Virginity Stories: At the Top of a Hill by Ginny Chesson

Editor Carrie Seitzinger, Editor's Choice, February 20th, 2017

"... like what sex is supposed to be. Giving in."

Ginny Chesson Essay Nailed Magazine


Virginity Stories,” a series within NAILED’s “Sex Stories” in which all kinds of people write about losing their virginity. To submit to this column, email Shenyah at

+ + +

The day I lose my virginity is the first day of the New Year and it’s warm. I’m wearing flip flops, the low rise skinny jeans from Forever 21 that the leader of my improv troupe said I look good in, and a thin grey sweater that shows off my stomach. It’s my senior year and I’m kind of thin—I haven’t been eating enough. Earlier I ran a bath and added salts to make it smell nice. I shaved my armpits and everything below the line where my underwear begins. Then I showered, washed my hair, and rinsed all of the pubes off of my body. When I got out of the shower I scooped them up with a piece of toilet paper and threw them into the trash. I dried off and covered every inch of myself in scented lotion. I put on my outfit and looked up the bus route to Doug’s apartment (73 to Harvard, from there catch the 38 towards Sullivan).

I’d been texting him all day, because I was nervous. I asked him what if I faint, and he said “lol” and “I’m not the Beatles.” I was not charmed. Yesterday, last night, he sent me pictures of himself “at a New Year’s party.” When I get to his apartment I’ll realize he’d taken the pictures at home. I’ll never mention it. He asked me to call him so that he could wish me a happy new year. I did it, awkwardly walking away from my friends who were holding sparklers and singing God Bless America so that he could tell me that my voice sounded different than it did when we skyped—deeper, “less submissive.” He said, “Happy New Year. I’ll see you tomorrow.” He sounded anxious.

Later, months later, he’ll tell me that he was so nervous the first time. He was afraid that the cops were gonna show up, that something bad was going to happen. He looked up the law and everything—the age of consent in Massachusetts is 16 for women, 18 for men. When I look it up I’ll find this:

“Whoever induces any person under 18 years of age of chaste life to have unlawful sexual intercourse shall be punished by imprisonment in the state prison for not more than three years or in a jail or house of correction for not more than two and one-half years or by a fine of not more than $1,000 or by both such fine and imprisonment.”

The two of us will argue about what “of chaste life” means. I’ll say it means that having sex with someone under 18 who is a virgin is illegal. He’ll say it’s the other way around. We’ll never clear it up.

I listen to The Killers as I take the 86 to Somerville. I get off a few stops too early and don’t know where I am, so I call him and tell him I’m lost. He laughs and teases me, then tells me he’ll pick me up. He says he’s driving a silver car. While I wait on the corner of Elm and Day, I do not wonder or think. I have already made my decision—this is what I want. No one is around, and even though it’s winter, and it’s late, the sky is light. Finally, a car passes, slows, and turns. When I round the corner it’s parked and he’s standing by it. He’s short, but I already knew that. He told me he liked that I was taller than him, made it hotter. The first thing he says is, hi. And then I get in his car. I don’t stop to think about it, I just open the door and get in. He gets in after me. Then he tells me that I’m beautiful, and I thank him.

“I mean, I knew you were gorgeous from your photos, but they really don’t do you justice.”

I thank him again and buckle my seatbelt.

He drives. He asks if I am nervous. I say yes. “Well, we’re not going to do anything tonight. Just get to know each other.” I stare straight out at the road, we’re going over a hilly bridge with chain link fence on either side of it. “You’re a vegetarian, right?” I say yes. He puts his hand on the back of my neck and I feel it everywhere in my body—dissolving my voice, screaming from my clit, my stomach and chest a collision of knives. I want it. It’s what I deserve. He keeps his hand there for a long time, putting on pressure, squeezing, letting me know that he’s there, that he has me, owns me.

His house is the first in a row of old boarding houses that have been converted into apartments. He lets me in and watches me climb the stairs to his floor.

The first time we don’t have sex. At least, not what people told me sex was then. Penis in vagina. He lights votive candles in iron holders on the walls, walls painted an awful Nickelodeon slime green. A while later when I ask about the color, he’ll tell me it’s called sea foam. I’ll be skeptical. Sea foam sounds soft and beautiful. The green on his walls is repulsive.

That first time we sit next to each other on his tiny, shitty couch, and watch Wet Hot American Summer. A sloping ceiling cuts off all the rooms in his apartment. His college diploma is hanging on the wall. When the movie ends, I am lying with my head in his lap and he’s stroking my hair. I can feel his stomach pushing against my head. I try to enjoy it, try to let it be comforting. I’ll tell my friends afterwards that I lost my virginity and it’ll feel like I’m lying, but it’ll also feel true. He turns off the TV and I sit up. He asks me if I’m still nervous. I say I am. He says, “try to relax, I just want to get to know you, we’re not going to do anything tonight. Just talk.” I say okay.

