Oscar Night by Jennifer Brock When novelist-turned-screenwriter David Fine was first nominated for an Academy Award, he wore a red tuxedo provided by his best friend, fashion designer Claude Marsh. An obnoxious TV presenter told him that if he wanted color he should be in a gown, and he agreed. He's been nominated again, and Claude assembled a whole cabal of people to help David make the ultimate impression in his gown. David's girlfriend, bisexual model Maritza Delgado, was on board with the idea of making him as feminine as possible. To that end, he's had major facial surgery and been implanted with a spectacular pair of breasts. David, or Dee as she's been calling her female self, has been working with his live-in feminine deportment coach Kay Thomas hired by Claude for a couple weeks now, and has been making good progress. In this chapter, our girl Dee practices flirting, and has an interesting naked experience. (Note: to the couple of readers I'd told what was going to happen in this chapter, my muse had different ideas, so I had to postpone that until the next one.)

Part 16
One morning, Kay told Dee to put together an outfit that best represented the “Beverly Hills housewife” look. She thought about it and decided that the key was in the accessories. She found a pair of sunglasses with large, round smoky lenses that went from dark at the top to lighter at the bottom, and thick, white plastic frames with gold accents on the sides. That seemed to fit the uniform for most upper middle class women in Southern California.

To pass as a housewife, she’d need to look married. That would mean wearing a ring on her left hand. She rummaged through her jewelry box for a ring that would fit on the right finger and appear to be a wedding ring or engagement ring, or both. She found a ring with a large oval blue stone in a setting surrounded by little sparkly white ones that seemed like it could do the job. Dee wasn’t sure if it was an actual sapphire and diamonds, or if it was costume; either way would have made sense for Claude to have done when putting together her wardrobe.

There were some earrings in the same style as that ring that would coordinate well with it, but she didn’t think a real housewife would always try to match her wedding/engagement ring. She found a fun pair of retro-looking earrings with dangling squares, circles and triangles in black and white plastic that kind of went with her sunglasses, and a chunky bracelet that kind of went with them.

She decided that she was the kind of housewife that dresses to be noticed, so she selected a bright red dress. It was relatively lightweight cotton, so she wore a full slip beneath it. It was sleeveless, with a low scoop in the front that would have been too embarrassing for her to wear at the beginning of her womanhood, but made her feel sexy at this point. She helped accentuate her cinched-in waist by putting a thick, shiny black belt on top of her dress, and the full skirt made the most of her padded hips.

Dee repainted her finger and toe nails in an attention-seeking fire engine red. Since she had her girdle on, she used its garters and went with stockings instead of pantyhose, in a fairly neutral suntan color. A pair of kitten-heeled black peek-a-boo pumps went on her feet and she picked out a black purse with a nice long shoulder strap.

She styled her hair simply, using a silky white hairband just to get it off her face. With her makeup, she went for a little more of a night look than she would have otherwise, starting with a base of concealer, foundation and powder. She fully lined her eyes in black eyeliner with a thin, crisp line. A liberal coating of black mascara went on her eyelashes and two shades of pink eye shadow were blended on her lids. A hint of blush on her cheeks, and then she finished it off with a bright red longwearing lipstick with a glossy topcoat.

She applied a few spritzes of Notorious in strategic locations and did a twirl before the mirror. Satisfied that she was the right degree of hotness she’d been aiming for, she sashayed down to the living room. Kay was impressed, and said she’d captured that competitive upper middle-class look splendidly. Her only suggestion was that Dee might want to throw a black silk shawl over her shoulders in case there was a nip in the air, but otherwise she could very easily pass amongst the natives as though she were one of them.

Kay said that they’d be going grocery shopping and told Dee to write out a list of what she needed. Normally David just worked from a mental shopping list, but Dee figured that it was just another exercise in feminine penmanship. She checked her pantry for what staples were running low, and planned out what she wanted to cook for the following week and noted which ingredients would be needed.

