Oscar Night by Jennifer Brock Last time, fashion model Maritza Delgado gave her boyfriend a trip to a day spa as a present to commemorate their first six moths together. This time it's novelist/screenwriter David Fine's turn to give her a gift. This installment does contain some actual cross-dressing, although probably not as much as some of you were hoping for. (David's best friend, clothing designer Claude Marsh does not appear in this section, but he's probably still scheming somewhere.)

Part 5

After David had experienced his first facial, Maritza convinced him to add a cleanser and moisturizer to his nightly regimen in order to keep the fresh look. It was a bit of a hassle, but he had to admit the results were worth it. It dealt with all the grime of living in the city, and gave his skin a healthy glow.

The following weekend it was time for David to give Maritza her anniversary present. He wouldn’t give her any more information about where they were going other than that she should wear comfortable clothes and flat shoes.

He’d programmed their mystery destination into his GPS and wouldn’t tell her. And the further out of town he drove, the more frustrated she became over not knowing, particularly because he wasn’t driving fast enough for her. She was almost ready to make him stop the car so she could get out, when she saw that they were headed for the speedway.

Maritza was livid. “Your big surprise for me is to go see a NASCAR race? We’re going to drink lame American beer with a bunch of hicks and watch cars drive in a circle? Do you know nothing about me? Why would I want to just sit around and watch something? That’s not me at all! And this race must not be popular, because this parking lot is practically empty. Who’s racing today, anyway? It must not be anyone I’ve heard of, like that Jeff guy or that other guy who’s the son of the guy who blew up.”

David tried to calm her down. “That’s not a nice way to refer to someone.”

“Is it my fault I don’t know his name? Anyway, it’s a really bad surprise. Can we just go home?” She turned away from him and pouted.

“Hey, cheer up. I think you’ll know at least one of the drivers out there today.” He tried to turn her face toward him and she slipped out of his hand.

“I don’t believe you. Anyone I’d know would have drawn a crowd.” She crossed her arms over her chest.

“The parking lot is empty because there’s no race today.” She tried to interrupt, but he cut her off. “But what is open today is a driving class, where actual racing professionals teach amateurs how to drive race cars, and I enrolled you in the class. Because you don’t watch things, you do them. And you love to drive fast, so here’s a place where you can go as fast as you dare.”

She looked at him through slitted eyes. “Really?”

“Really. I know your present for me was something we could do together, but this is something for you to do and me to watch. Now as soon as you apologize to me, we can go check you in.”

“Apologize? What for?” She put on an innocent face and batted her eyelashes.

“You are so difficult sometimes!” He leaned over and stole a kiss. She melted into it and grabbed his shoulder.

She broke the kiss and gave him a playful nip on the chin. “Making up is half the fun in fighting.”

He tousled her hair. “I swear. If I wasn’t so in love with you, I don’t know how I could put up with your moods.”

She grabbed him for another quick kiss. “When do I have to check in? Is there time for a quick trip to the back seat? (It is the one good thing about your car.)”

He checked his watch. “I don’t think so. You can thank me for my present later.”

“Oh, this wasn’t for my present. This was to mark the first time you said you loved me.” She kissed him again.

“I did? Oh, I didn’t realize I hadn’t said it before. I knew how I felt about you almost from the start. Couldn’t you tell?”

“Sure, but sometimes a girl likes to hear it.” She gave him another kiss and then stepped out of the car. He sighed and looked at her, his Venezuelan goddess, standing there looking no less glamorous in her faded jeans and tank top than she does on the catwalk. A little voice inside him cried out that boys like to hear it, too, but he shut it down. He took a deep breath, adjusted his sunglasses, and opened his door.

They walked across the lot to a glass door in the back of the building, with a sign that let them know it was the right place. A cute twentyish brunette wearing a NASCAR t-shirt was sitting behind a simple desk. She looked up and pulled a laminated card on a lanyard off of a stack and held it out to Maritza. “Show this pass to the security guard and you can get into the stands to watch your man drive. They’ll be in class for a couple hours before they hit the track if there’s somewhere you want to go in the mean time. Guests are welcome to join us for lunch.” She turned her attention to David, and picked up a clipboard. “Your name, please?”

