8 comments/ 51569 views/ 3 favorites Do You Know A Cross-dresser? By: BOSTONFICTIONWRITER 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?" "Stuart?" "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. 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.