Jackboy

By Fredrick Woodard Sr.

Meet Lil Free, an ambitious little boy who transforms into a ruthless robber and drug dealer on the dangerous streets of Florida. His rise to the top earns him an elite spot with the notorious Jackboys.

Driven by a desire for power and wealth, Lil Free`s descent into a life of crime leads him down a dark path where violence and betrayal become his daily companions.

As he delves deeper into the criminal underworld, the stakes escalate, and danger looms at every turn; Lil Free is forced to confront the consequences of choices.

Ambition. Betrayal. Love. Lust. Greed. Redemption? Meet Lil Free.

• Language: English
• Publisher: Spines
• Release date: Apr 7, 2024
• ISBN: 9798893831115

Book preview

Chapter One

The Beginning

BITCH STOP! Lil Free yells while trying to push Tasha off of him. Tasha is holding 9-year-old Lil Free down while sucking on his chest, putting hickeys all over his chest.

Shut up! You know you like it. They are in the den of their parent’s new home.

Tray, better known as Candy, was Tasha’s father. Sylvia, Lil Free’s mother, just got married to Candy. He bought Lil Free’s mother a new house, then moved his two kids, Chris and Tasha, into the house along with Sylvia’s two children Lil Free and his sister Clarissa. Chris and Tasha were 16 and 17, while Clarissa was 14 and Lil Free was 9. You’re supposed to be my big sister! Lil Free says. Tasha ignores him and starts to suck on Lil Free’s neck. AAHHHH! Lil Free yells, That shit hurts! His chest was on fire from the eight hickies Tasha had already put on his chest. Don’t suck so hard! Lil Free says.

Okay, Tasha says. She’s still sucking on Lil Free’s neck but not so hard anymore. How’s that? she says. Lil Free stops trying to get away and lets Tasha suck on his neck. The feeling starts to go from pain to pleasure. Lil Free feels himself getting aroused, and his lil wee-wee starts to get hard. He knows he can put it between Tasha’s legs for a wonderful sensation. A feeling that he has tried to duplicate ever since his old babysitter Na-Na, made him do it to her one night they were alone. He thought it was wonderful! He tried to do it to a lil girl in school in the coat room and got in trouble. Tasha feels Lil Free's little dick getting hard against her thigh. OOOHHH! Boy, you so nasty!

Lil Free says, You did it. Now what you gonna do about it? Tasha sits back on her feet while still sitting on her knees and looks at Lil Free. Lil Free is lying on his back, looking up at Tasha in her eyes with his hand on her thigh.

Boy, you wouldn’t know what to do with that lil thing if I told you.

Lil Free, with his other hand, rubs on his now hard, 9-year-old penis and says to Tasha, First of all, it ain’t little, and second of all, you don’t have to tell me shit! If you go in the room and take off them shorts, I’ll show you what I’ll do with this. He grabs his erection. Tasha is stunned by what this little boy just said this to her, and she’s now just staring at the little boy in front of her. She had no idea that Lil Free knew anything about sex. Now looking into his eyes, she was becoming confused and aroused. As if in a daze, she gets up and walks towards the back of the house to her bedroom. Lil Free gets off the floor and follows her. As Tasha gets to her room door, Chris, Tasha’s brother, comes out of his room.

Lil Free, let’s go play some basketball. Naw, that’s okay big bro. I’m tired. I’m about to go take a nap.

While Chris and Lil Free are talking, Tasha walks into her room and closes the door. She sits on her bed and thinks about what she’s about to do. I’m about to have sex with a 9-year-old? When she says it out loud, it sounds ridiculous to her! She then says out loud, Hell naw. She then gets up and walks to her door.

As soon as she reaches for the door, it opens, and Lil Free walks right in and closes the door behind him. He’s gone. He says. He immediately wraps his long, skinny arms around Tasha, grabbing her butt. Even though Tasha was eight years older than Lil Free, they were almost about the same height, Tasha being only a few inches taller.

Boy, get yo hands off my butt! Tasha says while pushing his hands down.

What’s up? I thought you wanted me to show you what I know?

You’re too young Free. It just doesn’t feel right, Tasha says.

Lil Free looks up at Tasha, snatches his hands off her, and says, Well then, stop sucking on me Bitch! Lil Free turns around and walks out of Tasha’s room. Leaving her standing there with her mouth wide open.

