I Finally Lost My Virginity After 30, But Am I The Asshole For Not Telling Him?
Anonymous Dirty Menace #812 · General
So yeah, after being single for a while post-breakup, I decided to go on some online dating sites and just see where things led. Met this guy, let's call him Jake, who seemed pretty chill. We had our first date at this nice little Italian place downtown. He was cute and funny, we hit it off instantly. A few dates later, he suggested we skip the usual after-date drinks and head back to his place. I didn’t want to seem too eager or pushy about sex, I'm new to all this again post-relationship, but also, I was so damn ready for some action. We had this incredible chemistry. We ended up at Jake’s apartment and he started getting a bit more physical than before, but not overtly demanding anything. And then it hit me: we hadn't even discussed protection yet! And here we were practically on the edge of doing it without talking about it first. I paused everything, told him to grab a condom from his drawer. He did, we talked briefly about preferences, nothing too deep at this point, just some basic stuff. It was then that Jake mentioned he’s actually still a virgin too, in his mid-30s like me. And right there and then, for the first time since I was 18, I lost my virginity to someone who wasn’t technically a virgin themselves. It felt weird but also liberating at the same time. The act itself... oh god, it was intense in every possible way, both exhilaratingly painful and so unbelievably pleasurable. Jake was incredibly gentle with me, giving me space when I needed it, being attentive to my needs and adjusting as we went along. Afterward, he held me close, both of us just a bit shaken by the whole experience. But now here comes the kicker: I’m really starting to think about whether this is fair or right for him. Maybe I should’ve been upfront from the get-go that I was no longer technically a virgin? But it feels like such an awkward thing to bring up mid-foreplay, you know? So my question is... am I being an asshole by not telling him this before we had sex? Is there something unethical about me leading with the idea that he’s ‘the first one’ for both of us when I actually have some experience under my belt already? I'm really unsure now if honesty is still necessary at this point. We’ve been seeing each other regularly since then, but it just feels like a big elephant in the room that keeps haunting me. What do you all think? Am I overthinking this way too much?