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We were fifteen. I’d wanted to “do it” earlier, for bragging rights more than anything, but he said he felt too young. It was a few days after his fifteenth birthday. We set up the bedroom: lights off, candles on, best silky underwear from Primark. Snow Patrol was playing on my hi-fi. My parents were out. We tried once, but the pressure was too much and he couldn’t get hard. He cried. I was frustrated and texted my friends about the “wasted opportunity.” Later on, after my parents came home, we did it. It was painful and we had to stop after a couple of minutes, but we did it, it counted. I always thought I’d be the one on top, but I was underneath. We both cried. After that, we had sex like rabbits. I was never on top.
He was older than me, a musician I met at a party. I was 17 and trying to exploit my “singledom.” I gave him a blowjob in a bathroom and his best friend walked in on us. To avoid having sex, I lied and told him I was on my period. It didn’t matter in the end: he was a virgin and more nervous than I was. He also cried, the first time. He was inexperienced and watched a lot of porn. I was self-conscious and naïve. I faked all my orgasms. I wore uncomfortable, sexy lingerie. I snuck in and out of his house. He told me to shave off my pubes. I refused.
An acquaintance, we had sex for the first time after my 18th birthday party, in my best friend’s bed. Or rather, we tried. Again, although I didn’t know it, a virgin who was too scared to stay hard. We had casual sex in my parents’ bed on our mornings off college. We became a couple. He was talented, attentive, and attractive. I didn’t love him.
We’d met at college and had been flirting with each other for months. I was desperate to be with him. I was disappointed when it finally happened, in a friend’s spare bed. Not a virgin, for once, but a premature ejaculator. We were together for over a year and our longest session didn’t pass the 5 minute mark. He did love giving head, though.
The first person I had sex but no relationship with. We were drunk and in fancy dress. He ended up in my bed. I told him I wasn’t going to sleep with him. I changed my mind. There was something about him that I just found inherently sexy. He was the first person I’d slept with who already knew how to fuck. He made me feel attractive. He snuck out before our friends woke up. This time, I was on top.
This boy was crazy about me. In my fucked up, recently dumped state, I thought I was crazy about him too. We were a “thing”, but I was distant. The first time was awful. In truth, I wasn’t that attracted to him as I was still harbouring feelings for my ex. I thought sleeping with him would magically fix that. It didn’t. I went home with my underwear in my pocket, swearing I would never go back there. Two years later, I did. In that time he’d gotten into BDSM and knew what he was doing. It wasn’t mind-blowing, but it was infinitely better the second time around.
An attractive friend of mine, who I’d never really paid much attention to until I found myself single in the second year of my degree. I was in a long-distance relationship for the first year, and felt I’d missed out on the obligatory sleeping around that I was convinced was supposed to happen at University. We made out in a club, and had a few near misses in the weeks before we finally slept together. Eventually it happened because he tried to sleep with someone else and I got jealous.
Another friend I’d been getting flirty with. The night it happened, we were drunk, and you could cut the sexual tension with a knife. I was nervous: I knew it was going to happen, but I didn’t know how to initiate it. Luckily, he did. His dick was huge. I was pleasantly surprised at how good he was and how nice it felt. He was eager for me to orgasm, to make me feel good. I let him come on my face. We had sex three times that night. I went back for more, several times.
I was several years older than him, and much more experienced. He was tall and striking, with the best chest hair I have ever seen. He wasn’t relationship material, but we fucked a lot. He could only come when we did it hard, doggy style. I gave a lot of head. I felt sexy and confident as the older woman, but was frustrated that he didn’t know how to please me. Eventually, I went back to faking orgasms just to get him to stop digging around down there. We both had our issues, and they came out eventually. We don’t talk now.
I’d only met him hours before and he was ten years my elder. He was also, hands down, the best sex I’ve ever had. I can’t really put it into words. It was a defining moment for me, and made me realize how much I actually enjoy anal.