The only time I ever had a condom break was when a former gf was paranoid about geting pregnant and insisted on doubling up.
The lubricant in the condom idea works well and increases the sensation a lot (almost feels like au naturel) but if you have any degree of sensitivity to lubricant it can sting if the lubricant gets down your urethra.
One of my pet peeves is when SPs who are new to the biz and told horror stories about the clients insist on switching condoms betwen fellatio and intercourse. There was one lady that must have gone through four condoms while she tried to get the sequence right. LOL