Megan & Kasey - Job Training Ch. 03

CHAPTER 3: PRETTY WOMEN

AUTHOR'S NOTE: Dear readers, as there are a number of characters, I thought it might be helpful to have a quick guide as a reminder:

• Walters: Geometry teacher, glasses, mustache, average height, 50s, beer belly but not fat.

• Sal Peterson: School janitor/maintenance, heavy set, mid 40s, strong

• Rothman: Father's boss, used to babysit for him; successful, fit, on the verge of divorce, 46

• Quigley: Local businessman, Megan's mom's client; early 40s, lean, tall, former athlete

• Hanson: Neighbor; 50s, slender, sickly, made money on stock

• Yelton: Photographer who took team and senior pictures, 38, biracial, beard, average build

• Granderson: Kasey's dad

• Meeks: Plastic surgeon who did Megan's mom's facelift. 50. Gray hair. Handsome, classy, distinguished. Silent owner of strip club.

• Darrell: Pizza guy, mid-30s, a little chubby with glasses and thinning hair.

• Jock and Muscles (Miles and Joshua): Joshua, black, 6-3, 35, elite athlete. Miles, football player, 6-6, late 30s, co-own gym together and both work as security at Meeks strip club.

• Bud: Met Megan at the carnival, early 50s, black, short and stocky, sick wife, faithful to her, jerks off to videos and pics of Megan, great laugh and smile

• Jim: 22, about 6 feet, pudgy, basketball shooter at carnival. glasses, nice

• Tom: Middle-aged, sandy colored hair, pudgy but not fat -- dad bod, glasses, realtor, rode with Megan on Tilt A Whirl, but very respectful

• Pierce: Defense trainer, very tall, late 30s, powerfully built, short dark hair, strong jaw line, dominant, intimidating

• Mason: Washing machine repair guy; middle-aged with dark hair that had bits of gray in it. About six feet tall with glasses and a goatee. He had a big round belly and friendly smile.

• Jackson Potter: Target employee, 17, senior to be at Megan's school, does the web site

• Michael Brandt: Megan's father who works for Mr. Rothman

• Susan Brandt: Megan's mom; Meeks is her plastic surgeon and Quigley is her client

Megan stood next to Mr. Rothman in the security line at the airport. She bit her lip nervously as she watched people empty their pockets, remove their belts and their shoes and go through the detectors. Mr. Rothman was already taking his shoes off and emptying his pockets. Megan, though, stood still, biting her lip nervously. She knew she would have to take off her shoes. There was no way around it. She also knew that her pussy and ass would be on display when she did. And not just for a second or two. No, the heels that Rothman had instructed her to wear, had lace-like straps that wrapped around her ankles. They would have to be untied and unwrapped. It would take time. She should already be doing it, but she was scared.

Excited and nervous lying in bed the night before, she had thought mainly about Rothman and Tanaka and a hotel room and what exactly might happen. In the morning, though, the real fear and anxiety hit and it had been escalating all morning. Around 1 a.m., Rothman had emailed her clip from the movie Pretty Woman. It was an older movie that Megan had never seen, but she had heard of it and watched the brief clip which showed the main character on a street corner trying to pick up passing motorists with her long legs, trim body, and outlandishly sexy clothes. Rothman said nothing in the text other than telling her watch it, which she did a couple of times, admiring the beautiful woman, her revealing but flattering dress, and the hot car the man who picked her up was driving.

In the morning, she was able to sleep in as their flight wasn't until noon. Her dad was gone when she got up, off to pick up Kasey and head to work, no doubt. Her mom was certainly already at work, too. She was still in only a t-shirt, eating toast when the doorbell rang. She went to the door, checking to make sure her long t-shirt covered what it needed to, and opened it to find a delivery man with a package. She signed for it, aware that he was checking out her bare legs and bare feet. She didn't mind. She thanked him and closed the door. She heard her phone ding and returned to the kitchen to check it, carrying the package. It was a message from Rothman: "Good morning, angel. Did you receive the package?"

She responded that it had just arrived. He told her to open it and to be wearing it when he arrived to pick her up. "Use the video clip for reference," he added. "Hope it almost fits."

