It wasn’t worth the risk to actually try, but it sure was one hell of a fantasy. Not that he needed any help with thoughts to turn him on these days, but even after what he’d been doing Saturday night, it was Megan that he thought of in the shower afterwards to release his built-up tension.

  Sunday’s appointments were not quite as exciting. Both the first two women he went to see were very simple calls with one just getting a quick spanking and the other getting blindfolded and teased, but all over the clothes. The third visit had involved more interaction, but it still wasn’t as much fun for Nick. Her name had also been Jen, but unlike the Jen he was looking forward to getting back to on Friday, this Jen wasn’t as appealing. She had an incredible body, and Nick was quite excited by her picture when he pulled it up initially, but so much of a woman’s sensuality came from the way in which she carried herself. Unfortunately, this Jen had all the mannerisms that Nick would expect from a horny troll.

  She didn’t even wait for Nick to tease or undress her. She stripped herself down the minute Nick removed his jacket, and was way too desperate. It was certainly another opportunity where Nick could have had his way with her, but he was looking to get things over with as quickly as possible. He gave her a spanking and got the hell out of there. He’d never met a woman who had such incredible natural beauty, but left him with no desire to take it in at all. Hopefully the look on her face as she sat naked in her dining room as he walked out the door without even putting his jacket back on wouldn’t turn into a bad review.

  Monday brought Nick’s return to work after his Thanksgiving holiday. He was blown away at just how hard it was to concentrate. Thoughts of his other job, and memories from his weekend activities were taking up the majority of his focus. Having Josh and Adam there didn’t help at all. The three of them worked in the same department, and even though their cubes were an aisle apart, they found several times to come over and try getting more juicy details from his weekend.

  The most difficult part of his day was the staff meeting that Megan led that afternoon. It was hard to focus with her standing up in front of the conference room on the best of days, but his newest fantasy made it that much harder. Her tits were the subject of many water-cooler debates among the men of the office. They couldn’t decide if they were real or fake. Nick’s money was on fake, but if they were real, they were God’s most perfect creation. The pants she was wearing hugged her ass perfectly too, and the lack of panty lines brought the image of her in a thong to mind. There was no telling what the meeting had been about. Nick hadn’t heard a damned word.

  That was the tone for most of that week for him. If it hadn’t been the holidays, a quieter time for their office, he would have been in serious trouble. Thankfully, things were slow enough that he was able to keep up pretty well.

  He’d expected Tuesday to be even more of a challenge, as he had the afternoon appointment to think about, but it was really the party at the end of the week that had him most worked up. Time was running out and he still had no clue if his sister would be there, or how he’d find out without it sounding forced. His visit that afternoon was to a dentist’s office and it was none other than the dentist herself that he was there to see. The app had referred to her as Kylie, but the receptionist blushed when she said, “Dr. Grover will see you now.”

  Whether she’d been the one to order the visit, which seemed unlikely given the cost, or just involved with whoever had, Nick was certain she knew what he was there for. The look on her face was enough to make him think she was aroused just from the thought of what he was about to do.

  When he walked back into the back side of her office, the assistants who were there all giggled and Dr. Grover turned to see him and rolled her eyes. That was a new response!

  “Again?” she asked looking at the other ladies who were all laughing louder now.

  Even the receptionist had come back now and was standing beside Nick to see the doctor’s response.

  “Alright, what’s it going to be thins year?” she asked, looking at Nick with her head cocked to the side.

  Nick thought quickly to try and keep the act going, and said, “You’ve been on the naughty list before, haven’t you?”

  “Yes,” she said, shaking her head. “I must be a mean boss, because these ladies seem to want to add me every year.”

  “Well I think we might need to make sure you learn your lesson this time then,” Nick said with a smile.

  He set his bag down and removed his jacket before walking up to Kylie Grover who was looking at him suspiciously.

  “They asked that you be spanked, but I suspect you’ve been spanked by a Secret Santa before and that it didn’t do the trick. Perhaps there was too much interference last time.”

  She looked back at him curiously before the meaning of his words registered.

  “Oh no…” she said. “Nice try, mister, but I don’t think so.”

  “Kylie,” Nick started, using her first name intentionally. “You need to do something to show that you’ve learned your lesson. I think these ladies want to see you finally learn your lesson. What do you think ladies? Should she pull those pants down a little and let me give her a real spanking?”

  All three women cheered. They were clearly all good friends, and Dr. Grover just blushed and shook her head.

  Nick thought for a moment and then said, “How about this… If you’re pants come off, mine will too. That’s more than I was asked to do, but I’ll play if you will.”

  The receptionist’s jaw dropped. She turned back to her boss and practically begged. “Come on! Just show him your ass and let us get a look at what Santa’s got hidden under those baggy pants of his!”

  Kylie’s eyes were wide as she looked back and forth between Nick and the woman next to him, but with a flushed face, she shook her head and unbuttoned her jeans before wiggling her hips and pulling them down over her ass. Her panties were very thin in the back; royal blue with black trim. Knowing what was coming, she’d already bent over against the wall and was giving him a very nice view.

