What it feels like to sleep with your best friend

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  • One writer reveals what it's really like to cross that line with your BFF

    ‘I didn’t have a sudden moment of waking up and realising that I’d slept with my oldest friend, because I hadn’t been to sleep. We’d had sex four times, and for the first time ever I’d orgasmed from penetration alone. The fact that it had all happened with a guy who I’d known for over ten years – and who I’d never been attracted to – only dawned on me three hours later, when we were dressed and sat on separate chairs on opposite sides of the living room.

    “I’m probably not going to mention this to anyone,” Sam said casually. “They don’t really need to know, right?” I laughed – a little too hard, perhaps. “Of course not,” I replied, feeling myself go red. His comment stung, and I wasn’t sure why.

    That afternoon, we hugged goodbye and later texted each other about unrelated, non-sexual things, as a conscious show of “seeing each other naked changes nothing”.

    Aside from predictably confessing all to one of our mutual friends later that week, I easily put the whole thing to the back of my mind. One-night stands in the past had come with a morning dose of guilt, like I’d sold myself short somehow. This felt different. I didn’t want a relationship with Sam, but it hadn’t been meaningless. When he rang me out of the blue six months later to say he’d tested positive for chlamydia and was worried he’d given it to me, our friendship made things easier again. I genuinely meant it when I said that I wouldn’t be angry if he had passed it on, and he knew he could believe me.

    It’s been three years since that night, but I’ve only recently realised that now when Sam stays in London, he no longer uses my floor as his crash pad. We’re both in long-term relationships and I don’t know if his girlfriend knows we slept together.

    When I told my boyfriend, he seemed unfazed – he’s slept with some of his female friends, too. But he still can’t make me orgasm through penetration, and when he asked me who had, I lied.’

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