Stupid Boy Tie-In Box Set
G. Younger
Stupid Boy: Tie-In Box Set
Five Plus Books with Crossovers to Stupid Boy
Date: August 26, 2023
Copyright ©2023 G. Younger
ISBN-13: 978-1-955699-07-5
Author: Greg Younger
Editing Staff: BlackIrish, Askepot, BaoChou, hikewithapack, jamien42, Jim7, Tangoran, Zom, and Bud Ugly.
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All characters depicted in this work are fictitious. Any resemblance to real persons, living or dead, is purely coincidental. Names, characters, places, brands, media, and incidents are either the product of the author’s imagination or are used fictitiously. The author acknowledges the trademarked status and trademark owners of various products referenced in this work of fiction, which have been used without permission. The publication/use of these trademarks is not authorized, associated with, or sponsored by the trademark owners.
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Preface to Crossovers
I began writing for fun. Memorial Day weekend of 2014, I sat down at a keyboard and started a short story about a guy and a gal. Come Monday evening, I'd written almost 200 pages.
That story ended up being Stupid Boy. I was lucky from the beginning because Rev. Cotton Mather, famous for writing the Playing the Game trilogy, told me I could tell a story but needed an editor desperately.
I began writing Stupid Boy, thinking I needed to learn how to write. The goal was to eventually write the first book I thought of loosely as Star Academy. From day one, my goal has been to learn my craft, and it helped that you were not shy in sharing your opinions of my writing.
Some were very helpful and said stuff like: “Just finished reading your book and found a couple of errors, but I forgot to write them down.”
Then some came out of left field and compared me to other writers. For Sell Anything on Craigslist—Mark Twain. For My Intended—Ann Rice. For Conclave—Colin Dexter (he wrote the Inspector Morse series). And many others.
I shared this with my editors and laughed at myself because I am not near the writer they are. Then one of them pointed out they were all dead, so I probably could outwrite them now. I feel guilty admitting they are right … I can probably outwrite a dead person—IF my editors are on their game.
Anyway, back to Stupid Boy, now continuing as A Better Man. What was planned as a short story has turned into an epic series with many volumes and more to come. I also write other books between each Better Man offering, if for no other reason than my sanity. Some are just short stories, such as the aforementioned My Intended. Others are novels in their own right, such as Conclave and Sell Anything on Craigslist.
Sometimes, characters from outside the Stupid Boy/Better Man stories cross over and show up in this series. And occasionally, a character from Stupid Boy or A Better Man will show up in one of the others.
I realize that some readers have read all of the books as I’ve posted them (thank you), but some have not. This book is to provide the backstory for these crossover characters. If you’ve not read these before, well, this will hopefully fill in some holes and give you a more complete picture of what’s going on in our friend David’s world. And if you have read all of them, perhaps this will remind you of where some of the characters come from and what they’re about.
Each of the books included here has an added preface of its own, explaining what character or characters from the story have appeared in Stupid Boy or A Better Man.
Please note that the stories contained here have been re-edited from the originals; the plot, characters, and storyline are the same, but they’re not word-for-word identical to the original published version.
Now, before I go off on a tangent about how my job and family are more important than writing … let’s get back on track.
Table of Contents:
Part 1: Little Tony
Part 2: Pia
Part 3: Getting it Wrong
Part 4: Sister Swap: Wrong Side
Part 5: Haunted
Part 6: Other Books, Other Characters
Notes from the Author
Part 1: Little Tony
Preface to Little Tony
I wrote Little Tony while taking a break so I could get my head back into SB.
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 possible. When his older brother disappears, he is pulled into his family’s business before he’s ready. Little Tony is expected to step up and learn the darker side of what they do.
Little Tony made his debut on Stories Online in 2015 in an eponymous short story.
He was then introduced to David in Stupid Boy Junior Year Part II as a fan of David’s work in helping to put Brandon Rigby behind bars. In Stupid Boy, we learn that Tony is pushing his family into legitimate businesses. He and David become friends.
Also appearing in Stupid Boy and A Better Man are his parents, Alphonso “The Bull” and Bianca Giovanni; his sister Pia; his cousin Nicki; his business partner Kendra Bianco; his wife, Nancy, and her father, Senator Byron Wilson.
As to where this assemblage comes from, read on.
Chapter 1 – Jefferson Academy
“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. She wasn’t really upset with me, but she did like to mother me.
