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When your male modesty is so long that you can reach the bottom of a pint glass……. Typically, we are talking about when flaccid, although whilst erect, it is still impressive; after all, the average length of a fully erect boner is [approximately] 5.1 to 5.5 inches (13–14 cm) and a pint glass is roughly 6 inches tall! Thus, claiming to "touch the bottom" places you in the top tier of length, making it a significant claim down the pub or in [the locker room] [with the boys].
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