Plot
At a bar in Philadelphia in 1999, a man named Santos sits in a booth while nervously clutching a briefcase. He exits in a hurry and is followed by the bartender, who murders and decapitates him in an alley.
Elsewhere in Philadelphia, Jamie and Sukie are lovers whose relationship unravels over Jamie's infidelity with Carla. After Sukie kicks her out of their apartment, Jamie learns that her friend Marian is planning a trip to Tallahassee, Florida and decides to tag along. They head to a drive-away car service where someone can transport a car one-way for another client. Due to a misunderstanding, they are given a car that was already booked for a trip to Tallahassee.
Moments later, a trio of criminals consisting of Arliss, Flint, and Chief comes to the shop to pick up the car headed to Tallahassee. They find that Jamie and Marian have taken it by accident, along with unspecified cargo tied to their illegal dealings.
While Marian wants to go straight to Tallahassee, Jamie constantly tries to convince Marian to loosen up by taking detours and trying to have casual sex at lesbian bars along the way. Marian prefers to read Henry James' The Europeans on the trip, but slowly comes out of her shell due to Jamie's prodding.
When the pair finally enters Florida, their car gets a flat tire. They open the trunk and find the briefcase Santos was holding and a basket containing Santos' preserved head.
Jamie and Marian are followed by Arliss and Flint, who are led on a wild goose chase by a soccer team who had invited Jamie and Marian to a party. When Jamie and Marian check into a hotel using Jamie's credit card, the mob is tipped off to their location. Jamie convinces Marian that she needs to have a positive sexual experience to enjoy life more, and they have sex where Marian climaxes. Arliss, Flint, and Chief arrive in Tallahassee. Jamie decides to use the contents of Santos' briefcase: a collection of dildos that were created from plaster casts of men's erect penises, including one of Senator Gary Channel. Marian is shocked upon finding her with Channel's dildo, but Jamie insists that she wants the sexual release that Marian had the night before.
Arliss and Flint burst into their room, retrieve Santos' head and the briefcase, and abduct Jamie and Marian at gunpoint. The women are tied to chairs and gagged in a backroom at a dog racing track. Chief arrives to meet them all and explains that the sex toys are created from plaster moulds from the genitals of influential public figures by Tiffany Plastercaster.
Channel is fearful that his reputation will be ruined if anyone learns of the dildo, which Jamie had used and left behind in the hotel room. After the gangsters have an argument that leads to Flint shooting the other two dead and running away, Jamie and Marian escape. They briefly make a plan to retrieve the last dildo and regroup at a new hotel. Once there, Jamie and Marian shower together, where Marian states that she wants to make love with Senator Channel's dildo, which they do. Then, they decide to blackmail Channel.
Sukie has also been en route to Tallahassee in her capacity as a police officer after Jamie tipped her off. Jamie and Marian meet Channel at a lesbian bar and give him the dildo in exchange for one million dollars. Sukie intercepts them as they exit, and Channel, misinterpreting the interaction, turns back around to try to kill the women. Sukie shoots him. Channel survives, but his reputation is ruined when newspapers begin publishing articles about his criminal connections and the dildo collection.
The next day, Jamie and Marian meet with Marian's aunt at their hotel. Jamie casually mentions that she and Marian plan to go to Massachusetts, as same-sex marriage is legal there. As the trio drives away, a bellhop races to give them a bag that they have left behind, which contains two plaster casts Jamie had made of the dildo modeled after Channel's penis.
