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Hey /adv/. I've got a good one for you today.

Last night I was with a girl and going to town with her on the foreplay (she literally squirted on me) and by the time she said "I want you" I pulled out my condom, but after a bunch of time fiddling with it I could barely get it on, and when I did I couldn't get it up again and we stopped, much to my embarrassment.

This happened the first time I had sex too. I wasn't that hard when I put it in and then it got soft while we were fucking.

How can I go about fixing this? I'm really worried it might be a recurring problem.
Some aspects that could affect it:
-I think I'm a chronic masturbator, and may be addicted to it somewhat. Some days I do it 2-3 times, and it's often almost every day.
-I have a bit of social anxiety and depression
-I think I psyched myself out a lot. I was embarrassed that I couldn't get the condom on, and worried that I wouldn't be able to get hard, even though I tried to convince myself that I was about to fuck some hot girl if I could just get hard again
-Parks and Rec was playing loudly on the TV, and might have distracted me

Any lifestyle tips, or in-the-moment tips you could give me? I know the typical "don't psych yourself out", but that's easier said than done.