Secret Santa's Naughty List Read online

  After a little dance in that position she dropped her ass down into his lap and leaned back into his body. Whether she meant to or not, she’d landed on him with his fully erect cock running right along the inside of her ass cheek as it hugged his leg. Nick knew he was well endowed and there was no doubt that she could feel his stiffness pressing into her. She only confirmed as much when she tossed her right leg over his and slid her covered pussy across the length of it.

  It hadn’t been an accident. She was now grinding down on top of his cock, pressing her body into it and beginning to moan as she did. She had her back arched and was leaning back into his chest letting him look straight down the front of her body at her heaving tits. If she kept this up much longer, he was going to cum in his pants.

  “You’re huge,” she whispered up at him as she kept grinding. “I’ve never felt anyone as big and hard as you. Can you keep a secret?” she asked.

  Nick could only manage to get out an, “Uh huh.”

  “I’m not supposed to let you do this and I don’t ever break the rules, but it feels so good. Could you take it out so I can see it? I bet this would feel better too,” she said, as she shifted her body, allowing her ass to slowly and deliberately grind against the entire length of his cock.

  There was no time for Nick to consider whether or not this was a line to get him going or the truth. For all he knew she said the same thing to every guy so they wouldn’t judge her as a whore. He didn’t care. In that moment, nothing was going to stop him from taking full advantage of her offer.

  She turned her head to look at him over her shoulder, biting her bottom lip, the most convincing need he’d ever seen in a woman reflected in her eyes. All he had to do was nod and she lifted her weight and shot her hands to his pants to get them undone. Without any attempt at hiding her actions, she ran one hand the entire length, base to tip. Once his pants were open, she got up and turned around. She made a motion like she was going to grab his dick out, but then shook her head and started to pull his pants right off. No issues with Nick there!

  With the tip sticking out just below the bottom of his boxer briefs, the woman marveled at his size. She pulled the waistband down and pulled his cock out the top of it with her bare hand. Feeling her hand touching him sent a shiver through his body, and she giggled when she saw it.

  “Someone’s enjoying himself,” she said with a laugh.

  With that, she stood back up, turned her ass toward him, and dropped back down on his cock, letting it slide right between her legs. He could feel her cool flesh on the sides as she slid back and forth along his length. He was so excited that he was leaking now, spreading his natural lubrication between her cheeks, and making the feeling of running between them that much sweeter.

  Moans started to escape her lips, leading Nick to feel bolder once more. He reached around her to take hold of one of her tits. She sighed at the touch, but did nothing to stop him this time. In that moment, Nick felt certain he was going to get to fuck this girl. It was clear that she was genuinely losing control; and believing, whether he was right or not, that she was uniquely turned on by him in this situation, only made it that much better for him. With his hand now kneading the soft flesh of her breast, with his index finger and thumb tweaking her nipple on occasion, he grabbed onto her hip with the other hand and started to guide her along his cock at his own pace.

  Her moans were quite loud now and he wondered if he’d actually be able to get her off through her panties before they even went any further. She wasn’t going to give him the chance to find out. Without saying a word, clearly lost in the moment, she leaned forward; not enough to force his hand off her breast, but enough to change the angle she sat on him with. As she leaned forward, she reached down between her legs, her hand brushing the tip of his cock in the process, and pulled her panties as far to the side as she could. As she continued to slide her body along him, he could feel the heat and wetness of her pussy running over his cock.

  He watched the rhythm of her body as she gyrated on top of him. She felt so good as she stroked him with her pussy lips, but he couldn’t help hoping she’d do more. As if she had read his mind, she pushed her hips back and pushed down onto his cock, letting him fill her with every last inch all at once. He slid in easily despite her feeling pretty tight around his size. This incredible woman had just crossed the final line and taken his cock. He was fucking the hottest woman he’d ever laid eyes on and he didn’t even know her name. That only made it hotter.

  The mystery girl rode him with fire and passion and was screaming out through an orgasm in no time at all. The feeling of her pussy, the sound of her screams, and the amazing sight of her tits bouncing as she leaned back, set Nick off and he exploded inside of her.

  “Holy shit!” Nick exclaimed as she climbed off of him. “That was incredible.”

  “It was,” she agreed breathlessly. “But seriously – you can’t say a word. I never do that and we have really strict rules.”

  Maybe she really did have rules that she had only broken for him! That thought had added many layers to the excitement, and he knew he would get off thinking about it in the future.

  “I won’t say a thing – IF you agree to see me again,” he said, trying to spin this encounter into even more.

  “I would honestly love that,” she said with a genuine smile, “but there’s no way we’d get away with it. They are very careful to watch for stuff like that. Even if we ‘accidentally’ ran into each other sometime, they’d find out. They keep track of every customer we have.”

  “That sucks,” Nick said with disappointment.

  “Trust me! If there was any way I could get a round two of that, I’d make it happen. You are something else. In fact…” she let her words trail off into thought.

  “What?” Nick asked.

