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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 12 explains Jon’s relationship with a wonderful woman who has a troubling problem. All characters are adults over the age of 18.
In many ways, Jon’s relationship with Debbie was the most satisfying of all the college girls he dated. She wasn’t the sexiest, and she wasn’t the best lover, but she had one quality that endeared her like no other woman Jon had ever known.
Jon was thinking about this while he and Debbie were in bed recovering from a particularly satisfying session of hot, energetic sex. “I can’t help but think it’s going to be a little awkward when I go back home after the end of the semester,” Debbie said.
“Yeah. I can understand that,” Jon said. He knew that Debbie had a boyfriend back home, and there were going to be some difficult moments after they reunited. She and her boyfriend agreed that it was fine to see other people while they were apart, but it was going to be awkward for Debbie because it was going to be overpoweringly obvious that she had spent a lot of time in the bed of another man who was so good at sex he’d greatly expanded her sexual horizons. It would be hard to let her boyfriend know these things without making him feel like an inferior lover.
Her relationship with Jon started when she was introduced to him by their mutual friend, Maxine. Like Jon and Max, Debbie was a graduate student in the Department of Modern Languages; she majored in Spanish instead of French. Since most of the girls Jon dated were 18-year-old freshmen, one thing that was different about Debbie was that she and Jon were the same age. This was a significant issue, because there’s a big difference between an 18-year-old freshman and a 22-year-old grad student.
Max introduced them because Debbie complained about the challenge of finding a reliable supply of first-class cock. The boys she dated usually said they were fine having a friend with benefits, but they almost always came to want more. At her age, Debbie felt like she was too young to chain herself to men who wanted more than she would give.
Jon and Debbie had a purely sexual relationship. They never went to restaurants, bars, clubs or concerts. Debbie would come over to Jon’s apartment, they’d head for the bedroom, and she would go home a few hours later. It seemed ideal, in theory.
In practice, things started going wrong almost immediately. At first, Debbie saw Jon as a real catch, and Jon loved Debbie’s bubbly, energetic vibe. She was very lean and petite with a nice tight butt and breasts the size of small apples. In bed, she was energetic as a little bunny. The only thing she liked more than being underneath Jon with her legs spread was getting on her hands and knees and doing the doggy. A joyous smile never left her face as she tried one position after another, acting as though she thought making love was something like an aerobic workout. It was wonderful. Really. Except for one thing.
She never had an orgasm. Ever. Each time they made love, Jon worked a little harder doing the things that he knew made women climax. He gave her foreplay. Ate her pussy. Fucked and fucked and FUCKED, delaying his own orgasm longer than he’d ever done with any other woman.
Finally, after their fourth time making love, Jon admitted defeat. “Debbie, I need you to help me out,” he said. “Tell me what I need to do to make you cum.”
She let out a cute little laugh. “Oh, that’s sweet, baby. It really is. But there’s nothing you can do. I’ve never had an orgasm. It’s not something I can do.”
Jon thought she meant she’d never climaxed during sex. Surely she’d been able to make herself cum by masterbating. But no. Debbie had tried to make herself cum, but nothing had worked. She’d done some reading and discovered that about one third of women were non-orgasmic. Since she enjoyed sex – she enjoyed it A LOT – she decided not to worry about it. “Just keep doing what you’re doing,” she told Jon. “You give me the best sex I’ve ever had.”
That was not an answer that Jon could accept. Debbie was a wonderful girl. Alive. Vibrant. Sexy as hell. She deserved orgasms, and he would try his best to find a way to give them to her.
“I’d like to make a suggestion,” he said the next time they made love.
Jon ate Debbie’s pussy until she was going wild with arousal, then he had her climb on top of him in the cowgirl position. He asked her to ride him as roughly as she could, rubbing her clit against his body every time she came down on him.
She was happy to do it. It felt great, just like everything else they did in bed. Debbie loved the feel of a hard cock inside her. She Taksim escort never met a position she didn’t like. If Jon wanted her to try this particular variation of the cowgirl, she was happy to do it, even though she didn’t expect it would make her cum.
