Jack's Education Ch. 01

Note to reader: The stories previously posted in the series "Jack Awakens" and "Jack's Exploits" were originally the opening chapters of a book which I had started writing over the last few months. I have now decided to post the entire book, which traces the sexual development of a high school boy during his senior year, hopefully at the rate of one chapter each week. The stories previously posted have been retitled as "Jack's Education" in strict chronological order, under the "Novels and Novellas" classification, as the book covers a variety of sexual behaviors and experiences.

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This is the story of Jack's sexual development, and it really begins as a high school senior. As shall be seen, he proves to be a quick learner, despite getting a relatively late start in gaining sexual experience. His eighteenth birthday had already passed and his only regular sexual activity to that point had been jerking off in the privacy of his bedroom. His fantasies as he jacked off generally revolved around big-breasted long-legged blondes that existed only in his imagination. He was a shy boy and never really had the nerve to approach any of the girls he knew, and he knew that other guys of his own age were already engaging in all kinds of sexy romps with the opposite sex. It wasn't that he had no interest, but simply lacked the self-confidence to pursue any opportunity that might have arisen. As often happens, it was really a spur of the moment incident that opened wide the floodgates of his sexual activity. Jack still vividly remembers that first episode in the spring of his senior year, which was the first time he had ever ejaculated in the presence of another person.

The day it all started Jack had been feeling much hornier than he ever remembered feeling before. He was still too timid to ask any of the girls he knew at school for dates or indeed to approach them for anything but the most trivial things. During class that morning Jack had helped one of his classmates Tim Howard with some of his homework that was late and at break Tim sought him out to thank him. Tim and Jack had never really got to talk to each other before as Tim was one of the top athletes in the school and was on all of the school teams. Jack was never athletically inclined, so he had been hesitant to strike up a friendship with a guy that was almost worshipped by all the guys, not to mention the girls. He was an imposing figure being six feet tall with very muscular legs and a well-defined chest and had short almost white blond hair. He had a light skin tone and the blond hairs on his arms and legs barely stood out against it. He was really grateful for Jack's assistance and as they talked, really for the first time, Jack began to realize that Tim would be a good friend to have, as he seemed much more friendly towards Jack than he ever imagined he would be. Before the end of their conversation it became clear to Jack that Tim liked him too, especially since Tim had asked him if he would like to go for a burger after school. It seemed to Jack that Tim could have his choice of any girl in the school, so he was a bit puzzled by the invitation, but nevertheless he was glad to have a chance to be out with such a popular guy. That day being Friday, Tim invited him to come and watch the afternoon practice of the track team, so after class was finished he headed over to the athletic complex. He spotted Tim almost right away as he was the tallest member of the track team, and watched with a certain amount of pride as Tim raced easily around the track. After about fifteen minutes the practice ended and Tim came jogging off the field towards the locker room. He came up to Jack, saying "Hey, buddy. Glad to see ya! Ready for that burger now?"

Jack smiled and replied, "Sure, that's great!"

"OK. Give me a few minutes to change and we'll go over to Johnny Rockets." About ten minutes later, Tim reappeared, still wearing his track clothes. "These showers aren't working. Why don't we go by my place so I can shower and change?"

"OK. That's fine with me," replied Jack.

They went out to the parking lot to Tim's Beetle to make the short drive to Tim's house. On the way they chatted, just getting to know each other better. When they got there, Tim explained that his parents wouldn't be home from work for a couple of hours, so they'd be by themselves for a while. Tim pulled into the garage and they went in the side door.

Once they were inside the house, Tim said, "Come upstairs so I can show you my exercise room!"

They went upstairs, and Tim took him into what appeared to be one of the bedrooms that had been emptied of most of the bedroom furniture to make space for a huge treadmill and a Bowflex machine. Tim asked him, "Ever seen one of these before?"

"Well, I've seen the TV ads, but I've never seen one in real life."

"Let me show you how it works," responded Tim as he slipped off his shoes and then pulled off his track clothes, leaving him clad in only a jockstrap, barely concealing his quite substantial package. Now, one of Jack's pleasures had been to look at the other guys' cocks as they showered after physical activities, just to see how theirs compared to his, so he knew that Tim had a nice one, even though he felt that it wasn't any bigger than his own. Jack himself was only average build, standing at 5'10" with brown hair and blue eyes, but his cock when erect was almost seven inches long, with a thick mound of brown pubic hair at its base.

