Dress Code - Dare To Wear Dress - Chapter 1

 ALL STORY LIST | OTHER CHAPTERS - CH 2 | CH 3 | CH 4 | CH 5 | CH 6 | CH 7 | CH 8 | CH 9 | CH 10 | CH 11 | CH 12 | CH 13 | CH 14 | CH 15 | CH 16 | FINAL CHAPTER

Pulling up to yet another traffic light along Spring Creek Parkway, I still marveled at my luck. It wasn’t quite two months since I’d made my escape from Wink, Texas home of Roy Orbison and the Wink Sink Hole. 

My dad still had a t-shirt that proclaimed “I survived the Wink Sink!” I was so glad to be out of there! Some of my old friends thought I was nuts to actually get an apartment in Plano, Texas where I work. 

The apartment is kind of pricey, but I’m only a couple of miles from Xantek Corp, which is a fairly new technology company rising up on Plano’s west side. I never have to get on a freeway to get to work, and I’m minutes away from five major grocery stores and two malls. 

I’m really surprised they hired me, fresh out of college and only twenty-two. They were impressed by some of the software I’d written on contract jobs to make some extra money at college. 

Still, this was my first real job if you don’t count the time I spent working at the gas station in Wink, changing flats and other glamorous tasks. 

I drove my car through the tree-lined and somewhat picturesque parking lot of Xantek’s gleaming steel and glass building. This was such a contrast to the dusty, windblown streets of Wink. I wanted to tell everyone what a great and wonderful life I was having, how perfect everything thing was. 

Well, not quite perfect. Don’t get me wrong. I enjoy the work and they’re making it quite a challenge. The pay is good and I’m out of West Texas. If there was a downside to all this, it was the fact that I was incredibly lonely. 

I might as well be the invisible man. At meetings, still being the new guy, I don’t feel comfortable joining in, and the times I do try to present an idea, I’m largely ignored. 

All the other guys in my department have known each other for a while and go to lunch together and meet after work for a beer or on weekends for sports. The women ignore me as well. 

They certainly don’t invite me to go to lunch with them and make me feel like an interloper should I attempt to join in one of their little cliques that happen to be talking about something I’m interested in. 

And they have definitely made it known that under no circumstances are they interested in a date, even if it’s just to a movie. I got into the elevator for the ride to the twelfth floor where the IT offices were. 

The elevator was fairly crowded, with lots of greetings between the passengers. Again, I was the invisible man. Leaving the elevators, I walked through the glass doors into our department’s lobby. 

Jennifer, the receptionist was shuffling some papers on her desk as I approached. She looked up and said, “Good morning, Mr. Stephens. Ms. Rogers wanted me to tell you she had to cancel your project meeting for this morning.” 

“Did she say why?” 

I asked. That was really annoying because this was the second time this week the meeting was canceled. Until we hashed out the requirements document, there was no way I could start working on the specs. 

Jennifer shrugged, “I’d be willing to bet she’d rather be in your meeting than where she has to go. Mr. Thompson called a staff meeting. All the department heads have to attend.” 

“Would you mind asking her if we could reschedule sometime this week?” Jennifer nodded and jotted down a note. I mumbled a “Thanks” and headed for my cubicle. I walked past Ms. Rogers’ office. 

Ann, Ms. Rogers’ executive assistant was shuffling papers on her desk, trying to look busy. I started to say some pleasantries, but before I could, Ann said without looking up, “You’re late.” Nobody I knew liked Ann much. I know I didn’t. I’d heard rumors she was a lesbian. She certainly seemed to hate men. 

  I looked at my watch, and it was already after eleven-thirty. I was starting to get hungry and felt that I was at a good stopping point, having just achieved victory over an annoying bug in the program I was working on. I looked over the wall of my cube and saw that Lew was still at his desk.

“Hey Lew. Wanna go grab a bite from across the street at Whataburger?” I asked from over the wall. 

“Sorry, Harry. I was going to go with some of the guys down to Spring Creek BBQ. They’re waiting for me downstairs.” 

He pecked at a couple more keys and clicked his mouse on the Save button. 

“Maybe tomorrow, huh?” he said as he left his cubicle. Under my breath, I mumbled, “Gee. Thanks for asking if I wanted to go along.” 

As I started to walk through the lobby, Jennifer called out to me, “Hey, where are going for lunch?” I shrugged, “Probably just to Whataburger. 

