Most people either love or hate Halloween. There are not many who are in between. Whether its dressing up, handing out candy or both everyone is different. In the sugar world, it can go 1 of 2 ways I have always thought based on personal experience. Your sugar daddy asks you to a Halloween party, you get dressed up and head out or you two travel to a new city and head out on the town there.
My own personal Halloween experience was a night to remember in a new city. It started and ended in Chicago, yes a bit chilly, but it warmed up quickly. Beginning from arriving at the hotel and getting ready for the night I was unsure what to expect. Of course he was ready before me and went down to the bar, which seemed odd because he has always waited before. However, I did not question it after he told me just to meet him at the bar. The next thing I know, there’s a knock at the door, it’s the bellman with what looks like to be dry cleaning. He let me know that the covered hanger was for me, handed it to me, and I shut the door. Sitting on the bed I knew I didn’t send anything to be cleaned as we had just arrived. Minutes later I receive a text from “him,” that says it should be your size, I’ll be at the bar when you are ready. Not knowing what to expect I lay it on the bed, pull the dry cleaning bag off, and there lies a red vintage, but looks brand new, flapper dress w/ headdress and thigh highs.
We haven’t discussed the plans for the evening and for all I knew we didn’t have any other than dinner. However, with this dress I was definitely thinking we needed to go somewhere. I finished getting ready, pulled the flapper dress on, and downstairs I went. There he was, sitting at the bar slightly turned in his seat waiting for my arrival. I remember coming down the steps and him turning and looking at me with a grin. This felt like a fairytale and it was only the beginning. The car was waiting in front of the hotel as we walked through the doors. Arriving at what looked like an office building, we get out and through the doors directly to an elevator 25 stories up the door opens to what looks like a hostess stand. It looked like an empty restaurant, but I could hear the chef in the kitchen preparing food as we were shown to our table. The restaurant was literally empty and we are brought to a table for 2 in a sectioned off area in the restaurant with beautiful black velvet curtains. I was thinking to myself “what is going to happen next?” We had a beautiful 7 course meal in an empty restaurant with the chef bringing out each dish.
From there, back down 25 stories and to the car as it seemed to get colder. We drive about 20 minutes arriving at the back entrance of what looks like a warehouse. At this moment in time I begin to worry as he can see it on my face he grabs my hand and says “it’s ok, this will be really fun.” Up the stairs at the back of the building, the door comes open and a hand sticks out of the dark doorway. As unsure as I am I reach for it, not to trip and step in. It’s almost pitch black and I can see more black velvet curtains with light around them and loud, but soft music. As we stepped closer to the curtains I could feel his hand on my back. Unexpectedly, I see a hand pull the curtains back and the light so bright with what looks like glitter raining from the ceiling I inhaled heavily and almost stepped back into him. I thought earlier in the night it was like walking onto a movie set, but this was so much more than that. It was like walking into the great Gatsby. Everything sparkled, many women in gowns and men in suites walked around quietly, and the glimmer and sparkle never dulled. There was champagne being passed and good conversation. This was a Gatsby Halloween like no other. We mingled, had cocktails, and danced. The night went by like a flash and into the early morning the car arrived and we went back to the hotel. We talked on the way as I told him how magical it was and off to bed we went. This would be a Halloween I would never forget.