David took the pass from his girlfriend and spoke up. “You’ve got it backwards. I’m the one here to watch. She’s here to drive. Her name is Maritza Delgado, although it’s possible they put the reservation in my name since it went on my credit card. I’m David Fine.”

The confused girl looked at her list. “I wasn’t expecting any girl drivers. We do get them occasionally. Ah! I see the problem. You must have made the reservation by phone. I had you down as ‘Mauricio,’ you know like the Formula 1 driver Mauricio Gugelmin? Oh well. Go through that door and Jim will tell you what to do.” She pointed.

Maritza thanked David again for her present and kissed him goodbye. He put the guest pass around his neck and returned to the parking lot, where he got his computer bag out of the trunk. He walked over to the front gate and showed his pass to the security guard, who wrinkled his nose at David. “I didn’t know your kind liked racing. The rest of the wives and girlfriends usually like to watch from the luxury seats in Row Four. I’m sure they’d love for you to join them,” he said with a sneer.

David didn’t feel like correcting the guy. He just sighed and shook his head as he walked away. He decided to go sit with the other spectators anyway, figuring he’d correct any misconceptions they had based on his appearance if it mattered. He found the spot and the only one there was a bottle blonde overflowing from her low-rise jeans sitting there playing with a baby that was sitting in a car seat. David gave her a little wave when she looked up, but he took a seat at some distance.

They were out of the sun, but the air was dry and kind of polluted, so he took a bottle of moisturizer out of his bag and did his face, his hands, the back of his neck, and his arms where they stuck out of his sleeves. He’d just taken his laptop out and was searching for a wi-fi connection when his phone rang. Maritza had texted him, “Need u now. Meet in lobby. Urgent.”

He zipped up his bag and ran out of the stadium. He hoped it wasn’t something too terrible. Maybe the class was a bunch of rednecks who didn’t want a woman there. Maybe they’d become violent, or worse. If anything had happened to her because of a “present” he’d given her, he didn’t think he could live with himself anymore. He didn’t even have time to hear the epithets the guard threw at him on his way out.

He was out of breath when he made his way back to where he had left her. She looked fine, so he was relieved. She was wearing a real racing jumpsuit and looked like a professional driver. He couldn’t see anything wrong and wondered what the urgency was. She pulled him into the ladies’ room and started getting undressed.

As soon as he caught his breath David told her, “You had me worried that something was wrong with your urgent message. Not that I’m complaining, but if it was just a booty call you could have warned a guy.”

Maritza laughed. “No, no. I didn’t call you here to have sex. Now take your pants off.”

He was confused and just looked at her.

“I need your underpants. These suits may be fireproof, but it’s really itchy to sit in with bare skin. I don’t think a lot of NASCAR guys wear thongs. I want to trade underwear with you.”

David just shrugged and did as he was told. He slipped off his shoes and dropped his pants. Watching his sexy lover wiggle out of her jumpsuit made his little friend stand at attention. “Are you sure you didn’t call me in here for sex?”

She leaned down and lowered his silk boxers then planted a kiss on his disappointed member. “Sorry. There’s no time.” She handed him her pink lacy thong, still warm from where it had cozied up to her most intimate of places. “But you may need to take care of that yourself before you can fit in these.”

He looked down at the tiny panties and considered “going commando,” but he thought his jeans might be a little rough on his hairless genitals, so he tried slipping on the thong. And just like she predicted, it really didn’t fit over his erection. He looked over at her and saw that his underpants made her look much sexier than hers looked on him. She zipped up her jumpsuit and put her sneakers back on, then thanked him and kissed him goodbye.

David was stuck in a ladies’ room with a raging hard-on and miniature underpants. It probably wouldn’t be a good idea for him to hang around in there for too long. Lacking a better idea, he took Maritza’s advice and went into a stall. He pulled his panties to his knees and sat down on the commode, then took matters into his own hand.

It was lucky that he’d just moisturized. It made his hand soft and slick. That combined with the extremely recent memory of his girlfriend’s naked posterior made it very easy for him to get himself off. He stroked softly at first, but then built up in intensity. When he felt ready to explode he aimed at the bowl. He got a few drops on his fingers, but he licked them clean before grabbing some toilet paper to wipe himself. He was able to fit in the tiny thong, although somewhat uncomfortably. It reminded him of all the wedgies he’d gotten in middle school.

