Oscar Night by Jennifer Brock What started out with a flippant comment to an obnoxious fashion reporter has snowballed into an exploration of gender identity. Novelist/Screenwriter David Fine made a deal to wear a gown to the Academy Awards presentation, and took it much further by getting his face surgically feminized and his breasts enhanced. His best friend fashion designer Claude Marsh hired "Feminine Deportment Coach" Kay Thomas to train him how to act. Among her draconian rules were that his girlfriend Venezuelan model Maritza Delgado should stay out of contact for a month as he works to develop a new female identity, which she addresses by her initial D., or "Dee." So far, Dee has had a lesson in how to walk in heels, and had a house call from her nurse. In this installment, she gets a few more lessons and begins to worry about who she or he truly is.

Part 13
Dee’s outfit for her second day of walking lessons was almost the exact opposite as the previous one. Her top had long flowing sleeves, but her skirt was short and tight and almost made her look like a cheap whore (and judging by the bandages on her face, a whore who had disobeyed her pimp). Her shoes were at least an inch taller than the day before, and Kay made her wear pantyhose, which required learning how to put them on without stretching them unevenly or putting a nail through them. She ruined three pairs of hose before getting it right.

Sitting in a chair in a miniskirt also introduced a whole lot of new rules, all about being aware of the line-of-sight to your panties. Dee also had to act as though people would be noticing her legs, especially male people, and display them appropriately. Kay taught her three different ways to cross her legs, depending on how sexy she was trying to be.

Kay showed her a video of some fashion show footage, to watch how the models walked. She then took her camera sand recorded Dee walking down the hallway, both toward and away from the camera. She then played both videos for her, and pointed out what the models were doing that Dee wasn’t, and vice versa. The short skirt made sense in that she could see exactly what her legs were doing.

They worked all day on walking, taking breaks only for meals and when Evelyn came by. She raised an eyebrow at Dee’s micro-mini, so she explained about needing to see her legs for walking practice. Her checkup was pretty much a repeat of the first one: cleansing, changing bandages, and massaging and treating her breasts with lotion. It was almost a sensual experience, which made Dee grateful that Kay’s special tea was keeping her from having an embarrassing reaction.

There was more walking and standing and sitting in the evening, until Dee was too tired to do more. She took her drugs and went to bed, and this time was able to get into her nightgown unassisted.

The next day, Kay made her wear a padded panty girdle again, like she had on that first day before her surgeries. She got to wear stockings instead of pantyhose, but she had to roll them up her legs and attach the garters herself, which was tricky with her long nails. She thought she did okay until Kay showed her the runs she’d caused and made her take them off and try again. Once she got it right, she had to also take her stockings off without damaging them. Then Kay raised the stakes by handing her a fancy sheer black pair and told her that this time she had to get them on while keeping the seams straight.

Kay also laced her into a tight waist cincher again. It was good for helping her stand up straight, but breathing wasn’t as easy. She pulled a lacy black camisole over Dee’s head and had to unhook the straps so she could put it on without raising her arms, and then hook them back when it was in place. A gauzy blouse with fluttery cap sleeves went over that, and then she stepped into a red skirt that was slightly longer than the previous day’s micro-mini, and zipped it up in back.

A pair of red patent leather pumps with four-inch heels completed her ensemble, and she stood up and looked in the mirror. The smaller waist and rounder hips really made her breasts look bigger. It was a deliberately sexy outfit, but she didn’t think she looked as much like a common hooker as the day before, maybe more of a high-class call girl. She supposed it was possible she could be just dressed to impress for a hot date or a night of clubbing, but she still felt more like a sex worker.

She had to repeat everything she’d learned about walking, and her accentuated figure really helped her match the models in the video. It was kind of weird spending the day watching behinds in tight skirts wiggling back and forth without feeling anything remotely sexual about it, but she guessed that meant Kay’s tea was working. Dee wondered if watching the tape of her own sexy posterior walking down the hall would have turned her on if not for the tea.

By dinner time, she had mastered the walk that Kay called a “runway sashay,” a slow sensual stride that needed a lot of roll in the hips. Dee was glad that all her walking lessons were over, until Kay told her there were two more walks she needed to be able to do, a fast, confident “catwalk strut” and a graceful, ethereal “ballroom glide.” It took four more days of training to add those walks to her repertoire.

