The first time I thought about pimping, I didn’t really call it that. I just saw an opportunity and decided to go for it.

Cassandra and I were lying in the bed looking at the Chicago Reader - a local free news paper who’s only purpose in the black community is to look at the help wanted ads. We had always got a kick out of laughing at the people writing in for sexual and relationship advice, that’s why we read it.

Anyway, I was not working at the time and was very hungry. I needed money. I saw an ad in the escort section that was hiring for erotic massage. “hiring girls for topless, erotic, massage”. I turned to Cassandra and began to talk to her about all the money we could make if she did it. I talked about how we could drive a car, and I could look fly, and we could get up out her momma’s apartment.

I don’t remember exactly what I said, but she definitely went for it. A combination of, I really need this and you’ll do it if u love me, etc etc. I could tell that the thought of it made her nervous, but I also remember that convincing her to go wasn’t that hard, because by this time she was in love with me.

It was night time when we went there. She was told to come in for an interview at an apartment downtown. That tall, black building that over looks navy pier and lake Michigan. Shaped like a three leaf clover if u were looking at it from the top down.

Most of the trip there I don’t remember. I do remember feeling a weird nervousness though as we got closer to the building. My heart was definitely pounding. She was my girl and a part of me old me that I was wrong. A part of me was scared about what could happen to her. Could she be raped? Could a customer get violent with her? Half of me was scared of the possibility of something bad happening and how it would be my fault, and the other half wanted the money. I gave in to the money half and kept quiet about the rest.

We got about half a block to the lobby of the building and I told her to gone upstairs. If I was nervous, I can just imagine how she must’ve felt.

She went upstairs and I waited, never getting too close to the building. I was amazed that this was the same building that I had promised myself I would live in one day. The entire time I was sweating in fear about the possibility of something bad happening to her. It was about half an hour before she came back down. The look on her face horrified me. She had tears flowing down her face. I was scared that my fears had been realized. What had happened to her?

With the tears flowing she came striding toward me. The only thing she kept saying is, “I can’t. I can’t. I can’t do it!” I hugged her and asked her what had happened, why was she crying like that. She told me that there was a white man with a pony tail, and girls walking around with no shirt on and cocaine on the table. She said the guy slapped the shit out of one of the girls and then asked her (Cassandra) to take her top off. She said she was too scared and then looked at me with red puffy eyes and a face full of tears and begged me not to send her back up there.

This was a turning point for me. It was like I had come to a fork in the road. On the left is love, understanding, and me not wanting to see my girl hurt. On the right is money, a cold heart, and me not giving a shit about what a bitch feels. I looked her in the eyes and saw my baby crying and couldn’t do it. I had to choose love. I hugged her and told her let’s go home. I felt relieved that she hadn’t got hurt.

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I don’t know where I was going that day. I can’t remember. I do know that I was on the train though. It was the Wilson stop, right around the corner from Darryl’s crib. Maybe I was on my way to school, who knows. But that’s where I saw her. or actually I think saw me. No, we saw each other. There was a quiet nervousness surround the both of us. She was cute as hell to me. Petite. Pretty, but not too pretty. More like, a girl next door look to her. She looked easy to get along with. Like I said, it’s strange when you notice that a girl likes you. Sandra’s ( I call her Sandra for short ) thing was that she would look down at the ground, and fidget with her hands or her feet or something. I could feel that she liked me. I think she could feel that I liked her too.

We were waiting on the same train, the Dan Ryan El going south. The trains in Chicago are divided into cars. there’s usually about 8-10 separate car per train, and each car has 2 doors. When our train pulled up, a door stopped right in front of me. and a door to another car stopped right in front of her, about 10 feet away. I hesitated walking into my separate train car. If I had I wouldn’t have a chance to talk to this girl. Oh well, I walked in anyway. To my surprise though, she wasn’t going for that. She ran over to my door and walked into the train. She stood right in front of me, still looking down and not saying anything. I didn’t say anything either, but I definitely noticed the fact that she had made that big effort to place herself near me. I guess she was waiting on me to speak. I did. Can’t remember what I said though.

