Down The Rabbit Hole 6

Down the Rabbit Hole

My cell phone vibrated on the night table with an incoming text, waking me twenty minutes before the alarm clock was due to interrupt my sleep. It was enough to spoil my morning routine even though I felt no obligation to react to the sound. Sleepily, I stretched and reached over to cancel the impending alarm and picked up the phone to see which careless individual chose this uncivilized time of day to send an ear-shattering message. My heart jumped as I read the name on the message: Cory.

I sat up in bed and rubbed the sleep from my eyes before reading the body of the text. It had been over three weeks since I saw Cory and while he said that he would contact me in several weeks when he returned to town, I slowly let the thoughts of another meeting with him slip further into my consciousness as time elapsed. Reading his name on my phone brought me back to reality.

Opening the message, I read: "Hi, Jack. I will be arriving in town Friday evening and will stay in the same hotel as last time. Come over at 10:00pm and be prepared to spend the weekend. I will text you with the room number when I check in. Cory."

I had forgotten what dealing with him was like and reading the text brought a bit of anxiety, disturbing the serenity that I usually enjoyed in the morning. The world is populated by many different personalities and while I normally can navigate the paths from point "A" to point "B" without being phased by the idiosyncrasies of most, I always found it difficult to accept what I perceived as rude behavior. Cory was pleasant enough when he wanted to be, but he was direct, unforgiving and, most importantly, uncaring for the feelings of others. I believe this to be a common trait among certain individuals, male and female, and I initially placed myself in a position of acceptance of his behavior so I knew that there was nothing that I could do now to alter the relationship. He didn't ask if I was available to meet with him over the weekend but stated simply that I should come to his hotel room at 10:00pm on Friday and be prepared to stay for a couple of days. There was no discussion or compromise, but I knew that I would be there as directed.

I pushed the buzzer adjacent to Cory's hotel room door at 10:00pm sharp. If I learned anything from my last meeting with Cory, it was the benefit of punctuality when dealing with him. When the door opened, Cory was standing to the side in a robe, checking his watch and smiling. "Nice to see you, Jack," he said.

"Hello, Cory," I replied as I walked into the dimly lit room, "it is nice to see you again as well."

"Please make yourself comfortable. Would you care for a drink? Jack Daniels on the rocks if I remember correctly."

"Yes, that would be great," I responded as I placed my small bag next to the sofa before sitting down. Cory made two drinks and handed one to me before sitting in the chair opposite.

"Cheers, Jack," Cory said raising his glass and taking a long sip without waiting for a reply from me. I took a drink from my glass without saying a word. "How have you been?" he continued.

"No complaints, really," I replied, "but, if I am totally honest, I must admit that I became a bit anxious after receiving your text. It has been a few weeks and not knowing what to expect I am a little apprehensive. The last time that I saw you the circumstances were a little weird for me, being used by a stranger while blindfolded and tied spreadeagle to a table. You can imagine how I feel today."

Cory smiled. "But you came anyway."

"Yes, I came anyway," I replied as I took another long pull on my drink.

"Please make yourself comfortable, Jack. There is a nightgown on the bed for you and a blond wig in the bathroom. I will freshen up your drink while you change," said Cory as he got up from the chair.

Standing up, I walked over to the bed and picked up the lilac nightgown and took it into the bathroom, closing the door behind me. I was not expecting this, but I knew better than to question Cory. He had been clear with me from the beginning; do as he requests, and the experience will be pleasurable. Not following instructions brought pain but I still did not know how far he would go so I chose to be cautious.

When I got out of my clothes, I looked at myself in the mirror one last time before putting on the wig. I had to admit that the color suited my skin tone and eye color, so it was obvious that Cory put some thought into its selection. I slipped the nightgown over my head and enjoyed the feeling of its silky smoothness as it slid down my body, helping with the transition from Jack to a female-looking individual with a penis visible through the sheer fabric.

Checking my appearance and being satisfied that I did the best that I could with what I had been given, I opened the door and joined Cory in the sitting area, standing in the center of the room for inspection.

"My, you look lovely, Jack. Please turn around so I can see all of you. Yes, very lovely," he said.

