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1.
Having a girl simultaneously give a blowjob while licking a lollipop.

OR

Licking a lollipop and inserting it into a vagina. (lesbian or solo sex)
My penis got so sticky from that lollijob last night!
by Gina47 December 03, 2010
 
2.
Getting a handjob while licking a lollipop.
Did you hear!? Timmy ditched class this morning during addition tables to get a lollijob on the teeter totter from that fourth grader, Susie! She even brought the lollipop!

Listen, kid. Shit happens. Life ain't all rainbows and lollijobs.
by dicK$hiny & gołdën ñüggęt November 09, 2010