tagFirst TimeCliff and the Boss's Wife

Cliff and the Boss's Wife


Hi readers, I just want to say (warn you) that this story does not happen fast like some. I personally hate to look at stories that go across 4 or 5 pages, but I also agree with many that a good story must be 'developed', and it is for this reason that I am going to take my time with this one. So there you have it! You have been warned that this story is long, and not only long, but also nothing much more than the 'build up', happens in the first half.

Believe it or not, most of this story is true, the only difference is that I am telling it from "Cliff's" point of view, and not from my own. I hope you enjoy it (if you still read on from here), and if you do, please send me e-mail if you wish to know more about me and my (wife and daughters) sexual experiences. While this story did not mention my daughter in more than the intro, she is in other stories on here and another site.


I did not have a uni degree, or the money to pursue one, and I did not have much chance of a high-paying job. The hours I worked each day were long, but the work was enjoyable, as I had grown up on a rural property so I was used to the lifestyle. I left school just after I turned 17, and took a position on a large cattle property about 50 klms out of town.

Hi, my name is Cliff; I want to tell you how my life changed, simply by being unemployed for a few months. I was just over 18 at the time when my life suffered a twist of fate; my boss died, and his wife sold the property, so I was left without a job. I had worked for them for almost 2 years, and my job entailed me riding the fences, either in the farm Ute, or on horseback. I would fix any fences, as well as muster the cattle when needed.

As the property was out of town and I did not have a car of my own, I rarely ever went anywhere, preferring to just laze about when I had time off. When I lost my job I moved into town and was lucky to have a friend who was willing to let me stay at his place until I found another job. Now this would not be easy, as the town only had a population of around 2000 people, but it was in a rural area, so there were countless large properties in the area where I would have a chance of work.

For the first few months I was not in a hurry to look for a job, as I had not really had time to do many of the tings that other young guys do when they leave school, and their family homes. I had only ever had a few alcoholic drinks when my previous boss felt in the mood; I had never had a girlfriend, and of course that also meant that I had never experienced sex other than with my hands or in my dreams. I wanted to change that situation and I decided that the local 'pub' would be the best place to start.

There were a couple of pubs in the town and the father of my mate's girlfriend owned the one I selected. I was introduced to the owner that Friday when we both went there. They seemed to be very friendly people, and soon I was made to feel at home. Over the next few weeks I would go and have a few drinks during the day when my mate was working, and soon the owner (Barry) and I were chatting away like old friends. I noticed that he liked to play 8-ball (pool) a lot, and as I also enjoyed a game or three, I was soon spending more and more time at the pub and filling my day.

Over the next few weeks I discovered a lot about him and his family, and one thing that puzzled me was why he was there alone most of the time. It turned out that they had a sick relative back in their town (about 5 hours away by car), and his wife and kids only came out west once a month for a few days to give him time to relax. This explained why I had not seen his daughter very often. One of his sons stayed there and did some hours each week when it was busy. Apart from that there were two women who also did some casual hours in the pub. As for available young women, there were very few of those around the town. It seemed that the only young women and girls around all had boyfriends or even husbands. The rest all left to the bigger towns looking for work.

On Friday and Saturday nights the pub got very busy and there was always a wait to get served. On one such time I was waiting to be served when Barry rushed past me, but did not stop. When I turned to see what was happening, he just called back to me and said to 'serve myself'. A minor fight had started so he was rushing to stop the two combatants. I jumped from my seat and rushed over to help him, and as soon as we had them settled and friendly again, we walked back to the bar.

"Thanks, Cliff. It's nice to know there is someone not afraid to jump in and help when trouble starts!" He said.

"Not a problem Barry, you treat me good, so why wouldn't I look out for your back?" I replied.

As the two casuals were both working that night, Barry sat down next to me and asked what I was drinking, as he would buy me one. I told him I did not expect that, but he insisted. He was trying to get the attention of one of the girls, but as they were a little busy, he 'swore' a little under his breath.

"Seems I will have to get it myself!" he apologised.

