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The word fuckboy seems to have materialized from the aether somewhat recently and I can't get a grasp on what it's supposed to mean or where it came from.

I've heard one suggestion that it originated from rap, hip-hop, African-American communities or African American Vernacular English.

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J. Sheidlower, in The F Word, 3rd edition, traces the first sense of it to F. I. Gwaltney's 1954 Heaven & Hell (p.233 where he refers to WWII) "Grimes loves the army and the army's using him for a screw-boy." The first actual use he gives is in J. Blake's 1971 Joint (p. 67, referring to 1954) "They were known as pussyboys, galboys, fuckboys, and all had taken girls' names like Betty, Fifi, Dotty, etc., and were universally referred to as as 'she' and 'her.'" He traces further uses up to 2008, where a work by 50 Cent and D. R. Pledger called Diamond District is cited.

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    Oh, are these mail prostitutes? – tchrist Jul 3 '16 at 2:56
  • I'm not sure what the sense of the phrase is in each case. In the first case for Heaven & Hell is the term being metaphorical as in more modern language the army is "fucking Grimes over?" In the second case is the term is being used to refer a type of male homosexual or homosexual prostitute that cross dresses or whatever? And how is the term used in Diamond District? – Steven Stewart-Gallus Jul 3 '16 at 2:57
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    @tchrist If only the post weren't so damn slow. – deadrat Jul 3 '16 at 2:59
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The following extract from the The Huffington Post tries to trace the possibile origin and different connotations of the term till its more recent usages in rap and hip-hop songs. Its meaning is still not well defined and sexual to nonconformistic nuances appear to characterise the term:

  • In essence, a fuckboy (sometimes stylized “fuckboi” or “fuccboi”) is a (usually straight, white) dude embodying something akin to the “man whore“ label, mashed up with some “basic“ qualities and a light-to-heavy sprinkling of misogyny.But consensus on a singular definition is a work in progress.

  • In its original context, the word was used to insult a man for lack of traditional masculinity. On Urban Dictionary — the respected authority on such matters — the first definition of a fuckboy, from December 2004, is “a person who is a weak ass pussy.” Nothing new. But in the second entry, written nearly ten years later, fuckboys take on a different set of traits, like “relies on his mom but doesn’t respect women"....

    • Connor who won’t calm down with his axe spray tryna infect ya lungs cause he’s a fuckboy, reads one example sentence. And another: Timothy over here asking’ for nudes when all u did was say hello so he’s a fuckboy.
  • Here the term changes meaning, dismissing the subject’s ego and going so far as to call out his inappropriate sexual advances. Insults like that are few and far between. Sure, we can use “man whore” or a “male slut,” but the necessity of those modifiers drives home the fact that whores and sluts are, inherently, women. (Plus, terms like “man whore” attack a man based on his presumed number of sexual partners — “fuckboy” speaks much more to his character.)

Fuckboy Files:

  • The more recent Urban Dictionary entry has 4,000 fewer upvotes than the “weak ass” definition above it — though the first had a decade to accrue those votes of approval — but, after getting reposted to Tumblr, got over 400,000 likes and reblogs. A few months later, a blog on the site called Fuckboy Files popped up, which is essentially a screenshot chronicle of the cringeworthy pickup lines sent to one 25-year-old woman via online dating sites. Now, a simple search now returns a nearly endless stream of Tumblr text posts despairing fuckboys in the dating scene.

  • It’s not hard to see why “fuckboy” is suddenly so popular. It’s immensely satisfying to say — a harsh consonant kicks off a cutting expletive attached to a word that feels comically small. The target is a “boy.” Not a “man.” It’s both wonderfully vulgar and emasculating.

  • A Google search shows the term being used as far back as 2002, when it appeared in a Cam’ron song called “Boy, Boy.” More recently, it’s been used in a growing number of rap and hip-hop songs, as its definition evolves from weakness to something more like douchebaggery.

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