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was the one who probably needed to watch her mouth. I assured him that I am a grown woman and I would handle any situation that came up, tactfully, without involving HR, or anyone else. The owner smiled when I said that. Seeing that I had the owner’s approval, I added that in the real world, things happen and they should just be ignored or forgiven. The owner smiled even bigger.
When he offered me the position, the first thing he told me was that if I accepted the job, I would have to stop calling him “Mr. Hicks” and call him Robert. He explained that he wanted our customers to believe that I was an equal partner in any negotiations. His theory was that there were usually two or more representatives from the company that we were courting, selling our services to; With me being part of the negotiations, it helped even the score. He wanted me to be respected as an equal and not thought of as his assistant or his secretary. He told me that he thought I was the person to do the job. Those comments were some of the highest praises I had ever received. I felt like I was walking on air.
I asked if I could return to my old job if this position did not work out. He shook his head, sadly, and told me that this was a one-way opportunity. He, Robert, explained that after working for him, I would be ridiculed and subjected to too many questions about what went on during the bidding process. He explained that I would be privileged to many dollar figures and personal information that might cause the other employees to feel that they should receive more pay or that he was in some way cheating them in the process. Robert defended his business practices by saying that he is currently paying significantly more than his competitors. Robert told me and I had to agree that most of the people who worked on the factory floor did not understand business well enough to be privileged to that kind of information. He explained that I would have to sign a non-compete agreement that contained clauses limiting what I could tell anyone about my job, including my husband. When I baulked at the thought of not being able to tell my husband what I was doing, he assured that the decision to limit what the husband was told, stemmed from the fact that they often knew and were friends with my former co-workers. If he tells a friend of his and that friend tells another friend, eventually, there is no confidential information left to give our company an advantage in the bidding process. However, he made it clear that I could tell my husband what we were doing, such as, we are trying to get “The Smith Corporations” business. He just did not want me to tell him or anyone else what prices and services we were offering to win the contract. Robert assured me that the only reason that I would be let go would be because I was not suitable for the job.
This scared me a little because I knew that if I was fired, I could not get a job that paid nearly as well as the one I had now. To ease my fears, Robert told me that as the final step in the interview process, we would be attending a mock business meeting with some of his friends. He joked that his friends were horrible customers, but they would give me a good idea of some of the situations that I would incur as part of my new job. If I was unable or unwilling to continue after the mock meeting, he would allow, this one time, for me to reclaim my previous position on the factory floor. My fears were real but the high praise he had given me caused me to accept the job. I promised to do my best.
After shaking my hand and reassuring me that I would do fine, he advised me that my final test of the application process would be the following night. The dinner was not with potential clients; it would just be the two of us and the two long-term friends that he had warned me about. They met for a monthly meal, at one of the nicer steak houses in our town. He wanted me to be dressed nicely, as if we were meeting actual clients. I would be expected to be part of the conversations, when it was appropriate, and in essence, be his arm candy for the evening.
The whole thing sounded a bit weird, but I knew that the biggest deals were made on the golf course or in a bar, after the main meetings, so I understood why he wanted to be sure that I could handle myself in a business conversation.
When I got home that night, I explained the opportunity to my husband, Jim, and told him that I had already accepted the job. He was less than impressed and suggested that the owner was more interested in how I would act as his date, rather than needing me to be part of the negotiations. Jim also suggested that the part of the negotiations that he probably had in mind for me was for me to subtly offer myself, to the client, as an incentive for them to sign the agreement. My husband’s attitude pissed me off. He was unemployed and I was stepping up to support our household, and all he could do is imply that I would be a low-priced escort.
Probably due to the stress of my husband being laid off and the tightened finances, my husband and I had been going through a rough patch. So far, nothing serious but we argued more than usual.
Even though I didn’t fully agree with my husband’s opinion, I am not stupid. I knew, deep down, that there would probably be customers, men in particular, who would come on to me during and after negotiations. I also knew that I was nearly fifty years old and most men would be more attracted to a twenty something hottie. I knew that if alcohol was involved and I was one of the few women in the room, they would make a play for me. I would have to just let them down carefully and explain that I was married. Further, I have looked at myself in the mirror and I did not believe there would be very many men hitting on me.
The next day I had my hair and nails done during my lunch hour and I prepared my best LBD to wear that evening. My dress was only slightly too sexy for a work function. It followed my curves a little too close. It was just an inch or two too short and the dress showed just a tiny bit too much cleavage. If my husband had been working, and we had the disposable income, I may have purchased a new dress. I was sure that my choice of attire would be well accepted and if Robert did not like it, I would buy another dress, after I officially received the job.
As I had been instructed, I returned to the office at 6:30 that evening, so that Robert and I could travel to the steak house by 7:00. Robert complimented me on my choice of dresses and told me that I was not only beautiful, but I would be a clear distraction to any client that we chose to entertain. Again, his praises made me feel fantastic.
Robert suggested that I drive since he was planning to have several drinks over the course of the evening. After we walked to my little Camry, He suggested that it might be better if I drove his Mercedes.
I had never driven a Mercedes, but the car seemed to drive itself. I was already proud of myself for taking this job.
When we walked into the Steak House it was obvious that Robert was well known. His two friends were already there, waiting for us. Both of his friends were well dressed but they appeared to be a little older than Robert. I was immediately nervous and suspicious because it was obvious that they were mentally undressing me with their eyes. Since I knew that this was a test of my abilities, I was prepared for them to push the envelope of what is acceptable flirting and what is unacceptable in a business setting.
After introductions were made, drinks were ordered and I was totally surprised that my boss knew that my favorite drink was a Margaretta, on the rocks, with salt. The conversation was light and within moments, the waitress brought us our drinks. After just a few moments of relaxation, one of the men began to question me about my role within the company. When they learned that I had been in the production department for over twenty years, they were quick to ask relevant questions about how we processed our orders.
I was quite proud of myself, because I was able to answer their questions correctly and in a manner that was interesting to them. The other man began to question me with more personal questions. His first question was whether I was married and what did my husband think about me working closely with Robert. He was tenacious and became very specific about how I would handle overt attempts, by customers, to obtain sexual favors from me.
