My High School Boyfriend Gave Me a Sex Ultimatum

I’m now in my mid-forties, but I still have no idea what I want sexually

Photo by Anton Chernyavskiy on Unsplash

by Ainsley Cunningham

When I was 16, my boyfriend sat me down and told me I needed to have sex with him or, at the very least, give him a blow job. Otherwise, he’d be forced to break up with me and find a girlfriend who could meet his needs.

I told him I’d have to think about it. I was getting ready to leave on vacation, and I said I’d give him my answer when I got back. I felt proud of myself for handling things so maturely.

In hindsight, there shouldn’t have been much for me to think about because, first of all, I didn’t want to have sex with him. I didn’t feel ready mentally, emotionally, and maybe even physically. I enjoyed making out with him, which we did often and for great lengths of time, but at that age I didn’t feel the desire to go any further. As for the blow job suggestion, it didn’t sound pleasant to me at all.

The ultimatum itself should have been enough for me to break up with him. But I didn’t. I’d been conditioned by media and culture and everything else to be a nice girl who considered other people’s needs before my own. I’d also been taught by TV and movies that boys needed sex, and that girls had the impossible but important task of figuring out how to not be a slut but also not be a prude.

So yes, it was a lot for young me to think about. He was, at the time, my dream boy: a tall, handsome skateboarder who liked all the same punk bands that I did. We laughed together. He had his own car. We made a good-looking couple at junior prom.

While on vacation, I wrote my thoughts and feelings to him in an embarrassingly long letter. I don’t remember what exactly I wrote, but I recall the overall sentiment. I liked him so much, I said, and I wanted to make him happy, and so if that meant doing sex stuff, I was nervous, but I was open to it. We could discuss more when I got home. I mailed the letter, feeling good about my decision. I was willing to make compromises—wasn’t that what real relationships were about?

I never found out if he received my letter because as soon as I got back from vacation, several friends called me, all with the same news: My boyfriend had cheated on me. He’d had sex with another girl at a party while I was out of town.

I called him to ask if the rumors were true (yes, he said sheepishly), and then—not yelling, not crying, being diplomatic and calm—I said something like, “Well… I guess maybe we should break up?”

I think I was hoping he’d say no. That he’d say he’d made a mistake and he still really liked me. He wouldn’t cheat on me again, and we’d figure out this sex conundrum together. Maybe he’d even ask what I needed, what he could do to make me happy.

“Yeah,” he said, “I guess we probably should.”

One year later, in 1999, American Pie was released, a movie in which the heroes, four teenage boys, set out on a “noble” quest to lose their virginities. I saw it in the theater with friends and didn’t realize at the time, but now I do: If the goal is for the male protagonists to have sex, then the girls “withholding” sex are either the antagonists or, at the very least, they’re obstacles to be overpowered.

The incident with my high school boyfriend is indicative of so much that came later in my life. It showcases the way I’ve always put other people’s needs and desires above my own (“Of course I can work late again,” “I can skip my yoga class to watch the kids,” “Where does everyone else want to go for dinner?”), and the way I’ve always been willing to give more than I receive when it comes to my body, my time, my energy, my compassion—a trait that hasn’t been trained out of us women on purpose because it comes in oh-so-handy when we become mothers.

I always thought of myself as open-minded, extremely willing to compromise. But it’s not a compromise if I’m simply doing what the other person wants me to do. Finally, somewhere in my early thirties, I realized I wasn’t diplomatic and open to compromise. I was a doormat. And then the shame spiral began. I didn’t blame the men who pushed and manipulated me into doing things I didn’t want to do. Instead, I blamed myself for not having the confidence to say no. I blamed myself for not staying true to my own desires.

Part of the problem was that I didn’t even know what my own desires were. Millennial women like myself were completely mind-fucked by the media and culture of the 90s and early aughts: We were instructed to look and act sexy but also remain virginal. Don’t be a frigid bitch and don’t be a cock-tease, but if you have sex, or too much sex, or if you seem to like sex too much, then you’re a dirty slut who deserves to be shamed.

When it came to looking and acting sexy, the desired result only had the male gaze in mind. A woman’s goal, according to the magazines I read and music videos I couldn’t escape, was to please men. Being wanted by men was so important it left no space to learn what we actually wanted. It seemed to me that sex was a performance, a bargaining chip. It was the only thing I had of value, and my only power was to decide when to give it away. It was back to that old balancing act: Give in too quicky and you’re a slut; wait too long and you’re a prude.

Now I’m in my mid-forties, and, like many of the friends I’ve discussed this with, I have very little idea, at least when it comes to sex, what it is I truly want. I have so little practice at putting my own needs and desires first. What if my needs and desires conflict with my partner’s? What then? Cosmo, with all its blow job tips and calorie-burning sex moves, never prepared me for that.

When I was in my early thirties, after a more than a decade of dating and many bad experiences with men who seemed stuck in an American Pie mentality—men who went on dates not to get to know me but to get in my pants—a man contacted me on an online dating site. I had recently moved and had forgotten to change my location. I told him, “Oh, sorry, I don’t live in the area anymore,” and he said that was okay, maybe we could just be pen pals.

We started writing to each other. He was funny and weird and smart (just my type!), and soon we were writing two or three emails a day. After months of pen-palling, I drove the eight hours to visit him. A month later, he flew to visit me. Thus began our long-distance relationship. By that point, I already knew this relationship would be different from so many of the others. He had been perfectly willing to write to me with no expectations of ever meeting in person. He wasn’t interested in me for my body alone. He was interested in me for my mind, my personality, (my writing, even!). We’ve now been married for over ten years. During this time, we’ve been figuring out “sex stuff” together.

Sometimes he still gets frustrated with me because of my baggage when it comes to sex. Too often I resort to my old ways of trying to figure out what it is he wants in order to make him happy. I’m still conditioned to disregard any desires of my own except the desire to please others. “I wish you’d just tell me what you want,” he’ll say, and I’ll respond, teary-eyed, “That’s the problem. I don’t know.”

Recently he said to me, “I’ve come to realize that my role is to be here for you. To put my own needs aside for now and reassure you that I’m not going anywhere. So you can take your time to figure out what it is you want.”

Wow. His comment begs the question: What do I want? I don’t have a simple shorthand, a turn-on cheat sheet to hand over. Even now in middle-age, the damage from my high school boyfriend (and all the men who followed) flares up whenever I try to truly inhabit my body. Figuring out what I want is more complicated than it sounds. So I told my husband what I told my high school boyfriend: I’d have to think about it.

Ainsley Cunningham is a SAT/ACT tutor, yoga instructor, and aspiring novelist. She lives in Virginia with her husband, two kids, and two cats.