The Major Diaries Pt. 01

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 1 explains the clever process Jon uses to draw young women to his bed. All characters are adults over the age of 18.

The Jon Major Diaries - A Bossy Little Bitch

He looked at his students on the first day of class. There were so many beautiful girls. It was like a pussy buffet.

Jon Major arrived at grad school with an attitude problem. He'd had three steady girlfriends in college, all of them cheated on him, and they did it in ways that humiliated him publicly. So he'd given up on exclusive relationships. He decided that in grad school he'd date lots of women, insist they sleep with him if they wanted to keep dating, and insist that every relationship was open. There was no chance of being humiliated if no one expected monogamy.

In college, Jon had been primarily devoted to taking care of his girlfriends. That had to change. In grad school, he would primarily take care of himself. He'd devised a plan for sleeping with as many women as possible.

As a new grad student majoring in French language and history, Jon was a teaching assistant. He taught a weekly workshop for freshman French 101. It wasn't a hard job. He had to lead the class in simple conversations in spoken French and assign short essays based on simple questions. There was no grading or preparing lesson plans; faculty members handled all that.

Jon wasn't allowed to date his students, of course, but teaching them gave him a unique way to find the best girls to pursue after the end of the semester, when he was no longer their teacher.

He started by deciding which girls were hottest. Then, he assigned short essays based on questions he crafted to reveal the personality of each student. How do you feel about living away from home for the first time? What kind of friendships do you hope to make in college? What are the most important relationships in your life so far?

The answers told Jon what he wanted to know. If a hot girl wrote that she wanted excitement and adventure, she remained on his list of prospects. If a hot girl said her most important relationships were her parents and God, he took her name off the list. If a hot girl said that after graduation she hoped to take a year touring Europe, that piqued Jon's interest. If a hot girl said she wanted to marry her boyfriend and become a wife and mother, Jon was no longer interested.

As Jon removed names from his list, he made sure the girls got to know him, too. In college he'd worn clothes from discount stores and drove a beat-up car so people wouldn't know his family was rich. The charade didn't last a single semester because one of Jon's frat brothers did enough research on social media to determine that Jon's father was a billionaire. The only thing Jon accomplished was make his friends feel misled and insulted.

In grad school, Jon wore stylish designer clothes. He went to a first-class hairstylist. He drove two very nice cars; one was a sporty new two-seat roadster intended to impress girls, the other was a big, luxurious SUV suitable for hauling large groups of friends and luggage to fun outings. In class, the girls saw that he was handsome, fit, and looked like a model straight from the pages of fashion magazines. They learned that he spoke flawless French and English, and that he talked about sophisticated topics in a way that made him seem very mature and worldly, despite being only four years older.

The plan gave him a list of girls to chase as soon as grades were announced. On that day, Jon was free to take his list of potential lovers and see which ones he could get in bed first.

"Hi Angela. This is Jon Major," he said when he called the girl ranked number one. "I enjoyed getting to know you this semester. I checked, and I see you got an A for the class. That didn't surprise me. You were the brightest student I had."

Then came the pitch.

"Every time I read one of your essays, I always thought that you are a fascinating person, and that I'd like to get to know you better. I did my best to disguise my feelings, but I don't have to hide them anymore. Would you like to get a coffee sometime?"

Maybe it was because Jon did a good job finding girls free of entanglements and looking for adventure. Maybe it was because the girls recognized that Jon was a big upgrade from the boys they dated in high school. For whatever reason, the girls almost always said yes. Jon almost always decided they were as sexy and interesting as he'd hoped. He almost always had them in bed by the second or third date.

He got so much pussy it was a challenge to schedule the girls so he gave them each enough attention.

Angela was his very first success. She was gorgeous - a California girl with strawberry blond hair, blue eyes, long shapely legs, and an ass so round and firm it made Jon's mouth water. She had one attribute she flaunted: big boobs.

Very big boobs. Angela's double D breasts were so appealing she could use them to get boys to do whatever she wanted. Her wardrobe consisted mainly of clothes that displayed generous amounts of cleavage. She liked to bend over and give boys lots of opportunities to look down her blouse, and she made sure Jon got plenty of views during the semester.

