Dress Code - Dare To Wear Dress - Chapter 7

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David laughed, “Of course not, little darlin’. 

All macho guys wear little miniskirts, high heels, and perfume!” He laughed again, “If you’d spent as much time as I have watchin’ she-male videos and searching the internet for pictures and shit, you’d be able to spot a tranny from across the room, too.”

 He slid his arm from the seat down around my shoulders. I pushed his arm away and again insisted, “I’m not a she-male!” 

“Are you not a guy dressed as a woman?” David asked with a smirk. Before I could say anything else, he continued, “My wife and I haven’t done anything in over a year and ever since I discovered trannies on the internet, I’ve been dying to meet one. Y’all are supposed to give the best blowjobs around. 

In fact, y’all just can’t wait. I bet right now that you can’t wait to find out just how well-hung a stud I really am!” He started to unzip his pants. I suddenly felt like throwing up. I held up my hand in a gesture meaning “Stop!” I explained frantically, “You’ve made a huge mistake! 

I’m not a she-male. I’m dressing this way because of a bet at work, not because I like it! And, I’m definitely not giving you a blow job!” I opened the car door. 

David reached around me and shut the door. The guy’s got some muscles, I’ll give him that. He was persistent, “You know you want it, baby.

You know you can’t wait.” In a quick motion, David pulled the top of his pants down, and then pulled down his underwear, exposing an impressive appendage. 

I struggled against his strong hands, but I couldn’t break free. In an accusing tone, Jennifer shouted, “Richard! Did you know about this?” 

“Know what, Honey?” Richard asked innocently. 

“Did you know that David wanted to go out with Heather just because he thought she was a guy?” I managed to get the car door open again, and as I was trying to get out, Richard said, “Well, yeah. David took one look at Heather and knew she wasn’t a real woman. 

He said he wanted to go out with her, and I said I knew the real girl she was with. I told him that if I asked you to go out maybe you could be persuaded to talk your she-male friend into going on a double date.” 

Jennifer suddenly looked furious as she shouted, “You asshole! You weren’t really interested in me? 

You just wanted to get Heather go to out on a date with your gay friend?” David finally let go of my hand as he turned to address Jennifer. “Excuse me?!” he bellowed. “I am most definitely not gay. I’m married with two kids.” “You could’ve fooled me!” I shouted back through the car’s window. 

David started to get out of the car. As he was doing so, Jennifer shouted at Richard, “How dare you! I thought you liked me!” 

Richard, looking like he’d rather be somewhere else said, “I do like you, baby. I enjoyed tonight. Even though I’m married now, I wouldn’t mind going out with you every once in a while.” Jennifer just stood there and cried. 

David came around the car and stood in front of me, “Look, I didn’t mean to come on so strong about it. I just wanted to let you know that I knew you were not a true female. 

Don’t get me wrong; I think you’re a beautiful woman. I’d find you attractive no matter what. But lately, I’ve become obsessed with trannies. 

Relations between me and my wife have gotten stale, and I was just looking for a girl with something extra to spice things up.” 

I suddenly felt incensed about the whole thing. I didn’t want to date David or any other guy for that matter, but it pissed me off that he was going to make me the “other woman” just so he could live out his homo-erotic fantasies. 

I shouted, “You asshole! When did you plan on telling me you were married, huh? 

And besides, just because a guy puts on a dress doesn’t mean that the only thing she wants to do is give losers like you blow jobs! I want to be treated just like any woman, not like one of your perverted sexual fantasies!” I turned away from David and took a few steps towards Jennifer. I took her hand and started to lead her away. I said, “Come on, Jenn. Let’s get a cab. I’ll take you home.” 

David continued, “Look, I’m sorry. I thought all she-males were just crazy for sex. You don’t have to call a cab. We’ll take you home.” 

I shouted back, “No way! And for the last time, I’m not a she-male. I’m a… I’m a… woman.” 

  The taxi pulled up to Jennifer’s apartment complex. I turned to Jennifer and said sincerely, “Here’s your apartment. I’m really sorry the evening ended up so badly.” Jennifer shook her head, “It’s certainly not your fault. If anyone, it’s mine. 

