Sex Vacation with the Boss

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Tem 23, 2022 // By:analsex // No Comment

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Brunette

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 güvenilir bahis 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.

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 a few times, 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 of showcasing my braless young breasts. The thin material barely covered my nipples as the neckline plunged down to my waist. I would have to be very careful how I moved in this dress, otherwise my breasts would just fall out.

When I came out of the bathroom, Mr. Wilson was floored. He loved my dress. I’m pretty sure he wasn’t expecting me to be dressed like this.

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 güvenilir bahis siteleri 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 Mr. Wilson 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 of the guys I had been with would have jumped me in the elevator, or at least as soon as the hotel 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 was not in 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 squirming my legs together to stimulate my aching womanhood as I stood there before him, baring my young, firm body. I was heating up fast and I could feel a dampness in my tiny thin panties.

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, revealing a sexy, lush, hairy chest. I playfully ran my fingers through his hairy chest and let out an approving low-pitched moan.

I leaned in and moved around him as I playfully kissed his nipples and then his strong arms. I could feel my erect nipples brushing up against him as they were now fully swollen and super sensitive. 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 a finger immediately began to rub my clit while he kissed my neck. My panties fell to the floor, revealing my perfectly bald and wanton pussy.

Jenny had reminded me that older men love bald and smooth young pussies. Of course, Jenny would know. I did shave myself, but Jenny gave me the number of a lady that she used for waxing. She insisted I ask for a Brazilian wax. I followed her instructions and was thrilled with the outcome.

Mr. Wilson pushed me right up against the glass. I’m not an exhibition by any stretch, as I have a tendency to be 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 against the cool glass as he stimulated my clit. The cool glass felt wonderful up against my erect and swollen nipples.

I began to shutter and quiver as he dipped a finger inside of iddaa siteleri me and then returned his lubricated fingers to my clitoris. His fingers left wonder as they freely slid over my waxed virgina.

I could feel an orgasm building up inside of me as he slowly circled and teased my erect clit. I gently flicked and tugged on it. He rubbed and encircled it with his finger.

As he kissed the back of my neck, I lost all control and just had to let the orgasm wash over me. I let out a deep low moan as he continued to hold me up against the cool glass. My legs went weak, but he had me pinned to the window.

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 lay 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 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. He sucked on my clit like a master. Not too hard, not too soft, but just right. Orally, no man before him took as much time and effort to satisfy me as did Mr. Wilson. As he stimulated my aroused clit, he was fingering me. Not finger fucking me like all the boys did, but curling his finger up and stimulating my G spot.

I began to have multiple orgasms… one after another. Mr. Wilson was relentless. He had a hold of my ass and his face was buried between my legs.

“Oooh…my god…stop…..no don’t stop…ohhh…” He had me climbing the walls in ecstasy.

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 pushed his head away as my body quivered and spasmed from a remarkable orgasm. I was feeling weak and drained, but I knew if I continued to lie there, Mr. Wilson would have orally attacked my pussy again. It was time for me to make my move.

I managed to jump up and yank his pants and boxers off. I 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 that 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 lay there sleeping, I proceeded to awaken him with a morning blow job. The night before, he had me so worked up that 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 a 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 and 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.

A

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