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Barbara Walters - ABC News 20/20

By ALAN B. GOLDBERG - April 25, 2007

This past Christmas [2006], Riley Grant received a present that can be described as bittersweet -- a video game that allowed her to morph a digital body into anything she wanted. Almost immediately, Riley, a 10-year-old transgender girl who is biologically a boy, adopted a virtual female persona. If only life were so easy, that she could punch a button and turn into a girl.

"She has a birth defect, and we call it that. I can't think of a worse birth defect, as a woman to have, than to have a penis," Riley's mother, Stephanie, told Barbara Walters. "She talks about the day she'll have a baby. That's not in her future. But she sees herself as growing up to be a woman."

… From the beginning, the Grants knew that the twins were different. While Allie was outgoing and friendly, Richard was clingy, quiet and passive. His mother knew that he wouldn't become a macho little boy.

'I'm A Girl'

Richard refused to swim topless, always wearing a shirt in the pool. By age two, he became clearly jealous of his sister's "girl" things -- her toys, her pink drinking cups, and especially her clothing.

"We were getting dressed, and he wanted to wear a dress. He wanted to be pretty like his sister," said Stephanie. "He was saying, 'I want a dress. I'm a girl, Mommy, I'm a girl.' And I'd say, 'No, honey, you're a boy. You have a penis, you're a boy. Allie's a girl.'"

Then, when the twins were only two and a half, an incident after a bath convinced the Grants just how seriously confused their son was about his gender identity. Stephanie found Richard holding a nail clipper against his penis, saying that "it doesn't go there."

Richard's pediatrician told the Grants that they needed to teach their son how to be a boy. So the Grants encouraged Richard to play with boy's toys and do boy's activities, but to no avail. Richard even refused to attend his own birthday parties knowing he would only get boy presents. The worst time was Christmas.

"It got more exasperating for him when he looked over and saw his sister's things, the things that he wanted," said Neil Grant.

'We Knew We Had to Hide It'

Finally, when Richard was just three years old, Stephanie made the drastic decision to let her son start dressing as a girl. They called it "girl time." Richard could dress up in his sister's clothes but only when his father Neil was out of sight. The secret between mother and son went on for months.

"I took him shopping by himself and we bought his own skirt and his own little tank top because…that little girl trapped inside was so happy when this would happen. But we knew we had to hide it, and we hid them in the back of the closet," she said...