All the exercise really made her sweaty and uncomfortable, but at least Evelyn was coming every day to give her a sponge bath, and on her fourth visit she even washed Dee’s hair for her. She had to lean over the edge of the bathtub, so it wasn’t quite as nice as getting a shampoo in a salon, but it was good to feel clean.

Once she had all three walks down, Kay made sure she never relaxed and reverted to a slouchy male style for getting around the house. Dee had to keep at it until a feminine stride became second nature and she wouldn’t even have to think about it. But with the formal walking lessons officially over, she thought they could take a break and switch back to another installment of “Establishing a Feminine Cultural Frame of Reference.”

Kay called Vanessa and invited her over for a day of Chick Flicks. They watched Terms of Endearment, and Dee really didn’t need to be told that she had permission to weep at the sad parts. After the movie they had a light lunch and talked about what they’d liked in the film, and the real lesson began in earnest. She wasn’t being too aggressively conversational like a alpha male would, but Kay did have some suggestions for alternate phrasing that would express her opinions in a more feminine manner. Dee also needed a little bit of coaching to talk more about feelings than things.

But by far the toughest part of the lesson was tying to use more gesture when talking, and to express herself as a female through body language. Dee had to struggle to think about every little movement, and she messed up a few times by over-exaggerating. Kay told her not to worry; it would take a lot of practice before it would feel natural or automatic.

Their second feature was Thelma and Louise. This time Kay paused it a few times, to call Dee’s attention to how an actress was moving while speaking, and had her try to mimic a pose or movement. The post-movie discussion spent a little too much time on the subject of Brad Pitt’s butt for her taste; she appreciated him aesthetically, but couldn’t really think of him as a sexual object the way the others could, especially with her libido turned down by Kay’s herbs. But the idea of him didn’t repulse her either, which seemed kind of weird. She felt she did a good job keeping up her end of the rest of the conversation, participating without trying to dominate.

The afternoon brought a surprise when Evelyn did not come alone, but brought her husband with her. After removing her dressings, Dr. Ben examined each of her surgical sites, and decided that her stitches were ready to come out. It didn’t really hurt, but having the bits of suture pulled through her skin was a weird feeling. The best part was the tremendous relief of finally getting the packing out of her nose.

Dee was eager to look in a mirror, to see what her new face looked like without all that tape and gauze, but they weren’t finished. They removed her blouse, and for the first time ever her surgical bra came off. Dee couldn’t help but look down at the very real pair of breasts sticking off her chest. There were a couple of stitches in each of her underarms that came off and then they were done.

She stood and went to the mirror, and it was amazing! The face looked familiar, but it was softened, more feminine, maybe even cute. And the boobs almost looked natural. They were big, but didn’t really seem too big for her body. Her areolas had stretched a bit, but her nipples were still on the small side. David looked at the girl in the mirror and wondered if he was still in there somewhere. The image really didn’t feel like the same person anymore.

Dee wasn’t sure how long she stood there dumbfounded at her own appearance. She only snapped out of it when Vanessa made a comment, “Damn, Girl! You’re really built!” Dee got really embarrassed that everyone was there now, and reflexively covered her naked breasts with her hands. Her huge boobs made her hands seem smaller and daintier.

She blushed even redder when Vanessa made her move her hands so she could measure Dee’s new bustline. It suddenly made sense why they’d called her in, since Claude had put her in charge of Dee’s wardrobe. Vanessa confirmed that she was a 38D, as planned. Ben said she could switch to regular bras in the daytime, but he wanted her to keep wearing the surgical bra at night. And he told Vanessa that push-ups and underwires were still off limits — soft cup only.

Vanessa went to rummage through the closet while Evelyn showed Dee how to rub the special cream into her breasts to promote elasticity in her skin and reduce the chance of getting stretch marks. Then she had to massage each one and give her implants a good squeeze to make sure everything was staying appropriately supple. Dee tried to pretend that it wasn’t terribly embarrassing by casually asking Ben and Evelyn if they had somewhere to be, or if they could stay for dinner. Her meatloaf was already in the oven and Vanessa had agreed to join them, so there would be plenty for more. Evelyn surprised her by accepting the invitation.

Ben had a new pill bottle for her. He’d reduced her pain medication and wanted her to switch right away, even though there was still some left in the old bottle. She was to start taking the lower dosage, but keep the stronger ones handy in case she had any strong pains, and to call him immediately if that happened.