“You better get out unless you want a show,” I teased her.
As she left, I heard her mumbling it would be good to get rid of me. And getting rid of me she was, as I’d be leaving to attend Jefferson Academy today. It would be good to be around kids my own age again after being 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 elder brother, Al Junior, went missing. No one would tell me what happened. This wasn’t unusual because I wasn’t considered old enough to know my family’s business. In the following weeks, we had many new guys around the house, and they didn’t bother to keep quiet around me. I could 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’d been 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 Ferretti in Italy. I missed them a lot.
My Grandpa Giovanni’s estate sat on one hundred manicured acres, and he raised thoroughbreds. Unfortunately, I couldn’t visit outside the inner compound while the ‘troubles’ were going on. I was appalled that my grandpa didn’t have internet access or 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 could say I had a killer tan and 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. Since I’d packed last night, I was ready to go. Something I didn’t like was I had to wear a school uniform. That included khaki pants, a white button-down shirt, a 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 people would take me seriously. I looked at myself in the mirror and was pleased. Maybe I’d get a girlfriend this year.
I walked downstairs and found my grandpa in the dining room, reading his morning papers. He had his usual hard-boiled egg, dry toast, and half grapefruit in front of him. 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 seldom 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, and mixing with the help was one of them. It just didn’t occur! Of course, I knew he was full of it. I suspected he and Maria had been lovers for years. My Grandma Rosa passed away before I was born, and Maria had been with him for as long as I could remember. I was happy Grandpa Tony had found such a fine woman for companionship.
“Tony, your grandpa wanted you to have this,” she said, handing 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 I was expected to say this since my father had taught me well. Of course, 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’re to tell Steven.”
“Thank you, Maria. I’ll remember,” I said and pocketed the money.
We heard my grandpa coming back. Maria nodded to him, 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 shook my hand.
I’d been dismissed, so I walked out front and found a town car waiting for me. A driver and a security woman sat in the front seat. As we drove down the long driveway to the front gate, I gazed out over the park-like setting and looked forward to whatever was to come.
◊◊◊
Jefferson Academy was known as an outstanding college-preparatory school where the best of the best went. The school grounds were located in Alexandria, Virginia, on the banks of the Potomac River. Jefferson Academy had a long history as the place senators, congressmen, and diplomats sent their children. It also attracted security-conscious wealthy people. A surprising number of children in my family’s businesses attended 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 became fair game.
We arrived at the school’s main gate, stopping at a security checkpoint that would have made the Pentagon proud. They thoroughly checked our credentials and our car before allowing us on the grounds. We pulled up to organized chaos. One of the faculty met our vehicle and instructed the driver where to take me. We drove around the side to Hensley Hall, where an employee came to the car with a cart.
My security woman got out and scanned the area before opening the back door. I’d been trained not to exit the car until security gave me the all-clear. A girl came rushing up to the car, and the door was slammed shut and locked. I watched as my security woman stopped the girl from approaching. I jumped out of the vehicle.
“Get back into the car!” my security woman ordered.
“She’s just a student,” I said as my driver pulled me back into the car.
I don’t think I would have jumped out if she hadn’t looked good. I took in the school uniform and found I got a bit of a rush seeing her dressed like that. After all, I’d been without internet access all summer, and the only women I’d seen were my grandpa’s staff. The security gal was the youngest of those, and she looked to be in her mid-thirties.
Things were tense for a moment as security appeared out of nowhere.
They finally released the young girl, and she brushed herself off. The driver then allowed me to get out of the car.
“I’m so sorry,” I said as I rushed up to her.
“No, I should have known better. At least she was gentle.”
I looked closer at her; she was cuter than I first thought. She had long blond hair and dark blue eyes I imagined myself falling into. Her legs looked great, and I could see a hint of what her jacket was hiding, and I was impressed. Taking a deep breath to push down my hormones, I gave her a winning smile.
“Please let me make it up to you. I’m Anthony Giovanni. My friends call me LT,” I said and extended my hand.
“Jennifer Hensley,” she said, taking it.
“As in Hensley Hall?” I asked.
She turned, looked at the building sign, and smiled. I liked it when she smiled, and 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 his cart with my belongings. The academy employee followed us into the lobby, where a check-in lady gave me my room key and orientation packet. We took the elevator to the top floor, and I saw that most students had already moved in down the hall. We found my room, 414, which was locked, and I opened it to find my roommate hadn’t arrived yet.
