Urban
patreon
Dress Code - Dare To Wear Dress - Chapter 2
🕑 Added 2024-09-23 14:08:15 +0000 UTCOTHER CHAPTERS | ALL STORY LIST
It was two o’clock Saturday afternoon as I wheeled my car into the parking lot of Thelma’s Glamour Emporium.
I had tried on most of my new clothes earlier in the day. The clothes all fit, but I just looked like a geek in drag. Thelma’s was a small unit in a small shopping center.
I was mortified to see at the bottom of her sign the words “Crossdressers Welcome.”
I really didn’t want to walk in there. However, if I wanted to pull this off, I was going to need some really major help.
As requested, I brought an outfit in a small suitcase which included a navy blue skirt and jacket, light blue blouse, slip, panties, bra, pantyhose, and black pumps with three-inch heels.
I’d tried the heels on this morning and almost fell through the sliding glass door at the rear of my apartment. Also as requested, I’d shaved real close before coming over. I was also requested to shave my armpits and legs if I wanted the full effect.
I’d bought a women’s razor for the occasion.
I hadn’t really even gotten started and ‘being a woman’ was already being a lot more trouble than I would have thought. Finally, I took a deep breath, stepped out of my car, and boldly walked through the door.
I’m not sure why, but I expected to see leather outfits, chains, and bullwhips hanging on the walls. What I did see though, was a brightly lit, clean little shop, looking pretty much the way I’d expect a regular beauty shop would look like. I was alone in the front room. As the door shut behind me, a voice from the back room called out, “Just a minute!”
A moment later a middle-aged, but still attractive woman emerged from a hallway. “Good afternoon,” she said pleasantly.
“I’m Thelma. You must be Mr. Stephens. Please, sit down and tell me again exactly what it is you need.”
I rotated the chair around so that the back was to the mirrored wall and counter with a dizzying array of cosmetics and assorted tools and devices. I set the suitcase on the floor as I sat down I the chair.
I cleared my throat and cautioned, “Excuse me, I’m a little nervous.” Thelma nodded with understanding and said, “That’s quite alright. Would you like some coffee?
A soda?” I shook my head, “No thanks, I’m fine. I… I guess the reason I’m here is because I… well… I…” my voice trailed away and I felt my cheeks burning hot.
Thelma just stood there, leaning patiently against a wall.
Finally, I managed to say, “I would like for you to show me how to put on make-up properly, and hopefully, maybe you can show me a few things about how to walk, and carry myself as a… a… w… woman would.”
Thelma looked me up and down and nodded as she stood up straight and began walking over to the door. As she picked up a sign that read ‘Private Session’, she said, “I don’t think that’s going to be much of a problem.”
She paused as she put up the sign in the storefront window.
Then she added, “Now go in that little room over there and change into your panties and bra and we’ll get started.”
Nervously, I got up from the chair, picked up my suitcase, and walked into the changing room. I removed the suit and hung it on the convenient hook and ran my hand down it to try to smooth it back out. Then I quickly stripped down and slipped into the smooth nylon briefs.
They were just plain, white nylon panties, but I have to admit they felt very exotic. The bra was just uncomfortable.
I don’t know how you’re supposed to put it on, but I hooked it from the front and then rotated it until the hooks were in the back. Looking at myself in the full-length mirror, I said to myself, ‘This is never going to work.’ I opened the door and walked back to the chair.
Thelma motioned for me to sit. “Is this your first time to dress?” Thelma asked.
“Most of the guys who come here either want a glamour make-over for a photo shoot or a special date. Sometimes they want make-up tips.” “Yes,” I said, “until this weekend, I’d never even thought about putting on any articles of women’s clothing.”
Thelma started examining my face as she questioned, “That’s odd. Most guys figure out they like women’s clothes either in their early teens or even earlier.” Sheepishly, I explained, “Oh, I’m doing this because of a really stupid office bet.” Thelma stopped what she was doing and looked at me funny.
I continued, “That’s why I need to know how to put on make-up and stuff. I need to dress like a woman for at least a month.”
“What kind of bet was it that you lost?”
Thelma asked. “Oh, I didn’t lose it – at least not yet. The bet is to see if I can stand to do what women have to do at work for a month,” I then explained the bet further.
When I had finished telling her about the bet, Thelma said, with a tinge of anger in her voice, “I should toss you out on your ass right now, you little chauvinist jerk.
You think doing things as a woman is easy, eh? You’ve got quite a surprise coming.”
“Hey, I didn’t say I really believed that. I was just trying to stir up the conversation!”
Okay, so I did believe it, but just from what I’d had to do so far, I was beginning to feel I was wrong about it being easy.
Frowning, Thelma acquiesced, “Well, you might actually learn something out of this. From the looks of things, I’d say you’ve probably already spent more than you’ll make on your bet.” Nodding in agreement, “I think you’re probably right.”
