No Two First Times Are the Same

Written by Aimee Wheeler

First sexual experiences are confusing, exciting, awkward, and unforgettable. They shape us in ways we rarely notice, and the stories we carry reveal the mess, the thrill, and the humanity of our first steps into intimacy.

How often do you think about your first time? That moment that, at the time, felt enormous, confusing, or even a little scary. Most of us try to forget it or at least gloss over how innocently naive we once were, no matter our age or experience. Yet those first encounters shape us in ways we rarely notice, leaving behind stories that are funny, awkward, tender, and unforgettable. Here, Kiss Kiss readers share their own experiences, offering a glimpse into the mix of nerves, curiosity, and discovery that comes with taking that first step.

“We laughed as we heard Kung Fu Fighting playing in the background. That became our song”

Cadon,19, from Devon :

How did your first time happen?

My first time was with my first boyfriend, John. It was our second date. He was spending the day with me at my house for the first time, and we were home alone, sitting on my bed, playing Minecraft together, listening to one of my Barbra Streisand playlists. He was being silly, so I pushed him, and we started play-fighting. Suddenly, he was on top of me, and he kissed me. That was my first kiss. We kissed again, then suddenly we were having sex. It wasn’t his first time, so he knew what he was doing. It lasted about half an hour as we explored each other’s bodies. I was quite self-conscious and nervous about him exploring me.

We eventually stopped and ended up lying there together under my duvet, his head on my chest, listening to music. We laughed as we heard the theme tune of Kung Fu Fighting, the original dodgy version playing in the background. That became our song, and it still makes me cringe when I hear it, as it is an unusual song to have tied to that memory.

Any regrets?

I wish I’d been more confident in myself. He was dating me, kissing me – he found me hot, and that was powerful. I enjoyed the experience, and it was fun, but I do think of it negatively because we ended up breaking up a couple of weeks later, as we just weren’t good together in a relationship. I’m sad that all my firsts happened on the same day: first kiss, first time, first time I officially had a boyfriend.

How do you view it now?

I view it positively and negatively, to be honest. When I think of it, I think of how I felt when he broke up with me, and that feeling wasn’t nice. But It wasnt horrible, and we both connected in such a nice way, so it isn’t a horrible memory. Having that experience gave me confidence when I decided to have sex again, and for that I am thankful. 

Gracie, 24, from Southampton :

How did your first time happen?

I was 15, in year 11, with my boyfriend of around one month. He’d had sex before and knew I was a virgin. It was a very common conversation topic in that first month; sex would often be brought up, always followed by “we’ll do it when you’re ready.” But it was brought up so often that I did feel pressured. Eventually, when it happened i was thinking just to get it over and done with. We were round mine and watching a film, cuddling, and we started kissing, and then it ended in us having sex. I told him I was ready, and he made me feel safe and comfortable, but I felt as though it was definitely some sort of pressure that made me do it so soon. 

Any regrets?

The next day at school, by lunchtime, I felt like half the school knew. He’d told all his friends, and naturally, I’d told mine. I don’t regret it at all because I felt comfortable the whole time, and to me, that was the most important thing. But finding out it was being bragged about to a bunch of boys, that’s when I sometimes wonder if it was with the right person.

How do you view it now?

Somewhere in between. Positive because I personally felt ready. Negative because the reaction afterwards made me feel quite insecure. For me, sex is such a personal, intimate moment, and having it shared with a lot of people wasn’t what I wanted. It hasn’t affected my relationship with sex, but doing it so young made it easy for other people to see me negatively, so my experience with boys at school changed, and I wasn’t happy about it. Luckily, now I am in a relationship with someone who respects our intimacy and my body, and he wouldn’t brag about it. Comparing my first to my current boyfriend has helped me appreciate how I am being treated and how I’d like to be treated. 

“I remember being sick with nerves but also giddy”

Jack, 21, from Portsmouth :

Any regrets?

I don’t really remember what happened, but I remember how I felt, and that’s the most important thing. I felt safe. The experience was as good as it could have possibly been. We were clueless, and I remember being sick with nerves but also giddy. It was overwhelmingly exciting, and I wouldn’t have changed a thing.

How do you view it now?

There’s definitely nothing negative to reflect on. We were both virgins, both exploring for the first time with no pressure of competing against each other’s previous experience. We were attentive. We did it when we felt ready. I’m grateful that my first time was with someone I trusted and loved. I am grateful that I got to experience a (generally) healthy two-year relationship at a young age, which is rare for many gay men in our community. I’m 21 now, and I hear lots about falling into the trap of gay hook-up apps when they were underage, having sex for the first time with typically much older men who exploited their innocence for perverted pleasure. It’s a common issue in my community, and I am grateful that it didn’t happen to me.

Beth, 21, from Brighton:

How did your first time happen?

I lost it when I was 17 to my boyfriend. It was nice, I felt comfortable with him, and it was with someone I was really in love with at the time, so I don’t regret it at all. It was a very big deal for me as I hadn’t been with anyone during secondary school like my other mates. I was very insecure and worried, but he made me feel calm and safe. I’d had lots of bullying in the past in that way; I was looked down on by others in secondary school, which made me so insecure, so I really waited until I found the right person. We were in my house, and no one was home. He was staying over, and it just happened. I kept as much clothing on as possible, and it hurt a lot! But it was nice.