I was pleasantly surprised at the spaciousness of the dorm rooms. There were two queen-size 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’ll 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’d 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; let me 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. The packet 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 was informative. Jefferson Academy had three dorms. Hensley Hall was coed, with boys and girls on different floors; Wexler Hall was all boys and reserved for athletes; and Fairly Hall was all girls. There were underground tunnels you could take to all the buildings. This would come in handy when there was inclement weather, but there were no excuses for not getting to class on time!
The grounds reminded me of a tiny New England college. There was a lot of green space, 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. This year, I was penciled in as the starting tailback at my old high school, and I’d 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 since games would be played off campus.
I was going to be a senior, so I ignored the freshmen on the tour. Some freshman girls were checking me out, but they all looked too young. Besides, I couldn’t get Jennifer out of my head. I wanted to see where that relationship would go before thinking about poaching freshmen.
Since I was hungry, I got out my map and found the cafeteria. I looked over the selection and decided on a grinder, which impressed me. They made the sandwich to order. It was too nice a day to be inside, so I took my sandwich and found a suitable 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 blond, 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 from the UK, and Bret sounded Scandinavian.
“Anthony Giovanni; call me LT. I must’ve needed a nap,” I said, shaking their hands.
“My friends call me Hattie.”
We talked for a few minutes and agreed to meet in my room, then go to dinner. Hattie and Bret were also new students and looking to make friends. I was glad that not everyone already had their own group they hung out with.
◊◊◊
As I returned to my room, I found my old couch in the hall. I had to make way as deliverymen brought in furniture. What had I done by giving Jennifer free rein to decorate my room? I walked in to find she had two assistants who directed the workmen. They were both cute girls my age.
“There you are. Come in, and I’ll show you what we’ve done,” Jennifer said with a big smile.
It didn’t look like the same room, and I just made a slow circle to take it all in. Three improvements caught my eye right away. My room was now equipped with a dorm-size refrigerator, a microwave, and a large flat-screen TV. But what made me smile was the cappuccino maker. The girls had gone with a paisley-and-plaid motif. I was happy to see workmen hanging blackout curtains that matched the bedspreads. Apparently, I was also decorating my new roommate’s side of the room.
The beds were an intelligent design for the storage-challenged dorm rooms: they had drawers underneath. Jennifer and her minions had found a large oriental rug, so we wouldn’t have to wake up and step onto the cold industrial tile flooring. They found a leather couch and two plaid side chairs in the seating area. They purchased lamps for our desks and artwork for the walls. I was awestruck by what they’d 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 confident green eyes, and 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 she had a killer little butt. I looked back up and saw her amused expression.
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’d seen each other at family gatherings. Kendra was a classic Italian beauty with dark brown hair and eyes, and more curves than a girl her age should have. I’d had a secret crush on her for years, but she’d 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 might be. She got a big grin when she recognized my change in demeanor. She knew the rules. If there was even a hint of impropriety, either we’d be headed down a wedding aisle, or there’d 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 for me to marry a good Italian girl, and if I had a choice, I would agree with Mom. I could envision a match being made with Kendra Bianco. If it ever happened, I’d be a willing participant.
“You were always the good boy. I bet you make your family proud,” she said, invading my personal space. She put her mouth to my 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, then 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 three girls looked down, and I about died of embarrassment. Thankfully, Hattie and Bret showed up at just that moment. 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 prepaid.
The cafeteria was a step above what I was used to. They had a passable lasagna, which told me 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’d see them at breakfast. 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. For my part, I was just excited to have a girl who wanted to spend time with me. She guided me back to my room.
“Let’s get out of these school clothes,” she said once we got inside.
She stepped into my closet and returned wearing shorts and a t-shirt. I walked in and changed as well. When I came out, 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’d kissed a couple of girls, so I relaxed. We took our time getting to know one another. She got impatient and straddled my waist while 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 because I was going to burst at any moment, and I could tell there was no stopping it.
“Jennifer, I’m going to cum,” I said.
I nearly passed out when she pulled the front of my shorts down, bent over, and engulfed my dick. Just as I’d predicted, 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. When my explosion ended, I sagged back onto the couch, needing 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, so 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’d gotten my first blow job, even if it was for less than two minutes. I would take what I could get.
We were both startled when there came a knock at the door. I hurriedly stuffed my cock back into my shorts as I walked over to answer it.
“Who is it?” I asked, standing to the side of the door.