As he watched Tim demonstrate the Bowflex, lying almost naked on his back and stretching his muscles with the weight rods, it seemed to Jack that Tim's cock was starting to grow harder and this triggered a similar reaction in his own! As Tim finished explaining the merits of the machine, he got up and said, "I stink! I gotta get me a shower!" and immediately stripped off his jock, unselfconsciously standing completely naked in front of Jack with his cock semi-hard. He went on, "Want to give it a try?" and when Jack nodded, said, "OK, let me show you how. First you might want to take off your things, 'cos it gets awfully hot in here." At first Jack was hesitant, because he knew he didn't have the same kind of physique as Tim, but then he thought, 'What the hell, why not?' and stripped down to his boxers. Now Tim could see that Jack's dick seemed erect beneath his shorts and Tim's started to become fully hard.

"Got a little excited, huh?" he asked.

Jack blushed, feeling a little ashamed. "Uh, yeah," he mumbled.

Tim chuckled. "Hey, dude, it's OK. Take 'em off and let me see."

Jack complied, pulling the garment past his hips, so that they fell to the floor. "You've got a nice one," Tim said. "You like looking at the other guys' pricks in the shower, don't ya?" Jack nodded weakly and Tim went on, "Me too! Being on so many teams, I get to see all kinds of guys in the buff. It's really great!"

Jack replied, "I thought it was only me who liked it. A lot of the guys don't stay in the showers too long."

"That's only because they don't feel good about their bodies. So now, here we are with two perfectly good hard-ons and no pussy in sight! What a dilemma!"

Jack's stomach flipped when he heard Tim mention pussy, for he had never seen one except in magazines, let alone smelt or touched a live one! Tim continued, "Come on, let's take a shower so we can cool off!"

Jack followed Tim into the master bedroom suite, where Tim's parents had a spacious bathroom with a walk-in shower as well as a huge tub. Tim turned on the shower and grabbed some towels from a closet. Jack ducked under the stinging water which felt so good on his body and Tim joined him in a couple of seconds. They each grabbed some soap and start lathering up each other's bodies, and this caused Jack's cock to become hard as steel and couldn't help but notice that Tim's strong dick was also fully erect.

"I want you to jack me off," Tim said. "OK?"

"Sure," Jack answered readily, although unsure what he should do.

"Good! Let's do it then," Tim said, handing the soap to Jack, who took it, lathered up his hands and spread the soap over Tim's erection. He dropped the soap and started jacking the hard dick quickly, thrusting up and down its full length, until he got tired and paused briefly.

"OK, that's good. Keep on doing it like that, only faster. After I come, I'll do you," Tim said.

Jack picked up the soap and lathered up Tim's cock again and resumed jacking Tim's throbbing prick with his right hand, getting into a quick rhythm right away, concerned only with finishing him off so Tim could give him his nut, which he badly needed now. Tim seemed to like what Jack was doing, as he started making a low moaning sound and Jack closely watched Tim, his eyes closed to mere slits in his face, and his face screwed up in an expression of what looked like intense pain. Jack soon found out that it was actually pleasure that Tim was feeling, as he suddenly let out a sharp, quick groan and released his load of cum. It shot out in large white globs, a couple of which hit Jack in the chest.

"Ahhh, that was great, Jack," he said, breathing hard, his cock slowly growing limp as he stood under the showerhead.

"I liked it too," Jack answered as he washed Tim's cum off his body.

"Now it's your turn," Tim said, grabbing Jack's cock, which was now standing up like a steel rod, and started jerking it with his hand. Suddenly he pulled the prick towards his lips and before Jack could say anything, his dick disappeared inside Tim's mouth, and a warm sensation immediately enveloped his cock which felt exquisite. The combination of the excitement of jacking off Tim and this new sensation was way too much for Jack to handle and as Tim moved his lips back and forth on his cock, Jack felt a load of cum rushing up his shaft.

He yelled out, "I'm coming, I'm coming!" and pulled his dick out of Tim's mouth. As he pulled out, a long stream of cum shot out of the head of his cock, splattering Tim's face with globs of jism. "Shit!" he said, "that was great!"