Jon saw what was happening, and it amused him. He realized that the boys she met in high school must have been hypnotized by Angela's cleavage, but he was too smart to be fooled by such an obvious ploy. Yes, he thought her boobs looked nice. Yes, he wanted to see her naked. But it wouldn't give her the leverage she expected. It would take more than a nice pair of boobs to get Jon to do anything he didn't want to do.

Or so he thought.

Angela was very glad when Jon asked her out. She'd thought he was sexy from the first day of class, but she hadn't imagined he'd be interested in a freshman girlfriend. When Jon made it clear he wanted a relationship, Angela was quick to accept.

On the second date Jon invited her to his apartment for drinks. It was a special treat for a girl too young to order alcohol in bars. She was impressed to see that he lived in a luxurious apartment. Jon's clothes, car, and apartment showed that he had money, and Angela was quick to appreciate the advantages of a boyfriend who could take her to nice places and buy her nice things. Her high school boyfriend's idea of a big date involved bowling.

And so Angela decided to go to bed with Jon as soon as she got the opportunity. During the drive to his apartment, Angela said she was glad to go to college in California because weed was legal, and she particularly enjoyed smoking weed.

"Would you rather smoke a joint than have a cocktail?" he asked.

"Yes please," she said.

"That's easily arranged," Jon said, driving to a dispensary and letting Angela pick which brand to buy.

Jon wasn't a big consumer of weed, alcohol, or any other drug. He liked being fit and healthy. But he wasn't a prude, either, and he was happy to share Angela's favorite recreational chemical. Jon rolled them a joint, put on music, and sat next to Angela on his couch.

"This is a very nice apartment, Jon," she said.

"I am very fortunate in lots of ways," he said. "I'm glad that you like it. I hope you'll be spending a lot of time here."

He made sure Angela knew he wanted a relationship. She was smart enough to know he expected sex. That was fine; she wanted sex, too. As they passed the joint back and forth, she found herself thinking that Jon was a very handsome guy, and that she'd like making out with him.

As the joint took effect, Jon's eyes were drawn to Angela's bust. He suspected she had implants. He was wrong about that, as he'd learn later. He wanted to get his hands on those breasts, and he knew he'd try as soon as they finished their joint.

"I love the way music sounds when I smoke weed," she said.

"This feels nice," he said. "You picked out a good brand. I'll have to get some more for the next time you come over."

Next time. That sounded promising. Angela scooted closer to Jon, who put his arm around her shoulder and looked into her eyes. She wanted him to kiss her, and he wanted to give her what she wanted.

Angela had exactly one previous boyfriend. Jon had four serious girlfriends and numerous hook-ups before starting grad school. His knowledge of how to please women was so far beyond Angela's experience that she was going to be surprised. She realized that Jon was a man, not a boy. Jon was going to teach her a lot.

The most important thing Jon knew was that women needed a man who could go slow. Looking down at Angela's bosom made it easy for a boy to want to rush, but Jon was not like that. He kissed Angela gently, almost chastely. He kissed her again, and again, and he kept kissing her until she was moaning and urging him to explore her lips and mouth.. She expected him to touch her breasts, but he refrained. Instead, he held her hand and began kissing her neck and shoulder.

It was like throwing gasoline on a fire. Angela was already powerfully attracted to Jon. Smoking the joint transformed that attraction into lust. Her boobs were beginning to ache, and they wanted attention. Jon ran his hand up Angela's arm, almost touching one breast. It was maddening. She couldn't stand it anymore. So she did the thing Jon waited for: she took his hand and placed it directly on her boobs.

He squeezed gently, prompting Angela to moan through their kiss. He pressed his hand against her, then traced along the skin at the boundary where her top exposed her cleavage. Feeling Jon's finger slip between her breasts was agonizingly pleasurable. She wanted a lot more than he was giving her, and she ached for him to tear off her top and have his way with her. Other boys had been in a hurry. Why wasn't he? Didn't he like her boobs?

Jon loved her boobs, but he loved her growing arousal even more. He could tell she was getting desperate. That's exactly what he wanted. He knew that girls liked a man who moved slowly from one sensation to the next, giving them plenty of time to savor it all.

