Chapter 1: Jefferson Academy

Caution: This Coming of Age Sex Story contains strong sexual content, including mt/ft, mt/Fa, Teenagers, Consensual, Fiction, First, Oral Sex, Slow, Violent, School, Prostitution, .

Desc: Coming of Age Sex Story: Chapter 1: Jefferson Academy - Anthony Giovanni, aka Little Tony, is going to be a high school senior. His mother has always protected him from the family business. She wants to make sure at least one son has a normal life, or as normal as is possible. When his older brother disappears, he is expected to step up and learn the darker side of what they do. Coming of Age story where he is forced to grow up much too quickly. 2015 Clitorides Awards Winner for Medium Sized Erotic Story / 2nd place for Author.

"Anthony Giovanni, get up! You're going to be late for School."

I cracked my eyes and saw Maria, my grandfather's housekeeper, giving me a mock stern look. I knew she wasn't upset with me, but she did like to mother me.

"You better get out, unless you want a show," I teased her.

I heard her mumbling it would be good to get rid of me as she left. Getting rid of me she was as I was leaving to attend Jefferson Academy, today. It would be good to be around kids my own age, again. I had been trapped on my grandfather's estate for the summer. Not that I wanted to go home. It was too dangerous.

My father is Alphonso The Bull Giovanni. Last spring, my eldest brother, Al Jr., went missing. No one would tell me what happened. This wasn't unusual, because I wasn't old enough to know my family's business. In the weeks that followed, we had a lot of new guys around the house. They didn't bother to keep quiet around me. I was able to piece together that a Hispanic gang had kidnapped my brother.

Right before school had let out for the summer, I was whisked away in the middle of the night to come live with my Grandpa Anthony Giovanni. He had an estate in northern Virginia. I was named after my grandpa, and the family called me Little Tony or LT. My older sister Pia, and my mother, had gone to live with my Grandpa Dino Ferreti in Italy. I missed them a lot.

My grandpa's estate sat on one hundred manicured acres, and he raised thoroughbreds. Unfortunately, I wasn't allowed to visit outside the inner compound while the troubles were going on. I was appalled that my grandpa didn't have internet access, nor even a phone in his house. When I complained, he gave a vague answer about the need for security.

So what is a boy of seventeen supposed to do all summer, cooped up in his grandpa's estate? Go crazy! You can only lounge around the swimming pool, or play eight-ball with yourself in the game room, so many times. I guess I can say I have a killer tan, and I could probably make money as a pool shark.

So when grandpa told me I was going to boarding school, I was ecstatic. I think his feelings were hurt, but I wanted out of this place.

I hurried out of bed and got dressed. I had packed last night, so I was ready to go. The only thing I didn't like, was I had to wear a school uniform: khaki pants, white button down shirt, blue and gold tie and a navy blue jacket with the Jefferson Academy logo on the breast. Maria had insisted on cutting my hair short, so I would be taken seriously. I looked at myself in the mirror, and was pleased. Maybe I would get a girlfriend this year.

I went downstairs and found my grandpa in the dining room, reading his morning papers. I saw he had his usual hardboiled egg, dry toast, and half a grapefruit. I was respectful of his morning routine, and sat down beside him. Maria came out with bacon, French toast, and a big glass of milk for me.

While I was eating, Steven came in and whispered something to my grandpa. Steven was the go-between for grandpa and the outside world. My grandpa was very rarely ever talked to directly.

"Excuse me, Tony. I have a matter to attend to," Grandpa Tony said.

"Of course, Grandpa."

When he left, Maria came in and sat down beside me. This NEVER happened. Grandpa was very strict about certain things. Mixing with the help was one of them. It just didn't occur! Of course, I knew he was full of it. I suspected that he and Maria had been lovers for years. My Grandma Rosa passed away before I was born. Maria had been with him for as long as I could remember. I was just happy Grandpa Tony had found such a fine woman for companionship.

"Tony, your grandpa wanted you to have this," she said as she handed me an envelope.

It must have had five-thousand dollars in it. I looked up and shook my head. My grandpa would never be seen passing cash, even to his own grandson.

"I can't accept this. Where I'm going, I won't need money. Jefferson Academy will have everything I need," I said.

I knew this was what I was expected to say, since my father had taught me well. I also knew I would accept my grandpa's generosity, and never mention it to him.

