To say something that is bizarre or don't make sense.
Mane Mane: I be trippin with that big 40 cause she don't know the definition of a lick.

Boo Boo: Nigga you rollin on sideways boulevard!
by bigblack365 March 30, 2009
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When a girl takes out a vanilla ice cream cone and smears it all over her man's shaft and sucks him sideways.
Ayo Latisha gave me a bomb-ass sunday-sideway last night!
by ShoreBobbyB November 18, 2015
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Let's say you have a really HUGE cock and/or a very small girlfriend, and she has a hard time going down on your penis orally. Tell her to "suck it sideways"! This way, instead of getting stuck on your pecker head, she can suck you all the way down to your balls, and back again!
MAX JOHNSON: Swallow my cock bitch!

LIL' LIPS: Honey, you know I can't. Your weiner is just way too HUGE!

MAX: Suck it sideways sugar.

LIL': What do you mean?

MAX: Play my Harmonica baby.

LIL': OOOooohhh. Okay.

MAX: Yeah ... yeah ... yeah ... ooohhh, Harmonica baby, NOT corn on the cob. Ouch!

LIL': Sorry Max ... how's that?

MAX: Oh alright honey you KNOW what I like!
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flippin the switch on the hydrolics so that the car sits sideways

when driveing you scoot over to he side of you seat, pimp you hat and just roll

a really good song by Paul Wall and Big Pokey
Sittin sideways,boys in a daze
Sittin sideways,boys in a daze
Sittin sideways,boys in a daze
On a Sunday night I might bang me some...
by elchicoblanco September 22, 2005
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