What is Gertrude Lollipop?
1.
When seducing an older woman, particularly with dentures, have her take out the false teeth before giving you a blowjob, creating an enjoyable slip-n-slide experience for your cock.
Dude Elinore Rosenstein gives the best Gertrude lollipops and she pays me for it too!
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Issuing an invitation which the other person can't accept, in the hope that you get credit for asking but don't have to follow..
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Said as if one word, it means "Do you understand what I mean?" but during the peak of its use it ended up midway through many ..