Ivory Wilson He speaks with swagger. He smiles, but always a sideways grin making you doubt everything he says. But if he didn't smile you wouldn't believe him. If he didn't smile you wouldn't see the detail that remains from his former life: four diamonds set in gold in a front tooth. You see, Ivory Wilson III was a pimp. Wilson, 50, says he remembers when being a pimp was something much more sinister than anything you see in music videos. In his day it was a word used only to describe flashy men dressed in colorful suits with matching shoes and hats. In the back of seedy clubs and smoky bars, they would drink, snort cocaine, and play pool emerging only to order their women to get back to work. Now, the word pimp has become a widely used title, bestowed upon everything from a man or woman popular with the opposite sex (Jay-Z's "Dirt of Your Shoulder") to a customized vehicle (MTV's Pimp My Ride) "They use it freely, but they don't understand what it means. Today guys glorify it. They think it is something real slick. It ain't nothing but a con," Wilson said. "That word should be left in the world it is really meant for." Wilson says that world was his life for over 20 years and is the substance of his first book, "A Player's World Manual: Wanna be a Pimp?" which he wrote while serving a six-month prison sentence for conspiracy to distribute cocaine. A second book, "Big Mack," chronicles the last decade, including Wilson's recent descent into homelessness. Both books are an effort by Wilson to educate others about his former life and to provide him with a new start. He doesn't want to be a pimp any more; he wants to be a writer. The money from his former life ran out a year ago. Since then he has been living in Washington, D.C. shelters while holding odd jobs and selling Street Sense. He is finding that becoming a pimp was much easier than making a living as a writer. Wilson's freefall into the world of pimps and prostitutes began innocently. Wilson, then a 17-year-old Texas cowboy, thought he could make a difference by dropping out of high school to join the army and fight in Vietnam. He already had a wild streak and a sharp shot. But the war was over by the time he finished basic training and he was sent to Fort Riley, Ka., to await orders. His friends often traveled into nearby Junction City to meet prostitutes. Wilson stayed on the base and practiced pool. He might be a cowboy, but he was raised to respect authority. After a year of this, he gave in to temptation one night and found himself in the back room of a club called Flamingo, playing pool and being hustled by Unc, the most powerful pimp in town. Intimidated and desperate to fit in, that night Wilson had his first drink, smoked his first joint, and snorted his first line of cocaine, not knowing what it was. "I was sitting there and my mind was going around like a tape recorder and my eyes were like a movie camera," Wilson said. "Everything I saw, it's kind of hard to explain, but I was understanding what was going on but I couldn't sort it out right then. It was all coming in so fast." As the men drank and played, prostitutes would come in and give Unc rolls of money. One prostitute stayed too long in the back room and Unc made his point by using a pool cue to send her tumbling to the floor. She bounced up, seemingly unharmed and walked out. Wilson was aghast, but quiet. "I said oh my God, I come from Texas, I don't know whether to defend this woman or mind my business, but I minded my business," Wilson said. Wilson said his quiet demeanor and pool skills impressed Unc, who had already told the bartender that he was making plans for Wilson to become his next pimp. That night Wilson even earned the nickname "Pretty Red," which has stuck with him ever since. "It's like, that's not right, but their pockets were full of money and big diamonds," Wilson said. "During those times it was different, you know, for a black man. It was like an infection, you know, you had to have something and this was a way [to come up behind] our idols and role models." Wilson's association with Unc made him an overnight celebrity on the base and in the town. He rode around on patrol with the Unc's crowd but didn't pimp. It wasn't until he had his heart broken that he decided to pimp. Her name was Renee and she hated seeing Wilson hanging around with Unc's crowd. Wilson fell hard for her and after a month of dating told his family that he planned to marry her. When his friends in the army learned of his marriage plans they cautioned him. They told him that not only did Renee have a relationship with another soldier stationed in Germany, but also that she had become pregnant before he left. Timidly, Wilson said, he asked Renee if the rumor was true. She