Finally Vanessa returned from what seemed like an eternity going through her wardrobe. Dee was grateful to be less exposed. Vanessa brought her a black, silky bra and Kay talked her through the steps in putting it on. She had to slip her arms through the straps, and then bring the cups up to her breasts. Next, Lay told her to slide her hands along the band to the back, so that it didn’t move out of place, and then find the hooks on one side and the loops on the other and bring them together. She got one hook in, but there were three of them and on the first try she ended up getting the next hook into a different set of loops. Then she had the top and bottom hook okay, but the middle one was out and it was impossible to hook with the other two in place.

She had a tremendous sense of accomplishment at getting them all hooked, but Vanessa and Kay agreed that her band wasn’t tight enough and she needed to change it to the next set of loops. Once she finally got that done, she had to go back to the front and make sure she was sitting correctly in the cups. She had no idea what that felt like, and needed to be shown what a right and wrong fit looked and felt like. With the cups in the right place, she had to adjust the little buckles on the straps so they were tight enough but not too tight.

When it was all done, she looked in the mirror and it was worse than when she was topless. The sexy black bra had lace along the edges, and the cups only seemed to cover about two-thirds of her breasts, leaving the tops and inside edges exposed and decorated with lace. She was showing a cleavage, and it made her chest look bigger and more prominent than when her boobs were naked.

Beyond just wearing new underthings, they thought that Dee should change her outfit, too. Kay ushered Ben and Evelyn out of the room, but Dee wanted to make sure they were treated properly, with a drink or something. Kay said it was a good sign that she wanted to be a good hostess, and told her not to worry. She’d take care of them and then come back.

Vanessa had picked a silk wrap dress in a sort of rust brown color. It had three-quarter length sleeves and a really deep v-neck. It was almost too revealing. Dee thought that it would hang better if she used all her figure enhancements, so she took the dress off and then put on her padded panty girdle and waist cincher before putting the dress back on. At Vanessa’s suggestion, she also switched to suntan pantyhose. The shoes she’d selected were three-inch peeptoe pumps in copper-colored alligator texture.

The shoes made more sense when she added dangly earrings with copper bangles and little wooden beads, and a coordinating necklace that nestled a copper pendant right between her breasts. Vanessa put a bunch of thin copper bracelets on her left wrist and a large ring with a yellow stone on her right middle finger, and then let her look in the mirror. The color scheme really brought out the red accents in her hair.

Kay came up and did her makeup. Ordinarily, she would have stood by and instructed her student what to do and made her apply everything herself. But since they were pressed for time and Dee’s face was still a little tender, she cut her a break and did it all for her. She stuck mainly with the palette of earth tones that Vanessa had set, and went for a mostly natural look, with cocoa eye shadow, bronze blusher, and a maroon lipstick. She did inject a little drama in the look with black eye liner and mascara, and frightened Dee with an eyelash curler. She teased her hair up a little and gave it a shot of hairspray, and gave her a look in the mirror. Kay had dusted a little glittery powder in her décolletage, that twinkled when the light hit it a certain way. That drew her eye before she got a good look at her face.

David had never really learned to appreciate what makeup could do for the average woman. He’d always just shrugged it off as a societal convention with no real value. Living with Maritza who’d go from simply stunning to absolutely gorgeous when made up didn’t do much to help dispel that illusion. But when Dee looked at her reflection and saw what the right cosmetics could do to her plain yet feminine face, she was amazed. When they’d made up David to look like a woman that had been like a mask or disguise, but this was something different, more like an enhancement. The woman in the mirror was flawlessly beautiful! There was no possible way this person could ever have been male. Somewhere deep inside, David’s sense of identity was crumbling.

Dee was worried about messing up her pretty outfit when she finished getting dinner ready, but Vanessa was prepared. She tied a white ruffled apron onto her, and told her she could put her ring and bracelets in the pocket while she was cooking. They went downstairs and she told Vanessa and Kay to keep Ben and Evelyn entertained, refusing all offers to help with the meal, although she did let them serve the wine.

