Cross Dressing Latest News, Photos and Videos

parenting Mar 04, 2010

What Is Your Take on Gender Roles as a Parent?

Does a chic short haircut make a girl a tomboy and her wearing a polo and sweater amount to cross-dressing?

by POPSUGAR Moms

Does a chic short haircut make a girl a tomboy and her wearing a polo and sweater amount to cross-dressing? Does a lil guy wearing a tutu define his sexual preference? Most parents pride themselves on giving their children a better life than they had, but when it comes to gender roles is this true? Modern society may seem like it's come a long way — especially in certain progressive geographical areas where being different is celebrated — but are moms and dads truly comfortable with their kids expressing themselves? What's your tolerance with your tots?

Video Oct 08, 2009

Teen Quits High School Rather Than Stop Cross-Dressing

16-year-old Jonathan Escobar of Kennesaw, GA, was told by his high school to dress "more manly," so the teen who expressed himself by donning wigs and wearing makeup decided to drop out rather than put up with the dictates.

by POPSUGAR Sex & Culture

16-year-old Jonathan Escobar of Kennesaw, GA, was told by his high school to dress "more manly," so the teen who expressed himself by donning wigs and wearing makeup decided to drop out rather than put up with the dictates.

I think Jonathan looks like an eccentric Hitchcock heroine, and I don't see how this is any different from a teen dressing up goth or emo. (Would they get away with telling a butch girl to dress more feminine?) What do you think about the school's claim that he was causing a commotion with his looks — are they being too conservative about gender?

Celebrity Jun 30, 2009

Oh Snap! Mr. Carey at Your Service

Look closely — that's Mariah Carey on the NYC set of her new music video, "Obsessed."

by POPSUGAR Sex & Culture

Look closely — that's Mariah Carey on the NYC set of her new music video, "Obsessed." The sexy singer dressed in drag for a few scenes. Do you think she looks good as a man?

View 5 Photos ›

parenting Feb 04, 2008

Would You Let Your Son Wear a Dress?

Parents want their children to be happy, but what if wearing a dress is the thing that made your son's day?

by POPSUGAR Moms

Parents want their children to be happy, but what if wearing a dress is the thing that made your son's day?

Sarah Hoffman wrote about her conflicting maternal instincts to encourage her 4-year-old son, Sam's self-expression and protect him from ridicule.

Her poignant article, The Pink Dress is in this month's Cookie Magazine. She wrote:

I'd wanted to think that this was just a phase for Sam, but I was beginning to understand that it was not. My son wanted to wear a dress—for real, not for dress-up. He wanted to show the other children in his life, in preschool—the place where he expresses himself publicly—his true self. The pink-sundress-wearing self. And I was going to have to figure out what to do.

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