Jon pushed one of her shoulder straps down. He slipped her bra strap down next. Angela was thrilled that Jon was finally going to expose one of her breasts, but she was frustrated that he was taking so long. She sat on the couch, paralyzed with desire, aching for the feel of his hand on her bare flesh. He kept getting closer, and she was sure he'd get there eventually, but her skin seemed to burn as she waited and waited and waited.

When he finally pulled the fabric away from her breast, Jon leaned down and sucked the nipple between his lips. "Ohhhhhhh!" Angela said. She was surprised to feel Jon's lips instead of his hand, but it was the best possible surprise. She leaned back on the couch and panted with desire as he worked to excite her. Angela's heart was pounding. The sensations coming from her breast were exquisite. This was either the finest weed she'd ever smoked, or Jon was a master at arousal. Maybe both.

It also seemed that Angela was exactly what Jon wanted. She was a beautiful, sexy girl who didn't have much erotic experience, but was eager to learn. Jon knew he'd enjoy introducing her to sexual experiences she knew nothing about. He also knew that by treating her gently at first he'd show her he could be trusted - which would be important when he started making her do things she wasn't sure she wanted. Jon enjoyed nothing more than showing a woman how to enjoy edgy, kinky sex that was outside the boundaries of what she thought she'd like. He liked teaching women to enjoy bondage. Spanking, Deep throat. And he particularly liked surprising women who never imagined they'd be interested in anal sex. By the time Jon finished, Angela would beg him to fuck her ass.

As he sat next to her on the couch, watching her squirm under his touch, he knew he'd been right to rank her at the top of his list of hot freshmen girls who'd want to wrap themselves around his cock. Angela's legs were as far apart as she could spread them. Jon saw that she wanted to be touched between her legs. He'd do that for her, but not yet. It was time to take her top off.

Angela looked at him through half-open eyes when he began lifting her top free. Without being asked - without even thinking - Angela raised her arms over her head so Jon could remove the last barrier between his hands and her boobs. It was easy to see why she was so proud of them. They were magnificent.

He'd suspected Angela must have implants, but her boobs looked completely natural, and they felt that way. Angela liked to think of her breasts as "big naturals," a term she knew that guys used to describe especially large tits, like the type found on well-endowed centerfold models who didn't have implants. She took a good look at Jon's face as he got his first glimpse of her naked boobs. Angela was pleased to see that Jon liked them as much as she'd hoped. She wanted Jon to like her tits, and to spend lots of time caressing, kissing, and sucking on them.

Jon was glad to hear her squeal in pleasure when he bit one gently. He felt like he could play with her breasts all day, but this was their first time together, and he needed to give her what she wanted next.

"Let's take this to the bedroom," he whispered, standing up and taking her hand. Angela nodded and let him lead the way. As she moved, Angela realized that her pussy was extremely wet. It felt squishy as she walked.

Jon unhooked Angela's belt and lowered her shorts to her feet. When he removed her panties, he saw they were damp. He lowered her back on the bed and took a good, long look at her naked body. Everything was lovely, from her dainty little feet to her beautiful feminine face.

She had one feature he'd never seen on a woman. Her pubic hair was the same color as the strawberry blond hair on her head. He'd seen several girls who had "carpets that match the drapes," but he'd never seen this particular shade of blond. Most girls her age shaved their public hair, but Angela trimmed it down to a broad triangle that left plenty of blond hair to admire. Jon was glad to see she shaved the hair around her labia; that would make it easier to eat her pussy.

Angela saw Jon examining every inch of her body, and it made her feel exposed. She was one of those unfortunate girls raised to think nudity was shameful, so she tried to cover herself with her hands. Poor kid. Jon knew he'd need to help Angela get over this burdensome inhibition.

"Don't do that," Jon said, taking one hand, then the other, and moving them to her sides. Angela's feeling of nakedness grew stronger than ever, but Jon was smiling in a reassuring way. She left her hands where they were.

