If your girlfriend told the world YOU enjoyed crossdressing, you'd die of embarrassment, right?
Happily, our 1999 celebrity crossdresser is already dead.
It's rugged Jeff Chandler, he-man star of dozens of westerns and action movies.
In her autobiography, waterlogged actress Esther Williams mentioned that Jeff's transvestism began in his childhood. He was raised by a "man-hating" mom and aunt, and anything he did wrong was jeered as "just like a man."
Just like many a TV, Jeff's first experience with frills was when he tried on a pair of panties. In this case, his Aunt Sophie's. Oooh! He had his first orgasm! And after that, Esther declares, Jeff was hooked on the "comfort" of women's clothing.
Your typical crossdresser, Jeff Chandler was way too masculine to look truly "femme." But that didn't stop him from stocking his "special room" with the most expensive undies, gowns, high heels and wigs he could find.
Not wanting to sink the romance between himself and swimming star Esther, Jeff kept his sweets hidden away in the closet until one fateful day.
OOF! He decided to "surprise" Esther by dolling himself up.
Ahem, I think we all know by now, this shock-therapy rarely works. In her book, Esther describes how she reacted: "screaming." She just screamed and screamed and screamed.
Then she demanded that Jeff change back immediately, and cold-cream his face and stop looking "like Betsy Bloomingdale." Jeff countered, "she's a fine looking woman," but Esther wasn't in the mood for repartee.
Despite Jeff's tale of Aunt Sophie's underpants, Esther was not interested in having a "girlfriend." Sad to say, when he explained that he thought of himself as a girl making love to another girl, she was horrified. And when she found out that he was seeing a therapist — who was ALSO a crossdresser — she didn't see any hope at all.
I know,we all wish this story had a happier ending. But in a way, it does. Jeff now serves as a role model for all rugged guys who like to dress up.
Chandler was ruggedly handsome and heterosexual. He bedded some of the great beauties of all time. And...when he dressed up and looked in the mirror, he enjoyed the sweet comforts only known by a very special fraternity (or is that sorority!)