Tip :  attach a string and a safety pin to keep from loosing the O-ring.
Just attach the safety pin to your pants or under ware and you will be safe from loosing your rings.

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If you choose to use O-rings to retain your skin when sleeping just keep in mind of the possibility when getting nocturnal erections that in O-ring could cause a problem if the penis slides through the O-ring as it becomes erect.
This can happen if the O-ring is too big.
  7/8 th inch ID (22 mm ) , 3/4 inch ID ( 19mm )  and  5/8 (16 mm )
Three sizes that work well. To improve the grip greatly wash with soap and water or at least water when you take them on and off.
Stacking is the use of multiple O-rings.  Some guys would use different sizes like I am showing here.

I tried stacking when I first started to restore and could not do it. I used black O-rings back then and these Silicone O-rings (red) are much better with grip then black standard O-rings.
Wash O-rings often with soap and water to remove skin oils. They should feel a little tacky after they are washed and dry. If it slips off,  give it a wash.
most common size used is 3/4
I do not recommend sleeping while wearing them.. what you do is your business.
I am only showing this as a demonstration of the "O-ring Stacking method" This was a method many men used to restore years ago.
One single O-ring was what I used to keep my skin over the glans when I was not restoring.
Caution! Restoring too aggressively can lead to injuries such as skin tears and bruising or possible other damaging injuries that I am un aware of.  Always use your own judgment on how you choose to restore. Pain is not part of restoring. The information on this web site is to show how I personally choose to restore and is not intended as instructions or medical advice on how everyone should restore. What you choose to do with this information you do at your own risk.
  An important note, when it comes to retaining and sleeping. This is something that every individual will have to make his or her own decision on. What I will tell everyone is that if you are thinking of using something when you are sleeping please test this out during the day while you are awake. You will also more then likely experience nocturnal erections. This will put more pressure on the skin when you are using restoring or retaining methods.

See how long you can wear what ever it is you plan on wearing at night during the day to see if it's going to bother you after a long duration of time ( like 8 hours ).  I never advise using anything when sleeping. Always Use your own judgment.

Restoring men have used O-rings to retain the skin over the glans when not restoring. I have found that Red silicone O-rings hang on better then Black O-rings.
I found O-rings to be very helpful for keeping the skin over the glans. The down side is they can fall off when there is not a lot of skin to work with.
At the time I used these my only other option was tape.. and that residue was not fun. so Orings became my retainer for awhile.