I should have known better than to think Richard was still interested.” She started to get out of the cab, and then she turned back to me and asked, “Would you mind terribly coming up to my apartment with me? 

I’m too upset to go to sleep right now, and I really don’t want to be alone right now.” Wow. Jennifer is inviting me up to her apartment! It’s just too damn bad she’s only doing it so she can have a girlfriend to commiserate with, “Sure, okay. I don’t feel much like sleeping right now either.”

I paid the taxi driver and started walking in silence with Jennifer towards her apartment. It was a surreal moment. Here I was, walking beside one of the most desired females at the office, and I couldn’t even so much as hold her hand. 

After we entered her apartment, Jennifer broke the silence by inviting me to sit on the couch. 

“Do you want anything to drink?” she asked. I shook my head, “No thanks. I’m fine.” She stood there, still looking wonderful despite the evening, and asked, “You sure? Not even a Coke? Water? Milk? 

I have some green tea.” I gave in, “If it’s no bother, I guess I could use a Coke.” She smiled, “No problem. I’ll be back in a minute. Feel free to turn on the television if you want.” 

I figured she’d be back in about thirty seconds, so I just sat there. A couple of minutes ticked by, so I turned on the TV to see what was on. 

A moment later, Jennifer returned, dressed in a peach-colored satin camisole and matching shorts. She carried a Coke can in each hand. 

As she handed me the can, she said, “Sorry for taking so long.

I just had to get out of those stinky clothes.” She flopped down on the couch next to me and ran her hands through her long, damp hair. “Oh God! What a nightmare! Everything started off so great, and then…” 

She just stared at me a moment. Finally, she asked, “Just what the hell was up with that guy, anyway?” 

She laughed and looked at me, and then lowered her voice in an attempt to sound like David, “You’re a she-male so let’s fuck!” She laughed again and in her normal voice said, “Isn’t that just so romantic?” 

“It still creeps me out just thinking about it,” I said with a visible shiver. Jennifer just sat there a moment, staring into her hands. She turned to face me, and I could see the tears welling up in her eyes. She started to cry as she said, “I just don’t get it! How could he do such a thing to me?

 He’s married now and he gets my hopes up by asking me out. Ohhh! That asshole!”

I held out my arms and she fell into me and let me hold her as she literally cried on my shoulder. I patted her back and stroked her hair and tried to say soothing and comforting things, “I’m here for you Jennifer. 

Go ahead and cry get him out of your system. At least, you found out he’s a slimeball before you went out with him again.” Jennifer pulled away a little and looked at me. Our noses were only an inch apart. 

I could feel her warm breath on my face, “I mean, not only was he married and led me on, but he used me so his weird friend could get to you! I feel awful for dragging you into it.” I touched my forehead to hers and put my hand on her cheek as I consoled her, “Oh, it’s not your fault. 

You had no way of knowing they were a couple of creeps. Honest, I don’t blame you. 

Men are scum, right?” Oh God, our lips were so close! What was left of her perfume filled my nostrils. She leaned back into me and gave me a big, girlfriendish hug.

 As she held me close, Jennifer said, “Thank you for being here. I needed someone to talk to.” “I’m here for you Jenn,” I said sincerely as I stroked her hair. 

Jennifer pulled herself closer to me as she said softly, “I appreciate it. I’m so glad you’re here with me tonight. I’d hate to be alone right now.” 

I leaned in closer to her, “I’m glad I could be here for you, Jennifer. If I were a guy… um, I mean, as a guy, I’d never mistreat you like that.” “All guys say that,” Jennifer’s eyes bored into mine. She leaned in closer.

 “But I understand,” I whispered. “I’ve been there.”

 “Did I ever tell you that you’re cute?” she asked. 

“Yes, you did,” My voice trailed away as she parted her lips, leaned closer to me, and closed her eyes. And then our lips met. A hot flush rushed through me as I pressed harder into her and put my hand behind her head. 

