Disclaimer: this first entry is less intense on the sex. It’s intended to set up and build the story line and the world where these stories take place.
It’s so strange. Human beings. I’m no genius by any means, so don’t take any of this to really mean anything. I am a college dropout after all. I just find it fascinating seeing the way that human beings interact with one another in different environments. It’s especially interesting in my line of work. I never really paid much attention to it until one particular day off with the missus.
Officially, my job title is Head of Security for a large company. The company is probably one of the bigger fish in the industry and they’re located in a major city. We have prominent office space in the downtown area, so the need for security is obvious. I will refrain from divulging too much info about the business specifics because that would only make my job harder, and it really isn’t relevant to these brief shorts.
These shorts will be about the most interesting person I’ve ever observed, my boss. Or, one of my bosses for that matter. As Head of Security, I report to a lot of the top level executives in the company. I’ve slowly worked my way up from a security guard to where I am today. It’s taken me about 25 years. Don’t worry, these stories won’t be about the boring day-to-day stuff that I am officially in charge of, but instead will focus on the unique requests and assignments that I have taken on for one of the executives. I will not name them or their position to continue to maintain anonymity.
I do think it’s relevant to explain how these requests and assignments first came about, and this particular day off with the missus really reminded me of how it all started. We were at lunch at one of her favourite places on the outskirts of the city. The place is relatively popular and so it can be tough to get a spot sometimes. We were thrilled to be able to get a spot today as a gift from another exec at the company.
Being there for so long, they were well aware of my wife’s affinity for this place. They wanted to gift me this reservation as a nice gesture for me handling security and logistics for the last conference they had held for their department. The weather was nice and we had a nice spot on the patio. I was enjoying a nice afternoon beer and my wife was enjoying a sangria when we heard some glass hit the floor over by the entrance to the patio.
The waitress was drenched in what looked like wine and there was a fellow stood in front of her that I couldn’t quite get a good look at, but I knew I recognized him from somewhere. He was really laying into her because the spilled wine had splattered on his shoes and the bottom of his pants. Now, I understand that it can be upsetting to have a drink spilled on you and he had every right to be angry, but I felt like he was taking his anger a bit too far.
She was apologizing profusely and he just carried on with his rant. He began to call her a stupid bitch and told her that this job is probably the only thing she has going for her. He then started to demand to speak to her manager and was spewing some threats about getting her fired.
I won’t get into whose fault it was since neither my wife or I saw who was responsible for the spill, but I distinctly remember other patrons also whispering about what an asshole this guy was being.
The waitress finally relented and told the gentleman that she will go get her manager as she kindly asked him to calm down. Everyone there could tell she was flustered, and quite frankly it was putting a damper on the mood of the day. I quickly downed my beer, ordered another, and got up to go to the bathroom. My intention was to find the young lady and maybe back her up to her manager. I think it’s mainly because I remember all of the mistakes I made on the job when I was younger.
On my way in to the bathroom, I got the chance to get a better look at the asshole. He turned to face me when I tried to get by him to go inside. He was still at the entrance and I had said excuse me. He turned and we briefly made eye contact and he gave me this deeply flustered look. I could’ve swore that he even started blushing.
I was a little confused, but didn’t think much of it as I continued to make my way inside.
I wasn’t able to find the waitress or her manager, so I had just decided to go to the bathroom and relieve myself. It wasn’t until I was drying my hands that it really hit me. I knew this man, the asshole. Not personally, but I remember where I have seen him before.
It brought me right back to the night I was working an overnight patrol shift at the office. It was the night it all started. I was a security manager at the time and it had been my turn in the rotation to lead the night shift. I was making my routine check around the building when I had noticed a car that I didn’t recognize parked in the lot. There’s usually only a few people who work at this hour and I knew what all their cars (and one bike) looked like. This was definitely out of the ordinary and so I pulled out my walkie.
I paged the rest of the team and asked for a status report. I wanted to know if anyone knew whose car this was. Nobody on my team knew who it belonged to, but one of them did say that this car wasn’t there when they did their last round which was about 30 minutes ago.
This only made me more curious. I was on high alert. Who could be arriving at the office at this time of night and why?
I decided to investigate. I didn’t wanna spook the team, so I told them to continue as usual, but make sure they kept their eyes open for anything out of the ordinary. With that said, I began to make my up to check out each floor as I know there are a couple of people on working right now.
Nothing, just a couple of overworked middle managers.
I continued to make my way up until eventually I’m on the executive level. I still needed to check in on some cleaners and some of the lower levels, but I figured I’d drop by and say hello to the only executive who would routinely work at this hour.
I’ll be the first to admit that security was not my main concern. I was actually convinced nothing nefarious was happening and just wanted to spend a few minutes networking and getting my name out to some of the higher ups. This seemed like a great opportunity. I would start some small talk under the guise of a security check-in.
Instead what I found was… odd to say the least.
