I have TMJ, its a jaw disorder. So bj's were always very painful for me. In my last relationship, we were playing with ice.....I ended up doing it with the ice in the my mouth and he loved it, and it numbed my jaw. I also wanted to learn how to do it properly, so I searched on ivillage.com (no joke) "how to give a good bj". I never liked doing it, but did because he liked it. The gagging thing......it's really hard to work around. Only "take in" what you can....if that makes sense.

On another note......you say you tried for the first time last with "a guy". Is this guy your boyfriend? Just be careful, and thats all I'll say on that.