Young First Time Sex Stories

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Young First Time Sex Stories

Secret Solitary
By Thomas Bartlett Whitaker


Ketamine
By Bria Adimora Godley


from Beyond the Somber Station
By Liliana Ponce, translated by Michael Martin Shea


rising to the earth’s height
By Raquel Salas Rivera, translated from the Spanish by Carla Canseco

© 2004-2022 Guernica . All Rights Reserved.
Photograph via Flickr by Michele Molinari
My mother stands ironing in the kitchen. There is barely room to squeeze between the kitchen counter and her bottom. I am about twelve; she is five foot two. It would be unnatural to turn to face the cupboards as I slip past. I am wearing loose-fitting pants. She is in a skirt. As I brushed quickly by she bends to iron and presses her bottom against me. My penis swells with joy. I will remember this for many years to come, in unexpected situations, soothing, erotic, violent, or clumsy.
It also reminded me of an earlier time, in third grade, when Tawny Collie—that was really her name—the sexiest girl at Elbow Elementary bent over to pick up a red rubber ball during recess and a couple of my friends pushed me onto her behind and she turned around and said, “Clancy, that’s not nice!” I protested, and my friends laughed. In first grade Tawny had had a crush on me and had invited me over to her house at lunch for fish sticks, which I couldn’t eat. But by third grade I was well established as one of the unpopular kids, and flying below everyone’s sexual radar. Still, or for that reason, Tawny should have known better.
The first time I successfully masturbated I was eleven and my older brother and his girlfriend were watching Woody Allen’s Everything You Always Wanted to Know About Sex* (*But Were Afraid to Ask) .
Last night our little brother, as my stepsister Teryn told the story the following morning, had come downstairs while the rest of us were out and Teryn was alone watching television in the family room and asked her to “pull on my thing.” The thing was on full display, Teryn claims, out of the pajamas. “It was hard and he was rubbing it.” The little brother was age nine or ten. It is widely known or at least agreed in my family that Teryn is a liar and will lie in particular about this little brother, because she was the baby until we arrived, and then he became the baby, and my mother has never liked Teryn, and often accused her of sexual deviance and promiscuity from a surprisingly young age. So there’s no guessing whether or not the story Teryn tells me is true, though later in life my mother will similarly tell me that she saw the same little brother (now age sixteen) out mowing the lawn with his shirt off in the low, modest Calgary summer sun and pronounced fiery claw marks down his back. Why my mother told me this story also remains mysterious to me, though she once told me that “he got the looks, he could have been a model,” and another time she told me how much he resembled my father, who had no appeal for my mother other than as a sex object. He was a terrible husband, my dad. But the old man had gigantic sexual charisma. I’d seen him, in years past and in many different cities, pick up waitresses right there in the restaurant, before we’d even paid the check.
The first time I successfully masturbated I was eleven and my older brother and his girlfriend were watching Woody Allen’s Everything You Always Wanted to Know About Sex* (*But Were Afraid to Ask) . The process was slow and often seemed hopeless: I think it took an hour or more. I could still hear the movie in the background. I imagined my penis as a straw and a girl from school sucking on the straw. When I orgasmed it was qualitatively different than any orgasm I have had since. They say that, the first time you smoke heroin, it is called “riding the dragon,” and after that you are always only approximating that birth into a new world of pleasure and disappointment.
You can French kiss yourself. Take your tongue, fold it back upon itself, and now roll the tip of your tongue back and forth across the middle of the muscle. I learned this after French kissing Denise at the seventh grade dance. We had those at Rideau Junior High: every five or six dances the teachers would play a slow song, turn the lights down low, and we would have a kiss dance, during which, with luck, you would French kiss the entire time. I passed Denise’s house wearing my canvas bag of rolled and rubber-banded Calgary Heralds and tossed one on her porch, while French kissing myself. It is mildly titillating, but seems filthier, somehow, than masturbation.
