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which technique are you using to put the Innerwear on with? Are you insuring the fingers to clamp onto the glans to pull it thru the sheath or the spandex sleeve to thread the sleeve and sliding it onto the shaft?
As rick mentions, if you are wearing the sleeve inside out with no folds of the baseband, the silicone ring will easily roll under thereby allowing the glans to slip past and retract into the sleeve.