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 1I explains what its like for Stephanie to be pursued by two very different men. All characters are adults over the age of 18.
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Stephanie continued to tell Jon about her dates with Denny, reporting their outing to the school play, the hike, and a particularly nice party sponsored by parents of the soccer girls. She told Jon that she felt a bit of jealousy coming from her teammates; Stephanie was the star of the soccer team, she’d become one of the most popular and glamorous students, and she was dating the tall, handsome Denny, who was arguably the best male athlete at their school.
It was understandable; young people are quick to feel sorry for themselves when they see others who have things they wish they had. It seemed as though Stephanie had everything a high school girl could want.
If only they knew the truth. The best thing Stephanie had was Jon, who was a secret to everyone in her life. Her friends would be shocked to learn that on most afternoons, and on Saturdays after the soccer games, Stephanie was going to the apartment of an older man and enjoying a torrid love affair.
She told Jon nothing about the physical side of her relationship with Denny, and he was careful not to ask, but Stephanie was beginning to feel a bit smug about having two men who made her feel sexy and desirable. She liked to compare the way they were different, with Jon being an extraordinarily accomplished lover who aroused her more than she’d thought possible, and Denny being a sweet boy who didn’t know much about romance, but who was anxious to learn. Both men made her feel special, but they did it in different ways.
One afternoon, after Jon made Stephanie cum three times, she was feeling so much love for him that she decided to ask a question.
“Jon, what can I do to make you feel good? I mean, good in bed,” she said.
Jon smiled. “You’re doing an exceptional job of that already. Just keep doing what you’re doing.”
“That’s not what I mean,” she said. “When we make love, it’s almost always up to you to decide what we do and how we do it. You always make me feel wonderful. I don’t think I’m putting in as much effort as you are. I want to please you the way you please me.”
Jon knew what she meant. “Steph, I’m kind of an old-fashioned guy when it comes to sex,” he said. “I think it’s like dancing. The man leads and the woman follows. I enjoy it when you do things to me – and what you’re doing is wonderful – but what I enjoy most is giving you pleasure. I just made you cum three times. Watching you, holding you, feeling you as you cum – that’s what I like most.”
Stephanie felt a bit frustrated. “I just think that if I was a more experienced lover, I’d be doing more to excite you,” she said.
“Hmmm. Let me think about that,” Jon said.
Later, Jon had an idea. He ordered a book online, and gave it to Stephanie after it was delivered. “This is a book of short erotic stories written by women for other women,” he said. “Why don’t you read some of them? You might be interested in finding out more about the sex fantasies of women who are older and more experienced than us. If you find something you’d like for us to do, we could try that and see how it works.”
Jon also suggested that they might enjoy using some sex toys. “I’d love to take you shopping at a sex store downtown, but we can’t risk being seen together,” he said. “Maybe we could look at some stuff online and see if there’s anything we’d like to try.”
A few days later Stephanie said one of the erotic stories seemed particularly exciting to her. It told the tale of a sexy female slave whose job was to satisfy the needs of a king. He had a queen who did her duty and provided heirs to the throne, but she had no actual interest in sex, and didn’t want to indulge the king’s desires. Therefore, the king bought the most desirable slave he could find, and subjected her to increasingly wild, kinky practices she’d never known about before. The slave grew to love the king, and she wanted to satisfy him the best she could.
It wasn’t great literature, but Stephanie thought it was very hot. She thought it would be fun to imagine she was a sex slave and Jon was her king.
Jon read the story and saw what appealed to Stephanie. If she wanted to enact this fantasy, he was happy to do it. It seemed like a fun way to spice up their sex lives. In truth, Jon thought their sex lives were already very spicy, but this was just more evidence of the fact that he was in love with a woman with unusually powerful erotic urges. They went online and ordered some very kinky women’s lingerie that seemed to go well Side Escort with the fantasy of the king and his slave, and the time finally came for them to make the dream real.
“Good afternoon, your Highness,” Stephanie said to Jon. “I’m so glad you decided to visit my chamber.”
“I can never stay away long, dear girl,” Jon said. “I think about you constantly. I am never happier than when I am in your bed.”
