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The Trip To Chicago
I got ready for work. Today I decided to wear a pair of wool slacks with matching jacket. They both were dark grey with a light grey pinstripe. Underneath the jacket I was wearing a medium blue turtleneck which complimented my eye color. As to shoes I picked a pair of black leather ones with a wider one and a half inch heel. I had done my preliminary packing before going to work and since my house was located on the way to the airport I would pick up my bags when I left to travel from work.
* * * * *
While at work I met up with Karen. We chatted about the holidays some. During our chat I mentally noted how beautiful she looked today in a very smart red pantsuit with black silk blouse. She had on 3 inch red leather heels which gave her a very statuesque look. We finished by going over some last minute items in preparation for the trip. As she had to drive near my house to go the airport a question was asked whether we should just take one car. I demurred as I told her I had to do some last minute shopping. She smiled and said that it was no problem and just an idea. With that we agreed to meet up at the airport. As I left her a fleeting image came to my mind of my most recent fantasy about her and it gave me a wonderful tingly feeling all over.
* * * * *
I left work at noon to do my shopping and then afterwards to grab my things at home and go to the airport for a 2:30PM flight. I went to the local mall and parked my car. Before leaving my car I ran the edge of my hand over my pants covered slit and felt a wave of pleasure sweep over me. I smiled at my naughty behavior and thought about late tonight online with Mistress. Hopefully my bedroom would be far enough away from Karen's so she would not hear me being up later. There was no reason to worry about getting up on time tomorrow as our meeting was not until 10AM and so I would push for a late breakfast. This would be my first ‘alone' time with Mistress and I was really looking forward to it. I did not give any more worry to Karen being in the same relative area as hotel rooms, even suites, were heavily sound insulated now. I broke out of my thoughts of the future and went into the mall walking with a very upbeat step.
After finding the Victoria Secrets store I went in to look at the negligees and thong panties. I passed by the area with garters but decided that the thigh high stockings would work just fine and make it easier for me to remove my panties when the time came. Besides Mistress would not be able to see me anyway so it really was just the idea of it all. I found a pack of very nice black lacey thongs that had a really small triangle in the front that were semi-sheer and made of a satin like fabric around the edges. I ran my fingers over the display model and I really liked the sexy feel and look of them. I picked them up to purchase. The next stop was at the nightwear display.
This was a much more difficult choice. I knew I wanted black but there were many styles. I decided first to just choose the styles that were possible and then to check on my size availability as this is where I always ran into problems. Even then once having found the right size I usually had to do a quick check in the dressing room to make sure it would look right on me as some made me look like a little girl in women's clothes due to my physique. I found three that I liked but one was not available in my size. I took the other two to the dressing room. One was a babydoll and the other a very sheer blousy type negligee that was held up by going around behind the neck. I took off my jacket and sweater and tried on the babydoll . Even though I had to imagine it without the white bra I had on I was not that thrilled with it. I then tried on the other one. The back of it was open down to the small of my back and it ended just at the bottom of my crotch. I though how sexy that might look when I removed the panties to play and that excited me. I now looked at the front and it was open to the bottom of my breastbone showing the middle of my chest. It was close enough fitting that my small breasts pushed it out some so it did not make me look too flat. I did like the way it showed the space between my breasts though and thought of being licked right there slowly by Mistress as she looked at me. That sent a wave of delight through me. It was very sheer but the folds of it somewhat obscured my breasts which made it every sexy. The panties were fully sheer and of a bikini cut but I would not be wearing them for long. I decided on this one.
After returning the babydoll to the rack I remembered about the choker. I decided to check if this store had what I needed and was rewarded with finding the exact item that Mistress described and so picked that up. I would have to go home and quickly cut and then re-sew the clasp in the rear as my neck was just too small for it even though it was their smallest. Happy that I found all that I needed I paid for it and left the store. As I was walking out of the mall I could feel a slight dampness between my legs and this made me blush slightly but I did enjoy it. What I would enjoy most of all though was being able to orgasm without being rushed and I knew I really needed and wanted that most of all.
* * * * *
As I drove home to finish packing for my trip my left hand rested between my legs and slowly rubbed up and down. I daydreamed about wearing my new clothes and this had the desired effect of making my menstruations more enjoyable. By the time I pulled up in front of my home my panties were bunched into my slit so that when I walked into the house the feeling was just heavenly. I thought about that for a moment and chuckled to myself for two weeks ago I would have been rearranging this ann oyance.
