My Very First Time: Women and Men Share Their Stories

Losing your virginity is a big deal. I remember my first time like it was yesterday. Not only was it painful the first time, but it hurt like hell a few times after that. I soon realized that it was not at all like how the movies portrayed it to be.

No matter how old you are when you decide to pop your cherry, it’s a very intense moment. Things can get interesting and your very first time is one you’ll never forget. A relationship writer spoke with a few adults about their first time. From being scared as sh*t, to just wanting to get it over with, women and men talk about the first time they had sex.

Lauren

Credit: gpointstudio/Shutterstock
CREDIT: Credit: gpointstudio/Shutterstock

I was a junior in high school and had been with my on-and-off again high school sweetheart. He was extremely respectful of me and my body. I always felt safe and protected with him. We had a couple close encounters before – making out then eventually into oral sex – but I told him I refused to lose my virginity in the back of a car so it was what it was. The week of Valentine’s Day, it was clear from our body chemistry that we weren’t going to be able to put it off much longer so that weekend, we went shopping and eventually went over to one of his really good friend’s house for a couple’s movie night. His friend’s family had a theater in the basement with an attached guest bedroom so that was the scene of the magic. When we finally went in the room, I wasn’t nervous but I was afraid from our most recent attempt that my first time might hurt. I took control, got on top, and eased my way down. He was very gentle with me, making sure I was okay, until I no longer wanted him to be gentle.

The soundtrack was whatever movie was playing. But in my mind, the song that I knew I would lose my virginity to was “Take It Off (Dim the Lights)” by Pharrell, an album that I was absolutely obsessed with at the time, so that’s what I fantasized about while we were doing it. When it was over, I was expecting the world and the universe to shift, but I pretty much felt the same as I had always felt, just normal. I was excited to share with my friends that I had finally been initiated as a woman but even then, I don’t think I said anything until weeks later. I felt just as close to my boyfriend then as I had always been, and although I knew that he wouldn’t be my husband or anything, I was and am still, very happy to have given my virginity to him.

Jane

Credit: wavebreakmedia/Shutterstock
CREDIT: Credit: wavebreakmedia/Shutterstock

My earliest sexual memory was when I was 8, I was young (laughs). I think my classmate wanted me to touch his penis in exchange for some candy. I was like, I wanted some candy, he has some candy, so I’ll touch his penis. Even when I was young, I remember dry humping with people. I can’t remember my first taste of sex, but I remember I was really young. I lost my virginity when I was 19. I don’t know how to word this, but this person was the first man I ever felt comfortable with outside of the males in my family. At this point we weren’t even quote unquote together, we were just friends. I developed really strong feelings for him and vice versa. I was really comfortable with him, he was just different. He didn’t make me feel like I had to be guarded, or scared, or nervous. I was just really comfortable which is probably why that came about. Because of previous trauma, I had a detachment to sex. I felt like sex made girls damaged. I had a misogynist view of a woman being touched sexually and that making her “destroyed”.

I thought sex was taboo and a thing people did to be nasty. That was all prior to him though. I wasn’t afraid to lose my virginity. I was ready. I hadn’t heard a lot of horror stories. The people I had known who had lost it had really exciting, thrilling stories about it. I would always hear, “You know when you’re ready”. I remember it hurting. I remember overthinking it, like what if he doesn’t like me after this? What if it’s not good? Physically, it hurt at first, but it was like a welcoming pain, like (sighs), I can deal with this pain. We were in my dorm room. My roommate was gone. I was wearing a t-shirt and shorts. I remember the music was on. I think my feelings at that point were invalidated through him. I hadn’t completely let go of the “sex destroys women” perspective I had, but he invalidated those beliefs because he made me feel so pretty afterwards. He didn’t dog me out. He didn’t leave. I had this feeling of immense reassurance from him. I don’t have any regrets, but I kind of wish I wasn’t as grossed out by sex as long as I was.

