What can I do or say that will make him initiate a kiss/make-out? Also, we both know we like each other mutually.
(He knows of times in the past where guys have forced me to fool around with them sexually, which kind of made me more guarded in that respect.)
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I'd say try to initiate touching (nothing sexual, just arm around him, holding hands, etc). And make a lot of solid eye contact and look at his lips, he'll get the idea.
I'm shy and even though I recognized my girlfriend doing the above I still couldn't work up the courage to kiss her, so one day when we were watching a movie she randomly turns to me and says, "Are you ever going to kiss me?" And I knew it was now or never and just went for it. So I guess you could try pulling something like that too.0