Oscar Night by Jennifer Brock David Fine was a novelist who'd twice been nominated for an Academy Award for adapting his stories into screenplays. The last time he'd worn a red tuxedo that had been designed for him by his good friend the designer Claude Marsh. Fashion reporter Jane Waters had made a rude comment that colors were only for gowns, and David had joked that he'd wear a gown if he was nominated again. Claude had orchestrated a plan to turn David into a stunning vision of glamour and grace in his gown, by becoming as believably female as possible. With some encouragement from the girlfriend Claude had introduced him to, David even went so far as to undergo some surgical alterations. Under the tutelage of Kay Thomas, our heroine "Dee" has been learning how to become a woman. It's Friday morning, the Oscars are in two days, and Dee has just had a romantic experience with a man the night before.

Part 20

Dee awoke feeling ashamed. She’d given a man oral sex, and it was only her sheer incompetence as a seductress that kept her from taking it even further and bringing a man into her bed. But even so, a penis had been inside her. She’d swallowed semen. She had brought a man to orgasm with her mouth, and she’d liked it. It had given her a sense of accomplishment, a feeling of pride in a job well done (so to speak), and there was no getting around that.

Did this mean she was gay? That David, her true male self at the bottom of her psyche, was gay? Would he be able to go back to the way things were before? And what about Maritza? David had a girlfriend he was very much in love with, and it wouldn’t be fair to her if Dee was going to be looking to get penises stuck into all her various orifices. But did Dee really want that? She didn’t know; it was all so very confusing.

Dee tried to visualize her girlfriend naked, to try to see if that image still turned her on, but the megadose of anti-libido herbs she’d taken before bed seemed to be working too well. Thinking of sex with women didn’t do it for her, but neither did thinking of sex with men. She couldn’t even get aroused by playing with her nipples. She still had more questions than answers. She wasn’t sure if she was more ashamed for trying to bring a man into her bed or for failing to.

Male or female, gay or straight, she had no clue about who she or he really was anymore. Kay wasn’t even there to talk to about this. Dee just wanted to sit in the corner of her room and cry. That wasn’t going to solve anything either, though. She forced herself to get up and start her day, starting with a painfully hot shower.

While washing, she noticed that she could still feel the lubricant that she’d applied up inside her. She stuck her beauty bar in there as far as it would go in order to clean it all out. She plunged it up and down a couple of times before she realized that she was having sex with a bar of soap and pulled it out and felt even dirtier.

She had to stop, get out and go use one of her disposable enemas and clean herself out before she felt pure enough to finish her shower. She exfoliated herself pink with her loofah under the hot water, and gave her hair a good wash and conditioning. After drying and applying lotion to most of her skin, she tucked and taped up her offensive male parts, using extra tape. She blamed her libido for the mess she was in, and was essentially punishing her genitals for her behavior. To make things as difficult for them as possible, she put on her most constrictive tiny thong panties, and then her tightest pair of jeans, which needed her hip and bun pads to fit properly, so she pulled on her padded girdle and then her jeans.

She selected a nude seamless demi bra and wore a tight red tank top that had a generously scooped neckline. It showed enough cleavage to be sexy without looking slutty. She tried to roll a pair of knee-high stockings up her legs, but then realized her pants were so tight she needed to have her hose on first, so she had to take them off then put her stockings on, then pull them back on. Finally she was able to slip her feet into a pretty yet comfortable pair of brown leather ankle boots.

She checked herself out in the mirror. Even without makeup and with her sleeper earrings as her only jewelry, she looked pretty good. The person in the mirror was clearly female — not only were there no bulges where they didn’t belong, but her jeans were so tight it made you think you could almost make out the contours of her cleft. Dee even knew that it was impossible, but the seam running across there made the illusion believable.

She wasn’t petite by any stretch of the imagination, but she was well-proportioned. Her girdle had pulled in her waist and padded out her hips to give her a 38D-29-34 figure, not a perfect hourglass but close enough to look sexy. In three-inch heels she stood five-eleven, tall for a woman but not outside the natural range. Her tank top left her shoulders bare, but rather than calling attention to the fact that they were a little more square than they ought to be, somehow isolating them minimized the problem. She hadn’t done anything with her hair, so it hung in a mass of chestnut waves down her back almost to the spot where the clasp on her bra made a little bump in the back of her top. She smiled at the pretty girl in the mirror.

She grabbed a scrunchie and pulled her hair back into a ponytail. She wasn’t planning on leaving the house, so she left her sleepers in and didn’t add any other jewelry. But she did feel a little naked without any makeup, so she sat at her vanity to pick out a lipstick. It was then that she noticed she still had extremely slutty fire engine red nail polish on her hands.

