I am sure this has been asked before but I hope to get some useful input based on my specific situation..
Simply put, me and my girl are having some trouble with sex.
To give some context, we only had around 5 sexual encounters with the last 2 being close to having sex. On the one before the last one, she said she was not ready, and on the last one we actually tried to go for it.
We are having all our sexual activities in the car, and the last time we met we even tried to put it in without a condom, it was just the head but any more was extremely painful for her. I ate her out for a good while before that, she again didn't finish but she said she enjoyed it and that again she doesn't really know how to finish. I tried licking, sucking, and fingering, and combinations for each.
In general, she has only had it a handful of times, is very tight, and has never actually managed to finish, which causes some anxiety in my opinion.
She expressed that although she really wants to have it she is having some mental blockers like the fact that she is insecure about being unable to finish and feeling that her genitals smell, when I have reassured her many times that this is not the case and I am really turned on by her. She genuinely is very hot and honestly does not smell almost at all. This worry was because the first time I ate her out was after the gym and she knew that there was a certain smell to it, which admittedly I was honest about after the fact, but this time was genuinely like 10% of that.
Another issue is my size which doesn't help both in terms of penetration but also in actually having a comfortable erection while wearing a condom. So I'd like some advice on that too, I'm not experienced on that front either.
My current thoughts are to get lube which she agreed with, and figuring out what condoms to buy so that I am also comfortable.
I do not want to book a hotel or go on like a small 2-day holiday for example just so we can have a room, because I feel like that might put too much pressure on her to actually do it and not let it happen naturally. We have only started dating for 2 weeks now so it is still super early and she said that she never moves this quick when talking to/dating someone (not that she has had much experience anyway but still), so this is another factor in my mind, and almost makes me want to just ride with it for now and let things happen more naturally. I do want to be adequately prepared though so I wanna hear thoughts on how best to do that, and what specific products I should buy. Eg I heard that water-based lube might work well for this but again, I am not experienced so I couldnt know.
Thanks in advance and sorry for the long post, I am just a bit anxious and want her to have a good experience as she hasn't really had one before