This was getting weird, but I felt that it was all a test to see if I could handle being put into a tense situation. Because I did not think their comments were real, I answered with the same answers I had given Robert. I told the two men that I was a big girl, and I could handle whatever they had to offer. When the two men suggested that I move from sitting between Robert and one of the men, to sitting between them since they were the clients; I took their dare.
I looked at Robert; he was smiling and gave me a slight nod. I boldly stood and moved to sit between them. They made room for me but did not scoot so far apart that I was comfortable. When we settled in, we were shoulder to shoulder. I was not too worried because Robert was across from me and I knew that this was just a test.
While I was continually peppered with questions about our delivery times and the precautions, we used to ensure a quality product, I noticed that one of the men had put his hand on my thigh. Even though he was just inches from my pussy, he was not moving his hand, and I was not sure if he was being fresh or if he had just laid his hand on my leg casually in the cramped booth.
A few minutes later it became obvious that his hand was not on my leg by accident. His hand began to move but, again, I was not overly concerned because in addition to my dress, I was wearing pantyhose and panties under them. He may not have realized it, but he was feeling me up with three layers of cloth between my body and his fingers. Within seconds he had pushed my dress all the way up and his fingers were massaging my pussy over the panty hose. Well, I guess we were down to two very thin layers of protection between his fingers and my sex. I must admit that it felt wonderful. Since I have been married, my husband and I did not engage in risky sex play. We did not need to. If we were in the mood, we would head home and sometimes if I was particularly hot, I would stroke my husband and let him feel me up as we drove home. That was about as risky as we got. Trying to carry on a conversation with the other man and my boss, while the man next to me was trying to discreetly rip my pantyhose, was difficult.
I do not know if Robert knew exactly what was going on below the table where I sat, but he appeared to be extremely proud of me. Believe it or not, I was able to quote previous delivery times on similar orders, with what I hope was a reasonably straight face. The man next to me, he went by the name Trey, managed to rip my pantyhose and slip my panties aside, my answer to the question I had been asked came out something like, “We did it in UGH, ah ah UGH ah, in about two weeks.” He had very large fingers and if I was single or even in a more relaxed situation, I could have really enjoyed them. If the other two men had any doubt about what was going on under the table, they were probably aware now.
I should have been outraged, that a relative stranger was fingering me under the table but because I felt that I was being tested and because I was pretty sure that I was expected to push the envelope of what I was willing to accept, I allowed it, for a while, before I gently pushed the man’s finger from my body and quietly explained that this was not the time or the place for what he was doing. To keep things light and friendly, I teased the man, who had become quite familiar with my nether regions, telling him that if he wanted to continue doing what he was doing, I expected to be taken to dinner and to be courted. Everyone laughed and the men began to behave themselves. I was complemented frequently while we had coffee and dessert.
Robert and I prepared to leave the steak house. As we stood, the other man, named Buck, who had been a perfect gentleman all night, gave me a hug that was longer than would be acceptable for a business setting. The hand that was hidden from view cupped my breast outside of my clothes and he whispered that he was going to enjoy spending time with me. I wasn’t sure what he was implying, but I stayed in character and whispered back to him that I was anxious to get to know him better.
I had two Margaritas, two very large Margaritas, and was feeling very relaxed, but Robert had several shots of expensive bourbon and at least three Old Fashioned style drinks. He is a big man, so he was not obviously drunk, but he was quite tipsy. He may have been legally intoxicated, but it was clear that he was fully aware of what his friend had done below the table and he acknowledged that I had passed the test with a nearly perfect score. I wasn’t sure what I would have had to do to achieve a perfect score, so I asked him why I hadn’t received a perfect score. I added that I have a huge hole in my pantyhose to prove that I was a team player. Robert chuckled and told me that I did not have a perfect score because the test was not complete.
When we returned to the office, Robert explained that he was going to stay at the office until he sobered up a bit, and he instructed me to park his car in the underground garage. I felt relieved because our dinner meeting had gone well. I was a bit apprehensive because it appeared that being felt up, by relative strangers, would be part of my job description.
I decided that there would be no real harm in letting a potential customer have a quick feel of my body, if allowing that customer, to feel my boobs and maybe a bit more improved our chances of making the sale. I would take my own advice and accept that these things happened. Personally, I thought that using my body to close a business deal would cause our customers to lose respect for our company, but I was quickly learning how the real world and our company did business.
I reminded myself that, I was not ever going to be romantically involved with these men. I reasoned to myself that my doctor has seen more of me than a customer would. For that matter, the massage therapist that I use a few times a year, has touched almost every part of me. He has never strayed so far as to be inappropriate, but he is very lax when it comes to keeping me covered and his hands have accidently bumped my sex or my breasts countless times. I know he has seen everything I have and my husband has always been comfortable with me using a male massage therapist.
I was not going to complain; this job meant too much to me. As I had told the men earlier that night, I am a big girl, and no one was harmed by allowing my bosses’ friends to feel me up. I told myself that except for the cost of a new pair of pantyhose, tonight was fun and no real harm was done.
Before we exited the car, Robert asked if I was offended when Buck groped my breast. Either Robert was very observant or the night had been practically scripted after years of interviews. I smiled and told him that it was not a big deal. I then blushed and told Robert that I had hardly noticed after his other friend, Trey, had his fingers in my honey hole for several minutes. I wanted to say, “See, I am a team player” but the smile on Robert’s face told me he knew. With that, he reached over and gently began to fondle my right breast. I froze, but I did not try to stop him. I was pretty sure that this was the final part of my test, and I knew what I would have to do to pass the test.
I remained still, but I made a conscious effort to keep my breasts pushed forward and moan softly, while Robert continued to feel my boobs. He reached behind me, unzipped my dress with one hand and expertly tripped the catches of my bra. He then carefully pulled my breast from my dress and caressed my bare breast while rolling the nipple between his thumb and pointer finger. Robert explained, like this was perfectly normal, that some of our clients would want to spend quality time with me. I did not know what to say, exactly, so I just whispered, “Yes, I know.” If I hadn’t known before, I certainly knew now. I would be getting felt up occasionally. I knew that I should upset and indignant with the liberties that my boss and his friends were taking with me, but I told myself that there was no harm done and, in fact, tonight had been more exciting than any previous night in my life. My situation felt other worldly, and I was quite enjoying the evening.