They got in the car and Kay had Dee drive. She had her choice of going to David’s usual grocery store where things would be familiar, or a new place where she wouldn’t have to be nervous about being recognized or of acting like people should know her. Dee chose the new place, so Kay had her drive out to an upscale market in Sherman Oaks.

The shocker came when Kay asked to be let out at a Starbucks down the street from the grocery, and said that this was to be Dee’s first solo outing. Kay thought that environment should be a comfortable one for her, since she was such a culinary virtuoso. She was to go into the store and not come out until she’d bought everything on her list, but if something went wrong she could call Kay and she could come to save her.

Dee had to take a few deep breaths in the car before she felt comfortable enough to drive on to the market. Her heart was racing and she glanced down and saw that she had the clichéd “heaving bosom,” and that made her chuckle a little. Her two friends down there really were unmistakably female; there was very little chance anyone would be suspecting her secret identity. Calming, she flipped down the sun visor and checked her makeup in the vanity mirror. She smiled and blew a kiss to her smoking hot reflection, then closed the mirror and put the car into drive and pulled out of the parking lot.

At first Dee was a little worried she was overdressed, but then she saw some of the other ladies getting out of their luxury SUV’s, and they had hair that looked fresh from the beauty parlor, and outfits that seemed couture if not at least designer label. And they radiated sex just as much if not more than her. Some of them also had their implants proudly on display, others were showing a lot of leg, and some unwisely chose to show midriff in fashions that would have been more appropriate for girls twenty years younger.

Dee opted to leave her shawl in the car. She felt that it detracted from her look. However, she regretted that decision as soon as she closed the car door. There was indeed a slight chill in the air and she could feel her nipples becoming erect almost immediately. She was sure that they’d be visible through her clothes, an irrational fear for certain since she was wearing a bra with light padding and a full slip under her dress, plus her nipples weren’t as large as a natural woman’s to begin with. But nonetheless, she was sure that everyone in the parking lot could tell she “had her high beams on.”

She wanted to run into the store as fast as possible, but she knew that wouldn’t be appropriate for her female persona. She carefully got her reusable canvas grocery bags from the trunk, and then did a brisk but still sexy sashay over to the market. One of the workers, a teenage boy was just returning a load of carts when she got inside, and he pulled one out of the row for her and even wiped down the handle with his cleaning cloth. She smiled and thanked him, and it took him a few seconds to blink and remember to breathe. Dee was beginning to enjoy all the attention her new shape attracted.

She did feel comfortable and confident in the grocery. Kay was right; it was her element. She knew a use for almost every ingredient in the place, and that made her feel more successful as a woman, ready to feed and nurture her family. She knew what she was talking about when she asked the butcher to cut her some thicker pork chops, (he was a sweet older man who actually flirted back) and she even showed one of the other women shopping in the produce section how to tell if an artichoke is fresh.

Remembering that her doctor had said she wasn’t supposed to raise her arms above her head, Dee had to get a stockboy to help her get a cereal box from the top shelf. When he’d climbed up there, he turned to ask her if he’d gotten the right one and took a serious look down her dress. She moistened her lips a little and hungrily told him that was exactly what she wanted. He nearly fell off, and she noticed that he seemed to have some difficulty walking away. She thought she could see something pushing against the front of his smock, but it might just have been her imagination.

Dee was getting a real kick about being an object of male attraction, and only when consciously thinking about it did a little place inside David’s mind find it disturbing. These lessons in thinking of herself as a woman were working amazingly well. She gave the nice bagger who helped her get her groceries out to her car a peck on the cheek. She laughed at the foolishness of men and wondered if she’d ever been so easily led around by a pair of shapely breasts back when she was a man.

All in all, it was a great experience. She’s gone out in public, alone, and hadn’t felt the slightest bit insecure about being found out. She had been accepted as a woman unquestionably, and it really started her feeling like this whole thing might actually work.

