Becoming The Bosses Favorite
written by:
oppy-n-rose

Invited To A Seminar

I was sitting at my desk going over some paperwork early on a Monday morning when I noticed one of the other assistants arrive at her desk. She seemed to be in a pretty good mood and I had a pretty good feeling as to why. She had just gotten back from a corporate seminar that she had attended with the boss of the company. I was pretty sure I knew what had happened during the seminar to make her happy. See, our boss had a habit of taking an assistant to these seminars whenever he went, and while they were there, he would offer them bonuses or raises in return for some fun. I had heard first hand from a few of them about their trips. I had always prided myself on being one of the select few that haven't gone on one of these trips with him. I assumed it was probably because I was a married woman and had put on a bit of weight after having my baby. I really didn't care about what they were doing but I did have a bit of a problem with the fact that they were getting all these bonuses for spreading their legs while I had to earn mine. I won't lie about the fact that on several previous occasions, I had wondered if something like that would be worth it or not. After all, I would certainly love a bonus or even a raise, but at the same time I really wasn't interested in getting sexual with my boss. I went about my work and tried not to think about it.

About a month or so later, word began spreading around the office that there would be a big seminar coming up. This one was different from the others because it would be attended by some big-time names in our industry. What made it significant was the fact it was being held at a very expensive resort in Bermuda. It definitely caught my attention because I'd be crazy to say that I wasn't interested in going to Bermuda. I automatically figured that our boss would probably grab one of the young assistants in the office to go with him and tried not to pay much attention to all the chatter that was going around.

Friday afternoon arrived and I headed down to my bosses office to grab my paycheck before leaving for the weekend. When I walked in he was sitting at his desk, working on his computer. He looked up and greeted me when I walked in. We chatted for a few seconds as he handed me my paycheck and asked me if I had a minute. I said sure and sat down in front of his desk on one of the chairs. I wasn't really sure what to expect as he finished up on the computer. He began talking and told me about the upcoming seminar and I was a bit surprised by it. He continued talking about it and told me all the details before asking me if I would be interested in attending. I was caught off guard and really didn't know how to respond. As I sat there, he told me all about it and explained what we would be doing at the seminar. I finally spoke up and explained to him that I would have to make sure that I could get someone to take care of my child in order to go. He fully understood and said that I could have a few days to think about it and get back to him. I thanked him for the offer and after grabbing my paycheck, was on my way home.

I arrived home a short time later and after picking up my son, headed into my house to prepare dinner. The entire time, I kept thinking about the offer that had been made to me. I realized that during this trip, my boss would probably try to have some fun with me. I obviously wasn't interested in any of that but at the same time it was a free trip to Bermuda and who would want to say no to that. I had a lot running through my mind and continuously myself what I would do if my boss did try to come on to me. I knew what the outcome was if I let him have his way and could certainly use all of the money that I could get because things were a little tough at the moment. We had a baby and house payments to make and with my husband's job being a little slow, things were very tight. At the same time, I was a married mother and doing anything at all would obviously be wrong. Like I said I wasn't interested in any sexual activity with my boss or anyone else for that matter, but I also didn't want to jeopardize my job. I had a lot to think about in a very short period of time.

Later that evening, I spoke to my husband about the trip and he encouraged me to go on it. Of course I didn't mention the whole sexual aspect of it. He told me that I deserved a vacation and that he would tend to our son. I spent the next couple of days thinking about everything and told myself that if I did go on this trip and my boss were to try anything, I would make sure to not just lie down and spread my legs. After weighing all the pros and cons, I decided that I would go on the trip and take everything one step at a time.

The following Monday I arrived at work, and when I ran into my boss I let him know what my decision was. He was happy and told me that I wouldn't regret it and I thought to myself that I hoped not. He gave me some paperwork and information about the trip and the seminar and told me that we would meet at the airport on Saturday morning. The trip was going to be from Saturday until the following Saturday and we would be attending the seminar each day. I look forwarded to a getaway to Bermuda and hopefully it wouldn't be too bad.