Jon was still fully clothed, but he wouldn't be for long. He removed items one at a time, letting her see his body. She looked a bit fearful when he lowered his boxers, making his hard cock spring free. He got a condom, but Angela stopped him. "We don't need that," she said. "I've got an IUD."

Jon had forgotten. He'd known Angela was on birth control. In one of her essays, she'd written that the first thing she did after moving to campus was go to the student health center and get an IUD. She wrote that taking care of birth control in advance made her feel like a mature, responsible adult. When Jon read that, he moved Angela to the very top of his list of prospective lovers.

He laid down beside Angela, pulling her close. His hard cock pressed into her hip. Angela had a boyfriend when she was an 18-year-old in high school, but she hadn't hooked up with anyone since starting college last semester. She was getting horny. It felt wonderful to know that Jon was about to end her celibacy.

Raising up on one elbow, Jon kissed her. She didn't need soft, delicate little kisses; Angela was ready for deep, soulful kisses that would get her ready for what was about to happen. He caressed her big, beautiful breasts, then began running his hand down her belly. Angela spread her legs so Jon could touch her there.

She exhaled a long, satisfied breath when his hand finally reached her pussy. That big blond bush was so beautiful that Jon wanted to go down on her, but he decided to save that experience for the next time they made love. Jon knew Angela wasn't a virgin, but she didn't have much experience. It was possible no one had ever eaten that lovely blond pussy. Jon knew that some girls were frightened when men went down on them the first time. He would use his hand. His tongue could wait until next time, when she was more trusting and comfortable with him.

Angela felt Jon dip one finger into her warm wet slit, and she clamped her legs shut. It wasn't that she wanted him to stop. It was just that the sensation was so powerful she moved reflexively. "Relax," Jon said, reaching down gently and spreading her knees as far apart as was comfortable. When he put his hand back on her pussy, she was finally ready.

She moaned as Jon moved one finger up and down her inner lips. He avoided touching her clit, knowing Angela would like it more if he gave her some foreplay first. When he finally moved his wet finger over and around her clit, Angela began squirming on the bed, obviously drowning in erotic desire.

Jon kept this up for a long time. Too long, Angela thought. When he slipped one finger all the way inside her, Angela wished it was his cock instead. What was he waiting for? Couldn't he tell she was going out of her mind? This was nothing like the way she'd been treated by her high school boyfriend. He played with her pussy for a short while, then shoved his cock inside her and pumped away forcefully. Angela thought that felt good, but she was always disappointed when her boyfriend came. She'd wanted more. She'd had lots of orgasms from touching herself, but she'd never cum during sex. She'd read that lots of women had trouble having orgasms, and she thought it was normal.

It was not normal with Jon. He slipped a second finger inside Angela and used his thumb to massage her clit. That did it. Angela began to cum, and cum hard. Her body shook. She groaned. Jon felt throbbing as the muscles in her pussy contracted. When she opened her eyes, Angela saw that Jon was watching her cum. She felt so exposed it made her blush.

"You look beautiful. Just beautiful," Jon said, trying to reassure her. If things worked out, Jon expected to watch Angela have lots of orgasms in the weeks and months ahead.

She couldn't quite believe she'd had an orgasm, and Jon hadn't even begun using his cock. Angela reached down and wrapped her hand around it. His cock felt so good. It would feel wonderful inside her. It had been too long since she'd had a cock, and her pussy was hungry for it.

She didn't want to wait any longer. "Give it to me," she pleaded as she gave his cock a squeeze.

That's what Jon was waiting to hear. With a little effort, Jon thought he could train Angela to beg for what she wanted. She would learn that Jon loved hearing women beg.

He climbed on top of her body, took his cock in hand, and put the tip at the entrance to her pussy. And then he waited. Jon always waited. He'd learned that it was easy to move too fast for a woman, but it was hard to move too slow. Angela waited for him to slip inside her for the first time, and she waited, and she began feeling so frustrated she grabbed him around the waist and tried to pull him up and inside her. "Please, Jon," she implored.

Jon finally gave her his cock, and she went "Yessss!" Jon liked it when girls made noise. If Angela turned out to be a loud lover, it would be one more reason she'd be welcome in his bed.