Chapter 1: Lady of the Night

Mary Jane Watson never thought she’d be doing this kind of thing before. She had a great job and was happy with her boyfriend Peter Parker. He was the one and only Spider-Man and an actual real life hero. It was every girl’s dream to have her kind of life.

On the other hand, dreams and happiness didn’t pay the bills. Nor did being a hero. They were able to get off lightly the first few months. But as time went on, they couldn’t put it off any longer. They needed to find a way.

“I’ll find some other job, okay MJ? You don’t need to worry.”

“I’ll try and find something else too Peter. We’ll make this work. I promise!”

She looked up local listings in the classifieds, she found small odd jobs in the neighborhood. But it was never enough. They were struggling, there was no getting around it. With Peter being on hero duty all the time, he couldn’t devote as much time to finding extra cash as he wanted.

She sighed to herself. She couldn’t believe what she was thinking. But she had to make ends meet. Coincidentally enough, Peter had just gotten back. He was going to konk out in bed, he was exhausted after a long day saving the world. She said she had to start her new job. He wished her the best of luck. Thankfully he didn’t suspect a thing.

She knew where all the big time pimps liked to congregate. She was never a call girl or wanted anything to do with that sort of life, but it was an open secret that everyone knew, even innocent little grannies. She knew how people could treat ladies of the night. Spider-Man was already off busy saving the world, she would not tell him about what she planned to do. He could easily give her the protection she needed, but she also knew it would crush him to see her do this kind of thing and tear him up inside even more than the average stresses of being a hero. She made up her mind, that was it. That night she headed there first thing.

She went there for protection. But the instant she went there, she found the pimps looking her over like she was a piece of meat. The other girls were also giving her looks of amusement and disdain. She suddenly felt dirty and out of place. She wondered how many things these ladies had been through. What kind of indignities they had to suffer.

Before she knew it, the other pimps had her surrounded. Guys of various ages and heights, they shamelessly touched all over her, grabbing her rump and feeling up her legs. She had come in what she thought was proper ho attire, a big trench coat along with short shorts and little t-shirt. But just like everything else about her, these clothes were kinda high class, the kind of thing you’d see on the rich daughters who liked to go on Spring Break while getting trashed out of their minds, and they seemed to be laughing at her for even bringing these kind of designer garments to such a locale. The other prostitutes were no less indecent, throwing her hair about and laughing.

“Youse a bit too high class for this kind of place little girl...” said a big fat Italian pimp from behind her had darted a hand to the crotch of her shorts and lustfully smelled her hair, enjoying the smell of her shampoo. Her first thought was that this guy might have even been in the mob.

“Just the way I like it,” said a skinnier one with some gold teeth who was right in front of her and grabbing her tits. He was leaning forward and trying to kiss her naturally pouty lips. Irritated, she managed to break free of them.

“I think I should be going,” MJ said and made to turn around and leave. She couldn’t believe she had ever entertained this kind of idea and was pushing it well out of her mind. But then she was covered on all ends. She made to push her way out but they pushed her right back.

“No I think you shouldn’t,” said one of the girls, smiling. MJ didn’t know how old she was, she could have been the same age as her or older, no doubt she had plenty of makeup on so it was hard to tell. But she was one of the prettier looking prostitutes she had seen, a blonde with her hair naturally styled in curls and her full lips all shiny and pink didn’t look pumped up with injections. It was hard to tell what ethnicity she was, her hair wasn’t dark at the roots with darker skin but her skin wasn’t white and she had a naturally dark complexion. She was eyeing the ginger haired girl, smiling at her like she was a predator. She got closer to MJ, she was a few inches taller than her. “It’s not nice to say no to a daddy. Maybe you should apologize.”

“Just let me go, alright? I don’t want any trouble.”

She got closer. “Don’t you know baby girl? We are trouble.”

Then she pulled MJ right into a cruel kiss. The others were hollering and whooping at the spectacle. The hooker was being forceful from the beginning. She was trying to get away from her, but those hands were clasped right around her cheeks. The hooker wasn’t that strong but it was in the malice in her hands that kept the two of them locked. Her big lips were engulfing MJ’s own, and the sheer force that she was using made it felt like her face was being sucked up by a vacuum.

The others were watching it go down with smiles on their faces. No matter how hard MJ tried to get away, the hooker kept on kissing her. The hooker got a little more aggressive and opened up her mouth, trying to shove her tongue in there. But the other girl was resistant to the end.

The hooker grabbed MJ’s crotch. That shocked her enough to finally push the hooker back. But the other woman wasn’t having it and seizing her chin, pulled her into another sick kiss. She grabbed MJ’s crotch again. It was fortunate she was wearing shorts and not a skirt, protecting her nether regions. That didn’t matter at all to the hooker who forcefully massaged her there. But even with as well protected as she was, between the hooker’s tongue actually pushing through and getting into her mouth and those raunchy touches, she was feeling a lewd ache in her pussy that wouldn’t go away no matter how much she tried otherwise.