  True to his word, Nick undid the tie on his own pants and let them fall all the way to the floor. One of the assistants gasped, causing Kylie to look back too, and her eyes went very wide at the sight of his cock, clearly outlined by the very tight boxers he’d bought specifically for this job. No matter how many times he heard a woman say size didn’t matter, the look in a woman’s eyes at the sight of a massive cock was proof positive that all such talk was a lie.

  Stepping up behind the dentist who was bent over next to one of her chairs, he rubbed his hand over her smooth, tanned flesh and then delivered the spankings he was being paid to deliver. He used a bit more force with her, sensing that she’d like it. Sure enough, she was holding back sighs by the time he was done. The other women’s eyes alternated between the red handprints on their boss and friend’s ass, and Nicks cock which had surged to full size as he spanked a woman in front of an audience for the first time ever.

  It had been quite the experience, even if it wasn’t as exciting as some of the others over the holiday weekend. Leaving her office, he wondered if he’d get to punish Lisa, the target of Friday’s party, in front of her friends as well. Maybe he’d be able to have even more fun, and punish some of the other women at the same time. Only three more days to go!

  Wednesday’s appointment was cancelled early that morning and the rest of the week seemed to just buzz by. It wasn’t until Thursday that Nick finally found out whether or not Laura would be at the party he was scheduled for the following afternoon.

  She’d stopped by to pick up something their parents had included in a package to Nick, and the two talked for a few minutes. To his horror, his step-sister was going to be there. He’d asked if she had any special plans for the last day of the week and she’d shared that her office was doing a bachelorette party for one of the girls after work. It looked like she was about to say something else about the party when she stopped herself, and that only confirmed that it was, in fact, the same party. She’d probably been warned that it would be a ‘not safe for work’ party, but that was hardly something to tell your brother.

  Now that he knew for sure, Nick had to make a tough call. Should he find someone to take the party for him? He was a specific request so it might not work, but he could try. Surely if he explained that he discovered that his sister would be in attendance, the company would understand. On the other hand, he didn’t want to lose out on the money. Parties were a huge money maker.

  Another option would be to tell his sister what he was doing. He could beg her to find a way out of going to the party. He could even offer her five hundred bucks to keep his secret. It was risky, but it would let him cash in on the opportunity. It might work, but the thought of telling her what he was doing didn’t sit well, and he couldn’t imagine having that conversation with his parents if she decided to tell them anyway. It wasn’t something he actually thought she’d do, but it was certainly a risk.

  There was one final option. He’d been thinking so damn much about the fantasy with Megan and how he could try disguising himself, that he’d actually found a Santa mask that might work. If he ordered it on overnight delivery, he could get it in time for the party and just deal with the fact that his sister was unknowingly checking him out. She wasn’t the woman he’d been paid to go after, so it wouldn’t be any more than seeing some guy flashing his package and spanking or teasing another girl in front of her. Laura would never know, and Nick was actually finding the idea arousing.

  It wasn’t something he’d ever thought about. His sister was certainly attractive, and he’d been fortunate enough to catch her nearly nude a few times growing up, but he hadn’t thought much about her given their relationship. Thinking about her getting turned on by him was sending a rush to his cock though. His mind wandered to her playing with herself afterwards while thinking about him – all without ever knowing it was him. He was suddenly standing in his kitchen with a raging hard-on, just from the thought of it.

  That was all it took. Once he realized how much the taboo thought excited him, he was all in. He immediately pulled his phone out, and placed the order for the mask. He was going to dance around in revealing boxers, spanking other women, and perhaps even stripping down to nothing – all right in front of his step-sister, Laura. Playing out the scene in his head, Nick headed into his bedroom and found that he had a new fantasy to get off to. If just the idea of it was this thrilling, how was he going to feel the next afternoon, when it was reality? He certainly wasn’t going to have any issues getting a hard-on to show the ladies!

  Thoughts about the party did not fade after his orgasm. Even after a second orgasm that night, he couldn’t get the thoughts out of his head. It kept him up late into the morning and he did something Friday that he’d never done before. Nick called in sick for work to get some more rest before the party. Good sleep was still hard to come by, but he at least enjoyed staying in bed a few extra hours. Since he was home when the mask was delivered, he tried it on. It was perfect. The eyes were cut wide and his vision was hardly limited at all. It was also very secure with two thick straps on the back so it wouldn’t fall, even if he moved his head suddenly.

  As the morning faded to afternoon, he went through his plan a few times. He knew that the party would be different than his previous jobs. With more women, and probably alcohol, thrown into the mix, chances were slim that things would go according to his plan. He knew he was quick on his feet, but he still wanted to have a few ideas of different things he could do to make the experience memorable. He packed up his stuff, changed into the suit, and checked the mask in the mirror one more time, assuring himself that no one would be able to identify him in it.

  He drove to the building, not needing the address since his sister worked there, and donned the mask that would protect his identity. Nick checked in with a very amused receptionist at the front table and signed in with a fake name. Jen knew his first name so he didn’t fake that, but he gave himself the surname Smith for this visit. He was escorted back to a conference room, and found it filled with women when he arrived. One of the ladies got up and locked the conference room door once the receptionist had left. It was time.

