To match the previous question, I would say so. A hard call. I do not know that any bibliographical work has been done that would give a positive identity on what book would have been the first. There are quite a few from the underground culture. Are we talking city scape political titles or country rural edenists? Religious ecstatical WOW books or mundane how one may survive on no money a day books or books devoted to various aspects of illegal smiles?
I used to have a sizable collection of beat literature in firsts, which then spilled over into a large collection of "hippie" literature. There are a lot of basement, hand-cranked publications in the latter. It was a large, untidy, sloppy even, amassment. While a good many hippies idolized people like Kerouac , there is a point at whic one says beat not hippie, or hippie not beat. And then , of course, as the underground became more radically political , one added "yippie" ... and there were always those who preferred the word "freak" over "hippie".
Those, like Camille Paglia, who ignorantly maintain the hippies did not read, or appreciate literature, were living on another planet. The planet Blinkerblind, I suppose. By the way, if one has not read Camille Paglia , one has missed out on some excellent and sharply witty and insigtful literary criticism.