The video clip. The outfit. She knew what was in the box. She opened it sure enough, there was a very realistic replica of Julia Roberts' dress from the movie. The top half was white, cut like a crop top with straps over the shoulders. A large gold ring connected the bottom of the white crop top to the bottom half of the dress, which was essentially a royal blue mini skirt. Her back was bare from her should blades to the top of the skirt portion of the dress. Her sides were exposed and only her navel was highlighted by the gold ring connected the top and bottom portions of the dress. The only differences were that, instead of the thigh high boots the character wore in the movie, the package contained the 6-inch black, lace-strapped heels she was wearing now. And it did not contain a blonde wig like the character wore in the movie. She didn't know what the movie character wore underneath, but naturally there was no bra for Megan and only a microscopic light blue g-string.

Megan held the dress up. She knew it would be small, but this looked really small. She looked for a size, but not was marked. She looked at the packing slip. No size was mentioned, only the words "custom-designed dress" were on the item list. Custom-designed. Rothman had this dress tailor-made. She knew he had her basic dimensions and plenty of pictures that current apps could use to custom-tailor clothing. That must have been what he had done. Now his words, "Hope it almost fits," echoed in her ears and a shiver ran down her spine.

She had already showered before she came downstairs, so she pulled off her t-shirt and put on the dress. She pulled the skirt up first. It was so tight she had to squeeze her thighs together and inch it up over her hips. Almost as short as it was tight, it extended from the top of her butt crack to just above the bottom curve of her ass cheeks. If she stood perfectly straight, there was less than an inch from her pussy mound to the bottom of the skirt. Literally every inch of her marvelous legs was on display.

Next she pulled on the crop top. It hugged tight to her body with one thin band that wrapped around her breasts. Her nipples were faintly visible through the cloth. She connected the top to the skirt with the ring and tried to walk. Even barefoot it was difficult. There was no freedom to move. She had to take baby steps to keep the skirt from riding up. It fit so tight that as soon as it got halfway up her ass cheeks, it slid the rest of the way up and snapped tightly around her waist. She had to move carefully.

She pulled the g-string on discovering that it, too, was even smaller than usual. Because it was so small, the only way to get it up on high enough on her waist was to have pull the string tightly between her puffy pussy lips and ass cheeks. All it managed to cover was the bottom third of her bald mound.

Finally, she put on the heels. It took her several minutes to figure out how to wrap the laces around her ankles and tie them. She tried walking in them and felt like a body part was going to pop out with every movement. She had never felt so exposed and limited while technically fully dressed in her life. How could she possibly go out in public like this, let alone fly on a plane and attend a high-level meeting? What had she gotten herself into?

Rothman had been delighted to see her when he picked her up. He held the car door open for her so he could watch her dress struggle to cover her as she got in. The little vixen was sex in heels and he loved the idea of showing her off all day before fucking her relentlessly all night. He knew she was uncomfortable and scared. He wouldn't hurt her, but seeing her so vulnerable was an added turn on to him. He was both her tormentor and her protector. She was embarrassed at what he was compelling her to do, yet she would stay close to him, seeking his protection, shelter, and reassurance. By submitting to him, she needed him. That was exciting to him. Her need for him would drive her desire to please him and not only make her willing to comply, but eager to perform at high levels. Mentally, emotionally and physically -- she was his toy in every sense.

The feeling of power and control was intoxicating. He had ideas for this trip that would overstep his agreement with the other members of the "school board", but they weren't here, were they? He could literally do anything he wanted with Megan and they couldn't do a thing about it. He wondered if Megan was thinking the same thing.

Indeed, Megan had realized the same thing. As they rode to the airport, she realized that the past week had only been pretending to give up control. While some moments had been extremely intense, uncomfortable, and scary, there was no real fear of significant harm coming to her. Protectors were always close by. But now, she was alone with one of them, away from all the others. And while nice, he was also a bit dark and clearly loved being in power. With no one around to keep him in check, what would he really do with her? She didn't think he was evil or bore ill will toward her, but could she be sure now? She really couldn't.

