Taking Care of the Boss
A Short Story
By Maryanne Peters

When I was told that young Kane Oster had a thing about wearing women’s clothing, I could not believe it, right up until it made complete sense. It was hard to believe it because he was on my security team – a bodyguard. He was not the biggest guy around but then bodyguards don’t have to be. In fact, being small enough to blend in works for some. But they need to be tough – they need to act fast and be prepared to get hurt, and they need to be prepared to hurt people – to kill if necessary. They need skills in firearms and hand to hand combat. I generally go for ex-special forces but he was recommended by my martial arts instructor for his sheer speed and aggression. Those sorts of skills don’t seem to fit with frilly underwear and fishnet stockings.

The kid was good-looking but not in an overly masculine way. There was a seriousness about him, and I know that others on the team said that he was good at his job. He was the kind of person who seemed determined, and those people are good under pressure. They know what to do when the bullets are flying. I found it hard to look past all of that secret girly stuff. It got so as I couldn’t look at him and not imagine him wearing women’s underwear under that suit. I found myself doing that too often. It got so bad that I seriously thought about replacing him. It was becoming a distraction, and in my world distractions can be dangerous.

And it is a bit gay. Even if he wasn’t a homo, it was queer. I mean I could see that he was a man and that he was in a man’s job. So, what was the dressing as a girl thing all about? I started to wonder in moments when I had time, and then I wondered when I should have been doing other things. Should I get rid of him just because I was thinking about him? What had he done to deserve being fired? I decided that the problem was me, and I pride myself as being a guy who tackles problems head on.

So, I called him in, for a private meeting. It was nothing unusual – I like to talk to members of my team to make sure they are on the ball. It is not just watching their performance but making sure they are not distracted. A bodyguard with troubles at home may be thinking about those instead of the threats facing the boss. I told him to relax – take a seat on the sofa so we could chat, informal like.

“I was actually thinking about having a woman on the team, because they can blend in a little better,” I began. “But then I heard from somebody – it doesn’t matter who – that maybe I don’t need to expand the team and bring in somebody that I don’t know already, because … maybe you can be that woman? I mean, I understand that you dress up like a woman every now and again?”

You should have seen the look on his face. It was like he had just taken a bullet in the belly, which is what he has to be ready to do. But I could see him plotting his next course. Bodyguards have to think fast and act fast, and he was a professional.

“I am not going to deny a fascination with women’s clothing, Chief,” he said. “I have a hobby. A lot of guys do. I don’t turn wood or go fishing. I do something else. It doesn't affect my job. I do it only outside working hours. When I am working, I am 100% on the job. You can count on me, I swear.”

“I am just looking at options,” I told him. “Like I said, it may be worth seeing what you look like … as a woman. We may be able to put that hobby of yours to good use.” I was floundering a little. The truth is that I wanted to see this other side of him. No, I needed to see her. Maybe he was starting to realize that. A good bodyguard should be able to read people. The thought of him as a woman was starting to get into my head. Like I said – I was the problem

“You’re the boss, but it is just a private thing, usually,” he said. “I don’t switch in and out. When I am Kaye I am all in. I would have to come to work as her, be her all day, and go home as her. Do you understand?”

“Make it Sunday,” I told him. “The boss is playing golf in the morning and has not much else on.”

“My choice of clothing is limited,” he said. I knew what he was saying.

“Give me your sizing, or rather Kaye’s dress and shoe size, and I will come up with something suitable,” I said. While women often play in shorts and a polo shirt, I had in mind something a little more feminine – a skort perhaps, and something sleeveless. The boss pays for all equipment and attire for his protection crew.

The truth is that I don’t like the golf thing. It really requires a minimum of three. I would go ahead to look for threats, and somebody needs to on the previous hole watching from behind, and then there is somebody with the boss, like a caddy for the day, although the boss drives a cart, so it is just handing him the clubs. Kay could do that. We could meet her at the golf club on Sunday, having called ahead to book out the whole course for four hours.

I don’t know what I was expecting, I just hoped that Kaye would look good. But as I said, not seeing him as a woman was not an option. I just had to get these visions out of my head. I guess there was a part of me that hoped he would look terrible. Surely that would knock these weird thought out of my head?

But we arrived at the club and went into the empty locker room. The boss had three other guys there to play the round, and one of them had a bodyguard too. I looked around for Kaye, but of course she would not come into the Men’s locker room, even in an empty clubhouse. She was waiting outside.

She was wearing what I suggested, and I could see that her legs and arms were smooth and tanned – she had the body of an athlete – a female one – toned rather than muscular. I had never noticed. She was wearing a wig – shortish and curled. She turned and my world went crazy.