In graduate school I decided to become gay. Many of my heroes were gay: I had thought Franz Kafka was gay, for example, though it turns out he probably was not.
Age five and I am inspecting statues of nudes in a large museum book my parents keep in my stepfather’s study. The book is fascinating and I take it back to my bedroom and climb on the top bunk—my bunk—to look at the pictures more closely. The fact that the most interesting statues—the ones with breasts—have no penises puzzles me. In the bathroom I stand naked on the toilet so that I can see myself in the mirror and tuck my penis and balls between my legs and press my legs tightly together to achieve the desired effect. Ah yes, that must be what is happening in those pictures, I conclude. Then my mother enters the bathroom—there are two doors into it, one from the hallway and the other from my parent’s bedroom, and I’ve forgotten to lock their door—and begins to shriek. “Never do that again! That’s very bad!” Etc. To be fair to my mother, she has always been hysterical and repressed on the subject of sex (I don’t particularly like the topic either), and my father claimed that this was a main cause of their divorce. It’s true that she avoided physical contact with us for years. She had been abused as a child, though I don’t know in what fashion. On her wedding night there were some problems in bed with my father, and he left their hotel room, returned a few hours later, and threw a pair of woman’s panties at her.
After my mother married my stepfather there are some sexual experiences between age five and age fifteen that I do not recall well and may be inventing that took place between myself and one or more of my angry older stepbrothers behind the furnace in our basement. I was terrified of that small black hot space.
In graduate school I decided to become gay. Many of my heroes were gay: I had thought Franz Kafka was gay, for example, though it turns out he probably was not; Kierkegaard might have been gay; it is possible that Friedrich Nietzsche’s first sexual experience was with a man, a kind of wandering prophet, a forester who walked with a stick and professed to be a wise man, and preyed on school boys; Oscar Wilde was gay; Marcel Proust was gay (I’m told that stuff about the rats and the hookers is invented); Jean Genet was gay; Burroughs was gay (William—Augusten is too, but, capable writer though he is, he’s not a hero of mine, and anyway hadn’t made the scene yet when I was in graduate school, or who knows, perhaps he might have been, I was in the hero-forming business in those days); was Levinas gay?; Plato was gay. My best friend at the time, Robert Ramirez, was gay, and wanted me to be gay too. (Now he is dead.) We danced at a gay bar and while I was dancing with a girlfriend of his, a hanger-on, he came to us on the dance floor under the many-colored lights, the celestial immodesty and grandeur of the sweaty, loud gay bar, and the three of us danced with the girl in the middle, and Robert and I kissed. Nothing. All my modest attempts were useless. Later that night the girl and I had sex—she was a virgin—and Robert’s feelings were hurt that we didn’t ask him to join us. First he passed out and then he stormed out. I never spoke with the girl again. I abandoned the idea of being gay. William Butler Yeats was not gay.
SD and I were in the basement in her bedroom. She was encouraging me to rub my erect penis on the crotch of her black panty hose. She was a natural redhead. When she took off her clothes her slightly fat body shone with the strength of a flashbulb in my eyes. She rolled on her belly, moaned, and lifted her ass in the air. “In my ass,” she said. I had anal sex before I ever had vaginal sex: that was how I lost my virginity, that winter afternoon in SD’s ass.
Clancy Martin ’s writing has appeared in Harper’s , NOON , McSweeney’s , The London Review of Books , the New York Times , and other places. Author of the novel How to Sell (FSG), he teaches philosophy at the University of Missouri in Kansas City.


