Sweet November

Friday, November 15th

I woke at five as usual. Normally I would be excited that it was Friday and that the week was nearing an end, but the way things had been going lately, I was having more eventful weekends than weekdays. Nevertheless, I got myself off of the floor and prepared for another day at the office.

As I showered and shaved I became even more aware of the aches I felt in my ass. Yesterday's ordeal must have been harder than I realized and masked by the on-looking crowd. Once I finished shaving and showering I took some Tylenol and finished getting ready before preparing Jess's breakfast and heading off to work. Jess allowed me to return to wearing panties instead of the chastity device, but I was warned not to pleasure myself without permission. I nodded my understanding as I headed out the door.

I did not have much to do once I got the office, although, I did have to explain where I disappeared to after lunch. Thankfully my fellow employees bought it when I told them I had a few properties to check in on for some out-of-town clients. Then I got back to tidying up the deal I finished yesterday.

Once I got everything turned in, I returned to my office to check my calendar and make sure I had everything done up to this point. I was surprised to find I was scheduled to be on vacation all next week, so I set out to find out what the office manager knew about this.

When I got to her office, she was a bit confused to find out that I did not know what was going on. She told me that Jess had called her while I was out a while back and set it up. Then she apologized because she thought maybe it was supposed to be a surprise and I was not supposed to know.

I told her not to worry about it, and that I would not let the 'cat out of the bag'. As I walked back to my office, I could not help but wonder what Jess was up to. I must have been border-line useless for the rest of the day, since I could not keep my mind on my work. I was dying to know what she had up her sleeve. Finally I was able to concentrate enough to get what needed to be done, done, to ensure all was well while I was out. Then, before I knew it, it was time to head home.

I packed up my briefcase and headed towards my car. When I got there Jess was sitting in the driver's seat. "Get in," she demanded as she gestured towards the empty passenger seat. I quickly tossed my briefcase in the back and complied.

As she pulled out of the parking lot Jess explained that a friend had dropped her off to pick up my car and that I would not be needing it this weekend. Then she proceeded to one of our favorite restaurants where we ate and chatted for about an hour-and-a-half. The mystery of the weekend still loomed over me, but I knew better than to ask any questions without permission.

Finally Jess paid the bill, and we left. She drove us to a nearby hotel and led me up to a room she had already checked into. I was a bit shocked to find the suite she had gotten was so lavish. It even had a hot tub right there in the room. She just stood near the door watching me while I took it all in.

"Strip," she commanded. Apparently she decided I had looked around enough and it was time to get down to business.

Once I was completely naked, she pulled a plastic bag from the closet and placed all my clothes inside. Then she opened the door to the hallway and left.

I waited a few minutes to see if she would return, but she did not. Then I began to search the room for any signs of clothes. I checked the closet and every drawer, but they were all empty. The only things I found were towels and one white cotton robe.

Suddenly the phone rang. I rushed to answer it. Sure enough, Jess was at the other end. She told me that the room was all mine for the evening and that I would receive no visitors. I was allowed to do whatever I wanted except pleasure myself. I could even order room service, but I would have to answer the door in the robe. The last thing she told me was that someone would come to pick me up at seven o'clock in the morning and I had better be ready to go. Before I had a chance to say anything, she hung up.

Wonder raced through my mind once again. I had no clue what she had planned. Based on her other surprises, I would not dare fathom a guess. Finally I decided to take advantage of the hot tub. I hoped it would help ease some of the soreness in my muscles, and it did.

After spending some time in the hot tub, I decided to get some sleep. I thought about getting a quick snack from room service, but decided not to, since I had nothing to tip. Besides, knowing Jess, I probably was going to need the extra sleep anyway. I set the alarm for six and easily drifted off to sleep under the covers of the soft, king-size bed.

Saturday, November 16th

I slept like a rock on the amazingly comfortable bed until the alarm went off promptly at six. I hit the snooze a time or two before I finally pulled myself out of bed and got in the shower. As I cleaned up, I realized that I only had shampoo, soap, a brush, a toothbrush, and tooth paste. I had no way to shave and nothing to hold my hair in place. I hoped this was planned and acceptable and did the best I could with what I had.