  “I was just thinking that you’d be perfect for this gig. They’re always looking for men. Plenty are willing, but the requirements are tough to meet. You’d work perfectly. This season is basically over, but if you were interested, I could get you an interview for next year.”

  “And what would I do exactly?” he asked, trying to hold back a laugh. “Would I dance for women? Not sure I’d be all that good.”

  The girl, whose name he still didn’t know, just laughed. “No, no… nothing like that. The men are asked to do very different things when they get calls. Trust me, you’d be perfect.”

  “I think I’m good,” Nick said, not wanting to be rude, but having no interest in pimping himself out with strip shows or whatever else he’d be asked to do.

  “Well, before you rule it out completely, let me just tell you that you’d make a hell of a lot of money with your body. Top requests make more money in the season than most people do all year. Don’t take this the wrong way, because I live around here too, but this is not the zip code I normally work in.”

  “How much are you talking about?” Nick asked, feeling like a tool for wanting to know the specifics.

  “I’m not supposed to say, but let’s just say that two hours with you would be a triple figure payout, and the first number would not be a one.”

  Nick’s eyes went wide. More than two thousand dollars for two hours??? And she wasn’t even supposed to put out. That was a hell of a lot of money.

  “That’s what I thought,” she said at his reaction. “Give me your card and I will have someone get in touch.”

  Nick fished his wallet from his pants off the floor while the girl who finally introduced herself as Cassie got dressed back in her sexy outfit. She took the card and gave him a kiss on the cheek before fixing her skirt one last time, picking up the speaker and her bag, and heading out. It had only been ninety minutes and Nick was tempted to ask about the rest of his time, but given what he’d gotten from her, he didn’t think that was necessary. Whoever had signed him up for this deserved a medal, and he was very intrigued to learn more about just what he’d have to do in order to make that kind of money. He could pay off a lot of debt
with that extra cash!

  Chapter 2 – Season’s Greetings

  The light changed before he could get his app working again and he cursed under his breath. It was his first gig and he was going to be late and blow it. Why did downtown have to be so fucking hard to get around? He dropped his phone in his lap, and was relieved when the familiar female voice finally returned and told him to continue straight for another half mile. He wasn’t lost! Realizing that he’d been going slower than the speed limit as he tried to get his bearings, he sped up before getting honked at, and saw the building up ahead. Saint Securities. Nick was trying to stay calm, but what he was about to do was starting to freak him out.

  It had been nearly a year since his unforgettable experience with Cassie. She had left an impression, but true to her word, he had never run into her again. He’d hoped that she wasn’t really that worried about her rules; after all, she’d already broken a pretty big one when she’d decided to fuck him. Sadly, she never ‘accidentally’ bumped into him and all he was left with was the memory of her sizzling body, and the desire to get into whatever business she was in himself.

  He held out hope that someone would reach out to speak with him, but after six months he’d given up, figuring she’d forgotten about it, or it just hadn’t panned out. Then, late one July evening, he got a phone call from someone from N.L.I. Nick had no clue what they were calling about until they gave him the full name. Naughty List Incorporated. Cassie!

  It wasn’t Cassie on the phone, but another young girl who invited him to come into their office in the city for an interview. It was really happening. He cleaned himself up and wore his nicest suit to the interview. When he arrived, he felt like he was auditioning for a modeling agency or something. The room was packed with the most beautiful people he’d ever seen in one place. Every guy was clearly muscular, every girl a natural beauty, and one by one they were being called in for what seemed to be about a fifteen-minute interview.

  His excitement for the job faded when he realized how much competition he was going to have for the job. How many people could they really need to do… well whatever it was that the men did for them. Cassie had said it was different, but he had no idea what that meant. When he searched the company online all he could find was the webpage that allowed users to sign their friends up for the nice list (men) or naughty list (women). He’d tried to see what the naughty list was, but they wanted a credit card before even showing you the menu. It seemed sketchy and he didn’t go any further. Nick figured he’d find out soon enough.

  He was called in within five minutes of his appointment time and was led into a spacious office with an incredible view of the ballfield. This was premium real estate! The company must be doing pretty damned well for itself!

  “Hello Nick,” a blonde woman in a black dress called from behind the table. She sat there with two other women and one man, all dressed very professionally.

  “Good afternoon. I brought my resume,” Nick offered holding out his folio in case they were interested.

  “That’s wonderful, but we won’t be needing that. This is not a job that your professional experience will help you land. Have a seat,” the same woman said, gesturing to a single chair in the middle of the room.

  Nick sat and set his folio down on the floor beside him.

  “So, Nick,” another woman with dark brown hair and glasses began, “I see that you are a referral from one of our elves. You were a customer of hers?”

  It was a little surprising that they knew about that given how serious Cassie seemed to have taken her breach of protocol.

  Nick nodded. “Yes. I received a very surprising visit from her last year and she asked for a card before leaving so she could pass it on. I think she could tell how interested I was in whatever it is you do. She didn’t offer much in the way of details, but it looked like a lot of fun!”