***

Dee’s voice lessons were proceeding nicely. The more feminine she sounded, the more confidence it gave her, and the more comfortable she felt in her persona. Talking to strangers face-to-face, she had the advantage of her extremely female appearance. The various guys who had conversations with her cleavage never imagined that the person they were talking to wasn’t completely a woman.

Kay kicked up the difficulty by having her talk to people over the phone, where she couldn’t assert her femininity by jiggling her big boobs. A couple of times she was mistaken for a young boy, but some work to add a melodic lilt to her tone kept that from happening again. After a couple days working at it, she was consistently called “Ma’am.”

She called Vanessa, who didn’t even recognize her voice. Kay said to ask her for a special cocktail dress; she said that Dee was ready for a major milestone and she needed something special to wear. Vanessa asked if the ban on underwire bras was still in effect, and Dee didn’t know. She had to conference-call Evelyn, who also didn’t know who she was at first, to ask. She said that underwires were still out, because her implants hadn’t settled into their final location, so the bra would be trying to make them curve in the wrong shape. Vanessa asked if a custom underwire made to fit Dee’s breasts exactly would be okay, and Evelyn said it would. Dee then passed the phone to Kay, and she talked to Vanessa about their schedule, and they made a plan to go into the design studio after hours the following evening.

David had visited Claude’s workshop before, but always during regular working hours when the place had been full of people. It was spooky being there at night all alone, almost like a ghost town. Vanessa led them around to a workroom in the back. There was a wooden platform in the middle of the space with holes in it every so often, and some of them had metal pipes coming up out of them. It looked like some strange piece of industrial art.

Vanessa handed Dee a pair of shoes and a folded piece of clothing and directed her to a screen in the corned of the room, telling her, “Take off everything you’re wearing except your earrings and put these on. Even your underwear. Don’t worry; I cleared it with Dr. Coleman that it would be okay for you to go braless for a little while so we could do this.”

The garment turned out to be a silk kimono-style robe, a pretty print of hummingbirds on a black background, with stylish pink ribbon trim. It was very short, and she was grateful to be taped and tucked in place since otherwise things might have been hanging below the hemline. The shoes were strappy sandals with wedge heels that must have been at least five inches high. There was a circular hole through the wedge that almost made it look like a separate heel shoe.

It took a couple minutes for her to find her balance when she stood up from the little stool she’d been sitting on. After a few cautious small steps, she got her rhythm and executed a perfect supermodel strut over to the others. It was a different kind of feeling as her breasts bounced with every step, free from any kind of support.

Vanessa took her hand and had her step up onto the platform. She had her stand with her feet a few inches apart and her arms a little away from her sides. She took some measurements: the distance between her ankles, the height of her elbows from the floor, the length of her forearms, and then sent her off to a bathroom, telling her to go even if she didn’t have to, as it would be her last opportunity to do so for a while. Dee was a little confused but did as she was told.

When she got back, the pipes on the platform had been rearranged. She stepped up and returned to the approximate position she was in before. Now she was standing between two vertical pipes, and there were T-shaped things clamped to of them horizontally halfway up or so. Vanessa showed her that the tops of the T’s, which were padded with some kind of foam and covered in soft fabric, were for her to rest her forearms on. She fiddled with the clamps for a bit to get Dee’s arms into the position she wanted. Then she tied her arms to the boards with some kind of soft rope so she couldn’t move them. It was tight, but not painful.

Then she ran another pipe through the holes in Dee’s shoes. There were spacers like the clamps they use on barbells that kept her feet a fixed distance apart, and then a couple more clamps went on the outside of her feet so they couldn’t move at all. Then that pipe got attached to the uprights, and she was locked in place. It was scary, but kind of exciting being completely secured.

