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How I "Lost It": Women Share True Stories Of Their Firsts

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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 honour 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.

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."

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..."

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."

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!"

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."

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."

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."

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."

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."

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.'"

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."

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."

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."

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!"

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."

When did you first learn about sex — and when did you first have it? "The first time I realised 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.

Like what you see? How about some more R29 goodness, right here?

How To Get Over Your Nerves & Finally Tell Your Crush You Like Them

Is There A "Right Time" To Bring Up Marriage When You're Dating?

16 Tips For Sharing A Bed With A Partner


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