People Share True Stories Of Love-&-Sex Firsts

Illustrated By Anna Sudit.
From first kiss to first sex (however you define it) to first orgasm, what importance do you assign your sexual firsts? Perhaps some were wonderful, and others were nonconsensual or otherwise awful. Some of these are likely pivotal moments, while others may be forgotten. (Contrary to what teen movies teach us, firsts aren't always a big deal.)
To honor the huge diversity of first-time sexual experiences, we're gathering your retellings of them and compiling your stories each month with a new theme. First up: First kisses. The accounts that follow range from charming to creepy, and they may have you looking back on your own sexual firsts. No, they don't predict our future sex lives. They often do shape us, though — or at least provide us with stories to tell.
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1 of 33
Identifies as: Female
Age: 17
Age at first oral and penetrative sex experience: Not listed

"The first time I had oral and penetrative sex happened on the same night. I had finally met my long-distance boyfriend of over three years, and neither of us could wait. It was really romantic and sweet and exciting. I'm glad I got to explore the body of someone I really loved at the time, and it was amazing to share that experience with him."
2 of 33
Identifies as: Female
Age: 25
Age at first oral sex experience: 14

“When I was 14 — I performed oral sex on an older boy that I had a huge crush on at the time. He was a sophomore in high school and I was an eighth-grader. We never dated or anything like that, and I went on to lose my virginity when I was 19 to my first boyfriend (in college). I've never regretted that night in the car, though — it was exciting, and I did it because I wanted to.”
3 of 33
Identifies as: Female
Age: 22
Age at first oral sex experience: Not listed

“The first time I gave my high school boyfriend a blowjob, I had never seen a penis up close before. It was very relaxed, just kind of me-exploring-down-there type of situation — no expectation of ‘blowing his mind’ or anything — BUT I was so fascinated by his erection that I couldn't stop staring, and then he got self-conscious and went flaccid. He hid his junk under the blanket for the rest of the night, and kept on asking me how I'd feel if someone scrutinized my vagina during oral sex. (Spoiler alert: frankly, could not care less.)”
4 of 33
Identifies as: Female
Age: 22
Age at first oral sex experience: 18

“It was my first week of college, and I had been flirting with a junior for a few days. We started kissing at a party, and he invited me back to his dorm room. He was totally nice, and we were having fun. I was also very excited about the fact that I was hooking up with a junior! He was in his 20s! However, as soon as I suggested that he take his pants off, I freaked out. I gave him head for five seconds and then suddenly had an important friend emergency that I needed to attend to.”
5 of 33
Identifies as: Female
Age: 24
Age at first penetrative sex experience: 17

“My first penetrative sex experience was entirely uneventful. We were not in love, and I was 17, and I don't remember having any particularly passionate feelings about the boy or the idea of losing my virginity. Either way, he fingered me so hard (and painfully) before we ever had real sex that when we finally got around to it, it felt like nothing. At that point, I had subzero understanding of what sex was supposed to feel like or that what it felt like to be sexually pleased. I also did not see myself as a sexual being or sexy person at this point — or, honestly, until about my 12th partner, so...there's that.”
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6 of 33
Identifies as: Female
Age: 27
Age at first penetrative sex experience: 18

“It was freshman year of college. I really wanted to get sex out of the way and wasn't interested in being overly sentimental about it. (Oh, how things change.) So, I invited a guy I'd met at a party back to my dorm, and we had penetrative sex. It was very quick, and I don't think either of us orgasmed. The real thing I remember is waking up the next morning (he didn't stay) with my sheets soaked in blood. I charged into my suite-mate's room and started frantically quizzing her about whether one should use cold or hot water to remove bloodstains.