"He insists you take this for incidentals. If you need more you are to tell Steven."

"Thank you, Maria. I'll remember," I said as I pocketed the money.

We heard my grandpa coming back. Maria nodded to him, and then gathered my plate and left us alone.

"I don't want you leaving school grounds until the troubles are over. Remember where you come from. Make me, and your father proud," he said, and then shook my hand.

I knew I had been dismissed. I walked out front, and found a Town Car waiting for me. There was a driver, and a security woman in the front seat. As we drove down the long drive to the front gate I gazed out over the park-like setting, and looked forward to whatever was to come.


Jefferson Academy was known for two things. It was an outstanding college preparatory school, and it was where the best-of-the-best went to school. The school grounds were located in Alexandria, Virginia on the banks of the Potomac River. It had a long history as the place to send children of Senators, Congressmen, and Diplomats. It also attracted security conscious wealthy people. A surprising number of children in my family's businesses also went to Jefferson Academy.

There was an unwritten understanding that the children of family members would not be touched at the Academy. Even the Hispanic gang, who had my brother, wouldn't dare to break that trust. Every family would turn on them. If I wandered off school grounds, though, I was fair game.

We pulled up to a security checkpoint that would have made the Pentagon proud. They thoroughly checked our credentials, and then our car, before allowing us on the grounds. We pulled up to organized chaos. Our car was met by one of the faculty, and the driver was instructed where to take me. We drove around the side to Hensley Hall. An employee came to the car with a cart.

My security woman got out and scanned the area, before opening the back door. I had been trained not to exit the car until I was given the all clear. A girl came rushing up to the car, and the door was slammed shut. I watched as my security woman stopped the girl from approaching. I jumped out of the car.

"Get back into the car!" I was ordered.

"She's just a student," I said as I was pulled back in by the driver.

I don't think I would have jumped out if she hadn't been good looking. I took in the school uniform, and found I got a little rush seeing her dressed like that. I had been without internet access all summer ... The only women I had seen, were my grandpa's staff. The security gal was the youngest of those, and she was in her mid-thirties.

Things were tense for a moment as security appeared out of nowhere.

The young girl was released, and she brushed herself off. I was allowed out of the car.

"I'm so sorry," I said as I rushed up to her.

"No, I know better. At least she was gentle."

I got a closer look at her, and she was cuter than I first thought. She had long blonde hair and dark blue eyes I could find myself falling into. Her legs looked great. I could see a hint of what her jacket was hiding and I was impressed. I took a deep breath, to push down my hormones, and gave her a winning smile.

"I must make it up to you. I'm Anthony Giovanni, my friends call me LT," I said as I extended my hand.

"Jennifer Hensley," she said taking it.

"As in Hensley Hall?" I asked.

She turned, and looked at the sign on the building, and smiled. I liked it when she smiled. I wanted to see her doing that while she was around me.

"Yes, my father went to school, here. If you donate a bunch of money they'll put your family's name on a building. Shall we find your room, LT?" she asked.

"I take it you're the welcome wagon?" I asked, and indicated for her to lead the way.

My driver had loaded my cart with my belongings. The academy employee followed us into the lobby. I was given my room key, and orientation packet. We took the elevator to the top floor. Down the hall I saw most of the students were already moved in. We found my room, 414, and it was locked. I opened it to find my roommate had not arrived yet.

I was pleasantly surprised at how spacious the dorm rooms were. There were two queen sized beds, an old couch, and two nice desks. I looked at the mattresses and they had mysterious stains on them. Jennifer wrinkled her nose.

"Boys are gross," she said.

"Can I get a new mattress?" I asked.

"Yes, but you will have to buy it yourself. Charles, can you get LT a new mattress?"

"Yes, ma'am," our helper said. "May I help you unpack?"

"Thank you, that would be very helpful," I said.

Jennifer, Charles and I put away everything I had brought. It took all of ten minutes. I got some money out of my envelope, and gave it to Charles for his help. Jennifer saw my stash.

"We need to decorate," she said, taking my money.

"I can't leave the grounds," I told her.

"That's okay, I'll take care of it," she said.

I hadn't gotten a bad vibe from her, so I let her take the money. Heck, her name was on the building. She didn't need to rip me off. She and Charles disappeared, and I pulled out my orientation packet. In the packet, it said there were tours of the campus on the half hour. I looked at my watch. If I hurried, I could make the next one.