I’ll probably just get something to go and bring it back here so I can keep working on my program. I had a breakthrough this morning.” Jennifer picked up her purse and seemed surprised, “Chuck and the other guys didn’t invite you along? 

That was rude. Well, some of the girls and I are going over to La Madeleine. Catch ya later.” Under my breath, I whispered, “Gee. 

Thanks for asking me if I wanted to go along.” 

The clock on the taskbar on the computer screen clicked over three fifteen. I rubbed my eyes for a few seconds. This seemed like a good time for a break. 

I walked into the break room and stopped. 

Sheesh! Looks like I wasn’t the only one who needed a break. 

The room was pretty full. Even Ms. Rogers and Ann were there in the corner, chatting animatedly with some of the other women. Some of the guys were at the table talking loudly about some football game they had seen on television. 

I wormed my way through the crowd to reach the fridge and extract a Dr. Pepper. As I popped it open, I heard Candace say to Ms. Rogers, “Can’t we loosen the dress code a little? 

I can’t believe the dress code requires leather-soled shoes and that we have to wear stockings, even with pants!” Another woman, Joyce chimed in with, “Yeah. And even pants are frowned on here. I hate wearing pantyhose!” Ms. Rogers shrugged, “Now, girls. 

I don’t have a lot of discretion when it comes to applying the corporate dress code.” I looked around the room at the women and in a lull in the conversation, said, “Still, it looks like y’all get to wear a variety of sorts. 

I mean, each day I get to pick from my blue suit, or my brown suit, or my gray suit. 

I get to go kinda wild with the tie, though.” 

Candace looked around at me and frowned, “Harry, at least you don’t have to wear heels, or pantyhose, or have to worry about how your hair or make-up looks. Shoot, boy. You wouldn’t last a day if you had to wear all the crap we have to!” 

I don’t know why I didn’t just go back to my cubicle at that point, but instead, I said with a laugh, “So? How hard could it be? I mean, women do it every day, so how tough could it be?”

 Scowling at me, Ann quickly shot back, “I can’t believe you said that! Do you mean to say that wearing shoes that pinch your toes, underwear that rides up your crack, and stockings that make the back of your legs itch, isn’t hard just because women do it?” 

Sitting on the edge of a table, I responded, “That’s exactly my point. None of those things make you work up a sweat, or break your back, put calluses on your hands, crush or break bones. 

And yet, you act like it’s the end of the world because a little thing like a dress code makes you wear high heels or a skirt or whatever. Shoot, with what most guys have to put up with, your bellyaches about little things like wearing pantyhose seem pretty childish.” 

For several seconds after I finished talking, you could have heard a pin drop. Some guy behind me whispered, “Oh, shit. Looks like Harry really stuck his foot in his mouth now.”

Ann folded her arms and scowled, “Oh, really now! I’d like to see a typical guy put up with what we have to put up with every day! Hell, Harry, you couldn’t last a day if you had to follow our dress code!” 

I laughed, “Oh, give me a break! There’s nothing to it. I could do it for a month as easy as falling off a log!” I couldn’t believe I just said something like that. Ann sat up straighter and asked, “Is that so? Would you care to make a little wager on that?” 

I heard Candace giggle. “What kind of wager?” I asked. “Nothing you couldn’t handle, it sounds like,” Ann said with a grin. Ms. Rogers just sat there and watched with an amused expression. I looked around the room and saw everyone looking at me and laughing in various ways. 

I started to feel very uncomfortable, and I could feel my face turning red, and I was wishing I had kept my big mouth shut. Ann fumbled around in her purse for a moment then pulled out fifty dollars and placed it on the table, “I’m willing to put money down that you couldn’t go one month coming to work dressed as a woman.

I really don’t think you could go for a week, but a month is a sure bet. 

Anyone else want to join in? Put your money on the table. 

If Harry can go the distance, he gets the pot. 

If not, Harry you have to match the bets and the money is divided based on who paid what.” I heard Lew behind me say, “He won’t do it. Hell, he’d be crazy.” Carl laughed, “You don’t have the legs for it, Harry!” Candace sneered, “Put your money where your mouth is!” The room began to spin as I started to drown in a sea of cat-calls, laughing, and taunts. This was awful. What started as a stupid joke was now a disaster. 