Then the phone rang. It was Jess again. "It is now 6:45," she said. "Someone will be arriving in about fifteen minutes to take you to your destination. Do exactly as they say, and you will have a wonderful time. I will see you this afternoon." Then she hung up. Once again, she allowed me no chance to speak.

I returned to the bathroom to finish getting ready. I did the best I could fixing my hair and preparing for the unknown. Before I knew it, there was a knock at the door. I answered it wearing the only clothes I had available to me, the robe.

"Good morning," the woman at the door greeted. "Are you ready to go?"

I was only slightly surprised to see the Asian girl from the previous weekend standing at my door. However, instead of the schoolgirl outfit I had seen her in before, she was wearing a sexy black chauffeur get-up, complete with hat and heels.

"In this?" I questioned, referring to the robe I wore.

"It's that or nothing," she responded and waited for my reply.

I shrugged my shoulders then tied the waist belt tight around me as I pulled the door shut and followed my chauffeur. We walked briskly down the hall towards the elevator which led us to the lobby. I was having a bit of a tough time keeping up with her and an even harder time keeping my robe closed. We got a couple of strange looks from the visitors in the hotel lobby as we headed out to the car. One man even gave me a thumbs-up sign as we walked past.

Finally we got outside, and she opened the back door to the Town Car for me to get in. Then she jumped in the driver's seat and took me to my destination. She said nothing as she drove. Curiosity once again ruled my imagination.

About twenty minutes later, we pulled up in front of a two-story house, white with blue shutters, which looked as though it was built in the early 1900's. It was beautiful and obviously well maintained. My driver got out of the car and came around to my side to open the door.

"Go on in. They are expecting you," she said, as she closed the door behind me and returned to her side to drive us away.

I looked around at the neighborhood quickly before I walked up the many steps to the front door and rang the doorbell. When no one answered the door right away, I got a little anxious. I hoped no one would see me standing on the front porch in just a robe.

The minutes, that seemed to pass by while I stood in just my robe out in the November breeze, were in fact only seconds when someone opened the door and let me in. The woman who opened the door was only mildly surprised by my outfit. She looked to be about forty years old by the style of her short curly hair and subtle laugh lines on her face. She was an attractive woman with beautiful blue eyes and a pretty smile. She had a medium build that was a little tough to make out as it was hidden beneath a white smock much like the ones I was accustomed to seeing on the women at make-up and perfume counters at upper-end department stores. She may have been wearing shorts or a skirt, but it was tough to tell by the length of the smock. Nonetheless, her legs looked tan and beautiful even though she wore comfy white tennis shoes in lieu of heels.

"Julie is waiting for you," she said, pointing to door at the top of the stairs. "Let me take your robe."

Figuring I did not really have a choice, I removed my robe, handed it to her, and headed up the stairs.

"Nice ass," she called, as I climbed the stairs completely naked.

"Thanks," I called back. I reached the top and knocked on the door.

The door soon opened and Julie stood before me. She looked me up and down as we stood there until a little smile came to her lips. Julie looked much like the woman at the door. I found out later that her name was Jenny and that they were sisters. She too, must have been close to forty. Her eyes were the same beautiful blue as her sister's, but her hair was long and straight. She wore it back in a ponytail held with a white rubber band that matched her smock. Again, I wondered what she was wearing underneath as no sign of shorts or skirt could be seen. Her shapely legs were the only thing extending from the bottom of her uniform down to her naked feet.

"It's nice to finally get to work on something as beautiful as you." Julie said, as she reached out and ran her open hand over my shoulders and chest. "Usually I just get hairy, overweight businessmen." Then she proceeded to walk around me caressing my back and buttocks before standing in front of me once again. She eyed my now-growing member with approval, and then gave it a quick squeeze with her thumb and forefinger, before turning back around and stepping all the way in to the room from which she came.