My family had taught me not to 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 stood there with 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 already worked for the family, and I grew 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 for you to see LT tomorrow? I need to talk to him, and we need to get Gino moved in,” Steven said.
“I had a wonderful evening,” I told Jennifer.
She gave me a kiss, grabbed her clothes, and left. Gino gave me a knowing smile, but Steven was all business. I don’t think much surprised him, and a teenage boy with a girl in his room wasn’t even going to register.
“Gino’s 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 as he showed me the gauge, which indicated a bug in the room. Steven found it attached to the new lamp on my desk, and it was clever: they’d 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. But let’s not jump to conclusions; it could have been one of the delivery people.”
He was right. Why invite trouble with the Biancos? 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 become part of the family business.”
That rocked me back into my seat. The family would only do that 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 tell 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 Junior and I had never been close, as he was twelve years older. Actually, he was a homicidal asshole. He’d threatened to kill me on more than one occasion, and I’d always taken his threats very seriously. I was more concerned about what this meant for me. I prayed nothing had happened to my father because I wasn’t ready to run anything.
“So, why is Gino here?” I asked again.
“He’ll run your organization. Gino’s been assigned to be your go-between. We’ll start you off easy with a little bookmaking and prostitution. Gino knows what to do and how to keep you clean,” Steven said and pulled out an envelope. “Here’s seed money to get you started.”
I knew better than to open it while Steven was here. And I knew it was futile to refuse if my grandpa had ordered it. Now I would need to find a safe place for the cash. I would need to be careful because this wasn’t my family’s territory. I trusted that my grandpa had arranged to allow me to do business here.
This would be good for Gino. Go-betweens were highly valued, and 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 that got a percentage off of the work of others, and the go-between was one of them. He wasn’t expected to hit the street and do the work; instead, Gino would be expected to manage those who did. What he would do was find people to run the prostitutes and do the book.
Gino knocked on the door, and we helped him unpack his first load. He left so Steven and I could talk some more.
“Does this mean the ‘troubles’ are over?” I asked.
“No. In fact, things are escalating. We demanded proof of life and were declined, which makes us assume the worst. I hate to say this, but your situation just became much more dangerous. You’re 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’d be allowed to marry for love.”
I knew my grandpa. If he decided something, my mom wasn’t going to stop him. That said, I wasn’t ready to get married. I’d just had sex for the first time and planned on doing that many times before uttering 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.”
Steven made Gino aware of the bug. Gino walked down the hall to the bathroom, retrieved it, and put it back on the lamp where Steven had found it. We didn’t need them to plant another one. If we knew it was there, we could act accordingly. It was for the best because it would allow us 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.
After considering my situation further, I decided there was no need for me to be holding the money. In fact, it was better if I didn’t, so I handed the envelope to Gino and made sure he put it into a new envelope. I didn’t want my fingerprints on anything. I trusted Gino to keep track of the money. If I ever suspected he’d betrayed me, I would have to deal with him. I hoped that day never came.
After Gino settled in, I suggested a walk around campus to help get him acclimated. Once we were safely outside, I began to interrogate him. He knew things I needed to know. In the past, I’d always been kept at arm’s length from any family business. It was an agreement my father had made with my mother. He got Al Junior to take over, but I was to be left out of the gray areas. She couldn’t live with both sons potentially residing behind bars. She wanted a normal—or as normal as would be possible—life for me.
What he told me wasn’t pretty. The Hispanic gang was targeting our businesses. Everyone believed 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 failed to provide the proof of life requested, the gloves came off. Rumor had it that my brother was alive and cooperating more freely than we thought possible. My father felt the rumor was a misdirection meant to unnerve us. For my family’s sake, I hoped the rumors were false.
◊◊◊
Chapter 2 – School Starts
It didn’t take me long to figure out that I would need to study. These classes were much more challenging than what I was used to in public school, and I almost had a fit when they assigned homework on the first day. I thought the first day was supposed to be about greeting everyone and going over the course outline, not jumping into the deep end.
At lunch, Jennifer saw I was freaking out.
“A little harder than you expected?” she asked.
“I’m not sure I can do this,” I said.
“I know how to get you back on track,” she said.
“How?” I asked.
Jennifer grabbed my hand and led me back to my room. She unzipped my fly and fished out my member. I stood there as she dropped to her knees and began to blow me. This time I lasted all of five minutes. What had I done to get so lucky to find a girl who would blow me at the drop of a hat? Nothing like this had ever happened to me before.
