Free Character Writing Prompts #39: 
The Seedy Underbelly

Take a walk on the wild side with these character writing prompts about the seedy underbelly. This is a section of characters that most people would rather not talk about. They are the kind of people that you'd rather your children not find out about until they're older, if ever. The section includes prostitutes and pimps, drug addicts and people on the streets. A story that is set in a major city cannot help but address that there are rough parts of town that include such characters. That being said, not everybody in the seedy underbelly of an urban area is there by choice and that can be a major factor when creating the personalities of such underground characters. 

Free Character Writing Prompts #39: The Seedy Underbelly

1. He was lucky he hadn't been killed that night. He had been down at the corner store when a gang of people working for his drug dealer shot up his apartment. He was a complete drug addict and as a result, he'd racked up an incredible debt with his dealer. To avoid the issue, he spent as little time at home as possible and on this night it paid off. It always seemed like he'd get out of the neighborhood and make something of himself, but he got into crack at the end of high school to take the edge off. It was a mistake he wished he could take back as he stepped onto the bus out of town. Will he be successful escaping from the dealer and can he reform his life?

2. His large stable of ladies made him one of the most sought after pimps in town, both by men looking for a good time and the police department. Since some of his clients were high ranking city officials, he'd gained a little bit of immunity for himself. He'd been in the business for the last 10 years or so after becoming a sort of assistant for the last majorly successful pimp in the area. He grew his business by leaps and bounds by taking it online and keeping it more secure. He treated his ladies with respect and as a result, they tended to skim less off the top than most would. As a relatively competent businessman, why did he decide to go into the prostitution business and what will the future hold for him?

3. People had this image of a female escort as some kind of drugged out lowlife, but she laughed at such an image when she walked around her completely paid for house in a very upscale neighborhood. She made upwards of $1,000 an hour when she was working and her clientele would never label her as a lowlife. They thought she was amazing and as a result, they paid her higher than some CEOs. Sure, she wouldn't want her daughter to take on the same profession as it had its stranger moments and she thought by gaining as much money as she could, she could ensure her daughter would have a better life. What are the qualities that make her escort-worthy and what would she do if she could no longer participate in the job?

4. She loved luring men back to their apartment and breaking out the handcuffs. After all, men loved to be rendered completely defenseless so she could work "her magic" on them. Her magic, of course, was to rob them of all their possessions and money so she could cash out and skip town. It was so easy because all men wanted was sex, she thought and in her experience she'd been right. She'd had a blind hatred for men ever since her father left her and her mother high and dry over a decade ago. Since then, she hoped to find her father and take him for all he had and until that point, she would rob sex-crazed men and send as much money home to her mother as she could. Will she ever find her father and has she ever had any close calls in her particular business?

5. During the day he would keep crime off the streets and at night he would do everything he could to facilitate it. See, he'd learned that he could make a lot more money if he played both sides against each other. As a crooked cop, he actually knew more about the criminal infrastructure of the city than most honest police did and he always had that as leverage in case he was caught. He did have a few pangs of hable to put his son through college and pay off his mortgage with ease as opposed to struggling. How did he become corrupt in the first place and will he ever get caught?

6. He wasn't proud of the things he did during the night. He usually wasn't even 100 percent aware of all his actions until he woke up the next morning. Some people were fortunate enough to black out but he had an impeccable memory. He knew drugs were involved and giving away a part of his dignity in the process. All he wanted was more as often as he could get it and to fulfill this obligation, he did everything his dealers told him to do. He'd killed and he'd assaulted people just to satisfy his habit. He hated everything about himself and considered suicide on a daily basis. What keeps him alive with all this guilt and what did he do before his addiction changed his life?

7. You couldn't help but notice her come into your favorite donut shop. She was always outside of the place soliciting "donations" for a cause she was raising money for. One week it would be fundraising for breast cancer and the next week it would be for the homeless. She had sunken eyes and cheeks and a set of teeth that looked in serious need of surgery. You weren't sure what her issue was, but you were frustrated by the stories she would tell new customers in order to get them to take pity on her. You knew that altruism was the farthest thing from your mind and the only thing that kept you from calling the cops was the pity you took on her. What is it she does with this money and why? Does she feel any emotions about soliciting money on the behalf of causes she never plans on donating to?

8. She had always been a big fan of Las Vegas, so she figured why not bring Vegas to her city's doorstep. She ran an underground high-stakes poker league that usually drew some of the seediest fellow from town. They were reluctant to join something set up by a woman at first, but she talked and acted tough enough for them to trust her. She was exhilarated every night by several games in which over a million dollars exchanged hands. She didn't even care about getting caught, because she was currently living out a sort of dream and whatever sentence she got would be worth it. What was it about this secretive gambling that made her so excited?

9. While some might have seen him as part of the problem, he felt he was simply adding to the solution. He was the supplier of most of the unregistered weapons in town, but his records were so airtight that nobody could possibly trace them back to him. He figured that if he gave the gangs, the dealers and the other lowlifes in town the weaponry they needed, they would naturally thin each other out a bit. If he happened to take part in the financial benefit of such a service, he would gladly take it. He saw himself as a sort of Yojimbo and frequently watched that movie to remind himself of that belief. How did he get into this line of work and what is his day-to-day life like?

10. She saw the entire thing as a business opportunity. The sex industry needed people and she found people, typically without their understanding or against their will. The people she found were usually young and were looking for a way out. She never liked the term "human trafficking" and much preferred the phrase "industry relocation" as she was relocating kids from the business of being young and stupid to being useful. She rarely felt any moral reservations at all from taking part in this practice as she thought she had found her place in the world. What happened to her in her life that made her think being part of such a practice was righteous in some way? 

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Done with Character Writing Prompts about the Seedy Underbelly? Go back to Creative Writing Prompts. 

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Written by Bryan Cohen

Bryan Cohen is the author of more than 30 books, many of which focus on creative writing and blasting through that pesky writer's block. His books have sold more than 20,000 copies. You can find him on and Facebook.
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