Debbie rode, and rode, and rode some more. That’s the way she always had sex – she and Jon engaged in sexual marathons that left them sweaty and drained. After a while, however, Debbie noticed that this position felt different. Her clit was responding to all the stimulation. It was satisfying in a way she’d never experienced before. She wasn’t close to having an orgasm, yet, but she was having a good time. So she continued.
And continued. And continued. Debbie ground down against Jon’s body over and over. As the minutes went by, she began to sweat, and it wasn’t long before a sheen of perspiration covered her entire body. Sweat began to drip from her nipples.
This was so stimulating that Jon found it very difficult to avoid cumming himself. Watching Debbie’s naked body work away on top of him was like his own private sex video, with Debbie performing like his own personal porn star. The sight of those perky, shiny boobs was mesmerizing. Feeling her hot, slick skin was arousing in a way he’d never experienced before.
She began moving ever more energetically, and the look on her face made it clear she was feeling sensations she’d never felt in the past. Jon was about to lose control and climax himself when Debbie surprised them both. She shivered from head to toe, gritting her teeth and saying “brrrrrrr!” as the moment passed.
It passed quickly. Debbie fell forward. Jon, who’d been on the edge of an orgasm for a very long time, thrust up into her body forcefully, then began filling her pussy with cum he’d been holding inside for a long, long, l-o-n-g time.
“Ohmygod!” Debbie said. “I. Had. An. Orgasm! A real orgasm! Jon, that was amazing!”
If that was an orgasm, it had to be the shortest and weakest one Jon had ever seen. “Are you sure?” he asked.
“Yes! Yes yes yes! Jon, I had an orgasm! I didn’t think I could do that. How did you know that would work?”
“I didn’t,” Jon said. “I mean, most ladies like it when their clits get attention, so I figured it was worth trying. I had no idea that was the magic answer.”
“That’s exactly what it was! Jon, you are a magician! I had an orgasm!”
“I’m sure you can do it again,” he said.
“How soon until we can do that again?” she asked.
“Give me five minutes. I think I’d like an energy drink in the meantime. Can I get one for you?”
Jon was smiling and encouraging, but he kept his inner thoughts to himself. That’s all? he thought. She works herself into a sweaty mess, and all she gets is that itty bitty orgasm? Something is very wrong about this.
Still, Debbie was thrilled. She was no longer among the ranks of non-orgasmic women! Yaaah! She’d been intimate with several men over the years, and Jon was the only one who had her try something that worked. She decided that she would spend as much time in his bed as possible. She wanted more. A lot more.
Jon was happy to give her more, but he was upset by the notion that Debbie seemed unable to have the kind of lasting, powerful climax he’d shared with every other woman in his past. He liked Debbie and felt she deserved better. Maybe they could figure out something that gave her a more satisfying experience.
The first thing Jon did was make a trip to the sex shop, where he bought one of those little vibrators shaped like a ring that rested at the base of his cock. Debbied loved penetration, but she obviously needed very strong stimulation on her clit. It was worth a try.
When Debbie felt the vibrator against her for the first time, she was shocked that it felt so good. She’d tried masterbating with vibrators, but it hadn’t produced any orgasms. Using a vibrator at the same time Jon’s cock moved in and out of her pussy made all the difference. She began getting excited immediately. Because Jon was doing all the work, Debbie could lie back and concentrate on the waves of pleasure spreading outward from her pussy. It took a long time and a lot of work for Debbie to climax in the cowgirl position. Using the vibrator in combination with Jon’s cock made her cum in minutes.
And this time, she had a real, powerful, big-girl orgasm. It was exactly like the kind of climaxes she’d read about in erotic novels, the kind that swept women away in explosive bursts of passion. Jon felt it too, and he was thrilled to see that Debbie had finally had the kind of orgasm he knew she wanted, needed, and deserved.
At that moment, their relationship changed. Jon was no longer a casual friend with benefits. In Debbie’s mind, he was a genius who understood more than she did about her own body’s sexual capacity. Other men had tried, and failed, to make her cum. She was so overwhelmed by the feeling of satisfaction that she determined that she would do anything Jon wanted her Taksim escort bayan to do. When it came to sex, she was his to command.
