Confessions: What’s your worst cheating story?

It’s too late now to say sorry


Last week we started our confessions series sharing the worst of the worst one night stand stories you had to offer, from finishing yourself off to bedroom shrines of the royal family. This week, we’re going deeper on guilty confessions. Being cheated on stories are pretty standard: they’re obviously total cunts, you’re the wronged victim, you don’t know if you’ll ever be able to love again. What’s worse is hearing it coming direct from them. Why did they do it? What exactly happened? Do they even feel bad about it? We asked you your worst cheating stories to find out.


I had a pretty long term boyfriend but things hadn’t been right for a while and I really wasn’t sexually attracted to him anymore. I know this really isn’t an excuse to cheat but it happened, a few times, and I didn’t really feel guilty. For about a year I’d been in contact with and flirting with the guy I cheated with — because he was also my boss — but that was more for the thrill of it and because I never saw him, it didn’t really seem like anything. It was back in Easter when I went for what I thought was a friendly drink with him, but before I knew it, I was staying over at his having had a long night of sex and not much else.

I thought it would be the only time but I couldn’t help myself going back for more, not least because the sex was outrageously good, but it was thrilling and no one had a clue. Things escalated quickly and it got to the point where I had to end things with my boyfriend because I felt so bad and realised I was being a massive bitch. The worst part is I’ve been cheated on before and now how horrible it can be, so I’ve never admitted it to anyone.

I’ve quit that job now as well.


Case for the defence: I was feeling really, really awful. It was the first night of Fresher’s Week and instead of being excited, ready to strike out and be independent and be a proper person with their own electric heater and bonsai tree, their own corky wall with loads of pics of their home mates stuck to it – instead of being that, I was fucking miserable. It was not good: on the way to my new home, driving down the grey motorway, under the grey sky, listening to Black’s Wonderful Life (sample lyric: No need to run and hide // It’s a wonderful, wonderful life) it was all so bitterly ironic. Why the angst? The night before my girlfriend was round and we were trying to figure out what to do with ourselves – both off to uni, both wondering if we should stick or twist, having fraught sex and crying a lot. We decided to stay together but my life was feeling palpably unwonderful.

Jump forward to that night and (still don’t know how I ended up here) I’m sat on a table surrounded by people from the Christian Society in the hall’s bar. They tried to give me a cupcake but all I wanted was a snakebite, then another snakebite, then another snakebite, then a tequila, then something called a “bomber”, then shots. It was awful, I was awful.

A friend from home appeared, someone who I knew was going to the same uni as me but not someone I expected to see straight away (different halls). She was there and she was good looking and we were both really hammered and neither of us wanted to go to what was being billed as “The Pyjama Party”. It was raining outside and she lived far way so I asked her if she wanted to come back to my room and she did. We slept together and at one point she asked me, “What about your girlfriend” and I didn’t answer properly, mumbled something into her neck, carried on.


It was New Year’s Eve and I was 17. After five years of an all-boys’ school I was now in a mixed-sex sixth form and in a desperate attempt to prove I could talk to girls I accepted a relationship with the first girl to drunkenly kiss me at a party. It was hell, yet the one-two punch of her birthday and Christmas meant I didn’t have the heart to break up with her until January.

For NYE, we spent the night at a friend’s house party. Also in attendance, my best friend and his girlfriend (let’s call her Jane) who I’d had several almost-near awkward moments with before the two of them had got together. What can I say, we had chemistry.

At around 11pm, I left my girlfriend downstairs talking to people because Jane “had to talk”. What started as a conversation sat on my friend’s bed turned into a vigorous make-out session. People occasionally came into the room looking for things (an act I later learned which was orchestrated by her suspicious boyfriend) and each time we managed to pull ourselves apart as if nothing had happened, though probably with limited success.

As midnight drew near, we were both told we had to stop our private conversation and join everyone else downstairs for the countdown. I re-joined my unwitting girlfriend, smiled and saw in the new year with a kiss. Ten minutes after midnight, I was back making out with Jane (this time in the bathroom so we could lock the door). Her boyfriend eventually found out (her conscience made her tell him) but I don’t think my girlfriend ever did. A few weeks later I dumped her over MSN. I was a terrible boyfriend.


It was probably one of the worst things I ever did. I went to my boyfriend’s freshers week and slept with someone else. It was accidental, and sounds really slutty, but I was out of my mind drunk. Basically I was in upper sixth and my boyfriend was a first year, and for the last day of their freshers week they had to dress up in something that began with the same letter as the name of their halls. His halls began with an N, which I didn’t know until I got there so someone kindly lent me a nurse outfit (it gets worse). My boyfriend ended up getting so drunk that he was vomiting and had to be put to bed – when I went to go to bed, I couldn’t find my way back to his room. I got lost in the halls and ended up chatting to someone else instead, then flirting, then drunkenly sleeping with them. Afterwards I felt so guilty I told him straight away, but he was still pretty mad, especially as I couldn’t remember who it was exactly — until I saw them in the canteen the next day. It was hell, and it meant everyone knew he was the guy who’s girlfriend had cheated on him in a nurse outfit. For some reason, he stayed with me, but promptly slept with someone else on Valentine’s Day as revenge. All is fair in love and war, so I dumped him.


I haven’t done much I’ve really regretted but I can comfortably say cheating was the worst thing I’ve ever done. I’d been seeing this girl in the year below at uni. We were both keen to just call what we were “friends with benefits” but we were pretty much a couple. We’d hung out with our two groups of mates, gone out together a lot and always seemed to end up at each other’s halls. For the best part of a year we were essentially boyfriend and girlfriend until a night after exams. I’d been out with a group of mates from home when I saw one of my basically-girlfriend’s friends at the bar.

“One thing led to another” sounds like it was a drunken accident I didn’t expect. Being honest, we both wanted to hook up that night. If I could stop myself from going back to the wrong room and quietly silencing my phone as my girlfriend called, I would. Coming clean the next day was awful. She cried, told me she never wanted to see me again and sent me out the door. About six months passed before I heard from her and the air’s cleared now. The whole experience seems a bit cringe looking back. It wasn’t worth it – I’ve tried to think what led me to do it but I think it was just because I could. Maybe that’s the worst thing about what happened.


The last time I cheated on someone I was still at school and received a text from my boyfriend with a print screen from his boys’ grammar school rumour Facebook page, where they wrote rumours and stories about the girls’ school. One of them said I’d got off with a boy who had a girlfriend and he asked me if it was true.

It was. I mean, I didn’t sleep with anyone, it wasn’t that bad. But the way he asked me made me chuckle. I lied and told him no. I never got caught, although I was approached by the guy I’d cheated with, his girlfriend’s friends. They demanded to know if I’d got with him and I said no. I was like “oh, we were just chatting, classic rumour mill” — lies.

He never found out. I think he guessed though. Me and the guy always had a cheeky thing. Not like dating, but every single time we went out I used to get with him.


I was absolutely sure I’d broken up with my longterm girlfriend before I went on holiday, but something must have got lost in translation. As I boarded the plane I felt free of the shackles of an oppressive relationship. I was a peacock and finally I could fly. I got with quite a few girls and had a lot of sex with an Irish girl who practically branded me. But when I got back I bumped into her when we were all out with friends. After a heartfelt conversation, she said: “I guess this is it then.” I stood there, stunned. No, no this was it three fucking weeks ago. Don’t try it, nahuh. Evidently, she had lost her grasp on the English language during our break-up, that or she’d blocked it out, and thought we were still together. Not the worst cheating story, but God I feel guilty.
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