Oscar Night by Jennifer Brock Novelist/Screenwriter David Fine promised to wear a gown to the Academy Awards in order to get an obnoxious fashion reporter to shut up about the tuxedo his friend fashion designer Claude Marsh had made for him. But since Claude felt insulted too, he assembled a team an worked with the assistance of David's girlfriend bisexual Venezuelan model Maritza Delgado to steer him in a more feminine metrosexual direction. But once the nominations were announced, they raised the bar and got David to agree that it would make an even bigger impact if he looked completely passably female in his gown. David went so far as to have his face surgically feminized and his breasts enhanced with implants. Claude hired Kay Thomas, and expert in teaching men to be women, to show David, now living around the clock as a woman she calls Dee, how to become all that she can be. In Part 13 the bandages came off, and in this installment Dee will venture outside her townhouse for the first time.

Part 14
Dee slept unevenly, having some odd dreams she couldn’t quite remember. And every so often she’d roll over in her sleep and her breasts would complain and wake her up. When she finally decided to get up, it was awkward figuring out how to get out of bed without rolling over. She tied on a robe that seemed to match her nightgown, and put her feet into the pair of two-inch mules that Kay had said were to serve as her slippers.

Remembering to walk as instructed, she sashayed into her bathroom, gathered up her skirts and sat down to relieve herself, even though she wasn’t taped. She performed her usual morning facial treatment, brushed her teeth, and tried to see if a bit of lipstick would make the girl in the mirror look a little less like a zombie. It did, in the sense that a vampire isn’t a zombie. But she didn’t feel like changing to a different color anyway.

She glided down into the kitchen and started the coffee. She wasn’t in the mood for a big breakfast, so she just had a bowl of cereal and some juice. Kay hadn’t gotten up yet, so the morning paper was still waiting on the front steps. If she wanted to read it, she’d have to go out there and get it herself. The thought of going outside as a woman launched a thousand butterflies in her stomach, and nearly sent her orange juice back to her mouth. Why did Kay have to sleep late?

Dee paced back and forth in the front hall, doing her fiercest strut to try to psych herself up. She went to the powder room and emptied her nervous bladder, taking extra care to tuck everything away when she had finished, so there would be no unsightly bulges. Unfortunately, the tape was upstairs, so she had to hope her panties were tight enough to keep things secured.

She tightened her robe so that it would be obvious to anyone who caught a glimpse that this person was definitely female, and couldn’t possibly be the guy who lives there. She strode to the door, took a deep breath, and opened it just a crack. The morning sun was very bright and she had to squint, but she saw the newspaper was in the middle of the front walk, out of reach a good twelve feet away. She would have to leave the house to get it.

However, the bright light gave her an idea. She went upstairs to see what kinds of accessories she had available. On her vanity table, she found the quintessential element of LA fashion for anyone who desired anonymity: a pair of designer sunglasses. They had big smoky lenses that would be just the thing to keep her from being recognized as David.

While she was up there, she taped her tuck, just in case. Another check in the full-length mirror revealed someone who looked less like a zombie and more like a party girl who’d had a rough night the day before. Her hair was still in a tight braid or she would have tried doing something with it to make sure she looked female from a distance.

As confident as she was going to get, she went back downstairs and opened the front door all the way this time, then sashayed down the walk and bent down from the knees as she’d been trained to pick up her newspaper. She carried it in and started reading the front page as she finished her breakfast. Without thinking, she pushed her sunglasses up onto her forehead in a completely feminine manner.

She was sitting there reading the news when Kay finally appeared. Dee told her about fetching the paper and she was impressed with her ability to push past the fears. It was also a good thing, since they’d be going out again. She told Dee to go get dressed in something comfortable but not too casual, and she’d be up in a bit to critique her choices and give her a hand with her hair and makeup.

Dee could hardly believe it, but she tidied up her breakfast dishes and then did a quick sashay up the stairs. This was obviously some kind of test. She choked back her panic and tried to focus on the task at hand.

