Etymonline.com mentions this:
bitch (v.)
"to complain," attested at least from 1930, perhaps from the sense in bitchy, perhaps influenced by the verb meaning "to bungle, spoil," which is recorded from 1823. But bitched in this sense seems to echo Middle English bicched "cursed, bad," a general term of opprobrium (as in Chaucer's bicched bones "unlucky dice"), which despite the hesitation of OED, seems to be a derivative of bitch (n.).
and then we have:
bitching (adj.)
also bitchen, "good," teen/surfer slang attested from 1950s, apparently from bitch (v.) in some inverted sense.
How did the second, positive meaning arise from the first extremely negative (and long) history of the word? What and where are the earliest uses of the word in this newer positive meaning?
Best Answer
J.E. Lighter, The Random House Dictionary of American Slang (1994) reports that the origin of bitching in a positive sense was student use:
The instance in Frederick Kohner, Gidget (1957) reads in context this way:
Gidget is a surfer-girl novel, written by the real-life father of the original gidget (gidget, we learn, is a surfer palindrome for "girl midget"). A discussion of the book and of the California surfer subculture of 1957 in "Gidget Makes the Grade," in Life magazine (October 28, 1957) reveals another instance of bitchen in that subculture:
I don't recall ever having encountered the term wetbacks except as an derisive (and offensive) name for braceros—unlicensed Mexican nationals who cross over the U.S.-Mexican border to pick crops and perform other hard labor in the United States. (The term wetback refers to their having supposedly crossed the border (illegally) by swimming across the Rio Grande, which forms the entire border between Texas and Mexico from Brownsville/Matamoros on the Gulf of Mexico to El Paso/Ciudad Juarez in far west Texas.
In any event, the positive sense of bitching can apply to bitch as well, as this glossary entry in "The Parlance of Hip," in Esquire, volume 52 (1959) indicates:
The "not in a derogatory sense" language here may be intended to indicate that a a person using the term may not mean to convey the idea that the girl or woman so designated is unpleasant or unattractive in any way, but the notion that "bitch" is therefore not derogatory appears to be a relic of a particular (and peculiar) male view of the subject at the height of the Mad Men era.
And a glossary in the Saturday Evening Post, volume 234 (1961) has this entry for bitching, along with entries such as "like wow," "like cool, man," and "swinging":
Wentworth & Flexner, Dictionary of American Slang (1960) find an even earlier antecedent for bitching in a positive sense in bitchey:
The Farrell citation comes from a short story called "Looking 'Em Over" (1930).
It's not impossible that the use of bitchin' in 1950s surfer lingo directly recalls the early 1930s usage of bitchey in a similarly upbeat sense. But it may be even more likely that the adjective bitching (or its more elaborate sibling son-of-a-bitching), popularized by soldiers during World War II and the Korean War, provided the inspiration for the newly positive bitchin'. In any event, it seems truer to attribute its origin to the surf lingo of Southern California in the late 1950s than to student use, as Lighter unaccountably does after noting its early occurrence in Gidget.