The Major Diaries Pt. 16

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 16 looks at Jon & Stephanie as they plan a trip. All characters are adults over the age of 18.

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Stephanie felt excited when she woke up. Jon was going to take her shopping. He was planning to take her to a beach resort, and he wanted her to have new clothes for their first trip together. He'd shown her photographs of the luxury resort on a beautiful island in the Caribbean, and it looked wonderful. The fact that she'd be there with the man she loved made it even more exciting.

It was something Jon had wanted to do with Stephanie since shortly after they began seeing each other. She didn't know this, but Jon had taken one of his college girlfriends on a four-day weekend trip to a resort on the west coast of Mexico. They had sex, went sightseeing, had sex, went to the beach, had sex, went dancing, had sex, dined at fine restaurants, and in their spare time they had sex. Considering the fact that they didn't even love each other, they had a marvelous time.

Jon had considered taking Stephanie to the very same resort, but he wanted to avoid the possibility that she'd discover he'd been there with another woman first. He wanted her to feel special. So Jon did a bit of research and found an even more luxurious resort in a location that was even more beautiful. It was a longer airplane ride, but he knew Stephanie had never flown before. He imagined that treating her to a first-class ticket would be as entertaining as playing in the surf.

Normally, Stephanie shopped at discount stores. She was particularly fond of Target, which had a nice selection of clothes for women her age. Her mother earned a good income, so she and Stephanie were comfortable, but designer clothes and accessories were not something they could afford. Jon could afford to buy Stephanie the finest clothes available, and that's what he intended to do.

Their first stop was to a high-end store that specializes in designer fashions. Stephanie realized immediately that she'd never been inside a store like this.

"Who told you about this place?" Stephanie asked.

"My mother," Jon said.

"How does a woman who lives in Chicago know about stores in San Francisco?"

Jon smiled. "She has ways," he said. "If shopping was an Olympic event, my mom would have the gold, silver, and bronze."

He had a long list of items he wanted to buy that day, so he immediately asked a clerk for help. The clerk was a young, handsome woman wearing a designer suit that probably cost more than someone could buy with an entire week's wages for a typical retail clerk. Clearly, this was not a typical store.

The changing rooms weren't typical, either. The changing booth opened into a larger private area with comfortable seating so that people like Jon could relax as their companions modeled selections. Jon described what they wanted, and the clerk shuttled back and forth from the shopping floor to the changing room. When Stephanie shopped, she usually tried to avoid interacting with the clerks. Jon seemed very comfortable telling the clerk what he wanted.

And the clerk was very good, giving Stephanie a seemingly endless supply of beautiful options. She tried on slinky evening gowns for dining and dancing. Loose, colorful dresses for sightseeing. Casual wear. And, of course, swimsuits.

They were unlike any kind of swimsuits Stephanie had ever considered wearing in the past.

"Jon, I can't wear this!" Stephanie said when she looked in the mirror. Jon told the clerk they were going to a resort popular with tourists from Europe and other international locations, so the clerk gave Stephanie the kind of sexy, revealing outfits such people wore. But Stephane had never worn anything like that in the past, and as she looked at her reflection she couldn't imagine wearing it now.

The brightly colored suit featured small triangles of cloth that covered very little in the front, and even less in the back. Jon said he liked the first suit she tried on, and he liked the second, but when he said he liked the third, Stephanie couldn't believe it.

"Jon! Look at this!" she said, turning so he saw her back. It was a string bikini, and her butt was completely exposed. There were just thin black straps that held the fabric in front in place. "I'm almost naked! I can't believe anybody wears stuff like this!"

The clerk saw that her input was needed. "Outside America, suits like this are very common. Older women wear more modest attire, but women your age favor the more revealing styles. In many places women bathe topless, or fully nude. I imagine that suits like the ones you've tried so far will be common where you are going."

"Steph, my family has done a lot of traveling," Jon said. "I'm sure these suits are fine."

She looked unconvinced. "Let's make a deal," Jon said. "Let's buy a more conservative suit that we know you'll like. Something less revealing. But I want you to make me a promise. When we go to the beach I want you to look at the way other young women are dressed. Then, promise me you'll dress the same. Steph, you are a beautiful woman. You shouldn't be all covered up like an old lady."

"Fine. That's reasonable," she said.

Jon smiled to himself. The resort had a nude beach, and Jon was sure that virtually all the young women would wear nothing at all. He'd just made Stephanie promise to dress like the other girls, which meant she'd have to get naked for him. This wasn't a particularly original idea for Jon. He'd done the very same thing with the college girl he'd taken to the resort in Mexico. She'd been shocked when they went to the beach and she saw everyone was naked.

