The Major Diaries Pt. 17

Jon Major has always enjoyed the company of women. In the series Caught! we saw Jon as a college student whose heart was broken repeatedly by girlfriends who were unfaithful. The Major Diaries tells the story of Jon when he's older and wiser - and determined to be with as many beautiful women as possible without risking betrayal. How well does he succeed? Chapter 17 explains the clever process Jon uses to draw young women to his bed. All characters are adults over the age of 18. The Major Dairies Pt 17

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It was mid-afternoon when the jet took off, leaving San Francisco behind. Stephanie thought they should have a meal before leaving, but Jon encouraged her to be hungry when they got on the plane. He knew that first-class passengers always had more than enough to eat and drink, and he knew that enjoying cocktails and food would make the long flight pass faster. Because they were heading east, it would be early evening before they reached their Caribbean destination.

"What do you want to do first?" he asked.

"I don't know. Will it be too late to swim?"

"It's not a good idea to swim in the ocean after sunset. That's when the predators start looking for supper. But we can swim in the pool. The resort has a fabulous pool, and it probably won't be very crowded that late."

"I think I'd like to do that, Your Majesty," she said.

"Then it shall be done, wench," he said.

Stephanie felt wonderful for many reasons, but one of them was that she was half finished with the cocktail she'd been served immediately after take-off. Stephanie wasn't old enough to drink legally, but no one ever asked to see her ID as long if she was with Jon. She was beginning to learn that rich people don't have to follow the rules average people follow. She tried to dress in ways that made her look older, and she did her hair and makeup that way too. Still, it was just plain weird that she was regularly carded when she wasn't with Jon, and she was never carded with him. She realized that the airline considered first-class passengers to be more important because they paid so much more for tickets. They weren't going to do anything to annoy their best customers.

"I suppose we could get dinner after we land," she said.

"I don't think so," Jon said. "We can if you want, but I'm pretty sure our tummies are going to be full by the time we get to the airport."

"Well, we can always do what we always do," she said.

Jon laughed. What a clever way to talk about sex. He laughed a bit more than he would have if his cocktail hadn't been taking effect.

They had a colorful pamphlet that described the resort where they planned to spend the next seven days. There were clubs, shops, restaurants, a beautiful beach, an enormous pool, a gigantic health club. There were classes on everything from yoga to an introduction to the Kama Sutra. There were pictures that made it clear couples who took the Kama Sutra class were fully clothed. The photos all showed images of young, joyful people, but Jon told her to expect a mix of young and old. Most of the people who could afford a resort like this were younger than them, although Jon expected to encounter plenty of "trust fund babies" using inherited money to jet around the globe from one fun place to another.

In most ways, Jon was a trust fund baby himself, growing wealthier every year as he received his grandfather's inheritance in annual installments. But Jon did more than play. He'd always been studious, and he had no intention of spending his life on one endless vacation. There was a reason that a man who would never need to earn a living felt the need to get a master's degree in French language, literature and history. He saw entertainment and recreation as compelling side dishes, not as entrees.

Stephanie looked out the window, enjoying her first experience seeing earth from 30,000 feet. Despite traveling at 650 miles an hour, the landscape passed below them at a crawl. Large cities looked small. Vast farms appeared as small squares arranged like the patchwork of a crazy quilt. Corn. Soybeans. Wheat.

The flight attendant spent a lot of time keeping their glasses filled and serving them one tasty treat after another. Stephanie was surprised to learn that she could enjoy poached salmon prepared in an airline kitchen. The endless parade of cocktails was less of a surprise, but just as delightful. She and Jon enjoyed the hours of time for casual, unhurried conversation.

When it came time to rest, Jon spread a blanket across their laps and let Stephanie rest her head on his shoulder. She was just beginning to relax when she felt his hand reach up her skirt.

"Jon! What are you doing!?" she asked.

Jon smiled and said nothing. It was obvious what he was doing. His hand went farther and farther up her skirt, stroking her inner thighs as he got closer and closer to the pair of panties that covered her pussy. What, exactly, did he expect to accomplish? It soon became clear what he expected. He expected to play with her, right there, sitting in the first class section of a crowded airplane.

Everything in Stephanie's mind made her want to tell him to stop. This was going too far. Couldn't he wait until they got to the big comfortable bed in their suite? Hadn't they had sex just before leaving for the airport? Did Jon ever feel he'd had enough?

If so, he didn't feel that way now. He just kept smiling as he looked at Stephanie and moved closer to his goal. She didn't say no because she never said no. Over and over, Stephanie had decided that she would be the kind of girlfriend who would never refuse Jon anything. She would never say no, never complain, never question any of his desires. It was all part of her effort to be the sexiest woman Jon had ever known. He was a great boyfriend, he could always find a woman willing to do whatever he wanted, so it was Stephanie's goal to be that kind of woman for him.

