What It’s Like To Finally Sleep With Your Long-Term Crush

The skateboarder and the rollerblader. Illustration by Sophie Wolfson

The sad truth about existence is that you don’t get to sleep with most of the people you fancy. Unless you’re a professional athlete or Drake, most of your crushes will stay unfulfilled.

Every now and again, though, the universe does you a solid and you get to hook up with the person you’ve been secretly in love with for months, years, maybe even your whole life. But how does it actually feel when you’re finally with someone you’ve fantasised about having sex with for longer than you can remember? Is it the best feeling in the world, or the ultimate disappointment? I spoke to some lucky (and also unlucky) people who managed to sleep with a long-term crush, with varying degrees of success.

HUGO, 27

VICE: So who was she?
Hugo: Basically where I grew up there were the skateboarders and the rollerbladers; I was a skateboarder and she was a rollerblader.

Like Romeo and Juliet?
Well, we were friends, but I had always fancied her; however she was obviously going out with a rollerblader.

When did you get your lucky break?
I moved away for a while, and when I came back she called me out of the blue and was like “I’ve run away from home, can I stay with you tonight?” I was home alone and obviously just said, “fuck yes.” She came round and we were just lying in the same bed and chatting. Eventually I decided to kiss her – as soon as I did that she just went full turbo and we started fucking pretty soon after. It was actually my first time but she didn’t know that.

What was it like being naked with someone you’ve known for ages?
It was dark and I didn’t get to see much to be honest. However I had always thought she had the best backside ever and that night I realised I was right. I guess rollerblading is good for your glutes.

How did you feel afterwards?
I was literally over the moon, both because I was finally losing my virginity and also because I had wanted to have sex with this girl forever and now I was actually doing it. Also in my teenage naivety I thought it meant that she actually liked me, I soon found out I was wrong.

What happened the next morning?
We got dressed and started heading out, and as we were walking down the stairs she turns to me and says, “Sorry about last night, obviously it meant nothing to me and I don’t like you but I was just lonely, you know? But thanks for the fuck.” It’s been over 10 years but I’m pretty sure that’s word for word.

Oof, that’s rough. How was your self-esteem after that?
Yeah I was just diminished to nothing. Then I spent the whole day hanging out with her while she hit on my friend. I tried to tell him what had happened but he didn’t even believe me.

I’m guessing there was not round two?
I haven’t spoken to her again since that day. But it was a good introduction to the world of sex. I had sex for the second time ever a week later with someone else.

ALICE, 26

VICE: How did you meet?
Alice: We worked together, sort of. I work in HR so he’s technically my employee and so it’s not really the done thing. But there’s no actual rule against it.

You’re in HR and you slept with your employee? Scandalous. How did you end up getting together?
When I first met him, I was in a long-term relationship that wasn’t in a good place. This guy was extremely good-looking and charming. He knew I was in a relationship but didn’t really care and had been trying to coax me into bed for a while. When I broke up with my boyfriend a few months later, I thought he would be the perfect rebound so texted him just telling him that I would go over to his after work.

Bold.
Yeah. When I got there he’d cooked dinner and got a nice bottle of red. We started hooking up but I left after about an hour of heavy making-out because I didn’t want him to think I was too easy.

So when did it actually happen?
About a month later I decided to just go for it. I went to his and this time there is no dinner, no wine, nothing. We went upstairs to his room and he laid on his front and asked me to give him a massage. This dude’s back is about the same size as my whole body but I gave it a go. After an hour of foreplay just for him we started having sex and he came after two minutes. He barely even touched me.

Did you stay?
I was so disappointed – especially after how hot the first night had been. I texted my friend who lived close by and pretended I had to leave due to an emergency.

Did it ever happen again?
He texted me like a week later and was like, “How could you leave me in the middle of the night, I want to be with you.” Even though I shouldn’t have, I gave it another go about two months after. He was more attentive but I just wasn’t really that into him by this point. I kicked him to the curb and got back with my ex soon after.

CHARLIE, 28

VICE: How long had you been crushing?
Charlie: I met her at university. I was told she had a crush on me but we were both in “serious relationships” so nothing ever really developed. But there was always something there and our paths would cross from time to time. Five years later I got a totally trivial message from her out of the blue while I was at work, one thing led to another and we ended up going for drinks the same evening. I was so fucking stoked, I’d had a secret crush on her for what seemed like forever and she was pretty much everything I look for in a girl: looks, personality, music taste, the whole package.

Did you go home together that night?
We went on a few more dates before we eventually slept together. When it happened it was amazing. I felt like I’d won the gold medal in long-term crushing or some shit.

How did it finally happen?
We went to a Vietnamese place near my house, had a cheap date and then went back to mine where we had that awkward “time on the bed before shit goes down” time. Then shit went down.

Was the sex weird or just great?
It wasn’t weird at all. I felt like Joseph Gordon Levitt in that scene from 500 Days of Summer.

Did it work out between you two?
We dated for a few months and then one night she told me over Facebook chat that she wasn’t looking for anything serious. A romance that spanned half a decade and it was killed in an instant over FB Messenger.

MONICA, 24

VICE: Tell me about your slow-burning romance.
Monica: He was a good friend’s ex. A couple of years after their relationship ended he starting hanging around with my extended group of friends and I had the biggest crush on him for about a year. In the last couple of months there had been so much tension between us: secret winks, holding hands and just general flirting, but I had also been hooking up with his oldest friend about a year before, so it was so complicated.

Who finally made the move?
One night, about a week before I was going to Thailand for two months, I bumped into him at a club. We were dancing together and he was complimenting me and buying me drinks, the full works. After that he disappeared for hours, then towards the end of the night he walked straight up to me and started kissing me and it was literally electric. Turned out the reason he had disappeared was because he’d been frantically trying to get through to his friend to bless the situation – he even called his brother!