I guess that I was expecting heavy makeup. You imagine that crossdressers use that stuff all the time. But the makeup was delicate. Rather than paint on a woman’s face it was just enough to block out whatever man there was in her. She looked fresh and beautiful.

“Who do we have here?” said the boss, obviously as impressed as I was – although that would not be a strong enough word for the way I was feeling.

“This is your caddy for the day, sir,” I said. “She is on my team and has all the skills. I will be going on ahead, one hole in front.”

“Have you added to your team without telling me?” he said, but he was not upset. I could see him looking her up and down lustfully.

“I am experimenting,” I whispered to him. I did not want his golfing partners to hear this. “It’s Kane dressed as a woman. If your buddies don’t notice it will open more protection possibilities.”

I just didn’t want the boss revealing that his latest female minder was not female at all. I felt that need to care for her that was new to me. I look after people for money, but this was different. I didn’t want to go on ahead, but I had to do my job and leave her to hers.

I watched her at a distance through my binoculars but only sparingly, as my focus was in front. I could see the boss and some of the other men, talking to her. She was smiling for them, but I could see that she was alert and watchful and maintaining a proper position at all times. This was pro at work, but finding it hard with the attention she was getting from four men.

They finished the round in high spirits. They would go to a known secure restaurant for lunch once they got out of the locker room, that was already covered by my man and theirs. Kaye was waiting outside.

“You’re not going in?” I asked. “There is nobody around for another few minutes.”

“I told you that when I am Kaye, I am Kaye,” she said. She was talking in a female voice, as if to confirm it. It was the first time I had heard that voice, and it was just as alluring as she was. The whole thing was starting to become a turn on for me, which was in itself, and uncomfortable thought. I had never doubted my sexuality before, but now it just reinforced that it was not just a fascination – it was definitely sexual.

“How was it today? Did anybody spot that you were not a woman?”

“No,” she said. “I take it you told the boss not to say anything about it. Instead, he spent the whole time flirting with me – no, the right word is sexually harassing me. And his pals too. If I wasn’t a professional, I would be upset.”

But she was upset. I could see it. Perhaps Kane would have shrugged it off, but not Kaye. She could not. What woman could or should?

“Are you Okay to see out the day, or do you want to … change?” I was hoping that she would stay.

“Like I said. I am a professional,” she said. She walked over the car and ran a few standard checks. We did not speak for the rest of that day, but I found myself constantly wanting to look at her. She moved in a way that was totally convincing. It was like she was a different person when dressed as a woman.

That evening the boss spoke to me about her. He said – “I really like Kaye working on you team. To be honest, I never noticed the other guy – the guy she was. I think that she might be useful for something I have coming up. Tell her to report to work dressed as a woman until further notice.”

It was awkward for me to tell her, but deep down I was ecstatic about it. Kane Oster meant nothing to me, but turning up every day to work alongside the beautiful Kaye, promised to be a joy.

What the boss had in mind was that Kaye would accompany him to a charity event as his date, and to offer close protection all evening. In many ways it made sense. A man moves around in classy company, and he doesn’t like to have a huge unsophisticated brute standing beside him, even though I was not that. The fact is that a woman beside him, especially a pretty woman, made him feel more relaxed and natural. All he needed to do was to make sure that she was elegant enough to be his date, and that meant spending money.

I saw her when we arrived. She looked like a runway model wearing something that might cost a small fortune. She told me later that she had rejected a few outfits that would not allow her to move quickly or to conceal the mandatory firearm, and she needed to wear something underneath to give her the knockout figure the boss requested. She wore a wig, but a styled one – I think they call it half up half down. There was jewelry too, and pierced ears to carry some of it. Her makeup was dramatic but still her natural beauty shone through.

I would be patrolling the halls outside the ballroom. Access to the event was controlled, but I still had a job to do which kept me occupied.

She rode home with him in the back while I rode shotgun in the lead car. I worried for her back there. Sexual harassment she had called it. My instincts were to protect her from him rather than him for anything. When they got out, I was there to hold the door for him to step out first and to call her to my side.

“I am not quite finished with Kaye,” the boss snapped at me.

“The gates are closed sir, and I need to go through tomorrow’s schedule with Mr. Oster.” I could see that the masculine name trapped him a little. He simply nodded and continued up the steps, leaving me standing beside the most beautiful woman I had ever known.

‘How did that go?” I asked. She looked troubled and I so much wanted to put my arms around her.

