Dress Code - Dare To Wear Dress - Chapter 9

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I stepped into the huge conference room, wearing a black skirt and matching jacket and shoes. Ms. Hoden waved to me from a table near the dais. Several people were already seated and I looked up into the room and saw at least two hundred girls sitting at rows and rows of tables. 

I started to panic seeing so many girls in the audience. 

“Ms. Stephens!” said Ms. Hoden as I shook her offered hand. 

“It’s so good to see you again. How’s our project coming?” I smiled at her and reported, “I turned in the final specs to management this morning, and I got our Agile team assembled and we’ll be all ready to start Monday morning.” 

“Great, great,” said Ms. Hoden. 

“Heather, I’d like you to meet Mr. Dylan Donovan. He’s one of our marvelous mentors.” 

Dylan offered his hand and I gave him a soft, wimpy handshake that men hate. He said, “Nice to meet you, Heather. I hope you can join our ranks of mentors.” 

“Nice to meet you too, Dylan,” I said. “I’m not sure if my boss would let me have that much time away from the office.”

Dylan smiled, “It’s only one day per month, and we’ve never encountered a business that won’t let someone in their ranks mentor. 

It’s all part of being a good corporate citizen.” “I’ll think about it,” I said, non-committally. 

Ms. Hoden beamed, “Oh, I’m sure Cynthia would be more than happy to let you mentor, Heather.” She pointed at a seat between her and Dylan, “Please have a seat. 

We’ll eat first, then Mr. Donovan will say a few words and then you’ll be up!” Servers brought out plates with slices of ham and turkey along with mashed potatoes and a salad. It was tasty and all, but I was hoping for steak. 

I pulled out my speech notes and started going over them, when Ms. Hoden plucked them from my hand, tore them into several pieces and tossed the pieces on the floor, “Speak from the heart, Heather and you won’t need notes.” I just stared at the floor where the pieces were inaccessible under the table. 

I could get all unladylike and get on my hands and knees, but instead, I just sat there in shocked disbelief. “Those are my notes,” I said numbly. 

“You won’t need them,” insisted Ms. Hoden. She patted herself over her heart, “Everything you need to say is right here.” 

I looked out over the two hundred or so girls all nosily eating their free dinner and muttered, “No. Everything I need to say is now on the floor…” 

Ms. Hoden then walked up onto the dais and adjusted the microphone down to her, “Greetings everyone! Thank you so much for coming and making tonight’s dinner a great success. 

We are fortunate to have two speakers tonight. One many of you know – one of the wonderful mentors, Mr. Dylan Donovan. 

Our guest speaker is Ms. Heather Stephens, lead programmer for the Xantek Corporation.” 

There was a ripple of applause and then Ms. Hoden pointed at Dylan and said, “Mr. Donovan?” While Ms. Hoden was on the dais, I was trying to snag one of the pieces of my notes with the heel of one of my shoes. 

I almost slipped out of my chair, so I sat back up straight and gave up on the effort. I closed my eyes and tried to go over my speech in my head. The speech I was up until almost one in the morning trying to write. 

I was concentrating so hard on remembering my speech that it wasn’t until I noticed some laughter from the audience that Dylan had said my name at least twice, expecting me to come up to the dais. 

I gave the audience a deeply embarrassed smile walked up to the dais and took the microphone from Dylan. 

He had adjusted it back up and so I adjusted it back down. 

To the audience, I said, “Hello, everyone. I’m very honored to have been asked to speak to you all tonight. 

I had a great speech prepared for you, but Ms. Hoden tore it up and threw it on the floor, so I guess we’ll just have to wing it.” 

The girls in the audience gave a knowing laugh. 

Apparently, Ms. Hoden tortures all her guest speakers that way. I cleared my throat, resisted licking my lips, and started in, “Right now, there’s a big scramble to recruit women into the computer industry, and the industry is scratching its head wondering why it’s so hard to find women programmers. 

