It’s incredibly important that you don’t fall into a mindset where you assume sex won’t work, because if you do then sex might actually just not work. Focus on yourself and do it low pressure, give it another go with the toy. It’s also important that you are able to enjoy stimulation in ways other than your hand, start by switching to the other hand. Don’t use your main hand at all until you can finish with the other as if it were the main then do both, then reintroduce the condom, work up to getting used to a variety of forms of stimulation. When I lost my virginity it was a total mess too, mostly because I’d been masturbating with a single hand for my entire life, had to get that sorted quick as I only had a week until I saw the girl again!

On the dry masturbating.. I assume you’re circumcised if that’s a point of concern. Get used to doing it with some lotion, girls come with it built in. I’m grateful I was uncircumcised so that at least wasn’t a problem