The tour had been informative. Jefferson Academy had three dorms. Hensley Hall was coed, with boys and girls on different floors. Wexley Hall was all boys, and reserved for athletes. Fairly Hall was all girls. There were underground tunnels you could take to all the buildings. This would come in handy when there was bad weather, but there were no excuses for not getting to class on time!

The grounds reminded me of a small New England College. There was a lot of green space, with mature trees, and ivy growing up the stone faces of the buildings.

I was disappointed to find Jefferson Academy didn't have a football team. They played lacrosse, soccer, volleyball, tennis, swimming, crew, and sailing. For the intellectuals they had chess, and debate teams. At my old high school I was penciled in as the starting tailback this year. I had hoped to play at this new school. Before I did anything I would need to get word to my grandpa, and see if I could compete. I knew games would be played off campus.

I was going to be a senior, so I ignored the freshmen on the tour. I noticed some of the freshmen girls checking me out, but they all looked so young. I also couldn't get Jennifer out of my head. I wanted to see where that went, before I started poaching freshmen.

I was hungry. I got out my map, and found the cafeteria. I looked over the selection, and decided on a grinder. I was impressed! They made the sandwich to order. It was too nice a day to be inside, so I took my sandwich and found a nice tree to sit under, to people watch. Once my stomach was full, the warm sun took its toll on me. I must have fallen asleep.

"Drool much?" a girl's voice asked.

I opened my eyes to see a smiling couple looking down at me. She was a cute blonde, and he was a good looking black boy.

"Uh," was my intelligent response.

"Bret Jacobs, and this is Harriet Smyth," he said holding out his hand.

I stood up as my brain registered they had accents. Harriet's sounded like she was form the UK. Bret sounded Scandinavian.

"Anthony Giovanni, call me LT. I must have needed a nap," I said, as I shook their hands.

"My friends call me Hattie."

We talked for a few minutes, agreed to meet at my room, and then go to dinner. Hattie and Bret were also new students, and looking to make friends. I was glad not everyone already had their own group they hung out with.


I walked to my room, and found my old couch in the hall. I had to make way as furniture was being delivered. What had I done by giving Jennifer free rein to decorate my room? I walked in to find she had two assistants, who were directing the workmen. They were both cute girls my age.

"There you are. Come in, and I'll show you what we have done," Jennifer said with a big smile.

It didn't look like the same room. I just made a slow circle to take it all in. Three things caught my eye right away. I now had a dorm sized refrigerator, and a microwave. There was a flat screen TV on the wall. What made me smile was the cappuccino maker. The girls had gone with a paisley and plaid motif. I was happy to see they were hanging black-out curtains that matched the bedspreads. I guess I was also decorating my new roommate's side of the room, too.

The beds were a smart design for the storage challenged dorm rooms. They had drawers underneath. They had found a large oriental rug, so we wouldn't have to wake up, and step onto the industrial tile flooring. In the seating area, they had found a leather couch, and two plaid side chairs. They purchased lamps for our desks, and artwork for the walls. I was awestruck with what they had accomplished in such a short time.

"Wow, I don't know what to say."

"How about you'll take us to dinner," Jennifer suggested.

"Absolutely," I agreed.

"These two are Nancy and Kendra."

Nancy had red hair and looked familiar. We caught each other looking, and we both smiled. I, at least, liked what I saw. She had green eyes that were confident. Her expression almost dared me to do something. I purposely let my eyes drop and take in her body. She had everything in the right proportions for my teenage lust. She might not be as stacked as her friends, but I could tell she had a killer little butt. I looked back up, and she had an amused expression on her face.

Kendra I knew, once I got a good look at her. She was Kendra Bianco, the daughter of Nicholas Nicky Bianco, the head of the Bianco family. Our families were rivals, but we had seen each other at family gatherings. Kendra was a classic Italian beauty, dark brown hair and eyes. More curves than a girl her age should have. I'd had a secret crush on her for years, but she had always seemed unattainable. She smiled when she saw the recognition in my eyes.

"Little Tony, fancy seeing you here," Kendra said.

"Likewise," I said, suddenly becoming very formal.

It wouldn't be prudent to have Kendra in my dorm room, no matter how innocent our interaction was. She got a big smile on her face when she realized my change in demeanor. She knew the rules. If there was even a hint of impropriety, either we would be headed down a wedding isle, or there would be bloodshed. You didn't mess with the jewel of the Bianco family.

