Woman here - I have initiated many, many kisses with guys in my time. It has always gone well, and they have always expressed feeling remasculated, not emasculated.
Also any guy that won't let you initiate is someone you should run from, no matter how much you like them.
There was only one time that I felt like I had to really orchestrate the kiss coming from the guy first, and that was a special situation. I made sure to put on some music that he thought was romantic, have some teasing conversation, get the mood going, put his arm around, and then look up at him - at which point he got his cue.
Guys also initiate with me, but if you think he's not going to go for it, you absolutely should.