This is a TLDR of my thoughts since I realise reading 2000 words about the problems of a stranger doesn't seem so appealing.

So after heavy thought I've come to the conclusion that I'm having the problem stated in the title and the roots of it lie in insecurity, fear of becoming rejected. They started when I was 14 when I was lying in bed with a girl and was "scared" to go all the way, I wasn't good enough. And just those thoughts have followed me up until now that I'm 21 which is another source of insecurity.

At the moment I'm on really good terms with two girls that I get along with really well but both are in a relationship that I don't think they enjoy. In fear of coming off as rude I'm not touching that, should I? Because deep down I want to.

Do I just say fuck it and go for it the next time I have the opportunity?