I started retracting mine because i wanted to be cut. For 11 years i wore it back all the time, occasionally i wore it covered. Sometimes it would roll forwards and stay there for a bit, sometimes i would get an erection and it would roll back then stay there. Seems it could go either way...
after 11 years (28yrs old) i just got cut as that was what i'd wanted in the first place and was never satisfied with just being retracted. I prefer it cut, although i would probably have been happy with a natural penis if the foreskin had been short enough for the glans to be permanently bare, as is the case with about 10% of uncut guys.