“Put your dick away. We have to get to our next class.”
I was lucky because Jennifer had all the same classes I did. I needed Steven to get my sex tutor to me soon. As much as I enjoyed blow jobs, even I realized this wouldn’t last if it was one-sided.
◊◊◊
One of the requirements at Jefferson Academy was that you had to go out for a sport. They had this idea of graduating well-rounded individuals. I agree that sports teach a lot about life, like being a team player and working with others. I just had to find a sport that I liked that wasn’t too much work.
Gino and I sat down and figured out what we wanted to do. Lacrosse was too physical; it was too close to armed combat, and I had no desire to get whacked with a stick. Soccer had too much running. We checked out crew. They put us on a couple of rowing machines, and after ten minutes, I was ready to throw up. That was just insane. Sailing didn’t seem too demanding, but it looked boring. We finally settled on swimming.
Gino and I both grew up with pools and were reasonably strong swimmers. I wasn’t looking for anything to kick ass in since they didn’t play football. I just wanted to have fun.
It was all good until we showed up to swimming orientation, and they handed out swim trunks—or should I say Speedos. Gino saw my expression and smiled.
“Dude, you have nothing to worry about. Just own it,” he said.
I was more worried about popping a boner with the dang suit on.
“What happens if …?” I asked.
“…you release the Kraken?” Gino teased.
I turned about ten shades of red.
“I suggest you get your girlfriend to give you more blow jobs to control the beast.”
“Seriously?” I asked.
“Have I ever steered you wrong? You should be golden if she blows you a couple of times before practice.”
I couldn’t tell if he was bullshitting me or not. In theory, it should work. Gino hadn’t lied to me, ever, as far as I knew. Besides, if you couldn’t trust your go-between, you were screwed. I would have to talk to Jennifer about it.
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When we returned to our room, Gino checked his voicemails. We made a point of him doing it outside the room because of the bug. When he came back, he had some news.
“Cancel your nightly get-together with Jennifer.”
His smile told me I would meet my tutor tonight. That made me nervous as hell, which kept Gino amused. Jennifer didn’t believe my excuse for one moment and started giving me the third degree. That’s when Gino saved my ass: he told her to lighten up. He said he and I were goofing off and promised I would call her when we were done.
She looked at us skeptically but let the subject drop.
When I got back to my room, I couldn’t sit still. I about jumped out of my skin when there was a light knock on the door. Gino answered it and let her in.
I smiled when I saw her. If I were to guess, she was a college girl. She was my type, with her silky long black hair and dark eyes. She was a classic Italian beauty with plenty of curves, which her little black dress showed off. When I was thirteen, my family had gone to Italy, and I’d come to love how the women looked. If I were totally a male pig, I would say Jennifer was a bit too skinny for my taste. I liked a woman with wider hips and larger breasts.
“Hey, babycakes, how’s tricks?” Gino said.
She gave Gino a kiss.
“It’s been too long, lover. How come you never call me?” she asked.
“I’ve been here. This is LT,” Gino said.
“You’re a cute one,” she said to me and then asked Gino, “He gets the full treatment?”
“I don’t want him able to walk when you’re done. Take your time, and teach him well,” Gino said, then left us alone.
I got a good look at the girl in front of me. I didn’t even know her name.
“Gino has no manners. I’m Tony. I didn’t catch your name,” I said.
“April,” she said as she stepped closer to me.
“Gawd, you’re beautiful,” I said.
“A woman never gets tired of hearing that. You’re not so bad, yourself,” she said as she touched my chest.
“April, I’ve never …,” I started.
“Hush, darling. I’ll help you through this,” she promised.
She unbuttoned my shirt; I’d taken my jacket and tie off when I returned to my dorm room. Once she had me unbuttoned, she ran her hands up my stomach and onto my chest, then ran her fingernails up and down my torso.
“Tony, I’ll need to tell you things to make you a good lover. You must understand that what I say is to help you, not to be mean. Are you going to be okay with that?” she asked.
I just nodded, understanding her caution. Italian men did not like to be instructed or criticized by women. Of course, this was old-school thinking, but she was better off asking now rather than finding out the hard way later. April smiled and got me undressed. Then she took me to stand in front of a full-length mirror.