It took a few minutes for Jon to coax her out of her clothes, but the girl eventually loved being naked in the sun, surf, and wind. She'd been aroused by appearing nude in public for the first time in her life, and they had particularly energetic sex afterward when they got back to their suite. Jon expected Stephanie would have the very same reaction, and he looked forward to seeing it.

The shopping continued with shoes, as they selected everything from beach sandals to towering stilettos. They purchased hats, sunglasses, an oversized handbag big enough to hold beach towels, and that was when Stephanie got tired of shopping. Jon had wanted to buy some sexy lingerie, but that purchase would have to wait for next time. Maybe that was something they could shop for at the resort.

Stephanie was repeatedly distressed by the prices. She found it challenging to justify paying so much for clothes. "Steph, stop. Just stop. Stop looking at the price tags. My mother wears clothes that cost 10 times as much as this. This is going to be a nice trip, and I want you to have nice clothes. Just stop thinking about it." Stephanie tried, but it wasn't easy.

They had so many packages that one of the clerks helped them carry them all to Jon's SUV. Stephanie had wondered why Jon didn't drive his little two-seater sports car, but she realized that he knew he'd buy her more stuff than would fit in that car's small trunk.

It took two trips to carry it all up to Jon's apartment, where they carefully unboxed each item and hung it in Jon's closet. Stephanie felt overwhelmed. It was almost painful to watch so much money go toward buying clothes that were very nice, but much nicer than necessary. Stephanie thought they could have shopped at Target and done just fine. She mentioned that to Jon, who just laughed.

"I can tell that I'm going to have to put a lot more effort into pampering you," he said.

"You're doing plenty," she said.

"Agree to disagree," Jon said.

Jon went to his stereo and put on his recording of ocean surf. It was one of their favorite choices for a background soundtrack for sex, and it seemed like a particularly good thing to listen to as they prepared for a beach vacation. Without a word, he began removing Stephanie's clothes. As he often did, he got her completely naked before he removed a single item of his own clothing. Neither one of them understood why it felt so erotic for Stephanie to be naked while Jon was fully clothed, but that's how it was.

Stephanie laid down on the bed and watched as Jon disrobed. His cock was fully erect by the time he removed his boxers. The erection pressed into her thigh when Jon laid down next to Stephanie and began kissing her passionately. She couldn't help imagining how good that cock would feel when it was inside her, but Jon decided he didn't want that to happen immediately.

What Jon wanted to do was kiss his way down Stephanie's body until he slipped between her legs, where he intended to go down on her until she came at least once. He got a pillow and placed it under her bottom. Stephanie knew Jon usually did this when he wanted to go down on her for an extra long time; it raised her pussy up a few inches so Jon didn't need to strain his neck as he licked and sucked her sensitive flesh.

He began by nibbling on the tender flesh of her inner thighs, moving closer and closer to her overheated pussy. Like many women, a lot of what Stephanie knew about sex came from reading women's magazines, which carried a lot of very explicit articles about the way men and women pleased each other. She knew that one of the most common complaints women had about men was that so many of them were so reluctant to go down on them.

Some expected women to give them blowjobs, but they wouldn't return the favor. Others rushed, as though they were doing an unpleasant task they wanted to finish as soon as possible. Others had no idea how to lick, suck and nibble in ways their women enjoyed. Stephanie didn't quite understand how a man could do such a simple job so badly, but that was because it was Jon who spent so much time between her legs. She thought that the reason she enjoyed it was that Jon had an enthusiasm that sometimes overwhelmed her. He never seemed to tire of the task. He let her know that he loved the way she tasted, and that her feminine fragrance was intoxicating. The way Jon acted when his face was pressed up against her convinced Stephanie that every word he said had to be true.

Stephanie felt her arousal build, knowing it wouldn't be long before her climax began. She listened to the recorded sounds of waves crashing ashore and imagined that nothing could be more pleasant than what she was experiencing at that exact moment. Once again, she reminded herself that Jon was such a wonderful lover that she needed to do anything she could to be just as good for him. Her magazines made it clear that men and women often struggled to find agreement about sex. Some women complained, quibbled, and resisted doing the things their men wanted. Stephanie vowed to never be like that. She would do whatever he wanted, without ever showing any kind of resistance. He'd asked her to do some edgy things in the past. Things like bondage, and facials, but she'd never objected, and she always grew to enjoy the things she was skeptical about in the beginning.