I couldn’t believe I was kissing Jennifer! As she fell backward on the couch, my tongue found hers, and I suddenly found myself lying on her. I kicked off my shoes, and then, she wrapped her legs around mine.

Jennifer was a wild woman. I began to doubt that I could hold on. 

As we struggled on the couch, my wig fell to the floor. Jen’s emotions must have been driving her as she kissed me with a passion that even to me seemed excessive. 

She pulled off my top and I wriggled out of my miniskirt. I found my bra pressing against Jennifer’s breasts through her camisole. 

I don’t know what it was doing for her, since it wasn’t doing anything for me, but she moaned softly. However, pressing my silky panties against her satin shorts was doing amazing things for me. 

The sensation was incredible and Mr. Happy was just busting with joy. Our passions rose to a crescendo of kissing and fondling. Jennifer suddenly reached up and pulled my panties down and slung them across the room. 

Breathing hard and blood pounding, I became a member of a very exclusive club…

When I awoke, the sky was just starting to lighten. At first, I was disoriented as I wasn’t in my bed. 

Then the memory of last night flooded back into my mind. I sat up slowly, supported by one arm, and looked over at Jennifer. She was sleeping soundly, her hair wildly disheveled. She uttered a little groan and rolled over. 

I carefully eased out of the bed so I wouldn’t disturb her. 

With the notable exception of coming to Jennifer’s apartment, the night was a total disaster. I hope I’m never in such a nightmare again. I looked again at the sleeping girl. Her curves were still quite prominent under the sheets. I smiled at her form for a few moments. It was probably a shitty thing to do, but I thought it would be best if I left before she woke up. 

That’s what I did with the two girls I slept with back in Wink. 

They both had told me that they had hoped I’d stayed there, but that would have been really awkward with their parents in the next room. I started looking for my clothes and had a sudden panic attack when I couldn’t find them either in Jennifer’s bedroom or her living room. 

After sweating for a minute, I finally realized I had come to her apartment as a woman. I looked down at the floor in the half-light of dawn that was trickling through the windows trying to decide whose panties and bras I was looking at. 

Finally, I found all of my clothes picked up my wig and purse and started to head out the door to call a cab. I got as far as putting my hand on the doorknob when I realized I still needed to look halfway presentable, even to the cab driver. 

Back in Wink, a few minutes’ walk took me back to my house and all I needed was a pair of pants. Today, I couldn’t allow myself to be so lax. I quietly entered Jennifer’s bathroom donned my wig and adjusted it. Looking in the mirror I was glad I didn’t try to go out of the apartment. 

I definitely had that “freshly fucked” look. I hoped Jennifer wouldn’t mind when I borrowed some of her foundation. I cleaned away the smudged mascara and otherwise cleaned up as best I could. 

I hoped I didn’t look like some hooker leaving her John. Fifteen minutes later I was in a cab heading back to my apartment. The cabbie gave me a knowing smile but otherwise didn’t say anything. 

  It was noon when I finally looked over at my clock. I groaned. I hated waking up so late. I dragged myself into the shower to see if I couldn’t wash last night off. I washed my wig in the kitchen sink. 

I put on a T-shirt and shorts and absolutely no make-up. This was going to be a guy weekend even if it meant camping on the couch the whole time. 

I really thought I’d get a call from Jennifer but not one peep all weekend. I guess I should have called her, but I didn’t know what to say. It was supposed to have been a big night for her and instead, it was a cluster fuck. 

I popped some microwave popcorn for lunch, grabbed a beer, fell back onto the couch, and began a righteous, weekend-long case of some serious vegging. 

Even though there were no wrinkles, I smoothed my skirt after stepping off the elevator. As I approached the office area, I saw Jennifer shuffle a few papers on her desk before busying herself with her nails. 

I smiled at her and said with as much feminine lilt as I could muster, “Good morning, Jennifer!”

 “Good morning, Ms. Stephens. Oh, wait before you go in.” 

Taken aback, I said, “Ms. Stephens? What happened to ‘Heather’?” Jennifer avoided looking at me in the eye as she said, “I am so sorry for Friday night. That was over the line and I’m sorry.”