February in Los Angeles isn’t exactly winter weather, but it isn’t quite spring either. She looked through her closet and found a sweater dress that would probably work nicely. It was a sort of vanilla color, calf length with a loose cowl neck and long sleeves. When she touched it, she discovered the softest thing she’d ever touched. It was probably cashmere, or at least a silk/cashmere blend.

It might be the softest sweater in the world, but it was still a sweater and she didn’t want to be itchy. So that probably meant wearing a slip under it. David’s grandmother always wore a slip under a dress, but Maritza only did some of the time. Dee guessed that this would be one of those times. She found a white lacy slip that seemed to be the right length.

What kind of shoes would go best with this kind of dress? She tried to rack her brain to recall all the fashion shows David had been dragged to. Nothing sprung to mind, so she took a different approach and looked through her shoe collection to see what was available.

There was a pair of boots that spoke to her. The heels were a little on the spiky side, but she was confident in her skills after all the walking lessons. They were almost knee-high, in soft, chocolate-brown leather. The idea of a vanilla dress with chocolate boots just made too much sense not to do it. She laid the dress out on the bed and stuck the boots in the bottom to see if it worked.

It needed something to tie them together. She poked through the closet and found a belt that seemed to be in the same kind of leather as the boots. It had a decent enough weight to it without being too wide. She tested it in her mockup and it did the trick perfectly.

She realized that even though her boots would probably be the only thing showing under the dress, it was probably a good idea to wear hosiery anyway. She selected a pair of suntan pantyhose for convenience.

Now it was time to get dressed. What was she forgetting? She had her nightgown off before she realized she hadn’t picked out any underwear, or lingerie, or whatever a girl is supposed to call her bra and panties.

Fortunately, Vanessa had followed Dr. Ben’s rules of no underwire or push-up bras when she assembled Dee’s wardrobe, so there was nothing in her drawers that she wasn’t allowed to wear. She didn’t think the dress showed much cleavage at all, so she picked a pretty pink lace full coverage bra. To be properly dressed, she looked and found a matching panty.

The panties went on easy, but then she had to slowly replay her lesson in how to put on a bra. The first time it was much too tight, and her boobs complained loudly. With the straps and hooks adjusted properly, it was much more comfortable. She pulled on her padded girdle and tightened her waist cincher, and then slid her hose up her legs.

The straps on the slip adjusted just like on a bra, but when the cups lined up with her breasts it fit like a glove. She pulled the dress over her head and made sure her arms were snug in the sleeves. The realization hit her that she’d forgotten to put on deodorant, so she found her little floral roll-on and snuck it in through her neckline to do each underarm.

She sat on the bed and zipped up her boots, and buckled the belt around where her female waist was pretending to be. She stood up and checked the mirror. It seemed to come together nicely. Other than hair and makeup, what did her outfit need? There was a purse in the closet that matched her boots, so she grabbed that although she didn’t know what to put in it.

The last step she needed to do was pick out what jewelry to wear. She thought maybe a simple gold pendant would go best in the wide neck, and she found a plain gold circle that would work, but she had to switch it to a shorter chain. A pair of wide hoop earrings coordinated with that the best. She didn’t like the look of putting a bracelet on with the long sleeve, so she kept her wrists bare, but she put on a few gold rings to give her hands some sparkle. Her right hand got a twisted knot on her ring finger and a sparkly crystal on a heart-shaped setting on her index finger, and her left hand got a filigree butterfly on the middle finger.

She called to Kay and told her she was ready to be judged. Kay looked her over and said that she did an admirable job. Dee was one of the easiest students she’d ever had; she already had many very well-honed female instincts, and so far no male attitudes that needed to be exorcised. The only change she made to Dee’s look was to add a watch bracelet. They had an appointment where it would be important to be on time.

