The sense is that if a fruit is squeezed very strongly the pips would shoot out, perhaps at least figuratively, making a “squeaking” sound as they fly across the room. To “squeeze (someone) until the pips squeak,” meaning to exert heavy pressure on someone in order to extract money, information or simply obedience, is definitely a reference to the “pips” in a fruit. "We will get out of her all you can squeeze out of a lemon and a bit more," the penitent shouted, "I will squeeze her until you can hear the pips squeak" his policy was to take every bit of property belonging to Germans in neutral and Allied countries, and all her gold and silver and her jewels, and the contents of her picture-galleries and libraries, to sell the proceeds for the Allies' benefit.As suggested by the Word Detective pips refers to fruits seeds: An earlier speech in which, in a moment of injudicious candour, he had cast doubts on the possibility of extracting from Germany the whole cost of the war had been the object of serious suspicion, and he had therefore a reputation to regain. The grossest spectacle was provided by Sir Eric Geddes in the Guildhall at Cambridge. To squeeze (something) until the pips squeak "exact the maximum from" is attested by 1918, from pip (n.1).
Pip and Squeak (and later Wilfred), the beloved English comic strip animals, debuted May 1919 in the children's section of the Daily Mirror. In World War I it was the soldier's slang name for a small German shell "which makes both a pip and a squeak when it comes over the trenches". Also pip-squeak, contemptuous name for an insignificant person, 1910, from the trivial noise a young or weak creature makes.
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