The Major Diaries

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 13 explores the final conclusion of Stephanie's relationship with Denny. All characters are adults over the age of 18.

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As the months went by, Jon and Stephanie spent many wonderful afternoons in each other's arms. Their love grew by the day, and so did their physical passion. Since they could not risk exposure by appearing in public, the primary way they expressed their affection was in bed.

Since Jon could not take Stephanie with him on dates to clubs, restaurants and concerts, he spent many evenings and nights with a stable of college girls who were happy to provide female companionship. Things were the same with Stephanie, who could not take Jon to her high school social events. To fill this need, she continued to pursue a relationship with Denny, a fellow student who considered himself the luckiest boy alive because Stephanie let him spend time with her. Since Stephanie wanted Denny to be her high school boyfriend, she decided to give him the physical attention he had every right to expect. They started slowly, by doing things like holding hands, but things escalated until the day Stephanie decided to relieve Denny of his virginity.

It was blissful for both of them, but especially for Denny. He did a good job thinking of creative dates Stephanie would enjoy. They did a lot of ordinary things all high schoolers did. They went roller skating. Bowling. Hiking. Picnicking. Denny earned a lot of points in the boyfriend department when he invited Stephanie on a date to the art museum. She loved getting dressed up and wandering through the beautiful building full of marvelous works of art. They held hands as they moved from gallery to gallery. They felt very grown up.

But the most important thing they did was have sex. They found plenty of opportunities. Usually it happened in Stephanie's bed because her mother worked as a nurse during afternoons and evenings, so they had lots of privacy. They sometimes made out inside Denny's car. Stephanie made it clear she was happy to do that, but she told Denny she had no interest in having real sex in such a cramped space. If they couldn't find a place to stretch out and be comfortable, Stephanie wasn't interested, and she felt it was important for Denny to learn that a gentleman does not ask such things of a lady.

Overall, things were going well for both of them. They had a rich social life in public, and a passionate sex life in private. There was just one problem, and Stephanie was determined to fix it.

The problem was that they'd had sex several times, and Denny still hadn't found a way to make Stephanie have an orgasm.

Stephanie knew she wasn't the problem. Jon made her cum every single time they made love; he usually made her cum more than once. Denny seemed to be an example of the kind of clumsy lovers Stephanie read about in women's magazines. He moved too fast, didn't last long enough, and wasn't very good at finding the parts of her anatomy that needed the most attention. It was becoming annoying.

She had to fix it.

"Denny, I'd like you to do something for me," Stephanie said one afternoon as she and Denny climbed into bed. "Would you do me a favor?"

"Of course. Anything," he said, taking her in his arms.

"There's something that I think I'd enjoy. I'd love it if you ate my pussy," she said.

Ate her pussy? Denny knew what she meant, but he had no idea how to do it. Still, this was something Stephanie wanted, and he would do anything for her. "I'll try," he said. "I'll need you to tell me what to do."

"You just get started, and I'll tell you what feels good," she said.

Denny felt pretty intimidated when he climbed down between her legs and found himself facing her pussy. He felt every inch of Stephanie's body was beautiful, and that included her pussy, but he didn't know how to proceed. He knew that she liked it when he reached down and massaged the area, but that didn't tell him what to do next.

"Try licking me," she suggested.

A skilled lover would have started by kissing, nibbling and licking the tender flesh of her inner thighs before moving to her outer lips, then licking her moist inner folds before touching her tender, sensitive clit. Denny just started licking her slit from top to bottom, being much too rough with her clit. She grimaced the first time, but things got better as Denny's wet tongue helped lubricate the area.

It wasn't a bad start for a beginner, but Stephanie couldn't help comparing Denny's clumsy effort to the masterful skills of Jon, who could use his tongue and lips to make her climax almost effortlessly.

Practice makes perfect

, she thought.

He'll get better with a little coaching from me.

"There. Right there," she said, letting him know where to concentrate his efforts. "Be gentle. I like it when you're gentle down there."