Before doing Dee’s makeup, Kay had her go wash her face and make sure the wrong-colored lipstick was all off. She had her sit at her vanity table and showed her how to drape a towel over her shoulders to keep any powders that might fall from messing up her dress. Kay took a pair of tweezers and radically plucked Dee’s eyebrows into a beautiful, feminine arch, and then used a pencil and a comb to give them more definition. In their delicate new shape and without the projecting bone behind them, there was nothing even remotely masculine remaining.

Even though they were slightly behind schedule, Kay made Dee do her own makeup, talking her through every step. She started with a little bit of concealer under her eyes, and then a light coat of foundation all over, followed by a translucent powder to even the texture. Kay remarked that she wouldn’t need any of the “special tricks” she usually had to teach her clients; Dee could have the same makeup routine as any genetic female. They were doing a little more than the average woman used in the daytime, but only because of the nature of their appointment, which she wouldn’t expand upon.

Applying eyeliner was scary. She had to almost poke herself in the eye with a sharp little pencil. The magnifying mirror made it a little easier, but her hand was still nervous and shaky. The first line she did came out a little uneven, and Kay made her wipe it off and try again. The eye makeup wipe removed some of her earlier work and she had to reapply concealer, foundation, and powder to the area. She asked Kay if she could wait until she got the eyeliner right to fix the other stuff, but she said it would encourage her to try harder.

It took two more attempts to get the left eye done, but the right eye was good enough on the first attempt. The only tricky part about mascara was getting the wand at the right angle. She made a few marks on her eyelid, but fortunately they hadn’t done eye shadow yet, so removing them didn’t mess up anything else.

That was next. Kay had pulled a palette of browns and beiges for her eyes from Dee’s outfit. There was a real art to blending the shades, so Kay did one eye for her and had her copy it on the other side, one step at a time. When they were finished, her eyes didn’t look familiar at all.

The trick to applying blush was finding the right spot on her face. Kay told her it was something that takes even natural women a while to learn, if like Dee they don’t have strongly defined cheekbones. She had to make an exaggerated smile to help in locating the “apples” of her cheeks, and then give them a quick stroke with the brush.

Finally, she needed to put on some lipstick. Kay corrected her color choice from earlier by going with a darker tone. Dee thought she knew how to apply it: just purse your lips and draw on the red part, then smack them together. But Kay showed her how to do it using a little paintbrush instead of directly from the tube, to have more control over the shape. She did get to kiss a tissue like they always show women doing when they put on lipstick in movies.

With her makeup done, they had to think about what to do with her hair. Kay took off the elastic and helped Dee take it out of the braid. It came out slightly damp and with a little more wave to it. Dee wanted to just wear her hair down, but Kay said she needed to keep her hair off of her face and couldn’t hide. She found a nice leather hair slide and pulled her hair back and off of her face while still letting it hang loose in the back. She teased her bangs a little and said that would have to do.

Kay showed Dee that they’d already everything that David had had in his wallet into a ladies’ clutch that she could put into the handbag she’d picked out. Then she told her what else to put in there, like enough of the cosmetics they’d just used so that she could refresh her look, and a brush and comb and a spare hair clip to fix her hair, and some tissues, and her keys, and a bottle of clear nail polish in case she got a run in her hose, and her sunglasses, and her pain pills, and a bottle of hand sanitizer, and a tampon just in case.

“Just in case what?”

“In case you’re in the ladies’ room and someone asks if you’ve got one.”

“The ladies’ room? Isn’t that illegal? I don’t think I’ll be in there.”

“Relax, D. You’ll do fine. With your pretty face and nice figure, no one will think you don’t belong in there.”

“But my voice is too deep.”

“We’ll start your voice lessons this afternoon. In the mean time, just don’t try to say too much. Try softening your voice to just above a whisper, and no one will think you’re strange. Think of Bea Arthur. Genetic women don’t all have high-pitched voices.”

“If you say so.”

“Don’t worry. I’ll be with you the whole time, and I’ll do most of the talking for us.”