That's what she was thinking as she began having her orgasm. Jon could tell she was beginning to cum, so he picked that exact moment to remove a wet finger from inside her pussy and slide it gently up her ass. It was startling and unexpected, and her first thought was that she didn't like it. But then she began to have a climax so powerful it overwhelmed her, and she knew it happened that way because of the surprise Jon produced at the end.

Wave after wave of pleasure flowed outward from her pussy and her ass. She felt the strong muscles of her rectum clench powerfully on Jon's finger as her pussy throbbed in unison. "Oh, Jon . . ." she moaned, feeling almost delirious with lust. Once again, she thought that Jon could have whatever he wanted, whenever he wanted. It was the way she wanted to be for him. It was what he deserved.

She was coming down from a joyous plateau as Jon removed the pillows from under her bottom and climbed up her body. He put the head of his cock at the entrance to her pussy, then pushed inside. It sent a jolt of pleasure through her body. Jon was so excited after spending so much time eating her pussy that he was afraid he might climax too quickly. He rested a moment, leaving the head of his cock motionless in her pussy. They both wanted him to begin moving in and out, but he resisted that temptation so he could calm his feverish mind.

Stephanie was getting a bit impatient when Jon finally pressed inside her a tiny bit more, then slowly withdrawing again. He paused - again - and she tilted her hips upward to try to encourage him to give her more. He gave her more, but not much, pressing into her slightly, then backing out again, then pressing in a slight amount deeper. It was simultaneously delicious and maddening. He was teasing her. She'd had more than enough foreplay. She wanted to be ravaged like he'd ravaged her so many times before.

"Please," she said. She knew Jon liked to hear that word. In the past, he'd refused to proceed until she'd begged him to continue. Something about the word "please" aroused Jon in ways unlike anything else. He loved Stephanie, respected her, and considered himself to be her equal in every important way. Still, hearing her submit to him was endlessly satisfying. He had a deep need to hear her acknowledge his dominance this way. Neither one of them knew why this was so, but they both liked the way it felt.

Stephanie squirmed sensuously beneath Jon's body as he went deeper and deeper inside her. She made sexy noises that let him know how much she was enjoying what he was doing. In the time they'd been together, Jon and Stephanie had learned exactly what it took to give pleasure to each other. They'd mastered the art of physical romance. By the time Jon's cock was sliding all the way into her pussy, Stephanie was approaching another orgasm.

When he looked at her face, Jon saw that Stephanie's eyes were closed and her mouth was open as she tried to catch her breath. She looked deliriously happy as she approached the edge. They both wanted this to last forever. Jon moved with deliberate slowness because he wanted to last, but he knew he couldn't last much longer.

It gradually became obvious that Jon would have to climax before Stephanie. He couldn't hold back long enough to make her cum first. He knew that there was one thing he could do that was guaranteed to make her cum as soon as he did.

Jon withdrew from Stephanie's pussy, took his cock in his hand, guided it to her tiny brown butthole, and shoved the head inside. "Ohhhh!" she said, startled by this sudden change in tactic. She'd been cruising gently toward an orgasm, and had no idea Jon couldn't continue long enough to let that happen.

Instead he began moving and out of her ass, moving roughly so he could get as deep as possible before losing control and cumming inside her. She felt him shove his cock deeper and deeper up her ass. It was so sudden. It seemed to Stephanie that Jon was so aroused he was losing control of himself. That was simultaneously exciting and frightening. He was acting like an animal - but in a good way.

Jon was buried almost all the way inside her ass when his orgasm began. The sensation was so intense it was a bit painful, as her tight little ass had to stretch to accommodate his erection. That little bit of pain made everything more exciting somehow, and Stephanie's orgasm began. He slammed into her body one last time before he came, and came, and came. Stephanie reacted immediately, hugging him closer as she felt her own climax begin roaring through her pussy and ass. They ground their bodies together lewdly, and Jon called out with relief. Staphanie cried out all the time, but it was rare for Jon. She smiled to herself as she listened to this evidence that her man was having a good time.

The sound of the surf grew quieter as the recording played out. It reminded them both of their plans to take their first trip together, visiting a tropical paradise where they could frolic in the ocean, and do so much more. When Jon finally opened his eyes, he saw Stephanie looking up at him with love.

It would be the best summer of their lives.

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Things are going well so far. Chapter 17 describes what happened at the resort.