ORLANDO, FL. 1/25/86

Sylvia was sound asleep when she heard the door slam shut. She was alone in the apartment at Palm Grove Gardens. Candy, her newlywed husband of 6 months, drove trucks and would occasionally stop in Orlando on runs to see his new wife. She took on the apartment manager job in Orlando and left Lil Free and Clarissa in Jacksonville at her mother’s house. She drove from Orlando to Jacksonville every weekend to spend time with her kids. She was given a rent-free apartment for taking the job in Orlando and three times more money than her last job. So she and Candy agreed that she shouldn’t let the opportunity pass.

When she heard the door slam, she immediately sat up in bed, Ray, is that you?

Who the hell else you think it is, your lil boyfriend? Ray screamed.

Ray, please! Before she could say anything else, Candy punched her in the face and broke her nose.

Bitch I know you cheating on me! Who the fuck you have up in here when I’m not home? While Candy is screaming, Sylvia is holding her nose with blood running down her hands, trying to get away from him. While he stands by the door, Sylvia grabs the lamp from beside the door and throws it at Candy. He knocks it down easily with his forearm, and Sylvia makes a run for the door.

As she reaches for the door, he reaches out and grabs her nightgown. She viciously pulls away, and the sheer fabric rips apart, exposing her breasts and panties.

This makes Candy even more upset, and he yells, Bitch, I’m going to kill you! Where’s my gun! Candy turns and walks toward the closet where he keeps his 9mm pistol.

Sylvia grabs the phone, then looks towards the room, and a chill runs down her back. With blood running down the front of her face and exposed chest, she slams the phone down and runs out of the apartment with nothing on but panties and blood. She runs downstairs and across the apartment complex to another building where one of her friends stays and bangs on the door. Boom! Boom!

Boom! Help me, please! she says. When the door opens, she runs in. Please help me. He’s going to kill me!

Who’s going to kill you, Sylvia? the elderly lady says.

My husband, he came into the house acting and talking crazy! He punched me in the face. I think my nose is broken. He’s lost his mind! Sylvia’s friend Juanita immediately picks up the phone and calls the police.

By the time the police showed up, Candy was long gone. We never saw or heard from Candy again. Two weeks after the incident with Candy (which was kept from the kids, by the way), my sister and I were brought to Orlando. To one of the most notorious neighborhoods in Orlando, Mercy Drive. They used to call it Murder Drive back then because somebody was always getting killed. Now, my grandma’s house was on the Northside of Jacksonville in a predominantly black neighborhood called Cleveland Rd. Right down the street from the renowned Cleveland Arms apartments. But in no way was it to be compared to the ghetto known as Mercy Drive. Until then, we had never lived in the projects. So I knew nothing of what went on in them. I got my knowledge of right and wrong (mostly wrong) from the older guys on Cleveland Rd. I just always had a knack for making other people do what I wanted them to do. The older boys got a kick out of my foul mouth and creative ways of doing shit I had no business doing. Cursing came naturally to me. If you haven’t figured it out yet, I’m Lil Free. This is the story of Lil Free turning into Ugly Yella. Now if you think this is just another urban story of yet another ignorant black man doing a bunch of ignorant shit, think again. I must admit, though, there is some ignorant shit in this book. ☺ (see, like the smiley face), but I guarantee you two things. One, you’ll learn something before you get to the end of this story.

And two, this will be the best muthafucking book you’ll ever read! ☺ (and it might be the only book you’ll ever read with smiley faces.) Let’s Go!!!!!!

3/17/1987

No, fa real, let’s go, Terrence said to Lil Free.

Man, these girls better not be ugly, Lil Free said. Terrance wanted to walk to the Palms Apartments for a girl he had met in school. The Palms was the biggest project on Mercy Drive. In fact, it was the biggest project in Orlando and one of the deadliest. There are seven different projects on Mercy, but The Palms was the biggest. It was also Palm Grove Gardens (where I live), Lakeside, Pepper Tree 1, and 2. Bordeaux and Rivera. All on one road that’s about half a mile long.