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"Afterwards, I expected to feel more mature and more confident, but I really just felt the same as I always have."
Thanks to thee unrealistic standards constantly portrayed in media , we've all built up this imaginary idea of what sex is supposed to be like. Some people expect a romantic night of candles and passion, while others think it will be the most pleasure they've ever felt in their whole life . But the truth is, everyone's experience is different. Sometimes it's smooth and romantic and lives up to your expectations, while other times, it's kind of terrible.
But no matter how old you are or what the circumstances are, having sex for the first time can feel like a huge deal! So, to give you a better idea about what your first time may be like, we talked to 43 girls about the first time they had sex — how they knew they were ready, who they did it with, and how they felt afterward.
1. "He knew I was a virgin and for some reason, I had this expectation of it being magical, which in all honesty, it wasn't. He kept his face buried in my shoulder/neck the whole time and asked if I was okay once during, which I thought was kind of inconsiderate. I think I would have enjoyed it more if he had checked in with me to see if my needs were being met, which they weren't . At the time, I was blinded by my love, so I chose to look past that." — Hafeezah, 22
2. "It was not romantic at all. It was messy, drunk and horny. I was 17, drunk at a beach concert, called a guy that we had an on and off thing and we had sex in the back of his pickup car. Then, he went to study abroad and we never spoke about it , until like 2 years later." — Bianca, 23
3. "I was a sophomore in high school and at a Halloween party. I got pretty drunk and had sex with one of my childhood friends (on his birthday) in the basement of his house. Then, the next day, I found out one of my best friends also had sex for the first time that night . So to this day, she and I will text each other on October 30 to say happy anniversary." — Tory, 24
4. "We were 17 and we needed a time when our parents weren’t home, so we waited until Christmas Eve when his parents had left for a holiday party. I was so incredibly nervous — I think we both were. So we lit candles and took it slow . To be honest it hurt like hell. But other than that I think it was pretty perfect as far as virgins go." — Debby, 22
5. "It was after homecoming and we were just in his room. It all happened pretty naturally. It wasn't painful, but it honestly didn't feel like anything at all was happening . And then 1-2 minutes later it was over." — Jasmyne, 21
6. "I was 17 when I first had sex. I lost my virginity to someone I actually cared about, which doesn’t mean much to me looking back now, but it was important to me back then. It was late at night and we were in the backseat of his car . I was really nervous, but he was patient and managed to make me feel comfortable and sexy, even. I don’t regret anything and for that I’m thankful." — Jennifer, 22
7. "It was nothing like I imagined. I felt comfortable, but out of nowhere, I got really nervous . He told me to relax and that we didn't have to continue if I didn't want to, but I did. It was very painful to the point that I had to stop because I was in so much pain. I felt a little ashamed and embarrassed because I imaged something different and I thought he was disappointed in the experience. He was so understanding and he said it was fine and that he wanted me to be okay, and that we didn't have to continue. He made me feel better about the experience, and we are still together two and a half years later." — Katie, 24
8. "I wasn't "in love" or whatever, but I guess I never expected to be. He made me feel comfortable and respected, so one night, I went over and we had sex. It wasn't awkward or weird, and it wasn't this special magical moment either . We went to a diner the next morning for breakfast and texted my best friend group chat the link to Lonely's Island's "I Just Had Sex," and I think they were more excited about it than me to be honest." — Tiffany, 21
9. "Truthfully, it wasn't enjoyable. I wasn't ready at all and he was . And then it sort of just happened to me rather than me choosing whether or not I wanted to." — Alex, 22
10. "I was on senior week, and I was hanging out with the boy I liked. His friend was asleep in his hotel room, so we did it on the balcony . It was completely unplanned, but I've never regretted it. I'm still friends with the guy, too." — Kelsey, 23
11. "It was the summer after high school for me, sort of an in the heat of the moment type of situation with this guy I'd been talking to for a while. Surprisingly, it wasn't uncomfortable . It didn't hurt or anything like I'd expected, which was interesting!" — Anumeha, 21