Vanessa explained that in order to make perfectly form-fitting clothes for her, she’d been instructed to make a casting of Dee’s body. She usually would have used a couple of assistants to do this, but since her situation was a Top Secret project, it would take a while. And to get a good mold, Dee would have to stay in position, and that’s why she needed to be attached to the frame. She twisted Dee’s hair up on top of her head and put a hairnet on her.

There was one more thing. She needed to be nude to get the best resolution. Vanessa pulled the ribbons on the sleeves of her robe, and the seams across the top came unlaced and she was naked to the waist. Dee twitched as she instinctively wanted to cover her breasts, but she was helpless. Vanessa untied the robe’s sash and it fell to the floor.

Vanessa let out a little wolf whistle and said she couldn’t get over how sexy a woman Dee had become. She took new measurements at her bust and waist and hips, pulling the tape extra tight. Then she noticed something and went over to her work table. Dee could hear water running, but couldn’t see what was happening.

Vanessa came back over with a few implements on a tray. She said there was one change she’d need to make for the casting to go smoothly. She dipped her washcloth in a bowl of warm water and ran it over Dee’s little pubic patch of hair. After spraying it with shaving gel, she ran a little razor over the area, first down, then up, dipping it in the bowl frequently. It was an extremely intimate act, and Dee was sure she was blushing everywhere.

Vanessa apologized and warned her that she’d be really itchy down there in a couple days, and that she ought to be obsessive about cleansing the skin in her bikini area in order to avoid painful ingrown hairs as they grew back. Dee asked if it would just be easier to keep shaving, but Vanessa told her that the stubble wouldn’t be as scratchy if she got a wax instead. Dee thought about maybe just going back to the laser place and getting it all off, or maybe trimmed a little narrower so she would look better in a smaller thong, or perhaps just get her square turned into a more feminine triangle.

Everything was ready. Vanessa rolled a work cart over, and started by running some metallic tape along the sides of Dee’s body from her underarms to the middle of her thighs. She said this was where the seam in the mold would be. Tape also went across the top of her shoulders and a little way up her neck. Dee blushed again when she ran the last section of tape around the inside of her thighs and across the tape she already had there. At least now all those parts were doubly-safe from popping out.

For the next step, Vanessa asked if Dee had any nut allergies, and she said she didn’t but it seemed like a weird time to ask that kind of question. She then took a spray bottle and started misting her all over with what she explained was peanut oil. This was to keep things from sticking to her too much. She worked it into the tighter crevices with a paintbrush.

Vanessa poured two kinds of stuff into a little pail and stirred it with a wooden spoon and made some blue liquid that kind of looked like paint. She started pouring it onto Dee’s body, covering her in a thin layer of this substance that dried into a kind of rubbery second skin. When Vanessa got to Dee’s nipples, it felt surprisingly good, and she involuntarily let out an embarrassing little moan. When her bucket was empty, Vanessa mixed up another batch and continued until Dee was completely blue from shoulder to mid-thigh.

Vanessa told her to look on the bright side; the casting would be of her whole torso with just a bit of her arms, legs, and neck. Sometimes they had to do the whole model from head to toe. She mixed a second coat thicker, and it was green instead of blue. She said this was so she could make sure she got it everywhere. The second coat also took longer too apply, and she was putting extra amounts in places where the mold would need more support.

The first work cart was rolled away and a different one brought over. Now Vanessa covered the rubber stuff with wet strips of cloth infused with plaster, as though Dee had broken every bone and needed a body cast. She asked if Kay wanted to help, since this part didn’t require as much precision, and she agreed since it looked like fun.

As the plaster strips went around her abdomen, Dee had to breathe more shallowly. She felt like some kind of cross between a mummy and knight encased in solid armor. The plaster gave off heat during its curing process, and she was glad to have the insulating rubber layer underneath.

Finally, after standing there for what felt like days and was probably at least hours, it was time for the mold to come off. Vanessa used a frightening little spinning cutting blade on the end of a rotary tool to cut through the plaster, promising that it couldn’t go through the tape on the bottom so Dee was perfectly safe. She had Kay stand behind Dee and hold the mold against her back while she cut. First she went down the sides, making a wavy line along the edge that she said would help with lining up the sides of the mold.