"Go ahead and lie down on the table," she instructed, as she motioned towards a long cushiony table in the middle of the room. Then she went to the sink and applied some oil to her hands.

I lay face-down on the table as I waited for her to approach. I could not help but think this was too good to be true. Just then she poured a small puddle of warm liquid on my back and proceeded to give me a deep-tissue massage. For the next forty minutes she massaged me from head to toe. The sensation was amazing, but I still could not help but wonder what was going on.

"Roll over for me, please," she said, as she added more oil to her hands in preparation to massage the front of my body.

I was so relaxed that I did not even think to try and hide the erection I had gotten from all of her touching. She seemed to be pleased that I had not, but instead of grabbing it, like I could tell she wanted, she began to massage my feet instead. Once again she worked her way up and down my body sending incredible waves of pleasure throughout.

After another half-hour had passed, she finally reached my groin. She massaged the edges surrounding my balls and cock, causing my erection to grow without hitting the most sensitive spots. Then she cupped and fondled my balls with one hand as she massaged my anus with the other. Pre-come began to soak the tip of my cock as she rolled my balls back and forth in her hands and gently rubbed my hole. By now I was beginning to moan softly and held back the temptation to beg for release hoping she would give it anyway. Finally the moment arrived.

With my eyes clinched tight from shear enjoyment, I felt her hand grab my throbbing member and slowly stroke it from top to bottom. She truly was a master of her trade, as she continued to fondle my balls while she slowly picked up the pace. My orgasm seemed to build as every second passed but it never quite arrived. The pleasure I felt was intoxicating as I now found it next to impossible to stay quiet or remain still while she stroked my cock methodically. The moves she did on my balls seemed to hold my climax in limbo creating an incredible sensation within me. I wanted so badly to come, but at the same time, I did not want it to end.

"Come now," I finally heard her whisper, as she released my balls, squeezed my cock tighter and then picked up the pace. Without another second passing, I felt my entire body spasm in one of the most intense, body-consuming orgasms of my life. As I shot my load, I felt the flood of warmth and coolness alternate through my body in indescribable fashion. The orgasm itself had not lasted as long as many I had, but the build up and explosion was like none before.

As my mind came back to me and the room stopped spinning, Julie took a warm washcloth and wiped me clean. "When you are ready, we will go to the next room," she said, and then threw the towel in a hamper and returned to the sink once again.

I sat up on the edge of the table to indicate my readiness. She glanced down at my now-soft member and then winked before leading me to the next room. Once inside, Julie inspected my body for any stray hairs and removed them. Then I was told to lie comfortably in a big old-fashioned bathtub. After that, she put a cool, jelly filled mask over my face, placed a small pillow behind my head, and told me to relax. After the experience I just had, that was not going to be a problem.

The next thing I knew, she began to fill the bath with a warm mud-like substance. Apparently, it was supposed to help me relax even more as well as help my skin. I was not going to argue. I was just enjoying the ride. Once my body was covered up to my shoulders she reminded me once again to relax and said she would be back in about an hour.

Shortly after she left the room I must have drifted off to sleep. The next thing I remember was Julie removing my mask and standing next to me. She asked how I enjoyed it and then took my hand to help me out of the tub. Once I got out, she pointed me to a shower in the corner to rinse off. I turned the hot water on in the shower and quickly rinsed myself off. As soon as I got done, Julie was standing there waiting for me with a fluffy white towel to dry me off.

She took her time patting me dry and then led me to the next room. I was handed the white terry cloth robe I had worn from the hotel and told to have a seat while Julie left me alone again. The chair I sat down in was a swiveling barber's chair covered in white vinyl. The room I had been led to looked like a small salon. It had a sink and cabinets like some of the salons I had taken my wife to, but just the one barber's chair.