My problem was she was my type, in spades. My mother intended me to marry a good Italian girl. If I had a choice, I agreed with my mother. I could see a match being made with Kendra Bianco. I would be a willing participant if it ever happened.

"You were always the good boy. I bet you make your family proud," she said, and then invaded my personal space. She put her mouth to me ear. "If you ever feel like being bad..."

"Kendra!" I hissed in her ear. "We can't play games."

"Who said I was playing?" she asked as she blew her hot breath on my neck.

She saw me shudder as she stepped back. I had an obvious problem.

"I'm confused. Why do you call him, Little, Tony?" Nancy asked.

All the girls looked down, and I about died of embarrassment. Thankfully Hattie and Bret showed up. They were also impressed with the work the girls had done. I was glad to get out of my room, and to the cafeteria. I teased them that I was buying. Of course they weren't going for it. We all had room and board, so our meals were pre-paid.

The cafeteria was a step above what I was used to. They had a lasagna that was passable. Someone knew how to cook. All that was missing was a glass of red wine.


After dinner Jennifer grabbed my arm, and told everyone we would see them at breakfast. She guided me back to my room. I saw Kendra and Nancy giving me looks. Jennifer was staking her claim, and I don't think the two of them were happy about it. I was just happy to have a girl want to spend time with me.

"Let's get out of these school clothes," she said.

She went into my closet, and came back out in a pair of my shorts and a t-shirt. I went in and changed also. She patted the couch, and had me sit next to her. I was feeling my inexperience. Jennifer was more than I knew how to handle.

"I don't..." I started, but she shushed me.

Jennifer leaned in and we kissed. I had kissed a couple of girls, so I relaxed. We took our time getting to know one another. I think she got impatient, and straddled my waist. I found my hands on her butt. She seemed to like it when I rubbed her firm cheeks.

I became rock hard as she began to rub herself up and down my bulge. When she stuck her tongue in my mouth I thought the top of my head was going to come off. I broke our kiss. I was going to burst at any moment, and I could tell there was no stopping it.

"I'm going to cum," I said.

I about passed out when she pulled the front of my shorts down, and bent down as she engulfed my dick. I shot off like a roman candle. Jennifer began to bob up and down my shaft making my toes curl. Why hadn't I been doing this before? This was a hundred times better than beating off. I sagged back onto the couch when I was done, and I needed to catch my breath.

Jennifer grasped my member, and stroked it to keep me from going completely soft. She cuddled up next to me, and kissed my neck. I put my arm around her and enjoyed what she was doing to me.

"That was my first time," I admitted.

"I would never have guessed," she said, with a giggle.

She could tease me all she wanted. I had gotten my first blowjob, even if it was for less than two minutes. I would take what I could get.

We were both startled when there was a knock at the door. I hurriedly stuffed my cock back into my shorts and went to answer it.

"Who is it?" I asked standing to the side of the door.

I had been taught to not just answer a door, and to never stand in front of it. That was how you found yourself dead.

"Steven," came the unexpected answer from the other side.

Why would grandpa's go-between be here? This couldn't be good news. I opened the door, and Steven was standing next to my second cousin, Gino Federico. I stepped back to let them in. Steven and Gino scanned the room, and saw Jennifer looking embarrassed on the couch. Gino was already working for the family. I was more nervous when I saw him.

"Gino, Steven, I would like to introduce you to my new friend, Jennifer," I said.

"Good evening, Jennifer. Would it be possible if you saw LT tomorrow? We need to get Gino moved in, and I need to talk to him," Steven said.

"I had a wonderful evening," I told Jennifer.

She gave me a kiss, and grabbed her clothes and left. Gino gave me a knowing smile, but Steven was all business. I don't think much surprised him. A teenage boy with a girl in his room was not even going to register.

"Gino is going to be your roommate. Gino, take your time, and go get your belongings," Steven ordered.

After Gino left, Steven put his finger to his mouth to indicate I should be quiet. He pulled out an electronic device, and checked the room. Then he told me about their trip, and he showed me the gauge which indicated there was a bug in the room. It was attached to the new lamp on my desk. It was clever they had made it voice activated.

