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Losing My Virginity, and Other Horrible Sexual Escapades

I had my first kiss when I was sixteen and lost my virginity when I was seventeen. It was a busy couple of years.

The kiss was during my junior year of high school. It was a Friday night and we had just finished a production of You Can’t Take It With You, a Pulitzer Prize–winning play in which I played Essie Carmichael. It was a juicy part. Not the lead, but a good, meaty role that allowed me to show off my acting chops. (I love beef references, dear reader.) After our performance, some of the seniors in the cast rented a hotel room in downtown Seattle. I told my parents that I was spending the night at my friend Stephanie’s (yes, Stephanie was also my alibi during the Stone Temple Pilots concert where Chad and I first hooked up—“staying at Stephanie’s” was a recurring theme of my teenage years), but instead I went to the hotel room and got wasted. It was my first time being drunk, and Kyle, a senior, held my hair back while I vomited, which anybody who has ever been a drunk girl in high school knows is both disgusting and the epitome of romance all at the same time. After I was done puking, we crawled into a bed where Jeff (the same Jeff who I mentioned might murder me) was already passed out. He was lying on the right side of the bed, Kyle was in the middle, and I was on the left. I don’t know how Kyle could stand kissing me after I vomited, but we made out a little bit and then he fingered me right there in that king-size hotel bed for three. (In hindsight, maybe Jeff is right to want to murder me.)

I had a minor crush on Kyle—he had a huge grin, big dimples, great hair. He was the kind of guy who seemed stoned all the time, but I don’t think he actually was. The fact that he was able to look past my braces and stinky vomit breath and stick his tongue down my throat was a true gift, even if it did feel like there was a slug in my mouth and I had no idea what I was supposed to do. Aggressively kiss him back? Passively receive the kiss? I wasn’t sure. (To be fair, I’m still not sure I know how to kiss properly. I always wonder if I’m doing it right. Even though I’m an actress and kiss people in movies all the time, you can’t exactly ask, can you? And even though those are technically first kisses, I also think about the rush of a real first kiss and wish I could have that without all the teenage awkwardness.)

That night at the hotel was an evening of firsts: my first make-out session, my first finger bang, my first night in a king-size bed. I was in heaven. So much so that I couldn’t wait to write all about it in my diary: I made out and was penetrated! Life is grand!

The next morning, I went home first thing because I was scheduled to take my driver’s test. My parents—the sweet, supportive people they are—were raving about my performance in the play while all I could think was, I hope they don’t smell the vomit and cigarette smoke.

Somehow, I passed my driver’s test. It was a major twenty-four hours in my life. But the blissful high of making out and having a license was short-lived. A few days later, my mother found my diary. She read my recap of Kyle’s finger-banging and thought it meant I lost my virginity, and she was furious.

Here’s the thing about my mother … she wanted me to stay a virgin until I was married. She made that very clear. This always confused me, because my mom is not a religious person. If her views had been based on God or the Bible, I would have at least understood the root. But she was a steadfast feminist, so her message seemed complicated. I think it was instilled in her at an early age that, as a woman, your sexuality was a dangerous and powerful tool, which had to be used extremely carefully. It must have been complicated, because she and her sisters were, and are, unbelievably gorgeous women with incredible figures. Growing up, they were dirt-poor but were known as the local hotties, and each of them reacted very differently to the power that comes with being unbelievably attractive. And I’m not saying this just because she’s my mom. She’s really a knockout. I have these beautiful pictures of her framed in my kitchen, one taken when she was nineteen and the other when she was twenty-seven. At a far glance it looks like me, but when you get closer you see that she had everything that I don’t: a seventies’ Playboy Bunny look—soft hair, high cheekbones, full lips. She must have really struggled with the complicated power of feeling beautiful and the desire to be desired and the guilt she felt toward anything sexual at all.

“Anna, you just don’t know your own value,” my mother said after she read my diary. I didn’t get it. I was supposed to be an independent woman, but at the same time I wasn’t supposed to do what I wanted with my body? It didn’t make sense.

Needless to say, when my mom read about my night with Kyle, she was pissed—and I was, too. I was devastated that she would look at my private journal, and it was clear she didn’t even understand what she had read. I didn’t have sex that night, obviously, and it hurt me that my mom couldn’t tell that I was really quite protective of my body—something I thought she should understand just by knowing me. Let’s be honest, I could have had sex anytime I wanted, because I was a sixteen-year-old girl surrounded by sixteen-year-old boys, and sixteen-year-old boys just want to bone.

So I did what any teenager angry at her mother would do and threatened to move out. To Stephanie’s house, of course.

