Love in Limbo (1993)

1950's. Gawky teenager Ken Riddle has a wealth of sexual knowledge, but has yet to lose his virginity. Ken is forced to join the workforce after he's thrown out of school for selling explicit drawings to students. At work Ken befriends the rowdy Barry and clashes with his uptight superior Arthur. Meanwhile, smooth ladies man Max Wiseman courts Ken's attractive and available mother Gwen.