That time when I [21F] cheated on my first boyfriend... And then broke up with him...

NSFWCheating

This is not something that I am proud of, but the memory came up when I was chatting with a Redditor, and people I have told really seemed to... Enjoy it when I tell them, so I thought I would post it here too. It has been a while since, and so I don't remember the exact details, but I hope you enjoy the read nonetheless 😇

By then, we'd been together for almost two years, and instead of resolving our arguments, we just swept them under the rug. I had questioned why I was dating him on multiple occasions, and in hindsight, I think it was simply attachment and a sense of familiarity because my needs were seriously not met 😢

And during the week of my 21st birthday, we fought again. went to my part-time shift with swollen eyes because I was crying the night before. During my shift, a colleague I was close to noticed and asked me if I had fought with my boyfriend again, to which I replied yes, and vented to him about what happened this time. Fast forward to the day of my birthday, my boyfriend and I still hadn't talk things out, and he didn't even wish me a happy birthday. Well... He eventually did... But by then it was a bit too late... Because I was out with said colleague... In a hotel room... 😔

My colleague was checking in on me the night before, and because we were already texting, he wished me a happy birthday as soon as the clock struck midnight. And when he asked if I had any plans with my boyfriend, I told him we were still not talking to each other. So, he offered to take me out, so I wouldn’t end up crying alone in my room on my birthday. And I agreed.

I thought we were just going to go out for lunch, but we ended up spending the whole day together 🙃 And when things got really flirty towards the late afternoon, bells should be ringing, but they weren't, or I simply ignored it. It was the first time I felt that kind of attention from someone in a while and it felt nice...

At dinner, I was by no means drunk, but after having a little to drink, I really started opening up and even started flirting back 🥲 I even shared my sexual frustrations with him (that my boyfriend can't even last a minute in me 😶) when he was walking me to the train station. And when he told me something along the lines of him being able to do better, I challenged him to prove it... 😳

And so... We went to a hotel. I remember checking my phone as we took the elevator up to our room, hoping that my boyfriend had sent me a message, but there was nothing. And so... I went ahead and let my colleague fuck me... And I know that cheating is wrong, but my god... He was so much better than my boyfriend 🫣 He knew how to tease me, how to make me crave for more, how to make me feel good 🫠 And when he fucked me... Fuck was he good 🫠 Between his fingers, his mouth, and his cock, I had so many orgasms that night 💦

It was only later, when I checked my phone again, that I saw my boyfriend’s message wishing me a happy birthday. But by then, it was already nearing midnight 😒 And his girlfriend is in a hotel bed, exhausted, covered in sweat, and her pussy filled with her colleague's cum... And that was when I decided to end things with my boyfriend... Because even if we managed to work through things, which we don't ever, I will never be able to go back to his cock... 🫣

I never did come clean to him about this incident though... And I do feel bad about it 😔

P.S. My current boyfriend already knows about this. He got so hard when I was telling him 🤭

Posted Jul 11, 2026, 1:36 PM UTC

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