A word about Stephanie: We became friends through drama class. I was a D+ on the social level, but she was a solid B. Not superglamorous but very well-liked; she was in drama, though, and that hurt her A. Where I went to high school, doing drama was sort of social suicide. Stephanie had an International Harvester Scout, an old car that was, once upon a time, an alternative to a Jeep. Hers was white and blue, and we used to drive around Edmonds in that truck listening to New Order and it was awesome. She also had a lot of independence—her parents were kind of hands-off—so I thought it made perfect sense for me to take a break from my parents and move in with her after the diary fiasco. My mother said no (of course she did, she was a rational parent), but at the time I was completely horrified that she wouldn’t support the move in light of her betrayal.

Nothing else came of that kiss with Kyle. It was fun, and kind of gross, and we never hooked up again.

But that was okay, because Chad Burke came along soon after that.

On November 19, 1993, I told my parents I was headed to—surprise!—Stephanie’s house. It was my senior year, and I was about a month into dating Chad. He was friends with some guys who were in a fraternity at UW, so we drove to the campus to crash one of their parties. We were in the frat house, deep into our red Solo cups of jungle juice, and suddenly Chad grabbed my hands, looked into my eyes, and said: “Anna, I want you to lose your virginity to me.”

“Okay, Chad,” I said solemnly. “Me too.”

Chad couldn’t say he wanted us to lose our virginity together, because it was going to be his second time. He slept with another girl in our high school before he and I got together (I can’t remember her name, only that she looked like Ani DiFranco), but they were never in a relationship. I found his honesty about this romantic—my standards were always exceedingly high.

I told Chad I wanted to wait until after I turned seventeen. I don’t know why that age marker was important to me, but my birthday was ten days later, so I figured we wouldn’t have to wait much longer. After that, I told him, I wanted to do it.

The plan didn’t quite pan out. I turned seventeen on November 29, and a few days later, before Chad and I had the chance to have sex, I started hemorrhaging out of my vagina.

It started out as what my mom told me was my “first very heavy period.” I had to change my pad every thirty minutes and it seemed more intense than a period, but what did I know? I was only seventeen. As an early Christmas present, Chad took me to see Phantom of the Opera and I had to keep running to the bathroom and begging people for tampons because I’d used up all of mine. Eventually I bled through my dress and Chad took me home. My mom told me to take a bath and we watched as the tub filled up with blood. Later that night we went to the hospital, and I passed out in the waiting room.

It turned out I was having some crazy hemorrhaging where I lost about 50 percent of my blood in three days. I had a cyst on my right ovary—the particularly gnarly kind that has hair and teeth and is just incredibly gross. So I ended up staying in the hospital for about a week, which is, oddly enough, an incredibly happy memory for me, because I really hated high school.

The doctor I saw during that ordeal became my gynecologist, and at some point I had the opportunity to tell her that I really wanted to have sex with my boyfriend and that (1) my mom couldn’t know and (2) I could not get pregnant. So she put me on birth control, which she told my mother was to better regulate my cycle.

By January, I was a new, healthy woman—and a woman on birth control, no less.

Senior year we were allowed to leave school during lunchtime, and Chad’s parents both worked, so on January 7 I told him I wanted to lose my virginity during lunch. So that’s what we did. And it was horrible.

No, it wasn’t really horrible. It was a solid C. I certainly didn’t come, but nobody comes their first time. At that point in my life, I had never masturbated. I had never even explored, so I had no help to offer Chad in terms of getting me off. But I wasn’t really in it for the sexual pleasure. I was just head over heels for this guy, and at the time I thought if I was going to keep a man I had to give him my pussy over lunchtime at his parents’ house. In retrospect, his mother must have known. We were totally inconsiderate and never even thought about changing the sheets. Poor Mrs. Burke.

After we had sex, Chad and I went back to school and I felt the weird illogical pride of having lost my virginity. That afternoon I went to my neighbor Kate’s house—she went to a rival high school and was incredibly hot and popular and was the head of the dance team and had a great laugh and stunning smile and was funny and charming and had lost her virginity long before me—and her mom looked at me and said, “Something looks different about you. You lost your virginity.” I know that sounds like something Amy Poehler said in Mean Girls but she really did say that, and I loved the confirmation that I suddenly seemed more adult.

Of course, it took me many more years of sex before I felt any confidence or comfort when it came to doing it. If it hadn’t been for my massive insecurity about my body, I probably would have been incredibly promiscuous. I was totally intoxicated with the idea of feeling like a sexual being, and I wanted men to want me. But I was also completely ashamed of my body, especially my boobs (or lack thereof), and insecure about my abilities as a lover. I never felt like the hot girl, even though I so badly wanted to. I felt like I wasn’t good enough, and that I didn’t know what I was doing when it came to sex or going down on a guy. And when I did get intimate, I was so busy thinking about my own performance that I couldn’t appreciate the guy’s, and it’s really hard to have an orgasm when you can’t let that part of your brain go.