Saturday morning arrived and after getting dropped off at the airport by my husband, I met up with my boss and we soon boarded our flight. We had a smooth flight and landed later that afternoon in Bermuda. At the airport, a limo awaited us and took us to the resort. After checking in, we made our way up to the suite where we would be staying. The one drawback is that we had to share the suite but at least we had separate beds. We made our way into the room and got settled. We spent the rest of the day relaxing and lounging around before eventually heading out to dinner. I didn't know what to expect and like I said was going to take everything one step at a time.

My boss and I had dinner at a very nice place and I was pleasantly surprised to actually be enjoying myself. We had a very nice conversation about work and family as we enjoyed our dinner. He never said or tried anything sexual and I was happy about that. We eventually finished up our dinner and headed back to our suite to call it a night. We were both a bit tired from the flight and decided to make it an early evening.

The next morning we got up and prepared ourselves to go to breakfast. We go out and enjoy breakfast at a local eatery and once again it was a pleasant experience. We returned to our resort after eating and pretty much had the rest of the day to ourselves since it was Sunday and the seminar didn't start until Monday. We made our way up to our room and while we were there, he told me that he was going to take a walk on the beach and would be back later on. He asked me what my plans were and after telling him that I really didn't have any he shocked me by taking out the company credit card and telling me to go out and enjoy myself. I couldn't believe what I was hearing. He told me to go out and do some shopping and enjoy myself and to not worry about anything. I wasn't sure if this was part of his ploy or not but wasn't about to turn down free shopping. I took the credit card and soon found myself walking around the streets, going from shop to shop.

Later that day, I returned to the resort and found my boss lounging by the pool. I let him know that I was back and he asked me if I was enjoying myself and I told him that I was and thanked him for everything. He smiled and told me to go get ready for dinner and I did. I got dressed for dinner and once he was ready, we headed out. We once again enjoyed a very nice meal along with a few drinks before heading back to our resort and calling it a night. I was surprised at how good things were going and hoped that the rest of our trip would be this easy.

The following morning after having breakfast, we headed to the seminar. We spent almost half the day walking around and meeting with other business owners. It wasn't the most exciting stuff but I knew it had to be done. We eventually wrapped up our first day at the seminar and headed back to our room. It was midafternoon and we decided to go over and get something to eat at one of the local eateries. I got dressed and decided to wear a summer dress that showed some cleavage since it was pretty warm out. It wasn't too sexy so I didn't think anything of it. I finished getting ready and once my boss was ready we headed out. The entire time I could feel his eyes on me as he admired my outfit. I guess you can say I enjoyed a bit of attention since I hadn't gotten a lot lately. We headed out of the resort and I was surprised when I saw a limo out in front of the resort waiting to pick us up. We got in and my boss instructed the driver on where to take us.

We arrived at a nice restaurant a little while later and made our way inside. We were seated at a nice booth and he immediately ordered a bottle of wine along with a couple of appetizers. The wine soon arrived and after filling our glasses he toasted to our trip. We sat and chatted while we waited for our food. As we chatted, I felt the wine starting to get to my head and if there was one thing that wine or any alcohol for that matter did to me, it made me open up and talk a lot. Our food arrived and we enjoyed it while continuing to have a nice conversation. At some point he asked me how things were at home and feeling talkative, I told him a lot. As I told him about a few of the problems, I made the mistake of telling him how tight money was. He sat and listened to everything I said. Once I was done, I quickly apologized for venting and he told me not to worry about it and said that he might even be willing to help. I just sat and looked at him and kind of knew where this was going.