MJ finally managed to break free and push the hooker back. The audience sucked in their breath and made shocked noises like they were watching some reality TV show. She had turned away, wiping her mouth of the cheap lipstick staining her lips with the back of her hand when the hooker took the opportunity to spank her ass.

MJ glared at her and put up her dukes like she was ready to fight. The hooker held her hands up and flashed her big fake nails like she would tear the other woman apart if she tried anything before she smiled and laughed unpleasantly.

“I’ll tell you what,” she said, licking her lips. “She tastes as good as she looks.”

MJ looked all around her. She suddenly felt very foolish. She knew that was a bad idea, what she just did. Coming here altogether was dumb but actually giving this kind of woman that look instead of making another to bolt was even worse. All because the hooker was beckoned at her as if to confirm that suspicion that she really would have to fight it out. But then there was a loud thud in the back.

They all looked in that direction. MJ turned to look too. It was a tall well dressed man. All the pimps there were dressed fine but anyone looking at them wouldn’t have doubted they were pimps. This one on the other hand was dressed fine from head to toe in a stylish way, a black suit and fine waistcoat that wouldn’t have been out of place at a business meeting. He was definitely an older guy probably in his sixties, with a full head of white hair and a bit heavyset in years, but his face was so clean shaven and he had such a wild vitality that he looked younger than he actually was though even if he had gotten a dye job, he still wouldn’t be able to pass for a young man. He strode on forward with no regard for the rest of them.

He was looking at MJ the whole time. His smile would have been gentle if not for the vicious streak in his eyes. He almost looked like a wolf. The others who had surrounded her had backed away.

“Well, well, this isn’t a good place for little girls,” he said. “Don’t you know what kind of people come here?” he said, looking at the others. MJ had had it by now, she was about to say something to him even with how tall he was. But his compatriots’ responses surprised her.

“We’re sorry big guy!” said a small pudgy pimp overdressed with shiny shades and bling all over. “We didn’t mean to...”

“Can it you morons. We’re pimps but that doesn’t mean we don’t have to be gentlemen too, right?” He was looking right at MJ. He was easily the biggest guy there, must have been close to seven feet in height. She didn’t know if she should feel safe or more intimidated than ever. Just the rest of these thugs, she couldn’t look away from him either.

He called them off but that doesn’t mean he’s a good guy! MJ said to herself. Knowing someone like him it just means he wants you all to himself.

Then he fell to one knee right in front of her. She barely had anytime to process how to respond to his gesture before he snatched up her hand in his and kissed it. She was frozen, he kept his lips on the back of her hand longer than she intended while she heard some of the people who had just been harassing her making low ‘Oooh’ sounds and saying ‘Damn.’ She was just about to say something but then he let her go. She withdrew her arm, her face flushed in spite of herself. She knew it was just the awkwardness of the situation, but that didn’t make it any better. That innocent gesture after what happened to her before cut her deeper than what that other hooker just did.

“What brings a pretty thing like you to this humble abode?” It wasn’t the first time he had seen MJ before, he always hung around the nicer parts of town scouting for local talent whether it was checking out magazines or just looking at pretty girls before. But he never expected her to actually be here. She was easily one of the finest women he had laid eyes on and more than a few times he had sent a few of his guys to try and coax her into becoming one of his girls. They always came back with black eyes, courtesy of her boyfriend. He had no idea that Peter Parker was Spider-Man but even then he had seen that hero by her side more than a few times. He knew it would only be trouble.

“Making rent,” she said, looking away from him. She refused to make eye contact with someone like this or give him anymore attention than she wanted to.

“So you turned to the oldest profession, huh?” He towered over her, her head just came up to his stomach, but clearly she wasn’t intimidated by that one bit. Not with the glare she gave him. “In that case, allow me to oversee your guide into this new way of life. What do you say?” Then he took out a tissue and gave it to her. She snatched it from his hands and cleaned her lips of the cheap lipstick that had smudged her face.

She looked back at the others behind her. After the way they came for her, she knew that they’d only be trouble. She looked back at him. “You’re not going to try and keep me from leaving, are you?”

He looked at the ones that had harassed her, then back at her. “Of course not. This is your decision, after all. But I am true to my word. Work for me and you’ll get what you want.”

“Fine.”

“Good, good! But...” He circled around her and she winced from being looked at like that. He might have been a nice pimp, but a pimp was still a pimp. Then he was right in front of her again. “Maybe we should find you a change of clothes.” She didn’t say anything, but he could tell she didn’t like it. “Oh don’t be like that. I think you’re dressed just fine. But...” He leaned down to look at her so that his face was inches away from hers. “It’s not ho material.”

“Okay...” She backed up away from him. The others behind her were snickering. “Let me show you my preferred wardrobe. Then I’ll have you out on the streets.”