I was surprised when he continued. Robert told me that it wasn’t necessary, but he felt that he should be entitled to everything his customers might enjoy. He admitted that he also wanted to know what my breasts felt like because he had noticed them since I started at the company. I believe he was sincere and I had been with the company for over twenty years, that is a long time to want something, and I felt a little pride knowing that I was finally able to give him what he wanted. I wondered if he might be encouraging our customers to enjoy me. I had to give him credit for being creative. I knew that his reasoning was very flawed, but he had admitted that even though it was not necessary for him to have my body, he wanted it.
Right or wrong, it makes a woman feel good to know that a man wants her. We do not usually give in to other men’s advances, but we love knowing that they want us.
About now, you are probably thinking that I am some kind of slut looking to cheat on my husband. After all, my boss would be the third man, in the past three hours, to play with my boobs and I suspected that Robert planned to have everything his friends had and more. At this point I was quite sure that I would be having sex with men I was not married to, but because I was not romantically attracted to these men, it did not feel like I was cheating. I felt that doing it to get and keep a customer, and not out of lust for another man, made it somewhat acceptable. Even though I knew what I was doing would not pass the husband test, I reasoned that if I dressed slutty and worked as a bar tender, I would not be cheating, and guys would most likely be taking liberties. Yeah, my reasoning may have been a little flawed too.
I already had both of my boobs hanging out the front of my dress and when Robert asked if we could sit in the back seat for a while; I did not bother to put them away. I must admit that I giggled like a schoolgirl as we scooted together in the back seat. Here I was, decades past being a schoolgirl, about to get felt up and maybe more in the back seat of a car. The Mercedes’ back seat was huge and we were quite comfortable.
Robert did not kiss me. After all, I was his employee, but he had soon removed my dress and was carefully exploring every inch of my body. Even though we were in the parking garage, it was a semipublic place, and I was completely nude. That made me excited. I was beyond caring and when he asked me to lay back, I was prepared for and was expecting that we would have sex. I was not sure what to do when he simply parted my legs and looked at me, down there. He gently touched my labia and barely penetrated my lower lips with his fingertip. I think he wanted to see if I was wet down there. I am sure he found me wet and swollen, wanting sex, because that is how I felt. After he appeared to be satisfied with how I looked, between my legs, he pulled me close and hugged me. I slowly put my hand on the crotch of his slacks and immediately felt that he was very hard.
I looked into his eyes and asked if what I was doing was okay. Robert nodded and leaned back into the seat. I knew what he wanted and carefully opened his slacks and extracted a slender but very hard cock. When I began stoking his cock, he jammed a finger up inside me. I had not noticed but his fingers were also long and slender. He matched his fingering to the speed that I was stroking him. We both came within seconds.
I expected that he would want to go all the way, but like he could read my mind, he told me that he wanted to save having sex with me, until we were in a five-star hotel, away from home, and we could make a night of it. On the one hand I was relieved that I would not have to cheat on my husband tonight, and on the other hand I was upset because I was already going to have to lie to my husband about what I had done so giving myself some relief would have been nice.
I continued to stroke Robert’s cock while he fingered me. I asked him if we would be going to a five-star hotel soon. He grunted something that was probably a yes, so I told him that I was looking forward to having his cock inside me. That nearly set off his second climax, and he used his other hand to push my head toward his cock. I was already planning to take him into my mouth, so I finished him with my mouth and made a show of swallowing his offering.
Before I left, he told me that I had not only passed but I had received a perfect score. I blushed, knowing what I had done to earn that perfect score.
As I drove home, I sucked on a breath mint to ensure there was no evidence of what I had sucked on earlier. I did not want to have cock breath. Even though I had not received any relief, I had a smile on my face. My husband was waiting for me. I went to him and gave him a hug, like I always do when I return from a late meeting. He was amorous so I told him to lock up and to join me in the shower. I quickly ditched the pantyhose and was careful to leave my underwear on top of the laundry hamper. It was obvious that the gusset of my panties was damp, but they clearly did not have any cum in them. My husband appeared to notice but he did not comment. We showered and made sure we were both very clean before going to bed where I finally received the relief I needed.
It was the following evening before I gave my husband the sanitized version of what my date / meeting had been like with my boss. My husband seemed skeptical and he did not like what I had done, as part of my job, but he was also not angry. The sanitized version amounted to that I had been allowed to drive the Mercedes and the guys at the steak house had made a few mild passes at me but the most inappropriate thing that had happened was when the one guy felt my breast over my clothes, when we said goodbye. I softened the blow by telling my husband that the man was quite drunk. I made it sound like it may have been accidental but told my husband that I thought it may have been “Accidental on purpose.”
I portrayed my boss as being proper and left out the fact that I had willingly given him relief with my mouth. I did not mention that he expected me to spend the entire night with him the next time we were out of town and in a five-star hotel. I did not mention that he expected me to spread my legs for him and make my other holes available too. Yeah, my boss mentioned to me that he wanted my ass too. I knew that there was no excuse for what I was doing but I consoled myself by telling myself that I was doing it for my family, but I could not convince myself that I was not enjoying what I was doing. I told myself that our family was in a tough spot and I was stepping up, or maybe I was laying down, to ensure that my family could continue to enjoy the type of life they had become accustomed to. I told myself that nothing said I had to hate a bad situation, if I could let myself enjoy what I had to do, well that was nobody’s business but mine.
This was sort of a surreal feeling and experience. To the best of my knowledge, nothing important had changed. Prior to making this decision I had been perfectly happy working on the factory floor. I had been perfectly faithful as well. I love my husband and he has not done anything that would make me angry towards him. The only event, well two events, that have begun to alter my opinion of our marriage. is that he has been unemployed due to the economy and during his time at home he has become fascinated with the idea of sharing me. Of course, I have told him, in no uncertain terms, that he is a pervert and that I would not go against my marriage vows for any reason.