“Your Majesty is too kind,” Stephanie said. “I seek only to serve you.”
“And you serve me very well,” Jon said. “The Queen is a good woman who has given me two fine boys and a beautiful daughter, so I have nothing bad to say about her. But she lacks the passion you possess in such abundance. Whether I am meeting with the aristocracy or fighting on the battlefield, my thoughts return to you always.”
“What pleasures do you seek today, My Lord,” Stephanie said. “Would you like to have me pleasure you in the French way?”
French way? That sounded interesting. “That would be most satisfactory,” Jon said.
Stephanie pulled down Jon’s pants and began giving him a particularly satisfactory blowjob. She understood that the fantasy would be most enjoyable if she did her best to pretend she really was a royal sex slave, and that Jon really was her king. That meant that the cock in her mouth was the royal cock, and it deserved royal treatment.
Jon stroked Stephanie’s hair as she bobbed up and down. She seemed to enjoy this little game as much as he did. Being with Stephanie always made him feel like a king; making that an explicit part of a role playing game felt very natural to him. Stephanie had always had an aptitude for submissive sex; acting like a sex slave was a natural role for her.
King Jon didn’t really know where this was going; in the erotic story where Stephanie got this idea, the female slave always decided what she and the king did in bed, even though it was understood that the king was her ruler in all other ways. Jon just laid back and enjoyed what she was doing, which was exquisitely pleasurable.
He didn’t know that Stephanie had prepared a surprise.
When Stephanie decided she wanted to have a more active role in finding ways to give Jon pleasure, she began serious study of the subject. She spent a lot of time reading her book of erotica, but she always liked to go online, where there were endless sites that offered advice on how to arouse a man. She’d found a particularly interesting idea she planned to pursue today.
While Jon wasn’t looking, Stephanie applied lube to two of her fingers, then gently pushed them into Jon’s ass. He was shocked, of course. This was not normal behavior for his sweet, innocent Stephanie. As soon as her fingers were all the way inside Jon’s body, Stephanie began searching for his prostate gland. She’d studied diagrams that showed its location, and she’d read that it felt like a little wrinkled ball about the size of a walnut, so it didn’t take long for her to find her target.
She began gently massaging Jon’s prostate. Jon went rigid as the sensation exploded from that part of his body.
“Is this the right spot, My Lord?” she asked.
“Uhhh . . . ohhh . . . yes. Yes yes yes,” Jon said.
“I am so glad, Highness,” she said. “Just relax and let me take care of everything.”
Stephanie had read that most men loved it when someone milked their prostate glands like this, so she focused on the task as she continued to suck Jon’s cock. It was so pleasurable that Jon found it impossible to continue to think about their role playing. It was amazing that Stephanie was doing this to him.
When she’d tried to imagine what a sex slave would do for her king, she tried to imagine being a high-class whore with deep experience pleasing men. Milking their prostate seemed like something men would expect from an expensive whore. As a sex slave, Stephanie liked to imagine herself as the most expensive whore in an entire kingdom. It felt dirty in the most delicious way imaginable.
Stephanie may have been new at prostate massage, but by this time she was an accomplished cocksucker. She’d discovered the kinds of stimulation Jon liked most, so she focused on using her lips and tongue just right as she sucked and bobbed her head. She regularly made eye contact with Jon, smiling as much as she could smile with his cock between her lips.
She hoped he’d have a great orgasm, and her hopes were realized. When Jon began to climax, his cock throbbed over and over as he came and came and came. Stephanie sucked every drop down her throat. She could tell that he came a lot more than usual; his big load felt good sitting in her tummy. Jon groaned loudly as the throbbing continued.
“I hope your Majesty was well pleased,” Stephanie said afterward.
“Wench, you are a wonder. That was incredible. Where did you learn to do that?” Jon asked.
“In France,” Stephanie said.
“Vive la France,” Jon said. “C’est magnifique.”
This wasn’t the first blowjob he’d gotten from Stephanie; it was simply Side Escort Bayan the best. Ordinarily, Jon would return the favor by eating her pussy long enough for his erection to return so they could have regular sex. But he was so exhausted – so drained – that he could do nothing but lay on his back and try to catch his breath. Stephanie didn’t care. Her agenda that day was to take charge and give Jon something wonderful and unique, and it was clear that she’d done exactly what she set out to do. She wore a little smile as she listened to Jon gasping for air as he recovered.
