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Halloween 2014  

SubMonique101 68T
5 posts
2/14/2021 1:33 pm
Halloween 2014


There on the other side of the door was my ever present muscle guard. This was somebody new and he filled the role completely as he looked like somebody that had just finished several tours as a Marine. He was dressed in a tux, but his big barrel chest didn't hide the firearm he had in a shoulder holster, "You're needed at the front door. I hope you are ready for this." He turned to Mary and added, "It's the 'boss'. I took one last look in the mirror before slipping on my pink lace mask and rushing of the room with Mary right behind.

I was trying to move as quick as possible after just losing my anal cherry to a massive thick cock. Mary notice the difficulties I was having and slowed my pace down so I wouldn't stumble, "Catch up with your lover later. I've got a butt plug that might be perfect for your gaping pussy. I can imagine how empty you must feel right now. Want that big throbbing cock back in you again?" My head was spinning, but it was like she was reading my mind, "I do want to do it again." Mary began striding proudly next to her sissy as we were passing the bar area, "I'll need to hang on to this outfit as a part of my wardrobe. I like how you react to it." She gave her Katie a peck on the cheek as the guard watched us and just shook his head, "Good luck tonight. You have a lot riding on this, but I do like the way it has started."
She gave Kate one last inspection and straightened my feminine name tag as she confided one last thing before taking her position behind the bar, "Don't worry about the 'boss'. You probably won't even interact with him. Plus, he's a sweetie. I met him a couple years ago."

Rushing to join a line of employees at the front door, I settled in seconds before the metal garage door shook to life and raised the noisy metal open enough for a small of well tailored men to enter the warehouse. It was obvious who the leader was just by the way he moved with confidence, and the others appeared to either be protecting him or close associates. He was much than I had expected. This man appeared to be in his early thirties, and quite possibly in his days, was an avid body builder. The last two people to enter before the gate closed was Mr. Fred and a woman that appeared to be a legal secretary, or was it just her costume? As the of men talked amongst themselves I focused on the woman. Her business suit and slacks were very professional looking, and when she placed her leather brief case on a table to remove papers and gave them to the 'boss' it proved to she wasn't acting the part of a secretary.

The eventually came over to the line of employees, and not wanting to be noticed I dropped my head so that I wouldn't any of them in the eye. As they moved down the receiving line I could hear Mr. Fred introducing each employee and what their role would be that evening. My heart was pounding in my chest as I saw the men's shoes stop in front of a horny slave, "This is Katherine. She is assigned to food preparation and tonight." I finally looked up the 'boss' and was struck by his chiseled features, dark hair, and even darker eyes. When he finally spoke I was struck by his strong Australian accent, "Katherine, yes Katherine. Or do you prefer to be known as Kate or maybe is it Katie?" I pointed at my name tag, but added, "Whatever you feel is most appropriate, Sir." He smiled and turned to Mr. Fred, "Oh, I like this one. She's got the right attitude."

The legal secretary searched through her pile of folders before handing one with a red tag to the 'boss', "Oh, you're that Kate. Please take off that mask." I pulled it off so he could see my full made up image. He removed another couple black and white photo enlargements and scanned back and forth between the pictures he was holding and the sissy that was fully exposed before him, "Have you ever visited the land down ?" I answered truthfully, " Western Australia." He flipped through several photos and then read a page of information on the back , "I work of New South Wales. Sydney. My home is in the Northern Territory. Do you know where Darwin is located?" I just shook my head 'no' as he closed the folder, "You'll need to come visit someday as my guest. Just tell Fred or Paul when you are ready, and we will arrange everything." I politely thanked him for the invitation and told him I would consider it. He turned to Mr. Fred and said, "See, she's not so after all . Maybe a little slutty and submissive, but with an introduction to full feminization she could have been a prized<b> kinky </font></b>collared bimbo. Too bad for us that Kate is not a spring chicken anymore."

When the men finally reached the end of the line I heard the 'boss' ask Mr. Fred, "Who did you choose to provide my private this evening?" Mr. Fred waved a curvaceous red head dressed in a harem costume forward as she was closely inspected, "Very nice, but what about her?" I looked up and the Australian was pointing at me. He turned over a sheet of paper and looked it over before agreeing with his own decision, "Yes, she will do nicely." Mr. Fred gave me a stern look before they moved through the room full of decorations toward the rear of the warehouse. As everybody went back to work I watched them walk up a flight of stairs to an office with a large picture window overlooking the entire warehouse.

Within two hours there was a sizable crowd of revelers, but it wasn't as big as the previous year. The costumes were just as elaborate, so I felt comfortable in my sissy pink French maids uniform. I was on my feet for hours, and barely had time to get a moment with Mary. She was enjoying herself all night as she kept reminding me of how our evening started every time I visited the bar, "If you ever get a break your butt plug is waiting for you in the same drawer I placed my strap-on cock."

Part of my responsibilities for the night was to visit the upstairs office to get drinks and food requests every half hour. The first couple hours it was nothing out of the ordinary, as I was barely given a second glance as the men were involved in an intense meeting. Once while I was cleaning up a mess on a table, I noticed some official looking papers in the open brief case. Hopefully not drawing any attention to me, I casually moved closer to see what they might be. It was a set of contracts and also some art work for something called 'BLACK LABEL' productions.

It was just before two a.m., and the party was barely thinning , I climbed the stairs to the office, clicking on every metal step in my heels, but found it empty this time except for the 'boss' sitting on the edge of the office desk smoking a cigar, "Is there anything I can get you Sir?" He motioned towards a chair next to the desk, "Just a moment of your time." This was different all together, as I suddenly felt very feminine and vulnerable. I could hear the rubbing of my stockings as I slid into the chair beneath him, and it made the inside tremble, "Before I start, my name is Robert, and how long have you been Kate? I mean, when was the first time you dressed like that?" I knew the answer, and my response was quite appropriate, "Halloween, when I was five. We were poor and my mom suggested I go trick or treating dressed as a wearing one of my sisters dresses. I guess you could say that the genie was ' of the bottle'. I didn't want to take off the dress the end of the night and it wasn't until my mom and dad finally agreed I could go to sleep in it that I went to bed. I don't remember it happening, but my sister told me I was crying and depressed when I was forced to take it off in the morning."

I was met with silence, which made me shrink inside, until I finally looked up and saw Robert smiling, "From what I read about you I was expecting just a couple years...maybe three years, but not your entire life. Must be hard to juggle both lives." I dropped my head and nodded, "Well, you passed you're test with me tonight. Keep doing the good work for us through New Years, and I promise everything will all be forgiven, and then you'll have the choice to put all of this behind you. Take the next half hour off in the downstairs office." He motioned to a guard I hadn't noticed standing outside the office door, "Just lock yourself away until you're suppose to be back here. I'll inform Fred you're doing something for me."

As the guard entered the office Robert tossed him a set of keys, "Lock her up for half an hour." I thought it was a bit drastic, but when I found the tranquility of the office, when I heard the lock shut behind , I sunk down into the chair and looked the image of an exhausted sissy in the mirror. I closed my eyes for a few minutes before opening one of the bottled waters. When I moved back to the makeup table to check my , I remembered what Mary had told me and I couldn't stop myself from opening the drawer and pulling a fat silver butt plug.

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