"We are going to have to work on a proper name for you since Jack seems a bit too butch for such a feminine creature, don't you think?"

"Yes, Cory, I agree. What would you suggest? I am your creation after all," I responded.

"Hmm, something exotic I think. Perhaps Natasha, Camille or Aisha? Any preference, or another name entirely perhaps?" said Cory.

"I do like 'Aisha'. It sounds sultry and sexy when you say it," I replied softly looking into his eyes as I spoke.

"That would be my choice as well. It suits you. From now on you will be Aisha," said Cory with a smile. "We will have to work on the rest of your transformation over time, but I will admit that you fit the part very well without much preparation."

I took a sip from my drink and asked, "You said from 'from now on'. What does that mean? Are you officially changing my name?"

"When you are with me, here or elsewhere, you will be Aisha, whether you are in your street clothes or something else. I prefer thinking of you as a female, but I will let you decide how you present yourself. You will perform your duties as instructed, with whomever I select, and there will be occasions when you will be required to dress, or be costumed, as a woman. Will this bother you?"

I took a moment to consider Cory's words but eventually responded as he knew I would. "No, Cory, it will not bother me. I am here for your pleasure in whatever form it takes. If you want me to be a woman for you, I will do so. I am Aisha for as long as you want me to be."

Cory opened his robe exposing his erect penis. Clearly our discussion had gotten him aroused and he was anxious to show me the effect that it had on him. My nightgown could not hide my reaction either, and this brought a smile to his face. I walked over to him and knelt at his feet, staring into his eyes as I did so.

Without a word I leaned forward to take the head of his dick into my mouth, twirling my tongue around it several times before taking its full length down my throat. Cory leaned back in the chair moaning softly. "Aisha, my sweet cocksucker, you are so special to me."

I moved up and down on his stiff dick, occasionally letting the muscles in my throat massage the tip and squeeze the shaft. Cory did not have much control at this point, and it was not long before I heard his moans get louder and felt his movements become more intense before he erupted into my mouth with a loud cry of relief. His cock pulsed quite a few times before it finally started to shrink in my mouth, and I savored the taste of his semen.

Cory withdrew his dick and looked down at me as I tilted my head back, opening my mouth to show him what he had given me before swallowing his ejaculate and licking my lips. "My good girl," said Cory, "that was very pleasurable. Fetch a warm washcloth and wipe off my cock and then I'll have another drink."

It seems that the pleasantries were over and now I was going back to my service duties, not that I minded. It strange to float around in a nightgown while wearing a wig. I was still myself but not myself; I was Aisha. As I moved, I took on this alien persona, accentuating my movements in a much more feminine manner, keeping my knees closer together, bending at the knee when I stooped. These small changes felt more natural for me and seeing Cory's approving smile, I knew that they pleased Cory as well.

As I handed Cory his drink he said, "Aisha, I have a meeting tomorrow late-morning and I would like you to attend and serve refreshments if they are wanted. To present yourself properly you will have to shave your body and I have some new things for you to wear. There is nothing elaborate just nice lingerie with simple stockings and panties perhaps, but we'll see. You will need makeup and will have to get a manicure and pedicure to complete the look, so I booked an appointment for you at the salon in the hotel tomorrow morning at 9:00am. You do not have to worry about the specifics since I have given instructions and they will take care of everything."

"You want me to shave completely?" I stammered.

"Yes, do you have a problem with that?" Cory responded, a slight tone of annoyance in his voice.

"No sir, I just wanted to be clear," I replied. "Also, I may need help with some difficult to reach spots just to make sure that I do it properly."

"Not a problem. The staff in the salon will assist you as needed so simply ask them to check you over when you arrive," said Cory grinning, clearly enjoying the thought of my entrance into the salon asking for a full body inspection to make sure that I am properly shaved. I could feel my cheeks start to flush as the reality of the situation began to sink in.

"Aisha, are you troubled? You have a peculiar look on your face that would seem to indicate that you are unhappy," offered Cory.