But the answer is easy. Compared to men, only a few women pursue computer science because in large part, as girls they just weren’t interested. 

I think that’s changing because social media and computers just becoming a common part of everyone’s lives. 

“But why aren’t girls interested? 

Well, when I was in school, a lot of my friends thought computers were all just math and too complicated. 

And while it’s true that many computer science programs require a lot of math, once you’re in a job unless you work for NASA or some other science area, you really don’t use all that math, and for me, programming is a creative endeavor, not a technical one.” 

I managed to drone on for twenty more minutes before concluding with, “So, don’t just sit around waiting for someone to just hand it to you. 

Yeah, you could learn a computer language and apply for a programming job somewhere that is looking to fill opening management wants to fill with a woman, but it will be much more satisfying to yourself as well as to your employer if you’re not just a female candidate, but an excellent candidate.

 If you really want it, it will happen.” Ms. Hoden joined me on the dais, and I handed her the microphone. She said, “Thank you so much Heather for those inspirational words.” 

She motioned that I should return to my seat, which I gratefully did. She started talking about something, but I didn’t really listen. I was just glad my antiperspirant was working overtime. 

As I sat down, Dylan said, “Interesting speech, Ms. Stephens. I liked your overall theme of hard work. That’s what I try to inspire in the girls I mentor.”

 I smiled weakly at him, “Thanks. And you can call me Heather. No need to be so formal.” Dylan smiled at me, “When this meeting wraps up, would you like to join me for a drink?” 

I didn’t want to and got flippant, “Will both of us fit in one of those little glasses?” Dylan smiled slightly, “Not only smart but a sense of humor, too. 

I like that. So, is that a ‘yes’?” I asked myself, what would the new all-woman Heather say to an attractive gentleman who offers her a drink? As long as it doesn’t involve removing my panties, I guess it wouldn’t hurt. 

I said, “Sure.” I just wished I had the excuse that I had to get up early to go to work the next day, but it was Saturday. Dylan smiled again, “I know a great little place not too far from here.” 

I returned his smile, “I’ll just follow you over there.” Dylan shook his head, “Oh, no reason to take your car, Heather. Just ride over with me, and I’ll bring you back here after we’ve had our drink.” 

I mumbled a quick reply, “Uh, well, I guess that’s okay.” 

After saying our farewells to Ms. Hoden, we left the Convention Center and got into Dylan’s Audi. We drove mostly in silence, and I was surprised we didn’t really go very far. 

It was just crazy for me to agree to go out for drinks for several good reasons. 

I’m not much of a social drinker, and I have no business going on dates, even for a drink, with men. 

We arrived shortly after leaving the Convention Center, and Dylan led me to a secluded table. The waitress took our drink order and left us alone for a few minutes. Dylan smiled at me and surprised me with a confession, “Actually, I had an ulterior motive for asking you for drinks. 

No, don’t look at me that way. I didn’t mean anything bad. What I meant was, was that I wanted another chance to twist your arm a little and to speak with you about becoming one of our mentors.” I sighed, “I’ll ask my boss about it. She’s keeping me pretty busy, so I don’t know what she’ll think about it.” 

Dylan expanded on it, “Well, it’s very rewarding, both for you and the girls. I think the girls would like having a woman mentor, especially one that’s as young and attractive as yourself. They learn, you learn. 

It’s a great program.” 

“I’ll ask!” I said lifting my arms in surrender. 

“Thanks,” seeming quite sincere, “I think you’ll enjoy it.” The waitress brought our drinks to us, and Dylan lifted his glass and said, “Cheers.” 

Dylan set his glass down after I had taken a sip of mine, and his hand rested against mine. 

He asked, “I was also curious if… well if you’re busy tomorrow night. I know it’s short notice, but…” His voice trailed away. “Well, I…” 

I started to say. “I know it’s not much notice, and we just met and all. I understand if you have something else going on. I was in the mood to go to a movie and I thought I’d ask. 

