Sophie Cullinane | Features Editor | Wednesday, 11 February 2015

'He Had A Pained Look On His Face The Entire Time:' What Happens When You Take Someone's Virginity

The Debrief: When Grace’s Tinder date ended with sex on the first night she didn’t really think it was that big of a deal – until she realised that it was her date’s first time. Ever.

Photo by Molly Cranna

The old wisdom goes that losing your virginity should be one of the most (if not the most) emotionally significant events in your life. The moment you decide to have sex for the first time is loaded and heavy with symbolic meaning – when your mum first told you about the birds and the bees she explained that sex is something that happens between two people very much in love and that’s a powerful message to try and shake. All our lives we’ve been fed the message that our virginity is the most precious gift we have to give away and that the first time we have sex it should be after lots of serious thought and with someone we know and trust. It’s a lot to live up to but, thankfully, it’s the way it happened to me when I was 15 and me and my boyfriend of two years fumbled through three solids minutes of bonking and I emerged tentatively – and a little sore – into the world of womanhood. It was that way for me, but it sure as hell wasn’t for Mark, the 24 year-old guy whose cherry I unknowingly popped on the sofa in my living room after getting royally twatted on our first date.

If I had any concerns, I pushed them right to the back of my mind to make room for the prospect of some boning and FUC (fresh, unchartered cock)

Our story like most modern matters of the heart, began with a swipe to the right. I was instantly attracted to his Tinder profile, which included pictures of Mark engaging in three of my favourite activities – eating Pizza, wearing Nike trainers and hanging out with a puppy. It was a solid yes from me. I’d been using Tinder on and off for about eight months with varying degrees of success – four dates, two snogs, one shag – but the chat was instantly really amazing with Mark and he seemed confident, attentive, funny and up for a bit of fun. After being completely ignored by the last guy I’d slept with, he was giving me the attention that I was craving and I was gagging for him to ask me out. After nearly four weeks of Whatsapping I was beginning to lose hope in him actually being interested in anything other than flirty messaging, but at 7am on a Tuesday morning he finally plucked up the courage to ask me out. I was slightly weirded out by the fact that he’d was thinking about me before I’d even brushed my teeth but there wasn’t any other prospects on the horizon and I was hardly in a position to complain. If I had any concerns, I pushed them right to the back of my mind to make room for the prospect of some boning and FUC (fresh, unchartered cock).

He arranged to meet me straight from work and I headed there fifteen minutes early – I wanted to be safely ensconced at the bar to avoid having to go up to randoms and ask ‘are you Mark?’ – and was already on my second large glass of Merlot  when he arrived looking scared shitless and shaking like a leaf. I felt really sorry for him and instantly went in for a big bear hug to try and calm him down, which seemed to work because before long we were doing shots at the bar and cackling about our only mutual friend – a mate of his from uni and someone I went to primary school with.

He was fit and funny and, even though he was still a bit nervous, the alcohol in my system was making me brave enough for the both of us and when we went out for a fag I leant in and kissed him. For the next few hours, the only time we came up for air was to pour more booze down our necks at, come 10pm, I was absolutely battered with a sore face from stubble rash and hornier than I’ve ever been. When I asked him if he wanted to come back to my place, he looked shocked and a faintly terrified, but as I woozily grabbed his dick through his jeans his face softened and I convinced him to order us an Uber.

Both of us were pretty messy by the time we got back to my place. When he struggled to take my bra off I put it down to the booze, but when I sat down on the sofa in my living room, guided his hand down my pants and he a pressed on my clitoris so hard I thought he was trying to push it back into my body I started to have concerns. Hoping that things would improve once we actually got down to it, I took his trousers off and went to give him head, but he instantly yanked my face up to start kissing me again - which was, to be honest, pretty insulting. Oh dear.

He had a pained look on his face the entire time which told me he was concentrating (hard) on not coming. Which he did. After maybe four minutes.

Suddenly out of nowhere, he shouted ‘are we going to use a condom?!’,  so I went over to my wallet and took one out, which he grappled with over his (frankly, enormous) penis for what felt like an hour but was probably only a few minutes.  Despite the huge cock, it wasn’t the most elegant of positions to watch a potential love interest in and by now I really just wanted to get the whole thing over and done with. The sex itself wasn’t the worst I’ve ever had because I took things into my own hands on got on top, but he had a pained look on his face the entire time which told me he was concentrating (hard) on not coming. Which he did. After maybe four minutes.

Exhausted and still completely wasted, I conked out on the sofa and only woke up when I felt Mark shuffling around in the morning looking for his clothes. My head was pounding and I really didn’t want a repeat of last night, so I’m embarrassed to say that I pretended to be asleep whilst he collected his possessions and left. Anyway, I couldn’t be certain, but I think he might of been crying and I was just way too hungover to even attempt to deal with that for the time being.

Neither of us contacted each other for a week which made me feel kind of dejected, especially within the context of my romantic history over the last few months, but wasn’t particularly surprising - it sex wasn’t exactly an indication that things were going to work out between us long term. But then just as I was leaving the house to go to work, I received a text that may my jaw hit the ground. It said: ‘Hey Grace. So sorry not to have text you since our date. I think I should give you a bit of an explanation as to why I left so abruptly in the morning. Until three months ago, I have been engaged to a girl from my church and she had wanted to wait until the wedding night until we had sex. Things obviously didn’t work out between us, but I was with her since I was 14 and I am quite inexperienced sexually and the whole thing was a bit overwhelming the other night because it was the first time I’ve actually had full sex and it’s taken me a little while to come to terms with it. Anyway, I hope we can see each other again soon because I did have a good time.’

What the fuck do you say to that?! I felt instantly sick as the weight of what had happened the other night washed over me. My drunken Tinder one night stand was actually one of the most significant nights of this 26 year-old man’s night. If this was any ordinary guy, I’d have just ignored the text after last week’s performance but Mark had lost his virginity to me, didn’t I owe him more than that? Won’t he probably want to go out we with me? Or at least do it again so he can tell all his friends? Should I talk him through everything and make sure he was emotionally secure?

These and a thousand other questions rushed through my brain whilst I grappled with the enormity of what I’d just done, but the truth was I also felt a little bit proud. Of everyone in the whole world, Mark had chosen to give his virginity to me - surely that meant something? We got on really well and it was obvious he trusted me and found me irresistible, maybe I shouldn’t write this one off too quickly and give him a bit of a chance. 

Well, the answer to that came in the form of a text message once I’d gotten to the other side of the tube:

‘Grace, I’m sorry but maybe it isn’t such a great idea to see each other again. I’m still very much in love with my ex-girlfriend and am going to try and get back together with her. I hope you understand and I think you’re a wonderful girl.’

Hmmmm…maybe not that significant of a night for Mark then. 

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Tags: Sex, Sex O\'Clock