Denny noticed that Stephanie started getting wet, and he liked the way she tasted and smelled. He started trying to lap up her female fluid, and that got him to use a motion Stephanie liked. He heard her gasp in delight, and it helped him realize he'd found a way to make her feel good.

He began paying a lot of attention to the entrance of her pussy, licking as far inside as he could. Stephanie started making sexy little sounds intended to encourage Denny to keep that up. She'd teach him. It would just take time.

For some reason, Denny seemed unable to stimulate her clit in a way that excited her. He was clumsy, rough, or unable to find the target. Stephanie couldn't think of a way to explain the problem, so she just laid back and enjoyed it as much as she could. It wasn't great, but it was better than nothing. Certainly, it was better than the rushed, clumsy way Denny usually started making love.

In time, Stephanie realized that Denny had done an acceptable job preparing her pussy for more. She decided to let him know she wanted more. "Come up here. I want you in me," she said.

Denny climbed up, but had to take a break long enough to put on a condom.

Shit! Why didn't I have him put that on first?

she thought. Her excitement had been building nicely, but the condom interrupted her arousal.

There was nothing that could be done. Denny unrolled the condom, then lowered himself on to Stephanie's body and spread her legs. He slipped inside easily. One thing he'd done well is get her lubricated enough to proceed comfortably. His cock entered her body. It felt good. Things were going better than they usually went.

"Slow," Stephanie said. She found it a bit annoying that she had to continually remind Denny to stop moving so fast. He should have figured this out by now. Still, he was able to do as she asked, and he moved in and out at a pace that Stephanie enjoyed.

She was more aroused than usual with Denny. The time he spent eating her pussy hadn't been as good as it should have been, but it had served as more foreplay than he'd given her before. As she felt her pussy become increasingly excited, she thought that this might be the day Denny finally made her cum. She hoped so. She was getting tired of sex that ended before she was satisfied. It was getting difficult not to become annoyed. She had to remind herself that it wasn't Denny's fault that he didn't have the kind of skill and experience she got from Jon.

After some time it began feeling good. Very good. She wrapped her arms around his big strong back and squirmed beneath him. Denny thought her movements were breathtaking. Erotic. Sensual. Amazing. Stephanie was everything to him.

That's what he was thinking when his climax began. Stephanie felt disappointed. It was just beginning to feel good, and now it was finished. @#$! As she felt Denny's cock throbbing over and over, she wished there was some way to prevent him from going soft.

But it was hopeless. By this time Denny knew it was important for him to pull out of Stephanie's body before the condom slipped off. She was glad he'd learned this lesson, because it was something that would be important for the women he dated in the future. But it did nothing about the fact that Stephanie was fully aroused, and Denny wouldn't be able to continue for several minutes.

There was nothing that could be done.

"Was that alright?" Denny asked.

Stephanie wasn't sure what to say. She didn't want to lie, but she knew the truth would hurt his feelings. She decided to dodge the question. "Thank you for eating my pussy," she said. "That really got my engine running."

Denny grinned, clueless about the depth of frustration Stephanie felt.

This is getting old

, she thought to herself.

Is he ever going to get this right?

One thing Denny had learned was that Stephanie liked to cuddle, and that when they did it long enough he'd get a second erection, and it would last longer than the first. Indeed, after several minutes elapsed, Stephanie began stroking his cock, and soon it was hard again. Denny put on another condom and moved to get on top. Stephanie stopped him. "Let me do the work this time," she said.

This wasn't the first time Stephanie used the cowgirl position on Denny. He knew she wanted him to lie on his back so she could straddle his body and ride his hard cock. He loved the cowgirl position. He didn't realize why, but it felt better when Stephanie was in charge. The plain fact was that she knew how to move in ways that felt best. Denny would gain that skill eventually, but it hadn't happened yet. All he knew was that Stephanie moved around on his body like an erotic dancer, making his cock feel as good as it ever felt.

