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This term refers to an unusual manual technique to produce a male orgasm. It is generally associated with a realtionship where the male partner is submissive.

The male partner adopts a position "on all fours". The female partner sits or kneels behind him, and reaches between his legs and pulling his penis into an essentially vertical position, pointing downwards. She then uses her hand or hands to masturbate him, 'milking' his penis until orgasm and ejaculation are achieved.

The term dates back to the era when cows were milked by hand, the dairygirl sitting on a three legged stool and squezing and "stripping" the teats so that milk was directed into a bucket or 'pail'. The practice of that technique made her a very desirable partner in an intimate relationship or marriage.
"No sex this week for you David, but you can have a Dairygirl's Squeeze on Saturday."
by Katie4eyes January 19, 2018
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