In just a matter of a minute or two, Julie returned carrying a bowl of Chicken Alfredo and a glass of water. She handed the bowl and a fork to me and then placed the glass on the nearby countertop. "Enjoy!" she chimed, and then pulled a small stool in front of me and grabbed my right foot. She poured a little bit of lotion on my foot and toes and then massaged it in. Then she proceeded to the left foot. From there she went on to give me a complete pedicure, except for nail polish, while I ate my lunch. Once I finished my lunch she moved up to give similar treatment to my hands and finger nails.

I had never had a manicure or pedicure before, but this was definitely something I could see myself doing again. My hands and feet had never looked or felt this good before.

After a total of an hour had passed, she stood up and spun my chair around and leaned it back towards the sink and told me she was going to wash and style it for me. The shampoo and conditioner she used seemed to have some sort of menthol in it and caused my whole head to tingle while she rinsed it. Initially it felt weird, but once I got used to it, it was nice.

Finally she dried my hair and trimmed a little around the edges and on my neck. Then she applied some gel and styled my hair as well or better than if I had done it myself. As she spun the chair around to face the mirror, so that I could admire her work, I saw that my chauffeur had returned.

"Are you done with him, yet?" she asked pleasantly, but directly.

"Just about," Julie answered. "I just need to get him dressed and take care of a couple little details."

"That's fine," she responded back, "I am a bit early anyways. I'll just wait downstairs in the lobby."

Then Julie led me to yet another room. It was about the size of the last room but it contained only a white leather loveseat and several full-length mirrors. On the love seat was a medium-sized cardboard box with my name on it, but it still appeared to be sealed. Julie picked up the box and ripped the tape off effortlessly.

"Throw your robe on the couch and stand right there," she directed, as she sat down on the love seat to inspect the contents of the box. "Perfect. It looks like everything is here."

The first thing she pulled out was a small bottle of baby oil. She poured a generous amount onto her hands and then began to rub it all over my body. "This will bring out the definition in your muscles," she said. "The women are going to love you. A lot of times there are disgustingly buff men there that look like they never leave the gym. Other times there are disgustingly hairy and fat men who look like they never leave the couch, but you are neither. You obviously take great care of yourself, but you don't look like you're on steroids," she continued, rubbing the oil from the tops of my shoulders to the base of my feet without missing a single nook or cranny.

"I know I probably should not ask, but what are you talking about?" I blurted, as my curiosity got the best of me.

"Oh, she hasn't told you. Well, I can't spoil the surprise then." Julie said with a smile, as she reached back into the box once again.

This time she pulled out two ankle cuffs, two wrist cuffs, and a collar. They were like nothing I had seen before. They were made from leather but covered in stainless steel. That way they were comfortable against my skin, but flashy to all who beheld them.

Julie quickly attached the two ankle cuffs and matching wrist cuffs. Then she told me to get down on my knees. Once I was in position, she snapped the collar around my neck and reached back into the box once more. The next thing she retrieved was a black, braided-leather leash which she quickly clipped to the d-ring on the front of my collar. Then she pulled firmly up on it gesturing me to my feet once more.

Again she returned to the box. This time she pulled out a small container of ointment which she lathered all over her hands before standing in front of me.

"Put your hands on your head." She directed while she continued to coat her hands with the ointment.

As soon as I did this reached out and began to fondle my balls. She applied the cool substance all over them for a good thirty seconds. It felt cold but good. When she was done she wiped her hands on her smock and went back to the box one final time.

"The ointment," she said, "will keep your balls all neat and tidy by keeping them cool. Your mistress prefers them up as opposed to dangling." Then she walked back towards me with a small black velvet bag, which was a bit larger than your average coin purse, and a silver sequined thong. She handed me the bag, but told me not to open it. I was to simply hand it to my mistress. Then she bent over slightly and held the thongs out for me to put my feet through.

"I can do that," I responded, as I reached out to take them.

"No, I would be more than happy to," Julie followed, as she pulled them away from me and then held them out once more.

I could not help but be a little flattered by this older woman's charms as I stepped into the thong and she pulled it up into place. She even went so far as to pull on the waistband a bit and handle my package a time or two before swatting my ass and letting me know she was done.