“One other funny thing: This guy and I ended up matching on Tinder five or six years later, at which point we had a whole conversation about the experience. I'm not sure whether he knew it was my first time, but he admitted that he had no idea how to handle the experience, which is why the whole thing never went anywhere. All's well that ends well, though.”
7 of 33
Identifies as: Female
Age: 26
Age at first penetrative sex experience: 17

“It was on my 17th birthday, with my first high school boyfriend, Nick. We'd only been dating for about a month, but I was so into him, and I'd waited until I was in a relationship before losing my virginity. So, the day of my birthday, he took me to dinner, and then we went back to his place. His parents were out to dinner, and his siblings were in the basement, so we locked ourselves in his bedroom and got to it. I remember he put on some shitty rap music to set the mood. Nick knew I was a virgin, so we went really slowly. And while it didn't hurt as badly as I thought it would, it was definitely — kind of more burning than anything. But holy shit did I bleed after — for a couple of hours actually. And I continued to bleed the next few times until we discovered the joy of lubricant. If I could do it over again, I'd tell 17-year-old Maria to pick up some Astroglide ahead of her first time.”
8 of 33
Identifies as: Female
Age: 27
Age at first penetrative sex experience: 17

“We were both 17, and it was so awkward — but sweet. I was visiting his house, and his mom was at work and after a VERY long make-out session, I told him that I wanted to go all the way. In retrospect, we had definitely overshot the moment, and he was, to put it bluntly, too soft at that point. So it only kind of half-happened. He made me swear I'd never say that was our first time, and later that evening, we actually did the deed. We only dated for about a month after that (going off to college, growing up, etc.), but I am, to this day, so grateful that I got to bumble through all that 'first time' stuff with someone who was as clueless (and game!) as I was.”
9 of 33
Identifies as: Female
Age: 30
Age at first penetrative sex experience: Not listed

“I said yes, but then froze, and silent tears formed. He eventually stopped, I got up went to the bathroom, saw that I was bleeding, made up an excuse to leave, got in my car, and cried the whole way home.”
10 of 33
Identifies as: Female
Age: 25
Age at first penetrative sex experience: 17

“I lost my virginity to my best friend's step-brother on the last night of summer before my senior year of high school. He was a year younger than me, and we had sex in the room next to their parents' room, while they were sleeping (monkey-covering-eyes emoji). My best friend is a trooper that she doesn't care, and he's a gem for playing it cool whenever I come to their family parties.”
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11 of 33
Identifies as: Female
Age: 29
Age at first penetrative sex experience: 17

“First penetrative-sex experience was the summer before my freshman year in college. I was dating this really cool, gorgeous guy a year older than me who lived one town over. I told him I was a virgin and wanted to wait. About a month into our 'relationship' (if you could call it that), my parents were out of town, and he came over to fool around after we went out one night. I decided I felt ready to go for it and told him that. He was happy but very surprised, and told me he didn't have a condom. I was SO determined to lose my virginity that night that I snuck into my (younger) brother's room when he was sleeping and started rifling through his drawers. He woke up and asked me what I was doing. 'Do you have a condom?' I asked. 'You're disgusting!' was his reply, before falling back asleep. I made my guy drive to a gas station to get them while I waited in my bedroom. He came back and we did it. It didn't work as intended, and I remember going to bed upset, with two or three used-but-not-really condoms in my trash bin. I woke up really horny and we successfully had sex — without a condom, because he had used them all. He left, and I called my BFF to share the news...and asked her to take me to Planned Parenthood for the morning-after pill.”

Ed note: The CDC recommends using condoms to reduce the risk of STI transmission, as well as unplanned pregnancy. Learn more about condoms and the types available here.
12 of 33
Identifies as: Female
Age: 24
Age at first oral sex experience: 16

“My high school boyfriend and I bought condoms at Kroger (classic Midwestern grocery store), then did it on the floor of his basement. So romantic. I was 16 and he was 17, we were both virgins, and neither of us had any idea what we were doing — I preferred it that way — but it definitely wasn't pleasant. It hurt, and I could barely walk after. When I drove home after, I was convinced my parents would smell it on me or something. ”
13 of 33
Identifies as: Female
Age: 30
Age at first penetrative sex experience: 17