It worked, of course. Stephanie began to feel the kind of pleasant, arousing feelings she needed. Her excitement grew, and she felt an orgasm growing inside her. She began to move faster. She ground her clit against Denny's body hard. She gritted her teeth and tried, and tried, and tried, but she finally realized it was not going to work. Like all women, Stephanie needed a certain amount of a certain kind of stimulation to have a climax. She hadn't gotten that, and her body was past the point of being able to make it happen. It didn't matter how long she rode Denny. It didn't feel bad, but it didn't feel good enough. She wasn't going to have an orgasm. Again.

Of course, this wasn't a problem for Denny. Stephanie rode him long enough to make him cum, and she got some satisfaction from seeing the smile on his face as his cock throbbed inside her. She laid down next to him, put one arm across his chest, and enjoyed being next to his big, strong body. She took some satisfaction in knowing that she'd managed to get him to eat her pussy, and she imagined he'd do a better job the next time he tried.

Over the next few days Stephanie asked herself what she could do to make sex with Denny more enjoyable. She decided to tell him they didn't need to use condoms anymore because she'd gone to a doctor and gotten an IUD. That was all true, of course, but she didn't mention that she had the IUD before they started dating. She let him believe she'd gotten it for him. She hoped she'd done enough to teach Denny the importance of contraception.

Denny loved how it felt having sex without condoms. Stephanie liked it better, too. The first time they did it, Denny had an orgasm almost immediately, and Stephanie realized she'd have to start over on lessons that taught him how to make sex last. As always, she made Denny cuddle long enough that she could massage his cock and make him hard a second time.

For some reason, that's when everything came together for Denny. Without a condom, it felt more natural to use the slow, gentle in-and-out motions women prefer. Since he no longer felt an urgent need to climax, he had more time to arouse Stephanie. She felt the difference. Denny was gradually pushing her in the direction she needed to go. Could he go all the way?

It was the first time Stephanie was able to lay back, relax, and enjoy what Denny was doing. This was a definite improvement. She knew there was a possibility that he'd disappoint her again, but at that moment Denny was doing everything right.

For whatever reason, it worked. Stephanie felt her orgasm begin.

Yes! Yes! Yesssss!

She thought to herself.

I'm going to cum this time!

Denny realized something was different. Stephanie began gasping for breath as her body shook beneath him. He felt her pussy clenching and unclenching. "I'm cumming . . ." she said, making sure he understood that something new was happening. Maybe it would help him make it happen more often.

As orgasms went, it was nothing special. It wasn't overly powerful, and it didn't last an overly long time. But it was the first time Denny made her climax, and the big smile on her face let Denny know he'd done a good job. He hadn't fully understood that he'd fallen short in the past. Now he knew, and he knew what to do about it.

"Oh Denny! That felt so good! So good!" Stephanie said between breaths. Denny began moving in and out of her faster. Her orgasm was so exciting that he was ready to cum again. Before long she felt him pounding into her pussy, then slamming into her one last time before his cock filled her with warm wetness.

"Wow," Denny said.

"Wow is right," she said. "That was just wonderful. I liked everything about that." Denny smiled wider than she'd ever seen. He looked proud as a puppy who'd learned to do a trick. He wrapped his arms around her and squeezed, feeling very masculine and grown up. He understood immediately that he'd done what Stephanie needed him to do. He understood what he needed to do in the future.

Stephanie laid back and felt smug. She'd vowed to make a man out of Denny. It seemed she'd succeeded. He still needed practice - a lot of practice - but there wouldn't be any more times when they had sex and it ended before Stephanie was satisfied. They were past that problem.

They continued going out on the kind of dates you'd expect from a couple of high school students. Stephane started attending basketball games so she could watch Denny play, and they'd get together afterward to have a snack somewhere. They went to the homecoming dance. Mainly, however, they found time for Denny to visit Stephanie at home while her mother was away at work, and they used the opportunities to jump into bed and have sex.