I am now ten years old and in the 5 th grade. Terrence is in the same grade as me, but he’s 12 years old. He told me he kept failing because he missed a lot of days of school. Reason being that his mom makes him stay home to babysit his little sister. Now I’ve been living in Palm Grove for about four months. I’ve been to Terrence’s house about 1000 times. I’ve never seen his mom or his sister. He’s always home alone, so I know he’s lying about the whole babysitting thing. He’d just rather stay home and run around the projects all day long. But Terrence helped me fight one time when three boys from Pine Hills tried to jump me in school. We spent the three days that we were suspended from school in his house, playing video games and eating egg and mayonnaise sandwiches. He was my only friend.

See, nobody liked me in Palm Grove because my mother was the manager. These silly muthafuckas actually thought the money they paid in rent went into my mom’s pocket. Even if that were true, it wouldn’t be much anyway. Because most of them were on section 8 and only paid like $20 or $30 a month in rent anyway. In any case, every time my mom would evict a tenant, their kids would come back and try to beat me up because my mom did her job. So I wasn’t liked that well, and even though everyone knew my name, they all called me the manager's son. They would say, That’s the manager's son right there, girl. His momma be putting everybody out. So I was always fighting or getting jumped or getting roughed up by older kids. After a few months of standing up for myself, being that it was just me and my sister, the older dudes stopped sending the guys my age to jump me so much.

I got my respect the day these four boys from my age group came from The Palm trying to run shit. I got tired of this one kid who was a little bigger than I was pushing me on the basketball court every time I tried to shoot the ball. I faked like I was going to shoot, and sure enough, he pushed me. I still had the ball in my hand, stepped back, and threw the ball as hard as I could at his face. The ball hit him square in the face and broke his nose. He was running blood like a faucet. While he was holding his nose, I ran up to him and, with all my might, kicked him in his nuts like I was trying to kick a 60-yard field goal. He screamed, then fell to his knees. After that, I just started punching him in his face until one of the older kids pulled me off of him.

Alright, Jit, you gonna kill ‘em. After that, I was still being called ‘the manager’s son,’ but I wasn’t antagonized as much.

Alright, hold up, let me go get my shit, Terrence said, then ran off in the direction of his apartment building. I had no idea what Terrence was referring to. I just hoped he didn’t take too long because I wasn’t going to sit here and wait. About 10 minutes later, Terrence popped up. Let’s go dog.

We started to walk out of the apartment complex, and I asked, Yo T, what you went to get?

I went to go get my shit, he said with a smile. He then reached into his front pocket and pulled out a little chrome gun. See? He passes the pistol to me. I held it in my hand and turned it over a couple of times. It’s a 25. I got seven bullets in the clip and one in the head, he says. Then he grabs the gun out of my hand, pops the clip out, shows it to me then pushes it back in. This is the first time I’ve ever seen a gun before.

My heart was racing and beating so hard I thought it would jump out of my chest. What do you mean in the head? I asked.

That means if you pull the trigger, it’ll shoot. He then pops the clip back out, then cocks the gun, and a bullet pops out. See, that’s the bullet that goes in the chamber when you cock it. He then gets the bullet off the ground, puts the clip back in the gun, and cocks it. See, now the bullet is back in the head. He then pops the clip back out, and using his shirt to hold the bullet, he puts the bullet back into the clip. Then he slams the clip back inside the small caliber pistol. Never put the bullets in the clip with your bare hands. It leaves fingerprints on the bullet. I nod my head, still staring at the pretty little instrument of death. Terrence puts the gun back in his pocket, and we start to walk down Mercy Drive so we can go across the street to The Palms. We gotta stop at the store, says Terrence.

Ok, cool.

The Mercy Market was a little store located directly in front of the massive two-story project buildings owned by Mr. Lee, the only Chinese in the hood. The little store sold everything from dish detergent to chicken wing dinners. There was nothing you couldn’t get at the Mercy Market. Some of the young girls with kids and no car would spend their whole welfare check at the tiny, crowded convenience store. There were always at least 6 to 12 niggas standing in front of the store at all times. Selling everything from weed to crack. The police were always jumping out on the guys at the store, but they would just run into the projects behind the store and come back later. Now sometimes, there were a few dudes standing behind the stores. I didn’t find out why they were there until years later. Anyway, after we left the store, which Terrence went into to buy 1.5 rolling papers,