Relationships in our day and age are strange. Have you ever noticed that no one ever says, “hey, I think you should be my girlfriend”? There’s never a moment when the relationship starts officially. You just look up one day and, that’s your girl. Sandra was mine. We hit it off great. So great in fact that I left Darryl’s house and moved in with her.

It was Cassandra, Cassandra’s lil sister, her mother, and her mother’s boyfriend, and me all in one house. Certain things run rampant in the hood, and crack is one of them. Sandra’s mom was a crack head also. And she was alot worse than Darryl’s mom with it. But she was still a nice lady to me most of the time, and I enjoyed living there also.

Up until this time I was skinny as a stick. My mom was always a health food nut. She never fried anything in our house. We ate nasty shit like raw spinach and stuff like that. When I moved into Cassandra’s house, I discovered.. .. .. Crisco. I must’ve fried everything. Fried chicken, fried pork chops, Fried fries, fried everything. Especially on the 1st of the month. On the first of the month we would goto Aldi’s with a shopping cart and come back with that cart full of groceries. Mostly junk. In my year or so living with Cassandra’s mom, I must’ve put on 60 lbs.

Their house was also covered in roaches. it was the worst I had ever seen. thinking back on it now it was absolutely disgusting. At night when we went into the kitchen and turned the lights on, the floors, walls, and ceilings were all covered in roaches. And that bullshit about roaches scattering in the light just aint true. at least not for these pests. they would pretty much stay right where the fuck they was until you stepped on a couple of them bastards, then they would scatter. I remember opening the cabinate doors to find the inside covered from end to end in roaches. Packed tight, back to back. You’d have to open and slam the cabinate door quickly to make most of them fall off so that you could reach in and get what you want. It’s unheard of for me to live in such a place now, but it was nothing to me then. I just adapted. Don’t leave your plate on the table for more than 5 seconds. hold your drink in between your legs. And sleep with your mouth closed. No big deal.

Life with Cassandra was good. She was my first real girlfriend. My first serious relationship as I put it back then. There was alot of passion between us. While her mom and friends were in one room smoking, we’d usually be in another room, with the door closed fucking. To be honest, I don’t think I’ve had the same passion during sex since then as I had with her. That was young and in love fuckin. Hard, go at it again and again fucking. Let’s see how many times I can bust a nut fucking. There was so much passion there. Unfortunately, sex isn’t the only place where young passion showed itself. Cassandra was my first girlfriend, first serious relationship and, the first girl I ever beat.

I can’t remember alot about myself growing up, but I remember this moment like it was yesterday. We were arguing about something. Back then I was insanely jealous. I would go crazy over stupid things. She was an R Kelly fan, and I would insist that she throw away all of her R Kelly CD’s, turn off the radio whenever a guy was singing on it (especially R Kelly), and never watch music videos. Whatever we was arguing about, I’m sure it probably had something to do with R Kelly, or KC from Jodecee.

We were in our usual fucking room. It was one of 2 rooms where the handle locked. Her mom and friends always went into the other room to smoke. They liked that room because it was close to the stove. I think they needed the fire on the stove for whatever they were doing. I can clearly remember the extra strong smell of crack in the air that night. Anyway, we were arguing, and I kept badgering her and badgering her. I had backed her into the corner of the room and was really laying into her verbally about whatever I was angry at. Finally she said something very strange. Looking up at me, with tears in her eyes she said, “Why don’t you just hit me. Why don’t you just beat my ass.” Then the sadness turned to anger, as she started yelling at me. “hit me! Hit me you punk!”. I didn’t know what to do. I had never been there before. I was raised to never hit a woman.

Here she was, daring me to hit her. Begging me to hit her. With just a couple of seconds of thought, I balled my fist up and swung on her. She immediately dropped to the floor and curled up in a little ball and started crying. Almost instantly I felt sorry. I dropped down on my knees next to her, and began telling her how incredibly sorry I was for putting my hands on her. And then, she accepted my apology. I told her I’d never do it again. She put her head on my chest, and we made love shortly after that. It was good. But something had changed in me. It was the power I felt. 1 second this girl is defying me, screaming at the top of her lungs, and then with one swing, I could make her shut the fuck up. And then she was cooing in my arms. She went from being against me to being my baby again, totally under my control. I liked that control. I used it again many, many times after that night.