He was walking kind of funny when he returned to the security checkpoint, and the guard had a few more choice words for him. He tried to ignore them as he sashayed on back to where he’d been sitting before.

The young mother eventually introduced herself as Kirsty and her baby as Billy Junior. Billy Senior was down in the class. She looked askance at David and asked who he was there with, and he told her his girlfriend loved to drive fast so he got her the racing class as an anniversary present. Kirsty seemed to relax when she realized he wasn’t some “weird homo pervert” or whatever she’d assumed about him.

More spectators showed up as the morning drew on. Bonnie, an older heavyset woman, was a housewife from Wisconsin who’d planned their trip to California around the racing class she’d bought for her husband’s retirement. Laurie was a businesswoman overdressed for the occasion. She was bored and clearly didn’t want to be there, but it was important to her son that she be there to watch. Heather was a brassy redhead in a tight t-shirt and extra-small shorts, who was there to watch her boyfriend Bucky learn to race. She explained that he had a dream of becoming a professional racer, so she’d saved up her tips for months to get him there.

Andrea was a nervous mouse of a middle-aged woman who looked like a schoolteacher or a librarian. David smiled to himself when she pulled out a paperback copy of Condensation to read while she was waiting. He tried making conversation and asked her if she thought it was a good book, and she said she wasn’t sure if it was the kind of book a person like him would enjoy. He tried again and asked if she knew the movie would be coming out in a couple of months, and she looked him over and decided that he must be in the business, so she went off on a rant about how no one in LA reads anymore. David just decided to back off and leave her alone.

He couldn’t find a wireless internet connection, so he just settled back and worked on some writing. His publisher was holding back on releasing Deposition, his latest book, to see how Condensation the movie did first, so they’d know how much to brag about it being from the same author on the cover. They were already entertaining studio bids on the new one even before it was published, so David was getting an early start on adapting the screenplay.

He got through two-thirds of his computer’s battery when a voice came on the loudspeaker to get their attention. The students were going to do their first laps on the track. Everyone stood up and cheered when their respective drivers went by. They weren’t going all that fast, but it was still thrilling to watch. The announcer identified his sweetie as “Mauricio Delgado,” to match what the receptionist called her, but it got him some odd looks from the others. David had to explain how it was a joke based on a clerical error, but it didn’t look like they believed him. He said that if they were going to be around at lunchtime they’d see that she was definitely a girl. He was tempted to show them a picture of her on his phone, but he didn’t want to come across as pushy.

The students each did another couple of slow laps, then they went back to class to talk about what they’d done wrong. David and the women talked about how each other’s drivers had done on the track. Heather was a little worried that Bucky hadn’t seemed to have done as well on the turns as some of the others. Kirsty told her not to fret about it; this was Billy Senior’s fourth time at the track and he still wasn’t cornering properly. She told David that he should be proud of “Maria” as she seemed to be handling the turns like a natural.

Lunch came from a silver catering truck that pulled out onto the track where some picnic tables were set up so they could look at the cars while they ate. It was a variety of unhealthy foods served buffet style from oblong tinfoil dishes, fried chicken, French fries, coleslaw, and biscuits. At least they offered bottled water as well as soft drinks.

David made a big point of giving Maritza a passionate embrace and a deep kiss when she came out, as a way to assert his heterosexuality, even if it did make his panties particularly uncomfortable. They sat down and introduced everyone around. Billy Senior didn’t look as redneck as David had imagined; he seemed like an ordinary guy in his thirties, with a decent vocabulary and no hint of an accent. He said he was in real estate, and asked David what he did.

David said he was a writer, and Maritza stepped in and outed him, talking about his books and his movies and giving his full name. He caught Andrea looking embarrassed at the realization, and tried to shrug it off with an apologetic glance.

Bonnie’s husband Ted was a big man with a full beard that would probably look more at home in a lumber camp than a racetrack, but he had the wide-eyed smile of a little kid at being allowed to play with the racecars. Andrea’s boyfriend Chuck was a surprise. He was a slick charmer who was “between jobs, but some investments were about to pay off.”