“I was 17 and in a ‘serious relationship’ with my boyfriend, who was 16. I'd decided I was ready to have sex, and asked my mom to help me get on the Pill. About a month later, my parents were out of town and I decided it was time. I think my boyfriend, who was also a virgin, was mostly ready, but wasn't quite as raring to go as I was — but he went along with it. I don't remember much about the act itself, but I do remember getting very emotional afterwards and crying in the bathroom. I'm not exactly sure why it went down that way — I basically wasn't exactly as ready as I thought, and it didn't feel as incredible or life-changing as I was building it up to be. My boyfriend and I actually went on to have a pretty great, healthy sex life after that, though!”
14 of 33
Identifies as: Female
Age: 26
Age at first penetrative sex experience: 13

“I lost my virginity at 13, on a Friday night during a high school football game (I was in eighth grade; he was a freshman) across from the stadium in a random yard on the ground. It was so gross and super painful, with lots of blood that was on my legs and his hands and shirt when we walked back into the light of the stadium. I tell it like a funny story now, and I'm not traumatized by it, but if I step back and look at it from an outsider's perspective, or my mother's, it's really sad. I didn't care about the guy at all, but I had known him for a long time. I sort of wish it was a nicer experience, but on the other hand, it was painful and messy and I'm glad I just got it over with and have had plenty of amazing sex since.”
15 of 33
Identifies as: Male
Age: 40s
Age at first penetrative sex experience: Not listed

“I had never masturbated prior to having sex for the first time. Candy! That was my first thought when I came. It was the only thing I could compare the experience to.”
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16 of 33
Identifies as: Female
Age: 25
Age at first kiss: 16

"I was on vacation with my best friend and her family. We — my best friend, her older sister, her older sister's best friend, and I — snuck some alcohol from her parents and drank at the house. The night before, we had met four boys, all about our age, and they had invited us to hang out."

"There was a nearby house that didn't have renters for the week and was easily accessible if you fiddled with the gate to the backyard, so we decided to 'pool hop.' All eight of us went swimming in the house's pool, and I eventually moved up to the hot tub with one of the older guys, Andrew. Andrew and I made out in the hot tub until my best friend's dad caught us, shined a flashlight on our guilty faces, and dragged us back home."
17 of 33
Identifies as: Female
Age: 25
Age at first kiss: 12

"It was with my first 'boyfriend,' whom I dated for a couple weeks...we were serious. He was 14, I was 12. We met at our local community pool and, one day, he brought me behind the basketball courts to this wooded area."

"I wanted to kiss him, but once we did, I did not enjoy it at all and immediately regretted my decision. He forced his tongue down my throat and between trying to breathe and not fall over because of how aggressive he was being, I told him to stop. I then thought, 'Maybe this is just what kissing is,' so we continued. He started moving his hands up my shirt and I then knew for sure I wanted him to stop. He broke up with me on the spot because I wouldn't let him touch my boobs. If I only knew then how common this type of guy would be out in the grown-up world..."
18 of 33
Identifies as: Female
Age: 28
Age at first kiss: 17

"After a long and arduous struggle with my Catholicism, I had finally accepted that I was a lesbian at age 16 (I now identify as queer). Over the next year or so, I was discovering heart-rending crushes for the very first time. I didn't have that normal boy or girl crush thing as a little kid, so I was completely awash with all these emotions and fears — exacerbated, of course, by all my internalized homophobia and recently lost religion. (I'd like to give a shout-out to my therapist for dealing with that.)"

"One day, as a high school junior, I was struck like lightning by this girl in my theater class. She delicately played a few bars of "Moonlight Sonata," and I drifted over to watch her play, mesmerized. With that, I was completely overtaken with a crush that would last for several agonizing months. She was dating an obnoxious red-headed guy named Peter (upon learning my sexual orientation, he proceeded to shout about it to our whole science class, opening me up to a lot of borderline dangerous harassment that lasted for the remainder of the year)."

"Joke was on him, though. At a school dance in spring, I managed to snatch my crush away from Peter for some awkward 'platonic' dancing. During a chaotic moment, she grabbed my arm and pulled me under the bleachers and we proceeded to make out rather clumsily until Peter found us and ruined the whole evening with his ranting. We dated for five years. Peter is now in jail."
19 of 33
Identifies as: Female
Age: 22
Age at first kiss: 15

"My first kiss was 50% awkward, 10% holy, and 40% rainy. It happened one day after school with the guy who would then become my first and only boyfriend in high school (we lasted until the end of high school, about three years)."

