A 2004 article (but still very interesting) about a crossdresser (and Silverton, Oregon city official!) by Meg Daly:
Rasmussen says he has been a cross-dresser all his life, though he has only been out for the past 10 years. For many years he was ashamed; he thought he was the only man in the world with a proclivity for women’s clothing and therefore must be “sick and bad.” Then an Internet search revealed a much wider world to him and, he says, “the floodgates opened.”
He found his way to Northwest Gender Alliance, which he credits with helping him get to a place of being comfortable with himself. In the mid-1990s he started getting his nails done and was soon going out in public dressed entirely in women’s attire. Though he was terrified at first, he soon realized “90 percent of the problems [he faced] were right between my own ears.”…
Comfortable with the terms genderqueer and transgender, he says he has nonetheless never considered having a sex change.
“I can be perfectly happy in a man’s body,” he says.
He did, however, save up his money and get breast implants four years ago.
“Cleavage is a cross-dresser’s nirvana,” he says. He had worn prosthetic breasts for a few years to “try out being a guy with breasts.” Now that he has the real thing, he says he has regretted it “for all of about 15 seconds” when he first opened his eyes after the surgery.
One of his favorite adornments for his bust is a T-shirt he had made that answers any silent passersby who may be wondering, “Why does Stu do that?” It reads simply: “Because girls have more fun. ”