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Agree and use the technique you mention of gripping the underside of the silicone ring with one hand (finger/thumb) and using the other hand to pull the skin at the base of the shaft (near the ball sack) to retract the excess skin of the frenulum that was remaining between the silicone ring and glans… very effective to draw the skin back inside the inner wear sheath.
Another very effective method I have been using in particular with the longer ES (Extension Sheath) version of Stealth (no ball band) is to first put the thin spandex sleeve half way down the shaft and then fold the base of the inner wear sheath to easily thread the spandex sleeve thru it. Then position the glans ( covered by the spandex sleeve) into the folded opening of the inner wear sheath and unfold to get it started over the shaft. Pull the base if the sheath into position and remove the spandex sleeve which effectively pulls the glans past the silicone ring to be secured behind the coronal ridge.
This method keeps the silicone ring from getting stretched out too much with insertion of the fingers and thumb.