The next week I began working for Robert and I was assigned a wonderful desk just outside his door. Because of the way the office was laid out, there was very little human traffic there. The only people who came to my boss’s office were a few select vendors and potential customers. If the person was important enough to be allowed back to Robert’s office, he or she was treated very well and most of our interaction was in the attached conference room.
I had barely organized my desk on Monday, when on Tuesday my boss asked if I could stay for a few minutes, after work, to discuss my salary. I was pretty sure of what he had in mind, so shortly before the close of business, I went to the ladies’ room and made sure that I was extremely fresh down there. A few minutes after five, Robert asked me to make sure that the office doors were locked and to come to his office.
I locked the doors and returned to stand in front of Robert. He directed me to sit in the chair that was placed along side of his desk. Prior to taking this job, I had always been faithful, but I was used to men looking at me in a way that could not be interpreted as anything other than them wanting to have sex with me.
Today, Robert, who has always been self-confident and completely in charge, seemed a little shy and unsure of himself. When I asked Robert what I could do for him, he blushed and looked away. He told me that I had proven myself during our meeting and that he still wanted our first time to be in a fancy hotel, but he needed more of what we did after we returned to the office. His change in demeanor, pleased me and I asked him, like he was a child, if he wanted to see my boobies. He nodded yes and started to say something else, but I put a finger on his lips to silence him.
I asked him if he wanted to see what a woman has between her legs, again he nodded, but this time, he stayed quiet. I could tell he wanted to say something. I teased him and asked him if I could play with his big, hard, cock. This time he nodded his head vigorously. I was smiling because I wanted to feel his hard cock as well.
I rolled his chair back a foot or so and stood between his desk and his widespread legs. Since I was wearing a dress, I raised it just enough to give him a peek of my underwear. When I dropped the hem of my dress, he instantly looked disappointed, but I quickly had his attention again when I began to undo the buttons down the front. I had a little mercy on him and after I had opened several buttons, I shrugged the dress from my shoulders and let it fall to the floor. I was standing in front of my boss in my bra and panties. I had a pair of thigh high nylons on, and I had been totally nude the night we returned to the office but then it was quite dark. Right now, his face was less than a foot from my body, every light in the office was on and I am sure Robert could see everything.
Now I was the one blushing because Robert was going to see a lot more soon. I was enjoying the power I had over him, but I knew that it was a case where he had given me the power, but he could also take it back whenever he wanted to. I reached behind my back and tripped the hooks of my bra. I let the bra fall forward and my boobs were just inches from his face. When he reached for my breasts, I playfully slapped his hands away. I spent maybe a minute lifting and cupping my breasts, right in front of his face. I massaged them and pushed them together and then gently pulled on my nipples. Robert looked like he was about to begin drooling.
Only one piece of clothing left to remove. I stood and carefully pushed the panties down giving him a perfect view of my womanhood. Robert started to reach for me again but caught himself and sat on his hands. To tease him, just a bit more, I sat back onto the edge of his desk and opened my legs wide. I leaned back and began rubbing myself down there. Using one hand, I used two fingers to open my lower lips and then used my middle finger to diddle myself.
From the time Robert had asked me to lock the doors and come to his office I was pretty sure that sex was on the menu. That gave my body time to get into the mood and when I stuck my finger into my vagina, I was very wet. I briefly closed my eyes to enjoy the sensations I was giving myself and when I felt Robert bumping the inside of my legs, I opened my eyes. He had dropped his slacks and underwear, and it was his hard cock that had bumped the inside of my thigh. I quickly caught his manhood and directed it away from my vagina. Robert assured me that he was saving that for when we had all night. Robert pulled me close with one arm and used the middle finger of his other hand to penetrate my cunt and finger me hard. I came.
Rather than continue his assault on my pussy, he pulled his finger from my body and presented it to my mouth to lick it clean. I had a pretty good idea what I tasted like, but this was the first time I tasted myself fresh from my vagina. It was deliciously dirty to suck his finger like it was a small penis. With that, Robert took back his power and authority. He gently but firmly pushed down on my shoulders and then sat back into his chair. He scooted forward and with me on my knees, his cock was right in front of my face.
I knew what he wanted and I allowed him into my mouth while looking up at him. The last time I had him in my mouth, I had basically used my mouth to catch his sperm so that it did not stain the backseat of his Mercedes. This time I gave him the very best oral sex that I knew how to do. As Robert got closer to his release, I did my best to deep throat him. He began to verbalize his thoughts, saying “Suck my cock, that’s what I want, suck it, suck me baby!” I later learned that his wife refused to let him use her mouth. When he came, I swallowed and then cleaned him up.
I went home and, again, made sure to suck on a breath mint in case what I had sucked on earlier had left an unusual taste in my mouth. I felt proud that I had not yet completely shredded my marriage vows, and I repeated the reasons I had given myself to make what I was about to do acceptable, at least to myself. My husband greeted me with a kiss, and he had a feel of my breasts, suggesting that maybe we could play later. Robert had given me a climax with his finger, but I still needed what my husband could give me.
We went to bed early that night and after a particularly good play time, we slept very well. I was not required to do anything for Robert, beyond what would be normal personal assistant duties for the remainder of the week.
Chapter 3:
In case I did not mention it earlier, we were paid every Monday, but the pay we were receiving was for the week prior. Robert felt that by paying us on Monday, there was less partying over the weekend, and his employees benefitted by having enough money to pay their bills. I had received my usual check that first Monday I worked for Robert because it was for time I had spent working on the production floor. The following Monday, I found my paycheck laying on my desk when I arrived for work, Monday morning. We were busy that morning, so I just placed the envelope in my desk. Around mid-morning I went to use the ladies’ room, and I grabbed my check to open it while I used the restroom.
I was aware that the position I had accepted was a much higher pay grade but how much the position actually paid, had never been discussed. During my interviews, I thought it best to remain confident and not focus on the rate of pay. When I opened the envelope, I nearly fell from where I was sitting. When I saw the total amount of my check, after taxes I was shocked and initially thought that they may have decided to pay me every month instead of every week based on the amount of the check. Rather than ask, I studied the check and the pay period was for only the last week. I was totally shocked. Other than the incident with Robert, after work, the work I had done was much easier and less stressful than what I had done for years on the production floor.