He had a smirk on his face and asked me if I would be interested in earning a bonus or two. Surprisingly, I nodded and asked him what was involved. I was surprised at myself for even going along with this but I guess it could partly be blamed on the wine. He smiled and told me that he knew I was a married woman and obviously wasn't looking for any kind of commitment or anything else but would be willing to give me a few bonuses if I was interested in earning them. Of course, I knew exactly what he meant and just sat while nodding my head. He told me that I wasn't forced to do anything that I didn't want to and that it was completely up to me. I told him that I understood and that I needed time to process everything. He smiled and nodded. We continued eating our dinner and enjoyed the rest of the meal as everything ran through my mind. He had pretty much offered me his proposal and now it was up to me to decide what I was going to do. Of course being pretty mellowed from the wine probably wasn't going to help in making the right decision. We eventually finished up our food and headed out to the limo for our ride back to the resort.

Once in the limo, I sat across from him and he asked if I was enjoying my stay in Bermuda. I told him that it was lovely and thank him for bringing me along. He then grabbed the phone and called up front to the driver, telling him to take us for a ride so that I could see what Bermuda had to offer. The driver nodded his head and began driving. I sat back and enjoyed while my boss went into the wet bar in the limo and poured us each a glass of whiskey. I wasn't a big drinker but decided to go with it. After a quick toast, we enjoyed the drinks as well as the scenery at the limo drove us around the beaches.

After driving for a bit, my boss looked over at me and asked me how I was feeling. I told him that I felt great and was having fun on my trip. Of course I was feeling pretty drunk by now and was pretty much just babbling. He could tell that I was drunk and began to compliment me and tell me how sexy I looked. It did make me feel good and I thanked him for his compliments. We went back and forth for a little bit before he asked me if I had given his proposal and he thought. Now under normal circumstances I would've brushed him off and told him to get lost but feeling the way that I was, I surprised myself by asking him what he wanted. Without saying anything, he reached down and began to undo his pants. He slid them down along with his boxers and his hard cock sprang free. It was about seven or 8 inches long and fairly thick. I couldn't believe what was happening, and even worse I couldn't believe what I did next.

I dropped to the floor of the limo on my knees and made my way over to him. Without any hesitation, I wrapped my hand around his cock and began to stroke it. He leaned back and enjoyed. I slowly stroked it for a few seconds before putting my mouth against the tip. He let out a soft moan as I began to lick it with my tongue before wrapping my lips around it tightly. Slowly, I took in inch-by-inch of his cock into my mouth and tightly wrapped my lips around it. I bobbed up and down on it for several minutes as he moaned in pleasure. After a few minutes of this, he placed his left hand on the back of my head and guided me while reaching down into my dress and squeezing my tits with his right hand. We went at it like this for a few minutes before I felt him tense up and began shooting his hot load down my throat. I continued to bubble up and down on it and swallowed as much of his hot cum as I could. After about another minute or so, I finished blowing him and sat back on my seat. He had a huge smile on his face and told me that I had just earned my first bonus. I felt a bit disgusted with myself but know that in the end the money would help out immensely. The limo drove us around for a little while longer before dropping us off back at the resort where we headed up to our suite.

Once in our suite, he poured us another drink and I had a feeling that my day wasn't over yet. We chatted for a few minutes before he suggested taking a walk out to the beach. I was all for it and quickly made my way into the bathroom to change into my bikini. Once I was ready, we headed out to the beach. It was late afternoon and the beach was pretty crowded. We went out and enjoyed the water for a bit before deciding to head to our resorts pool. We made our way poolside and noticed that it wasn't that packed. The resort had its own restaurant and bar and we could order drinks from the bar to enjoy poolside. My boss took care of everything and we soon had several drinks delivered to us. We laid out by the pool and enjoyed our drinks. The entire time I could feel his eyes on me yet again as he admired the view. We spent several hours lounging by the pool before taking a dip.

We swam around for a bit and after a while he suggested we warm up in the hot tub that was attached to the pool. There was a couple of people in it so I didn't mind. We made our way into the hot tub and relaxed while enjoying the hot water. The entire time we were there, we continue to have drinks delivered, as did some of the other people who were in the tub. My boss struck up conversations with a few of them and we ended up spending a couple of hours relaxing and chatting.