dropped the bowl of cereal she was eating and begged forgiveness as he walked away. "I had a pain in my heart," Wilson said. "My thoughts about a woman, my feelings towards women, they got hard, real hard." That night, he made the decision to become a pimp to "punish" women. Unc more than agreed, with this decision. Unc sent Wilson to Kansas City to pick out five double-breasted suits, all different colors, with matching shoes and hats, and a prostitute. All the items on Wilson's list were easy to pick up. Wilson said his first prostitute was from Minnesota and handed over her earnings with little argument. When they returned to Junction City, Wilson was picked up by the police for running away from the army and spent three months in jail. He lost his prostitute, but there were many more to come. The next 12 years of Wilson's life were a blur spent traveling from city to city, living on cocaine and cognac. "One became two, then five and soon 20," Wilson said. "I wanted to be bigger than Unc." Prison changed all that. In 1984, Wilson was charged with conspiracy to distribute cocaine and conspiracy to commit murder. The latter charge was dropped, but he was sentenced to three to 10 years in Kansas's Hutchinson prison. Wilson said life in the prison was not so bad. There was a prison rodeo and he was eager to get back on a bull. When the rodeo fell through, Wilson found a job with the prison catering company. His boss especially liked him and asked him to break a colt she had for her son. When Wilson completed the job in less than 15 minutes, he earned a position on the prison farm and the respect of his warden. In less than three years, he impressed the parole board with the promise to keep out of trouble and return to life on a ranch. Wilson kept his promise for a few years. But he thought there were more important things to be done, and that they couldn't be done in Texas. While in prison, Wilson had written a book about his life and he was desperate to get it published. He felt the only way to do this would be to go to Washington, D.C., a city where he thought media thrived. He was able to sell 500 self-published books for $25 on the corner of 14th and U streets, NW. He quit being a pimp and worked a series of odd jobs before running out of money. Wilson no longer has the jewelry or the fancy clothes in which he once paraded around. Instead, he wears several layers of shirts and sweaters to cover his slender body and a cap to cover his bald head. His glasses inching down his nose and his more-salt-than-pepper beard are the only visible signs of his age. "Maybe I think this is my punishment for using a lot of women," Wilson said. "I used so many women I can't remember names or faces, so I know that it had to be that reason." There are at least three women about whom Wilson does care: his daughters. They are spread across the country, and Wilson has varying contact with each of them. He talks to his youngest, a 14-year-old in Florida, the most. She doesn't know anything about his past and he would like to keep it that way. It seems that his biggest worry for all three is that they will end up like his old prostitutes. Two of the three were born to prostitutes. "I hope my daughter ain't that way because her mother was. But she's not. She's strong," Wilson said of his 20-year-old daughter Jasmine, whose mother is currently in prison. He said he would talk to all three of his daughters more but he isn't sure how to talk to them about who he was. More than ever, Wilson is a loner. Wilson lived in Franklin Shelter in D.C. where he met a Street Sense vendor who encouraged him to sell the street paper as a way to make an income and possibly get his stories published. Since becoming homeless, Wilson had tried to keep a low profile in the shelter and with his new employers. Now that they know about his past, they are supportive of his current efforts . It has been more than 30 years since Wilson got into the game and it has changed much since then. As we sit in the upstairs of the L Street Lounge in Northwest D.C., two young girls have their arms laced around graying men old enough to be their fathers. In the middle of the bar is a young man, not quite over 25, who goes by James. James is young in the game as well as in life and knows that if Pretty Red is as big as he says then he is probably lying low or traveling. Either way, James hasn't heard of Wilson or the book. But Wilson doesn't seem to mind his name fading from the scene. Soon, he says, he will be known as a writer. "I know that some day I am going to meet somebody that is going to give me that opportunity to talk to them and realize that I am very talented at something else besides turning women into hookers. That I am a writer."