Near the end of the day, things had slowed down and I stepped into Robert’s office. He confirmed that my rate of pay was for one week and the amount was partially based on how well I had done on my interview. Knowing what he was saying caused me to blush. Robert made it clear that there would be many weeks where I “Had to work harder and nearly every day there may be some overtime.” But if I continued to do a good job, the checks would continue. I turned to leave but Robert called me back to the side of his desk and he reached up under my dress to feel my pussy. Because I did not expect to do anything sexual, I was wearing panty hose. His touch felt wonderful, but the pantyhose frustrated him. He ordered me to go to the ladies’ room and “lose the hose”. I looked over my shoulder and there was no one even close, so I pulled my skirt up a pushed the pantyhose and panties down as one piece. After sitting back down in the chair to untangle them from my feet, I placed them into the trash can and once again stood next to Robert’s desk.
This time his hand met bare skin, and he gave me pleasure to the point of having a small orgasm. After I had climaxed, He checked his watch and mentioned that it was after five. I knew what he wanted and told my boss that I would be right back after I had locked the doors. When I returned, he had already taken his cock out of his pants, and he was relaxed in his chair waiting for me to pleasure him with my mouth. This time I proceeded very slowly and kept him on edge for several minutes before I sucked him hard and allowed him to fill my mouth with his seed. Yes, I swallowed, I wanted to receive a check just like the one I had received earlier that day, every week. If it required giving Robert a little pleasure, then I was willing to do that.
Before I left, he asked if I could work a little overtime on Tuesday for him and mentioned that later next week there was a good possibility that we would have a business meeting at the steak house that he wanted me to attend. I was blushing but I eagerly agreed to be available. I advised Robert that I would see to it that my husband knew I would be home late a couple days next week.
I was excited and wanted to show my paycheck to my husband, but I realized that he would surely think I was doing something inappropriate to earn that much money. At the last minute I decided to wait until the next day to cash my check.
The following evening, I arrived home a little over an hour late. Robert had me lock the doors at the usual time, but when I returned to his office, he wanted to take things slow. He also wanted me to be totally naked. I complied and we made out on the couch in his office for nearly an hour. We ended like we had every time before with me needing to suck on a breath mint on the way home to cover any unusual flavors that may have lingered in my mouth. Even though we did not have penetrative sex, Robert’s finger probed all my orifices repeatedly. His long slender fingers had given me pleasure as well as making my bottom a bit sore.
When I walked in, I could tell my husband was a bit miffed with me. His first question was what was so important at the office that I had to stay late. Rather than get into a fight with him, I handed him a wad of cash from my purse that was half again more than I usually brought home. Suddenly my husband did not seem to care that I was working a bit of overtime. I did not tell him that I had left a deposit that was over twice what I brought home, in my personal account.
I should have felt bad about hiding money from my husband and I should have felt bad about the things I was doing with Robert, to earn the huge paycheck, but surprisingly, I did not. In Fact, what I was doing was exciting, sure I wished that I did not have to deceive my husband, but I was having no trouble doing what I had to do to regain out financial independence.
Before I was accepted to my new job, I was constantly worried about our finances and whether we would lose our cars or even our home. So far, using the Bill Clinton definition of sex, I had not had sex with anyone, to keep my job. I knew that would soon change.
On Thursday afternoon Robert called me into his office and closed the door. There was no one close enough to hear our conversation, but his actions told me this was a serious conversation we were about to have. Robert came right to the point. He asked me if I would go to the steak house tonight and act as Buck’s date. I must have given him a questioning look because he explained that I had apparently made a strong impression on him during the time they had interviewed me, and he wanted to be with me. I asked him if that implied that I would provide Buck with sexual favors as well. I was quite certain that was exactly what everyone had in mind and while I was prepared to let a potential client spend the night in my bed to entice him into signing a multi-million-dollar contract, it made me feel a little cheap to allow my bosses friend to have sex with me for no other reason than he was a friend of my boss.
Robert told me that anything that I did beyond having a meal and a couple of drinks with Buck was entirely up to me. He added that the two men who had enjoyed dinner with us a week ago were his best friends and they had been investors in his business when he began his business twenty years ago.
I agreed to go have dinner with Buck and left work for the steak house immediately after work. My husband had been informed that I would attend a meeting after work, and his only concern seemed to be if I would be paid overtime for the meeting. I went to the steak house knowing that I would have to give Buck some form of sexual pleasure before the night was over.
Dinner with Buck was surprisingly pleasant. We talked about many things. He had several questions about my husband’s and my finances. He understood our predicament and offered to provide us with a loan that was at a lower interest rate than what the bank was charging us. I was not prepared to try and explain, to my husband, why we were changing our loan from our bank to a loan from suspicious group of men that may or may not have been part of the mafia.
Our meal was served in a somewhat European style. It began with several small appetizers and a couple of glasses of wine. Apparently, Buck had preordered because no one ever took our order. We enjoyed the main course and the steak literally melted in your mouth. They served a special sauce on the side that awakened your taste buds like nothing I have ever had before.
Then of course, there was dessert and coffee. After that, there were drinks after dinner. I do not know Bucks’ relationship with the steak house, but no one ever presented a bill, before we walked out to Buck’s car together. I thought for a minute that I might not have to do anything with Buck, but when we approached his car, he asked if he had adequately courted and dined me. My comment to Trey must have made an impression on him. When I assured him that I had enjoyed my time with him he opened the door to the passenger side of his car and allowed me to get in. I did, and after he entered the driver’s side, he explained that he did not have a driver tonight. Buck encouraged me to sit next to him and when I scooted closer, he put his hand on my legs and began to softly rub my thigh.
I saw no reason to play coy and no reason to not enjoy what Buck was doing to me. I snuggled next to him and relaxed my legs enough so that Buck could easily get close to what he was wanting. His reserved nature was attractive to me and by the time we arrived at his house, well his mansion would be more accurate, I was looking forward to what Buck might do to me.
