I Lost My Virginity To My Best Friend’s Boyfriend


I’ve never told anyone more than a vague account of my “first time” if the topic of virginity comes up. I was young, 15. We were drunk. It wasn’t very magical. If pressed for more details, I would lie and say I lost it to a boyfriend.

In the beginning of High School my best friend and co-conspirator was Mary*. Mary and I did absolutely everything together, including a lot of firsts. Particularly a lot of reckless firsts. We got drunk for the first time together, smoked pot and tried various other substances for the first time together, tried our first cigarettes, learned how to sneak out of my house and cut class. She was even there the night of my first kiss, on the couch next to me, and then again in the front seat when I was in the back seat giving my first blowjob.

I adored Mary. She was gorgeous, funny and had an awesome sense of style. She always said the right thing, and acted the right way to come off as the perfect combination of cute and badass.

We dressed similarly, listened to the same music, hung out with the same people. We even adopted each other’s habits and vernacular. We were sometimes considered a single entity.

Then Mary started dating Malcolm*, and our two-some evolved into a three-some. Malcolm was dreamy. He was 17! He skated, listened to cool music, smoked cigarettes and weed, and was totally hot. He was also very into Mary, which I thought was great. (Who wouldn’t be?) I loved hanging out with Malcolm, and the three of us had some pretty great times together.

I was always hanging out with Mary, and now so was he, so we got to know each other pretty well. I would even sneak him into my house when Mary spent the night and he would sleep between us, sneaking out early in the morning to ride his skateboard home.

Mary lost her virginity to Malcolm. She called me that night to let me know. She said she didn’t really feel any different and actually it wasn’t that big of a deal. But I felt a little smaller or childish in comparison. I was eager to join the big leagues. We did everything together, and I was sad that we now had this seemingly huge disparity between us.

Of course I was a little jealous of Mary. I was certainly attracted to Malcolm, and I desperately longed for teenage love. But what I really wanted was my own boyfriend.

Their relationship was pretty tumultuous — it got to the point where one week they were dating and the next week they were broken up. I could barely keep track. Malcolm would call or text me sometimes late at night when Mary wouldn’t answer his calls. I was stuck in the middle of their drama, trying to assuage both sides. I didn’t want them to be fighting. I preferred when we could all hang out happily together.

I don’t remember exactly how I ended up on his mattress that night, with him offering to massage my back. Our flirtation had started casually enough and evolved into a very frustrating temptation that I started to encourage. Malcolm and Mary had recently broken up again. He had probably called me to talk about his distress, and I had probably gone to his house under the pretenses of continuing my counseling in person. I can’t plead total innocence on possible scenarios involving me hanging out with my best friend’s boyfriend alone in his room while drinking alcohol. It didn’t “just happen.” I was complicit in my deceit.

He thanked me afterward. I waited on the sidewalk for my Dad to come pick me up in a sort of a daze, thinking about what had just happened. I wasn’t a virgin anymore. I don’t remember it hurting. I don’t think there was any blood. I lost my virginity to my best friend’s boyfriend. I didn’t feel more mature. I felt dirty. I felt vacant.

They were back together a few days later.

I don’t remember how she found out. It didn’t matter. She was betrayed, and we had our own messy break-up. I was ashamed, am ashamed for how disrespectful I was to my friend, and also to myself. We eventually reconciled somewhat and became friendly with each other senior year. We even hung out on occasion.

Reflecting back on our friendship, I have since come to understand I didn’t just want to be like Mary, I wanted to be Mary. I betrayed her friendship for something as insignificant as sex, because in a twisted way I thought it made me more like her.

I don’t want to say losing my virginity wasn’t a big deal, but the sex aspect isn’t what makes me cringe. It’s the manner in which it came about, and that I should’ve known better. I did know better.

I only recently told one of my friends. For the first time I actually uttered the words “I lost my virginity to my best-friend’s boyfriend.” I was incredibly relieved to finally be able to own up to my past. Astonishingly, my friend replied, “I did too.” I don’t think it makes us bad people. Adolescence is wrought with challenges and hard decisions and bad decisions, and we learn from them.

In the nearly 10 years since, I have grown up a great deal and I have a lot more respect for my friends and myself. While I still can act a little reckless, I like to think I’ve learned to be much more responsible and independent. I have lost touch with Mary, but I still miss her and think about our friendship from time to time. I wish her the best, and hope to catch up with her someday.

*Names have been changed