John C

Jackie

Jackie was bored. He had played all the video games on his Xbox. Alone. Being a rich kid didn't necessarily mean having lots of friends… real friends. Those he know outside of the snobbish Candlestone Academy for Boys where he spent most of the year were only interested in being invited over, to play video games, use his large swimming pool, or horseback ride on one of the horses. Beyond that, he never heard from them. He wanted someone just to be a friend. Sadly, every time he called one of the local boys to invite them over, the question were always, "Can we play video games, can I bring my swim trucks, can I go horseback riding?"

Everyone's parents at the boys' academy, including his, were rich. Large mansions and estates, private jets, vacation homes around the world, always traveling here or there for business conferences and the like. They were seldom home and not for much time. Those with boys sent them to private schools where strict protocol was observed. Each boy was being educated to be ready to enter their father's business and eventually take over, keeping it within the family. Strangely, Jackie wasn't interested in such a life. But he never said anything to anyone.

Jackie was 11 years old, a handsome blond-headed boy, who although hated his time at the academy, excelled in all his studies. His professors would text his parents heaping praise on how well their son was doing.

"I can't wait until you graduate and join my firm, his father would say to him. "One day I want to the company to be renamed 'Livingston & Son Inc." Jackie would smile at his father's dream, but really had no desire to be part of that world.

What he hated the most at the school was the forced social activities planned for the boys. All wore suits and ties and went to functions where their female counterparts awaited. Soft dancing music was played; hands barely touched body as couples slowly shuffled across the wooden dance floor. Punch, of course, was the only beverage allowed. There were enough chaperones eyeing every movement to insure no inappropriate behavior ever occurred. Nine months of the year this went on. Jackie hardly seemed to know his parents. He was an only child.

Even during summer break his parents had to be here or there and hardly ever home. "Miss Tillwater will see to your every need sweetie," his mother would say before she and dad would leave on another extended trip.

Jackie hated Miss Tillwater. She was a 50ish year-old crab according to him. She was there when he was born and looked after him; bathing, feeding, changing diapers. Although he was now eleven and considered himself too old to be coddled, he suspected that the old biddy was always trying to take a peek at him when he showered to see how much he had grown over the years. She was always staring at him when he wore his speedos and took a swim. He complained about her to his father.

"Son, you're imagining things. Miss Tillwater has been with the family for 25 years. Instead of complaining how she looks at you, you should feel complimented at how she sees a baby boy she took care of grown into a fine-looking boy."

"Dad, I'm bored. You and Mom are always away. I have no real friends. I don't know which is worse, here or at the academy."

"Jackie, you know your mother and I are building a successful business that we hope we can one day turn over to you. We're sacrificing the time we could spend with you so that when you grow up and take over, others will run day-to-day operations and you can spend more time with your wife and kids."

"I don't care about the business. I want you and Mom to stay home and spend more time with me."

"Jackie, listen. You have everything money can buy. If you need something, buy it. Whatever it is that will make you happy. In the meantime, we'll try to arrange our schedule to spend more time here with you."

And with that, his parents once again left for what would be a very long trip to various cities in Europe. It was then that Miss Tillwater came into the room. "Jackie, why don't you go take a swim. That always relaxes you." The boy just ran out of the living room and upstairs to his own bedroom. That dirty old bitch just wanted to see as much skin as she could he told himself. He plopped on the bed, sad that his life couldn't be like any other normal boy.

Reflecting back on the academy, the only distraction from the day-to-day routine was shower time. Young 10, 11 and 12-year-old boys would shower together and there were always little games like grabbing at another boy's cock and/or balls. This was one of the few times Jackie smiled. Even though these games were sexual, it allowed him to be himself. He knew he had a good-looking body for a boy about to enter puberty. He never really put up much of a fight if one of his classmates would hold on to his pecker for a few seconds longer as he felt it grow and stiffen.

As he lay on his bed, he felt his young cock get hard as he recalled those fun periods. If only he could enjoy such times now during the three-month vacation. Making sure his door was locked, Jackie striped naked and stroked his boner until he felt that now familiar feeling of orgasm accompanied by a small spray of his boy juice. He scooped it up and let his tongue touch it, thinking it wasn't bad tasting. Some of the boys at school told of their older brothers or the butler or gardener secretly having sex with them.

