Could be a couple of things. It may be nerves or "performance anxiety" which happens to alot of us early in our sexuality or when we're with something new or really want things to work well. It may also be that your penis is "trained" to respond to your masturbation style...grip, speed, technique etc. Try as we might, we simply can't create a vagina for ourselves through masturbation. You know that it works because it does...for you. Also, our penis is very much controlled by our "head"...unfortunately when something like this happens, our fear is that it will continue to happen and that makes this worse. You may try a couple of things...stop masturbating for a few days before you attempt things again. Change your masturbation habits by varying things, speed, grip, technique...add lube if you don't use it already and see if that helps. And next time you have sex, forget about past "failures" and focus on the pleasure, be patient and keep trying. Most of all, don't be embarassed, you aren't the first guy to have to deal with this and you won't be the last! Hope this helps!
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Teenage impotence? 
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