I can't pinpoint for the first use of the phrase, but I first began hearing it in 2011. Around that time, Kanye West had recently broken up with former exotic dancer Amber Rose; Drake had dated Maliah Michel, a stripper from Miami's King of Diamonds; and Chris Brown was dating Draya Michele, also a dancer and soon-to-be reality-show star.
The men, based on their fame and wealth, are deemed desirable -- yes, even Brown. Because some of the women they chose for temporary partners had past occupations deemed less than favorable, the women were designated "hoes." And because they landed desirable men, some considered them to have "won." Hence the birth of the (disgusting) term "Hoes be winning."
Here's the big problem with the phrase. The women are being judged solely on the perception that they have loose morals -- a standard to which men are not usually held. But even if one believes that these women practice less-than-ladylike behavior, that's not all they bring to the table.
What all of the above-mentioned women who have been called "hoes" have in common is that they are widely regarded as exceptionally attractive. That's a trait that some men -- and women, too -- prize. It allows for some people to ignore other potential shortcomings, at least until they get bored. Also, if a woman actually was that sexist epithet, that would not negate any other positive traits she may possess, like loyalty, kindness or empathy.
I hope folks resist falling into the trap of thinking that being virginal (or close to it) makes a woman automatically "good," and allegedly having sex with multiple men makes her automatically "bad." Women are multidimensional. There's no need to buy into a limiting Madonna-whore dichotomy. Some groups of women "win" despite their alleged pervasive sexual history -- certainly not because of it.
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