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I made it in life. Forty five year old me and my forty for year old wife have built up a successful business. Our children were bright enough to attend school and to built up a life on their own. My wife and me, we more or less had everything we ever dreamed off.

Everything except one thing: A sex life with each other. We still loved each other, we liked to hang out with each other, we even headed out on romantic dates, but in bed, the lights were mostly out.

We tried a lot over the years to light the fire again: From threesomes, heading out into swinger clubs, trying out different kinks, everything we came up with. It had a few highlights, we still have them from time to time, but on a day to day basis, our sex life is more or less over.

A few years ago my wife and me decided to open up our relationship. We allowed having sex with others, but we had to tell each other beforehand. Some of that telling beforehand and afterwards led to some great sex between the two of us. So we had found our formula, our kink, a cure for our dead bedroom.

It all worked well for about two years, until the day I came up with the great idea to fuck my secretary, my main assistant at work. She was hot, in her late twenties and I wondered why not. My wife had no issue with my doing, it even was a turn on for me.

But things between my secretary and me got sour over the course of a few months. She quit her job, she threatened me with some lawsuits, my wife – she is the head of human relationships in our business – had to take care of the situation and safe our business. And then she hired another female secretary for me. It didn’t took long and horny me was doing her. She just looked to good, her twenty six year old body was too curvy and she was too eager. And then shit hit the fan again. In about the same fashion like it had happened about a year before with my previous secretary.

That was when my wife had a talk with me. She told me that I could fuck everyone except people working for our business. Because she had enough of dealing with this shit. Then she told me that she would hire a secretary that was around fifty, about five years older than me.

When she realized that that was a turn on for me too, my wife came up with another idea: She hired a very promising twenty seven year old male human being. Because she knew, that I wasn’t into men at all. But well, she didn’t knew that my new secretary had a secret. A damn hot sissy one.

It was a perfectly typical Monday when my new assistant, my new secretary had his first day at work. My wife formally introduced the two of us, we shook hands and then I gave him his first orders. It took him a little bit longer than it should have to full fill them, but it was his first day.

He was already faster on day two, and it got much much better within the first month of him working for me. We two got along, work wise and other wise too, my wife just has a hand for hiring.

But something else was going on between the two of us. I somehow felt attracted to him. Something that has never happened with a man for me before. Well he wasn’t the manliest man out there: He either had no beard or he his shaving skills were just awesome.

He mostly was wearing suits, or jeans a shirt, some of the jeans were on the tighter side and well, he was on the skinny side. And his ass, was more curvy and female than your average male butt. But well, nothing to afraid off. Or nothing that actually really bothered me.

What bothered me was the fact that I more and more often caught myself starring at his damn hot but when he was bending over to get something out of a bottom drawer. Or that I caught myself smelling his hair more than once. And well, he wasn’t smelling like a man at all.

I honestly was a little bit confused, as mentioned above, I am normally not into men at all, but hey, maybe there was some bisexual hidden deep inside me. So I just accepted the fact that I got the hots for my male secretary. I wasn’t exactly sure if I should act on my desire or if I just should ignore it and go on with life. The last one, speaking out of experience, for sure was the wiser thing to do.

Because fucking another secretary of mine, driving them out of the business, giving my wife plenty of unnecessary work to do, it was a dangerous game. Because my wife, she was and is one of those people that went for my throat first and then was asking question.

And to my own surprise, I was able to keep my fingers off him. There were plenty of opportunities when we were working long hours together. He had caught me staring at him more than once.

So he knew that I had to the hots for him, and yes, as soon as he knew that he had caught my eye, he was showing off more in a surprisingly feminine way. I more than liked what I was seeing. But I stayed hard. Literally and figuratively speaking. But alone thinking off him, him sucking my hard one, his asshole wrapping itself around my erect dick, it made me fuck my wife more than good more than once.

When my wife asked me where the motivation came from after I had dicked her down, a smile appeared on my face: “My new assistant. He is a hot one.”

My wife let out a sigh: “Just don’t. Don’t fuck him. I don’t want to go through that shit again.”

I told her that so far, for about six months, I had been able to hols myself back. But I also told her, that it might happen one day. But that I was working hard to minimize the chance of it to happening at all. She was okay with my answer, but she was also a little bit concerned too.

But firing him was no option, because he actually was more than just good in his job. And he knew a lot of our companies secrets. So I kept on working with him, or he kept on working with me. And things went well, until we flew on our first company trip together. Three days, three whole nights.

After landing, after arriving at the hotel, something really annoying occurred: They had over booked the place. Or that was what they were telling my assistant and me. They only had one room for the two of us. One room with one big bed.

I was a little bit furious, no conference hookup fucking for me, but I calmed down fast. My assistant was working on solving the issue. He asked them, if they could put a second bed into the room. The receptionist nodded with her head. They actually put a second single bed in the room. It still sucked having to distribute a room with my damn hot assistant, because well, I know me and horny me, but well, it was better than sleeping in the same bed.