Because we started our date relatively early, it was only a bit after 8:00 PM when we entered his house and he immediately led me to his bedroom. When he took me into his arms, I was totally willing. Buck was a tender lover, and he knew his way around a woman’s body. I suppose I should have felt bad about what I was doing and what I was becoming. However, I didn’t feel much of anything. That may have been partially due to all the drinks at dinner. I was never tempted to have an affair, but I believe that if I was having an affair I would want to be with that person and I would be thrilled with what we were doing together.
Buck was different. I was totally enjoying what we were doing and I was an active participant. If I had been having an affair with Buck, I would have most likely expected that Buck and I would have a glass of wine and maybe dance to a few songs before going to the bedroom. With Buck, it was a forgone conclusion that we would go to bed together, since that is what I was being paid to do, and I would allow him almost anything that he wanted. It was a job, yes it was very pleasurable, but I did not have feelings that I would have had if Buck and I were involved in an affair.
Despite what men will tell you, few last very long after they are naked and in the bed. By 10:00PM we were finished and I had two loads of Buck’s cum slowly dripping into my panties. Buck hinted that he wanted me to spend the night and we might have sex again in the middle of the night or for sure have sex again in the morning. I teased him by telling him that taking too many of the little blue pills could give him a heart attack. I told him that because I was concerned about his health, I was going to go home, and he could schedule another date sometime in the future through Robert. Buck did not argue very hard because he was at least ten years older than Robert and I knew that Robert was in his sixties.
On my way home I made sure to use a breath mint, and I also stopped at a nice truck stop along the way. I liked this truck stop because they had individual rooms in the restroom rather than the usual toilet stalls. I had brought with me a regular pair of my panties and a feminine douche. I used the douche and cleaned myself as much as possible. I knew that, because of the way I was built, Bucks offering would continue to seep out of me for the next twenty-four hours or more. I also knew that my husband and I had been intimate just last night so he would not suspect the moisture in my panties belonged to someone else. I discarded my sodden panties in the trash receptacle and went home to my husband.
This was the first time I had cheated completely. I had come home with my vagina full of another man’s cum. Hubby was feeling amorous and at first, I felt a little awkward getting naked with my husband but once we began to make out, I put what Buck and I had done behind me and enjoyed making love with my husband. My husband gave me oral attention through my first orgasm, with him, that night, he never noticed Buck’s flavor, but I am sure he had at least a small taste of Buck.
I came quickly on my husband’s tongue. I am embarrassed to say that knowing that my husband was lapping up what Buck had left inside me, caused me to climax quickly. My excitement was in no way an attempt to demean my husband. It was just exciting to know it was happening. I mentioned that my husband has been talking about sharing me and one of the things he wants me to do, is to give his friend oral relief and after his friend comes in my mouth, my husband wants me to swallow his friend’s come and then kiss him. I was just giving him what he wanted, lol.
I was thankful that I had cleaned myself at the truck stop. I have read many stories where the man claimed that he could tell his wife had been with another man because she was extremely loose, down there. When I came on my husband’s cock it was totally different that the two or three times I had come on Buck’s cock a couple of hours earlier. Buck had a cock that was slightly larger than my husband and he had used my vagina for quite a while. It could not have been a full hour from the time Buck withdrew his cock from my love hole, till my hubby inserted his cock into my body. My husband was a better lover and even though I still had a few million of Buck’s swimmers inside me, Jim’s efforts made me feel loved.
During the next three weeks, life went on. There was no reason for us to leave town to prospect for business. Each week my paycheck was the same and I felt guilty earning so much money for basically being a helper to Robert. Each week, Robert would ask me to stay after hours for some overtime. I am a quick learner and at five o’clock I would lock all the doors and remove my underwear before reporting to Robert’s desk. While men may like to brag about how long they can last, I was usually in my car, sucking on a breath mint, within half of an hour.
We did have one prospective client that we met with in the third week. He was a local businessman who had inherited his business from his grandfather. Robert cautioned me that most of our interaction would be in the conference room and Robert claimed that the client was newly married, so he was not sure if the customer would be interested in more. I enjoyed being part of the negotiations, but I quickly noticed that even though our client was strait laced, he could not resist trying to peek down my top. He may have been a newlywed, but he was still a man. I made sure to find reasons to bend forward in front of him. I do not know if it helped but he signed the contract without any questions.
Monday morning, first thing, Robert informed me that we would be attending a seminar in a coastal city. The city was about as far away from home as we could possibly be from our home. After his announcement, Robert asked me to reserve a two-bedroom penthouse suite at the XXXX hotel. I will not mention the hotel’s name but even I knew that this was one of the finest hotels in the world. To say that it was a five-star hotel would be a terrible understatement. I studied the outline for the conference, and it was clear that the materials that would be discussed at the conference would be of little value to our company. The conference was a three-day conference, and we booked an additional day before the conference, so that we could rest before the nine AM starting time the next morning.
Robert looked at me with a gleam in his eye when I informed him that I had made the reservations. Even before I went to Robert’s office to inform him that I had secured reservations, I was pretty sure that this was his answer to his promise to make love to me in a five-star hotel.
Up to this point, I had to cheat on my husband only once. That was the time Robert asked me to go to dinner with his friend, Buck, from the steak house. We enjoyed an evening together and then returned to his home where I was the dessert for our evening. I was not particularly attracted or repulsed by my boss’ friend, Buck, so going to bed with him was not that big of a deal. That evening was a lot of fun because Buck was a skilled lover, however, it would soon slip from my memory of times I really enjoyed sex.
The date with Buck only lasted about three hours and that included the time we shared a few drinks and enjoyed a wonderful dinner at the steakhouse. I suspected that my date with Robert would amount to a three day and four-night marathon where I would perform every sex act I knew and probably a few that I had not learned yet. Rather than have sex and leave, we would spend the next three nights together and probably a good portion of the days as well. Robert agreed to let me purchase a new suitcase and leave it at the office. That way I could make purchases and not have to worry about my husband seeing what I was taking with me on my trip. It would have been hard to explain the sexy nighties and provocative dresses in addition to my regular work clothes. It would have been particularly hard to explain the large bottle of lube that I had packed because I knew that my body would probably be very well used over the next four days.