She pushed the thoughts aside as Rothman explained her outfit and the plan for the trip. He told her that if anyone asked, he was her dad and they were in a hurry to get her to an audition for play. The play was a stage version of "Pretty Woman" and Megan was up for the lead role. The timing of their flight was such that they would barely make it from the airport to the audition in time, thus explaining her unusual attire. Most people would recognize the outfit from the movie, lending credence to the story and somewhat excusing her otherwise inappropriate attire. Megan nodded her understanding of the simple but, she thought, smart cover story.

"May I ask what our schedule is, sir?" Megan asked.

Rothman ran his hand up the inside of her thigh as they drove, squeezing it lightly. "We will meet Tanaka tonight for dinner. Officially, it's not a business meeting, but understand that every meeting is a business meeting. We might talk a lot about the negotiations or not say a word about it, but make no mistake, it's all business. Tomorrow will be the official meeting and, hopefully, we will arrive at an agreement. If that's the case, tomorrow night we can relax and celebrate. If it's not the case, we will regroup and keep trying. Either way, we fly back on Friday."

"Thank you, sir," Megan said. "I appreciate you bringing me on this trip. I'm very excited to learn about negotiating."

"There are no specific plans, but I'm sure you understand that you might play a role in influencing Tanaka's decisions," Rothman said. "You might serve as a distraction, a bribe, or even a reward."

"I understand, sir," she said. She frowned, bit her lip, then said, "Um, sir, wouldn't me being a reward break the agreement you have with the other school board members?"

"Technically, yes," Rothman smiled, but his tone was very serious. "But this is business, which takes priority over the board. You'll do what I need you to do and let me worry about the rest. Understand?"

"Of course, sir," Megan said. "I'm on this trip for whatever you need me to do, sir. I'm flattered that you think I might be able to help complete a deal."

The fabricated story had helped calm Megan slightly regarding her attire. But then she saw the looks -- ogling, judgmental, laughing or disgusted -- as they walked into the airport. And now, here she was in line, trying to figure out how to take off her shoes without flashing the whole airport. She stayed close to Rothman, trying to use him as shelter. She looked up at him and said, "Will you please stand behind me while I take off my shoes?" Then, in case anyone was listening, she added. "Daddy?"

He smiled and moved behind her while she bent over, unlacing and removing her shoes as quickly as she could. He had seen the view plenty of times and would enjoy it thoroughly tonight, so he played the role of protective father, keeping his eyes up and straight ahead. He did lean and shuffle slightly to the side, however, knowing that those in line behind them were certainly seeing an ample amount of Megan's ass and likely part of her pussy. He loved showing her off.

She finally stepped out of her shoes just as they reached the security gate. The agent looked her up and down and asked about her attired. She explained it just as Rothman had instructed and the guard said, "I see. Well, that's a great movie. Good luck, young lady."

Megan breathed a sigh of relief as she grabbed her shoes and turned to sit down to put them on. To her dismay, the seats were full with other passengers putting their shoes back on too. She was prepared to wait, but Rothman spotted an opportunity.

"Come here," he said, leading her to a large planter that was part of a display in the concourse. The planter contained a big, leafy tree with some blooming flowers around it. It was lovely. He put his foot up on the edge of the planter and put on his shoes, nodding for her to do the same. The planter was about waist height. Megan didn't have to bend over, at least, but lifting her leg up so high was problematic nonetheless. Not only was her leg now accentuated as it was lifted up and bent as she reached to put on her left shoe, but the separation of her legs caused the skirt to ride up. She tried to hold it in place, but the laces required her to use both hands. Her choice was to hold the skirt and hope Rothman would tie her shoe for her -- not likely -- or simply to let her ass hang out while she put her shoes on as quickly as possible. She put her head down and chose the latter, not looking back to see who was looking or how they were responding. She blocked it out as best she could, trying to work fast while acting casual. Her mental toughness was being tested early and often. She felt like that might be the theme of the trip.

