Halloween
Halloween, All Hallows Eve, has many different meanings depending upon your upbringing and, more likely than not, your individual state of mind and attitude. Children enjoy the costumes and the candy, teenagers tend to enjoy the chance to be rowdy without much consequence, and those adults who have left the childishness behind, seem to enjoy the costume parties associated with the holiday and the opportunity to create a different persona for themselves even if it is just for one night.
After graduating college and joining the real world several years ago, I looked forward to this one night to become someone who existed but who shied away from the spotlight during the rest of the year. Friends would tease me about my choice of costumes and the familiar theme they had seen over and over since college days, but they had grown to accept my apparent lack of creativity as just that, a lack of creativity. The reality was different, and it suited my personality which came out on full display one night a year, a night when I could mix with people while looking through the eyes of my alter ego.
Each year I would dress as a woman, beginning with the slutty French maid costume, the slutty nurse, a version of Dr. Frank N. Furter from Rocky Horror and the like. In later years I chose more subdued and elegant outfits, an attractive secretary in a very short skirt, a businesswoman in a pencil skirt, jacket and blouse and tie, or simply a woman attending a party, someone in elegant yet outrageous drag. I enjoyed preparing my "costumes", those outfits that I meticulously maintained and wore on those other occasions when I knew that I could get away with it; I had a nice collection. I maintained my wardrobe for business trips and vacations or long weekends when I could escape from my regular life to become someone different, but I also used it as the foundation for my Halloween attire.
I attended a special Halloween party one year after receiving an invitation delivered to my office. There was a return address in an upscale neighborhood and after checking it out, decided that it was legitimate and prepared to attend.
I selected a costume that was new and very sexy hoping to make a lasting impression. It was a combination of Elvira, Mistress of the Dark, and Morticia Addams with my own sexy spin to it; black, low-cut in front with long, ragged looking sleeves fairly tight with slits up to the hip on both sides. When this was worn with black heels and stockings it looked fantastic and very hot, perfect as an attention grabber. I had a black, long-haired wig that I used on several occasions and finished the look with some dark but elegant makeup and glossy red lipstick. I found it exciting to get dressed and see the transformation from an average-looking young man into an elegant, sexy female creature of the night. What fun!
As I was being driven to the party I could see the driver glancing in the rearview mirror to look me over so I pretended to stare out the window with a slight smile on my face to gauge the reaction. Clearly my look was working and it made me feel wonderful. I hoped that I would have the same effect on the people that I encountered during the rest of the evening.
Entering the house I felt dozens of eyes turn in my direction and I could hear muffled comments, mostly from the men but some even came from one or two of the few women in attendance. I saw a few interesting outfits in in the cavernous foyer, a harem dancer in a shear, see-through top and loose pants, a topless Amazon Queen, a Spartan warrior, a legionnaire and the like but all very sharp. The host of the party, a middle-aged Middle Eastern man named Abdel, dressed in a white linen suit with a fez, like an athletic Sidney Greenstreet from Casablanca, came up to me and, extending his hand, kissed both my cheeks. His broad smile was very welcoming as was his greeting and he signaled for one of the waiters to bring me a glass of champagne to get the evening started. We exchanged pleasantries and he flattered me by saying how lovely I looked and that my outfit put everyone else's costume to shame. I could feel myself blushing as I smiled and while I may not have agreed with his assessment, I thanked him for the compliment. After a few minutes he excused himself to attend to newly arriving guests but kissed my hand before leaving.
I went on to mingle with the other people, a mixture of scantily clad Hollywood stars and starlets, pirates, and scary creatures who were having fun escaping recognition in their disguises. At one point I ran into a fellow named Jason who I knew casually from a conference we attended in San Francisco in the spring. I had met him along with many other people during the multi-day event but since we were from the same city we had a common bond and wound up talking during quite a few of the breaks. I met him again briefly in the bar of the hotel where I was staying while I was dressed as my alter ego, Rachelle, and we pretended not to have met before, simply flirting and chatting as strangers. We maintained contact via email and had gotten to know each other in a professional sense but I did not expect to encounter him at a random party.
As Jason and I made eye contact, he immediately walked over, a big smile and warm greeting followed. "Hi Robert, or should I say Rachelle tonight? It's nice to see you again" he said and kissed my cheek.
I was dumbfounded by the greeting and could not reply immediately. "You didn't think that I would remember "both of you", did you? How could I not remember such a beautiful person, but, then again, you were a blonde the last time I believe."