She almost had another breakdown at the reminder of how far she’d gone to try to snare a man, but shook it off. She did know she needed to change her nail color, though. She pulled out a bottle of nail polish remover and some cotton balls and set to work cleaning the red off her fingers. For the sake of completeness, she needed to do her toes, too. She took off her boots, and then removed her jeans so she could get her knee-highs off.

Dee wanted to pull her jeans back up once her feet were bare, just to maintain that tight pressure, but they reduced her flexibility too much for her to touch her toes. She had to take them off and do her pedicure in her panties. That made her a little uncomfortable, so she put on her short red silk kimono-style robe to provide just enough coverage while still allowing her knees to bend.

She got out her pedicure kit and gave her toenails the full treatment. She started by removing the offending polish. Next she trimmed, filed and buffed her nails, and used an orangewood stick on her cuticles. Then it was time for new polish, so she stuck the squishy foam separators between her toes and applied first a smoothing base coat, then two coats of the new color (she’d settled on a dusty rose pearlescent polish), followed by a clear protective topcoat for added sheen.

While waiting for her toes to dry, she continued each step on her fingernails, too. The whole process ended up taking about an hour. Sitting there in the middle of it all, Dee reflected on how natural it felt to do, not weird or strange at all. What was odd was to think was that just a month ago she’d been a guy.

After her toes were completely dry, she rolled her stockings back onto her feet and put her jeans and boots back on. She picked a lipstick that matched her new nail color, and brushed a little mascara onto her lashes for good measure. She finally felt completely dressed.

There were still a couple hours before Kay was expected back, so to make the clock go faster as well as to burn off some of the angry energy still in her system, Dee decided to do some housecleaning. She started by stripping the sheets off her bed and throwing them into the washer. She wanted to eliminate the clinging scent of desperation.

While the machine was busy, she hand washed some of her delicates. She wanted to purify all of her undergarments from the night before. Unfortunately, the dress she’d worn was dry clean only. She tried to hide it by hanging it off on the side of her closet with some other things that needed to go to the cleaners. The rules for her complex didn’t allow outside clotheslines, so she had to unfold her indoor drying rack for her lingerie.

When the sheets moved to the dryer, she threw a load of towels into the washer and set to work scrubbing the bathrooms. The tight pants made it painful to bend her knees, but Dee felt she deserved it. Housecleaning had always been a way for David to clear his head whenever he got depressed, and it still worked. At least that hadn’t changed, even when so much else had. It also gave Dee a warm feeling to see the yellow rubber gloves she was wearing to protect her manicure were the same kind her grandmother used to wear for doing chores.

By the time Kay showed up, Dee had changed the bedding on both her own and Kay’s bed, gotten all the bathrooms sparkling clean, vacuumed the carpet on the second floor and the area rugs on the first, polished the hardwoods, and finished most of the dusting. Kay scolded her for overexerting so close to the day of the big event, but Dee said she had a lot of energy that needed to be worked out.

Dee had wanted to keep things private, but she really needed to talk about what was bothering her. It wasn’t long before she broke down and started sobbing in front of Kay. “I messed up, and ruined everything!”

Kay wrapped her arms around her and held her tight. “What did you ruin? The place looks sparkling.”

“No, with Joe. Last night. I’m horrible.” Dee sniffled between sentences, and made little sense.

Kay gave her a soft pat on the back and held her for a few minutes. “Okay, now start over slowly, from the beginning. What went horribly wrong with Joe? Did he get fresh with you?”

“No, I did.” Kay’s confused look made her continue, “I’m a filthy whore, a cheap slut, a dirty skank.”

Kay interrupted before she started on another crying jag. “You are no such thing. You are a good person. I can’t imagine why you don’t think so. What happened?”

Dee gave her the full story of everything she’d done with Joe, even showing Kay the note where he called her “a first-rate cocksucker.” She’d let a man she barely knew penetrate her body, on the first date. And she would have let him do more if she hadn’t taken so long getting ready, making herself cleaned out and lubed up for him. She was no better than a common street whore.

Kay let Dee feel sorry for herself and cry it out for a while, before trying to snap her out of it. “Honey, you did nothing wrong. You’ve just been programmed by an archaic chauvinistic society that shames women for the same things that it praises men, sexually. You had every right to experiment with Joe, and it doesn’t make you morally flawed to have done so. You were a consenting adult who understood what you were getting into. Not every bedmate has to be a soulmate. But going by your reaction today, it’s probably a good thing you didn’t take him into your bed; you clearly weren’t ready for it, and I’m sorry if I pushed you too far. Do you think you can get past this? I’ve only got one more lesson for you, and it’s a fun one.”

