I know what you mean - my first wine, the must was so thick the hydrometer wouldn't even sink so I couldn't get a reading. Still, I am fairly certain that it is around 17% - it's definitely got a lot more kick than a 14% wine that I am used too, and the yeast has tolerance of 18%. Actually, my hydrometer doesn't give a proper reading if the thief is not completely full, although the hydromer will float in the thief even when half full. Make sure your thief is almost completely full when taking measurements.
I've studied the alcohol math a bit now, but I'm still a newbie. It really isn't that difficult, though. First thing to decide is how strong you want your wine to be. Second thing is to use a yeast that has a little bit higher tolerence than your decision. Third thing to figure out is the gravity where your yeast will finish, given correct conditions. From there, you can do the simple math and calculate your starting gravity - then just add sugar until you reach that point.
For example, if you want a 14% wine then you can't generally use bread yeast because it only has a tolerance of 11-12%. Bread yeast can work quite fine for lower alcohol concoctions, though - we have used it and the taste was still quite amazing.
Another thing to keep in mind is the temperature range in which your yeast is happy. If your fermentation area is 25 celcius, you can not work with many yeasts intended for producing lager bier but a champagne yeast (which is also technically lager) will work just fine in these temps.
If you want a 14% wine, in my opinion you are missing about 4 lbs of sugar in your must. Hopefully someone experienced will correct me if I am wrong.