Once they got to the gate, nearly all the seats were full. The options were to sit separately, putting Megan between total strangers, or for Megan to sit on Rothman's lap. When he presented her with these options, Megan hesitated, then said, "I want to stay with you, sir, if you don't mind."

He smiled and took a seat, holding his arms and spreading his knees apart so she could step between them and sit on his lap. It was awkward, but Megan felt better being closer to him when she was so exposed.

She tried to downplay her embarrassment by loudly referring to him as "Daddy" while they talked, clearly meaning to imply that he was her dad and there was nothing odd about her sitting on his lap when there were no seats. But she knew Rothman was enjoying it. His hard cock against her hip was a clear indicator. As they sat there, he texted her, not wanting anyone to hear what he wanted to say.

"Keep calling me daddy and I'll have to fuck you right here lol," his text read. "I'm gonna have you screaming 'Yes, Daddy' and 'Harder, Daddy' all night, you little slut."

She read it and gave him a big smile, then texted back, "Yes, Daddy, I'm you're little slut all night tonight. I can feel you're ready now. I'm sorry I can't take care of you right now."

On the plane, Megan was happy to see there were only two seats on their side of the aisle. Rothman told her to sit in the aisle seat so everyone could see her better. She thanked him for the flattery while silently wishing she could have had the window seat where she would have felt somewhat normal for the duration of the flight. But she realized her feelings weren't Rothman's primary concern.

She knew he could have afforded for them to fly first class, but that would have limited her exposure. She knew he wanted her and Kasey to get used to being exposed and shown off and that she, in particular, had shown that this was one of the hardest parts about the training. So, like any good coach, he was throwing her into the fire, making her work at the things she struggled with. If she hated being exposed, then expose her even more. She understood it, but she didn't like it.

When the flight attendants served the drinks, they both put their tray tables down. Rothman then took her hand and pulled it under his tray table and between his legs. He didn't have to say anything. They both sipped their drinks casually while she stroked his cock through his pants. With all this teasing and edging, she knew Rothman would be ready to bust soon. She hoped his cock was rock hard and his load was enough to fill her belly. She still didn't love the taste of cum, but it was a turn on to drain a huge load and feel it slide into her tummy.

Rothman added to the fun by reaching under her arm and discreetly rubbing his finger across her rigid nipple. His hand was essentially blocked from view by her arm and only someone looking closely would notice his finger. And Rothman knew anyone looking closely was looking at miles of exposed leg and torso, not her arms or his finger. The captain came on the intercom and warned that their might be a little bit of turbulence ahead. Rothman pinched her nipple between his fingers, clamping down on it. When they hit the turbulence, Megan jostled around like the rest of them, but Rothman held firm to her nipple, knowing she would feel the extra pinch as the turbulence pulled her in different directions. He loved her firm breasts just the way they were, but in that moment he wished she had some big bouncy double DDs that would bust right out of that dress.

For Megan, her captured nipple was the least of her worries. She bit her lip and looked about worriedly. She had not traveled a lot and the turbulence scared her. She felt silly that the other passengers seemed to take it in stride while she acted like a scared little girl, but that's how she felt in the moment. She wanted her dad -- not her "daddy" -- here right now to hold her and protect her. Instead, she had willingly put herself in the hands and at the mercy of a man who would protect her only so far as it served his needs. Mick and Harry really cared about her, she believed. She was realizing that Rothman really didn't. He wasn't evil or cruel. But his interest in her was purely about sex and power. She hadn't realized that fully until now, and now she felt stupid for falling into the trap.

That was the thing, though. She blamed herself. Not him. He wasn't bad or evil. It was her fault, not his. She had made a commitment to serve him, to learn from him, and to take care of his needs and follow his commands. She still had so much to learn. This trip promised to be very educational. She turned the focus from her fear and distrust and reminded herself that she had chosen this. She wanted it. It was like she had gotten on the roller coaster and was at the top of the first hill. No matter how much she wanted to get off the ride, it was too late. She was all in. So the choice was worry and cry or throw her hands up and have fun. Overcoming your fears could be freeing and exhilarating. She had embraced that concept when she first seduced Mick and Harry. It was time to embrace it again today.