Laurie took out a box lunch of something green and sprouty to share with her son Nathaniel. The race school had been a present for his twenty-second birthday. When Maritza opened her jumpsuit and ate in her sweat-soaked tank top that left very little to the imagination, Nathaniel kept staring at her when he thought no one was watching. Then Kirsty started feeding Billy Junior and Nathaniel couldn’t decide which breasts to peek at.

Two buddies Pete and Rob had come to the race school together and had left their wives at home. They were in computers or something. David didn’t pay too much attention; he was distracted by the sensual way Maritza was licking her fingers.

Bucky, who was exactly the stereotype David had expected complete down to the tobacco juice he kept spitting, sent Heather out to get a six-pack. The head of the school wouldn’t allow any drinking and threw them both out. They all got in a shouting match in the parking lot, and the teacher came back alone and apologized to the others for having to hear it.

David got another deep kiss when the group broke up after lunch, and the drivers went back to class, and their guests went back to sit in the stands.

When the cars came back out this time, they went at full racing speed for ten laps of the track. This was much scarier to watch. Even though there were experts in the passenger seats, the amateurs were driving. The cars went by so fast, it was a blur. Everybody cheered for every driver this time.

Then there was an intermission, which most of them needed. Nervous energy can really make you have to go to the bathroom. David opted to sit in a stall so that in case some other guy walked in he wouldn’t see his panties. But he had a problem when he was done because seeing the pretty lacy wisp of cloth between his silky smooth legs was turning him on, and he had to wank off again to get it to fit in his panties. He tried adjusting things for a more comfortable fit, but it just wasn’t working.

After intermission, the drivers came back for another ten laps, this time correcting all the mistakes they’d made the first time out. The spectators all stood up and went down to the railing for a closer look. While Andrea was watching Chuck zip by, David snuck her book out of her purse and autographed it, writing “To Andrea: It’s good that someone in LA still reads — David Fine.”

After Maritza did her laps, the announcer came on the loudspeaker and said that she had the best time for the day. David was very proud of his sweetie. None of the racers who came after her beat her time. She ended up winning a little plastic trophy. They made her pose for a picture of it being handed to her, and she had David play the part of the racetrack beauty queen and hand it to her in the photo.

Since she’d beaten all the boys on the racetrack, they agreed to let her have the locker room alone so she could hit the showers first. She dragged David in with her. Driving like that had really gotten her turned on. She peeled off her jumpsuit, her sweat- drenched tank top, and David’s soaking wet boxers. He was too slow for her, so she helped him get his clothes off, and laid him down on the plank bench in the locker room. He was ready for her, so she easily mounted him and held him against the bench while she flexed her knees to bounce up and down on his shaft.

Her thumbs began to tease his nipples as her hips rocked around in a circular motion. He tried to buck his hips back toward her, but he didn’t have a wide range of motion available. She arched her back and began to tremble, and he realized how close to orgasm the engine must have brought her, if she was getting off this quickly. It was the first time she came first without him having to hold back his own climax.

She collapsed upon him and kissed him, working her lips all over his face, from one ear to the other and then from his forehead to his chin. He answered her passion with his own. She dismounted him and took him by the hand into the shower area, which was an open space with a row of nozzles like you always see in prison movies.

She chastised David for failing to bring their quality soap and shampoo with him; they had to make do with the inferior industrial-grade stuff that was provided so they went quickly. He offered to wash her back for her and she took him up on it. When they were all clean, she couldn’t put her sweaty clothes back on, so she put her jeans on without any panties, and wore a souvenir t-shirt instead of her original tank top. She even put her sneakers back on without any socks.

David’s boxers were too wet, so he had to put the thong back on. She said he looked sexy in it and declared that he should wear panties more often. He wasn’t sure about that, and got his pants back on as quickly as he could. At least the embarrassment kept him from getting another uncomfortable erection.

Maritza thanked the instructors for a fun day, and David placed an order for a DVD of the experience for her, that they’d be editing together from footage taken by cameras both inside and outside the car. They went back to his car, and she thanked her boyfriend for such a perfect gift. He agreed to let her drive home, if she promised to go no more than five miles above the speed limit. She negotiated him up to ten.