Dee nodded to let her know she understood, and muttered that it wasn’t Kay’s fault. She tried to put on a smile, but it was a weak one.

Kay dragged her upstairs to change for lunch. She had her strip down to just her panties and then squeezed her into a corset again. Dee had almost forgotten what it felt like, but soon remembered how to breathe in it without hyperventilating. Kay checked with the tape measure, and Dee was down to her 26-inch target. She couldn’t bend to touch her toes, so Kay had to roll her stockings up her legs for her, but Dee was able clip them to her corset’s garters by herself while Kay was buckling on her three-inch sandals.

The outfit Kay had picked out for her was a tiered cotton peasant skirt with pretty eyelet lace trim. Dee got to go braless, but wore a frilly champagne satin camisole under her sheer white chiffon blouse. She was told to skip foundation, but made up her eyes fully, with mahogany mascara and eyeliner and rose eye shadow that matched her nails and lips. She felt that her ensemble seemed a little gypsyish, so she chose wide gold hoop earrings and loaded her wrist with bangles, and found a cute gold pendant of a filigree turtle to crawl around in her cleavage.

Kay took out her scrunchie and brushed her hair out to its fullest volume, and gave her a few sprays of perfume. Dee grabbed her bone leather shoulderbag, and transferred all her essentials into it, and she was ready to go. A quick check in the mirror revealed a look that would have been very “Southern California” if only she was a little tanner and very much blonder. But she did have the requisite percentage of silicone body mass. She chuckled to herself and smiled a genuine smile.

Kay drove them a ways out from the city, to stop for lunch at a taqueria set up in what was probably officially a vacant lot. A trailer, like from a carnival concession or a jobsite caterer, was set to one side where people would place their orders at a window, and there were a number of plastic café tables and chairs arranged around the lot.

Kay told Dee to grab a table while she went up to place their order. Dee tried to find the cleanest, least wobbly of the vacant tables. Her spiked heels were not that suited for the packed dirt on the ground, but she managed to make her way without any mishaps, other than a few whistles from one of the patrons, a large Latino man who appreciated the way the wind was blowing her skirt around. She regretted her choice of a thong.

Before sitting down, she took out a sanitizing wipe and reduced the grime on her chair, grateful for paying attention to the lesson on how to keep a well-stocked purse. It also seemed like a good time to put on her sunglasses. Even though it would give her admirer more of a show, she also wiped down a chair for Kay, and did what she could to the tabletop.

Dee wasn’t waiting very long when Kay returned. She set a divided Styrofoam clamshell dish, a chilled bottle of water, and a paper napkin with a plastic fork and spoon in front of each of them. Dee opened hers and saw a pair of tasty-looking enchiladas covered in cheese and sauce, with a reasonable portion of spicy rice and refried beans on the side. It seemed more appealing than anything from Taco Bell, despite having to eat it outdoors.

Kay said that for this part of the challenge, Dee needed to figure out how to eat sloppy, messy food and still seem daintily feminine. And to add to the challenge, she had to do all this while the billowy outfit Kay had put her in was blowing around in the wind, and also while she was essentially on display out in public, to both passing cars and the questionable people around.

Dee accepted the challenge, and tried imitating Kay, but she’d planned ahead and gotten a much neater lunch for herself, a burrito and quesadilla she could pick up in her hand and nibble delicately. She decided to start by eating her rice and beans, since that was easy. She was able to keep her spoonfuls relatively small.

Her hair was whipping around in the wind, and kept going in her mouth. She was really annoyed that Kay had insisted on taking her ponytail out. She rummaged a little through her bag, to see if she had an elastic or barrette or something, but it seemed that she’d been sabotaged. She grumbled and glanced over at Kay, who was grinning smugly. Dee thought back at all the tricks she’d seen Maritza do, and shot Kay an evil grin of her own before pushing her sunglasses up onto her head to hold her hair down.

Freshly following that victory, she felt confident enough to try to conquer her enchiladas. She was quickly thwarted though, when she couldn’t cut it down to bite-sized pieces with either her dull plastic spoon or her fork. She carefully smoothed her skirt, stood up, and walked over to the trailer. On the other side of the window was the cook, working in the kitchen. She tried to get his attention, and ended up having to lean over to give him a great view, and he just gave her a confused look. She took a moment to remember the right word, then made a cutting motion with her hand and said, “ ¿Un cuchillo, por favor?”