I’ve grown out of that, thank God, but it took me a long time to get there. Today, I love being intimate with a partner, but I have a lot of trouble being intimate with myself. For a while in my late teens, on the other hand, I was just the opposite. Freshman year of college, I went through a crazy masturbation phase. We had this college newspaper with an advice column and one time a reader wrote in and said, “My roommate masturbates all the time, what am I supposed to do about it?” I read it and thought, Oh man, she’s talking about me. To this day, I’m pretty sure I’m right about that, and that the letter was indeed about me. My roommate, Melissa, had a boyfriend who would call our room while she was at work and ask me about masturbating, so I’m convinced she said to him: “Oh God, I’m rooming with this gross girl, Anna, and she gets herself off all the time.”

Melissa didn’t like me very much. (Considering that last paragraph, maybe that’s not a huge surprise.) We had one of those communal shower situations in our dorm bathroom, and one time she came in and started throwing her shampoo and conditioner at me because she was mad that I didn’t wake her up for her exam. I was so confused (and still am!), because I didn’t know that was my responsibility.

I ended up leaving that dorm—not because of my excessive masturbation but because Melissa and I clearly didn’t get along—and I moved into a different dorm with a sweet roommate who at one point asked me why they call it a blow job.

“I don’t know,” I said. “Because you blow?”

That’s totally incorrect, of course. It’s actually because a guy blows his load in your mouth and not about us at all. Big surprise.

I got it out of my system, and I have an irrational fear that someone is watching me whenever I’m intimate with myself. I know that’s ridiculous, but it’s hard to shut off all the insanity that’s going on in my brain at any given time. I feel like getting myself off would force me to confront the things that terrify me about myself, and to face sexual desires I don’t even know I have. Masturbation acknowledges your sexuality in a way that we never did in my household, and while it was easy to get stoned in college and block out those childhood messages, as an adult I find it surprisingly difficult. Which perhaps is why I still feel an incredible amount of shame when it comes to self-pleasure. Once, when Chris was traveling for work, Allison Janney and I were talking on the set of Mom. “Chris is gone and I haven’t masturbated in four months,” I told her. “I don’t know what’s wrong with me. I think I probably should, but I can’t.”

Allison just looked at me and said, “Oh, honey, you’ve got to work on that.”

Needless to say, I’ve got a complicated relationship with masturbation. I think we can all agree that men don’t find themselves in that predicament.

For a lot of women, the four years of college are a time of sexual experimentation and, in some ways, I definitely wanted that experience for myself. I loved going to frat parties and flirting with boys, but then I would get wasted and run away as fast as I could. I felt like the definition of a cocktease.

There were definitely a few times when it got a little scary, most notably during my sophomore year. I was talking with a guy at a party when I told him I had to pee. He said I could use one of the bathrooms upstairs. In fact, he had a private one in his room! How convenient! He said he’d show me the way and went into the bathroom with me, locked the door behind him and started trying to make out with me. “This is not fucking happening,” I said. Maybe I didn’t use those exact words, but close, so he left and locked the door from the outside. I was stuck in the bathroom and could hear him in the hallway talking to his friends, saying something like, “I got this; it’s all good.” I turned into that mother who can suddenly lift a car when her baby is trapped underneath—I heard this guy with his friends and just thought, I am a warrior and I’m getting the fuck out of here. So I picked the lock—which was not especially hard, it’s not like I’m a champion lock picker—and I made my escape. These days, there’s a lot of talk about college sexual assault, but that conversation was not happening in 1995, it was just “you get drunk at a frat house and it’s up to you.” So I channeled my inner ninja and dealt with it.

I have had one one-night stand in my life. After Chad Burke, I dated a guy named Dave on and off for most of my college career. During one of the off periods, I had a drunk night with some guys who lived on the floor above me in my dorm. We were all drinking and laughing about something stupid in their room, and I saw one of the guys look over to his roommate and give him a head jerk that clearly said, “Time to leave, wingman.” You know when you’re wasted but then something happens that jolts you back to reality? That head nod did the trick. The roommate understood the signal and left, and the other guy and I started kissing. Suddenly he was on top of me, and I said no, and he stopped, groaning, “Oh fuuuuuuck,” mostly to himself, in a clearly frustrated tone. I didn’t want to annoy him or be a tease, so I gave in. I was pretty resigned and unsure, but I said okay. I gave consent. Still, it’s not a good memory. I was so disappointed in myself for conceding, and despite having spent plenty of time wishing I was more sexually daring, that wasn’t a great night.

It wasn’t all sexual nightmares, of course. There were good times, too, though the best of those came later. About a decade later, but they came.

Unqualified

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