Eventually it started getting dark and some of the other guests began to leave the pool area. Little by little the place emptied out and we were the only ones in the hot tub. My boss looked at me and jokingly said that it looked like we had the tub to ourselves. I didn't say anything and just smiled while enjoying the hot water. I soon felt his hand on my left knee as he was sitting next to me but didn't say anything. He rubbed my knee under the water and slowly worked his way up. As he did, I instinctively parted my legs and soon felt him rubbing my pussy through my bikini bottoms. I couldn't believe that I was making it this easy for him. He rubbed it for a bit before working his hand underneath my bottoms. Once there, he slowly insert a finger into my pussy and began to work it. At the same time, he untied his swim trunks and pulled his cock out. With his left hand he grabbed my left hand and placed it on his cock. I began to slowly stroke it while he continued fingering me. We did this for a few minutes before he looked around and realized that there was nobody in sight. Thankfully it was pretty dark by now and the area we were in was not lit.

After looking around he told me to get up and I complied. He pulled me over to him and had me sit on his lap, facing away from him. With one hand, he slid my bikini bottoms out of the way and with his other hand he guided his cock to my opening. I slowly lowered myself onto it and felt him penetrate me. It actually felt pretty good and I was surprised to be enjoying it. It was the first time in my life that I had another man's cock in my pussy, besides my husband. I lowered myself onto his cock until he was buried inside of me. Slowly, I began to bounce up and down on his cock while he grabbed me by the hips and guided me. We did this for a few minutes and the excitement of the situation, as well as being drunk, led me to a very strong orgasm. I hadn't experienced something like that in a very long time as I came very hard. He continued to guide me on his cock before also tensing up. Within seconds, I felt his hot cum flooding my pussy. He shot wave after wave of his hot seed deep inside of me as I continued to bounce up and down on his cock. We went at it for another minute or so as I milked his cock of every drop.

Once he was done, I climbed off of him and sat back down in the hot tub. We both sat there for a couple of minutes as I replayed everything that had just happened in my mind. I was angry with myself for allowing things to go this far and at how easy I had let it all happen. I knew that there was no turning back at this point since he had already fucked me. After sitting in the water for a few minutes, he suggested we head back up to the suite. We both got up out of the hot tub and after grabbing our towels, we made our way up to our floor.

I wasn't sure what to expect as we made our way to the suite but knew that there was no way that he was done with me. We walked into the room and as soon as I dropped my towel onto a chair, I felt him come up behind me and grab me by the hips. I didn't say or do anything and just let him take control. He guided me over to where the bed was and began to untie my bikini top. Once he untied it, he tossed it aside and began to squeeze my tits as he stood behind me. He squeezed them for a bit before reaching for my bikini bottoms and sliding them off, leaving me completely naked in front of him. He then had me climb onto the bed and get on all fours as he took off his swim trunks, leaving him nude as well.

He then climbed up onto the bed and positioned himself behind me, between my legs. He grabbed his hard cock and lined it up with me pussy. He easily penetrated me and slid his entire cock deep into me. This time around he didn't take his time as he grabbed me by the hips and began to thrust pretty hard. I gripped the sides of the bed as he fucked me from behind. He was being pretty aggressive and something about that actually turned me off a bit and I could feel myself building towards an orgasm yet again. I reached underneath and gently rubbed my clit as he pounded into me. Within a minute or so I began to cum once again and came pretty hard. I let out a loud moan as I did and I just caused him to fuck me even harder. He pounded me for several minutes while reaching underneath and squeezing my flailing tits. Without warning, he tensed up and blew another load deep inside of me, flooding my pussy with his hot seed yet again. He continued to pump into me until he had shot off every last drop. Once he was done he pulled out of me and the two of us collapsed onto the bed and eventually passed out.

It was just the beginning of what became a long week of me sucking and fucking him each day, several times a day. I had done the opposite of what I had said I would do and pretty much made it easy for him to get what he wanted. In turn, I managed to get a pretty hefty raise and several bonuses. He told me that I was his favorite assistant and that I would be coming up for promotion real soon. I thought I would hate myself after all of this, but as I was writing this, I was preparing for another business trip with him...