He smiled broadly and pulled out a white plastic knife from a bin and handed it to her, giving a little wink. Dee let her fingers brush his hand as she took it, and did her sexiest sashay back to her table. She could almost feel his eyes on her behind as it swayed. She settled back into her chair and had no trouble slicing her enchilada into pieces that she could eat without making a mess. She had defeated Kay’s challenge! It felt good to win, and almost made up for how awful she’d felt that morning.

When they got back in the car, Kay explained that the real lesson would be starting soon. Dee thought the lesson was just about eating in public, but Kay’s full plan was sneakier than that. They’d gone out for Mexican for lunch in order to prepare Dee for the afternoon’s lesson, in how to deal with “involuntary bodily noises.” Dee laughed when she decoded Kay’s euphemism.

The lesson actually turned out to be fairly useful. After teaching Dee the secret that all girls learn of how to suppress “intestinal noises” (basically, clamp it down until you can get to the ladies’), Kay used some powder on her and taught her a technique for sneezing cutely without sending it through your vocal chords but instead just making a high squeak. Similarly, she was taught to yawn without making a noise. Using her full male vocal chords for any of these unplanned sounds would give her secret away.

The trickiest part of the lesson came after Kay had her drink this gooey stuff that tickled her throat. It was very tricky trying to keep her voice in the higher range while coughing. She had to settle for a quiet whispering kind of cough that wasn’t very effective at clearing her throat. Being strapped into a corset didn’t make it any easier, either. Just when Dee thought that the lesson would go on forever, Kay decided they needed to stop before she went hoarse.

They took a break for a light supper. Dee took some frozen breadstick dough and soup from the freezer, and threw together a fresh green salad while they were cooking. The kitchen was definitely her domain; Dee was back in her element. The meal came together nicely. Kay said she’d miss her cooking when she left, and until then Dee hadn’t really been thinking about it. In only two days her lessons would be over. What would her life be like after Sunday? She had no idea.

On the subject of Sunday, Kay asked Dee if she’d written her acceptance speech yet. Dee was fairly sure she wasn’t going to win, so she hadn’t given it much thought. And since her laptop had been taken away and locked up, she couldn’t do it anyway. Kay pointed out that she had plenty of pieces of paper available to write on, but Dee said she needed her computer to write; nothing else was comfortable. Anyway, in the extremely unlikely event that her screenplay won the prize, she knew who needed to be thanked and shouldn’t need to write it down.

As it was, Dee only had a little time to herself after dinner. Kay told her she had another appointment with Jeffrey and Tomas. They drove over, and the salon was surprisingly busy for a Friday night. The other ladies there must have also needed to get ready for the Academy Awards, or related events. There were hundreds of parties planned for Sunday night in the greater Los Angeles area.

Kay said the appointment was in her name to preserve Dee’s secret identity. So when the receptionist asked for “Ms. Thomas,” she had to stand up and follow her. Dee was uncomfortable being surrounded by so many strangers undergoing special private procedures, and tried not to look around too much either along the way or when she was shown to a chair. Eventually she saw a friendly face. Jeffrey showed up and gave her a half-hug and an air kiss hello, and introduced Dee to Chrissie, a young blonde who would be giving her a manicure and pedicure. He gave Chrissie a special bottle of nail polish and told her to give it back to him personally when she was done; no one else was to get Dee’s color even if they asked for it. It made her feel pretty good to have an exclusive shade all her own.

Chrissie did a great job. And just like always, getting a pedicure really helped Dee relax. In fact, she almost fell asleep when Chrissie was rubbing lotion into her soles. Or maybe more than almost. She closed her eyes for what seemed like a moment, but then Chrissie tapped her shoulder and she opened her eyes and saw that her finger and toenails were now a deep wine color, with a shimmering topcoat that was almost black. Chrissie told her she was finished, and brought her to another part of the salon to wait in a chair.

At the second station, a new girl named Tawny gave her a mild facial. A full treatment would have left her skin red and puffy and it might not have been back to normal by Sunday, so she only got a deep cleansing and moisturizing without the active exfoliation that normally came with it.

Instead of another assistant, this time Dee was taken care of by someone she knew. Tomas came over and gave her a friendly greeting before trying to explain what he’d be doing to her hair. Dee didn’t have the vocabulary to understand all of it, but the gist was that he gave her highlights a touchup, and then set it to add a little more body, and finally gave her a cut into a slightly different style. When he finished, he gave Dee strict orders not to wash her hair in the next two days; it would be easier to style if her natural oils were still in it.