The night before I left, I had my work clothes packed at home and my play clothes packed in the suitcase in my office. I was a bit nervous and a bit excited to be flying across the country, first class, and I knew what would almost certainly happen. Before this I had only completely cheated on my husband with Buck. That was maybe an hour after I had several drinks before he took me back to my car. Over the next four days I would be giving myself to Robert and then sleeping with him for the entire night, giving him anything he wanted, when he wanted it.
Because I was leaving in the morning, I made a big production of wanting sex with my husband so that I did not have to worry about him finding another woman. I blushed when I told him that I did not want him horny and searching for a bed partner while I was gone, knowing that I would be screwed silly while I was gone.
My husband brought up the idea of me having sex with someone while I was gone and he asked if I would be unsupervised long enough to get picked up. I told him that I would most likely be alone most evenings, after dinner. Rather than looking for a job he presented me with a professional looking “Hall Pass” that he had created on our home computer. The pass specified that I could sleep with the man of my choice, but I had to tell my husband about it as soon as possible after it happened.
I kept the situation light by calling my husband a pervert. I told him that I would take it with me, but there was no way I was going to use it.
I suppose I was feeling a little guilty for planning to be my boss’ sex toy and giving him anything he wants sexually for the next four days but denying my husband what he had been wanting for years. Adding to my guilt was the fact that my husband had wanted to try anal sex since before we were married, and I knew that there was a very good chance that I would give my anal virginity to Robert this week. That was the main reason I had packed the large bottle of lube.
Those thoughts bothered me. I had accepted the other things I was doing and the things that I would be doing in the future, with almost no guilt, but I was suddenly feeling pretty low about not giving my husband what I was going to give to someone else.
I decided right then to make tonight as special for my husband as possible. I did not want to let my husband try using the back door because I did not want to be sore if Robert wanted to try while we were at the conference. Truth is I was afraid that anal was going to be painful. The lube I had purchased claimed to be specifically for use on my rosebud and I hoped that I could enjoy the act. If not enjoy, then at least be able to tolerate a man inside me there.
I knew that my back door was not an option, but I did know how to make my husband happy. Oral was usually not on the sex menu unless it was a special occasion, and oral to completion may have happened a half dozen times in our marriage. I gave my husband one of the most heartfelt blowies of our marriage and I did not stop until I had swallowed his first load. My husband was giddy and while he recovered, I cuddled with him and told him that I had been thinking about his idea of sharing me with another man. He perked up instantly and his cock perked up as well. This was as close to agreeing with his fantasy as I had ever come.
Of course, he was extremely excited, but I tempered his enthusiasm by telling him that I was not saying yes. I agreed that I wanted to talk about it. I added that I felt it would be unfair for me to do anything while I was at the conference; telling him that I wanted my husband with me when I did it for the first time. My husband gave me the best sexual encounters I have had in years. I started our session tonight, to assuage my guilt, but I was the one who benefited.
We pillow talked late into the night about what we might do after I returned home from the conference. Just before we drifted off to sleep, I added to my husband’s excitement by telling him that I might let a fellow conference goer pick me up and take me back to my room. I assured my husband that I wanted to wait until he was present before I did anything, but it might be fun to make out with another man for the first time since before we were married.
The next morning, I was up and out of the house before Jim was awake. I met Robert at the office so we could take his car to the airport. When I arrived, Robert was already standing next to his car, and my extra suitcase was already in the trunk. The flight was a direct flight, but the downside was that it was a six-hour flight.
Robert was the perfect gentleman when we boarded and began the flight, but shortly after takeoff, he asked the flight attendant for a blanket to cover my legs. I had worn a very casual sundress. I wanted to be comfortable, but I also wanted to look sexy for Robert. I thought the relatively short dress with a pair of sheer to the waist pantyhose, looked good and would be comfortable. It had only been a few weeks, but I was beginning to resent Robert using me as a sex toy. Not enough to stop him though.
Shortly after takeoff Robert began to rub my nylon cover leg, under the blanket the flight attendant had provided. He pushed my dress higher but since my lap was covered by the blanket, I was not worried. He did not do anything over the top but continued to tease me till I was so horny that I could barely wait for us to arrive at the resort.
The resort was everything I had dreamed of and more. I had never been to a premium resort, truthfully, I had never been to any resort. Anything beyond Motel Six was above my experience level. I think I was in shock or maybe temporarily drunk on the feeling that I was experiencing the life of the rich and famous. Even though I was ambivalent about sleeping with Robert for four days, I saw it as a minor cost for being able to experience this level of elegance.
Face it, I had done everything with Robert except let him put his penis inside my vagina. He had put it in my mouth many times, between my boobs and once he had bent me over and rubbed his penis between my thighs. With my legs close together, his cock was rubbing against my labia and had to feel very close to what being inside me would feel like. So, to protect my moral sanity, I was only counting the times a penis was inside my vagina. If I was honest with myself, I would have cheated on my husband many times. I knew that this conference was going to be a turning point
In my luxury drunken state, it was me who implored Robert to join me on the bed. Robert insisted that we limit our play to him receiving oral relief before we go to dinner.
The bed was huge; I guess they call it a California King sized. The sheets were silky and felt amazing. I wanted to cuddle and go to sleep, but I knew what was expected of me and yes, I swallowed.
Dinner was amazing. We each had a steak and the flavor was out of this world. The service was perfect and the side dishes had exotic names, but they too were fantastic.
In my world, back home, I had a habit of telling the person taking my drink order to “Use the good tequila”; Here, in this fancy hotel, I doubt they had my brand of tequila. I was feeling no pain when we returned to our suite, but Robert was even worse for the wear. No matter how hard I tried, he could not rise to the occasion. I sucked him until he fell asleep and then I fell asleep too. When I woke up, I was on the edge of the bed, as far away as I could be and still be in his bed.
When Robert woke up, he was apologetic for being unable to satisfy me the previous night. We ordered room service and within a few minutes we had one of the best breakfasts I have ever had, delivered to our room.