Feeling puzzled, I said, “Jennifer. It’s okay. We’ve discussed it already. There’s no need to apologize. You had no way of knowing those guys were total jerks.” “Oh, I don’t mean that.” 

She finally did look directly at me, “I meant what happened afterward.” I couldn’t help but let out a short laugh, “Afterwards? Jenn, there’s absolutely no reason to apologize for that! In fact, I’d say it more than made up for the early part of the evening.” 

“No, no. You’re trying so hard to be a woman, even beyond that silly bet, and you’re doing so great! And like I said, you’re already like a sister to me... and… and… like, you don’t fuck your sister! I’m not a lesbian. You must think I’m awful!” She turned away from me and wiped a tear away. I just stood there totally dumbfounded for a moment, not sure what to make of her comments. Touching her shoulder I said, “Jennifer. I would never think you’re awful! 

Especially over Friday night. I rather actually kinda enjoyed it. Actually. 

You were great. You’re a gorgeous woman Jennifer. You weren’t with Heather that night. 

That was Harry. Good ol’ non-sister Harry. You’re definitely not a lesbian. I mean, Harry could spot one a mile away.” 

As I tried to stop rambling, I thought that no, I wouldn’t be able to spot a lesbian, thinking of those twins and the cheerleader back in Wink. Jennifer tried to smile, “Oh, Heather! Thanks for trying to make me feel better, but I screwed up, and trust me, I will never let that happen again. 

Ever! I value you too much as a girlfriend, and I know how much it means to you to become a woman.” She then added, “Oh, and Mr. Murphy is waiting for you.” She pointed to the door to the offices. 

What the hell just happened here, I thought, as my brain went into overload. 

I told her, “Jenn… we… we uh, like really need to talk. I mean like seriously talk. You said Murphy is waiting? Waiting for me?” 

At Jennifer’s nod, I started hurrying to the door. I turned back to her, “We’ll talk…” 

I really didn’t want to see Murphy at all, but keeping him waiting would only make matters worse for me. I pushed the door open and entered the office area.

Murphy was talking to Ms. Rogers as I entered the room. She was looking a little pale and I knew this couldn’t be good. Murphy turned towards me with the nastiest smirk I’ve ever seen. “Well, well, Ms Stephens. 

So nice of you to show up this morning. I just dropped by to see if you had the specs ready for my review.” Wearing my best deer-caught-in-the-headlights expression I said, “Uh… uh… what specs, Mr. Murphy?” 

Murphy contorted his face into an exaggerated frown, “The specs for the IOTEK project, Ms. Stephens.” He glanced at his watch, “You’ve had all weekend to prepare them.” 

“I.. I.. nobody said they were due today,” I tried to maintain an even feminine tone to my voice. 

“Actually I thought I had at least until Friday…” To be honest, I don’t remember a specific date being set yet. Suddenly looking indignant, Murphy folded his arms and said sternly, “Are you saying you did nothing on the specs this weekend? 

Ms. Stephens, this is not how we get things done around here. 

I know you’re new… so new in fact that H.R. has no record of you. I’m sure that’s an oversight. But to the point, we’re professionals here, Ms. Stephens, and as such, I expect total commitment until a project is completed! Are we clear on this?” “Yes, sir,” I said quietly. “Good. Don’t disappoint me again, Ms. Stephens. 

I’ll expect those documents by the end of business Thursday. Good day.” He then fumed past me and exited to the lobby. Looking very unhappy, Ms. Rogers turned to me, wiggled her finger in a “come here” gesture, and said, “Heather. In my office. 

Now.” The room was silent as everyone was looking at me as I stepped quickly into Ms. Rogers’ office. 

She shut the door behind me and sat down at her desk. She seemed very agitated. She pointed at the chair in front of her desk, “Sit down, Heather.” Before I could be seated, Ms. Rogers stated, “We have a problem, Heather. A big problem. Ralph has been sticking his nose around. He checked up on you in H.R. Of course, there is no Heather Stephens in this company.

company. Fortunately, he’s too single-minded to notice that there is a Harold Stephens.” 

