I think that would be a deal breaker for me. It would be one thing if these were longstanding friendships, but forming new friendships with strippers and women who send him nudes is a bit much. Perhaps there is a cultural difference, but most girlfriends in the US would be angry with a boyfriend who did that stuff. I don't think you are abnormal for being upset that he is sleeping in the same bed as someone else especially when you know that he has cheated on other girlfriends in the past.