The Big Bet (1985)

A teenage boy that had early sexual encounters is having trouble finding them now and spends a lot of time fantasizing about the women he knows When a beautiful new girl comes to town he makes a bet with the other guys that he can get her into bed within 10 days His chief rival stacks the deck though by threatening to expose the new girls sordid past she was wrongly accused of being involved in an orgy at her previous school if she sleeps with our hero Confused about his situation the boy seeks counsel from the sexy older woman across the street and she helps him come to terms with his predicament