Thelma suddenly took on a professional demeanor, “Well, let’s get this show on the road. Sit back down.”
As I sat down, Thelma busied herself arranging an array of brushes and cosmetics. As she turned to face me, she was holding a small jar of make-up.
She began, “Now, I’m not going to do a glamour make-over or anything like that. I’m going to instruct you on how to wear make-up the way most women do for a day at the office. First, I’ll just make you up so you can see how it feels, and we can get an idea of what you’re going to look like and find your problem areas.”
As she put a daub of make-up on her finger she said, “Most of the guys who come to me have been wearing make-up for years and love being pampered during a makeover.
The few guys I get, like you, who have never worn make-up before usually don’t like the way it feels at first or the way it smells, and so on.” She then streaked the daub along my cheek and started smoothing it in.
She was right. I flinched at the first touch, as it was cold and I didn’t like the smell.
I didn’t like the way the lipstick felt going on or its smell either nor did I much care for when she applied the mascara. I thought, ‘My God, how the hell was I going to be able to do this every day for a month?’
I hadn’t had make-up on for five minutes before I wanted to wash it all off. After using several brushes on my face, Thelma backed away and looked at me. She went over to a shelf with a wide variety of wigs, and picked a couple with shoulder-length hair.
She said thoughtfully, “Hmmm. Now we did this rather quickly, but still, I think we got fairly good results.” She then picked up one of the wigs she’d selected and placed it on my head and did a quick brushing.
“Now, don’t look in the mirror yet and go put on the rest of the outfit you brought, and then go take a look at yourself in the full-length mirror. Be sure to put on your heels, too.”
I wanted very much to look at the mirror, but I did what she asked and went back to the little room to put on the blouse and skirt. It bothered me that the wig hairs tickled my neck and shoulders. I didn’t bother with the pantyhose for now.
I hobbled over to the mirror again.
At first, I was afraid to look, expecting a complete monstrosity to stare back at me. What I saw surprised me.
Staring back at me was a fairly attractive woman. Thelma appeared in the mirror next to me and smiled, “Pretty amazing, huh?”
I nodded and she continued, “Make-up is a wonderful thing. Go sit back down and we’ll clean you up and we’ll start the make-up lesson.”
I just stood there for a moment in complete disbelief. I was certainly no Miss America, but I thought I looked just as good as most of the women in the office.
I thought I looked better than Ann at least, and I really hoped she would be very pissed off about that.
For the rest of the afternoon, Thelma went over the finer points of putting on makeup and showed me how to use something called a ‘gaff’ to hide my privates, care and feeding of my wig and proper female mannerisms. Pretending to be a woman was going to be tougher than I thought.
When I left to return to my apartment, I was wearing the suit, hose, heels, make-up, wig, and all. Climbing into the car meant sitting down carefully, carefully, and then swinging my legs inside.
The heels put my feet at an awkward angle to the pedals. I looked at myself in the rearview mirror.
I couldn’t believe what I was seeing. I studied my hands with the polished nails for a few moments.
I thought that maybe, just maybe, I was going to pull this off after all. One part of me was dreading Monday morning. The other part was oddly excited. Most of the drive home was uneventful, not counting when my foot slipped off the brake pedal and landed on the accelerator sending me blasting through a red light.
That’s all I needed now was to get stopped by a cop or be in a wreck. I spent the rest of the evening and most of Sunday practicing walking in heels, trying on all my outfits, and playing with my make-up. I was beginning to think Monday was going to be a walk in the park.
I fumbled around for the alarm clock and managed to knock it off onto the floor. I fished around for it on the floor, becoming increasingly annoyed that I couldn’t just hit the snooze button.
Finally, I grabbed the clock and set it back up on my bedside table. Bleary-eyed, I looked at the numbers glowing on my face. Five freakin’ thirty. An hour before I normally get up.
I groaned as I slid my legs over the side of the bed and sat there a moment, trying to wake up.
A deep sense of dread washed over me as I remembered why I had set the alarm early. I was going to have to go to work dressed as a woman!
I was so cock-sure Sunday as I literally pranced around the apartment in high heels and dresses feeling that spending the day like that would be a breeze, but that had been in private.
Now I had to face the very public world outside. Why did I ever make that stupid bet? I had shaved my legs and armpits, did my nails, and even plucked my eyebrows the night before. I ran my hand down my smooth legs. It felt so weird to not feel any hairs on my legs.
I looked at my hand with the pearl pink nail polish and winced. I dragged myself to the shower after grabbing my new bottle of apple-scented body wash I was going to use instead of soap. As I showered, I went over and over in my head all the tips and tricks I’d learned from Thelma. I really didn’t want to look like just some geek in a dress.
