Hey all, I never post here so here's some background;
I'm 6'6" man, 28yo, currently 339, started at 395. I think I'd have visible abs at 265, I've never really been under 280 since I quit growing... but I look pretty trim at 280. I've always been overweight on some level, but it just got out of control after a bad motorcycle wreck a couple of years ago. Laid up for a month, lost a lot of muscle, metabolism went to crap, all that. Add a hard job, and plenty of disposable income to spend on eating out. Pow... almost hit 400lbs (395+, once the scale starts saying 'error' at 330, you just keep assuming you're only a little above 330).
Decided it was time to do something about it, so...
I spent 6 months bulking up. I lifted weights 4x per week, ate whatever I wanted as long as 40% of my calories were coming from protein. Drank milk, protein shakes, etc. My strength and arm size increased like crazy, my weight stayed this same. Good sign. I also was doing some cardio; hiking, elliptical machine, sports, etc.
Once I felt like I had enough muscles to get started, I began my diet (October 09). I didn't keep a food journal, but I did keep a weight loss journal, weighing in every saturday.
My diet strategy is sort of a modified low carb diet where I also carefully pay attention to fat and calorie intake. Balancing my macronutrients this way, I can decide each week what my pain threshold is for that week. Sometimes I chose to lose 1 pound, sometimes I choose to lose 14 (that's like a normal person losing 6 pounds, again, I'm 6'6" and over 300). I also don't do a ton of hard excercise while I'm doing this diet because it can be pretty intensive. Just going for walks and occasional weights/cardio.
Here are the results over the first 5 months - (lost 55lbs) 
I plan on losing another 75 for a grand total of 130 lost. Next major milestone is 330lbs. It is both the half-way mark, and my fattest weight while I was in college. In my experience, getting down to 330 makes me look less-bad, but anything below 330 makes me look more-good.
Once I get down to my desired wieght and bf%, the plan is to slowly transition to a more traditional 5 meals a day program eating healthy foods (whole grains, complex carbs, lean protein, suppliments, nuts, etc) calculating my caloric needs and carefuly tracking my weight and calorie intake... all while making sure to hit the gym. This process is about getting control of my body and my life, not just getting my weight down.
Before and during pictures, and info about my strategy.