Any regrets?

The only thing I regret is being scared of it for so long. I’m glad I did it when I did, but I wish I weren’t so afraid and that people hadn’t made me feel so insecure. I was still figuring out my sexuality, but the people in school were so horrible to me about my body that it really impacted me. The pressure to do it was definitely a reason I went through with it, as a lot of my friends did it in secondary school, so I was considered late or frigid in their eyes. Although I don’t regret it, I wish my views around it had been different.

How do you view it now?

Positively. The people around me at the time made me feel so happy and loved. My best friends made me a cake with the word “virgin” crossed out, and it was funny, but so thoughtful that I was tearing up. In that moment, I felt seen and accepted and understood, not judged for not having done it earlier, but understood that it was a big deal to me. Without the people around and my boyfriend at the time, I think I’d still be a virgin. But now, with that experience, I’ve become a lot more confident and used to having sex. 

Imogen, 20, from Leeds:

How did your first time happen?

My first time was when I was 18. At the time, I was upset because I hadn’t done it yet, and I felt so far behind everyone else (obviously, I was wrong).

I went out with friends on New Year’s Eve, back in my hometown. There, I met a girl named Bella. We exchanged Instagrams, and after midnight, I found her for a kiss. She invited me back to hers, and of course, I said yes.

Her house was a mess, and she gave me half a glass of gin and lemonade before we went upstairs. I put on Jeff Buckley, and we had sex. I remember having absolutely no idea what I was doing. It wasn’t perfect, but I didn’t care. I think we even had a round two, so I guess it wasn’t that bad.

Later, my mother gave me a lift home from the station and knew I hadn’t been at the Airbnb. Thankfully, she ignored the hickey on my neck, and my giddy mood slowly returned with just a hint of embarrassment.

Any regrets?

Honestly, not really, it was chill. A bit awkward, a bit embarrassing, but altogether an easy one-night stand that I basically never had to think about again. Just the way I wanted it. I don’t have any regrets that have stayed with me, my thoughts and experiences with other people, so for me, that is good. 

How do you view it now?

Somewhere in between, for sure, but definitely more on the positive side. It wasn’t the best sex in the world, but I wasn’t expecting it to be. It was exactly what I wanted: something quick and easy that I could just get out of the way so I could say I did it. Plus, the fact that it was with a girl is something very positive for me. At the time, I was struggling with my bisexuality, thinking that maybe my brain was just convinced it was attracted to women so I could seem cool or interesting or something. Having my first time be with a woman who I was attracted to, who wasn’t older and taking advantage of me, meant a lot to me then, and still means a lot to me now. My first time with a man, however, wasn’t until a few months later.

“I see my virginity as something I can decide when I lose. I’ve decided to give it back to myself as a Christmas present.”

Alfie, 22, from London:

How did your first time happen?

I lost my virginity when I was 17 to a man whose name I do not know and never knew. I met him at an Airbnb on the road next to where a friend of mine lived. We started talking on Grindr. He didn’t know I was 17 or that it was my first time. As soon as I got there, I wished I’d stayed at home, but felt too awkward to back out.

Any regrets?

I wish I’d waited for something special to happen rather than rushing into things. It wasn’t the right time for me. I was depressed, sexually frustrated, living with my parents, and having intense feelings about my gender and identity. I wish I knew his name. I barely remember his face.

How do you view it now?

I never consider this to be my first time when looking back on life. I try not to think about it at all, to be honest. He was a kind man, and didn’t force me into anything, but I still feel I shouldn’t have gone there. It stands as a learning opportunity for me as a naïve teenager, but that is all. I’ve been too scared to have spontaneous relations with men ever since. I see my virginity as something I can decide when I lose. I’ve decided to give it back to myself as a Christmas present and re-virginise myself.

Ellie,26, from Bristol:

How did your first time happen?

My first time was with my best friend of 10 years. We were sitting on my sofa in my flat, watching some TV show we were obsessed with, drinking wine and gossiping as we usually did. We were cuddling, we have always been close, very affectionate people who love a cuddle and a cheeky kiss now and then, but we were never romantic or sexual in that way. The show had some sort of funny scene that got us both cracking up hysterically. We were laughing. It was nice, we ended up kissing at some point of the night, but usually we’d only have a snog if we were out somewhere at bars, you know? I don’t remember how we got to kissing, but it happened, and we had sex.

Any regrets?

I wish we’d done it sooner because we know each other so well; it just worked. But I’m happy it happened the way it did. He was truly my best friend, and I love him so deeply. Now, we’re dating.

How do you view it now?

Positively. I’d had some bad sexual experiences before having sex, such as sexual harassment in clubs and overly touchy dates, and that really put me off. Having him be someone I knew was so refreshing. It helped a lot that I was comfortable when we were that intimate, after having had bad experiences in the past.