“So, what was one experience you learned from in 2011, and one you thought was cool?” I am confused by the question because it’s a stupid fucking question. I tell him about spending the summer in Panama. I’m not trying to impress him, I don’t really care what he thinks—other than that he wants to have sex with me, wants to hurt me. The conversation winds down. He asks me about being a virgin. I haven’t had sex because no one wants to have sex with me, because I am ugly and weird and talk too much. My first real kiss, real as in not a dare or part of spin the bottle, was four months ago while I was visiting my friend at Brandeis. I tell him about it and he is surprised. “You only had your first kiss four months ago?” I am embarrassed. “But you’re so beautiful, don’t the boys at your school like you?” I tell him that they are afraid of me, because I’m smart. He says “I can’t believe that.” And then he says he wants to kiss me now. I say okay, and sit there, waiting. He laughs quietly, then places his hand behind my neck and gently pulls my face towards his. He puts his tongue in my mouth—it is a big tongue. Wet. My mouth is dry. He tells me to stand up. I do it. He tells me to take off my shirt. I do it. It’s finally happening. It’s cold, I can feel my nipples under my bra. He stands and touches me on my waist and my entire being wrenches itself to the farthest corner of reality like I’ve seen girls do in movies when they want it but also don’t. Hips dragging towards, eyes and head yanking away. It’s sexy, like what sex is supposed to be. Giving in.

The morning after that first time, before I get out of his car to catch my bus, he tells me to text him as soon as I get home. He wants to make sure I’m safe. I say okay and am about to get out when he says, “Wait, don’t I get a kiss?” In my head I make a deal with myself. Just give him this one last thing and then I’ll never have to think about him again. I lean over and he kisses me, for too long and too wet, and then I get out of the car as fast as I can. He drives off and I feel the crushing enormity and safeness of the world and Harvard Square. When the bus comes I get on and think, “I did it. I got away with it.” I’m overjoyed, but maybe not for the reasons that I thought I would be, and something else, something that doesn’t make any sense so I won’t put a name to it until a few years later—hurt.

A month after the first time, the time that I slept in his bed because he said he’d love to wake up next to my beautiful face, I have been texting him again for a week. A day or two after I left his apartment I told him I didn’t want to talk to him or see him again. He said, “Okay, that’s up to you, but you’ll be back.” I waited a few weeks, until I felt lonely enough and horny enough, and then I texted him. He’d tell me things to do, like when we first started talking online and he made me go to school without a bra or underwear. It turned me on. Then, one morning in February, he asks to call me. I say okay and he starts giving me instructions over the phone. He tells me to take the clothespins I bought down the hill at the craft store, and put them on different parts of my body. I do it. It hurts and I like it, and also I don’t. He says that I’m his, that he owns me, that I belong to him. He tells me to say it and I can’t. I cry, I have a panic attack. He tells me it’s okay. I tell him I can’t see him again. He tells me it’s okay. He tells me it’s all up to me.

Another few weeks go by and I make plans to see him again. This time when he picks me up from the bus depot in Sullivan Square it’s spring and the sun is just setting behind the black, leafless trees and the old brick factories. There is a large yellow clock with iron hands. He makes me put on a red collar. He tells me to, and I do it, because I want to. Because it turns me on to be treated like I deserve to be treated. Like a dog.

His penis makes me think of a slug. It’s short, and thin, and he can’t maintain an erection and he can’t finish. He is balding. He is growing a beer belly. I am repulsed by the way that he looks, by the things that he does, and by the fact that he is having sex with a seventeen-year-old. But I keep going back.


Two years after the first time I meet Doug I make plans to play with him and his girlfriend Kim, who is 26, over spring break. I tell him about my new rules—he’s not allowed to kiss me, he can’t comment on my hairy legs or armpits, and he has to keep his dick in his pants. He agrees. I put on a tight black dress and drive to Somerville in my mom’s car. When he comes out of Kim’s house I give him a hug and notice how tall I am. He asks me how things are and I tease him. Nothing about him scares me anymore, but BDSM is fun for me even when the line between reality and play is clear. He reminds me that as soon as I walk through the door of her house I have to be submissive. I say, “I know, I know,” and walk in. He follows me up the stairs—he’s looking at my ass.

When we reach her floor he points to an open door and tells me to go look. The room is dark but I can make out Kim’s shape, a little blonde x strapped to a bare mattress with a ball gag in her mouth. I remember when Doug told me that there would always be a part of me, no matter where I went or who I fell in love with, that belonged to him. He makes me kiss her, telling me where to go. I feel her body with my lips—hard nipples against her flat chest, the slow, gentle softness of her stomach and thighs, her small, beautiful hipbones. As I eat her out I try to transmit a message from my tongue to her brain: you are good, you are powerful, you are loved.

Afterwards, they ask me to stay and cuddle and talk about things. I say no thanks and goodbye. By the time I get in my mom’s car and pull out of Kim’s driveway I’m shivering. I want to drive, so I go to Arlington, to Skyline Park, where me and my friend Janey used to race each other down the giant red slides. From there the view of Boston is the best—the stars, the lights of the buildings and the bridge, somewhere out there the MFA and the Museum of Science, all of Somerville and Harvard Square, and the river that used to be dirty but now is clean. At the top of the hill I sit and watch the city and yell along to Temecula Sunrise, shaking with joy at the terror of owning myself.

+ + +

Header image courtesy of Ángela Burón. To view her photo essay, “Static Minds,” go here.

Ginny Chesson Essay Nailed MagazineGinny Chesson is a performer and writer living in Chicago. Her work focuses on sex, gender, death, class, and the overwhelming absurdity of existence. Contact her at







Carrie Seitzinger

Carrie Seitzinger is Editor-in-Cheif and Co-Publisher of NAILED. She is the author of the book, Fall Ill Medicine, which was named a 2013 Finalist for the Oregon Book Award. Seitzinger is also Co-Publisher of Small Doggies Press.
Learn more about her at her official site.