MJ was out on the sidewalks wearing a miniskirt and a little tank top. On the other end of the streets, her new pimp was in a car watching over her. He said it was for her security, a little favor he always did for his new girls on their first night. But she never felt more uncomfortable.

The least of which because a car stopped right up to her. The window opposite the passenger’s side rolled down. She slowly walked on over.

It was an older black guy, much have been in his sixties. Streaks of white in his hair, smiling right at her. “Hey cutie. You up for some fun?”

“Um...”

“Because I am.” He shamelessly fondled his crotch and she saw him pitching a tent. She swallowed a lump in her throat. She had decided to do this. But she was still at a loss for words.

“Do you ... do you have the money?”

“One hundred dollars for ten minutes of your time.” He have her a big toothy grin and flashed the benjamin right out. She needed five hundred bucks to help make things even and that wasn’t even half of what she needed. But she was desperate.

“A-alright...” she said. He opened up the door and she got inside, shutting the door behind her. His weathered hands felt up her long legs and she was surprised by how weirdly turned on she was getting. She barely had any time to react before he kissed her right on the lips. He wasn’t being rough like the hooker but there was no denying what he wanted, and before she knew it, he opened his mouth to let out his tongue.

This time, she knew she couldn’t resist if she wanted to earn that money. She didn’t try and pull away from him. She slowly opened up her mouth to welcome his tongue and he was more than happy to capitalize on the situation, shoving it right in. It was her first instinct to pull back but the instant she made to, she remembered why she was here. She didn’t resist.

As she stood there taking it, he kept on feeling her legs right up. He loved the soft skin of her thighs and moved them closer until they were right up her miniskirt. His fingers were on her panties, feeling up her crotch, while he kept on digging his tongue all around her mouth. Wanting to get this over with as soon as possible, she started kissing him right back.

That same weird heat hadn’t stopped filling her right up. Her panties were getting wet from how much he was feeling her up and the ferocity of his kissing. There was nothing gentle about it, but this being first time as a hooker and his abrupt sloppiness was something else.

He had gotten his fly unzipped, revealing his penis. She heard the zipper being undone and backed away from him, knowing exactly what that meant. She looked at his penis, hard up and pointed right at her. She couldn’t believe she was actually going to do this.

But he didn’t sense any of her apprehension. He liked the way she was looking at it. still lightly brushing her crotch with his fingers, he thankfully put on a condom. MJ realized that even with the kind of men who liked her new vocation, prostitutes had that kind of reputation. She didn’t know whether to thank him or be disgusted with herself.

She didn’t have much time to think on it. He edged on closer to her seat and pulled down her panties. He hummed pleasantly to himself feeling her hairy muff, and dipped his fingers right into her twat. She froze up feeling him touch her there, and he edged them further on it, feeling around inside before he took the digit back to his mouth and got a taste of her juices. He beckoned her to come forth with that same finger.

Ready to get it over with, she took initiative herself this time and moved so that she was hovering right on top of him. Grinning at this prospect, she grabbed her hips and directly moved her down on top of him. She grit her teeth at their joining, his dick filling her right up.

But she was inert on top of him at first. He didn’t notice it at first but when she wasn’t responding like he wanted her to, he increased the rate of his pumping. She was glad that he was wearing a condom. Not just because of the nature of this profession, but also because she didn’t want him to feel just how wet she was.

Still, he wasn’t doing her bareback but he knew. That alone was enough for his satisfaction. She couldn’t do much but sit there on top of him yet she started moving back against him. She told herself that it was just to meet his penis pounding inside of her, but he knew the truth. Leaning forward, he pulled down the front of her tank top with his teeth and started sucking her tits. She tried to held in her voice, but even if she wasn’t being as loud as he wanted to, he could hear her little whimpers.

He grunted and came inside of her. MJ gasped from his cock tensing up inside of her and releasing his cum. Even with a condom on, she felt his cum hot blowing up inside of her and as expected, he was fucking her even harder as he kept on releasing his spooge. All she could do was take it.

Even with him being an older guy, he was being relentless with her. She had to grab hold of his shoulders to keep herself steady as he kept on ramming her pussy. She turned away and bit her lip from an unwanted and unexpected orgasm hitting her. She couldn’t fight her whole body shaking up as she held onto him harder to keep herself steady from her twat tightening onto his dick. Fortunately he was too lost in his own nut to actually notice.

Finally, he was done. She got off him just so he wouldn’t get anymore ideas as well and to be spared the humiliation of him lording over that he made her cum. He threw his head back and laughed before he took off his condom filled up with his jizz and threw it onto the streets. He was almost breathless with how good he felt.

“So where’s the money?” she said curtly.

He suddenly looked back at her. He looked away nervously from her, such a beautiful woman angry with him after cumming so hard left him speechless and for a few moments he couldn’t think straight. Then he looked at her again. “Well there is one more thing you can do for me.” He pointed his dick at her, stroking it. “Go on and give it a kiss!”