"Well Barry, if you were serious before about me getting my own drink, I would certainly like to help out and get both of us a drink. That way you can just relax for awhile" I stated.

He did not give my comment another thought, instead he just nodded and said he would have a rum and coke, and I should have whatever I wanted. I walked behind the bar and proceeded to get him his rum, and a Jim Beam for myself. From that night, whenever I was in there in the daytime and having a game of pool with him, he would tell me to get my own drinks. I did not realise it at the time, but he was 'sussing' me out as to my ability behind the bar. A few weeks later he rang me and said he needed to see me right away. As I was not busy, I went directly and asked him what the problem was.

"Not a big problem Cliff, more of a favour. I have to go out of town for a few days, as my family needs me. I was wondering if you would mind keeping an eye on the business for me for two days?" he asked.

"What do you mean Barry? Keeping an eye on things? But I have no idea what happens before and after you are opened, and what about the money, the ordering etc?" I quizzed him.

"That will not be a problem. There is a cleaner that comes in first thing in the morning; there is nothing that is needed as far as stock goes, and as for the money, I can make a few spare 'floats' for the tills. All you really need do is know how to lock the place up, unlock the safe to get the tills out. At the end of the day just put the takings into a bag, write the till number and date on a piece of paper, and place it in the safe. I can do the banking when I get back." he answered.

This was a sudden and unexpected request he had made on me, but also one that had me interested.

"So you want me to serve for a few hours during the day as well then Barry?" I asked with a grin on my face.

"Well that is up to you, but you don't really have too. I can roster the girls on to cover for the two days, but I really need a guy around in case there is any trouble like the other night." he said. And I don't expect you be here from open to close, as my son can do half a day and you can do the other half. That is if you don't mind," he added.

I thought about this for a few minutes while I sipped away on my drink. The idea appealed to me as I had always been interested in serving a few drinks myself, plus it gave me a feeling of being in a position of 'power' as I would control what happened for a few days. I quickly told Barry I was happy to help him out.

"Gee, you are keen and eager to please, you didn't even ask me how much I would pay you! Does that mean you will work for free?" he laughed.

"Well Barry, I had not even thought of that, but it doesn't really matter if you pay me or not. I think friends don't charge each other for helping out when needed" I joked back at him.

"Very true Cliff, but no, I will give you a few hundred dollars as you are doing me a big favour. If I leave the girls alone there is no one to watch them and the stock, so I could lose a lot more than that" he said more seriously. "Oh, and you are welcome to free drinks as well, as long as you stay sober when you are working!" he added.

Two days later Barry took off after first showing me the ropes and how to open and close etc. As there were only 2 bedrooms in his accommodation, and his son slept in one, he told me I could sleep in either his bed, or one of the two single beds in the room that were there for when his two younger children visited. The next morning I arrived early as I was doing the first half of the day and his son was doing the second half. As I had met his son many times before, there would not be a problem as we both seemed to get along with each other well.

The two days went without any trouble, and I felt happy that I could tell him this when he rang me on the second night. He was happy, but he also sounded troubled.

"Hmmmm, Cliff, I hate to do this, but can you stay another day at all? My car has some trouble so I am stuck here" he asked.

I quickly assured him that I had no other plans and that I understood his problem. I had been feeling good being here, and I told him I would take good care of his business for him. The next day his son did the first half of the day, and when he finished he said that he was going out with friends for the night, so he would not be back until the next day. I told him to have a good time and that I would be fine. He left an hour after the second girl started her shift. Around 6pm it was starting to get a little busy so every so often I would jump in and serve to help out, and then it happened. The girl slipped, and as she fell she twisted her ankle; dropping the glasses she was carrying, and when she hit the floor she landed on one of the glasses and cut her leg rather deeply.

The customers were very understanding and did not get angry about the slow service. Luckily, one of the local ambulance guys was having a drink on his night off, so he grabbed the first add kit and fixed her up, and then he offered to take her to the local hospital, as her wound needed a few stitches. This left me on my own. As Barry's son was out and I had no way of contacting him, I had to finish the night alone, and this was more nerve-wracking than I expected, as we were not due to close until midnight, and the bar had a lot of people in it. Luckily there was only one small 'scuffle' that I was able to stop quickly, and then continue serving.

