Halloween

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."

I did as instructed but since I couldn't breathe with my throat blocked, I looked into Abdel's eyes pleadingly for relief. "Just a little longer my dear, a little longer" he said.

After a few seconds which seemed like an eternity, Abdel told me to relax. As I gasped for breath I continued to work on his penis not wanting to lose the momentum. Abdel told me to take my time since it is a long night and he wanted to relish every minute of it. I continued holding his dick in my mouth while I worked my tongue around it and then let it out to lick the full length, something that he seemed to particularly enjoy.

Abdel reached for the cell phone on his desk and pressed several buttons. I stopped what I was doing and looked up at him. he smiled and then spoke into the phone. "Hi Jason. Come to my office please." Abdel ended the call and put the phone back on the desk.

I went to get up from my position but Abdel said, "It's okay Rachelle, stay where you are."

I did not know what was happening nor how to react to the situation but Abdel's instruction was clear. I felt my face beginning to get flushed and I had a warmth spreading throughout my body as I heard the knock on the office door.

"Come in," said Abdel.

Jason walked into the room, closing the door behind him. When he saw me half undressed and on my knees in front of Abdel sitting in the chair, he smiled broadly. "Wow, having fun I see."

"Yes," I responded and looked into Jason's eyes before lowering my gaze.

Abdel told Jason to come sit in the other leather chair and then addressed me. "Rachelle, don't you think that Jason deserves some reward for bringing us together? A small finder's fee of sorts?"

I looked up at him and replied, "If you feel that it is appropriate then I would certainly agree."

"Good. Jason, how do you feel about a little token of appreciation from me and Rachelle?" said Abdel.

"It is very kind of you, of course, but it's not really necessary." said Jason, shifting his gaze from Abdel to look down into my eyes while unzipping his pants.

I looked up at Abdel and then moved to Jason's chair on my hands and knees, stopping in front of him. Jason gently stroked his cock and then held it out to me. I looked at Abdel and then back to Jason before leaning over to take Jason's dick into my mouth. He moaned with pleasure as my warm mouth enveloped his hard cock and I began to move up and down on it, occasionally licking the head between strokes.

In what seemed like a few short minutes, I felt Jason's body begin to stiffen before groaning in the full pleasure of an orgasm. Hot cum shot into my mouth, hitting the back of my throat in the process. I took it all in before withdrawing my head and opening my mouth to show Abdel and Jason the full load in my mouth.

Abdel smiled. "It's okay Rachelle, you can swallow it," and I promptly did as I was told, licking my lips afterward.

Abdel looked at Jason, "You were right, Jason. Rachelle is perfect and if her business skills are as good as you told me, we will make a great team."

"Rachelle, you can get dressed now. I have a few things to go over with Jason and when you are ready we will talk some more."

"As you wish" was all I said before getting to my feet and walking into the bathroom, feeling two pair of eyes following my movements.

I looked at myself in the mirror and I was not sure how I felt about what I saw. I was still a lovely female-looking creature but I was changed as well. I acknowledged my alter ego and let her take control of me. I did not pretend to be someone else, I became someone else on full display. I did as I was told but also as I wanted, showing an inner strength as well as obedience.

I slipped into my dress and touched up my makeup before preparing to re-enter the office to face Abdel and Jason. As I opened the bathroom door I saw the office door close and realized that Jason must have just left. I was glad not to see him again this night since it would be uncomfortable to face a business acquaintance whose cock I just sucked at the whim of someone else.

When Abdel saw me he asked that I come over and sit down in the chair just occupied by Jason so that we could finish our conversation. He was glad that I was flexible enough to accommodate his requests without question and took it as a sign that we were a good match and were well suited for each other. I thanked him for the confidence and went on to say that I hoped to further earn his trust as our relationship progressed. At this point there was a knock on the door and Abdel simply said, "Come in," without taking his eyes off me.

Two women entered and closed the door; they were quite a sight to be sure. The first was in the garb of an African hunter with a pith helmet, a shear, loose-fitting dark green shirt and pants, dark tan boots and a leather belt that had places for ammunition. The second was fully nude but covered in body paint making her appear to be a jungle cat. She had face paint with whiskers drawn on her cheeks and a long cat-like tail apparently held in place by a butt plug. The hunter and cat had a chain leash between them, one end fastened to a collar on the cat's neck and a leather loop for the hunter to grasp on the other. They were a perfect couple.

The huntress said, "Sorry to bother you Abdel but we did wish to say goodnight and thank you for the lovely time."

"My pleasure," said Abdel as he rose from his chair, offering it to the huntress. When she sat down the jungle cat knelt by the side of the chair like an obedient dog.

As Abdel sat in his executive chair behind the desk he glanced at me and said, "Rachelle, I would like you to meet Danielle, the head of our far east operations, and her 'cat' is Adriana, her assistant. Ladies, may I introduce Rachelle, who will be joining us in a consultancy role and who will serve as my assistant in-house counsel." Danielle flashed a friendly smile and said that it was nice to meet me, but Adriana simply said hello with a slight edge that I couldn't understand.

When I arrived earlier, I saw Danielle and Adriana talking to some other guests and Adriana looked at me with clear dislike in her eyes. She had the same look now and her voice was cold as ice. Abdel must have noticed it as well and by his look you could see that he was going to set things right. Abdel continued the conversation by telling me about the far east business and then asked Danielle to give an overview as well. He went on to say that the various parts of the business were interwoven together and worked as a well-oiled machine. He stressed that there was a lot of give and take needed to support the operation and everyone had to be prepared to be on the giving end at times if we were to succeed. Abdel glanced at Danielle and mentioned that I had experienced some of the 'giving' end tonight in discussions with Jason and felt that I handled myself admirably, proving that I was a team player. Looking at Adriana but speaking to Danielle, Abdel said that he would like to expose me to the receiving end of company cooperation so that I understood how the operations meshed. He switched his gaze to Danielle and added, "Wouldn't you agree?"

Danielle shifted in the chair but calmly replied, "Absolutely" while looking directly at Adriana, who by now was staring at Danielle as if expecting support but not receiving it, said nothing. Adriana turned to look into my eyes and if looks could kill I would be toast. Nevertheless, she slowly crawled over to my chair on her hands and knees, stopping directly in front of me just as I had done with Jason, apparently waiting for direction. Intuitively understanding what was to come, I stared directly into Adriana's eyes and stood up. I moved my hands into the slits of my dress and slowly lowered my panties to my ankles before sitting again. I raised my feet towards Adriana and with hatred visible in her eyes she removed them and placed them on the floor by the chair. I gave a small smile as I lowered my feet onto the floor while lifting my dress and spreading my legs. My smooth, pretty clit beckoned Adriana and without taking her eyes from mine, she leaned forward and licked the head.

After first contact, Adriana closed her eyes and took my stiffening dick into her mouth allowing her warmth and wetness to finish my arousal. She moved up and down in an eager rhythm and I could immediately feel the sensations building within me. I looked over at Abdel who, by now, was quite excited himself and was smiling broadly; Danielle was stoneface, clearly not pleased with the current turn of events but unable to alter the course. I closed my eyes again and leaned my head back onto the chair, enjoying the experience of Adriana's talented mouth sucking my cock in front of her mistress/lover. With a tight smile I reached orgasm and let my semen shoot into Adriana's mouth before opening my eyes to stare directly into hers as her mouth was filled. She could barely contain her anger and let me know it by gently biting down on my dick to emphasize the danger this position posed to me. I softened my gaze and provided a genuine smile of appreciation which was greeted by the sound of Adriana swallowing my cum.