Howard & Richard’s Squeeze Play

February 27, 2008
Photo: The Howard Stern Show

Howard discussed his obsession with masturbating to the Bree Olsen porn JD had given him, despite being grossed out by the weird parts, like when the male star spits into Bree’s ass. Richard came in to ask if Howard looks at his own penis when he finishes, but Howard said he did not, though he does squeeze his penis to make sure he gets the last drops out. Richard claimed he did the same thing – in addition to watching his penis so he can monitor his volume.