When the night was finally finished I locked up, put the money away, had a few stiff drinks, and then went out the back to sleep. At around 6am I woke up, and needing to empty my bladder, I walked into the bathroom, where I got the shock of my life. There in front of me was a woman of about mid forties, and she was standing there completely naked. I don't know who got the bigger shock, her or me. She let out a sharp scream, and I think I may have as well. It took a few moments for us to both realise who the other person was.

"Shit! I'm sorry Anne. I did not know that you were here. I never would have walked in on you like that otherwise. I did not do it on purpose" I quickly tried to explain to Barry's wife.

"No Cliff, it is I who should apologise. You were not to know that I was here. I arrived an hour ago, and after the long drive I felt I needed a bath. I guess I should have woken you when I arrived, but you looked so peaceful I decided to leave you to sleep" she explained.

The strange thing at the time was she did not appear to be trying to cover herself, nor was she looking at my face, but rather her eyes were looking lower. "SHIT!" I thought suddenly. I was only wearing a pair of loose boxers, and my cock was standing erect, and it was straining at the front. I turned all shades of red as I tried to hide my erection.

"Don't be embarrassed Cliff, after all, you are at least wearing something, but I am standing here completely naked" she laughed.

I quickly left the bathroom and went back to find my clothes, but as I did Anne grabbed her clothes and followed me into the bedroom.

"I thought you needed the toilet Cliff?" she laughed. "It is free now."

I grabbed my towel and quickly excused myself, all the time trying not to look into her face, but that left only her naked body to look at, and that made things worse for me. I rushed past her and went into the bathroom. Once there I dropped my boxers and took a hold of my rigid cock and tried to have a 'piss', but it was so erect and throbbing from not only my full bladder, but the effects of seeing Anne naked, that I could not start the flow going.

Realising that I needed to calm my nerves before I could accomplish this take, I turned the shower onto old and hopped in, hoping the cold water would have the desired effect. As I stood under the water and waited for my cock to deflate, all I could think of was Anne's naked body. Apart from in books such as Playboy, etc., I had never seen a woman naked before that day. The more I pictured her body in my mind, the more my cock throbbed. I decided the only way out of this was to masturbate. It did not take long before I could feel my balls begin to tighten and I could feel the impending explosion that was about to occur, when suddenly the shower curtain was pulled open.

"Hmmm, did I do that too you?" Anne asked as she stood staring directly at my cock as it exploded.

"What are you doing in here?" I protested.

"Well, it is only fair after all. You saw me naked, so now it is my turn to see you naked. Now we are both even" she laughed.

"ummm ... but, but, that's not fair, you were not 'touching' yourself like I am, and anyway, that was an accident" I protested.

"Oh! Would you like to see me play with my pussy, would that make us even in your mind Cliff?" she laughed once more.

I felt myself turn many shades of red and did not know what to say or do. I was sure she was joking, but deep down inside I really was excited at the prospect of seeing a women play with herself; but I was also way too scared to even joke about it. I turned my back on her and tried to close the curtain. Anne left, but as she walked out of the room she called back to me.

"Hey Cliff, I bet you make a lot of girls happy around town happy with your equipment, don't you?"

I never answered her, as my mouth seemed to be locked in an open position. As I heard the door close I only then realised that my hand was still on my cock, and that my cum was splattered all over the wall; but not only that, my cock was still rigid; it had not died down, or at least if it had, it was now erect once more. What was I going to do, I wondered as I finally began the task at hand and washed myself. I finished my shower, dried myself and then went to get dressed; but my clothes were not there. I was sure I had brought them in with me, but maybe I had forgotten. Now I had to go back into the bedroom with just a towel around me.

When I got there Anne was nowhere to be seen; I felt relieved. I got dressed and went around to the office but she was not there either. Next I went to the kitchen, and there she was. As I entered I saw two cups of coffee on the table and I wondered who was the other cup for before I realised that it must have been for Barry. 'But hang on!' I thought if it were for him, then where was he, and what would he do to me when he finds out what had just happened out in the shower.

