Sex Vacation with the Boss

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 this nice older gentleman and over time he 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 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 mid 40'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 favorite manager.



One day while chatting and I complained about the cold weather and how I hated winter. He responded that he felt the same way and suggested that we should 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 intimated and worried I did something wrong. I 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 just purchased two tickets to Florida for next weekend. I said, "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 just said. Then I chuckled and said "Great, but its OK if you don't want to tell me". 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 he had arranged for a three-day mini-vacation and he would be thrilled if I would join him. I was in shock; 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 apologized for being so forward and said he would completely understand if I refused his offer. He also asked that we keep this between the two of us either way for obvious work reasons. He told me he had 24 hours to cancel so go 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? OMG, 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 the office slut. Why would he even ask me? I did nothing to encourage this. 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 repercussion 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 me. 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 did but he was twice my age. She asked if he was attractive...well yes, he was. Did he treat me well...yes he treated me great. She said "so what's the problem? A free trip to Florida in winter with a nice guy you like and find attractive." 



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.



The next morning Mr. Wilson came by my desk to say good morning. He paused and looked at me for a split second. I discretely 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 six months and I was going away with Mr. Wilson. 



Once I had decided to go on the Florida vacation, I was excited. 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. 



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 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 me calling him Mr. Wilson. On this trip, he insisted I call him Ben. I agreed.



We soon arrived at the hotel. It was a beautiful hotel right on the beach. This was my first hotel stay, sure I stayed at cheap motels once or twice but this was much nicer. The room had a large king bed, it was huge. It also overlooked a gorgeous pool and the ocean. I was impressed.



I was a bit nervous in the room, I had never thought of him in a sexual way and I was hoping it wouldn't be awkward. He picked up on this and suggested we go down to the Tiki bar by the pool for drinks and a bite to eat. I didn't even know what a Tiki bar was, I was in a different world. 

I unpacked and went into the bathroom to freshen up and change.

I decided to wear the sexy yellow sundress that Jenny encouraged me to buy. I also put on a pair of high heels. The dress was very revealing and I wasn't sure if it was too much. It was low cut both at the front and back and had a slit up the front that went almost right up to my panties. I have to admit it did a good job showcasing my young breasts. 



When I came out of the bathroom, he was floored, he loved my dress. I still wasn't sure if it was too revealing or slutty. I offered to change but he insisted I keep it on. He said it was perfect. Thank you, Jenny. I just wanted to make sure he was happy with my choice. I was very aware that this vacation probably cost him a small fortune and I wanted to make sure he knew how grateful I was. 



At the bar, I noticed a group of younger guys checking me out. I am sure they thought I was with my father or worse yet a hooker. I could tell Ben noticed them looking at me also. I felt bad as I could tell he was feeling a bit uncomfortable. I just ignored them and gave Ben my full attention.



After a few fancy cocktails, I loosened up and had the courage to reach across the table and hold his hand. Eventually, he placed his hand on my bare thigh as I sat there with my legs crossed. His hand was big, soft, and warm. I could feel myself quivering as he ran his hand slowly up and down my thigh. I was definitely warming up to him. He was getting me aroused so I suggested it was time to go back to the room.



When we got back to the room, he was very calm. Most guys I had been with would have jumped me in the elevator or at least as soon as the room door closed. But he was calm and cool. He held me and kissed me softly. Our first kiss. He was a great kisser. It felt so nice to be held in his strong arms. He was taking his time and not a mad rush to have sex like the younger guys I had been dating.

As we stood there kissing he slowly slipped my dress off one shoulder. He began kissing my bare shoulder and neck. It felt wonderful. I was melting in his arms. I could feel myself submitting to him. He then proceeded to slip the dress off my other shoulder. I stepped back out of his embrace and let my dress fall to the floor. 

I was standing in front of him in my panties and heels as he took in the sight. I was baring myself to him as if to say I'm all yours, take me. I could feel the cool air from the air conditioner blowing across my body. My nipples were erect from both the cool air and my arousal. It felt so erotic to be standing there pretty much naked as he just watched me. He just looked at me for what seemed like an eternity but in reality, it was probably only a minute or two. I could feel myself crossing my legs to hide my wet panties and maybe to stimulate my aching womanhood. 



