Yeah you were definitely nervous and not being able to get hard is a common occurrence for many guys. I’ve heard the story so many times but oddly enough it didn’t happen to me. So she was ridding you for a bit but you didn’t get hard or cum, understandable. Your dick was wet either from your precum, sweat from the condom or maybe it’s lubrication. So you took a break for about two hours and went again. Without a condom this time. Were you hard then? I’m assuming that you got tired from the constant pumping. Sex is a vigorous workout. Did you feel anything? I’m surprised that you went 20 minutes. Then she jerked you off. Yeah your dick was wet from her pussy.
The next time you have sex it should be much better. If it does happen again when your going to have sex, make sure to be fully hard before. Either she should suck you to get you fully hard or use her hand, if you even have an issue with it next time.
As for getting her pregnant there is a small chance that your precum could get her pregnant but the odds are very low. Since you used a condom and I’m assuming she’s not on any birth control method. Just to be safe she should get checked. Also next time it’s a good idea to have more than one condom. When you have sex be sure to always use a condom unless you KNOW she is on birth control and that neither of you are sleeping with anybody else.
LOL to jerking off five times earlier in the day. Also it being late could be another reason for not getting fully hard.
Search google for “morning after pill”