So after two months of confidence boosting and trying to get a better attitude towards this whole dating thing, I've finally got somewhere and obviously I'm pretty fucking happy about it ;)

May as well give the story... I'm not really a PUA or all that interested in it, but this girl who was introduced to me through a friend was interested in me so I went on a couple of dates with her. It feels like cheating a bit because I didn't really pick her up, in fact I'd say that when I first met her I got zero IOIs (at least that I recognized, this is before I started reading seddit) and didn't think anything about her, but a few months later she apparently had been thinking about me and sent me an email asking if I wanted to go for a drink.

Well, she's actually pretty hot so even though I wasn't sure if there was chemistry I was like "why the fuck not" and said yes. I think I had quite a good "outcome independent" attitude through the whole thing because I didn't really mind whether it lead anywhere -- I didn't initially have a feeling of whether I wanted her or not, despite her being pretty hot, so I was find with either outcome. We just met up for drinks, nothing special, but got along great on the first date, so I found myself interested in a second one. At the end of the night I didn't try anything, thinking it'd be best to play it cool (besides I still wasn't sure where I wanted to go with this) so after agreeing to meet again the next week I kissed her on the cheek and said good night and that was that. She seemed a bit surprised that I didn't try to get more, but I wanted leave her wanting me, not to beg her for some action right there and then.

She continued to text me on the weekend a few days later and I gave her short, funny answers, not wanting to enter into dialog until I saw her next time. When it came to our next date we bought a bottle of wine and drank it next to the river. (She brought it!) It was pretty clear she was into me but I admit I was having trouble breaking the obvious sexual tension (ie escalating), but the more we talked and got along well, I started to promise myself I'd try something before the end of the night, and eventually in a lull in the conversation I was just like "this is ridiculous" and I touched her hair and told her I'm into her and kissed her.

The response was fantastic, she just started making out with me hardcore and then after another drink it was clear that she wanted to continue so I was like, "the night doesn't have to end here."

At this point I pulled a bit of a trick I'm kind of proud of... the subway was closing soon and I reminded her of it but she wasn't really paying attention, so we started walking back to the subway and instead of rushing for it, we stopped and kissed several times. By the time we got to the subway, it was a few minutes too late, and it was closed. So I was like, "well we've got to take a taxi now, want to come to my place or go to yours?"

She couldn't decide, but somehow started flagging down a taxi before we'd even decided what to do ;) So when the taxi pulled up I just said, "okay we're going to your place," and she was like "yeah okay..." Basically I exuded a lot of confidence and just told her what we were doing next and she was fine to go along with it. She was clearly willing, but just didn't know how to make the decision so I made it for her. I'm kind of doubly proud of how well this went since the whole date, which involved a lot of conversation, was entirely in my second language (french).

As soon as we got to her place I grabbed her and magically her dress came off :) the rest of the night was pretty awesome, needless to say. We'll see each other again next week since she's away for a few days.

Here's where I need some advice: this is actually my first sexual partner since breaking up with a long-term girlfriend about 6 months ago, and despite having an amazing night it wasn't without some mechanical difficulties. In short, I'm completely not used to using condoms. I was with the same girl for 10 years and haven't used one in about that long. I'm not really into taking risks with VD so now that I'm single I definitely want to use condoms, but I can't even explain how weird and unsatisfying it felt personally. To admit it, I couldn't even finish. In her words, it was like having sex with a plastic bag. (We did lots of other stuff and she seemed satisfied, thankfully. And I did fuck her, it's just that I couldn't feel it very much and weirdly lost my erection, which I just had to laugh at since I was incredibly turned on and that's never happened to me before.)

Tell me, how can I make condom sex better? Is it a matter of finding the right size? Are some brands better than others? How can I find the right condom for me? It's not like I'm going to buy several boxes and try them all.. of course I did tell her we'll have to practice a lot. :)

TL;DR: she was already pretty much DTF, at least by the second date. I took the hint, but played it cool, took a lead role in the logistics, and made it happen. Sometimes the classic way is the best ;)

EDIT really cool, thanks for the condom tips! I'll try to find the right size, lol I had no idea..