Tim washed himself off and then they toweled themselves dry before Jack went back to the exercise room to get dressed. Tim called out to Jack for him to come into his room as he put on fresh clothes.

Tim asked, "You ever do that before?"

"Sure, I do it all the time."

"No, I mean with another guy."

"Oh, no, I never did it with anyone else."

"How about with a girl? You ever have a girl do that to you?"

"No, I don't have a girl friend right now. Do you have a girl friend?"

"No one special. There's a couple of girls I go out with sometimes, but I'm too busy for a steady girl."

"Yeah, me too," Jack said, relieved that he didn't have to explain the real reason why he didn't have a girl friend.

Tim grinned at him and said, "Anyway, I enjoyed our little session together. You're a cool guy, much different from what I thought before you helped me with my homework. I really owe you one for that. I could have gotten into a lot of trouble if I hadn't turned it in on time. Being a jock can only take you so far, and you have to keep up your grades to stay on the team."

"You're welcome, Tim," Jack answered. "I think you're cool, too, and I'm glad to have you as a friend."

"That's right," Tim said, "We're buddies now! Look, I need to straighten up the bathroom and then we'll go downstairs for a soda."

After completing their chores the two friends go downstairs to the kitchen and Tim pulls a couple of cans of Coke from the fridge. After they each popped one open to take a deep swallow of the sweet fizzy liquid, Tim asked Jack, "You ever been fucked up the ass, Jack?"

Jack replied, "No, not me. I'm not really into that kind of stuff. Are you?"

"Well, I've done it a couple of times and it's kinda cool, a change of pace from pussy!"

Jack was taken aback by this but felt secure enough with Tim to come clean about his sexual experience. "Tim, can you keep a secret?"

"Sure, Jack. What is it?"

"Well, actually I'm a bit embarrassing to admit this, but I've never fucked a girl. Worse than that, I haven't even kissed a girl yet! You are the first person I ever had any kind of sex with in my life!"

"Wow, you're a real virgin! How come?"

"Well, I still feel real nervous about approaching girls, so I never do. I guess I have always felt my cock was too small and that any girl I might try to have sex with would laugh at me. But, I must say that the way you opened yourself up to me and allowed me to feel what I did just now has really given me some confidence. After all you're considered to be a hero in the class, as you are much taller and stronger than anyone, as well as being an accomplished athlete."

"Thanks for saying that, but remember I'm almost a year older than anyone else in the class, so I'm bound to be bigger. But as regards your cock, you really don't have anything to be ashamed of. I saw you checking out the other guy's cocks, so that should have told you that you don't have to worry. I know plenty of girls who would jump at the chance to get a piece of meat like that between their legs!"

"Well, that's comforting. You mind if I ask you a personal question?"

"Fire away!"

"You know plenty of girls and could have sex with any of them any time you like, so how come you want to spend Friday night with me?"

"I wanted to show you I was grateful for what you did. I'm not gay or anything like it, but let's just say I like to have plenty of sex and I don't mind if it's a guy or a girl. I like to take advantage of every opportunity, 'cause you never know where it could lead. Seeing you aroused like that made me horny too and I needed to do something about it. Whenever I get horny I want to come, even if I have to do it myself. You know how that is, I guess. But I can't believe you never had a girl! That's really something! You do want to do it, don't you?"

"I really do! I just haven't been able to get up the nerve to ask a girl if she wants to do it!"

"There's your problem! You don't ask! All you need to do is get yourself into a situation where she wants it as much as you do."

"But how?"

"Jack, you gotta understand that girls like to be fucked! They just need to be worked up to the point where they can't resist. I think we gotta get you laid as soon as possible, so you can understand how things work!"

"And how do you propose we do that?"

"I have some ideas, but let me think about it. Since you are interested in girls, I have something in my room I want to show you. Let's go back up before my parents come home, OK?"

"Sounds intriguing, let's go then!"

They quickly went back to Tim's room and Tim closed the door behind them, before pulling a storage chest from under his bed and unlocking it. He pulled out a thick photo album from the chest and sat on the bed next to Jack. When he opens it, Jack is surprised to see that all the photos are of girls in various stages of undress, including many completely in the nude. Some of the photos are of top quality like they were taken in a studio, while some others are less distinct as if taken from a distance. There were nude photos taken outdoors and at the beach and even some taken from ground level looking up girls' skirts, showing their underwear and in some cases no underwear at all! As Jack looked through the pages, he noticed that some of the photos are actually of older women posing in all kinds of revealing positions.

