Can skin ever un-stretch on its own?

Thank you! I started seeing a health psychologist and have started trying to think of food as fuel for my body, not a way to cope with stress or boredom. I track everything I eat with MyFitnessPal, but I try not to obsess over it too much. I've tried to stop beating myself when I fell off the wagon (and stopped "slashing the other 3 tires" every day I "got a flat"). I started eating vegetables for literally the first time in my life. Perhaps most importantly, I started playing Dance Dance Revolution again, bought a bike that I ride regularly (living in Portland sure makes that easier than when I was in the Midwest), and have generally upped my activity level quite a bit.

I should mention that this is the third time in my life I've lost > 70 lbs, and every time I think I do it a little "better" than the last time, but the yoyo habit is already strong with me. When I was 18, I lost 80 lbs in 3 months on a shake diet, then started college and gained 100. At 23 when I was diagnosed with DMII, I calorie restricted to the point of misery, lost 80 lbs, then plateaued and lost motivation, gaining back another 100. People are asking me now why I still plan on surgery, and the fact is, I know I can lose weight; I've just never been able to keep it off. Also, after multiple failures in the past, the real reason I got the motivation to try again was because I knew I'd eventually have that extra tool at my disposal.

I'm glad that people are being honest about lose skin. It seemed that most people thought that only people who lose 100s of lbs have loose skin problems. 

Chipmans post is really good, although I find that cocoa butter does help tighten up the skin slowly. I've heard others talk about moisturizers in general helping to tighten up the skin. 

I've noticed from fat loss that.. when you start losing fat your skin hangs looser and rolls more so without a shirt on you actually look worse****il your skin tightens up). If you gain a little fat and it tightens up your skin, you actually look better shirtless.