Then she very carefully cut along the seam between Dee’s legs, and tried to make a joke about offering to turn her female completely while she was down there, but it wasn’t funny even if Kay did laugh way too loudly at it. She finished off by cutting the seam at the top of each of Dee’s shoulders, and had to make sure she was supporting the plaster with one hand while cutting with the other.

As Kay kept the back half in place, Vanessa delicately pulled the front of the mold away from Dee’s body. It was weird to see what half of her body looked like in plaster form. After setting the first half aside, she relieved Kay of her burden and got the other half of the mold. Dee was surprised to be still covered in rubber, but Vanessa said it had to come off in two phases. The plaster was just the structural casing; the rubber stuff was the actual mold.

The cutting saw had marked the rubber, but hadn’t cut it completely, so Vanessa had to use a special knife to go back over the lines. Dee was grateful that she didn’t try to make that joke again when she had a knife close to David’s future children. When she was done cutting, she had to slowly peel the mold off, taking care not to tear it.

If it went wrong, they’d need to make a new mold. Dee really didn’t want to have to go through this process all over again, so she tried to help by staying as still as possible, but when her protective rubber sheath came off she was naked again and really really wanted to cover up. When both the front and back pieces had come off, Vanessa untied her hands and she could put the robe back on. (Its sleeves had been laced up again.)

Her shoes were freed from their harness, and she could finally move again. Her joints were so stiff from standing in place that she needed help walking. Vanessa guided her to a shower area she could use to clean off. She was still pretty wobbly, so Vanessa thought she still needed supporting. She pulled off her t-shirt, unzipped her jeans, and slipped out of her bra and panties faster than it took Dee to realize what was happening. Vanessa just shrugged and said it was only fair; she’d just seen Dee naked, and besides they were both girls.

Vanessa had a great body. Her breasts were not as big as Dee’s, but they were proud and perky and had thick, dark nipples that seemed exotic and mysterious to her. Vanessa’s rear end was magnificent. It was almost heart-shaped. Dee was just glad she’d been taking Kay’s special tea, so all she felt when looking at it was envy. Her narrow hips and flat buttocks just weren’t feminine enough.

She was really glad for the tea when Vanessa started washing her with a special solvent to get the tape off, and it also loosened her regular adhesive tape and Dee’s genitals came untucked. Her penis twitched a little when Vanessa cleaned the adhesive off of it, but fortunately did not become erect. She tried to apologize, but Vanessa just shook her head and said it wasn’t a problem. Dee was sure though that she had revenge on her mind when she was being extra thorough in deeply cleaning the oil and residue out of every crevice.

The hot water combining with the way Vanessa was rubbing her brought Dee’s legs back to life and she was able to stand on her own to finish the shower. Vanessa moved on to bringing feeling back to her arms and she was finally able to hold the soap on her own. She took off her hairnet and leaned back into the water stream, not caring that she’d be washing off her makeup and all she had in her purse were a lipstick and a compact. It just felt too good.

If that kind of pain from standing in place for hours is what models go through every day, she had a newfound respect for Maritza and her friends. That wasn’t a useful train of thought, so she shook her head a few times under the water to try to think about something besides missing her girlfriend. She wasn’t supposed to be thinking about any aspects of David’s previous life. But even behind an impressive bust, Dee’s heart still knew who it loved and wanted to be with more than anything. She figured that maybe if she cried in the shower Kay wouldn’t notice and get mad at her.

Vanessa looked at her funny, but figured it had just been a stressful day and leaned in to give her a hug. Embracing a naked woman without so much as a stirring downstairs was a strange sensation, and she just had to laugh when their boobs smooshed together. The laughter was infectious, and by the time they’d finished and gotten dressed again, it was a pair of giggly schoolgirls that returned to Kay.