"I used to go to a Catholic school where we weren't allowed to PDA at ALL. One day after school, we ran through the rain towards the corner of the school church, and when I turned to hug him, he kissed me. Concerned parents who were picking up their kids started honking their horns at us, so we had to scurry away. It's pretty gag-worthy — too much Notebook, not enough rock-'n'-roll!"
20 of 33
Identifies as: Female
Age: 26
Age at first kiss: 13

"I was dropped off by my mom at the movie theater to go on my second date with my first real boyfriend. Yes, we were boyfriend and girlfriend before date two. I was so nervous because we hadn't kissed yet, and I had never had a real make-out session before. He was a year older, and had already had a few girlfriends, so I totally figured he knew what he was doing."

"We sat in the farthest row in the back corner of the theater, and then it happened. We started making out — full tongue-on-tongue. It was so wet and sloppy, I couldn't understand why people liked kissing so much. We did not last long, but ended up making out again in college. Needless to say, [that time it was] a much better kiss."
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21 of 33
Identifies as: Male
Age: 32
Age at first penetrative sex experience: Not listed

“I am a gay male. But it was with a female, as I was very in denial about my sexuality. When I couldn't adequately perform, I was left with a whirlwind of questions in my head. Net/net it was a mess!”
22 of 33
Identifies as: Female
Age: 22
Age the first time she said "I love you": 21

"I said it to my girlfriend at the time, and I said it first. We were lying in bed and laughing, and we had been dating for a month, and I knew I felt it, so I said it. I was the first to say it, and she reciprocated with the same enthusiasm. I still look back on that moment and think of how perfect it was. I could never regret it because it was true and I meant it when I said it."
23 of 33
Identifies as: Female
Age: 22
Age the first time she said "I love you": 18

"I said it first to my then- (and current) boyfriend. It was kind of the elephant in the room; we'd been together for a while, and I just knew that we both felt the same. I actually was leaving to study abroad the next weekend, so I felt like it was now or never. Thankfully, he said it right back to me, but the next day was pretty weird. We didn't say it again for a while, and later in the day, he asked if I'd actually meant it the night before — awkward. Looking back on it now, it's still a great memory, and I'm glad it wasn't an over-the-top gesture. Just a simple moment between the two of us."
24 of 33
Identifies as: Female
Age: 22
Age the first time she said "I love you": 18

"I had been dating the same guy for a year, and I constantly wanted to tell him how much I loved him, but always chickened out. One day, he and I were lying on our backs in his room, listening to Arcade Fire's record, Funeral. The song 'Wake Up' was playing, and when the song really picked up, with all of the 'ohhh's, I decided to turn over and tell him that I loved him. He didn't have the reaction I hoped for. He almost sounded offended and went, 'Why?' I felt really uncomfortable and wanted to cry as the song finished out. We eventually started both saying 'I love you,' and said it a lot for the next year, but eventually broke up. Thankfully."
25 of 33
Identifies as: Female
Age: 23
Age the first time she said "I love you": 18

"I was snuggling in bed with my boyfriend. We had had the best day together, and I had been wanting to tell him I loved him, but I was worried it was 'too soon' and didn't want to freak him out — but I felt like I was going to explode if I didn't say something. Literally as I was thinking all of this, he turned to me and said, 'I don't want to freak you out — but I love you.' And I could barely get the 'I love you, too!' out fast enough. I felt so relieved and happy and excited in the moment, my face actually hurt from smiling so hard. And looking back on the moment now, I'm sitting here almost with the same stupid smile on my face."
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26 of 33
Identifies as: Female
Age: 25
Age the first time she said "I love you": 19

"One summer, I traveled to Edinburgh with my best friend — whom I had had a crush on for years — and a friend of hers. We ended up having the craziest, wildest, and best 10 days ever. We slept during the day, went out at night, and met people from all over the world — going to concerts, drinking everything we put our hands on, smoking pot in parks, looking at the sunrise from the roof of our hotel every day. We even got matching tattoos, for no real reason. Crazy.