Stephanie saw that Denny was falling in love, and she realized there was nothing she could do to stop it. He was behaving like a normal teenage boy having his first sexual relationship. It was part of what she needed him to learn. To make sure that happened as gracefully as possible, she regularly made little comments designed to prepare him for the future, after they were no longer together.

"I'm looking forward to college," she mentioned once. Denny knew she had a full-ride soccer scholarship at UCLA, and she talked about her expectation that college would be a great adventure. She talked about going to new places, doing new things - and meeting new people. She made sure they discussed his college plans, which included doing his first two years at a local junior college that offered to pay his tuition if he played basketball. By living at home, Denny would save his parents so much money that they agreed to pay for him to finish his degree anywhere he wished, and that they'd pay for him to live in a dorm or in off-campus housing.

These conversations stressed the fact that they would spend the next four years in places so far apart a relationship was impossible. Denny might have entertained thoughts of trying to maintain a long-distance relationship, but Stephanie was careful to talk about things in a way that made it clear she had no interest in that. She said she was looking forward to the time when they could both make new friends - and by friends, it was clear that included lovers.

One conversation happened after they learned that a senior girl at their high school had become pregnant, and that she and her boyfriend planned to get married after graduation. "I hope things work out for them, I really do, but I expect them to have a difficult time," Stephanie said. "People our age are just too young to chain themselves down to a lifetime relationship. People our age need to date lots of people. We need to get a lot more mature before we start making babies and getting married. My Mom has spent a lot of time lecturing me about the dangers of falling in love too young. I'm glad we're both sensible enough to use contraception. I would hate for us to be in that situation."

Denny knew they had to part when it came time for college, but he continued to hope they could date over the summer after graduation. Stephanie was not willing to let that happen. She decided that after the last day of classes, she would reveal to her mother the truth of her relationship with Jon. At that point she felt comfortable demanding that she be treated like the adult she was. Stephanie's mother might never become willing to accept the notion that her baby girl was in an adult romance, but the secrets were going to stop with graduation. That meant she and Jon would be able to date openly, and there would be no room in her life for Denny.

She made sure to avoid surprising Denny with this news at the last minute.

"Denny, you know I think the world of you," she said one afternoon. "I know you realize that the day is coming when we can't see each other anymore, but I want to make sure you know how I plan to spend my summer. I have things I want to accomplish this summer, and I'm not going to have time to continue our relationship. Besides, we both know we have to split up eventually. If we tried to keep seeing each other all summer, it would only make things harder on us in the fall when we start classes at different colleges far from each other."

Denny didn't know what Stephanie meant when she talked about "things I want to accomplish," but he was smart enough not to demand details. He understood that there was nothing he could do to keep Stephanie in his life forever, and he loved her enough to respect her wishes.

But he hated thinking about the day they would part.

When that day came, they arranged to make love one last time. At long last, Denny had learned enough about how to satisfy a woman. He started by kissing Stephanie passionately as his hands roamed over her breasts. He'd mastered the art of stimulating her nipples just the way she liked, sucking and nibbling until she moaned with arousal.

He massaged her pussy until her feminine scent filled the room, then he moved to go down on her. He spread her legs and began kissing, sucking and nibbling the flesh of her inner thighs, starting at the knees and working north slowly. Stephanie luxuriated in the anticipation of the moment his lips reached her labia, when he would kiss around and around her pussy until it was hot and wet, and she was squirming with desire.

He used his tongue to gently caress her delicate inner folds, lick deep inside, then gently touch her inflamed clit. He began applying more force, sucking her clit between his lips and licking it rapidly. Stephanie started thinking he might make her cum this way, but he wasn't quite good enough to make that happen. Jon knew how to do that; Denny would learn eventually.

Instead, he worked Stephanie into a frantic, desperate state, then moved up her body and placed his cock at the entrance to her pussy. He paused for a moment to kiss her lips as he teased her with his cock. She was beyond ready when he finally pressed the head of his cock inside her.