We ate and relaxed, taking our time to enjoy the wonderful food. It was strange but also exciting to be lounging on a bed, totally nude, next to Robert, who was also totally nude. Robert had seen my body many times when he insisted that I be nude while I serviced him after work. He has touched me everywhere as well. I, on the other hand, had never seen him completely nude. He was older than me, so his being nude was nothing special. Robert had the body of a man in his late sixties. He was in average shape, but he was soft around the edges.
I cannot emphasize this enough. I have always been a moral woman, and I have never cheated on my husband, that is, of course, before I took this position. I still am amazed that I have felt nearly zero guilt doing the things with Robert, at the office. or going on a date with his friend, Buck.
Possibly, I am willing to accept the sexual part of my employment because my hobby has always been reading romance novels. In those stories, it is not uncommon for a woman to have sexual adventures with numerous men. Maybe I subconsciously thought it is normal for a boss to have sex with his employee. What was happening now, with Robert, pushed those boundaries further than the most imaginative romance writer.
Doing things with Robert may have been easier because until now, my interaction with Robert has been transactional. For example, he tells me to lock the doors and come to him nude, or he tells me to get on my knees and, well you know. Simple tasks I do as directed to keep that large paycheck coming in.
We were both nude but covered with a soft blanket to our waists. Yes, I was next to him with my boobs on display. I knew why I was there and I was planning to enjoy it. We were in no particular hurry since we were both stuffed from the huge breakfast that room service had delivered. Robert his hand on my upper thigh. His ministrations felt wonderful.
I was fully aware of what Robert was doing and the anticipation of what was soon to happen had me wanting Robert to just take me immediately. Robert, however, was playing the long game. When his fingers moved slightly closer to my coochie, I relaxed my legs slightly. As he moved closer, I relaxed the leg closest to him even more and slightly bent my knee to give him easy access to my body. It wasn’t long before Robert was making good on his promise.
He made love to me for two hours. The intercourse was no better than what I enjoyed with my husband but the fact that it was with someone new that made our time together memorable. The part I remember best was when Robert performed oral on me. My husband gives me oral and it is very pleasurable, but Robert’s tongue was far superior to anything I had ever enjoyed. This may sound silly, but it felt like his tongue was very long and he knew just how to use it to drive me to orgasm.
That morning was the first time I received an orgasm from oral; it was that good.
After our morning exercise. We both dozed off for a while. This time I woke up entwined in Robert’s arms. Nature was insisting that I use the bathroom, so I slowly extracted myself from his arms and made my way to the bathroom. As I moved, I could feel my boss’s offering beginning to drip from between my legs, so I reached into my suitcase and grabbed a period pad.
I am past the age of needing period pads, but they come in handy to keep from soiling my underwear after sex. Robert must have been saving his load for several days because I was a mess down there. I showered and washed myself but still returned to the bed wearing just panties and a pad.
Robert wanted some attention from me and this time he wanted us to do sixty-nine. I could taste myself on Robert’s tool and I decided that I liked my flavor. Once again. I was the one being pleasured with his fantastic tongue. I climaxed again before Robert reached his orgasm.
This time it was Robert who needed the bathroom and as he made his way there, he noticed the fancy Hall Pass that my husband had created. He knew exactly what it was and when he returned to our bed, he asked me if I planned to use my hall pass. I denied that I would use it and explained my husband’s fantasy of sharing me.
Robert laughed so hard and for so long that I thought he might have had a heart attack. When he finally composed himself, he explained to me that my husband wanted to share me, but I refused yet I was in his bed and had entertained his friend without telling my husband so that he could enjoy it. I blushed and announced that “That’s Different!”
Robert insisted that I find someone and play with him so that I had a story to tell my husband when I returned home. I knew that there was a bar in the hotel, but I told Robert that I would be very uncomfortable trying to pick up a stranger.
Of course, my boss had the answer for me. He explained that he is a frequent guest at the hotel and he could arrange for me to be introduced to a gentleman of my choice. I am sure I looked skeptical because he went on to say that the man who had met us at the front lobby and who had arranged our table at the restaurant last night, had the responsibility of taking care of just a few rooms so that they could provide extremely good service, I had wondered how the staff knew our order and also wondered why we had not been presented with a bill. I guess Robert made a habit of taking his mistresses here.
Robert asked me what kind of man I wanted and even though I had not agreed to do this, I was impressed that I could not only order a man as a sexual plaything, but I could specify exactly what I wanted. I quickly decided that I would ask for a man that would be ideal and meet all my needs. If the hotel could not provide what I wanted, then I had my reason for not going through with my Hall Pass.
Robert smiled and asked if I wanted a twenty-something, hard-bodied gym rat. I made a face of disgust and explained that IF I did anything, I wanted the man to be slightly older than me, handsome, and someone important, preferable a wealthy businessman or someone independently wealthy. I declared that I would not just let them do it, I wanted to be courted and dined before going to bed with him. I thought I had set the bar high, but Robert did not seem concerned.
Robert punched a speed dial number on his phone and was soon talking to someone about finding a date for his girlfriend. I could only hear one side of the conversation, but it was obvious they had done this before. I had a knot in my stomach because I sensed that I had refused to do this for my husband, but I had agreed to be with a stranger for my boss.
We did not hear back from the man for over two hours. I was just beginning to think I may not have to be intimate with a new man because they could not find what I wanted. I was wrong; Robert’s phone rang and after some conversation I heard Robert tell the person on the other side of the conversation that “She will be ready at 7:00.” Robert was all smiles after they had disconnected. He informed me that my date would be another guest staying at the hotel, who wanted some company for the evening. I was told that my date would pick me up in our room, exactly at seven.
I was shocked, scared, nervous and embarrassed that two men had located a man for me to have sex with, but I was also incredibly turned on and my panties were flooded. Robert and I had another session after lunch, and he spent a lot of time teasing my bottom and teasing my mind about what I was going to do on my date. Robert refused to climax until I admitted that I was going to get fucked on my date. With that he pumped his seed into my body.
What had I gotten myself into.
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