Most of the meal was nearly ready. The meatloaf was ready to come out of the oven to rest. The potatoes had been mashed and seasoned, and went in just long enough for the cheese to melt. The dinner rolls would be done at roughly the same time. She threw together a tossed salad fairly quickly. She was using cherry tomatoes, so all she had to do was tear up some romaine and slice a Bermuda onion. She’d made croutons the day before and had plenty left. She popped some mixed vegetables into the microwave while she stirred a roux into the drippings from the loaf for gravy.

She set the table and lit some candles for a centerpiece, put her ring and bracelets back on, hung her apron up in the pantry, and then called everyone in. They all complimented her on a lovely presentation, and Ben said the chef was even lovelier and proposed a toast to “Delicious food and beautiful company.” Dee blushed and said that she was merely the culmination of the efforts of the rest of them, but she hoped the meal would satisfy.

It did. As they ate, Evelyn turned back into a fan since she was off duty. She peppered Dee with questions about the latest novel. She had some difficulty thinking of herself as David the author, but did her best to come up with answers. It left her feeling strange and disoriented. She shook it off and focused on trying to eat in a feminine manner like Kay had taught her.

The dessert which had been chilling in the fridge featured a blueberry compote filling sandwiched between layers of sponge cake and topped with freshly whipped cream. She served it with a pot of strong, slightly bitter coffee. The flavors worked well together. Even though most of her guests were stuffed, it was too good a treat to pass up. They talked for a bit, but it wasn’t long before it was just Kay and Dee left.

Kay said she’d done well enough at hosting an impromptu dinner party that they’d be skipping some lessons. Most of her students would have taken a more masculine, aggressive approach, but Dee had seemed to know instinctively how to be a good hostess, allowing herself to slip into the background and let her culinary creations take center stage and show off for her. She hadn’t even tried to steer any of the conversations.

Dee took off her jewelry and swapped her dangly earrings for sleepers. Her feet felt relieved when she slipped off her shoes; there was a downside to reducing her pain medication. She hung her dress up and Kay had her sit at her vanity in her underwear to remove her makeup with cold cream wipes. She remarked that it would be nice to be able to shower again and that gave Kay an idea. She ran off to the bathroom, and Dee could hear the water running.

She’d decided that Dee’s reward for the day would be one of the ultimate female indulgences — a luxuriating bubble bath. She told Dee to strip and put on her robe. When she called her into the bathroom, the tub was filled with warm, floral-scented water covered in rich foam. Soft music was playing on a portable CD. She shed her robe and stepped into the tub, then slid down beneath the foam. It was a strange sensation as her breasts tried to float. Kay handed her a glass of sweet wine and a fashion magazine and told her to just relax and enjoy a well-earned soak.

Dee laid back and closed her eyes and listened to the music for a while. She felt very feminine, and ran her hands along her smooth legs and across her sexy flotation devices. After a few sips of wine the pleasant scent rising from the bath was making her very calm and serene. She picked up the magazine and read a few articles, trying to imagine herself in various styles. There was an article about getting your body ready for bikini season that was a little depressing, since her thick waist and flat behind would never look good in a two-piece.

She flipped ahead quickly and stopped short when she came to an ad that had a photo of Amanda. It brought to mind a few naughty memories, but mostly reminded David that he missed his girlfriend. The illusion faded for a bit, and he sat up in the tub and hugged his hairless legs to his breasts and let himself sob for a couple minutes before trying to get back in character. Dee ducked her head under water so Kay wouldn’t be able to tell she’d been crying, and then called out that she was done with her bath. She shouted back that she was to pull the plug then take a quick shower to rinse off the bubbles and to wash and condition her hair.

When she came out of the shower, Kay gave her a big fluffy bath sheet to dry off with and then tuck around herself, and a second towel for her hair, showing her how to turban it. She got out a bottle of after-bath moisturizer and was going to explain to Dee how to use it, but she already knew how. Maritza had made skin care part of David’s regular routine months before.

She put on a clean surgical bra and a fresh pair of white cotton panties, (Kay told her not to tuck anything inside her body, just push them all back and out of the way) and then she pulled a new sleeveless white cotton nightgown over her head. She had to comb out her hair while it was damp, and then Kay braided it for her so she wouldn’t get tangles while she slept.

She got into bed and wished Kay a good night. It had been a long and eventful day, which gave her a lot to think about. She hoped to have happy dreams. Oddly enough, her last thought before drifting off to sleep was the image of Brad Pitt’s butt.