"Well, to be candid sir, I was not expecting to take our role playing outside of these rooms and I find it slightly unnerving," I said. "You are asking me to go into a salon staffed with strangers, ask them to check me over to make sure that I am shaved completely head to toe, and then get a manicure and pedicure. It is a bit unsettling."

"You will also be getting a full makeover," added Cory, "you will leave the salon looking more like a woman than you ever imagined possible. You know that you can simply say no to this request if you so choose. Is that what you want, Jack, to say no?"

Hearing my name again gave me a jolt and I found it startling in a way. I knew that Cory was testing me, and the use of my real name was part of it. My brain was processing the options that I had but how should I answer him? Should I shy away from my new persona, from becoming the person that he wanted me to be, or should I submit to him yet again? This predicament was clearly more than I anticipated but, then again, what was I expecting when I arrived at his hotel room tonight? I found myself being bent to his will again and this time I will not only be in his suite, but I will be out in the open. It will be difficult to go back into the quiet shadows once I walk out into the daylight, but where will it end?

I looked at Cory, a bit self-conscious in my sheer lilac nightgown and gray-blonde wig, feeling the intensity of his gaze as he studied my reaction. Quietly I replied to him, "I cannot say no to you, Cory, but, so you know, I am uncomfortable with your request. I realize that I cannot step back into the past once I walk out of your room tomorrow morning, but I will do it for you...only you."

"You are truly my special girl, Aisha," said Cory.

It was near 1:00am when Cory suggested that I get some sleep since I had a big day ahead and I readily agreed. He let me remove the wig and nightgown and sleep in the nude as he did, and he held me close during the night.

It was right before 7:00am that Cory got up to use the bathroom and he nudged me awake when he returned to bed. I got up for the toilet as well and heard him tell me to come back to bed for a minute when I was finished but before starting my preparations. I did as requested and noticed that he had a very stiff erection when I got back under the sheets.

Cory did not waste any time rolling me onto my stomach and stretching my arms out in front of me. He applied some lube to my anus and smeared the remnants onto his cock before climbing on top of me. Holding my wrists, he whispered into my ear while his body weight forced his dick into my ass. "Aisha, today you will become a woman. It will be a unique experience for you, but I know that you can handle it. I watched you last night and saw how easily you adjusted to your new persona so it will only require that you relax and follow your instincts. I will be with you to help guide you along the path so don't worry about missteps."

Slowly Cory began moving his cock in and out of my ass, awakening sensations that I never felt before. It felt like the head of his dick was touching my stomach from the inside while the thickness of it stretched my anus to its limit. It was not pain that I felt but a tremendous gratification and satisfaction akin to the afterglow of orgasm. Soon his pace quickened, and I knew that he was getting close to a climax when suddenly and unexpectedly I shot my load of semen onto the sheet under my belly. Cory pushed deep inside me and released pulsing jets of semen into my bowels while moaning in my ear. "Aisha" was all he said as his body relaxed, and he went limp on my back.

When we separated I felt drained of all energy. My semen covered the sheet and my stomach while Cory's slowly began to drip from my anus. He looked exhausted but happily so. I forced myself from the bed and into the shower while Cory closed his eyes for a little extra sleep. I envied him but I knew that I had a lot to do and no time to waste.

Shaving in the shower was more complicated and time consuming than I imagined, especially trying to cover the entire surface area of my body. Eventually, I settled for doing the best that I could figuring that the "inspection team" will have to help me anyway so I rinsed off and put on some lotion to soothe my skin. Slipping into my jeans and polo skirt felt strange but comfortably so. New sensations greeted me with each movement, and I looked forward to feeling soft fabric against my skin when I dressed for the meeting later.

Cory was starting to stir in bed when I was getting ready to leave his suite and he casually reminded me to bring the wig since the makeup should suite my eye and hair color. I returned to the bathroom to pick it up and stopped to kiss him on my way out. "Have a nice morning," he said as I left.

I was greeted by a friendly woman when I entered the salon. "You must be Jack," she said with a warm smile. "We do not usually get such early appointments on Saturday, but it is nice to meet you regardless of the hour. I am Ami and this is my shop."

"My pleasure," I said while shaking her hand, "and thank you for accommodating me."