Committed. Did you head straight back to yours when the club closed?
Yeah. We banged non-stop all night long, until it was daylight and beyond. We went to sleep for like an hour but I couldn’t sleep because I couldn’t believe he was in my bed. The next day I had to sneak him out of my house while my dad was in the shower so he just took my number and bolted.

How is it different to sleeping with someone new?
It’s so much more intense because there was such a build-up of tension, and also so much physical and mental attraction that it was just explosive.

Did you hook up again?
He waited for me to return from my two-month trip away and we were together and madly in love for two years. He’s still the only person I’ve really properly fancied.

BOBBY, 30

VICE: How did you meet?
Bobby: She was a famous actress – well, she still is. We met through mutual friends, first at a dinner and then like six months later at a party. I’d had a crush on her ever since I’d seen her in a movie a few years back.

How did you end up hooking up?
We were out partying and I was drunk so I told her that I saw her in a movie and thought she was stunning. She liked it and we ended up having a long chat and then she asked me to leave with her. We made out in the cab all the way back to hers and it was so good.

What happened when you got back to hers?
We continued drinking and finished off a bottle of champagne between us, then started to have sex.

It was the worst sex of my life, I was so disappointed…

How was the sex?
We started to have sex on the couch but it was small and leather so it didn’t go very well – I kept getting stuck to it. We tried to go to the bedroom but we were both wasted and on the way she bumped into a lamp and broke it – then she got really sad and weird because it had belonged to her dead grandma. Me and my boner did not give a shit about the lamp but I could tell that she was thinking about it while we were fucking so the sex was so bad. We tried a few different things but nothing was really working and she left the bed to go and collect the lamp pieces off the floor halfway through. After that we smoked a joint and then I left. It was the worst sex of my life, I was so disappointed.

How did you feel afterwards?
So bad, I actually had a girlfriend at the time so I felt fucking terrible.

Did you ever see her again?
She texted me a few days later and we arranged to go on a date but the vibe was so weird. I decided it wouldn’t be a good idea to try again. Now I just see her on movie posters everywhere.

STEPHANIE, 23

VICE: Where did you meet?
Stephanie: I met her at a NYE party years ago and fell in love instantly but she had a girlfriend who hated me and stared at me all night from across the room. The magnetism was insane, I’d never seen this girl before and until this point I considered myself to be straight. I’d never really thought about fucking a girl but as soon as I saw her I bounded over like a lovestruck puppy and introduced myself.

How much time passed before it went down?
Honestly I thought about her for years. I added her on Facebook and every time she popped up I’d spend like 20 minutes looking at her profile like a creep. I was obsessed. After about three years, I posted that I needed a driver for an advert I was directing and she replied. I had a total meltdown about what to wear and spent three days unashamedly flirting with her instead of working. On the last night of the shoot I got her super drunk and we snogged.

It was like losing my virginity again

Did you sleep together the same night?
It then took us another eight months. We happened to be in NYC at the same time and decided to stay in the same apartment. After a night out, we both came back to the apartment super-drunk. She climbed in the shower and I just stripped off and jumped in after her. We were just kind of fucking around and washing each other’s hair and stuff – it was kind of bound to happen but we were both being cautious I think because she knew I hadn’t been with a girl before and I was scared. Then we started kissing and I was losing my shit – I wanted to lose myself in a moment of passion but I was being so calculated because I didn’t want to fuck up. All those years of build-up to this explosive moment and then I’m just thinking, ‘Err okay lol I guess I’ll put my hand HERE.’ We spent the rest of the night banging, or in my case, working out how to bang. It was like losing my virginity again.

How did it feel to finally be with her?
It was like rediscovering your entire sexual identity in your 20s. Everything I knew about the male body and sex and pleasure was suddenly irrelevant and it was all really strange. Even though I’m incredibly liberal, the years it took me to overcome whatever strange fear or bizarre perception I had about my sexuality made it really intense when it finally clicked.

Did you have sex with her again?
Multiple times, for years. We’re still incredibly close, but just as friends.

SYLVIE, 23

VICE: Who were you crushing on?
Sylvie: My friend was doing an art foundation course and I met this guy through him. I was into him immediately, he had curly hair and an air of mystery about him. I tried my usual tricks and made an effort to go to any art school party I thought he’d be at, but nothing worked. I was a lot younger than him at the time.

Was he waiting until you were older?
I don’t know, he always gave off a vibe that I wasn’t cool or “art school” enough for him. But two years later another friend of mine was having a house party and it turned out he was coming. I was thinking ‘this is my time!’ so I put on an all-black outfit and decided to try my luck one last time.

We were fully mid-fuck when suddenly he jumped up and ran to be sick

How did it go?
We talked a lot at the party but I don’t remember the details. He told me he’d got some nice weed in and invited me back to his. I was basically jumping for joy inside at the prospect of finally fucking my crush while stoned. The dream.

How was the sex?
We were smoking and things started to get steamy – we were fully mid-fuck when suddenly he jumped up and ran to be sick. He spent a good hour in there while I lay there thinking ‘oh god he won’t wanna finish now.’ He then returned looking more sorry than embarrassed. He passed out next to me, and I smoked his weed until I passed out too.

Was it good before he puked?
I think it was only good because I’d fantasised about him so much previously. I was so caught up in this fantasy while fucking him I probably convinced myself it was good, when actually it was really fucking shit.

What happened in the morning?
He didn’t offer me breakfast, just walked me to the door. We both stood there in awkward silence until he said “should I take your number?” I told him there was no need. All in all, a complete let-down. I never saw him again.

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