Once inside I got my partially packed bag and put some final toiletries inside. I placed my cocktail dress and jacket I would wear with it inside nicely folded as I only wanted to take one bag. I picked out two sets of shoes to take with both being black heels but one being my tallest pair. I had not decided whether I would wear that pair to dinner or not but I definitely had made up my mind to wear them late tonight. This brought a devious smile to my face. I looked through my black bras and picked the strapless one plus two others that looked nice. I then took one pair of black thigh highs, one of the black bras and one thong. I put everything else I needed for the trip inside the bag and closed it. I had only one more thing to do and that was to change my underclothes. I striped naked and again looked in the mirror to inspect myself. My left hand found its way to my slit and I decided to rub at least once. This extracted a moan from me and I closed my eyes to savor the feeling. I decided to stop otherwise I would want to cum right now as I was keeping myself on the edge. I put on the bra and thigh highs first. Now I took the thong and put that on. It felt funny running up the crevice between my cheeks but I could deal with that. I looked at myself again and I thought I would look desirable to Mistress if I ever did meet her. Right then I remembered about the choker so I had to open the bag to get it out. I decided to take out the heels for my late date tonight and put them on while I adjusted the size of the choker. After putting on the heels I went to retrieve my sewing basket.
Walking through the house in my sexy attire I felt so alive and wonderful. I tried to walk with a sexy sway and this had the effect of even making my nipples hard. I felt like such a slut! I got the sewing basket and sat down to my chore. I tried the chocker for size and then removed the clasp and cut it smaller. Making sure it was now an appropriate size I sewed the attachment mechanism back on. I decided to model it. I put it on and found a full length mirror. I was amazed at how sexy I looked and the overwhelming feeling of sexy submissiveness swept through my being. I so wished Mistress was here right now to see her bitch and fuck her. The power of that thought had the dual effect of making every part of my body yearn for sex while also making me turn a deeper shade of red. The feeling was so powerful that I had to take the choker off while kicking the shoes off. I knew that if I stayed dressed like that for even a minute longer I would have quickly found my dildo and got down on all fours and rammed it into me. I wanted her to use me so much that it is so hard to describe in words. I quickly put my work clothes from today back on with the new underclothes beneath. This had the effect of calming me down some but not too much. Hopefully I could calm myself further on the flight as I did have dinner tonight with the client and Karen. The last thing I needed to do was have my mind off business during this important dinner. I remembered that if everything went 100% according to plan we could walk away with a multi-million dollar deal. I checked to make sure I had everything and then left the house and drove to the airport.
* * * * *
After parking, checking in and then clearing security I saw Karen at the gate. She still looked breathtaking. She saw me and as I walked up to her she was smiling and almost it seemed, looking me over. I smiled in return and then felt self-conscious and looked down to regain my composure. When I looked back up everything seemed normal and we chatted. She had arranged that we would have seats together with our seats on the left side of the plane which had a two seat configuration. When it came time to board we both entered and she had me go first. I found our seats and put my bad in the overhead and sat next to the window. She stowed her bag and sat beside me.
After taking off we talked about the potential contract and other work items, including the latest gossip. She then talked about our dinner tonight with the client and let me know that there would three of them, all male. One would be the CFO who was in his early sixties while the other two were direct reports to him. Karen said they were all nice enough and the CFO would probably leer some but he was harmless. Her desire was that all the key business questions could be covered over dinner and the deal agreed to with the next day devoted to the details where that would be worked by his reports. She was so excited by the potential of the deal and us doing a little bit of the town that night that her left hand came to rest on top of my right laying on the armrest. She squeezed the back of my hand and I felt a rush of fear, discomfort and lust rapidly crest over me like waves of the ocean in that order. I had looked at her when she first did it and she was smiling, so hoping for success. However my glance grew furtive and I looked away feeling goosebumps all over my body. She said not to worry everything would go as pl ann ed and then she released my hand.
I thought I would feint when she let go like I was losing my air and could not breathe. It took a moment for me to regain my decorum although it seemed she did not notice at all. I could feel the thong inserted slightly into my slit and running along the space between both holes. Hot dampness radiated from my slit area.
The feeling passed in a moment and then we chatted for a bit more. Finally I decided to get a cat nap and feel asleep until we were on final approach.
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