"Certainly, right this way, please," she said, leading me towards one of the rear dressing rooms. "You may leave your clothing here and put on a gown after we check you over and touch up any spots that you may have missed while shaving."

She clucked a few times as she inspected me and said that she would "finish the job." She smiled and began to put shaving jell into her hand to apply where needed. Soon she had gone over my body and had removed the leftover hair from my back, legs, shoulders and neck area. When she was done she applied a soothing oil and I felt like an eel although it was a wonderful sensation to the touch. She helped me into the gown and then guided me to the chair where I would receive makeup and the manicure/pedicure. "You have a wig I assume?" she asked.

"Yes, it is in the bag that I placed by my shirt and jeans in the dressing room," I responded. "Shall I get it now?"

"No," she said, "it's okay, I will get it and help you put it on when we're ready. We want to see how you look so that we can make sure that we have chosen the right mix of products for you. We recommend that you wear it for the rest of the day so that you get the full effect of your makeover without disturbing anything. Of course, we can touch things up if need be and you should feel free to consult with us if you wish to change your look or have this look refreshed. I will keep your name on file and give you my personal card so you may call me at any time for an appointment."

"Thank you, that's very kind," I answered while wondering if I would ever come back for another makeover. I didn't consider this to be a new phase of my life but who knows. So much has happened over the past several weeks since I first walked into that gay bar and ran into Cory I just don't know what to think anymore. But I am looking forward to seeing the result of this morning's efforts even though I still have my doubts about becoming passable as a woman. I am determined to relax and enjoy the moment.

The process began and I had the full attention of the salon's staff of three plus Ami. I could almost feel the transformation taking place as I relaxed in the comfortable chair with my eyes closed, focusing on my breathing, and thinking about the day ahead. Will this simply be another sexual interlude with strange men or does Cory have other plans. This makeover seems like a lot of effort and expense just to be able to watch me get fucked or sucking off Cory's friends for his entertainment. Will I get another whipping if I misbehave so he can see if the tears streak my makeup? Silly thoughts upon reflection but I have learned that Cory can be unpredictable.

Two hours passed quickly and before I knew it Ami spoke to me in her quiet, professional voice. "Jack, you will have to come back to our world now. We have finished our work and it is time for you to look at the new you."

I opened my eyes and saw the reflection of my new self in the mirror for the first time. My face had softened and changed so dramatically with the makeup, enhancing the hair color, and surprisingly I did appear quite feminine. The soft pink nail polish matched perfectly with the feelings of my new feminine self and the entire makeover was remarkable, more than I would have imagined at the outset.

"Ami, I am speechless. I never imagined that I would look quite... this good. You performed a miracle," I said. "Thank you."

"It is nice that you appreciate our work, but you were an easy client. With a little more attention to other details, you will truly be beautiful. We are prepared to assist with these things if you desire so please feel free to come in for a consultation if you want to discuss it.

"The polish on your toenails seems dry but I suggest that we give you some flat, open-toe sandals when you leave so that it does not get smudged. You can return them later or tomorrow at your convenience."

"Thank you, Ami. I appreciate that," I replied as I got up from the chair and looked at my full-length reflection in the mirror. "Not bad if I do say so myself," I commented.

"You are quite lovely, Jack," Ami said.

"Please call me Aisha," I said nonchalantly as I studied my face in the mirror.

"Yes, Aisha, you are quite lovely," Ami replied with a smile.

I carefully removed the gown and got into my street clothes, now feeling the full effect of being a female in men's clothing except for pretty, open-toe sandals. It seems strange but I felt that I would be more comfortable leaving in a light dress, or a skirt and blouse and I couldn't wait to get back to Cory's suite to get into a more feminine outfit.

Thanking Ami, Aisha walked out of the salon and into the daylight for the first time. Other patrons of the hotel gave slight glances and offered small smiles but nothing mocking or even disapproving from what I could tell. I felt good about my new look and most of the people that I encountered along my path seemed to share my opinion. One older gentlemen exiting the lift even said, "Good morning, Miss," as he passed causing me to smile and nod in polite response.