"There's something there but you have to like freckles," he tells Stern. "I've seen a close up of her chest….a lot of freckles, are you into freckles?"
Stern and Trump continue the sexual conversation about Lohan, and the actress’s rocky relationship with her father, Michael Lohan.
"If the father's a wreck, like the way he is, can you imagine the sex with this troubled teen?" Stern quips.
"Yeah, you're probably right, "Trump replies. "She's probably deeply troubled and therefore great in bed. How come the deeply troubled women, you know, deeply, deeply troubled, they’re always the best in bed?"
"Because they're looking for love," Stern confidently answers before sharing his hypothesis on the sexual prowess of "troubled" women.
"They're looking for positive affirmation, they're looking for a father figure who will love them and tell them they're wonderful and they'll never be enough," he explains. "No matter how many times you tell them they're beautiful, no matter how many times you tell them you love them, they want to suck it up more. They would drain you like a vampire until your head caved in if they could get more love."
A representative for Lohan told CNN in an email that the 30-year-old actress chooses to "disregard" the 12-year-old comments.
"Right now, Lindsay is choosing to focus on the positive things happening in her life and has decided to disregard the comments made about her by Presidential nominee Donald Trump," the rep said. "She is focusing on helping children around the world in need and that's where her passion is."
Trump made more disturbing comments during a 20006 appearance on Stern's show, where he joked about being a "sexual predator" as his daughter, Ivanka Trump, and son, Donald Trump Jr., sat beside him.
The topic of sexually predatory behavior arose after Stern asked a then 24-year-old Ivanka if she was still a virgin. He then questions why Trump doesn’t discuss sex with his daughter.
"Donald, seriously, you know about sexual predators and all that,' Stern said before his co-host, Robin Quivers, added, "Because you are one!"
Trump and Ivanka burst out laughing and he appears to mouth the words, "That’s true," while his daughter pats him on the back.
The two recordings are the latest in a string of crass statements that Trump has made about women over the years. In an Entertainment Tonight segment taped in 1992, Trump is heard making a lewd joke about a young girl. "I'm going to be dating her in 10 years. Can you believe it?" he said.