  “Do you recall her name, Nick?” the darker haired woman asked in response.

  “No,” Nick lied, afraid that he would get her into trouble if it turned out she wasn’t supposed to give her name.

  “Well, tell us what you think this role will involve,” the blonde asked, entering the conversation again.

  “I don’t really know,” Nick confessed. “The girl last year put on quite a show for me, but she did say that I’d be doing something different. Perhaps stripping for women?”

  “That is one of the options, yes,” the woman said flatly with a nod. “Are you comfortable touching other women if they want you to?” she asked.

  “I think so,” Nick said. “As long as I’m not expected to take things too far. I’m not looking to be a gigolo or anything.”

  “Nothing like that. That is against our rules. We would need you to massage women, tease them a little, and spank them. Could you handle that?”

  “Did you say spank them?” he asked, wide-eyed.

  “Yes. Women who are added to the naughty list are often signed up for a spanking. Sometimes they prefer it to be hand delivered, other times they want a paddle or a crop. You deliver to their desires. Would you be comfortable with that? You never have to take a job that makes you uncomfortable and all requests come with a picture. We’d hate to have you show up at a co-worker’s or family friend’s house. It also allows you to make sure you are comfortable with whatever that particular client might be in the mood for, within the confines of our rules, of course.”

  Nick had suspected that this might be exactly what the job would entail. It wasn’t far from what he’d experienced, but he was still shocked hearing it out loud in such a professional interview setting. He held himself together, not wanting to blush or show any signs of his excitement. He expected that they wouldn’t want anyone who was TOO eager for the job.

  “I am certain that I could handle all of that,” he replied confidently.

  “Wonderful,” the brunette replied. “Now, could you remove your clothing for us? Everything down to your underwear, if you would.”

  Nick’s goal not to blush was blown. He looked back at them a moment to see if she was kidding, but all of their faces were quite serious. He shook it off his nerves, and stood up to do as she had requested. He was wearing boxer briefs and wasn’t really going to show any more than he did at the pool in his trunks.

  He slid his jacket off and hung it neatly on the chair. Nick then unbuttoned his shirt and pulled it from his pants to let it slide off before he draped it over the jacket. All four of them, including the man, were staring at him quite intently. He could feel their gazes wandering up and down his body as they examined every inch. When he’d finally untied his shoes and kicked them off, he saw all of their eyes fix on his groin while he lifted one leg, and then the other from his pants. He folded them, and laid them on top of his other clothes. The office was dead quiet as Nick stood there in his tight, grey boxers and black dress socks while they evaluated his body.

  “Thank you,” the man said, finally.

  Nick put his clothes back on, trying not to make it look like he was in a rush. He returned to his seat and the four behind the table whispered back and forth for a few minutes before addressing him again.

  “Do you have any questions for us?”

  “What is the pay?” he asked, cutting right to the chase.

  He’d been told that some employers love that question and others hate it. There was no middle ground. For Nick, it wasn’t a matter of trying to ask the right thing, but more him genuinely wanting to know what to expect, given the kind of crazy shit they seemed to expect from him.

  “That depends on the call,” the blonde, who’d spoken with him first, responded. “Some actions cost more than others, which nets you a bigger payday. You can also get bonuses for getting requested. If you are on a shortlist – meaning that a woman wants one of three men, including you – you get a one hundred dollar bonus, whether you are picked or not. If you’re selected from a shortlist, you get an extra hundred. If we get an exclusive request for you, you get a five-hundred-dollar bon
us on top of the call fee. You can make as much as three thousand dollars for a single call if it is a premium package on an exclusive request.”

  “Don’t get too excited,” the man said, cutting her off. “We only have a few guys who make that kind of money. Most are pulling in five-hundred to a thousand dollars a call.”

  “That still sound good to me,” Nick said. “That’s all I needed to know.”

  The Brunette looked to the blonde and then over to the man and the Asian woman who sat on the other end of the table beside him. The very short, black-haired woman hadn’t said a word to Nick, but she’d been examining him the whole time and had spoken to the others during their brief, private conversation.

  “We’d like to offer you an opportunity to work for us,” the brunette said with a big smile. “Could you start right after Thanksgiving?”

  Nick hadn’t realized that she meant immediately after Thanksgiving, but he managed to break the news to his parents that he couldn’t make it home for the holiday and they took it as well as could be expected. His sister had already bailed on them to stay focused on her new job, so at least he wasn’t breaking up a family event.

  Laura had moved down to San Diego right around the time Nick had taken the Naughty List job. She’d finally graduated with her master’s that spring, and one of Nick’s buddies mentioned that his firm was hiring early in the summer. Nick set her up with the details, and was proud of his baby sister when she landed the rotational leadership position after her first interview. She had moved down a month later. The four years that separated them had kept them from being too close growing up, but she’d matured a bit more over the past few years. He’d finally stopped seeing her as the bratty sister he’d known most of his life.