After the shower, I found the gaffe and wondered if I really wanted to use it or not. I decided I’d better. Going to the restroom was definitely not going to be much fun.
Not that it’s much fun to begin with. I pulled on a pair of powder blue panties and a matching bra, then sat on the end of my bed and started rolling up one leg of pantyhose.
As I slid the pantyhose up one leg, I shook my head at the memory of those movies where they show a guy fumbling around trying to put on pantyhose and winding up ripping it to shreds.
I took a few steps, marveling at how good it felt to walk on carpet in pantyhose.
I slipped the breast forms I’d bought from Thelma inside my bra. I walked back into the bathroom and spread my array of cosmetics across the counter top. I studied them for a moment then remembered I needed to shave first. So, I finished all my usual bathroom duties first. I almost used my regular deodorant, until I remembered the stick of Secret.
I studied the cosmetics cluttering up the bathroom counter. So much stuff… I braced myself and began to apply the foundation. I looked at my watch as I went along, thinking it was taking too long.
I was hoping this would become more routine as the days went by. I botched my eye makeup and had to start over.
I poked myself in the eye with the mascara brush. Jeesh! How can women put up with this crap every single day?! Did I just lose the bet before I even got to work?
I reminded myself that this would all become second nature in a few days. I hope.
I chose to wear my navy skirt and jacket with the light blue blouse with navy pumps. I stood in front of the mirror and I was dumbfounded by what I saw.
While not exactly gorgeous, I saw an attractive young woman staring back at me.
My God! Is that really me, I thought? I turned this way and that, striking various poses in front of the mirror.
I glanced down at the inexpensive woman’s watch I was wearing. I needed to be going or I was going to be late for work. I grabbed my purse and dumped my wallet into it, along with lipstick and various other items.
Then I headed out the door. As I was locking my door, Jerry, the guy who lived in the apartment next to me was just coming out. He looked at me quizzically and seemed excited, “Well, hello! I don’t remember seeing you around here before.” He was grinning a rather stupid grin.
As I dropped my keys into the purse, I responded, trying to sound as feminine as I could without going falsetto, “Hi. I’m just watching Harry’s apartment while he’s out of town.” Jerry just smiled as he stared at me and said, “Nothing against Harry, but I kinda hope he has to stay out of town for a while!”
I’m sure he’ll be back soon. I’m late for work.” As I turned away to head for my car, Jerry called out, “Wait! I didn’t catch your name!” Without stopping, I turned, “That’s because I didn’t give it to you.” I hurried on my way.
I walked down the sidewalk and around the corner. I didn’t want Jerry following me to my car. It occurred to me that I’ll have to say that ‘Harry’ loaned me ‘his’ car along with his apartment should anyone ask. I wondered how plausible that was. Would I buy it? I don’t know.
But, at least Jerry didn’t say, “Hey Harry. What’s with the get-up?” or something that showed that he recognized me. That was good. I went to my car and started to get in, and was caught by my tight skirt.
I have to remember to sit first, and then bring in my legs.
I put my foot on the accelerator pedal and rocked my foot back and forth. It felt weird to pump the gas wearing high heels, even though they were only two inches tall. Note to self… put my tennis shoes in the car for driving.
I started the car, took a deep breath, and pulled out onto Spring Creek Parkway.
After finding a spot in the parking garage, I got out of my car, slung my purse strap over my shoulder, and started walking toward the elevator. I was mortified to hear the rather loud clicking noise of my shoes on the concrete as I walked.
Whenever you hear that shoe-clicking sound, you know it’s almost always a woman, but this time it was me. I’m sure it sounded louder to me than it really was. Still, I hoped I’d soon not even notice it.
As I walked to the elevator, I concentrated on the feminine way of walking that Thelma had shown me. I hoped I was doing it right. The tight skirt made sure I took short steps. I was late, and there wasn’t anyone else at the elevator. As I rode down to ground level, I could feel a trickle of sweat roll down my back.
Walking through the first-floor lobby, I passed the snack area. Several guys seated at one of the tables turned to look at me as I went by. I tensed as I expected at any moment a roar of laughter and fingers pointing. Instead, I heard one of them comment about how good the ‘scenery’ was here.
I relaxed a little as my confidence shot up.
I know that the only magazine cover I’m likely to grace would be Mad Magazine; I still felt extremely gratified that a bunch of guys not only took me for a woman but an attractive one as well.
As I waited for the elevator to arrive, the confidence I felt began to dissolve into embarrassment, as I noticed that same group of guys continued to cast glances my way. I don’t think I was ever more glad to hear the chime of the elevator arriving.
I hurried inside and pressed the button for the twelfth floor. The elevator doors slid open. I just stood there, suddenly frozen in fear.