"Cliff, how do you like it?" Anne called to me.

"Ah... ummm, what do you mean?" I mumbled back in surprise.

"Your eggs silly, do you want then soft or hard?" she answered. "You understand what I mean? Do you want them hard like your cock before you played with it, or soft like after you blew your load?" she added as she broke into a fit of laughter.

After turning a bright shade of red once more, I finally mustered the words and told her I liked my eggs soft. I realised very soon that was not the right answer when she retorted with a disappointed tone and said that she always preferred it 'hard' first thing in the mornings. 'Was she purposely trying to goad me with her sexual innuendo's' I wondered, and where was Barry? I did not have long to wait before I had my answer to my thoughts.

"Cliff, Barry has some business to attend to back home I decided to give him a break from the pub. I will stay for the week, and Barry wanted to know if you would like a permanent job as his assistant manager," she asked in a 'matter-of-fact' voice.

"What do you mean Mrs...?" I started, before she cut me off.

"My name is Anne, and I hope you will call me Anne as I have never liked being called Mrs!" she interrupted with a terse tone.

"Ok, sorry Mrs, umm sorry, Anne" I replied. "Yes I would like to work here full time with Barry, but what about, ummm. You know, what about somewhere to sleep?" I shyly asked.

"Well Cliff, that is entirely up to you. Barry would rather you live in, and he said that you can decide what you want to do. As the kids and I are not here very often, you can sleep in one of their beds when we are not here, and that will be free. But if you want your own private room, then you can have a room in the accommodation area, but you will have to pay for that" she explained.

"But if I take the offer of one of the kids beds, where do I sleep when they are here?" I asked.

"Don't worry so much. If there is a free room you can have that on those nights at no charge, but if we are booked, then we can put mattress down and you can sleep there" she explained. "Unless you would rather sleep in our bed," she laughed.

'Was she for real? Was Anne trying to goad me into embarrassment, or was she just trying to keep my young mind totally confused?' I wondered for what seemed like hours, before she finally laughed and admitted that she was just 'fooling' with me. I agreed to stay on and work for Barry and help him, but I also asked why they did not get their son to do the job, instead of working only part time. She explained that he did not like the 'pub scene' and was only staying to help until his father found a suitable person to take over the majority of the extra duties. He would however continue to do a few hours each week to pay his board. It seemed to me that I had landed on my feet and into a job that I enjoyed.

The day began and we opened the pub and all seemed to go in a strictly business like fashion. Anne did the first half of the day while I went for a walk around town and then went and got my few possessions and brought them to my new 'home' and workplace. At 5pm Anne finished and I took over. As I was now going to work full time, Anne had explained that the 'girls' would do less hours, and that we (Barry and I, but sometimes Anne and I) would do the majority of the work. At times when it was really busy, whoever was there would just jump in and help. This I guessed was why I was classed as an 'assistant manager'; so I was sort of on call most days. But she did explain that I would have one total day off each week. This was fine with me.

By 9pm Anne said she would go to bed, but if I needed her for any reasons, then I just had to call her on the 'house phone'. I finished the night, and after closing everything down, putting the money in the safe, I had a couple of drinks and then went out to the 'managers quarters'. Forgetting about Anne being there, I did the same as the previous nights and just stripped down to my boxers and crawled into the bed.

"Well Cliff, you certainly seem to take 'assisting Barry' to a different level!" Anne laughed.

Shit! I had forgotten that she was there, and thinking I was alone, I had slipped into the bed (their bed) and was surprised when she spoke. I quickly apologised and jumped back out. I made my way towards where her kid's beds were (luckily they were not there), but as I did I tripped over something. She turned on the bedside lamp and just said to tell her when I was settled, and she would turn it off again. As the 'master' bedroom had been purposely built for the previous owners who had also had kids, it was a normal width, but it was twice as long as a normal room. I reached a bed and slipped under the covers and told her I was in.

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byAussie_Teacher© 8 comments/ 109783 views/ 12 favorites

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