A movie, then something to eat. Nothing fancy,” he looked at me and shrugged his shoulders. Saturday night is usually my gaming night when I get online with guys who also don’t have girlfriends and still only know me as Harry. 

I said, “Well, I…”

Dylan smiled at me and just went on, “I’ll pick you up at six, Okay?” He took out his smartphone and continued, “Let me put your address and phone number into my phone.” He stopped with his fingers poised over the glowing virtual keyboard. 

His forwardness kind of took me by surprise and without thinking, I rattled off my number and address. 

Dylan flashed me a broad grin, “Thanks! I look forward to seeing you tomorrow evening!”

I woke up and looked with one bleary eye at the alarm clock. It was a quarter to ten. Half the morning was already gone. I closed the bleary eye, smiled, and nestled deeper into my bed, enjoying the cool feeling of my satin nightie. I just love Saturday mornings. 

I have ever since I was a little girl… uh… bo… uh… um… kid. I tried not to let my momentary bout of gender confusion spoil this glorious feeling of a near-perfect Saturday morning. 

I rolled over on my side and smiled to myself as I snuggled into the bed. It was finally Saturday. I didn’t have to go into the office today. I was completely free today. 

I didn’t have to do anything. Except go on a date with a man. 

My eyes suddenly popped open and a cold chill ran down my spine as I remembered that I had a date – a date with a man. I sat up in my bed, no longer feeling like lounging. I slapped my forehead a few times with the ball of my palm saying “Stupid!” each time. 

Why did I say yes? I frowned as I realized it was because he was irresistibly charming, and the new totally feminine Heather was caught up in it. My whole Saturday was suddenly ruined. 

I’m sure if I were an actual female, I’d be excited at the idea of going on a date with Dylan. 

He’s very handsome, charming to a fault, and has a wonderful sense of humor. But, I could tell he was used to having his way with women. I tossed my legs over the side of the bed stood up and walked to the bathroom. I looked at myself in the mirror and frowned at my image. 

My hair was a mess, and I wondered if Dylan would still ask me out if he saw how I looked without makeup. 

I looked through my closet. I frowned. I had only one shirt from my boy days. 

A t-shirt that said “Honey Badger Don’t Care” with a picture of the animal. There were skirts, dresses, various tops, and women’s jeans.

 What should I wear for a first date? I doubted Dylan even owned a holey t-shirt and cut-offs, but if I wore jeans and a tank top, would that be too casual? Even if he was casual? An evening dress seemed a bit overkill to me for a movie date. 

I decided I should probably get some expert advice. I picked up the phone and punched the buttons. A moment later I heard a sleepy, “Hello?” “Jennifer?” 

I said into the phone. Silence for a few moments, then a still sleepy voice asked, “Heather? You’re up early.”

 “It’s after ten,” I said. I hope I didn’t piss her off, “Sorry. I thought you’d be awake.” 

“It’s okay,” Jennifer whispered into the phone. “I should probably get up and start breakfast. I just don’t want to wake Nick up yet.” 

“Oh! Sorry!” I said sincerely. I keep forgetting Jennifer has a life, unlike me. 

“No, it’s fine,” she continued to whisper. “What’s up, girlfriend?” 

“I need some advice,” I said. 

“I have a date tonight and…” 

“You have a date?” asked Jennifer with genuine excitement in her voice. 

“I thought you probably liked guys. Who with? Details, girl!” I frowned at the phone, “Well, don’t read too much into that. I’m going out with Dylan Donovan. He’s with…” Interrupting, Jennifer said, “Oh, I definitely know who Dylan Donovan is! 

He’s really hot. I’m impressed, girl. Dylan only dates women who are the most beautiful and desirable.” “He must have forgotten his glasses last night then,” I said, feeling a bit self-conscious. “

Are you serious? Heather, I don’t know what all you’ve done recently, but with your new hair and attitude, you’re shouting confidence. 