"Hello Jason, it's nice to see you as well. Yes, I was a blonde the last time we met and you're also right that I didn't expect you to remember. It is a pleasant surprise nonetheless and I'm flattered. Tell me, I can understand meeting someone from a business event in a common setting but how do you fit in here?"
"Abdel is an old client of my firm and I have known him for years" Jason replied. "I have a feeling that you will find him interesting when you get to know him."
Not only did Jason remember me but he seemed to know the host very well. How does he have 'a feeling' that I would find him interesting? Strange coincidences perhaps or just making conversation after a few drinks? I was a bit puzzled but with the festivities this evening I did not have time to dwell on it. Jason and I talked a bit and then went our separate ways.
Later that evening I ran into Abdel again and he acted more like an old friend than someone I just met several hours earlier. He walked around with me showing off his artwork, introducing me to other people and telling me about his business interests in various parts of the world in the process. Even though my intention was not to talk business this evening, I felt that I might be helpful to him in certain professional aspects so I broached the subject and offered to meet with him over the next several weeks to discuss matters of mutual interest if he was so inclined. He liked the idea and readily accepted my offer, asking that I accompany him to his office so he could jot down my contact information for his assistant. I agreed immediately.
Abdel guided me to beautiful wood paneled room away from the noise with one hand resting on my lower back as we walked. He closed the door after we entered and beckoned me to sit in a soft leather chair opposite his desk. He certainly fit the part of a wealthy international businessman and I was impressed by the surroundings, something I believed was his intention in the first place.
As Abdel started making a few notes, he asked if I preferred to be called Robert or Rachelle. His question surprised me since I introduced myself as Robert when we met and Jason was the only person who knew me by both names. Hearing the name of my alter ego spoken out of the blue by the host of the party startled me but I did not let it show. I told Abdel that he should list my contact as Robert but, smiling, said that he could call me Rachelle in private if he preferred. He smiled back and said that he would prefer Rachelle between us and that he would always think of me as I am now, his woman Rachelle, Mistress of the Night. I blushed and looked down at the carpet to break eye contact. Abdel told me not to be embarrassed as he finished writing down my contact details since I was safe here and among friends.
Abdel leaned back in his chair, studying me as I sat before him. He said, "Rachelle, you are very lovely and I would bet that you would be absolutely beautiful in a tailored business outfit."
Making a bit of a joke, I told him that I do look handsome in a suit as well and he laughed. "That's not what I meant," he said, "and I think that you know it."
I smiled but said nothing. He went on, "Not to get ahead of ourselves but, for clarity, if we enter into a business relationship I would work with you in this office as well as my offices in town and when we are together I will want to be working with Rachelle. She will be expected to dress the part of an executive and act accordingly in all settings and with all the people that we encounter in daily activities. Do you have a problem with that?"
I met his gaze and replied, "No, I think not. It is not usual for me to conduct business as Rachelle but you would be the client and I will do as you ask of course."
We sat in silence for a few minutes and then Abdel mused about how he would enjoy seeing me without my costume one day and I assumed that this was a tacit invitation of sorts. After a moment, I said that I would like to use the toilet and slowly, silently, I rose from the chair and walked into that room, closing the door behind me.
I looked into the full-length mirror and watched myself remove my slinky black dress. I stood there in my black wig, black Brazilian thong panties, black garter belt and stockings, black high heels and a narrow black ribbon tied in a bow around my neck. My body was freshly waxed and smooth. I had dressed for the evening preparing the ensemble with the possibility in mind that I might remove it with someone at the end of the night. I was not expecting what was happening to me now but at least I was prepared.
I opened the door and walked back into Abdel's office, standing to face him by the side of the desk. Abdel smiled and said, "That's my good girl, I like that you obeyed without question. You look beautiful by the way."
He rose from the chair and walked over to me, putting his hands on my neck. He gently pulled my head towards him and kissed me on the mouth. After a few seconds he slipped his tongue between my lips, probing. I responded with my tongue and pressed myself closer to his body.
Abdel slowly backed away saying again how lovely I was and how he happy he was that I accepted his invitation tonight. "We will get along fine", he said, moving to sit down in one of the soft leather chairs opposite the desk.
He unzipped his pants and took out his erect penis without saying a word, just looking in my direction to gauge my reaction. I knew what was desired of me and also what I wanted to do for him. I walked over, knelt between his legs and, looking into his eyes, took his hard cock into my mouth. As I slowly, rhythmically worked my mouth up and down Abdel whispered "Yes, that's it my lovely one. Take it deeper into your mouth, down your throat and hold it there."