I knew my face was beet red. I started having trouble breathing. 

I had wanted more people to pay attention to me, but not like this! Sensing my distress, Ms. Rogers called out above the din, “Hey! Hey people! Settle down. Now, Harry, you don’t have to accept Ann’s rather creative bet, and if you don’t, I understand completely. 

However, if you do, I don’t want this office to turn into a circus. 

Harry, if you come in here Monday looking like just a guy in a dress or like some drag queen if productivity suffers, the bet is voided and the money wagered goes to the Christmas party fund. 

If y’all can’t act professionally about this, then it will end.” 

Everyone was staring at me, waiting for me to make a decision. If I lost and everyone plunked down fifty dollars, I could lose quite a bit of money. 

Part of me just wanted to run and hide somewhere. It was the other part that didn’t want to back down that said, “Sure. I could do that. No problem!” 

Lew slapped me on the back saying, “You’re crazy, man! You won’t make it through the first day!” 

He tossed a twenty on the table where Candace was writing down names and amounts. Ann said with a smirk, “Hey, Harry will need a new name. What should his new name be?” Carl offered, “Harry… Harriet?” Everybody laughed. 

Lew waved as he said, “I know… Hildegard!” Everybody roared with laughter. 

“No freakin’ way!” I almost shouted. Candace apologetically said, “We’ll have to call you something. We can’t call you Harry. You pick, Harry.” 

I thought a moment. I was too numb to do much thinking though. After a few moments I smiled, “I’ve always liked the name Heather.” Candace wrote down another bet and was firm, “Heather you shall be!” 

As I started to walk away, Ann called, “Remember, full adherence to the female dress policy! You can wait until Monday to start.” 

I left the room feeling incredibly stupid. I could still hear people laughing as I sat down in my cubicle.

  I put in an extra hour that afternoon to get to a better-stopping place for the program I was working on, and to give the office a chance to clear out before I left. 

As I walked past Ms. Rogers’ office, I heard the office door open and saw a head poking through. “Oh, good, I caught you before you left. 

I was afraid you’d already gone,” said Ms. Rogers. “I wanted to talk to you before you left.” Stopping in my tracks and turning to face her, I gave a knowing nod, “Sure, Ms. Rogers. I have a feeling I know what you want to talk about.” She sat down on the edge of a handy desk and smoothed her skirt, “Yes, I want to talk about the little bet this afternoon.” 

“I know. I was just trying to make a joke. Things sure got carried away... and fast.” I explained as I walked up to Ms. Rogers. Arms loosely folded and looking directly at me, Ms. Rogers said, “You know, Harry, you don’t have to do this. If you want out, just say so. 

I’ll tell everyone that the bet violates some company policy, and everyone will get their money back.”

 “Thanks,” I said, “but I think I’m going to stick it out. 

It’s not about the money. I just want to show them I can do it. What surprises me is why you’re allowing this in the first place.” Ms. Rogers laughed, “Everyone has been pretty stressed out over the current workload, and there’s no end in sight. It seemed like a harmless way for everyone to let off some steam. 

And, who knows, maybe there will be some lessons learned.” I shifted my feet, “Does that mean you think I’m wrong?” Ms. Rogers smiled and said cryptically, “I didn’t say who was going to learn the lesson.” She chuckled. 

 It was finally Friday as I climbed into my car, the interior superheated by the afternoon sun. 

The last couple of days had been pure hell. I was already the butt of many jokes around the office, and the bet hadn’t even started yet! As I drove out of the parking lot, I decided I’d better start getting ready for Monday. Instead of heading home, I turned down Preston to head towards the mall in Frisco. 

There were quite a few clothes stores there, so hopefully, I would find something suitable to wear. 

After arriving at the mall, I walked around it a couple of times, worrying myself sick at the prospect of actually buying women’s clothes. 

Clothes for me! What had I gotten myself into? I fingered my cell phone, toying with the idea of calling Ms. Rogers and telling her I’d like to back out of the deal, but then I immediately dismissed the idea. 

I squared my shoulders walked into a large department store and headed for the women’s clothing section. 

No sooner had I walked into the middle of the women’s section than I started to panic. I had no idea what I was looking for. I didn’t know sizes or styles or much of anything. A salesgirl must have noticed my distress and walked up to me.

 “Good afternoon, sir!” the sales girl said brightly. 