12. "My first time was with my boyfriend of a few months. I was 19. After class, I hung out with my boyfriend at his house (he lives with his parents). Later, I snuck back in after his parents fell asleep. It was super unexpected and definitely not planned. I know that I was ready to have sex, but the nervousness of being COMPLETELY NUDE in front of my boyfriend for the first time PLUS being in his house when I wasn't supposed to be made it hard for me to let myself really feel good. I didn't necessarily feel bad, and I definitely don't regret any of it, the circumstances just made it hard for me to let go and loosen up. Thinking back to it eight months and many sexy times later, I honestly wouldn't change anything. I've grown so much more comfortable with sex, and I can thank my boyfriend for that for being kind and gentle." — Maggie, 19
13. "My mom tried to have an open and honest conversation about having sex so that I would feel less nervous when the time came. But the conversation was always about boys, never about being sexual with girls , so I felt completely unprepared when I went to have sex with my girlfriend for the first time." — Brooklyn, 22
14. "I was 18 and I kinda just wanted to get it over with. It was the summer after I graduated from high school and I was on a date with this kid I knew since elementary school. We had talked about it before and we got this cheap motel and we did it. I felt kinda numb until the next morning, when I got in the shower and cried for an hour." — Ari, 21
15. "I lost my virginity at 14. It wasn't a big deal in my mind, as I'd lose it one day anyway, so why not then? I was talking to the boy for awhile and he made me feel like it was the right thing to do. I imagined it'd be like in the movies — all sweet and romantic, all planned out. It wasn't! It was awkward and I didn't really know what to do. Since then, my experiences have gotten better as I now know what I'm doing." — Jenna, 17
16. "I was 17 and my best friend was a 21-year-old guy. We always joked about marriage, and he was cute, but I never felt attracted to him. One day, we went hiking, and he kissed me at the top of the peak, and I felt excited. He was older, his arms were strong, and he wasn't aggressive like the boys I kissed in my grade. He was my best friend and we were kissing — what!!! Anyway, that summer, we talked about having sex, but he insisted that I had to be 18. Finally, my birthday came, and his family was home, so we snuck into his backyard and went into a children's playhouse adorned with little kitchenware and dolls. So not sexy. It was awkward and it didn't really work. He blamed me for it. It was really immature. Also, after having sex with guys, I've realized that sex with girls is more my speed — more fun." — Naomi, 21
17. "I was 16 years old and it was right after I went on a hike with my boyfriend. I had always been nervous about the idea of sex. I had so many questions about how it would feel. But we discussed it and we both agreed we trusted each other fully. At first, it felt weird — not painful, but just a completely different feeling. My advice is to make sure you trust this person so you can enjoy it even if it is awkward at first." — Carina, 19
18. "I wanted to have sex before college because I didn't want my first time to be a one-night stand after a party. I had met this guy online when I was younger and we had been talking for awhile. I had gone to see him a couple times and he said he didn't want to be my first. But then on New Year's Eve, he invited me over and we ended up having sex. I felt super weird after, because I was like, maybe I should've waited for someone I loved. I really think that shapes how I treat sex now. I know a lot of people whose first time was with someone they loved, and now sex is this sacred thing for them — whereas for me, sex is really just an act of pleasure." — Phoebe, 23
19. "I was 18 and in a long-distance relationship. My boyfriend was visiting and it felt right at the time. But then he had to leave to go back to school, and I was left with a lot of emotions, including regret and shame. I missed him and I felt overwhelmed. Even though we aren't dating anymore, I really did love him and a part of me always will." — Sammy, 18
20. "I was 16. My boyfriend at the time and I had been together for about eight months and things were getting serious, so we decided to do it. I was expecting it to be so nice and amazing, but instead it was so painful. It only lasted a couple of seconds. " — Katelyn, 20
21. "I had been dating a guy for less than a month when he told me, 'We need to have sex so we can figure out if we have a spark to continue dating.' I was 18 and wanted to lose my virginity so I could fit in, but also because I really liked this guy. We had sex in a car (how romantic, right?). I was so nervous that he wouldn't feel that 'spark,' but he did. At the time, I felt amazing. I thought I found the guy of my dreams and that we'd get married. We're no longer together, but I don't regret the experience. I just wished I had known I didn't need to have sex with a guy for him to approve of me or continue dating me. " — Mikayla, 20
22. "I love my boyfriend and I was ready, so we had sex. I'm on the Pill and we used condoms. It didn't hurt at all. I was so happy to be making love with him. I liked the feeling of being so close to him
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