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Edited: Changed some people’s names out of respect for their privacy

I’m on my own. Thinking I’m grown. I live with my high school buddy, Barry, his mom and his little brother. This world is totally different from where I grew up. Barry’s mom is a heavy drug user; she does crack. Barry seems to be oblivious to it. I guess it’s similar to my roaches at the homeless shelter. From everyone on the outside looking in, it may seem crazy, exotic or strange, but when you live in a situation, it’s just.. .. normal. Barry’s mom often had friends coming over. Older people in their late 30’s or 40’s. Or at least that’s what they LOOKED like. Knowing what I know now, the drugs probably had them looking older than they really were. Crack does something strange to a person. It sorta dries them out. Like a grape turning into a raisin. They turn skinny usually, though some fat crack heads stay fat. But they look dry. Worn. Like old car leather.

When her friends would come over they would commandeer the kitchen. Us kids would be told to leave the room and stay upstairs so that her and her friends could have some privacy. To this day, I’ve only ever seen anyone put a crack pipe to their mouth on TV. I’ve never seen it in person. But I remember the smell. There is no way to describe what crack smoke smells like. it’s just something you’d have to experience. It’s strong though, at least it was to my virgin nose. Very pugnant. It often gave me headaches, as I could smell it all the way upstairs. Barry never mentioned anything about what his mom did. neither did his younger brother. Neither did I. (I think it should be noted here that Barry’s mom now a days is no longer a crack head. She holds down a good job, has a car, and an apartment. She really cleaned up. But then again, she was never that bad. She always took care of her kids.)

I only mention the crack smoking because it was new to me. In actuality, staying with Barry and his familly was fun! I had a ball. it was a totally new thing to be able to come in and out of the house WHENEVER I wanted to. We stayed out all night with the neighborhood kids. It was my first time hanging out with thugs. There was Snook, small kat, about 5′5″. He wore a thick beard and braids in his head. Usually, the braids were half done, and the other half of his hair was puffed out in a half afro. Snook seemed to be the most charismatic, and swore up and down he ran all the stones in the nighborhood. I don’t know what his real title was, but he was definately plugged for a little kid.

There was lil BWe called him lil B because his name was Barry too. He was shorter than my friend Barry but definately not smaller. Lil B was swole. 50 cent wasn’t out at the time, but when 50 dropped his 1st albulm some years later, everybody noticed the uncanny resemblence he had to lil B. they look like twins. I teas Lil B to this day about that whenever I see him.

There was CeeCee. A half white half black kid who’s sister (Sonya) had gotten me beat up some years ago. She lied to a bunch of boys and told them that I had jumped on her. They waited for me after school one day as I was walking home. Must’ve been 10 of em. All I remember was the first punch. Anyway, CeeCee’s stand out characteristic was his hair. It was long as hell, way past his shoulder. Kind of a dirty blonde color. We all had butta’s back then, and CeeCee’s was the longest. Personally I didn’t think he deserved as much props about the length of his hair as he got, seeing as how he WAS half white. I mean, white people’s hair is always longer.

There were other’s in that neighbor hood. All stones. But these were the guys Barry and I hung around most. Everyday, was pretty much the same thing. Wake up, wash up. Lay out your clothes. Iron your clothes (back then ironing our pants was an artform that took about 1 hour and 1/4 a can of starch. best crease wins). head outside and see who’s out there. and from then on, we kicked around stories about what happened yesterday, who fucked who, who beat who up, and so on. Oh, yeah, and we argued all day aobut who was going to buy the weed, and the beer. that was the whole day. Hanging out, smoking weed, and drinking beer. I didn’t do any weed smoking though. Was never really my thing.

