NEW STORY TITLE: Sex Vacation with the Boss
My first job and Mr. Wilson propositions me.
Enjoy!
My first job out of school was working in an office. I was in my early twenties and just getting started in my work career. I was thrilled to have a full-time job and finally have money of my own.
I was hired by Mr. Wilson, who was in management. The job interview went very well, and I was thrilled to learn I was hired.
Mr. Wilson was a nice older gentleman, and he immediately began to take an interest in me. Maybe he felt responsible for me since he was the one that hired me. Maybe because I was the youngest employee. He wasn’t my direct supervisor, but he was well above me none the less.
He picked up I was on the shy side and he would always go out of his way to talk to me or compliment me on a job well done. It was just office talk, but I did notice he talked to me more than the other women in the office. He was like a father figure to me.
Our relationship was purely professional. I was very careful to behave and act professionally. This was my first full-time job, and I didn’t want to mess it up.
Over time, Mr. Wilson asked me to call him by his first name, Ben. It didn’t feel right to me, so I kept calling him “Mr. Wilson” out of respect.
I couldn’t help but notice Mr. Wilson was an attractive man for his age. He was easily in his late 40’s or early 50’s. He very much reminded me of my father, kind and gentle. He was always well dressed and groomed. He was a very classy man. He was confident and had that look of success, which is very attractive. I had no idea if he was in any kind of relationship. It wasn’t my place to ask.
The other women in the office were all older than me, and they all spoke very highly of him. He was everyone’s favourite manager.
One day, while chatting, I complained about the cold weather and how I hated winter. He responded that he felt the same way and suggested that we go to Florida for some sunshine. I jokingly agreed and said something like, “My bikini is already packed.” That was the end of it. We were just joking. So I thought.
About a week later, he called me into his office and told me to close the door. He had never called me into his office before. I was worried that I had done something wrong. I nervously sat down across the desk from him. He pulled some papers out of his drawer and slapped them down in front of me. I was getting worried and asked him what this was all about. He said he had just purchased two tickets to Florida for next weekend.
I responded with, “How nice. Who’s the lucky person you’re taking? ”
That’s when he said, “you.”
There was a pause as I processed what he had just said. Then I chuckled and said, “Great, but if you don’t want to tell me, it’s really none of my business.”
He just smiled and said, “Seriously, you.”
Was he serious? He wasn’t laughing; he just smiled at me.
As I looked at the tickets, he explained to me that he had arranged for a three-day mini-vacation and he would be thrilled if I would join him. I was shocked and speechless. He explained it was Friday to Sunday and he could arrange for me to be off work on Friday if I so pleased.
I was taken aback. I was flustered and began to ramble on something about not being able to afford it with student loans and all. He smiled and said, “Not to worry, it was all taken care of.” He apologised for being so forward and said he would completely understand if I refused his offer. For obvious work reasons, he also asked that we keep this between the two of us. He told me he had 24 hours to cancel, so I told him I would think about it and let him know the following day.
This came right out of left field and I was at a loss for words. I just nodded my head. I walked out of his office in shock. My mind was racing. What just happened? As I sat down at my desk, it hit me. I suppose he expects sex? Oh god, he is twice my age. I can’t just go with him on a vacation. What if people in the office find out? I don’t want to be known as the office slut. Why would he even ask me? I did nothing to encourage this. Why do I always get myself into these types of situations?
At this point, I was pretty sure I wasn’t going. He was nice enough, but I didn’t think of him in that way. How would this affect my employment? I was pretty sure there would be no repercussions, but he did hire me, so he could easily fire me also. I was confused and worried. I needed this job.
I had to discuss this with my good friend Jenny. Jenny had more experience than I did. She had street smarts and I always valued her opinion. She always knew what to do. I made arrangements to meet her that evening.
Jenny listened as I explained what happened. Jenny’s first question was if I thought my job was in jeopardy. I was pretty sure it wasn’t. Mr. Wilson wasn’t like that. I trusted him. She was relieved to hear my answer.
“So you do like him,” she asked.
I said, “Yes, I do, but not like that. He’s twice my age. ”
She asked if he was attractive.
“Yeah, I suppose he is,”
“Does he treat you well?”
“Of course he does; he’s a very nice man who treats me well,” I replied.
“So what’s the problem? A free trip to Florida in the winter with a nice guy you like and find attractive.” Jenny made it sound so simple.
She told me she preferred older men as they were more mature and respectful. I agreed. I was still seeing Alex’s (ex-boyfriend) father off and on, and he was wonderful to me.
I wasn’t in a serious relationship, so I suppose I could go. After an evening of discussing the pros and cons, it was settled… YES, I’m going to Florida. I was excited as this was my first winter vacation.
The next morning, Mr. Wilson came by my desk to say good morning. He paused and looked at me for a split second. I discreetly nodded my head and smiled. He gave me a wink and walked away. I felt a rush of excitement. How hot was this? A secret work romance. I hadn’t even worked there for three months, and I was going away with Mr. Wilson.
Once I had decided to go on the Florida vacation, I was thrilled. I had never been on a plane; never been to Florida; never stayed in a hotel; never spent the weekend with an older guy… it was all new and exciting. What should I pack? I need new clothes. Should I buy some lingerie? So many decisions.
Jenny and I went shopping. Jenny pushed me into buying a sexy yellow dress. It was much more revealing than I would normally wear, but Jenny insisted this is what he was expecting.
“You can’t show up in an old t-shirt and jeans, April.” She laughed.
It was out of my comfort zone, but I took Jenny’s advice and purchased the dress.
The night before our trip, I didn’t sleep a wink. My mind was racing. I was both excited and nervous. Did I make the right decision? I really didn’t know him that well as our only contact was in a work environment. He seemed very nice, but you never know.
Mr. Wilson picked me up on Friday, and we drove to the airport. Once on the plane, I was a bit hesitant. I had never been on a plane before. He held my hand tenderly and assured me all would be well. During the flight, he put his hand on my leg. I was wearing jeans, but his hand felt good as he squeezed my lower thigh and rubbed it. This was the first time he had touched me. I felt a tingle as I rubbed his arm in return. We joked about my calling him Mr. Wilson. On this trip, he insisted I call him Ben. I agreed to try it, but with no guarantees as it just felt weird.