He was happy to be of service. He couldn’t stop wondering what else Debbie might like. There was a whole world of sexual techniques she might respond to. It was time to try them out, one at a time, and see what worked.
Not everything worked. In Jon’s experience, the most reliable way to make a woman cum was by eating her pussy. Debbie enjoyed it, but Jon discovered that he could go down on her seemingly forever and never make her cum. She enjoyed bondage, and though it was particularly exciting when Jon blindfolded her, it was not something that would enhance orgasms for her.
Over time, Jon noticed that Debbie responded differently to all kinds of sexual stimulation. It seemed as though the nerves in her sex organs were wired differently from other women. The most obvious sign of this came on the afternoon when Jon introduced her to anal sex. She’d never imagined that was something she’d like, her previous boyfriends hadn’t tried it, so she didn’t know how she’d respond until Jon applied a generous dollop of lube and gently began to fuck her in the ass.
Oh. My. God. It was spectacular! She loved the feeling of Jon’s cock in her pussy, but this was much better than that. It was tight, but she felt no pain at all, not even the very first time. She loved that Jon’s cock felt gigantic when it was in her ass. The slightest motion in and out produced ripples of intense sensation and overwhelmed everything else. As soon as Jon pushed inside her, Debbie began moaning and groaning so loudly that it was clear there was something special about this kind of sex.
Jon did it long enough to see that as much as Debbie loved it when he fucked her ass, it wasn’t something that would cause an orgasm. She was happy to let him do it for as long as he wanted, and she particularly enjoyed the sensation when Jon came, flooding her bottom with warm wetness. But an orgasm? No. That was not going to happen.
Fortunately, Jon already had an answer. They both knew that if Jon used a vibrator while penetrating her pussy, that gave Debbie a nice strong orgasm. It was likely that the same thing would happen if he pressed a vibrator against her clit during anal sex.
And that was the secret. Jon discovered that if he held Debbie down while fucking her ass, then pressed a vibrator against her clit, he could force her to have a climax that any woman would be proud of.
So much for the idea that Debbie was a non-orgasmic woman.
They kept experimenting. They tried spanking, which did nothing for Debbie. Oddly, she loved being whipped. Hard. Hard enough to cause real pain and leave welts that lingered for hours. It was actually easy to see what was happening. Jon would fuck Debbie’s ass and vibrate her clit until he sensed that she was about to cum. Then, he pulled the vibrator away and whipped her ass several times with his belt. The pain stopped her from coming, but left her full of sexual energy that needed to be released. Jon would repeat the process several times, and eventually he worked Debbie into a state where she was so desperate she began to beg him to let her cum.
“Jon, please, stop. I need to cum. I can’t stand much more of this. You’re taking this too far. I’m begging you, let me cum. I need it so bad.” Eventually, of course, Jon would refrain from whipping her, and she would have an orgasm so long and powerful it hurt, causing her to cry out in pain. But it was a delicious kind of pain, and it taught them both that Debbie had a surprisingly powerful appetite for certain kinds of pain.
All this was wonderful except for one problem. What would Debbie do when she didn’t have Jon to make her cum? They’d come up with a process that was complicated and choreographed as a ballet. How could she ever explain all this to another man? Would another man understand, and be willing to do it all? Debbie knew she could figure out something that would allow her to have an orgasm, but she wasn’t sure at all she’d be able to have the kind of earth-shaking climaxes she enjoyed with Jon.
They avoided thinking about this for weeks. She and Jon got better and better at getting her off. Jon was thrilled to do it. Making love to Debbie satisfied him as much as any woman he’d ever known. It was particularly good for his male ego to know that he’d done such a good job figuring out how to thrill her. Arousing Debbie made him feel like the conductor of an erotic symphony orchestra.
But Debbie never stopped worrying about what would happen when she and Jon parted ways. One afternoon she told him what she wanted to do.
“Jon, I’d like for us to make a sex video,” she said.
Jon had made a couple of sex videos with previous girlfriends, but it wasn’t something overly important to him. He loved taking erotic nude photographs of the women in his life, but he almost never watched the videos he made in the past. He’d known a few Escort taksim women who wanted to have a video they could watch together, and it had been pleasant, but nothing more than that.