Dee was still very nervous, so Kay had her use the bathroom before they left, to make needing a trip to the ladies’ less likely. David’s car was in the garage, so she didn’t have to feel self-conscious about walking outside again. Kay showed Dee the way a woman gets in and out of a car in a dress, and had her practice a few times. She didn’t want to throw too many things at her at once, so Kay drove.

Their first stop was at a branch of David’s bank. Kay told Dee to walk in and use the ATM, and withdraw a couple hundred dollars. She would have left her purse in the car if Kay hadn’t reminded her. She showed her where in the little clutch wallet inside in the big bag her ATM card was, and where the bills would go. She took a moment to close her eyes and center herself, checked her reflection in the vanity mirror, and then got out of the car, swinging her legs around just as she was taught.

She slung her bag over her shoulder and sashayed into the bank. An older man in a business suit coming out held the door for her, and she smiled and murmured a thanks. He turned his head to watch as she passed, but she didn’t notice. The ATM was already in use by a little old lady, and there was a young guy in jeans and t-shirt waiting behind her. She got in line and waited.

Kay had never explicitly taught her how women stand, so she had to figure it out based on her lessons in walking and getting in and out of chairs. Her main problem was that all her posture training said she needed to stand up straight and hold her head high, but she really wanted to look down at the floor and avoid eye contact. She wasn’t sure what a real woman would do when forced to stand and wait, so she tried to think of ways to seem busy.

She pulled out her compact and checked her makeup, dabbing a little powder here and there. She really wished Kay hadn’t taken away her phone, or she could pretend to call someone. She tried looking across the bank to where the tellers were, to see if there was something to seem interested in. She finally settled on grabbing a pamphlet about mortgage rates from a display not too far away, and attempted to seem fascinated by it.

After a while, she got that creepy feeling that she was being watched, and looked up to see the guy in front of her was staring at her. Oh crap, he knew! She needed to get a grip on herself before she had a panic attack. She closed her eyes and took a deep breath. Ok, so this guy had figured out that she was a crossdresser; what had he seen, and could she keep him from telling anyone else?

She opened her eyes, and the guy wasn’t staring anymore. He was actually looking away and seemed kind of embarrassed. Something in his expression and body language seemed familiar, and then the realization hit her — she hadn’t been read; he’d been caught checking her out! It was the complete opposite of what she’d feared. This guy had been imagining her naked, and she was sure that his mind’s eye saw a vagina between her legs and nothing more. She smiled to herself and shot him a wink and pointed at the ATM. He’d been so enthralled with her that he hadn’t noticed it was free.

He chivalrously said that she could go ahead of him. She smiled, thanked him, and did her sexiest walk up to the machine. It was hard to concentrate on her banking knowing full well that he was probably looking at her ass the whole time, but she managed to pull it off without a hitch. She pulled out her clutch bag and removed her ATM card like she’d done it a thousand times. There was a slight bit of awkwardness when she realized that with her longer fingernails she had to hold her fingers parallel to the keypad instead of perpendicular, but she didn’t mess up her password or anything. She put her money and receipt and her card back in her bag, turned and walked out.

Feeling mischievous, she looked back over her shoulder and waved to the guy who’d been watching her wiggle. He turned beet red and she let out a little laugh. She opened the door and backed into the car like she was supposed to, and then let out a great exhale of relief and allowed herself to shake from all the accumulated nervous energy.

She told Kay how it went, and she said that Dee had done an excellent job, and that she really had nothing to worry about. Dr. Ben had done great work. As long as she kept her clothes on, no one would ever suspect that her panties packed a surprise. The only “tells” that remained were a few subtleties in the way she moved, that they’d be working on, and her voice if she were to speak up, but intensive training for that would be starting as soon as they’d finished their errands for the day.