“Honey, you’re a handsome young man, but you need to get in shape. You’ll have to watch your weight even more as you get older. Now, I’m not talking about getting buff; you don’t need to be ripped. I want you to get your stamina up and work on your core. That’s the center portion of your body,” she said, pointing around my middle.
I looked at myself with a critical eye, and she was right. I had a little paunch started, and love handles. If I had them now, it would be worse when I got older. I’d been in shape when I played football and hadn’t worked out much over the summer. It showed.
“Look, sugar, the unvarnished truth is you’re a good-looking boy. If we add some confidence without adding arrogance, you’ll be a little stud muffin,” she said, then changed the subject. “I need you to tell me exactly what you’ve done to this point. Gino tells me you have some experience, so I don’t want to cover anything you already know.”
“I’ve been on a couple of dates. I kissed some girls, and they seemed to like it. The girl I’m seeing has given me a couple of blow jobs.”
“I bet you liked that,” April said.
“Yeah, I guess. I didn’t really last that long,” I said.
“How long did you last during the first one?”
“Until she put me in her mouth,” I said, blushing.
“And the second time?”
“About five minutes.”
“I’m going to give you some muscle exercises to help you with that, but I’d say the more you do it, the better you’ll get. So, what’s her name?”
“Jennifer.”
“Have you gone down on her?”
“No, we never seem to have time.”
She gave me a funny look.
“So, you kiss her, and she gives you head? Is that all you’ve done?” she asked.
I nodded.
“And she hasn’t broken up with you?” she asked.
“No, why? Is she going to?” I asked.
“Settle down. We’re going to fix this before she does,” April assured me. “I’m going to teach you a few things all boys should know but few seem to understand. You need to remember to please her first. If you focus on making Jennifer feel good, she’ll please you in return. I realize you like to get a blow job, but you might want to get her off first.”
“I feel like such a selfish prick,” I moaned.
“Buck up, stud. She seemed to want to continue to suck your dick. You have a nice one, by the way. I’ve seen a few, and you’re doing just fine,” she said.
I just shook my head. How could I be so stupid? Jennifer wasn’t here just to service my needs. If I wanted more, I needed to be more considerate.
“Now, I notice you get embarrassed easily. Have you had many girlfriends before Jennifer?” April asked.
“No. I was actually surprised she wanted to be my girlfriend. When I got here, my security stopped her from meeting me, and I figured she’d never talk to me after that. Then she volunteered to remodel my room,” I said, pointing out everything she did.
“How did your first encounter happen?” she asked.
“Jennifer invited me back to my room the first night we were here. We kissed, and she got a bit aggressive. When I said I was going to cum, she went down on me. But we got interrupted, and she had to leave.”
April looked at me with a curious expression.
“How long had you known her?” she asked.
“I don’t know, a couple of hours, maybe.”
“When was the second time?”
“Today at lunch. She saw I was stressing about classes and helped me out.”
April just shook her head.
“Is something wrong?” I asked.
“No, no … ‘gift horse in the mouth’ comes to mind, though. I would just go for it,” she suggested.
“So, this isn’t normal?” I asked.
“Kid, you might be Don Juan for all I know … but no, this isn’t normal. Most times, you have to work to get a girl to like you first. I’m sure you’ll be fine if you ever need to do that. Just be yourself.”
“Okay, but should I be worried?” I asked.
“Kid, what’s to worry about if she’s willing to blow you? Seriously, don’t overanalyze it,” April suggested.
I nodded, and she was ready to move on.
“I’m going to lead you through making out and foreplay. Let’s sit on the bed and get started. I want you to kiss me,” she ordered.
We began to kiss. At first, it was kind of getting to know each other, but then it heated up. I wasn’t quite sure what to do with my hands. After about ten minutes, April pulled my right hand to her breast, and I just put in on it and left it there. She broke our kiss.
“Gently caress and squeeze my breasts. If you do it too hard, it’ll hurt me. Think of playing with your balls. You wouldn’t want them handled too roughly, now, would you?” she asked.
“No!” I said emphatically.
I found I really loved playing with her breasts. They were like two firm grapefruits. I was amazed when her nipples became hard at my touch. Her kisses became more passionate, and she started running her hands over my naked chest.
“Undo my dress,” she said.
I reached back and pulled her zipper down, and she shrugged it off her shoulders, exposing the two objects of my desire. We began to kiss again, and I used my uninhibited access to learn every inch of her. I was surprised when she pushed my head lower, and I finally got the idea and began to suck, lick, and kiss her breasts.