Milkshake or milkshakes refers to a women's breasts, aka titties, boobs, tatas, boobies, tits, chesticles, knockers, funbags etc.
They are capable of producing milk while a woman is breastfeeding, and are known to "shake" or bounce.
Hence Milk+shake
In "Beauty Shop" with Queen Latifah from 2005, a boy named Willy comes in her beauty shop selling chocolate. When he first sees Queen Latifa (whose character is named Gina) he admiringly says to her, "How you doing? Damn you a thick one! You got top, AND bottom!". Gina walks away from him after telling him he will need to learn to be "a little more courteous to the ladies" if he wants to sell chocolate there. "Yeah I got that no doubt"" he says. As Gina walks away he says, "Yo Gina! You gonna buy some 5 dolla chocolate to go with those healthy milkshakes you got?". Gina's mouth drops and we next see Willy and his chocolates getting tossed out of the shop on to the sidewalk.

Although I'm fairly certain the word was likely in common colloquial usage at that time and place, I believe this is the first and possibly only notable reference to "milkshake" as slang until the pop song "Milkshake" by Kelis on her album "Tasty" from 2003 popularized the word.

According to Kelis the word in her song is used to mean "something that makes a woman special". ( aka titties?)

The song was featured in the 2004 film "Mean Girls" and Heather Phares of Allmusic said it is, "basically a three minute tutorial in sex appeal".
"Yo Gina! You gonna buy some 5 dolla chocolates to go with those healthy milkshakes you got?"
by Lillipop February 21, 2015
2/3 ice cream, 1/3 milk, place in blender, mix, serve chilled
strawberry milk shake
by dude December 31, 2003
When a woman is full of cum and continues to partake in sex, all of that shacking and mixing equals a milk shake
If you take enough cream pies you'll have a milk shake
by Gypsy-Jip-C May 20, 2010
Something that brings the boys to the yard... referring usually to a woman's breasts
Chris- wow what a nice milkshake
Mike- u want a sip... its vanilla
Chris- no u idiot i mean that womans juggs
by Jeoff G July 10, 2011
When a man has finished ejaculating and is shaking his penis to get out the last drop of cum.
After receiving a blowjob, the man had a milkshake.
by RoVo July 11, 2013
A magical device that brings all the boys to the yard.
I'm lonely so imma make myself a milkshake.
by naaadine May 11, 2014
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