preventing pregnancy question

I am 20 and my boyfriend and I have sex quite a bit - whenever we get the chance. I am on the pill and take it perfectly, and he also uses condoms. I have even asked him to pull out with the condom on at times as well. I find myself overthinking a lot and my anxiety convinced myself that somehow the pill isn’t working - that somehow, the condom broke as well (even tho I check almost every time under the faucet with water to see if there are any holes.. which there never had been). I guess what I am asking here is for some reassurance that I am okay and that I am overthinking....

I want to skip my period next week with my pills as I am going on vacation but I like to have my withdrawal bleed to reassure me I’m not pregnant. I should be ok tho and have nothing to worry about, right?