It is possible to over think anything, sometimes you need to JUST DO IT. That is probably bad advice, but just be sure that you are prepared for all of the possible results of your actions. If you can handle the worst thing that could possibly happen and the possible benefit of the action is worth if for you, then go for it. In this case, is the orgasm worth it? Part of sex for everyone is putting yourself out there with the possibility of rejection. Is the relationship, evening, and orgasm worth the risk.