tagReviews & EssaysDo You Know A Cross-dresser? Ch. 02

Do You Know A Cross-dresser? Ch. 02


Do you know a cross-dresser? I bet you do only you'd never know it.

I ran into my friend Stuart over the holidays. I haven't seen him since I saw him in Marshall's clothing store last winter when he was dressed as a woman, albeit a super sized woman. He was a bit cold to me and I don't blame him. We had a polite conversation asking after our wives and kids and always ending the conversation talking about Tom Brady and the Patriots. Still, the interaction saddened me. I had driven a big wedge through the heart of our friendship by not accepting him for being a cross-dresser.

This day, he was dressed as a man wearing sneakers, flannel shirt, jeans, and a Patriots football jacket. Had I not known that he was a cross-dresser, I never would have noticed his tweezed and shaped eyebrows. Now, I couldn't help by stare at his eyebrows.

Before I found out about him being a cross-dresser, I just would've figured that his eyebrows looked a bit strange, but weird eyebrows never would have led me to suspect him being a cross-dresser. That was when I noticed that he paints his fingernails. Besides, we guys don't look at other guys that closely.

Now, I always knew that he did that, but that was his profession, he's a manicurist and makeup artist. So, I never suspected him being a cross-dresser just because he paints his fingernails. I mean, I'd never paint my fingernails, but I'm not a manicurist and makeup artist. Now, that I know that he's a cross-dresser, I should have suspected that he was with the strange eyebrows and painted fingernails.

Yet, he's just a man's man, a manly man, and a macho man. It still doesn't add up. How can someone like him be a cross-dresser? There I go again being judgmental.

Stuart is tall, 6'3 or 6'4 and he's a big man weighing around 260. He played football as a defensive lineman when he attended Boston College. Gees, I just had a thought. I wonder if cross-dressing had something to do with some of the football players wearing pantyhose because of the cold. Nah, that's dumb. So, to see Stuart dressed as a woman shocked the shit out of me.

When I saw him last he was wearing a fox fur coat over a navy blue dress. The fox belonged to his wife I think. I didn't recognize the coat. I know she has a fox, but it looked so different on him. His physique is so big that the coat appeared small on him, almost as if he was a caveman wearing an animal skin.

The cuffs came up to the middle of his forearms. He looked a bit ridiculous. Moreover, the puffiness of the fur made him appear even bigger, not to mention that he was wearing a puffy blonde wig, high heels and too much makeup, red rouge and blue eye shadow with bright red lipstick. The combination of the blonde puffy wig with high heels made him a conspicuous 6'7 or 6'8" tall.

Actually, it wasn't only the coat that made him look ridiculous. It was obvious to anyone who saw Stuart dressed as a woman that day that he was a man dressed as a woman. He would never fool anyone that he was a woman. Of course, I wondered which restroom he used. I figured he still used the men's room or maybe he avoided using any restroom waiting until he returned home to relieve himself.

That day still haunts me. I was insensitive to him and I felt horrible about it. I couldn't wait to get away from him. He wanted to go out for a beer, but I was too embarrassed to be seen in public with him. I was just as shocked that he willingly would walk into our favorite bar dressed like that and not give a care that the guys we drink with would see him and give him a hard time, maybe or maybe not because he was so big.

I wish I felt that self-assured about who I was. I wish I was more like Stuart in that regard. I waste too much time wondering about what people think of me. I need to be more like Stuart, but without the dress.

He made me feel judgmental and less the man than he was. Dressed as a woman or a man, he was comfortable in his skin and I wasn't big enough to accept that. It took me a long while to come to grips with that, to wrestle the feelings from my mind, and to understand that I made him feel bad about who he is. How dare I? It was wrong of me to treat him that way. Certainly, I was not much of a friend to him that day.

He's a great guy, a wonderful father, a loving husband, and has been a good friend over the years. Admittedly, he caught me by surprise. I never in a million years expected him to be a cross-dresser. Now, if I thought of one of my friends being a cross-dresser, I would have suspected Gary.

He's small, about 5'5 or 5'6" and a bit effeminate. With his diminutive stature and small features, he'd probably make for an attractive woman. Gees, I can't believe I'm imagining Gary dressed as a woman. I may need therapy. Yet, like Stuart, he's been married 25 years and has 3 kids. I don't know, nowadays, it's difficult to tell the players without a scorecard. You never know who is gay, lesbian or in the case of Stuart a cross-dresser.

Stupidly, I allowed our friendship to slip away. I didn't call him after that. I didn't know what to say to him. His blatant in your face cross-dressing made me uncomfortable. I'm sure that I made him feel bad. I'm sure that I hurt his feelings. Only, I don't understand any of it, why he feels the need to dress like a woman. I don't get it. Yet, it doesn't matter. He's still my friend and I'm big enough to accept him the way that he is.

When I bumped into him that day, he didn't avoid me. Matter of fact, he walked right up to me. I knew it was a man dressed as a woman, but I didn't know it was my friend Stuart dressed as a woman. He thought it funny to block the aisle. It took me a minute or two before I noticed that it was him. Nonetheless, what I did notice was that he thought he looked good dressed as a woman. He was beaming. He looked happy. He thought he looked beautiful.

I'll still never forget the image of him lumbering down the dress aisle holding this handbag that looked tiny against his huge frame and walking like a guy who was forced to wear high heels. Where he found women's shoes to fit his size 13 feet and a woman's dress to fit his broad shoulders is beyond me.

I decided to confront my prejudice and apologize to Stuart and ask him out for a beer, regardless if he is dressed as a man or a woman. Only, I really hope he is still dressed as a man. I was out running errands and swung by his house. There were a couple pickup trucks in his driveway and I almost didn't stop. I figured he was having company, but I remembered he said that he was having his basement done over. Maybe, these guys were part of the work crew.

The garage door was open and there was a television set perched on the shelf with the Patriot's game blaring. I walked up the drive and stopped when I saw Stuart and his friends wearing Patriots' cheerleader outfits. Okay, maybe had they shaved their legs, the image wouldn't have been as disturbing, but one of the guys was wearing boxer shorts which were on prominent display beneath his short skirt.

Stuart threw a big arm around my shoulder, introduced me to the guys, and we all had a swell time cheering for the Patriots.

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