His best friend, for lack of a better term, Ryan, would share the intimate details of the encounter. "Yeah, old man Williams always liked to fuck me. He would always say what a nice tight boy pussy I had."

"Didn't it hurt?" Jackie was thinking that no way could a grown man's organ fit inside his tight little hole.

"It did the first couple of times. But once you get used to it, you want to be fucked as often as you can. Williams would say how he couldn't wait for me to go home during holidays and breaks so he could fuck me as much as he wanted."

Jackie asked himself, "Would a man want to have sex with me? Would he want to fuck me every chance he got?" The questions aroused him, but reality then set in. The estate had butlers and men to tend the outside of the estate. But he couldn't picture any of them being allowed to enter his most hallow of place. He caught a couple of the workers, like Miss Tillwater, staring at him, but he had no interest in any of the employees. So how could he find a man he could trust so be intimate with. He shivered when he thought of the consequences should such an association be discovered. He would be sent away permanently, probably disowned by his parents. If he were to take such a risk, it had to be planned carefully.

***

For the next several days Jackie pondered on the way to meet such a man that he could trust. He realized the man would have to be one who loved sex with boys. Unfortunately, you don't find such people in the Yellow Pages. So how do you find one? And of course whatever sex took place couldn't be at the estate. There were too many snoopy people who would immediately contact his parents if they suspected something amiss. Who ever he selected had to have a secluded place that offered no chance of being discovered. As the list grew longer of what he was looking for, Jackie realized the odds of finding such a man was getting slim.

A week later, Jackie decided to take a chance that wouldn't reveal what he was really looking for. He posted an ad in the local paper:

"Wanted, a young male babysitter for a 11-year-old boy. Must be willing to entertain and look after for 12 hours a day. Salary and bonus included."

When the ad came out, Jackie thought it sounded kind of corny. But soon his cell phone rang as men offered to apply for job. Jackie gave them an address in a secluded area of a nearby park. Some were skeptical of such a meeting and hung up. Others thought he was being used to have others rob them. A few were brave enough to meet him.

A couple men were old drunks looking for easy money. Some of the younger applicants reeked of alcohol and had arms covered with tattoos. Even a few were real perverts expressing desires to rape the young boy and get paid for it. As each day passed, Jackie got despondent. Maybe the ad was worded incorrectly. He certainly couldn't imply that sex would be involved. He decided one more day and that would be it. If nothing happened, he could see what tool he could find in the kitchen, garage or shed he could use as a dildo to simulate what a cock would feel like inside him.

It was late afternoon when a young man approached him at the park. He looked to be about 30 years old. Although dressed properly, Jackie could tell the clothes were old. Was this a homeless guy? "Hi, I read where you're looking for a babysitter. I'm assuming it's you that's looking."

"Yes, it's me."

"Why would a handsome young boy like you want with a babysitter? From your clothing I would suspect you come from a wealthy family."

Jackie looked hard at the man. He was handsome, a clean-shaved face. Although the clothes looked old, the boy could tell the man took pride in himself. "My parents are away all the time. I have no brother or sister. I'm home from summer vacation and I'm bored."

"Don't you have any friends?" as Jackie shook his head no.

"So how do you want a babysitter to entertain you for twelve hours a day?"

Jackie took a chance. "I want to learn new things."

The man didn't say anything for a while. When he did, he just introduced himself. "My name is Jeff."

"I'm Jackie," as the two shook hands.

"I'll be honest with you. I've been watching the men who have approached you applying for the position. I was glad to see you turn them down. Whatever special reason you have for needing a babysitter, those men definitely didn't fit the bill. I'm not sure if I do."

Jackie wasn't sure what to say next. He didn't know the man well enough yet to state what he was looking for. But he thought that if he were he, he would feel comfortable in whatever they did. "Are you married Jeff?"

"No, never have been. I didn't fit in to what society wants of me."

"You're not homeless, are you?"

This got a laugh from the young man. "Thankfully no. I have a small travel trailer on a private piece of land my father willed me. That was all. I do part-time work whenever I need grocery money."

"If you were to baby-sit me, could we do it at your place?"

"Now that's an interesting question from a what, 11-year-old boy? I guess we could. Why, your mansion doesn't have enough rooms?"

"This has to be private. No one can know I'm with you and what we're doing?"

Jeff stared at Jackie for a long time. "What will be doing that's going to be so private?"