"One night, I kissed my best friend. The next day, we made out on every corner of every place we went to, hiding from her friend... That night, in the middle of a very intense make-out session, influenced by the excitement of that moment, lust, and alcohol, I said, 'I love you.' We continued making out, and we ended up having sex that night, and every night that followed. I felt alive and honest.

"Everything was perfect: The music was perfect, the whole ambiance was perfect, our connection was perfect. After that trip ended, we decided that 'what happens in Edinburgh stays in Edinburgh'...but we ended up dating for about six months and completely ruined our friendship. We don't talk anymore, but in looking back, I wouldn't change anything — and I'm glad I said 'I love you.'"
27 of 33
Identifies as: Female
Age: 23
Age the first time she said "I love you": 16

"I was in a car with my boyfriend at the time. I was telling him about a dream I had had where he died, and how in the dream I told him I loved him right before. And he said, 'Is this you telling me you love me?' I hesitated and said 'yes,' he said 'I love you' back, and we both started sobbing. It was probably the best feeling in the world. Three relationships later, and that moment is still the best."
28 of 33
Identifies as: Female
Age: 23
Age the first time she said "I love you": 21

"My boyfriend left the state the day I dropped the L-bomb. I was still in college, and he was staying with me, until he decided to move back home. A few hours before I dropped him off at the bus, we had the requisite sad goodbye sex. It was poignant and well-timed, but two back-to-back UTIs earlier that year had made me a staunch advocate of peeing immediately after sex. So, I took that as my opportunity to speak my piece before he was gone. As I threw on some sweatpants and made for the door, I turned and said, 'I love you.' Then, as any awkward, sad girl would do, I promptly exited the room. Before closing the door, I heard him say it back. We're still together — and, don't worry, I'm fine with saying it to his face now."
29 of 33
Identifies as: Female
Age: 26
Age the first time she said "I love you": 18

"I told him a story about how my mom says 'I love you' by squeezing my hand three times. It was young love, and I had a feeling we both felt that strongly for each other, so I was hoping he would take the hint. Later that day, he squeezed my hand three times."
30 of 33
Identifies as: Female
Age: 25
Age the first time she said "I love you": 19

"I was in my dorm room during the beginning of my sophomore year at college. I said it first over a Facebook message, to my boyfriend of about five months, who was a year older than me and abroad in Denmark at the time. I remember really wanting him to want to say it to me, with me — and his response was that he was not ready to say that sort of thing... So, I didn't feel great about it in the moment — and looking back on it now, it was a huge red flag. He cheated on me all throughout his time abroad and even once he was back. We proceeded to date for three years, until I finally ended things on my terms. My current boyfriend of three years told me he loved me first — without hesitations or regrets, and in person. And that is how it ought to be. Honesty and acceptance, without fear!"
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31 of 33
Identifies as: Female
Age: 24
Age the first time she said "I love you": 15

"I was at my best friend's house, having a sleepover. I'd been dating my 16-year-old boyfriend for about five months, and we hadn't yet said 'I love you.' My best friend was on the phone with my boyfriend, and she asked him, 'Do you love her?' — probably at my request, I can't remember now. He said he did. She passed the phone back to me; he giggled and said he loved me, and I said, 'I love you too.' Lots of giggles. I remember feeling nervous and excited, and happy. It is a little face-palm-y to look back on, but it's mostly a sweet memory."
32 of 33
When did you first learn about sex — and when did you first have it? "The first time I realized it was for procreational purposes was with some older friends of mine," the woman in our video explains, "and I remember looking in some kind of book that I had, and they were like, 'Sex is how you make babies,' and I was like, 'Nah.'" She soon learned that her friends were right. Watch the video for a glimpse into two twentysomethings' sexual-discovery journeys.
33 of 33
The first time isn't always great. Here, women share their stories of having intercourse for the first time and feeling less-than-positive about it. "He used Vaseline lotion," one woman recounts. "I think he was high on LSD — in fact, I know he was." If your first time fell short of movie-scene magic, watch and know that you are not alone.
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