“How can I help you?” At first, I was going to lie about my true mission here and say something about how I was looking for something for my wife, girlfriend or whatever, but then on second thought, I decided, what the hell? 

Why not just try being honest? What was she going to do, throw me out? I laughed a little nervous laugh and told her, “I really hope you can help me out. I know this sounds stupid…” I saw her expression changed slightly towards the ‘oh, God, now what?’ expression. 

I continued, “But I made this crazy bet at the office. 

I need to dress like a woman for the next week or so or I lose the bet.” She smiled and said without skipping a beat, “Well, sir, I’m sure we can help you find just the right outfits. Is your office casual or professional attire?” I thought I could see the dollar signs rolling in her head from her potential commission. 

I replied, “Oh, very professional. Quite strict, actually.” With a small gesture, the sales girl said, “Let’s see what we can find for you. Come this way?” She led me over to where there were racks and racks of skirts and dresses. 

First, she took a tape measure and made some quick measurements of me. 

Then she pulled a few outfits off the racks and asked me what I thought of them. I said I liked the dark blue one. “Why don’t you go back there and try it on?” 

“Here? L… like right now? I can’t do that!” I exclaimed as I felt my cheeks start to turn red again. She handed me the outfit, “Go ahead. Try it on. It’s okay. I get men in here all the time to try on dresses.”

 I couldn’t tell if she was kidding or not. I went back to one of the little dressing rooms and closed the door. 

The door didn’t go all the way to the bottom, so it would be obvious that the room was occupied by a man. I quickly stripped down and picked up the soft, white blouse. I started shaking as I contemplated actually putting this stuff on. I gritted my teeth and slipped on the blouse. 

At first, I couldn’t figure out why I couldn’t button it, and then realized the buttons were on the wrong side. Why the hell did they do that? 

Next I slid on the skirt and tucked in the blouse. I couldn’t get it to button together until I realized I was trying to wear the waist at my normal place. 

I pulled it up higher and it fit almost perfectly. The sales girl knew her stuff. I put on the jacket. 

The sleeves seemed a little short, but otherwise a good fit. I looked at myself in the mirror and was absolutely mortified. I looked like a complete dork standing there. 

This was never going to work. “Come out and let’s take a look,” called the sales girl. “There’s no one out here. 

It’s okay.” You’ve got to be kidding me, I thought. I’m not going out there looking like this, “No. I don’t think so.” 

“Please, sir. I need to see if the clothes fit you okay. If you’re going to be dressing this way for a week or more, you’re going to need more than one suit.”

 Hesitantly, I slowly opened the door and stepped out. I could tell she wanted to laugh. She controlled herself though, “That’s a good fit. With the right wig, some make-up, shoes, and hose, I think you’ll do fine. 

Go change back and let’s select some more outfits.”

Finally, we’d managed to pick around four different outfits that could be mixed and matched to give me almost two weeks' worth of feminine attire. We then spent (what I felt) an inordinate amount of time selecting underwear bras, panties, slips, pantyhose, camisoles then on to several pairs of shoes to match the outfits. 

I was getting dizzy and had a headache. As I was piling all this stuff on the counter and wondering just how in hell I was going to get this out to my car, the sales girl seemed pleased, “I think you’ll be very happy with these clothes.”

 As she started totaling up the purchases, she continued, “I would have taken you over to our complete make-up counter, but I think you’re going to need the help of a professional who is used to handling clients such as… um… er… yourself.” 

She handed me a card and explained, “You need to give her a call as soon as you can to see if she can get to you tomorrow. 

She normally just does makeovers, but she’ll also do consulting and, well, training for cross-dressers, drag queens and you know, people like you.” 

As I took the card, I said, “Well, you know, I’m not a cross-dresser or a drag queen, transvestite, whatever. 

I’m just an idiot who accepted a stupid bet.” She finished ringing up the total as she said, “Yeaaahhh…” 

She took my check, “Have fun. I know I always feel great after buying some new outfits. Have a great week next week!”

 She slammed the cash register closed and gave me that ‘I’m done with you now so leave’ smile. I took a quick look at the card before I began grappling with my new wardrobe. The card read “Thelma’s Glamour Emporium.” I decided to give Thelma a call when I got back to my car.

 I put the card in my pocket, grabbed my load and then tried to remember which direction I needed to go to find my car.