Then we moved into our room. We dumped our suitcases, we slipped into some more formal clothes and then we headed into a conference room. It was company talk and networking all day long. Even the dinner kept on going in that fashion.

Then there was some hanging out in the bar and it was then when my assistant excused himself. He told me that he was tired, so he asked me if was able to keep on going without him. I just nodded with my head and wished him a good night. Then I diverted my attention back to the feasible company partner sitting next to me.

An hour or maybe two later I found my way back into the hotel room. I expected that my assistant was already asleep and probably snoring out loud, but how wrong was I. When I entered the suite there was damn hot woman laying on the big bed. She looked beautiful and hot. And from the moment she caught my eye, I wanted her.

And yes, her looks were familiar. It was my assistant. Dressed to impress. Some hot lingerie. Totally smooth body. Some nice female curves. A good looking face, earrings and some very very feminine hair stile. Fuck, he was hot. There was an instant boner between my legs. And yes, reasonable me was gone. Horny me was in full control.

While walking towards the bed I got rid of my clothes. A smile appeared on his face when my hard one came out of my underwear. Then I placed myself on the bed next to him. He immediately took care of my hard one. Not with his hands, but with his mouth. He was a more than just well trained sissy and when I saw his caged dick through his panties, my dick got even harder.

His mouth wrapping itself around my glans, it felt nothing but good. He clearly had more than just some experience in sucking dick. He even took care of my balls, at first he squeezed them gently, then harder and harder. It didn’t took long and my moaning as filling the room.

My moaning got more intense when he took me down his throat. Every time my head went up and down my dick disappeared deeper and deeper inside his mouth. It had to focus myself to not immediately dump a load down his throat.

But he wasn’t able to take me balls deep. But my sissy assistant, he was no quitter. He asked me to grab his head and to push my dick down his throat until I was in him balls deep. A few moments later my hands were on his head and pushed the head onto my dick. Tears were running down his cheeks when I finally was in him balls deep.

And his caged dick was spitting out some sticky juices when it happened. It was then that my inner horny animal took full control of me. I just let go. I used his mouth, his throat like I normally would use a flesh light. I fucked his face hard and deep. He loved me for my doing.

But fucking his face, the awesome feeling of stretching out his throat, it soon wasn’t enough for me. I wanted to fuck him good. I wanted to fuck him up his ass until he was nothing more but a moaning orgasm filled mess.

So I grabbed him. I made him go down on all of his four. I grabbed the bottle of lube that was conveniently placed on the bed next to him. I lubed up my hard one, I poured more of plenty of it over his asshole. A shiver went through his body when the cold lube met his dirty hole.

Then I went in position behind him. I grabbed his waist, then I pushed my hard one inside his dirty hole. I went in slow, maybe even gentle. His asshole wrapping itself around my dick felt nothing but good. We both were moaning out loud when I went inside him.

Once I was in balls deep I gave him some time to adjust to the sensation of having something up his ass. Then I just let go. I fucked him hard, I fucked him deep, but I took my time doing so. I enjoyed the sensation of every thrust I gave him.

And he did the same. His more than just female moans were filling the room. Mixed with my male ones. His caged limp dick was bouncing back and forth while spitting out plenty of sticky juices. He was drifting off elsewhere, so was I.

One hard and deep thrust followed the previous one. More and more tension was building up. His eyes were running in circles, so were mine. All that mattered for the two of us was the sensation of my hard one going in and out of his needy fuck hole.

I gave everything while fucking him. Sweat was running down my body. Sweat was running down his body. My inner horny animal was in full swing while I worked myself, while I fucked the two of us closer and closer to an orgasm. It all felt so good.

Then I pulled back and forth once more. Boom, when I was up his ass balls deep, I came. My aching balls dumped their load deep inside him and up his ass. He came with me. His hole body was trembling, his balls dumped a gigantic load through his caged still totally limp dick. He collapsed. He was in orgasm happy land. And so was I.

I collapsed onto him. I kept on laying there for some time. Enjoying the post orgasm calmness. While regaining my breath. I actually gave everything. I fucked him hard and deep. And he, he loved my doing.

Once we both were ourselves again we had short chat. We both agreed on the fact that it was an awesome fuck. Then we both, one after the other, went into the bathroom and then we went to sleep. I took the big bed, he took the much smaller additional one.

On the next morning he was my assistant again. Still somewhat feminine, but wearing male clothes and his hair in a male way. He woke me up, he told me to hurry, because otherwise we would run late for the first conference of the day.

What followed was an typical company conference day that was followed by a night with me fucking my damn hot sissy assistant. The next day, the third and last day on our company trip was in about the same. I even declined some feasible conference hookups to be able to fuck my assistant elsewhere.

Once the three days and three nights were over we flew back home. Needless to say it was just the beginning of me fucking my damn hot sissy assistant. And well, my wife, she took the news of me doing my assistant more than just well. She actually was more than just turned on by what I told her. She wanted to join in.

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