How I Lost My Virginity Three Times
A Touchpoint True Story About Exploration
This story was originally told at Touchpoint in New York City on August 1, 2017.
At 8 years old, I made friends with a set of fraternal twins in my neighborhood — a boy and a girl. One day, we built a fort, took off all our clothes, and just started touching each other. I didn’t realize it then, but those early explorations would serve as a window into how I later lost my virginity — three times.
16 years old
Sara and I were both “choir dorks.” She was a year older than me. She was short with giant, sweet, brown eyes, dark skin and hair, a big beautiful smile, and probably the largest breast of anyone I’ve ever slept with.
She wasn’t a virgin and was remarkably comfortable with her body and ‘how things worked.’ So I knew when the time came, she’d be a good partner to explore.
During sophomore year, a group of us (‘choir dorks’) planned a camping trip over a long weekend. We all shared a tent. To be clear — it was a large tent, and we all had our own private spaces. But as Sara and I laid there, listening to our other friends ‘getting it on,’ things started moving for us. And that’s where it happened.
Yep. I lost my virginity the first time in a tent beneath the stars while listening to the symphony of my other friends also having sex.
I felt excitement and relief. I was also incredibly insecure. “Did I do that right? Did you come?” I asked. To be honest, I don’t remember the rest of the conversation. But I do remember her comforting me — holding me in her arms as we fell asleep.
19 years old
“Come and talk to me when you come out of the closet,” said David as we left rehearsal. He was a senior and I was a freshman. We were both in the theatre department. He was a bit taller than me and a beautiful dancer with pale skin, greenish brown eyes, and big full lips.
During our first semester, our relationship was purely friends. I had never hooked up with a man before, and wasn’t ready to confess that I was into it.
By second semester, I had done a little exploring with a guy — no sex but all the other things — and the rumors spread. David invited me to a ‘porn party’ at his house where everyone dressed up as slutty as they could, porn was playing on all the screens, and there were cut-outs from magazines on the walls.
At some point in the night, he leaned in to kiss me, and soon we were in a full-on, monogamous relationship. We were not having sex because I wasn’t ‘there’ yet, but I had never felt more free in my life. I was really happy for the first time in a long time.
About two months into dating, I told him I was ready. He explained to me that he was strictly a ‘bottom’ and instructed me how to ‘top’ him. For those who don’t know, that means he wanted me to penetrate him. I was a little intimidated.
It was incredibly intense — for him. For me, it was pleasurable at some points, but the whole thing felt a little manufactured, and once it was done, our relationship became less and less sexual.
Not too long afterwards, we broke up.
20 years old
During our first rehearsal, Philip pulled me out into the hall and told me that I “better bring what I brought to the audition or else.” He scared the sh*t out of me.
He was an acclaimed director, hired by the theatre department to workshop a play, and his presence was palpable.
He was twenty years older than me, tall, muscular, dark hair, with striking brown eyes.
One night, Philip invited me out to a gay bar so we could get to know each other better. He asked me questions that no one had ever asked. They were intimate inquiries about my life, fears, and visions. He made me feel seen and understood in a way that I had never experienced. He articulated how sensitive I was and seemed to ‘get’ me on a heart level. It was a connection that was new and magical.
Looking back, that was probably manipulative, considering he was 20 years older and I was a student and a cast member in his production, but nonetheless, it felt good and right at the time.
A week later, he invited me back to his hotel room after a day of rehearsals, and things got heated very fast. Suddenly, we were kissing. Then, our clothes came off. And then, he was inside of me. I’d never experienced that before.
It was an absolute out-of-body experience. After what felt like only moments, I lost all feeling in my hands and arms. My eyes rolled back. It was as if I lost all consciousness. It was ecstasy. I had never experienced pleasure like that in my life.
Philip stopped abruptly because I had practically passed out. He called a friend of his who was a sex therapist for consultation. Within a few minutes, I recovered and we laid together for the rest of the night.
That evening, I discovered sensations I never knew were possible and an unparalleled sense of human connection.
We continued to sleep together for a while, but it was never the same as that night.
Today
All of my ‘firsts’ certainly laid the groundwork for where I am today.
I’m in a long-term romantic partnership with a woman who loves me for all of me and is willing to navigate difficult waters so I can be the fullest expression of myself. We’ve been together for many years.
We’ve explored a full spectrum of relationship archetypes from openness to monogamy, as I still crave intimacy with men. Our work has been to stay in flow as our boundaries are ever-shifting and we continue to evolve as individuals.
It’s been the most difficult and rewarding work I’ve ever done.
I’m constantly striving to connect on a deeper, more intimate and connected level with her as well as others I engage with, and she is the most supportive of me.
On some level, I think we’re all just curious kids in forts made of sheets trying to figure it out. That’s sex. That’s life.