Like I said, living with Barry was fun. It’s funny just how much can happen, and how much trouble you can get into within the confines of the 2 block radius that is your hood. I attended highschool most days. Some days, I didn’t go though. Unfortunately, the more days I missed, the more I felt like I was being left behind when I was in school. I really could feel this in my math class. I would stroll in after not being in there for like a week, and they were already 3 or for lessons ahead of me. So whatever the hell Mr. Taylor was trying to explain to me about exponents or whatever, I surely couldn’t understand it. It’s hard to feel like you’re stupid, when you’ve spent most of your life in gifted class rooms. I’m used to being at the absolute head of every class, and breezing through everything. but for the first time in my life, I couldn’t answer the questions the teacher was asking me. And the other kids was looking at me like I was stupid.

But life went on as normal until one day when I met a girl who would change me for a long time. Her name was Cassandra.

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In a single file line we were marched in. First they took our picture. Then they mark a letter on the top of your hand with a black marker. Then they moved us to the bull pin. The walls were stone. Covered in a drab, grey paint. each stone was about 2′ by 2′. the flourecent light cast that stale, steril, dead glow on everything. I hate flourecent lights. we were herded into the bull pin. the bull pin is a cage, about 25′x25′ around. three sides of the cage is grey painted stone and one side of it are floor to cieling bars. The cage door stayed open as more and more men were huddled in. on 2 sides of the cage, there was a bench. it went from the bars to one corner and from that corner it followed the wall to the other corner. at that corner there was the bathroom. 1 stainless steel toilette with no lid. When you pushed the button on the wall about 1 foot above the toilette the flushing sound could be heard in the ohter end of the room. the only privacy that bathroom offered was a waist high wall that stuck out about 20 of the 25 foot length of the that side of the bull pin.

Anyone who had managed to sneak a cigarette in at this point was now lucky. Any one who happened to sneak in a pack, was a hustler. I heard guys selling squares for $5 a piece. At this point, you weren’t going to be able to smoke again for another 12 hours or so, and you probably hadn’t had a cigarette since you got arrested 24 - 48 hours ago, so you would’ve paid anything for a cigarette. If you’re white, and you either have a square or buy one, you wasted your money. If you’re lucky, they let you get a puff off of it before they pressure you into sharing. You watch your precious cigarette get passed around to about 10 other guys who you don’t want to make enemies with. In the world, white is the majority. But in jail, you’re definitely by far the minority.

I quickly grabbed a spot on the bench, as I knew that if I didn’t, I’d be sitting on the floor. I have a thing about sitting on jail floors. After about 3 hours of watching that bull pen fill up with people you are told to come out and get your letters and numbers. Basically, about 10 feet from the bull pen is a row of desks. desks built into a waist height stone wall protruding from the floor. You go and you sit at one of these desks, and across from you is a phsychiatrist. Mine asked me a series of questions. What’s your race? African American. What’s your religion? Buddhist. Do you have any tattoos? Yes, on my upper arm, says Pman. Do you take any medicine? no. Any gang affiliations? no. Are you feeling suicidal?

Damn I thought. Suicidal? Part of me just wanted to go home so bad. I couldn’t believe I was there. I kept saying to myself, I don’t belong here. It had all been some kind of crazy bad dream. Her question of if I was feeling suicidal was like the first time in days anyone had acted like they even gave a shit about me. I wanted to tell her yes, please let me go home. But, I knew that if I said I was suicidal, it would only get me sent to the hospital. The jail hospital. Still jail. And I wasn’t crazy or suicidal and wasn’t going to pretend to be.

Are you suicidal? no. Then she had me hold both of my arms out toward her, with my palms faced up. She wrote some letters and numbers on both arms and told me to go ahead back to the bull pen. As I was walking back I noticed a tall, dark skinned sherif with a mason ring on. I figured, now’s as good a time as any to point out what I was to someone, so I gave it a try. I asked him if he was a mason, he said what he said, I said what I said, and he told me to get my ass back into the bull pin. That was pointless. I was still in jail.