He pulled her to him and held her in his arms. “Where did you learn to do that?” he asked.
“I told you already. In France.”
“No, seriously. That was new.”
“I read about it online. It seemed like something you’d enjoy.”
“Gee. Ya think?”
Jon eventually recovered enough to get a second erection, which he used to thank Stephanie for what she’d done. They were both satisfied by the time they were finished. As Stephanie walked home that afternoon, she felt a wonderful sense of achievement. She felt like some kind of sex goddess in love with a sex god. For years, she’d known that many of her friends engaged in sex with their high school boyfriends, and she’d known that some of them had experience with hot, kinky practices. But she was sure that none of them could possibly have a man as passionate as Jon Major. None of them could have experienced anything like the fantasy of a sex slave and her beloved King. None of them could have done anything like what she’d done that day to Jon.
And to make everything even more amazing, she had a completely different relationship with her high school friend Denny, who had no way of knowing that Stephanie was preparing to do something very special for him.
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Denny was about to have his 19th birthday, and Stephanie told him she wanted to give him a present. “You don’t need to do that, Steph,” he said. “Going out with you is better than any present.”
“You’re sweet,” Stephanie said. “But I want to give it to you anyway.”
It was a Sunday afternoon. They’d gotten together earlier and gone to their school’s workout facility to lift weights. As two of their school’s top athletes, it was something they had to do anyway, and it was more fun if they did it together. Stephanie said she wanted to give Denny his present after their workout, and she said she had his gift at home.
Stephanie left Denny sitting in her living room while she went to her bedroom and stripped off all her clothes. Her plan was to greet Denny naked. She’d considered changing into lingerie or a sexy bra and panty set, but she decided naked was best. Denny would never forget what was about to happen. If the first thing he saw was Stephanie’s nude body, it would be the most memorable thing she could show him.
“I’ve got your gift here, Denny,” she said.
Denny looked up and saw the most beautiful thing he’d ever seen. Stephanie was a goddess. She watched his face to see his reaction, and she was pleased to see the look of shock and wonder, followed by an expression of pure desire. Denny would never forget the image being burned into his brain at that moment. No boy ever had a more enticing sign that he was about to lose his virginity. Stephanie had enjoyed being admired by Jon for so many hours that she had a healthy confidence in the appearance of her body, and she enjoyed seeing that same admiration in Denny’s face.
“Let’s go,” she said, walking over to Denny, taking his hand, and leading him to the bedroom. His hand was trembling, which Stephanie thought was both cute and amusing. She felt good to be doing something so nice for Denny. He’d been a good boyfriend, he was a nice person, and she wanted to give him something to express her fondness for him.
But Denny had no idea how to proceed. He was so startled and aroused by the sight of the naked beauty before him that he was virtually paralyzed. Stephanie unbuttoned his shirt, undid his belt, unzipped his pants, then got down on her knees and lowered his pants and boxer shorts to his ankles.
When she got her first good look at Denny’s erect cock, she thought it looked exactly like Jon’s. Both Denny and Jon were circumcised, and there wasn’t much difference in the length or width of their cocks. She imagined that Denny would feel good inside her, but she doubted that his skills making love could be nearly comparable to Jon’s. Jon was an accomplished lover, Denny was a shy virgin, so it would be up to Stephanie to make this encounter as good as possible.
She started by getting a condom from a drawer in her bedside table. “You’ve got to wear this,” she said, ripping over the foil package and unrolling the condom on his hard penis. She knew that protection wasn’t really necessary. She had an IUD, Denny’s virginity guaranteed he had no STDs, and she knew she hadn’t caught any infections from Jon.
But if she told Denny he didn’t need a condom because Escort Side she was on birth control, he would realize she must be having sex with someone else. That was a topic Stephanie wanted to avoid. Besides, she felt she had to teach Denny to be responsible about sex. His next girlfriend would appreciate it if Denny used condoms without being asked.