She did give Dee a warning that she needed to be careful about flirting with or teasing strange men, like she had in the bank. Some guys mistake a smile for a proposition, and might try to pursue her. But as long as she kept her contact brief, and in public places, in the light of day, she should be safe. Since she lacked a genetic woman’s lifetime of experience that helps her tell the creeps from the decent guys, she’d be extra vulnerable to predators. Kay tried not to be too scary, but the “all men are potential rapists” school of thought has saved more women than “innocent until proven guilty.”

They drove off in silence, as she’d given Dee a lot to think about. She was still in something of a state when they reached their second stop, a cute little bakery in the middle of nowhere. This time Kay got out of the car with her, and they both went into the shop.

The woman behind the counter was about as tall as Kay, but stockier, and probably a little older. There was a hint of olive in her complexion, and maybe a touch of gray in her long black hair, which was pulled back in a bun under a hairnet. She wore a long white chef’s apron over a blue dress.

Kay greeted her like an old friend. “D., this is Jackie, baker of the best cupcakes in the county.”

Dee waved and mumbled, “Hi.”

“Jackie, this is D., my latest disciple.”

Jackie looked her up and down with wide eyes. “Oh, really? I never would have guessed.”

She knew the kind of work Kay did; she knew what Dee was! Dee wanted to run away and hide somewhere.

“Don’t worry, Honey. I’m not the enemy. I’m a graduate of Miss Kay’s tutelage myself.”

Now it was Dee’s turn to be surprised. Jackie was a man pretending to be a woman, too, or a woman who used to be a man, or whatever the right distinction is? David had never met a trans-anything before, as far as he knew, and now he not only was one but there was another only a few feet away.

Jackie could tell. She’d seen that look before. “Am I the first of the sisterhood to meet you since your coming out?” She took off her disposable gloves and came around to the front to give Dee a big bear hug. “Welcome to the club, Sis! You listen to Kay; she knows what she’s talking about.” She gave Kay an embrace, as well. “It’s nice to see you again, too. So are you just taking her out into the world, or are you here on business?”

Kay sighed. “Business, unfortunately. She’s got an appointment with Loretta at 11:00. We’ll need the usual dozen red velvet cupcakes with cream cheese icing.”

Jackie went back behind the counter and filled a pink box with their order. When Dee paid for the cupcakes, she handed her a business card. “Feel free to call me if you’re having any trouble adjusting and need someone to talk to. I wrote my cell on the back. But a pretty girl like you ought to have no trouble passing. I only wish I looked half as good as you.” Dee thanked her, blushed, and put the card in her purse with the change.

Kay only gave a partial explanation of what was going on as they drove to their next destination. Dee needed a photo id that matched her look better than David’s driver license, just in case. She didn’t plan on taking Dee anywhere that would need her to show ID to get in, or shop at any pretentious stores that would claim to need ID before accepting a credit card, but for legal protection it was a good idea to officially update the photo on file. Sometimes cops can be jerks, and if somehow one asked her for ID and she didn’t look anything like the picture, he could take her in for committing fraud by pretending to be someone she wasn’t.

So they were going to get her an ID, and Loretta was someone Kay knew at the DMV. She was going to do them a favor, and in exchange they were going to “accidentally” leave behind their box of cupcakes when they left the office. They wouldn’t be doing anything illegal, so she didn’t need to worry. Technically they were probably bribing a government agent, but no one worries about those kinds of technicalities.

It turns out the DMV office they needed to get to was in Glendale, so it was a bit of a drive. Dee tried to get some more information about what to do or say, but Kay told her to just relax. They were doing this before any vocal training because Dee would have to speak in her natural voice as part of proving her identity to Loretta, but that wouldn’t happen out in the open in public.

When they got there, they didn’t have to stand in the usual DMV line from Hell, since they had an appointment. Loretta was a sassy little black lady who had a giant smile when she saw Kay. Kay had already filled out the forms ahead of time, and showed her David’s original ID, and a letter from the doctor, and gave her word, which was good enough for Loretta. All she asked Dee was whether this information was correct, and Dee tried to sound as “David” as possible when she said yes. It must have been good enough, because it made Loretta look twice.