The bull pin continually got more and more packed until it got to the point where the entire floor was covered by inmates. And then we were all told to get up and go stand in a new line. First was posessions. We had to place everything we came in with in a plastic bag. It was a thick, strong plastic. the kind you need a knife to cut, you can’t just tear it. Then we went to stand in line to go into this small door. I wondered what was behind that door, but I wasn’t about to ask anyone around me. I didn’t have to though. That door was famous. So was the man behind it. The dick dr was his name. Every fucked up kid in Chicago who had ever been to cook county jail knows who the dick dr is. he’s a short, huched back man. Black as hell, and totally cold. When you walk into that room, you walk up to this big garbage can, or container or whatever, pull your dick out over it and stand there while the hunch back of County Jail sticks a 5 inch metal cotton swab up the tip of your dick.

I heard all of this from the guy behind me talking to the guy in front of me. I was petrified. NOTHING is supposed to go up there! I began to sweat as we got closer and closer to that door. The line was around the corner so at first, I couldn’t see inside the door. But as the line got shorter, and I began to turn that corner I saw him. He was short, black as hell, wore thick bifocal glasses and had a white dr’s coat on that contrasted starkly with his charcoal skin. I was scared shitless. I’ve always been afraid of needles. I could not take this. I saw the long metal sticks that he shoved up each terrified inmates penis. Everyone of them were quiet as they walked in the room. Not one of them wanted to show one hint of fear or pain. They were all just as scared about that thing as I was. When the person in front of me walked in I could feel my heart pounding. A pounding heart drowns out all othr noise. All you can notice is your heart pounding, your heavy breathing, and whatever it is that has you scared shitless. I breathed fast and hard. I started feeling light headed. The Dick Dr grabbed the guy in front of me by the penis, and shoved that 5″ long metal spike up his urethra with a lot of force and zero sympathy. he didn’t even look the man in the eye. You could see the inmates body tense up as the cotton swab went in. He ground his teeth, and was in his own quiet hell for about 3 seconds. Then it was my turn.

I walked in and next to the Dick Dr was the Mason sheriff I had spoken to a couple of hours earlier. He was handing the dick dr the cotton swabs from hell. He handed the Dr my swab. The dick Dr grabbed my limp dick and prepared to insert. I held my breath, and then the mason looked at me and said, “..wait, he gets a pass”. He threw my swab into the barrel with the other swabs to be tested, and I walked through untouched. God bless masonry.

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This post was taken from an old blog that I used to keep about my exploits in Pimping. I had to take the blog down when the hoe I was messing with threatened to use the blog as evidence to turn me in to the police. How stupid of me to let a hoe control me with threats. Anyway, here’s the post:

I’m in a hotel room, laying next to a high, drunk, and ‘rolling’ bitch. She is sleeping at the moment.

At 12:30am, after having not received any money from this Bitch all week, I had to yell at her to convince her that she shouldn’t be sleeping, she should be working and getting more money. I had to ask her repeatedly to get up and post, though I was constantly dismissed with an unenthusiastic “I’ll get up in a minute”. When I got up, turned on the light, and gave her a very threatening “get up OR ELSE” she moved quickly to do her job, but made smart comments under her breath. “I should’ve let you go home” aluding to a couple of hours earlier when I planned on leaving and going home to my family. My taking off my belt and threatening to punish the bitch quickly shut her up.

Now I’m laying in the motel bed, typing on a laptop, while this drunk, high, and rolling bitch sleeps. A bitch that has given me NO money in almost a week’s time. What is a Pimp to do? She seems to be deathly afraid of being beaten with a belt. I know, because I’ve threatened to do just that a couple of times before. Yet I feel that using violence is the easy way out. It surely doesn’t take much thought or creativity to just ‘hit the bitch’ when she starts acting up.

Bitches are unstable creatures. One moment they adore you, the next moment, they act like they’re going to blow. My instinct tells me though, that that’s just a tactic for the bitch to get what she wants. In this case I think a high, drunk, rollin bitch just wanted to goto sleep.

I really need to turn this around. I don’t want to fire my one and only hoe.. .. .. but I will if I have to.

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