Ben and Samantha are to be married. Samantha does not want to have sex until they are married in six months. Ben works at a magazine with beautiful women all around him, so temptation is weighing heavily on him. His friend, after fixing his computer, gives him a virtual reality program called "Sensuous Cindy". Ben is hesitant at first but puts on the headgear to start it. Ben finds himself in a candle-lit, romantically-decorated boudoir, where a beautiful blond woman named Cindy has sex with him (despite Ben's reservations). Forest Whitaker appears in the program and talks about how Benjamin is about to get lucky and then whispers "or is he?"
Later that night when he is at home, Ben gets a call - from Sensuous Cindy. He does not tell Samantha who it was or what he had done with Cindy. In the morning in Ben's office, Cindy professes her love for Ben, despite being a computer program. When Ben tries to get on the elevator to go down, it stops and Cindy comes up on the screen, begging Ben to be with her. Ben tells Cindy that their time together meant nothing and that he never wants to see her again. Cindy short-circuits the elevator and leaves Ben inside. He pleads with her to let him out. She does so only so that he will come be with her.
Ben calls his computer-inclined friend to get rid of Cindy. He deletes the program from Ben's computer. But when he gets home, Cindy still keeps popping up everywhere, on Samantha's computer, on his TV and over the phone. To avoid being caught by Samantha and to stop Cindy trying to contact him, he goes to see her in virtual reality. This time, however, when Ben and Cindy kiss, he infects her with a computer virus.
Samantha calls Ben to tell him to go grocery shopping and that she sent him an e-mail of everything they need at the store. While waiting for Ben to come home, Samantha puts on a virtual reality helmet and begins playing the "Sensuous Cindy" program — with Cindy alive, well, and making out with Samantha where Cindy quotes to her that they can't trust men. As they continue making out, Forest Whitaker appears again stating that Cindy is exploring her own sensual nature as the background behind Forest changes to a sky background.