“I’m sorry, Ms. Rogers,” I said sincerely. “I’ll cancel the bet. I’m sure everyone will understand. Except maybe Ann.” Ms. Rogers held up her hand and said, “No! No. It’s too deep now. 

There’s a multi-million dollar deal and potential for more riding on this deception. We have to do something.” I have never seen the normally stoic Ms. Rogers in a near panic before, and it was causing me to panic as well. “You heard Murphy, Ms. Rogers. 

He’s out to get me – at any cost. 

He’s trying to make me fail so he can either fire me or take me off the project.” 

“If he finds out you’re not a woman on top of that, then my goose is cooked as well,” Ms. Rogers just stared blankly at her computer screen. She looked over at me, “I’m not blaming you, Heather. 

I should have stopped that stupid bet at the get-go. Ms. Hoden probably would have liked you standing up to Ralph’s bad idea anyway, even if you hadn’t been a woman at the time. Then again, who knows?” I started to stand up, “Look, I’m about to hurt a lot of people. I’m just going to resign and save everyone a lot of hassle.” 

Ms. Rogers shook her head and motioned for me to sit down, “No. No, don’t do that. I don’t want Murphy to win.” She picked up her phone handset and punched a few numbers. “Hi, Jane. This is Ms. Rogers in I.T. 

Can I come up and talk to Mr. Keyes for a few minutes. It’s urgent. No, it really can’t wait until after lunch. Thank you. I’ll be right up.” She looked over at me and said, “Get up. You’re coming with me.” “Where? I mean why?”

 “We’re going to go tell Mr. Keyes how the cow ate the cabbage…” 

  Ms. Rogers shut the door to Mr. Keyes’ office after I entered. She motioned for me to sit next to her in front of the desk as she took a seat across from Mr. Keyes.

Mr. Keyes folded his hands together in front of him on the desk as he looked earnestly at Ms. Rogers, “Cynthia, I understand you have some urgent business to discuss. How can I help you?” 

Ms. Rogers took a deep breath and sighed, “It has to do with both Mr. Murphy and Ms. Stephens. 

There are two issues, actually. The lesser one is that Ralph is coming down pretty hard on Heather. To the point, where I think he wants her to fail. I…” 

Mr. Keyes leaned forward and rested his chin in his hand, “You have proof of this, Ms. Rogers? That’s a serious thing to accuse someone of Mr. Murphy’s stature in the company.” Ms. Rogers nodded, “Yes, I know. This morning he was demanding the specs for the IOTEK project, knowing full well that Heather wasn’t expecting to have them finished this week, much less today. 

He also requested Heather’s employment records from H.R.” Mr. Keyes shrugged and said, “I’m not following you, Cynthia. Mr. Murphy is senior management. It’s not unusual for him to check employee records.” 

Ms. Rogers swallowed audibly before saying, “Well, he discovered that Heather Stephens isn’t on the payroll, Mr. Keyes.” Mr. Keyes sat abruptly back in his chair and said harshly, “What do you mean, not on the payroll? 

Are you keeping her in the basement with a red stapler?” Ms. Rogers shook her head and explained, “No, Mr. Keyes. Heather is actually on the payroll but under the name Harold Stephens.”

 “Now I really am confused,” blustered Mr. Keyes. “Are we talking about a simple misspelling that H.R. could correct without my involvement or just what are talking about?” 

He looked at me with an extremely annoyed expression. “What it means is,” Ms. Rogers hesitated a moment, then continued, “What it means is that about two months ago, we hired a nice, talented young man named Harry Stephens. And then last week, he…”

This was not going well and I was sure both me and Ms. Rogers were about to be fired. While my better judgment was screaming at the top of its lungs “Don’t do it! Keep your fat trap shut!” 

I interrupted Ms. Rogers, “And then last week, I came out to Ms. Rogers about my gender dysphoria and how I wanted to start my real-life test even if all the paperwork wasn’t completed. 

Not only is Ms. Rogers a brilliant systems analyst, but she’s the nicest and most gracious manager I have ever worked for. She said I could go ahead and that the paperwork would catch up later.”