Shauna

bored woman in bed with boyfriend
CREDIT: Monkey Business Images/Shutterstock

I was 18 when I lost my virginity. I was with the guy for two years at the time. We went to the same high school together, but he was a grade ahead of me. I was under the impression that I was in love and that we would last forever. Now that I think about it, he had been making me feel a little guilty about not doing it. We broke up the summer before and I met some people and did some things, obviously not the big thing, but I did some things. We reconciled shortly after. I don’t think there was anything special about him other than the time and energy I felt I put in the relationship for the two years it had been a thing. I was obsessed with sex. Obsessed with it, and really wanted to do it but I was picky and wasn’t about to do it all willy nilly. I was afraid though. I knew what to expect but it was happening and it was my experience so there was some fear and apprehension there.

I’m looking back at it like “Damn Shauna” (laughs). I kinda just went for it one day. It was on the floor of my dorm room, freshman year of college, first semester (laughs). It just happened. One thing escalated after the other, and I was just like eff it. I was feeling like, “Am I doing this right? Is everything alright body-wise?” I was really confident body-wise. Like goddamn, I was hot as sh*t back then and I look back and feel like I wasted my time with this fake ass Mexican. Afterwards, it wasn’t like a shellshock, but it was like, so I just did it, okay. It was alright. Honestly, my first time wasn’t that great. When I look back, he wasn’t that great. It hurt. He made me fried chicken and mac n cheese afterwards. But damn, if I knew then what I know now, I would have ruled college life.

Jason

Man kissing woman's forehead
CREDIT: Jurij Krupiak/Shutterstock

I was 17 and it was right before my senior year. She was the most significant woman I’ve ever had in my life. I was a guy and a senior in high school, and at that point, I was the only person in my group of friends that hadn’t lost it. But I wasn’t about to give it to just anybody. At the time, the girl I was with was the most important person in my life and honestly, I took her virginity as well so it was kind of a mutual thing. She made me feel like I was the greatest man on earth which is part of the reason why I have the ego that I have now (laughs). I feel like the first time with anybody is really awkward, especially for us because it was both of our first time. It hurt for her and she bled a little bit. I don’t feel like my first time is worth remembering other than the fact that it was my first time (laughs)—that’s the only reason the story is memorable. I lost it at four in the morning in the computer room of my grandfather’s house.

I was really eager to do it, but I wasn’t eager to throw it away. The furthest I’d gone before her was a semi-handjob so I was very sacred about what I had. From an ego perspective afterwards, I felt free. I felt like a weight was lifted. I didn’t even have to tell people, they just knew. It was in my demeanor, the way I talked, how I carried myself. They knew something happened to me. My uncles asked me, “Did you lose your virginity? Did you wear a hat?” There was this coded language (laughs). But sex didn’t make me look at her any differently. I didn’t love her any more, I didn’t love her any less. It was something to get out of the way to focus more on the relationship. The act of sex was just something we were ready to be like “Okay, we’ve done it already.” After losing it, I was eager to do it more though and do it better (laughs).

Dexter

Credit: Skuropatskaja/Shutterstock
CREDIT: Credit: Skuropatskaja/Shutterstock

I was 16 and at my buddy’s house. He was a really great friend of mine—all of us were pretty close because we grew up together. There was me, my friends, my buddy’s parents, her, and her mom in the house. She asked me to come in her room. She was my childhood sweetheart so we always had a thing. We were talking, joking around, being kids; One thing led to another. We started having sex, and it was the scariest thing I’ve ever done in my life. Her mother’s bedroom was four feet away from where we were and my buddy’s parents’ room was the wall that separated us in that her room.

It was really awkward because in the background all I heard was this fighting game so it was a whole bunch of males moaning the entire time (laughs). I was distracted, but still really into it because she was so beautiful to me. The next morning, she moved to California, so that was awful. I thought it was overrated. When we had sex, I was like, “Oh okay.” I never really felt this intense pressure to have sex because none of my friends were really having sex like that except for my homeboy that had started in the eighth grade. There was way too much foreplay, like way too much foreplay. We were both scared because we didn’t have a condom. We had sex for like fifteen minutes and stopped because we didn’t want her to get pregnant at 16 so the foreplay started back up. Like a couple of weeks after, I wanted a new experience to really experience what sex is like in a more comfortable setting so I lost my virginity and shortly after, that became my hoe phase (laughs). Sex was incredible.

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