Donald Trump tends to get personal when he’s striking back at someone who has criticized him. But when his critics are women, those terms often include broad smears of their sexual behavior.

In Trump’s battery of insults, there are two kinds of women: those who have too much sex, and those who don’t have enough.

Former Miss Universe Alicia Machado and Democratic nominee Hillary Clinton have inhabited either edge of this Trump spectrum. In a series of early-morning tweets Friday morning, Trump called former Miss Universe and new Clinton campaign asset Alicia Machado “disgusting” and urged his followers to look up her “sex tape.”

Early last year, Trump retweeted an apparent joke that compared Hillary Clinton’s ability to serve as President to her ability to sexually please her husband: “If Hillary Clinton can’t satisfy her husband, what makes her think she can satisfy America?” He later deleted the tweet.

In both cases, Trump targeted his opponents according to the classic double-bind of expectations for adult women: They can be called a slut for having sex, or pathetic and frigid if they don’t. Add to that another old sexist trope: If a man cheats on you, it’s your fault.

For the record, no evidence has yet surfaced of Machado ever making a sex tape. Trump might be referring to a slightly racy video from her 2005 appearance on a Spanish reality show, in which grainy bedroom footage appears to show her under the covers (yet clothed) with a male co-star, the kind of “sex scene” that is routinely staged for reality TV shows.

Trump has long judged himself by a different standard, frequently boasting, sometimes in unusual detail, of his sexual accomplishments and tastes, both as a bachelor and during his three marriages. Asked Thursday night about his marital history, which includes an affair with the woman who became his second wife while he was still married to his first, Trump said there was nothing to criticize. “I have a very good history,” he told NH1 news in New Hampshire.

In a 1999 radio interview with Howard Stern, Trump spoke about his own sex life and put a “naked” Melania on the phone to tell Stern what she was wearing and how often they have sex. Stern asked him to “have sex with her while we’re on the phone” and Trump laughed, suggesting that if he took him up on the offer, Stern would “watch his ratings go even higher.”

Years later, in the midst of his 2015 feud with Megyn Kelly, Trump slammed the Fox News host for discussing her sex life with her husband on the very same Howard Stern show, even suggesting that it was impure of her to be open about her private activities.

He’s also smeared other high-profile women for their alleged sex lives, from Morning Joe’s Mika Brzezinski (calling her Joe Scarborough’s “very insecure longtime girlfriend”) to Angelina Jolie (whom he said has “been with so many guys she makes me look like a baby.”)

But if you’re a woman in Trump’s world, you’re damned if you do, damned if you don’t. Trump has repeatedly attacked Rosie O’Donnell for what he claims, without evidence, are sexual failings. “She better be careful or I’ll send one of my friends over to pick up her girlfriend,” he said once. “Why would she stay with Rosie if she had another choice?” He also attacked another powerful woman, media mogul Arianna Huffington, for the failure of her marriage.

In recent weeks, Trump’s close allies, some of them adulterers themselves, have begun to pummel Clinton for her husband’s sexual infidelities while praising Trump for refusing to attack her himself.

“The president of the United States, her husband, disgraced this country with what he did in the Oval Office, and she didn’t just stand by him, she attacked Monica Lewinsky,” said Rudy Guiliani, former Mayor of New York City, who has admitted to cheating on his second wife. “And after being married to Bill Clinton for 20 years, if you didn’t know the moment Monica Lewinsky said that Bill Clinton violated her that she was telling the truth, then you’re too stupid to be president.”

So Trump’s treatment of Machado and Clinton are not isolated spats or just the tweets-du-jour. Taken together, they’re perfect examples of the way Trump has come to target women antagonists by attempting to shame their most private behavior.

The Clinton campaign is clearly betting that Trump’s attacks will hurt him with women voters, an all-important demographic that often decides elections. She highlighted Trump’s late night Machado tweet hours later Friday morning.

“What kind of man stays up all night to smear a woman with lies and conspiracy theories?” asked the campaign’s official Twitter account. And in the debate on Monday, she made clear that she hopes women are motivated on Election Day by such statements.

After she brought up Trump’s past criticism of Machado in the debate, she turned to Trump and said, “you can bet she’s gonna vote.”

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Write to Charlotte Alter at charlotte.alter@time.com.