Yes. Always pull your foreskin completely back from the glans. If you don't pulll your foreskin back before shoving your glans in, it will slip. This is the side benefit to have the bulk wrap at the bottom of the glans, because it helps to pull the skin back to prevent slippage during moisture build up, or when your penile shaft shrinks a bit.
By the way, your glans does expand slightly under pressure, like it or not. This is why we don't over expand our glans before turning the knob. The 4.5inHg inside the penis will turn into 8inHg in no time at all even with just 3/4 of a turn on the knob.
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