Despite being a very early masturbator (and a pro at giving myself orgasms at a young age), I had never been able to achieve an orgasm with a partner. Not during intercourse, not during oral, not at all, ever.
With my first boyfriend, I assumed we just hadn't figured it out yet by the time our year-long relationship ended. He wasn't the most adventurous person during our sexual encounters. So I was certain that my second boyfriend, who was more experienced and open-minded sexually, would be able to make me come.
We had all kinds of sex. Slow, sensual sex. Rough and wild sex. Silly, low-key sex. Yet still no orgasm for me. Of course, I faked orgasms every time after the first few times in which I never reached climax. By my third relationship, my orgasm-faking skills had reached a level of nuance that sometimes left me wondering if I actually had reached orgasm. But based on everything I had heard from my female friends, I was pretty sure that I would've known if I had.
Don't get me wrong, I still enjoyed sex. The closeness, the sensations, the thrill of it were all things that I craved on a regular basis and there were very few dry spells during any of my relationships.
Years went by and I dated and slept with a steady series of men. But after an extended bout of singleness, I decided to try approaching sex the way men stereotypically do: I started having periodic one-night-stands. I thought I might be more likely to orgasm if I took some of the emotional attachment out of sex. Alas, despite several sex-and-only-sex encounters, I was still unable to unlock whatever door was sealed so tightly inside of me.
So I began to look more closely at my dating patterns and realized how I had chosen people that were unavailable to me, people that I knew I could never really have, people that I knew would eventually leave. I became more aware of the ways I had tried to keep them by molding myself around their desires, rather than owning my own.
I was whoever they wanted me to be, particularly in bed, and left little room for the vulnerability of what it would mean, and feel like, to be my authentic self. I had been ashamed of my early discovery of my own body and the ways I felt dysfunctional by not being able to give any of my partners my ultimate surrender, despite desperately attempting to will it into happening on many occasions. I forfeited my own pleasure for my partners' egos and assumed the role of pleasure-giver out of fear and resignation.
As all of this became clearer, and it took a great deal of time, I could no longer ignore my own needs. I began to listen more closely to my gut and the voice that said, "this isn't right for me." I began to speak my truth out loud, and let the people around me choose whether they wished to accept it or not, to accept me or not. I became clearer on what I wanted and deserved and more able to let those go who could not or did not want to give that to me.
And then, after years of being single and learning to be fulfilled on my own, someone came along. He was kind, smart, and so full of love. I began to open up, in a way I never had before, and was the most unbarred version of my dorky, romantic, neurotic self. I told him when things bothered me and didn't apologize for my needs. I told him about my closeted masturbation habits and exactly how I pleasured myself.
These were all things I had never shared with another partner and, though some part of me was scared, I knew that I was safe with this person who held me as though I were a treasure. When I was least expecting it, I came with a partner for the very first time. After over a decade of sexual experience, I finally figured out the key to being able to orgasm during sex.
I'm not going to tell you what exactly happened, because the technical and mechanical details don't matter. The only one-size-fits-all orgasm guarantee doesn't account for the importance of trust and deep vulnerability. It took me well into my thirties to be able to trust both myself and another person enough to completely let go, but now that I've experienced the bliss that can be found in soul-baring nakedness, I have to say that it was completely worth the wait.