Stephanie laid Denny on the bed, then laid down beside him. She took his hand and placed it on top of her pussy. This was a nice experience, but it hadn’t aroused her much, so she needed foreplay before they could continue. And Denny needed to be taught that women always needed foreplay, so Stephanie would make sure he gave it to her.
“Ummmmm . . . that feels nice,” she said as Denny’s trembling hand began tentatively massaging her pussy. It did feel nice, but it wasn’t enough. Gradually, Denny became more confident, and his touch became firmer and more exciting. That was one thing Stephanie loved about Denny – he had such big, strong hands. It was the one thing he had that compared favorably to Jon, who gently caressed her body in ways that were wonderful, but in a completely different manner.
Stephanie wasn’t sure if she should touch Denny’s cock or not. She always spent a lot of time playing with Jon, but she knew that Denny was probably so overwhelmed by what was happening that he’d surely climax much too soon. She decided to avoid touching him. That was something she could save for the next time they had sex – and she’d already decided they’d have sex regularly in the future.
It wasn’t too long before Stephanie was wet, aroused, and ready. Denny had no idea how much foreplay he needed to give her, so it was up to Stephanie to tell him. “I’m ready,” she said. “Make love to me, Denny.”
This was it. Denny could barely believe that he was about to have sex with a girl he loved, who happened to be the most beautiful and desirable girl he’d known in his life. He thought of her as being like a model, or a beautiful actress – like one of the gorgeous women he saw on TV or in magazines. She was not like any of the other girls at their high school. She was more desirable than all the others combined.
He laid down on top of Stephanie, who took his cock in hand and guided it to the entrance to her pussy, making sure he knew where to put it. Then she spread her legs a little wider, and she waited for Denny to slide inside. He was a bit awkward about it, but after a few seconds the head of his cock popped into Stephanie’s body. She wanted to reassure him, so she let out a little moan of pleasure to let him know he was doing the right thing.
Denny’s natural instincts finally took over, and he began to move in and out. It wasn’t long before he got so excited that he began moving too fast. Stephanie had expected this. “Go slow, Denny,” she whispered. Denny tried – he really tried – but every cell in his body wanted to slam in and out of Stephanie as fast as a jackrabbit. I knew this would happen, Stephanie thought. I’ll just have to deal with it later.
In short order, Denny began to cum. Stephanie wrapped her arms around his big, muscular back as she felt his cock throb over and over and over. What Denny did to her felt OK, but it wasn’t nearly enough. She hadn’t come close to having an orgasm herself. When Denny was completely finished, Stephanie made sure he pulled out before he got soft and there was a chance he’d slip out of the condom and accidently spill his cum on her pussy.
“I’m sorry,” Denny said.
“Don’t be sorry. That was wonderful,” Stephanie said. And she was telling the truth. It HAD been wonderful – for Denny. And she felt wonderful for giving him such a marvelous birthday gift.
Denny began to act as though he was going to get out of bed, but Stephanie held on to him. “Stay here. Hold me. I want to hold you,” she said. She began running her hands up and down Denny’s body, and she placed one of his hands on her butt. It was a part of her body he hadn’t explored much; now was a good time to start.
One thing Stephanie had learned from Jon was that if she just waited a few minutes, she could expect her man to get hard a second time, and the second erection would last much longer than the first. Jon had made this a regular part of their lovemaking, but Denny wasn’t knowledgeable enough to realize that lots of men who climax too quickly can usually satisfy their women by waiting to get hard again.
Stephanie waited a few minutes, then began stroking Denny’s cock in the way she knew Jon enjoyed most. She suspected that Denny would prefer getting a blowjob, but she didn’t want to do that. For some reason, sucking Denny’s cock was something she didn’t think she’d ever want to do. It felt like something so intimate and personal that she didn’t believe she’d ever want to suck anyone but Jon.
It didn’t matter. To Denny’s surprise, he became hard again almost immediately. Stephanie made him put on another condom, and soon he was inside her again. He was able to go much slower this time, and Stephanie found she could actually enjoy what was happening. She writhed beneath him sensuously, making little purring noises that let Denny know how good it felt. And it did feel good. Not as good as Jon, of course, but pretty good for someone as inexperienced as Denny.