Ken Regan/Focus Features
Paul Chi
August 25, 2009 07:20 PM

Dude looks like a lady! In his new role as a cross-dresser, Liev Schreiber explores his feminine side by donning a dress and wearing heels.

“It was exhilaratingly humiliating,” Schreiber, who plays a tough, ex-Marine transvestite in Ang Lee’s comedy Taking Woodstock (opening Friday), tells PEOPLE. “But I completely became giddy in a strange way the moment I put on the dress.”

Overcoming his initial reactions, Schreiber, 41, admits that he suddenly became conscious about his looks and developed a strong desire to feel more attractive. “Vanity quickly set in, and I thought to myself, ‘I wish my belly was flatter,’ ” he says with a laugh. “Let’s face it, I don’t look great in a dress, but it’s nice to hear I have nice legs.”

Now that the father of two sons has worn women’s clothing, shaved his body hair and stood in high heel shoes, the rugged 220-lbs. actor sympathizes with women who often endure pain in the name of fashion.

“The shoes are awful,” says Schreiber. “But for a 6-foot-3-inch [tall] man, to walk around in stilettos is nearly impossible. But women have no idea what it’s like for a grown hairy man to remove all of his hair from his body. Now that hurts!”

So how did fiancée, Naomi Watts, react? “She was horrified! It flipped her out,” says Schreiber. “She was in shock for 30 seconds. Then she started to crack jokes.”

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