Thanks for your replies. I just wanted to see if others had experienced the same problem and whether they were able to overcome it.
jdm, one thing I'm worried about is paraphimosis when keeping the foreskin retracted. What are your thoughts on this?
@Brownuncut: You didn't mention this in your original post. Have you experienced any problems that would lead you to think you might be at risk for a paraphimosis? Do you currently have a phimosis?
As a general rule, if you have no trouble retracting the foreskin fully, and no trouble pushing it back forward, then paraphimosis is not going to happen from keeping it retracted. You may get some minor, occasional swelling of the foreskin until it adapts to the new position and exposure, but this shouldn't be a problem unless your foreskin is unusually tight. Minor swelling is best dealt with by taking a break, and returning the foreskin to the forward position for a while, as recommended by Soundsgreat87.
If you have a tight phimotic ring (the puckered opening at the tip of the foreskin), it may actually help you keep the foreskin retracted in that it may sort of snap into place behind the glans, and stay there without the aid of any devices. I had that early on, but it stretched out fairly quickly to the point where it would no longer stay back on its own. But paraphimosis is something different. It's when your phimotic ring is so extremely small, and non-elastic (phimosis), that it gets stuck behind the glans, and cannot be pushed back over the glans (paraphimosis). In this case, the first thing medical professionals do is to try and squeeze the blood out of the glans to make it smaller, and bring the foreskin back over it (you can try this yourself). They may also use ice and/or drugs to reduce the swelling. Obviously if it was possible to pull the foreskin back behind the glans in the first place, then under the same conditions, it should be possible to return it to the forward position. The problem comes in when blood return from the glans is restricted so much that it swells up to the point where it can't go through the opening anymore. Only if they can't bring the foreskin back over the glans is surgery strictly necessary. But often a circumcision will still be advised/pushed, even if it's not really required. Don't believe the hype.
I'm not a doctor, so this is not medical advice, but I don't think you will ever get a true paraphimosis unless you have a true phimosis. And if you do, you shouldn't be trying to pull your foreskin behind the glans (yet). You should be focusing on expanding the phimotic ring to the point where you can pull the foreskin back without difficulty or danger. This can usually be achieved through the use of various stretching techniques, and steroid creams. There has been some good discussion about this in these forums. Once you reach that point, then you can start working on perpetual retraction as safely as anyone else.