Jackie squirmed on the park bench. He was hoping Jeff could put two and two together without him saying exactly what he wanted. Jeff then smiled at the boy, sensing his nervousness. "Are we going to plan a bank robbery?" This caused Jackie to laugh.

"No, no bank robbery."

"Well, let me see, what would a lonely 11-year-old boy, who probably has hormones raging within him, want to learn about?" Jackie stared hard at Jeff hoping he would just say it. "Would this boy want to learn about sex?"

"Yes!" Jackie almost shouted, and then lowered his voice. "Please?"

"Now 'that' is a big babysitting job, and a dangerous one too." Getting a questioning look from the boy. "You know it's illegal for a man and boy to have sex together. I may be poor, but I'm free. Last place I want to be is in prison being Bubba's fuck toy," getting a laugh from Jackie.

"It will be just you and I. That's why I wanted it to be at your place. I want you to teach me everything about sex. I heard the boys at school tell of how men use them. I want you to use me." Jackie waited, wondering what reply he would get.

"Jackie, you don't know anything about me and I know very little about you. I'll tell you something about myself. I'm gay. Knew that since I was ten. I had sex with a couple of men when I was a young boy of 11 and 12. Some of it was good, some wasn't. But I never did it with an underage child."

"You don't like me?"

"That has nothing to do with it. The little I've gotten to know you make me like you a lot. You have a head on your shoulders and you're careful before jumping in the pool. You screened all those men and realized they weren't what you wanted. I'm honored that you would trust me with something so intimate as a sexual relationship. It's not every day a handsome boy like you asks me to have sex with him," getting another laugh from Jackie.

"I'll pay you a good salary. I have my own bank account."

"Well, the money is always welcomed. My father expected me to forage on my own as he felt he had done enough by giving me some land. Now I'm a believer in recycling. But it takes a lot of cans and bottles to make enough money for a good meal."

"I'll buy lunch every day."

"Tell you what Jackie. Let's have one of those lunches right now. I'm hungry. We can talk about this more and see if this is what is right for us."

It took two 'lunches' over two days before Jeff took Jackie to his travel trailer. It was a newer 35-foot model, specious and comfortable. "Think you'll enjoy running around naked inside here?" getting a large grin in return.

"Now before we do anything, I want to show you something. This will be your last opportunity to change your mind and forget this sex education you want so badly." Digging inside a drawer, Jeff pulled out a flash drive. I downloaded this from the Internet. It's illegal to have these. So once I show these videos to you, I'm wiping this clean. It's about an hour of man/boy sex and the various things they do to one another. This is what you and I will do. If after you see it, you want to continue, we'll start. If you change your mind, you go home and we pretend we never met each other."

"Deal! Okay. I'm ready."

Hearing the boys at the academy tell of their sexual experiences with those older than them, and seeing actual acts on a video are two huge differences. Jackie watched men making out with a boy, sucking their cock and balls, licking their assholes, giving blowjobs, and eventually sliding their large cocks deep inside. Some of the boys in the video had a hard time adjusting to the invasion; others took it with a smile. Then the roles were reversed as boys made out with the man, filling their mouths with large cocks and swallowing copious amounts of cum. Unaware of what he hand was doing, but noticed by Jeff, Jackie was playing with his evident hard erection through his pants. At the conclusion of the show, Jeff immediately loaded software to wipe any evidence that porn was on the flash drive.

"Well, what do you think? Now that is real man/boy sex. Not these quickie stories maybe your school friends shared with you. It's called man/boy sex because the man is in charge. The boy is learning, but it's to please the man. Yes, he gets some pleasure out of it too. But his main purpose to make sure his man is satisfied."

Jackie was quiet for several moments reviewing in his mind what he just saw on the screen. "I'll do whatever you want. I belong to you twelve hours a day for the summer."

"Are you absolutely sure? And you're sworn to secrecy till the day you die."

"Till the day I die, I swear."

"All right my young boy toy. Come here and let me undress you and see what I'm going to enjoy for the next three months." It wasn't long before Jackie stood totally naked before his new adult friend. "You know this is a strange arrangement?"

"How?"

Well, usually it's the man looking for a boy to have sex with. You're probably the first boy who looked for a man," getting a smile and then letting out a small moan as he fell his cock and balls fondled.

The End