Scott had hired Anne as a part-time office assistant during her freshman year of college. At the time, the entire office staff were middle-aged women and while they were efficient in their work, none of them would ever be mistaken for a beauty queen. Scott was use to working with young attractive people in his previous position and was determined to liven up the place with every new hire. Anne was an easy choice. At 5' 7" and approximately 130 pounds with shoulder length blonde hair, she was stunningly attractive, but she quickly proved to everyone that she would be more than just eye candy. She was far more mature than most college students and her outgoing, down to earth attitude became contagious and everyone took an immediate liking to her.
Scott absolutely loved having Anne work for him. Not only was she cool to talk with and great to look at, but as time went on her responsibilities increased and she became one of his most valued workers. So much so that by the time she was about to graduate, it was obvious to everyone that she was his go to person whenever he needed something done. As a result it was no surprise to anyone that when she graduated, he hired her as his full-time lead assistant. The strange thing was that there was not the usual office resentment or animosity from any of her co-workers.
Anne was now working even more closely with Scott and the better she got to know him, the more she realized that he wasn't just a great boss, he was also a great guy. He was very easy to talk to and she found herself telling him things she didn't even tell her closest friends; including private things about her up and down relationship with her boyfriend.
Scott didn't quite know when or how his relationship with Anne had transformed from boss/subordinate to more like close friends. With he being 36 and married with two small kids and she being a 22 year old recent college graduate, he seemingly wouldn't have much in common with the young blonde beauty. But nevertheless, there was an undeniable bond developing between the two of them. A bond that he was sure she felt as well. Afterall, she was telling him private and intimate information about her relationship with her longtime boyfriend and while he didn't disclose many personal details about his home life with her, he did talk to her about things he would never discuss with any of his other subordinates.
One particular topic of discussion that he was recently having with her involved the things that he would do while on business trips. Scott would typically take a couple of business trips each year and over time he and a core group of colleagues from other work sites had developed somewhat of a tradition of working hard and partying hard while on these trips. Regardless of the city or trip agenda, at some point there was sure to be time set aside for some serious alcohol consumption and a strip club or two intermingled in the mix.
In fact these trips and the occasional trip with the guys had become Scott's sole outlet for reliving the days of going out and having fun just for the sake of having fun. Although he loved his wife very much and they had a pretty good relationship, once they had kids things changed. Some for the better. Some for the worse. Having children brought a whole different kind of joy to their life, but at the same time, he missed being able to go out as much as they did before and he definitely missed the amount of sex they use to have. But he's held out faith that once the kids get older things can gradually go back to the way they were before.
While waiting for that day, he decided years ago to make the most of these trips and although he had not yet gotten to the point where he had actually fucked another woman he had come close several times and done many other things of which his wife would definitely not approve. In his mind and that of his out-of-town running partners, they had always justified their actions by saying "What goes on out of town ... stays out of town."
Scott was careful not to tell anyone in his office about the antics that went on during his trips, but, it had come up with Anne because she was always telling him about how much fun she has going out drinking. Not wanting to be outdone by his younger subordinate and for some reason feeling a need to impress her, he told her some stories about his trips. He didn't dare tell her everything, but he was pleased that she was genuinely impressed and interested in the things he did tell.
Scott was use to being around beautiful women, but as he spent more time with Anne, he realized that there was something special about her. He also realized that their tone and demeanor to each other in the office had further progressed from being friendly to more flirtatious and was definitely having an effect on him. He had always admired her good looks; but now he was looking at her with wanton eyes. His attraction to her was growing each day and as much as he tried to fight it, he couldn't ignore the hard-ons he would get just by looking at her or thinking about her. What made things worse was that although he couldn't be completely sure, he thought that she was starting to feel an attraction towards him as well. Something had to give. That's when it hit him, one way or another he had to take Anne with him on his next business trip.
Anne could not believe it when Scott told her he was taking her with him on his business trip. When he had hired her he had never mentioned any overnight travel, but since she knew how much fun his trips had been, who was she to argue. Besides, being the 22 year old partier that she was, she was really looking forward to an all-expense company-paid trip where fun was usually the name of the game.
There was actually no real business need for Anne to go on the business trip, but Scott had convinced his boss that it would be a great learning experience for her. However, one of the conditions of her going was that they would have to save on cost by driving instead of flying. Since it was less than a 5 hour drive and it would allow them to stay an extra night, Scott didn't mind at all.
