But recently my girlfriend tried masturbating me, and beforehand, just making out, I secreted a lot of "pre-cum." I had no actual orgasm. Is it possible that all the "pre-cum" is keeping me from ejaculating, or am I just abnormal because I can't have an orgasm without masturbating myself?
Semen and Cowper's gland secretion are two different things, though both share certain ingredients (including sperm cells). It's very unlikely for a guy to secrete his semen in this way without ejaculating. My guess is that you just aren't used to reaching orgasm with a partner – for some guys, doing so is a big step to take and requires several tries. I'm sure you'll get the hang of it eventually. In any case, don't get hung up about it – sexual play should be about relaxing and sharing, not suffering from anxiety and self-doubt.
Do you find yourself masturbating more often during some seasons than others? Why?
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