sex

So I got some questions about sex.
1.I'm 19 and he is 21. We were both virgin when we started having sex. So I know people say that sex shouldn't be hurt. But I did felt a bit hurt the 1st and 2nd time we did (we only have sex twice), we did used condom for both time. It was not much, just a little pain and was bearable. But we were a bit nervous so we didn't feel being turned on that much. Maybe that the reason? Should it be something to be concerned? I wasn't bleed or anything after that.

2. So on the 9th day of my cycle (my cycles are pretty stable, 28-30 days), which is after 2 days I was completely done with my period, we were fooling around. He masturbated himself and cm on my chest. He was laying on me and after about 5 minutes, we both got up to wipe ourselves, I noticed that his semen became clear and more liquid at the time. Is that normal to guys? And what does that mean? Does that mean that sperms are dying? Because we only dry humped with undies on and when he ejaculated on me, i still got my undies. It means it's impossible for me to get pregnant right?
2. Then on my 11th day of the cycle, we did dry humped again, but this time he rubbed his tip around my anal in about 2 minutes. He was dried at the time (I did checked on that too when he was rubbing). I don't think this could lead to a pregnancy either, but would it be a chance IF he was on pre-cm at the time? He did peed in the morning.
3. So sometimes he masturbated and then touched me, around my clitoris, not inside vagina., and his hand was dry. But what IF he got some of his own fluid when touching me? Is there any chance of pregnancy?
Today is the 18th day of my cycle and I don't see any signed of ovulating (I usually see I got more discharge, and it's clear, mucous like yolk around the day 14th-15th). So I'm a bit worry, I don't know if I'm in any chance of pregnancy right now. He told me many times and confirmed to me that I can't get pregnant or it's impossible from whatever we did. But I heard some myths. So I brings out some cases for you if it was like that? I want to hear your opinion, and I'm happy to gain more knowledge.
Looking forward for your reply. Thank you so much.

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• Sex 101