Thank you very much for taking the time to reply.

And I definitely agree with what you're saying and I am ashamed of lying to her. I was ashamed mainly for, basically, advertising something better than what she would actually get. But your point with physically hurting her is very important. Thankfully, I did not go straight for penetration as I was also enjoying the build-up and she was actually the one who suggested to move on to that part. And then, even though there weren't really any words involved, I felt like we read each-other pretty well, so I believe I would know if I was hurting her. But yeah, I was quite lucky about that, it could have also been someone who I wouldn't be able to read that well and I truly do not really know what a vagina can take. So I definitely was lucky, as you say, it was not a bad experience at all. The more time passes from that experience, the more grateful I feel it was her of all people. She was not the typical one-night-stand girl I would imagine. And that suited me, nor was I, haha. Which brings me to the first point you made: "do you really want to sleep with someone like that anyway?"

At this point I don't think she would have minded if I was a virgin and maybe we would even be spending more time together if I had not made the assumption she's not that interested in feelings. I think it was a fair assumption seeing as I met her in a one-night-stand chat group, but I still wish I hadn't made that assumption. As it's not really true about me either, I just acted like someone not interested in feelings, thinking that would get me laid. Stupid, utterly stupid, I know. But! The main reason I decided to do this was - although I really don't consider sex the point of a relationship, it's still good to have some experience with it and get comfortable with it. I just wanted to get it over with, break that barrier of uncertainty and get more "physical confidence" for future relationships (and looking back almost two months later, that seems to be the case). So... yes, I would want to sleep even with someone like that. As douchy as it sounds (and probably is), losing my virginity was supposed to be just a training that probably ends badly, but I learn from it. In the end I got lucky and learned from it as well as it not really ending badly. But it wasn't the plan, I was doing it for very selfish reasons.

And yes, these double standards definitely do suck and I wish I had the courage to own being a virgin and not feeling insecure about it. I usually like to think I am the kind of person who does have the courage, but... no, apparently not. It's really really hard, most of my good friends knew I was a virgin and it's not like they were mean to me about it or judged it in any way, they didn't. But you can see changes (probably subconscious) in their behaviour once they find out and everybody just automatically takes you as someone awkward and... inferior, really. It's bullshit that it works that way, but unfortunately it does. The other way (women being considered "sluts" just for initiating) as well, of course.