As he stood there watching me, he began to unbutton his shirt. I stopped him and slowly took over the task. I could see the bulge in his pants but I resisted the strong urge to grab him. If he wanted to slowly tease me I could do the same to him.

I slowly removed his shirt and ran my fingers through his hairy chest. I leaned in and moved around him as I playfully kissed his nipples and then his arms. I could feel my nipples brushing up against him. I moved behind him and pressed my breasts into his back as I reached around to unbuckle his belt. He stopped me. 



He took my hand and moved me in front of the window. It was late evening and we had neglected to close the drapes when we entered the room. Our room overlooked the pool and tiki bar area and I could see lots of people at the bar. He held me from behind as he kissed my neck and cupped my breasts as he moved me right up to the window. Our room was partly lit and we were on the third floor so I'm sure everyone at the bar had a good view. He was putting me up for display. Mr. Wilson who knew you were so erotic. 



I just let my head fall back and submitted to him. He slid his hand into my soaking wet panties and slowly began to rub my clit while kissing my neck. My panties fell to the floor and I stepped out of them.

He pushed me right up against the glass. I'm not an exhibition by any stretch as I have a tendency of being shy, but it felt so erotic being put on display like this. He still had his pants on, and I was naked to the world. My body and face were pressed up to the cool glass as he stimulated my clit.

I began to shutter and quiver as I had an orgasm right there standing in front of the window. At this point, I didn't care who was watching. He continued to hold me from behind as I recovered. I glanced out the window and I could see those young guys that were sitting at the next table from us earlier that evening all looking up at me. Was Mr. Wilson making a point to them? Did he do this on purpose? It didn't matter, it was hot and erotic and I wanted more. He could do whatever he wanted with me, I was all his this weekend.



He then guided me onto the bed and continued to slowly seduce me. He took it very slowly. He made me feel comfortable and relaxed. He ran his hands and lips all over my body as I just laid there for him. He slowly and gently kissed and suckled my nipples. My nipples were incredibly swollen and erect. He was enjoying my breasts and even commented on how firm and beautiful they were. 



His attention then slowly moved down my body to my legs. He began kissing and licking my toes, slowly removing my heels. He slowly began moving up my legs. By the time he got between my thighs, I was begging for more. He had me craving for more. I found myself asking him to fuck me..."Please fuck me Mr. Wilson...please."

Instead, he slowly began giving me oral. OMG he had me so worked up. 

He took his time, and he knew exactly what he was doing. I had another two orgasms before I even had the opportunity to return the favor. I had to have him inside of me. No man had ever gotten me into that kind of state. I never had to beg for a man to fuck me. Mr. Wilson had turned the tables on me. I just couldn't wait any longer. 



I yanked off his pants and quickly put him in my mouth to taste him and lube him up. Then I climbed on top of him and slowly lowered myself onto him. I was so wet he just slid in. I don't think I ever craved a man's cock as much as then. I selfishly rode him hard and fast until he succumbed to my craving. He shot his load deep inside of me as I came again.

I fell down on the bed next to him exhausted but satisfied. Mr. Wilson, what have you done to me? He held me in his arms and we fell asleep.

The next morning I woke first. As he laid there sleeping I proceeded to awaken him with a morning blow job. The night before he had me so worked up I never gave him the proper blow job he deserved. He was very appreciative and suggested I wake him every morning in the same manner. I was more than happy to.


That weekend I had a new appreciation for oral sex. Mr. Wilson brought me to climax over and over. I don't even recall how many orgasms I had that weekend. Mr. Wilson had the best oral skills of any man I had ever known. 



I did everything for Mr. Wilson that weekend. He made me feel special and I showed him my appreciation in return. Mr. Wilson introduced me to another world. We ate at nice restaurants, had a great time at the beach. This was all new to me and I loved it. So this was how the other half lived. I was treated like a lady and I enjoyed it.

No more dumb, poor, immature boys for me. I loved older men and how they treated me.



I returned to work on Monday morning and said good morning to Mr. Wilson as he walked by like nothing ever happened. 



About four months later Mr. Wilson called me into his office and told me to close the door...This time it was Los Angeles for five days. I didn't have to ask Jenny this time.

True story.

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