She walked Dee over to a workstation where she stood in front of a curtain while Loretta worked a camera. Dee made a little smile and tried not to blink, and thought she took a pretty good picture, but Loretta took an extra one, “just in case something went wrong.”

It turns out something did go wrong. The first time she printed the data for the card, the computer was acting funny and only printed the first initial in the box for the first name, and it left the box for gender completely blank. Loretta didn’t catch the mistake until after the card went through the laminator. She thought they might get a kick out of it and showed them the bad card at the same time she was giving them the good one that said “David” and “M” like it was supposed to. She’d be taking the bad card to the shredder later.

Loretta piled the Identification forms Kay had given her on the table, and she suddenly noticed the time and gathered them up quickly and told Dee they had to hurry back to the city or they’d be late for their next appointment. Dee thanked Loretta and followed Kay quickly out to the car.

Once they were on the road, Kay handed Dee the paperwork and told her to sort it. Son of a gun, that bad ID card had gotten mixed in with the others! She must have swept it off the table with the other stuff. And wouldn’t you know it, but she couldn’t remember what happened to the box of cupcakes. She recalled that she didn’t want to leave them in the car where the frosting would have melted, but she couldn’t picture where she left it.

With the official story out of the way, Kay told Dee to use the “D” card for things like getting into clubs or using a credit card, but to always use the “David” card if a cop ever wanted identification. The other one wasn’t exactly legal, but it wasn’t exactly illegal either — nothing on it was false; it was just incomplete. But cops don’t like gray areas.

She drove them out to an old vacant shopping center. It had a nice big parking lot, and that was where Dee was going to learn to drive in heels. It shouldn’t be too bad since her car was an automatic, but it would feel very different from how she was used to driving. Kay told her that some women keep an extra pair of flats in the car and change their shoes for driving, and then swap back when they get where they’re going, but she didn’t believe in giving her students that kind of a crutch.

Between her higher heels and her posture lessons, Dee was sitting in a very different position than usual, and she had to adjust everything: the mirrors, the distance from the seat to the dash, and the angle of the seat back. She put on her sunglasses and started the engine. It was all about learning how to put the right amount of pressure on the pedals with her spiky boots on. At first she was very jerky, erring on the side of braking too quickly, but after a while she was comfortable doing laps in the parking lot and Kay told her to try to drive home.

She was nervous and a little too cautious on the city roads, and had some trouble getting onto the highway until a nice guy let her merge. She gave him a little wave, and asked Kay if that was appropriate. She said that was fine, and she could even go so far as to blow a guy a kiss for being nice on the highway, since there were so many road ragers out there spreading a little more love couldn’t be a bad thing.

Back at home, Kay had her go up and change out of her waist cincher and girdle and come back down. She’d need to be able to breathe freely. Kay had set up a special DVD in the living room that would teach her how to change her voice to something more feminine. The presenter was a trained speech therapist who was also a transsexual, so she really knew what she was talking about.

It wasn’t going to happen quickly, either. The lessons were a series of steps, and only after completing them all would she end up sounding like a natural female. Because it wasn’t healthy to put too much stress on the vocal chords, she could only do one step a day.

It started simply enough by learning about how the voice works, how the various features of a voice are generated by the breath, and voice box and in the mouth. And the instructor talked about the differences between male and female voices. She then went on to the first practical lesson, which was about breath control. Dee followed along, and thought she was doing a decent job.

It was kind of weird sitting and talking to a television with Kay sitting there watching her. She didn’t say anything until the lesson was over, when she pointed out some ways Dee could improve her technique, and they made sense. After dinner she did the lesson again and Kay said she was definitely on the right track.

Her day had been so nerve-wracking, she ended it with another relaxing bath, only this time she opted for a book instead of a fashion magazine. Kay gave her a choice, and she went with the classic Pride and Prejudice.