn’t work of course). However, she was quite persistent and made it her mission to have me to herself — regardless of how uncomfortable it made me feel.

While I suppose I should be proud of having my first time in such a way, I actually don’t. To this day, I’m not sure if it’s right for a man to complain about being pressured into sex.

In high school, I would make up stories about women I had sex with to get the guys off my back. (Yep I was one of those). Honestly, I wasn’t trying to impress anyone, but I needed a way to get everyone off my back. I have never cared much for the social dick-measuring contest of “who could get the most girls”.

Reading a good book was infinitely more interesting than trying to pursue women that could care less about me.

Oh, and speaking of the woman I had my first time with, the circumstances of our sexual encounter would lead to a major falling out. A falling out that led me, regrettably, to calling a woman out of her for the first time in my life.

If I had a time machine to fix things in my life, that would definitely be one of them.

As I grew into my twenties, I would eventually develop a drinking habit. See, I was confident in many avenues of my life, but sex wasn’t one of them. It wasn’t due to sexual performance (I always got great reviews!), but it was due to the numerous moments of feeling pressured. Long story short, in order to get in a sexual mood, I had to drink…something.

Cider, Rum, Tequila, Crown Royal, hell fucking anything. I just had to dull the pressure and insecurity inside myself. It’s not the sex that drives me nuts…but the intimacy that comes with it. As a guy that is very particular with his time and space, whenever it gets invaded, it gives me an anxiety spike like no other.

It would take years upon years before I learned to make peace with this. And even then, it’s a challenge.

In a prior relationship, I royally failed in understanding my ex’s sexual exploration. As a black man that was raised in church-filled, small-town Texas, I had a lot of misconceptions about sexuality that I needed to iron out.

Actually, here’s a glorious list of things I sexually fucked up with my ex.

• Not understanding her desire to embrace pronouns.
• Not understanding polyamory, open relationships, and various other relationship lifestyles. Due to my upbringing, I had assumed that monogamy was the only way to live with someone. Suffice to say, that was a fucking lie.
• Misunderstanding some of her more exotic fetishes
• Occasionally, being a slut-shaming asshole because I couldn’t understand her desire for sexual exploration. While I wanted a dull monogamous relationship, she was very sexually adventurous and wanted to explore more. It was more than just finding better sex — but living a satisfying lifestyle that appealed to her sexual needs.

Fuck just talking about her would require a separate draft.

Sexual confidence is hit or miss for me. Physical attraction is okay, but have you ever had a conversation so exciting it lit a fire inside you?

As I entered adulthood, I would later learn that positive social energy and good vibes would be the cure to my sexual insecurity. Being a masculine dickhead and braggadocio just doesn’t work for me.

I once brought a woman home to my house, and in a rare moment of sexual confidence, almost sealed the deal. I romanced her, did the foreplay, built up the moment, and had a delicious kiss. I almost made it to home base…until my mother returned to the house. Immediately, the mood died and we dialed it down.

Well shit.

Military life helped me make peace with many of my sexual insecurities. By interacting with so many people from different backgrounds and lifestyles, it opened my mind to the numerous possibilities of sexual exploration.

It also helped me calm the fuck down and enjoy having someone next to me.

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Dayon Cotton is Active Duty US Navy and Freelance Writer. I write dope articles about social issues, life lessons, and advice on how to live a better life. Stay safe out there!