The USS Lollipop was the name of a fictional starship on which Commander William T. Riker claimed to serve in a ruse he devised in 2364.
During a visit to Minos in 2364, Riker was approached by a holographic duplicate of Captain Paul Rice of the USS Drake, who asked about Riker's ship, which Rice believed (correctly) to be the USS Enterprise-D.
Riker responded that Rice was incorrect, and added, "the name of my ship is the Lollipop." When Rice did not recognize the name, Riker told him, "It's just been commissioned. It's a good ship." Rice pressed on, undeterred and taking this obviously absurd answer at face value, further asking Riker, "What is the armament on the Lollipop?" At that point, Riker, annoyed with the ruse, responded only with the unqualified quantities "Ten" and then "Six", which the hologram was unable to comprehend.
Once Riker proved to the hologram that it was not, in fact, Rice, it reverted into the form of an Echo Papa 607 system drone, before firing on Riker, encasing him in an "energy field". (TNG: "The Arsenal of Freedom")