Sophie Cullinane | Features Editor | Wednesday, 4 March 2015

Confessions of a Serial Cherry Popper

The Debrief: Taking someone’s virginity once is pretty standard, twice might be considered sloppy, but four times?! We ask Steph, a 24 year-old serial cherry popper, to fess up…

Illustration by Beth Hoeckel

‘Three weeks ago, I woke up naked in a stranger’s bed with one of the worst hangovers I’ve had since I graduated from Durham University two years ago. With a cloudy head, a fetid tasting mouth and an imminent feeling of doom threatening to take me over, I rolled over and confirmed my suspicions that, yes, I did in fact have sex my mate’s new ridiculously fit housemate Thom from Canada who I’d been flirting with for the last month. This was enthusing news. Aware that I was probably not looking my best - and keen to put in a repeat performance that I’d actually remember - I decided to do the honourable thing of sneaking out before he woke up to go back to my place and gossip with my friend about this new development over a stuffed-crust pizza and a family sized bottle of Coke (each).

It was, I thought, the perfect way the spend my post-sex hangover - that was until I saw the look on her face when I told her it was Thom who I ended up going home with last night. What she knew and I was slowly beginning to realise was that last night was probably more significant for Thom than it was for me. Because, unlike him, I’d actually had sex with other people before. Yep, Thom, it transpires, was until recently a devout Christian and a virgin before last night, which would make him the fourth person who’s cherry I’d popped in as many years. Yes, I said fourth. 

Getting off on popping people’s cherry isn’t a sexual quirk that I have, it’s just that virgins seem to be unable to resist me

‘Before I go on, I think it’s important that I make something explicitly clear. I have no kinky attraction to virgins. I don’t find the idea of popping someone’s cherry a massive turn on, I haven’t even seen The Graduate and I’m not particularly keen on being dominant in bed. As far as my ‘normal’ sex life goes, I’m pretty vanilla. My favourite position is me on top closely followed by missionary, I own one small sex toy which I was given for my 18th birthday by an old boyfriend and I lost my virginity on my 16th birthday to my (non-virgin) 17 year-old boyfriend of a year and a half. So getting off on popping people’s cherry isn’t a sexual quirk that I have, it’s just that virgins seem to be unable to resist me.

‘The whole thing started two years ago after I’d just come out of a three year relationship with my boyfriend from back home in Bristol after he cheated on me with a string of girls he’d met online. Heartbroken, I started falling for a guy on my course who seemed to be his polar opposite of my ex - he was kind, gentle (albeit a little withdrawn) and seemed keen to date without rushing me into a physical relationship. Four whole months passed before I felt like I was ready to take our relationship to the next level, but when I initiated sex he just turned over and went to sleep. Hurt, I asked him why he wasn’t interested in a physical relationship and eventually he tearfully admitted that he’d never had sex before and was worried that he’d disappoint me in bed.

I admit that I was a little bit put off by the fact he was so inexperienced, but I really liked him and I wanted to continue seeing him, so we decided to give it a shot. The sex was pretty bad at first (it felt like he was just masturbating with a woman attached) but we really enjoyed each other’s company and things got easier the more I told him what I needed in bed. The relationship fizzled out over the next few months, but neither of us regretted helping each other through a difficult period in our lives and we remain really good friend to this day. 

I was after some reckless fun and decided to throw caution to the wind - so what if he was bit of a shit and two years younger than me?

‘The next virgin was a different story. I was in my third year and I had be assigned a small group of third years to run a seminar with as part of my course and one of them was a 19 year-old guy called Sean. He was insanely arrogant, pretty rude, completely uninterested in my presentation that I’d prepared and (infuriatingly) one of the most attractive people I’d seen in ages. When he asked if I wanted to get a drink with him and his other first year mates, I knew it was a terrible idea but I was after some reckless fun and decided to throw caution to the wind and let my hair down a bit - so what if he was bit of a shit and two years younger than me?

Fast forward to four hours (and about 20 shots of tequila) later and I was being felt up in his damp halls bedroom with a Pulp Fiction poster on the wall. Horny and too drunk to appeal to my better judgement, I peeled off his trousers, gave him head and we had about two minutes of drunken sex before he rolled over and fell asleep. It wasn’t exactly the most romantic liaison, but in my head it was a bit of fun and nothing to freak out about. Boy was I wrong. After a couple of weeks without seeing or hearing from him again, I asked one of his course friends how he was and he told me that he’d broken up with his girlfriend after she discovered he’d cheated on her with  ‘some much older random woman’ he’d ‘randomly picked up at a bar’. Ah. After some terse text messages were exchanged, it transpired that he’d been with his girlfriend since he was 14 and she wanted to wait until they were married before they had sex. Desperate not to be the only virgin fresher at Durham, he’d basically set out to get his end away and I was the first idiot drunk enough to comply. We did not see each other again.

‘I didn’t find out Eamon was a virgin until three weeks after the first-year incident, when he started seeing my friend. I’d actually slept with him during freshers week two years previously whilst me and my boyfriend were on a break and, although the sex was great I quite liked him, I ignored his ever-increasing messages because I wanted to give things another shot with my boyfriend. We were both gobsmacked and embarrassed when my friend introduced us and we realised we’d bumped uglies, but although I was a bit cringed out, he seemed really hostile and he swerved from ignoring me completely to being down-right offensive whenever our paths crossed. Exacerbated, I told my friend what happened and asked her if she could get to the bottom of why he seemed to resent me so much for what I always saw as a bit of a drunken fling. Well, it turns out, he had a pretty good reason - I had been his first time and, before I started completely ignoring him and sleeping with my ex again, he had hoped to turn the relationship into something really serious. I felt so bad for what I had done to him, but a part of me did wonder if I’d been in some kind of hidden camera show. By now started off looking like bad luck was now looking like a pathological problem. My friends even started calling me the virgin stalker. 

‘So here is what I’ve learned from four years of deflowering men. Firstly, always ask about someone’s past relationship history if you’re concerned that you might be about to have sex with a virgin - you can catch the signs early and make an informed decision about weather or not you want to take the plunge. Secondly, just because someone hasn’t penetrated another human before does not make them an innocent wallflower - virgins are just as likely to be a dickhead as the rest of the population. Thirdly, ignoring someone’s text messages is always rude and should be avoided at all costs and finally, there are some benefits to having sex with multiple virgins - at least you don’t have to worry about STIs.’

Liked this? You might also be interested in: 

What Really Happens When You Lose Your Virginity?

Why Losing My Virginity On The First Night Of Fresher's Week Was A Terrible Idea

Six Years After Losing My Virginity I've Just Had My First Orgasm 

Illustration: Beth Hoeckel 

Tags: Sex, NSFW, Sex O\'Clock