“He wants me to get breast implants,” her voice was emotional and barely controlled. “He wants me to take hormones and grow my hair and he wants me to have real breasts so I can wear what he calls ‘more appropriate clothing’. He says he will pay whatever it costs, including a new pay package.”

“You don’t have to do what you don’t want to do,” I said. But I was imagining that body with real breasts.

“To be honest, I loved tonight. I almost lost myself, and stopped looking at people as potential threats. I got caught up in just being a glamorous lady being admired by both men and women. This is so new to me. It was always a private thing, but now I am not sure that it can go back to being that.”

“You can be very useful as Kaye,” I said. “But you need to remember that this is a job and he is just your employer. He has no right to demand physical changes, and no right to treat you as a sexual plaything. But you have to admit, being Kaye may allow you to do your job better. If you weren’t her both of us would have been in hallway or behind a curtain, whereas you were right there.”

I guess that I was making a valid point, but the main motivation was that I did not want to see Kaye disappear from my life.

“I’ll think about it,” she said. Her feminine voice persisted, and now it trembled with uncertainty and fragility, making it even more womanly. As she walked away, I stared at her beautiful butt. Padding or not, I knew that I had to have that woman.

The choice she made was sensible, and I was left to explain to the boss that I had done a deal with her that would cost him, but be worth it. In that explanation I added a few things that recognized that even while only masquerading as a woman, special rights applied to female employees, and they applied to Kaye. It was pretty clear to me that he was not paying much attention to any of that, but that would not become apparent until later.

I had always been ambivalent about the boss. It is not up to me to make judgements about my employer’s character. He was not a nice person and was engaged in largely illegitimate if not criminal business activities, but a professional would be obliged to protect Satan himself if he paid the wages. You cannot let your opinions get in the way of your job. But I was growing to dislike him.

I remember when at some function with his pals he told all of them that his beautiful lady bodyguard had a cock between her legs. I found the very thought of it disgusting, but saying it out loud, doubly so. After getting over the amazement, everybody burst out laughing. I put on a disinterested face, but inside I was fuming.

To think that she had gone through that surgery and watched hormones rob her of sexual function and he should belittle her like that – it seemed monstrous. She, on the other hand, never lost her sense of duty. The hormones robbed her of muscle too, but she worked out to compensate and staying on top of her game physically, while appearing to me to blossom into womanhood at the same time.

It was love. I knew that now. The more woman she became the more right it seemed to me. My desires were not homosexual – I just recognized the woman in her before anybody else, including her. But it seemed to me that she now understood that there was no going back.

That made his attitude to her all the more ugly. To him she was a curiosity – somebody who could hang off his arm when it suited him, but otherwise be the butt of his jokes. But there was no doubt that he desired her too, in his own perverted way. When she dressed as he required, with her new breasts and her soft skin, and her long extended and colored hair piled up, I could see him leer. It was only a matter of time when his base instincts were let loose.

The problem for the boss was that she knew how to look after herself. I don’t know the details and I have suggested that she doesn’t tell me, but he had attacked her in a sexual fashion, demanding to see her “pissing clitoris”. She had put a sleeper hold on him and he was out cold when she called me.

“What are we going to do?” she said. For the first time ever, I noticed tears in her eyes. “I mean I have lost my job for sure, but as he struggled, he told me that I had ‘lured him into faggotry’ and that he would make sure that I was dead because of it. He knows people. You know that he knows people who could finish me.”

“I think that we need to take care of the boss,” I told her. After all that is what we are paid to do.

I decided that an assassination was what was called for. I had worked for him for long enough to know that it was a very likely event. He had plenty of enemies and had taken on protection because of one failed attempt. While I worked for him there had been at least three other “incidents”.

A bullet through the head as he slept seemed the best way. Clean and tidy. I needed an outside weapon with a suppressor and quietly forced access on to the property and into his bedroom – I could arrange all of that after the deed was done. But both of us wanted to add some explanation as to why we as his security team, missed this intruder. Call it professional pride. After the shot was fired we both worked on setting the scene and making the grisly discovery.

I have to say that the death of any client does not help with the CV of any professional bodyguard, but as a husband and wife team with our special skills we have been able to stay employed ever since.

It is our private joke that we know how to take care of the boss.

The End
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© Maryanne Peters 2025

I think it was Erin who suggested – “A mob boss discovers that one of his employees is a secret crossdresser, this intrigues the boss and he slowly forces the younger man into being completely feminized, at first she seems to be adapted to it but the boss is losing interest and the boss's bodyguard is really delicious looking....it wouldn't be the first time someone was assassinated by their bodyguard.” I turned it a bit by making our heroine a bodyguard.