That meant she needed to let him proceed, so she spread her knees as far as they would go and prepared herself for Jon's touch. She was very wet by the time she felt him. He worked one finger past the edge of her panties, then began running that finger up and down her fevered pink inner flesh. She looked around the cabin to see if anyone was watching them. The blanket seemed to conceal everything, but the whole experience was nerve wracking because of the fear of being seen, of getting caught. Stephanie realized that the flight crew couldn't toss them out of the jet at 30,000 feet, but being caught would be so deeply humiliating that she hated to even imagine it.

Jon didn't mind at all. He occupied the aisle seat, so he would see anyone approaching. The big first class seats provided plenty of room for what they were doing, the blanket covered everything, and he thought this was a wonderful opportunity for them to experience something completely new.

"Take off your panties and give them to me," he whispered.

Oh. My. God. Only Jon could make a request like that. She lifted her bottom off the seat, hiked up her skirt, and eased the panties down past her knees and off her feet. She gave them to Jon, who slipped them into one of his coat pockets. Then he went back to work, running his fingers up and down the hot wet slit that was no longer covered by a thin layer of fabric. It made Stephanie very nervous, but she couldn't help being aroused by all this kinky stimulation. She began gasping for breath, trying to be as quiet as possible so they didn't get caught.

Jon slipped a finger inside her as he massaged her clit with his thumb. He slipped a second finger inside her. The onslaught overwhelmed her and made her increasingly nervous. This took Stephanie far outside her comfort zone, but she was determined not to make Jon stop.

It was at about this point that Stephanie realized that Jon would not quit until he made her have an orgasm. She was so frantic with nerves she didn't think an orgasm was even possible, but she knew he would continue as long as it took to make that happen. There was only one thing to do. Stephanie had to find the ability to relax enough to let her climax happen. She often called out loudly when she came, and she knew she had to keep silent, but there was no alternative to letting Jon make her cum.

So that's what she did. She closed her eyes, leaned on his shoulder, and tried to focus on the waves of arousal between her legs. It wouldn't take long if she could just relax enough to give him what he wanted. Jon consistently demonstrated a desire to get Stephanie to experience new and exciting sexual scenarios. He never asked permission, and she never considered denying him anything.

It took some time for her arousal to grow. This wasn't a very erotic situation. But she managed to do what he wanted, and in time she was moving her hips up and down so he had better access to her most sensitive areas. She realized that there was nothing to stop Jon if he wanted to finger her ass, but she hoped he didn't. It would be very hard to keep quiet if that happened. Fortunately, Jon focused all his energy on her pussy, especially her sensitive little clit.

He was relentless. His fingers moved in and out as he drove her closer and closer to the edge. He'd massage her clit, stop for a few seconds, then go right back to work. Stephanie struggled to keep quiet. If this had been happening in the privacy of Jon's bedroom, she would be making all kinds of sexy sounds. That seemed like a very bad idea on an airplane.

It went on, and on, and at length she had no choice but to cum. It wasn't the most powerful orgasm she'd ever had, but it was the strongest she had at 30,000 feet. Stephanie bit her lower lip as her climax rolled on and on. Once again, Jon demonstrated that he knew just how to drive Stephanie crazy, even when she wasn't convinced it was a good idea.

Jon removed his hand and Stephanie took a deep breath. That was different, she thought to herself. I wonder what else Jon's going to think up this week. She looked over just in time to see Jon putting his fingers in his mouth one at a time and sucking them clean. Of course, she thought. That's exactly what I'd expect Jon to do.

A flight attendant picked that moment to make an appearance. "Can I get either one of you another cocktail?" he asked.

"I believe I'm ready for a double," Stephanie said.

She was sipping her drink as she remembered that Jon still had her panties. After she finished her cocktail, she'd ask him to return them so she could put them back on in the ladies room. She assumed he wouldn't ask her to remove them again before the airplane landed, but there was no guarantee. All she knew for sure was that she'd feel more comfortable if her wet pussy was wrapped in a nice dry pair of panties.

Stephanie reflected on the fact that people who had sex in airplanes had a tradition of referring to themselves as members of the Mile High Club. She wasn't sure if what had just happened qualified her as a member. Then she remembered that it didn't matter. Jon had a pilot's license, and had been flying his family's private airplane since he was 16 years old. Inevitably, he would eventually take her up in the air, turn on the autopilot, and make her a full member in the exclusive club. It didn't matter if she was a member yet; she'd belong eventually.

Jon was sipping on his bourbon when Stephanie spoke up.

"I know what we should do first after we land," she said.

"What's that, Steph?" he asked.

"We should find a hospital."

Jon looked concerned. "A hospital? Why? What's wrong?"

She took another long pull on her drink. "We need to check you into a psych ward," she said. "You. Are. Insane."

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This trip is starting well, isn't it? See how it continues in Chapter 18.