"This is one of my hobbies," Tim explained. "I've always been a keen photographer, as you can see from my collection of cameras," he continued, indicating a number of cameras on a shelf above his desk. "Then about two years ago, I came across this website that publishes photos taken by voyeurs and amateur photographers and I really got into it. They run monthly contests and I've already won a couple of them. This album contains some of my best efforts. What do you think?"

"They're great! But how do you get so many girls photos?"

"Some of them are taken secretly using a telephoto lens, or even a camera concealed in a bag for upskirt photos, and others I talked into posing for me promising to share any prize I won. Lots of times they got a bonus – six inches of hard dick just where they like it!"

"These are really good!" Jack exclaimed as he continued to leaf through the thick album, stopping every now and again to take a longer look at a particular photo that caught his attention.

"Are they making you horny again?" Tim asked mischievously.

"Yes, you could say that," Jack replied.

"Let me show you my favorite," Tim said, taking over leafing through the album. "Here, look at this one," indicating a photo of a lovely young woman of about 20, with long blonde hair and a pair of beautifully shaped breasts. She was posed lying on her side with her legs slightly parted, giving just a hint of her pussy below a neatly trimmed patch of pubic hair. "Wouldn't you like to fuck her?"

"Hell, yes," Jack replied, "but what chance is there of that?"

"Maybe, just maybe, I can help you out with that," Tim chuckled, "but I can't promise for sure. But one way or another, I promise you I'll get you laid somehow before the weekend is over!"

Jack doesn't reply, but his stomach does a complete somersault at the thought that he might soon fuck a girl!

Just then, they hear a car in the driveway and shortly afterwards the slamming of a car door, followed by the slam of the front door. A female voice calls out, "Tim! Tim! We're home!"

"That's mom," Tim explained. "Come on, let's go for that burger!" He carefully locks away his collection and they go back down to the kitchen.

"Hi mom!" Tim said, grabbing his mother in a bear hug.

"Tim, Tim, take it easy!" she said, laughing.

"Mom, meet my friend Jack from school," Tim continued.

"Hi, Jack," Mrs. Howard said, smiling at him. "Welcome to our home!"

"Glad to meet you, Mrs. Howard," Jack stuttered, mainly because she was a very beautiful woman with long blonde hair and a stunning figure, looking much younger than the mother of a nineteen year old should. Jack estimated that she would be no more than in her mid-thirties, much younger than his own mother. She must have had Tim at a very young age, he thought to himself.

His thoughts were interrupted by Tim asking, "So where's dad?"

His mother replied, "He had to go on a business trip for the weekend – some kind of seminar, I think. I just dropped him at the airport. I have a surprise for you, though. When I dropped him, I picked up someone else."

"Oh, yeah? Who?"

"You'll never guess!"

"OK, OK, I give up! Who was it?"

A female voice piped up behind them. "ME!"

The boys spun around and Tim yelled, "Sis! What are you doing here?"

Jack couldn't believe his eyes. Standing before him in all her beauty was the girl in the photo! The only difference he could see was that this time she was fully clothed! Her T-shirt clung tightly to her shapely breasts and her jeans clung equally tightly to her hips. His stomach did double flips this time and his mouth dropped open.

She responded to Tim's question. "We have a long weekend off between exams so I decided to come home. Any objections?"

Tim stepped forward and gave her a big hug, lifting her off her feet. "Not at all. You know I'm always glad to see you, Sis!" Suddenly Tim remembered Jack was there. "Oh, please excuse my bad manners. Sis, this is Jack, my friend from school. Jack, this is my sister Toni."

Jack stepped forward and shook Toni's proffered hand. "Good to meet you, Jack," she said.

"Likewise, Toni," Jack mumbled, still in awe of her beauty and hypnotized by her baby blue eyes.

"We were just going out for burgers. Want to join us, ladies?"

"OK, but I'm driving!" Toni replied.

"How about you, Mom?" Tim continued.

"No, that's OK, Tim. I'm heading for a hot bath and then off to bed with a good book. You kids go ahead and enjoy yourselves."