You had the looks before, but now, you’re going to have to fight guys off with a stick.” Sarcastically, I said, “Well, that’s number one on my bucket list.” 

Jennifer giggled, “I guess you can check that one off!” I shook my head uselessly at the phone, “What I need to know is, what do you suggest I wear?”

Jennifer said, “I think you have a good style sense, so just following your instinct should be enough, but I will suggest you wear a dress or at least a skirt. What kind of date is it?”

 “A movie, and then dinner,” I said. “He said nothing fancy.” 

“My suggestion for a dress or skirt still holds,” said Jennifer. “A nice casual dress in a light color or maybe a floral print. Stay away from black. You want to look nice for him, even if he underdresses some.”

 “Okay, thanks,” I said. “I may have to go shopping today then. 

All my dresses are business or more formal.” Jennifer laughed, “Yeah, don’t wear a dress you’d wear to the office. The weather is nice; get a sundress. It’s casual and still a dress.” 

“I’ll look for something like that,” I agreed. “I just don’t want to screw up.” 

“You won’t, hun,” she seemed confident. “I still feel bad about that double date I set up with you. That went bad, but I’ve heard Dylan is very nice. Just… um…” Her voice trailed away. 

“Just what?” “Just be careful,” she said. “He’s nice, but he also knows exactly how to push our buttons. He’s a real charmer. 

If you’re not careful, your panties will be on the floor before you get through his door.” 

I grimaced, “Well, that’s not going to happen. I’m not going to his place, and he’s not going to mine. I don’t even know why I told him I’d go out.” Jennifer giggled. Her laugh was so disarming and delightful, “You like him; that’s why.” 

“No I don’t,” I said quickly. “Oh yeah, right!” laughed Jennifer. “Hey, I need to go. Nick is awake. Let me know how it goes tonight.” “I will,” I said and then hung up. I had to ask myself, do I like Dylan? Is that why I said yes? 

For the new, confident Heather, he is someone a woman like her would date. But seriously, I can’t date a man, even if he is adorable. Did I just call Dylan adorable?

I ate lunch a little early, just a tuna sandwich so I could be sure of having enough time to find what I needed to wear for my date. I shook my head thinking to myself about the effort I was putting out for a date that I should have turned down in the first place. 

I checked myself out with a quick glance in the full-length mirror. It felt good to just wear jeans a tank top and sneakers. The jeans were a little tight, and I had to make sure everything was tucked in well in front. I went light on the make-up.

 At first, I wasn’t going to bother, but I just couldn’t bring myself to outside without some makeup on. 

I had just exited my apartment, when coming up the stairs was my next-door neighbor, Jerry. I’d managed to avoid him the past week or so. He was carrying some grocery bags, so I hoped he needed to hurry inside with them. 

“Well, well!” said Jerry with a broad smile. “Look who it is! How are you doing, Heather?” 

“Hey, Jerry,” I said smiling weakly. “I’m doing good. It’s Saturday, so that helps.” Grinning, Jerry said, “I hear ya.” 

He looked at me up and down quickly and then said, “Hey, I like your hair! Looks good!” He looked me up and down once more and added, “You’re looking real good.” 

I smiled at him, “Thank you. I thought I’d try something new with my hair.” Jerry smiled back, “Sometimes new is better.” 

“True,” I smiled. “Well, I need to go do some shopping.” 

Jerry nodded and said as he started fumbling for his apartment's key, “Have a good day.” 

I started down the stairs when Jerry stopped me, “Hey before you go… um… I… I… was just curious if you’d like to go out sometime? 

My offer I made a couple of weeks ago to go for a few drinks is still good.” 

I forced a smile, “Sorry, Jerry. I have a lot going on today.”

