OK. I know have more confidence to pull the foreskin back while flaccid.
1. Should I use some kind of lubricant? (Preferably nothing I would have to rub in as the glans has been exposed twice at most so it will still be very sensitive and I do not want to hurt myself.)
2. Should I pull the foreskin up and out the sides a bit before pulling down?
3. When I get the foreskin almost past the glans, the glans itself seems to swell. I am worried that when I pull the skin past it that the skin will not go back over. (That would scare the hell out of me and I would probably never try again.)
umm, should talk to a doctor...I think I had a similar problem though my solution was just to get circumcised. If you don't want to go that route though
1) probably, lube on glans doesn't hurt, it feels good but would probably give you an erection
2) I guess it will help if you try to stretch it beforehand
3) If you get an erection it might get stuck but should go back to normal when the erection goes away. Also if it does get stuck back it shouldn't be a big deal as long as it doesn't hurt, be like being circumcised but without the painful surgery part