  Nick started to put his plan into motion, but it would be all of two minutes before it all went out the window. It was going to be wild all right!

  Chapter 9 – Jen Young

  To say that my entire week had been spent thinking about Nick would have been an overstatement, but only a small one. His visit last Friday had been something that was going to stick with me for a while, and I sincerely hoped I could manage to turn today into something worth following it. The timing of Lisa’s bachelorette party was perfect. The entire group of women from my department had always been naughty and this was the perfect way to share some of the incredible man who’d visited me with everyone else.

  I told everyone why I was inviting this particular guy, so they all knew what he’d done to me, but he didn’t know that. I figure he probably knew I’d requested him, but that wasn’t a certainty. Now it was time. The receptionist had texted me when he arrived. He’d be back here any moment for all the women to feast their eyes – and perhaps their hands on. There was no way to know exactly how this was going to go, but I knew exactly where I wanted it to end. If I had my way, it would end with me bent over the desk in my office down the hall, while Nick gave me every inch of that incredible cock. I’d only gotten a glimpse of the head last week. It was enough to drive me wild all week long!

  The conference room door opened and I saw the bright red outfit right away. The second thing I saw was the mask. Why was he wearing a mask now? Perhaps it was to hide his identity in front of a larger group of women. Being seen by one or two women a day was still a risk, but being seen by the twenty who were here all at once was probably more than he was willing to take. No matter, it was a good mask and it would do nothing to hide his body! Jayla got up and locked the door as soon as Susan had left him behind. He walked to the front corner of the room and set his bag down. Just as he’d done in my home, he slipped his jacket off, revealing his incredible physique. Salina liked what she saw, and let out a cat call, which got laughs from everyone in the room.

  “Where’s the special lady?” Nick asked, turning back to us with candy canes tucked into the waistband of his pants.

  Several of us pointed to Lisa, who was at the head of the table opposite Nick. I could see the sides of his face rise as he smiled. He had a big, infectious smile that I wished the other women had a chance to see. I’d get that mask off of him later, but I’d let him keep his secret in here.

  “Well she’s gotta get the first treat, now doesn’t she?” he asked, walking around the table toward her.

  He lifted a leg up onto the arm of her chair and leaned forward as she reached up and simply took one of the candies from him. Lisa was far too shy. This might help open her up a little, but I knew that Nick wasn’t going to get a lot of excitement from the star of the party.

  Once he’d begun with her, he started making his way around the table, stopping for every woman to get a cane out of his pants. Some of the women simply slid one out, but many got a little naughty right off the bat and pulled theirs away from him, stretching the band of his pants away from his body as they peered down. An, “Oh my,” from Nicole told me that he might have run them underneath the band of his boxers too. Was I about to get a better look at that cock I wanted so badly?

  He finally arrived, and I said, “Hello again.”

  “Hi Jen, have you been more well-behaved since I last saw you?” he asked.

  I grabbed one of the candy canes, and flipped it upside down in his pants before pull it out and using the hook to pull the band of his pants, and yes – his boxers too, out from his body, as I looked down and got a decent look at his cock. He was already semi-hard, and I knew we’d get him all the way there in no time. He reached down and unhooked his pants, shaking his head disapprovingly at me.

  “It looks like you might need another visit to teach you a lesson,” he said.

  “I was hoping you could stay late and teach me something tonight,” I whispered back up at him, knowing full well the women on either side of me heard.

  When he moved on to the next chair without a word, Laura, the newest girl on the team who was sitting to my right, looked at me with her eyes wide and mouth agape.

  “I can’t believe you all do this in here!” she exclaimed.

  “Told you it was an NSFW work party!” I replied with a big laugh. “I hope you can handle it.”

  “Hell yes,” she nearly shouted and Nick looked back over his shoulder right at her. I could see the big smile in his cheeks again.

  We’d snuck wine into the office, and most of us were already two cups in at this point. Laura was clearly already having quite a good time.

  Nick had nearly made it all the way around the table when he got to Taylor. Hers was the last candy cane, and rather than pulling it out with her hand, she grabbed the top with her teeth, and then pulled his pants down with a swift tug. Never breaking his role, Nick shook his head, but he stepped out of the pants and tossed them over toward his bag. He might not have intended to lose them so quickly, but that bridge was crossed, and he was rolling with it.

  “I hear you’ve been naughty this year, Lisa. Do you know what I have to do to naughty girls?” he asked.

  “Give them coal?” she asked sheepishly.

  “Oh no!” he said with a laugh. “Jen likes to call me Santa,” he said glancing over at me and drawing the other women’s eyes to me, all wide at his confirmation of some of the story I’d told them. He continued, “but I am really just his helper. I punish naughty girls to help them get back on the nice list. Do you want to be on the nice list?”

  Lisa looked around, clearly WAY outside her comfort zone. “I guess so,” she said in an overly tentative way.

 

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