Crush Me, Kill Me

To understand Florida's most bizarre unsolved murder, it helps to wear stiletto heels.

"I didn't see no physical marks on her at the time," he says. "She was free to come and go. If it was that bad, she could have left."

And Loudermilk's mother says she had heard the opposite, that Loudermilk had been pushed around by his six-foot-tall wife.

Loudermilk's sketched fantasies
Loudermilk's sketched fantasies

What certainly seems true is that the Loudermilk marriage was disintegrating in 1999. Several of Loudermilk's friends told police that he had begun using cocaine several months before his death. The Loudermilk house was full of strangers partying at all hours of the night, and several sources say that Bryan and Stephanie were fighting about drug use and Stephanie's affair with a friend, known only to investigators as Robert, who was living with them. One friend reported that Robert threatened to kill Loudermilk after being run off his property the weekend before Loudermilk's death. According to Loudermilk's mother, the couple was considering divorce.

A friend, Sarah Ruth McCleod, who was with the Loudermilks the night before Bryan died, reported that the couple seemed happy, "drinking and partying." The next morning, as Sarah left the house, Bryan told her that he was going fishing. Stephanie claimed that she didn't see Loudermilk at all that Monday, remaining in the house with her kids.

According to several witnesses, Stephanie gave her friend Kimberly "Krystie" Medders several photographs the day Loudermilk died. When investigators questioned Medders about the photographs, she initially denied that she had them, then answered that the photos had been destroyed.

"They were probably just some more photographs of her walking on some animals," Garrison says when asked about them.

But that same day, Stephanie handed over boxes of photos and videotapes that showed the Loudermilks' crush activities and implicated her in acts of animal cruelty. For some reason, she held back just a few of them.

After Loudermilk's death, Stephanie cut off contact with his family and obtained a restraining order against Loudermilk's mother after Bailey made attempts to contact her grandchildren.

Bailey hasn't seen her grandchildren since Loudermilk died and is tight-lipped when she talks about Stephanie today. "I don't want her in trouble," she says. "I wouldn't have tried to get her in trouble about nothing like that because she has my grandkids."

In 1999, Bryan Loudermilk was nominated for immortality by the Darwin Awards, the tongue-in-cheek, web-based honors bestowed to those who "improve the human genome by removing themselves from it." The nomination of Loudermilk specifically blamed his wife for driving the car and suggested that Loudermilk got exactly what he deserved. "A man who would lie in a special pit while a woman he groomed for 'crush' videos drove over him, shouldn't be surprised when he winds up holding a Darwin Award."

Romero, who prosecuted Stephanie before ultimately allowing her to plea-bargain for a reduced animal cruelty sentence, was annoyed at the website's assumption of her guilt. "I saw the Darwin Award," he says. "They got it all wrong. She was never charged with murder."

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