My early confidence had completely evaporated.
The door started to close.
Frantically, I punched the button to open the door, started to leave the elevator, and then, stopped again. I took a deep breath and clutched my purse strap so hard I started to dig my polished nails into my palm.
I took another deep breath and stepped out of the elevator.
I looked around and the only person visible was Jennifer, sitting behind the receptionist's desk, both behind the glass wall. She didn’t look up as I opened the big glass door and walked through.
Nervous, all I could think of was trying to make it to my cubicle. Jennifer looked up and asked, “Miss? Can I help you?” I stopped dead in my tracks. Wow. She doesn’t recognize me, I thought, as I turned around to walk back to her. “You don’t know who I am?” I asked somewhat lamely, trying to sound feminine. Jennifer wrinkled her brow as she studied me a moment then said, “No. Should I?” Smiling nervously, I said in a normal voice, “It’s me. Harry.”
Her jaw dropped and her eyes went wide as she stood up and looked at me as if I was from another planet, “No way! My God, Harry, is that really you?”
I laughed uncomfortably and said, “Yep, it’s me! What do you think?” Jennifer put a hand on her forehead as she laughed, “Oh my God! I don’t believe it!”
She stepped out from behind her reception counter, “Turn around, let me get a look at you.”
I did as she asked and she completed the once over, “All I can say is ‘wow’, Harry. Or I guess I should say Heather ‘cause you don’t look nothin’ like a Harry!” I asked, “So you think I look okay?”
I felt a trickle of sweat run down my inner leg. Jennifer laughed, “Har… Heather, every guy stopped here and asked if you had arrived yet.
They can’t wait to laugh at you. I really don’t think they’re going to laugh now.” I grimaced, “Well, I guess I’d better go face the music. I sure hope you’re right.”
She smiled and said in a reassuring way, “You look great! You really do. I mean, I can’t believe you make such a pretty girl!” “Thanks,” I said, as I started to turn to head toward the office area. Jennifer called out, “Hey, knock ‘em dead, Harry… ah, Heather.”
The office area was deserted when I entered. The only person I could see was Ann, Ms Rogers’ assistant, sorting out some papers on her desk. I walked up to her desk, and she stopped and looked up at me and pleasantly asked, “May I help you?” It was the first time she’d ever said anything to me in a pleasant tone. I hated trying to talk, but I tried my best to sound feminine without going too high. “Is Ms. Rogers here?” If there was anything odd about my voice, she either didn’t notice or was being too polite to say anything. Ann shook her head, “No, she was called into a meeting this morning. I don’t know how long she’ll be, but you’re welcome to wait. There’s coffee around the corner.”
I just stood there, savoring the moment. Ann was actually being civil to me. Finally, I let her in on our little secret, “Ann. It’s me, Harry.” For one brief moment, surprise crossed Ann’s face.
Then, she shrugged, looked back down at her desk and started rifling through the papers lying there, “I knew that. I was wondering how much longer you were going to try to fool me.” She looked back up at me and seemed sincere, “I am impressed though.
I’ll admit that you did a half-way decent job, but this is just the first day, sweetie. You have a whole month to go!” “I’ll take what you said as a compliment,” I said without humor, “and, you’re not a very good liar.”
I spun around and headed for my cubicle before she could say anything else. I was in the aisle of the cube farm, almost to my cubicle when Chuck popped out of his, head down and almost ran into me. He looked up, startled, “Oh! Excuse me! Are you trying to find someone?”
I just smiled and said, “Yes. Harry.”
“Sure. Harry’s little office is right down here,” He turned and led the way. I just couldn’t believe it. He didn’t recognize me.
“Here’s his cube. He isn’t here yet.”
He paused and looked thoughtful for a moment, then said with a laugh, “Actually, you might want to go back to the front and leave a message with Ann for Harry to reschedule your meeting. I really don’t think he’ll want visitors today!”
He chuckled again. In my normal voice, looking at him square in the eyes, I said, “And now, why would that be, Chuck?”
Chuck just stood there a moment with a puzzled expression. Then, his eyes went wide and his mouth fell open.
“Ha… Harry? Is that you? My God Harry, you actually went through with it! Holy shit, look at you!” Chuck leaned over the top of the cubicle wall and shouted, “Hey guys! Harry’s here! You’re not gonna believe this!”
Grinning, he stepped back from the wall, shaking his head while looking at me, he just shook his head, “Holy shit.” Reminding me of prairie dogs sticking their heads out of their holes, heads with puzzled looks started bobbing up from the cubicle walls.
Finally, they started finding their way over to my office.
Comments
Jerry
Heather is an absolute dove. Men can be so absolutely lost. I wish her the best. She is so courageous. All women are.
Brianna Demonet
So far so good! You're brave man Heather!