“Sure. We can do that. Why do you want to?” he said.
“So I can show it to men and explain what I need for them to do for me in bed,” Debbie said.
An instructional video? That was new.
The idea made sense. Debbie figured that if they made a nice, clear video of her and Jon making love, it would make it easier for her to explain what she needed in bed. Jon realized that this meant people he didn’t know would get to see him having very kinky sex with Debbie. He didn’t like that. It wasn’t like the videos he’d made in the past, which were only viewed by him and the women. He trusted Debbie to protect his identity as much as possible, but there’s not much you can do to be anonymous in a video where you’re naked and having explicit sex.
But he saw that this was important to Debbie. She was genuinely worried about her sexual future, and he couldn’t refuse to help her. Once he agreed to do it, he decided that he’d make the highest-quality video possible.
The first thing they decided was that they wouldn’t shoot the video with a cellphone. Jon owned a first-class camera he used to take pictures of people and places he visited. It was capable of taking much better videos than the cameras in cell phones.
He owned a high-quality microphone that could be plugged into the camera, producing higher quality sound. He and Debbie set up the camera and tripod in the bedroom, checking camera angles and lighting until they had a combination they believed would work properly. Jon and Debbie usually moved around on the bed when they made love, but they realized that this time they needed to pick a spot and stay there so the camera captured all the action. They usually played music in the background when they had sex, but decided against doing that while they were filming. The video needed to capture what they said as they had sex, and background music would interfere with hearing the words clearly.
The whole thing made Jon nervous. Debbie joked that it would be good if they got a camera operator, and she suggested that Max would be willing to do it. The idea shocked and appalled Jon until he realized she was joking. They got a good laugh out of his horrified reaction.
They were anxious as they prepared. Jon showered, shaved, and combed his hair as well as he could. Debbie spent a lot of time fixing her hair and make-up. They applied a generous amount of lube to her little brown butthole. It was nerve wracking. Jon couldn’t help but think of the men who’d see him naked, performing edgy sex acts with Debbie. He was a very adventurous guy sexually, but this took him outside his comfort zone. The only reason he did it was because he cared for her.
They turned on the camera, sat down on the side of the bed facing the lens, and began to make out. Jon could tell that Debbie was having a hard time relaxing. He took her in his arms forcefully, trying to get her to concentrate on what he was doing instead of the watchful eye of the camera. She wore a sexy pair of matching bra and panties, and Jon slowly removed them. Debbie gasped when he took off her bra and she realized that the camera showed her naked boobs. That idea began to excite her. Debbie didn’t have much experience with exhibitionism, but there was something undeniably exciting about the idea of having sex in front on an unseen audience.
She reached down the front of Jon’s boxers and stroked his cock up and down. He got very hard very quickly. That was a relief, because he didn’t want to make a video that showed him having difficulty getting an erection. He had his pride, after all.
Soon they were naked, and Jon laid Debbie back on the bed, being careful to place her body inside the area captured by the camera. He tried to pretend the camera wasn’t there, but it was impossible. It was mounted on the tripod beside the bed. He needed to get on with it, so that’s what he did.
As always, Jon spent some time kissing Debbie as he caressed her neck and breasts. His hand moved slowly down her belly and began to massage her pussy and clit. This kind of foreplay didn’t do much to arouse Debbie – it was one of the things that made her different from other women – but they knew that a few minutes of this would make her wet enough to do what she really wanted and needed.
For Debbie, the thing that worked as foreplay was straight sex. What excited her was the moment Jon spread her legs, climbed on top of her body, and pushed his hard cock inside. She let out a satisfied sigh loud enough for the microphone to capture. She wrapped her arms around Jon’s back and began squirming beneath him. Jon particularly enjoyed this part of their routine. Feeling Debbie become excited was exquisitely pleasurable. He moved inside her with slow deliberateness, helping her excitement build as the minutes passed by.
In time, Debbie began to make sexy little sounds that let Jon and their unseen audience know she was enjoying what he did. Jon raised himself up on his arms, looked down at her face, and smiled. They were both finally relaxed. This felt almost as good as it would if the camera wasn’t there.
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