Steven took it out of the room, and planted it in the boys' bathroom. This would give them something to listen to. When he came back, I smiled.

"Kendra Bianco helped decorate my room."

"Yes, we knew she was here. I'm surprised they would bug your room. Let's not jump to any conclusions. It could have been one of the delivery people."

He was right. Why invite trouble with the Bianco's? While we were rivals, we worked with them when needed.

"Why is Gino here? Didn't he graduate from high school a couple of years ago?"

"Your grandpa has decided you need to start being a part of the family business."

I rocked back into my seat. The only reason they would do that was if they thought my brother was dead. He was my father's successor. I was supposed to run the legitimate end of the business once I got my MBA. Steven could see I had put it together. He just gave me a sad nod. I had to take a deep breath to get my feelings under control.

Al Jr. and I had never been close, as he was twelve years older. Actually, he was a homicidal asshole. He had threatened to kill me on more than one occasion. I had always taken his threats very seriously. I was more concerned what this meant for me. I prayed nothing had happened to my father. I wasn't ready to run things.

"So, why is Gino here?" I asked again.

"He will run your organization. Gino's been assigned to be your go-between. We're going to start you off, easy, a little bookmaking and prostitution. Gino knows what to do, and how to keep you clean," Steven said, and then pulled out an envelope. "Here is seed money to get you started."

I knew better than to open it while Steven was here. I would need to find a safe place for the cash. I knew it was futile to refuse, if my grandpa had ordered it. I would need to be careful, because this was not my family's territory. I trusted that my grandpa had made arrangements to allow me to do business here.

This would be a good for Gino. Go-betweens were highly valued. Only the most trusted were ever given the opportunity. This would also give him a chance to be a good earner. There were a handful of positions within the family who got a percentage off of the work of others. The go-between was one of them. He was not expected to hit the street and do the work. He was expected to manage those who did. He would need to find people to run the prostitutes and do the book.

Gino knocked on the door, and we helped him unload his first load of stuff. He left, so Steven and I could talk some more.

"Does this mean the troubles are over?" I asked.

"No. Things are escalating. We demanded proof-of-life and were declined. We must assume the worst. I hate to say this, but your life just became much more dangerous. You are the only direct line male descendant. Your grandfather would like to arrange a marriage to help protect you. Your mother put her foot down, and said you would be allowed to marry for love."

I knew my grandpa. If he decided something my mom was not going to stop him. I wasn't ready to get married. I had just had sex for the first time. I planned on doing that many times before I said my wedding vows. Maybe Jennifer could become my mistress, if I got married.

"I have an unexpected problem," I said.

"Is this something you need help with?"

"Yes, I need someone to teach me what to do with a woman," I said.

To his credit, Steven didn't even crack a smile.

"I'll arrange a tutor."

Gino was made aware of the bug. He went to the bathroom, and retrieved it. It was put back on the lamp where it was found. We didn't need them to plant another one. If we knew it was there we could act accordingly. It was for the best. It would give us the opportunity to practice security. At some point, it might be the Feds doing the bugging. I had to learn to guard what I said at all times.

I decided I didn't need to be holding the money. I gave the envelope to Gino, and made sure he put it into a new envelope. I didn't want my finger prints on anything. I trusted Gino to keep track of the money. If I ever suspected he had betrayed me, I would have to deal with him. I hoped that day never came.

After Gino was settled, I suggested a walk around campus to help get him acclimated. When we were safely outside I began to interrogate him. He knew things I needed to know. Always before, I had been kept at arm's length from any family business. It was an agreement my father had made with my mother. He got Al Jr. to take over, but I was to be left out of the gray areas. She couldn't live with both sons potentially living behind bars. She wanted a normal, or as normal was would be possible, life for me.

What I found out, wasn't pretty. The Hispanic gang was targeting our businesses. Everyone thought my brother must be giving them information. I shuddered to think what they must have done to him to force him to reveal information about the family. I might not like my brother, but he was still family.

The day after the Hispanic gang had failed to provide the proof-of-life that had been requested, the gloves had come off. There was a rumor that my brother was alive and cooperating more freely than we thought possible. My father felt it was a misdirection meant to unnerve us. For my family's sake, I hoped the rumors were false.

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Story tagged with:
mt/ft / mt/Fa / Teenagers / Consensual / Fiction / First / Oral Sex / Slow / Violent / School / Prostitution /