Jerry quickly clarified, “I didn’t exactly mean today.” I just said in a non-committal way, “Sure. Sometime.” I started to down the stairs. “Just curious,” asked Jerry.

 “Are you busy tonight?” I stopped and turned to look at him. I shook my head, “Sorry. I already have a date for tonight.” 

Jerry nodded, looked down and coughed a short laugh, and said, “Maybe some other time, then.” 

I felt sorry for Jerry even though he can be obnoxious. 

I know he can never hang on to a girlfriend. It’s an odd feeling though, to know there’s a guy who wants to be with you. 

I’m not really sure how to feel knowing that the only thing on Jerry’s mind was his desire to fuck me. He really doesn’t care what I think of the weather, or what book I may be reading, or what TV shows I like. He just wants to have sex with me. 

He didn’t say as much, but having talked to Jerry back when I was just Harry, every attractive woman he saw he’d judge how good he expected her to be in bed. I never thought I was like that, but maybe most guys are, but it bothered me that I knew he saw me in that way. I hurried to my car. In less than twenty minutes, I was in the mall heading for my favorite dress store. 

I smiled and laughed under my breath. It was amusing to me that I had a favorite dress store. The sales girl who helped me pick my first outfits approached me with a smile on her face and dollar signs in her eyes, “Good morning, miss,” she said pleasantly. “I see you’re still doing your little bet. 

I have to say you’re really getting into it!” 

I smiled and looking around nervously responded, “Thanks, but let’s keep it our secret, okay? 

I lose if you give me away.” That last part wasn’t really true, but I really didn’t want it announced all over the store. Without skipping a beat or dropping her smile, the salesgirl said, “Most certainly. You’re just another of my female customers. 

I have to admit though, with your hairstyle and the confidence you’re showing, I never would have guessed, if I hadn’t already known.” “Thanks,” I accepted her compliment. 

Well, that was certainly good to know. 

“I have a feeling I’m going to win the bet,” I smiled at her. In my mind, I frowned. It’s only been a few weeks, and I don’t think anyone even remembers the bet. “Anything I can help you find?” asked the salesgirl, still smiling. 

I was beginning to wonder if she’d had surgery to make her smile permanent. “I sure hope so,” I said earnestly. 

“I need a light, casual dress. Maybe with a floral pattern? Something that says ‘I’m not at work.’” 

“Sure!” the salesgirl said as she started to turn. Over her shoulder, she said, “I believe we have some dresses right over here that you will like.” 

She led me quickly over to a section with racks of short skirts, dresses, casual, and beachwear. She pointed at two racks in particular, “I’m sure you’ll find something here to your liking.” 

“Thank you,” I said as I stepped up to the rack and started browsing through the dresses. The salesgirl stood by but didn’t try directing me to any particular dress. 

I guess she realized I was no longer lost when it came to selecting women’s clothes. I saw several that might work, but a short, white sundress with a blue floral pattern caught my eye. It didn’t have spaghetti straps or a neckline that would help expose my lack of boobage. 

It was also my size and the price was right. I pulled it all the way from the rack and held it up in front of me. The salesgirl said, “That’s a very nice dress. You’ll look very pretty in it.” 

Still holding it up in front of me, swaying back and forth, “You really think so?” It was a stupid question of course. I could hold up a burlap sack in front of me and she’d say it looked great if it would mean a sale. 

“Yes! It looks great. Would you like to try it on?” she pointed in the general direction of the dressing rooms.

Smiling, I said, “Yes, I would.” I walked quickly over to the dressing room and found an empty stall. 

I took off my jeans and made sure everything was still secure. I then removed the shirt and slipped into the dress. I suddenly felt so feminine. The dress was light and the skirt swirled about my legs as I turned to and fro. I even giggled with delight. 

I stepped out of the dressing rooms, and the salesgirl was still standing there making sure I didn’t run off with any merchandise. Smiling broadly, she said, “Very pretty!” I smiled back at her and said, “I’ll take it.”