The 5 hour drive really went by quickly as the two talked nonstop about any and everything except work. Scott told her a few more stories from previous trips and reminded her that whatever goes on out of town stays out of town.
After checking in and freshening up, the two meet in the hotel restaurant for dinner and the topic of conversation turned more personal.
"Tell me something Scott. Why did you bring me with you on this trip? You've been coming on these trips for years and you've never taken anyone else."
"I just thought it would be a good learning experience for you," Scott said unconvincingly as Anne gave him a bullshit stare.
"Is that what you told your wife?"
"No, that's what I told my VP. I didn't tell my wife shit."
"You are so bad. Why didn't you tell her? Would she be pissed?"
"I don't think she'd be pissed. But there was nothing to be gained from me telling her and I've learned over the years that some things are left better off not said. And trust me, the less I tell her about these trips the better."
"You make it sound so exciting. Do things really get that wild?"
"Well Annie my dear, all I can tell you is that there's a reason why we say, what goes on out of town, stays out of town."
The remainder of dinner the two had an enjoyable evening and did a little work to prepare for the meeting the next day.
After arriving to the meeting site, Scott was disappointed to learn that only one of his usual colleagues was at the meeting. What made things worse was that he had to fly back later that day and Scott would be on his own to take the group out for dinner.
That night Scott took the entire group out for dinner and drinks. As the highest ranking person in the group, he didn't feel comfortable drinking or partying too much with this new group of people he didn't know very well. Things were definitely not going the way Scott had hoped.
"I'm sorry tonight wasn't a very exciting night." Scott said to Anne as they were heading back to the hotel. "That's not the usual crowd I hang with."
"I'm glad to hear that. You had me worried for a minute." Anne said with a bit of relief. "I kept thinking that if this is what goes on, not only have you forgotten the definition of fun; but you could tell your wife every little detail and instead of being pissed, she'd probably feel sorry for you."
"Oh you've got jokes now. Well I tell you what, after tomorrow's meeting it's just you and me and I'll show you first hand how I define fun. That is, of course, if you think you can handle it."
Always up for a challenge, Anne confidently replied, "I can handle anything you've got."
The next day Scott could barely focus on the meeting at hand. All he could think about was making sure that he showed Anne the time of her life later that night. After so much talk about how wild his trips were in the past, there was no way he was going to return back to work without showing her a good time. He felt like he would lose all credibility with her and more importantly he did not want to pass what may be his one opportunity to party with her.
After ending the meeting and saying his goodbyes to the rest of the group, Scott took Anne to dinner at a very expensive restaurant where they both had several drinks.
"Are you ready to take it up a notch?" Scott said as they were finishing dinner.
"I told you last night, I'm ready for whatever you got."
"All I can say is be careful what you wish for. And for the record, for the remainder of this trip, I am no longer your boss. I'm just a guy who's going to show you a good time."
"No offense but that remains to be seen, isn't it. Besides, I'm sure there's a thing or two that I could show you about having a good time as well."
"You talk a good game Anne. Here's to a great night."
Scott had been thinking all day about where he would take Anne. He knew he was going to take her to a strip club. That way even if nothing developed between the two of them, at the very least he'd get to see some naked ass. It wasn't until they were leaving the restaurant that he thought of the perfect place to go.
Rick's Cabaret was 3 clubs in one. One section was a female strip club, one a male strip club, and an area between the two called the Lounge which is a typical dance club. After a few drinks and dancing in the Lounge, Scott and Anne decided to separate to see what was going on in each of the strip clubs and then meet back in the Lounge.
As usual Scott was having a good time in the strip club. It wasn't very crowded because it was a weeknight, but the drinks were strong, the women were hot, and the lap dances were good. He was having such a good time that he lost track of time and was late meeting Anne back in the Lounge.
At the other end of the building, Anne was not having as good a time in the male section. She had only been to a male strip club a couple of times and each time were with a group of girls. Being by herself with just a few other women in the club made her feel very uncomfortable. So much so that she didn't stay very long before returning to the Lounge to wait for Scott.
"Sorry I'm late." Scott said to Anne as he sat beside her back in the Lounge.
"No problem. From the grin on your face, I take it you had a good time." Anne replied. "There must be more going on in the girls section because the mens side was dead."
