Shawn, like others have said, your face is quite soft already however, you should be prepared for that to change if you aim to loose a lot of weight. Your cheeks will thin down a lot I'd say. Hrt will bring the softness back to your face in a more "female" pattern. Good luck with your weight loss programme. When I wanted to loose a little weight last year, I went on a calorie restriction diet, and walked a lot. I tried to stay under 700 calories a day. It worked well and quite quickly although I'm sure everyone looses weight differently.