Yesterday was Halloween; I worked at my office temp job. It is a prestigious law firm in the city, with a very conservative environment as one might expect. Earlier in the week, I was shocked to see a note on the Company Electronic Bulletin Board that we encouraged to dress in costume for a Halloween and there would be a luncheon.
I dress professionally for this office: heels, pantyhose, knee length pencil skirts, blouses, suits…you get the picture. Here was my chance to dress fun for the day. I thought about dressing up as a Mistress, but once I am dressed in that gear, my true dominant personality appears. I don’t think anyone would find it appropriate for me to have all the men in the office on their knees worshipping my boots and kissing my whip. Well, some of the legal secretaries would have found it amusing to watch their bosses groveling and being whipped. I decided to dress in a simple but very sexy little bar maid uniform my college days, short flirty little hot pink/black skirt and little top, with logo on it. I thought it might be rather provocative costume for this group and I might draw a lot of attention. I was wrong. Everyone was dressed in great costumes, but the one who drew the most attention was the Executive Director.
Have you ever noticed that so many guys cross dress on Halloween? Some of these guys really look silly, but today I was the one who was shocked when I saw the Executive Director (really high level guy) arrive dressed in a turquoise blue cocktail dress. I looked at him very carefully. The dress fit him to perfection. It had to have been tailored for him. It was just too perfect. He didn’t look silly, he looked rather elegant. He had a blonde wig, with soft delicate curls, make up applied to perfection and he walked in little black pumps like he did it every day. He looked just a little too good for this to be just a funny Halloween costume. The feminine details were just too perfect. He had what appeared to be an antique broach pinned to the dress. The hose were just the right shade to go with the outfit. He had delicate pearl earrings clipped to his ears. He was carrying a black pocket book that matched his black pumps, again to perfection.
I have never spoken to this man, but was aware of him because he was position with the firm. I approached him towards the end of the luncheon. I just couldn’t resist getting to know him. I looked right into his eyes (which matched the color of his dress) and I said exactly in the same tone that I would say to one of my sissies after dressing him up, “You look so pretty” with a soft feminine dominant voice. He responded like a good little sissy. He was glowing that I had discovered his true nature and that he has discovered mine with just a few simple words. Then he blushed and looked down. I discovered a sissy dying to come out and let the world know his true nature. I grabbed his chin, looked right into his eyes, said, “You be a good boy today for me.” His instincts just took over, he replied, “Yes, Mistress.” I smiled and returned back to the group of secretaries.
You never know where you are going to find a sissy in this city.
Mistress Koko
Are you ready to take this journey with me? I love all sissy boys, panty boys, and other feminine boys. They always do such a fabulous job making me so proud of them. Are you up for the task? If so, get your notebook out and let the assignments begin. I will train you to be the perfect sissy. I adore boys like you that are so eager to learn. I will teach you how to properly put on your makeup, teach you how to prance around in your pretty panties and how to put on your panty hose on those perfectly shaved legs. You will be my personal fuck toy when I am done with you. I will have you ready to get your little man pussy stretched wide open by one of my chocolate lovers. But you must be patient it’s not going to happen over night to a boy like you. So, get your lip gloss out and let’s have some fun transforming you into the perfect sissy slut.
