tagTransgender & CrossdressersDo You Know A Cross-dresser?

Do You Know A Cross-dresser?


Trans-genderism: Cross-dressing

I never considered writing a story about cross-dressing until I was confronted with it. I just recently found out that a friend of mine who I have known for several years is a cross-dresser. He's a good guy, a family man, is married with kids, and, by all accounts, appears normal. Whatever that means? Yet, what is normal? Am I normal as opposed you or to someone else? Who is normal enough to say what is normal and what is not? Where is the standard of normalcy written?

His wife knows that he enjoys wearing women's clothes; she even helps him get ready, helping him with his hair and makeup. His children, still very young, do not know that Daddy enjoys dressing as a woman. Boy, there goes his career as a little league coach. He is a champion golfer and we have played together in a foursome, although he is much more of a professional golfer than I am. I am just a duffer.

Stuart works as a manicurist at a famous Boston hair salon and all of his co-workers know that he is a cross-dresser. With a set of fake big boobs, a padded ass, high heels, a wig, and a serious fashionable dress, he dresses as a woman every year at the company Christmas party. The thing that I recently found out was that cross-dressers are usually heterosexual whereas transsexuals are usually homosexuals. In my ignorance, I combined them together as one making no difference in my mind between the two. Actually, I should have known. I've watched enough Jerry Springer shows to know the difference between the two.

Nonetheless, the question that I have for Stuart is, the next time that I see him, where does he buy women's shoes in his size? He takes a size 13.

I am a huge movie buff and when I sit here and think about it now, as I write this story, cross-dressing has played a big part in my hobby of watching movies. Mrs. Doubtfire, Tootsie, The Birdcage, Big Momma's House, White Chicks, Yentl, She's the Man, and Victor/Victoria, just to name a few of the more famous films that have played at my local cinema throughout the years for my viewing pleasure with the theme of cross-dressing and gender-bending flashing conspicuously across the silver screen.

I happened to be at the local Marshall's, a clothing chain in the Northeast part of the country, when I noticed this woman who was dressed to kill. She was wearing an elaborate hat, high heel shoes, a sophisticated dress with a plunging neckline and a dramatic hemline, and a fur. I may not have noticed her except she appeared out of place in the store where most of the female customers who shopped the store were in their typical drab uniform of sweatshirt, blue jeans, and sneakers while dragging a couple of bored and disobedient children along with them. She was better dressed than any other woman in the store. Of course, the other thing that made this woman stand out was, with her high heels and puffed up wig; she stood about 6'7" and had shoulders that rivaled Teddy Bruski's of the New England Patriots.

It took me a moment for my brain to wrap around the sight of this woman. At a mere 6' tall, she towered over me. I did not want to stare, but I could not help myself. I could not believe how enormous this woman was. She was, without doubt, the tallest and biggest woman that I have ever seen in my entire life. Although, she was fashionable and impeccably dressed, she looked ridiculous. Then, when she blocked the aisle that I was in with her carriage and my exit with her person, I was a bit nervous. It was then that I knew that this was a man cross-dressing and not a very tall, manly built woman.

"Excuse me," I said.

"There's no excuse for you." She stared me down.

"Pardon," I said, walking toward her and trying to squeeze out between her and her carriage.

"What? You don't say, hi?" She looked down at me and I looked up at her. "What are you too embarrassed to be seen with me?"


"Hi ya, big boy," he said punching me hard in the shoulder.

"Why are you dressed like this?"

"Duh!" he said looking down at me.

"Are a cross-dresser?"

"What gave me away?" He lifted the fake boobs up in the palms of his big hands. "Was it the fake boobs?"

"Well, they are a little big. What are they a size double G?" We both laughed. "Actually, it was you standing about 6'7" and weighing in at 240 pounds that made me just a little suspicious."

"Yeah, I guess I do stand out in a crowed, don't I?"

"How long have you been doing this?

"I've been doing it for a while." Suddenly, he fell into the role more of a man, pushing his wig and hat back to reveal his hairline underneath, and taking the posture of one of the guys. He looked comical.

"Does Karen know?"

"Of course, she does my hair and makeup."

"What about the kids, do they know?"

There was nothing feminine or sexy about Stuart dressed as a woman. I think that I could have made a better looking woman than he did. Yet, it was then that I realized that it was the cross-dressing, more for him than it was for anyone else. Imagine Brad Garrett who plays Robert, Ray Romano's older brother in Everyone Loves Raymond, dressed as a woman. That is what Stuart looked like.

I should have known, now that I do know. He tweezed his eyebrows, for God's sake. What guy tweezes his eyebrows? Secondly, he wears nail polish. What guy wears nail polish? I do not know any guys who wear nail polish. I just figured that wearing the nail polish was part of his job as a manicurist. Now, in hindsight, it all adds up. I looked down at his legs. Yep, he shaves his legs, too. Okay, now that is something that I would never do, shave my legs or wear nail polish or tweeze my eyebrows, for that matter.

Yet, he appeared happy.

"Wanna grab a beer?"

"Uhm, you know, Stuart, I'm late for an appointment." I cringed at the thought of walking in a sports bar with Stuart dressed in drag. Surely, we would be in a fistfight with some unruly thug. "I, uhm, just bopped in her to return something." I smiled up at him. "I'll catch you later."

"Yeah, maybe, we'll shoot a round of golf or" he raised his voice as I headed as fast as I could for the door "we'll give one another a bikini wax...again."

I turned around to look at him as I hurried out the door. Actually, everyone in the store turned around to look at him.

"What?" He said to the other customers around him who stared. "You never had a bikini wax.?"

His attempt at embarrassing me about the bikini wax worked. Suddenly, I felt like a cross-dresser undressed and wearing regular man's clothes while trying to hide the fact that I was a cross-dresser. It was ridiculous. Now, I could never shop at the store ever again.

Stuart and I did not see much of one another after that and I feel bad about that. He was a great guy, a good friend, and a talented golfer. Only, I could not get beyond the thought of him being a cross-dresser and the vision of seeing him dressed as a woman. He is the better person than I am. I could never walk out in public dressed the way he was dressed, yet, there he was confronting what he needed to be happy and I applaud him for that.

Now, that I think of it, it would be fun, funny, even, for all of us guys to get together and dress up as women and make a night of it, maybe even go to a strip club dressed like that. A couple of the guys have beards and mustaches. Now, that would be funny. One of the guys is even bowlegged. Only, I think that Stuart may feel that we were making fun of him instead of trying to accept him for who he is.

Part of me feels sorry for him. Maybe, not as much now that he has given into it and accepted it but as a younger man, he must have been tortured inside, confused, angry, and hurt. I cannot imagine the misery he must have gone through to get where he is now.

Take care, Stuart, wherever you are.

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