As I approached his office, I could see the lights on under the doorway. I knew he was in there. In my eagerness to go and say hello, I didn’t really notice the noises coming from behind the door.
In fact, I even knocked a few times before I noticed.
“Hello, Mr….”
I had to stop myself because it had finally dawned on me what was happening. Just as I stopped speaking, I distinctly heard the executive, now my boss, say “work it, sweetie.”
I couldn’t believe what I was hearing. It definitely sounded as though he was having some saleswoman get him off. For a split second, I think I even heard someone choking.
I began to turn around and get outta there when I heard him shout out to me.
“Who’s there?” he had said.
I didn’t know what to do. I was frozen just a few steps outside his office. My back was to the door, but I wasn’t far enough where I couldn’t still hear him.
He repeated his question.
I decided to just respond and let him know I was doing my routine check and wanted to see how his night was going. So, I walked back to the door so that I didn’t have to shout.
I had given him my little small talk excuse of noticing a car in the lot and wanted to make sure nobody unauthorized had gotten in.
He shouted back that it was nice of me and he appreciated the check-in, but there was no need for concern. He explained that he had invited a guest over to go over some details about an account we have with them. He said his day was so busy that this meeting could only happen at night, and that he’s sorry to have caused any alarm among me and my team. He even went so far as to say he was going to get lunch for the crew during the shift tonight.
“Did I tell you to stop?” he said out of nowhere.
“Excuse me?” I asked in confusion.
There was no response. He just kept talking, and I eventually clued in that he must be speaking to his guest.
“Thanks so much, sir. The crew will love it. I’ll leave you to the meeting now” I had said, not wanting to be an interruption any longer.
“It’s no bother, in fact, we’re done here. Do you mind just escorting my guest out of the building?” he had responded before I could get outta there.
“Get up” he said, sounding a little bit annoyed. This time I knew he was talking to his guest.
“I said up” he followed in a much more authoritative tone.
I heard the shuffling of some high heels and a faint voice pleading with him. It was something along the lines of “please don’t make me do this.” The next sentence I heard very clearly.
“If you want us to keep our account with you, you will do as you’re told” the executive had said firmly.
The next thing I knew the door opened and out comes this sexily dressed woman. Or at least, I thought they were a woman at first glance. It turns out they were a sissy. That’s what the boss likes to call them.
The most interesting part though, was that this particular sissy was the asshole who ruined the mood of my lunch. It’s so strange to see him behaving this way with the waitress. Loud, obnoxious, flat out rude. It was such a contrast from what I had seen that one night all those years ago.
He was dressed like a high class escort that night. I remember the purple dress and matching stiletto heels. His medium length blonde hair was pulled back in a sort of ponytail. He had glossy red lipstick that was slightly smeared around the edges of his mouth, and I think I even remember his knees being a slight shade of pink obviously from being on his knees just a minute ago. His cheeks were bright red to match his lips and he hung his head in shame as he quickly shuffled by me making his way to the guest bathroom down the hall. He looked pretty good, very passable as a woman if I’m being honest.
The executive walked out right behind him, giving him a swat on the ass as he strutted away from us. The boss stopped beside me, put a hand on my shoulder and simply said “make sure the little bitch gets out of the building safely, discretely if at all possible” and walked back in to his office closing the door behind him as if everything was completely normal.
I waited by the bathroom for a bit, not sure of what to do. I think I only did it out of curiosity, but I eventually went into the bathroom to let them know I would be escorting them outside of the building through the safety stairwell.
What I walked in on was completely different than what I had saw walk in. There was a briefcase open on the sink and the heels and dress were inside it. He was standing there naked except for a little purple g-string. I don’t think he noticed me right away as he was busy wiping away his makeup. I could see the little bulge at the front of his panties. It wasn’t the typical penis bulge, it was something else.
I’d later learn that he was in chastity, but that’s not the point right now.
He was quite literally speechless when he finally noticed me. He just grabbed the briefcase and went into one of the stalls. I stood there stupidly, but thankfully he came back out in a couple of minutes. Now he was dressed as a man. He was wearing your typical sales person business suit.
He quickly walked by me and made his way to the stairwell. He’d clearly been here before. No words were said between us. You could almost smell his embarrassment, but I followed him out of the building all the same.
Later that night, the executive called me up to his office for a chat.
Back in the present day, I couldn’t help but be reminded of how the gentlemen seemed so meek and timid when in the presence of my boss. Yet here he was today, putting on this show of what my wife later called toxic masculinity. It was the complete opposite of the person I had encountered all those years before. Like I said, fascinating.
As I made my way back out to the patio, I saw him standing there. Tapping his foot with his arms crossed to show he was losing patience waiting for the manager to come out.
I made sure to get to him before anyone else could.
I made my way right by him, didn’t look him in the eye or anything. Just said “drop it, sweetie,” in the same tone my boss had used way back when, as I walked past him and over to my wife.
“People are so fascinating aren’t they?” I asked my wife as I sat back down.
He left shortly after.