Weekend Challenge Ch. 01

Just a few weeks after the auction with Jenna I began thinking that it was time to push myself some more. Try and fulfill another of my fantasies, challenge myself and see if I could follow through. I would need Ed for sure if I wanted to really and truly go beyond anything I have done so far. I called Ed and suggested he come by one evening for dinner. I thought it might be difficult to really discuss what was on my mind in a crowded restaurant. The night Ed came over we had a nice simple dinner, I am not helpless in the kitchen but my culinary skills are limited. We enjoyed a nice dinner of Chicken Marsala and some wine. During dinner we talked about Jenna and the night of the auction, and our shopping adventure the next day ( To be posted in the not too distant future). I began telling Ed how I felt I had progressed and had fulfilled a number of my fantasies and that he played a big part in them all.

Now Ed knows about many of my fantasies as we have discussed them from time to time. He is well aware that they are not all able to become reality. At least not without me ending up behind bars for public indecency. Someday I will have to write about my most outrageous and probably unrealistic fantasies. Now Ed and probably all those who have been following my adventures know that the greater the distance between me and any clothing the better. I told Ed that I wanted him to create a challenge for me. Now I really will not know the full extent of this challenge I am only setting a few of the stipulations for it. I told Ed that I wanted to go somewhere that was at least a four or five- hour drive and that we should fly there and rent a car to drive back.

I also told Ed that he was the one that would pack for me. This way other than the clothes I had to wear on the plane I would have no idea what else I would have to wear at our destination. We decided that we would leave on a Friday, stay two nights and drive back on Sunday. I had bought lots of great clothes that were great for flashing and for showing some or a lot of skin when Jenna and I went shopping. We made plans to leave the following Friday on a mid morning flight from Newark-Liberty airport. The day before we were leaving Ed came over and while I went to get a manicure, pedicure and waxed he packed my bag for me.

Thursday evening I had that nervous feeling in my stomach knowing that there was an adventure on the horizon and that I had little or no control over what would happen the next few days. After a little pleasure with my overworked pocket rocket and a bubble bath I went to bed. I began wondering what had Ed packed, and thought about peeking in the bag but I didn't. I did start thinking about my outfit for the plane and then drifted off to sleep. The next morning after my shower I stayed naked while I had some breakfast and coffee. I knew Ed would be picking me up about 10 am to go to the airport.

Shortly after 9:30 I went in to get ready. It really doesn't take long for me to get dressed. I had picked out a cute little sundress that has buttons all the way down the front. It is a pale yellow with flowers and has a scoop neck that shows a nice bit of cleavage. It is a very light, wispy material that flounces as I walk. It's not overly sheer but I am sure that it is quite a site if I am in the sun or standing in front of lights. I decided to forgo the bra and knew that my nipples would be poking through my dress but they should not be blatantly visible. I went to the drawer and looked for a suitable thong or g string and after trying on a few and looking at myself in the mirror with the dress on I lifted the dress and pulled the thong off. I decided I would just wear the dress and a pair of sandals for the flight. The dress was short it was maybe 12 inches from hip to hem. I would need to watch when I sat or bent over but I felt it was sexy but not unacceptable for the airport.

I was dressed , Ed had left my overnight bag near the front door so I just waited for him to arrive. I went to check my face and all one more time and then the doorbell rang and he was there. I went to get my little purse and Ed took my overnight bag out to his car and we were on our way. He asked if I had any second thoughts about this and I said I was nervous but ready to go through with it. He asked me one more time and said that once I agree again that he will be in control for the balance of the trip. He had packed my clothes and he would determine what I would wear and what we would do. I trust him completely and know that I would be safe so I told him let's get going..

The traffic was not terribly bad, we parked and took the monorail to the terminal. The monorail was pretty empty but the few men that were on it looked me up and down a few times. The monorail arrived at the terminal and we took the elevator up to the gate level. The terminal was quite busy and I was enjoying all the attention I was getting from the many businessmen as we walked through the terminal to the security checkpoint before entering the gate area. The line for the security check was somewhat long as is usual for the New York area airports anymore. I did a bit of fantasizing as I usually do while waiting for my turn to pass through the metal detector. Seeing myself taking off my sandals and the only piece of clothing I am wearing to prove I am not hiding anything.

I see myself standing there in the middle of Newark-Liberty airport stark naked. Obviously a fantasy that will remain a fantasy, I think. Anyway we passed through security with no problem and waited to board our flight to Virginia Beach. I like it there, it has a lot of hotels along the ocean with lots of beach areas and there are some fun nightclubs and bars in the area. The flight was short and soon we were on our way through the terminal to get a rental car. My dress was drawing more attention than I expected, I asked Ed if he had also noticed the looks I was getting. He said "of course your getting looks, with the bright sunlight your silhouette is clear as day through your dress". I hadn't realized that it would be that transparent. Well nothing I could do about it and I really wasn't showing anything indecent that I would need to worry about security.

The agent at the rental car desk was trying so hard to check out my nipples pushing out the front of my dress without me noticing. I of course knew right off what he was looking at but I pretended not to notice. We rented a nice convertible and took the drive to our hotel, which was one of the better hotels right on the ocean. We checked in and took the elevator to the top floor to go to our room. We had asked if there were many kids in the hotel and were told there were some but mostly on the lower floors closer to the pool area. So Ed requested a room on the top floor to try and avoid any run ins with kids.

Once in the room I wanted to open my overnight bag to see what Ed had packed but he said that he would tell me when I could open it. It was too early for dinner so Ed called down to have a some wine and other beverages brought to the room. he said it would be about 15 minutes and then he told me to take off my dress and get comfortable. I unbuttoned the dress, took it off and hung it in the closet. Once naked Ed told me we would need ice and that he saw the sign for the ice machine down the hall. I was sure that ice would be brought up with the beverages but I made the obligatory walk naked to the ice machine. I am not sure but I think a gentleman got a glimpse of my naked ass as I was just walking back into our room. Just a few minutes later there was a knock at the door and a male voice called out "room service" I went to go into the bathroom but Ed handed me a few dollars and asked me to get the door.

I just love the glassy eyed look of a young college man as he comes face to face with a naked female. He looked nervous but was sure taking inventory of my body from head to toe. He came in and set the tray with the drinks and ice on the table. He tried to get a few words out but had some trouble. I thanked him, gave him the tip and opened the door to let him out. I had opened the door all the way and as I stood there a man and woman were walking by and saw me standing there naked. I could see the smile on the man's face. The waiter walked out into the hall and I closed the door. We had a drink and I went in to take a shower.

When I came out I noticed that my dress was no longer hanging in the closet. I asked Ed about it and he said that everything I would need was in my overnight bag. It was time to see what was in my bag. I needed to freshen up my drink before I looked. I was so nervous but yet so excited from the anticipation of what I would find. I grabbed the bag and felt on light it was and wondered if there was anything in it at all. I slowly opened it up and the first thing I noticed was that there were clothes inside but not many. I began taking everything out one piece at a time. The first thing was a man's white button down shirt and I wondered what I would wear with it. Next I saw what looked like a skirt folded up and when I took it out it was a skirt. A skirt for maybe a twelve year old girl! I held it up in front of me and saw that if I wore it very low on my hips it would be maybe three inches below my pussy, four if I was really lucky. It was just a pull on skirt no buttons but it would be a challenge to wear it and stay decent.

The next was what first appeared to be a conventional halter top but I soon found out it was a split front halter. It was really two pieces of cloth held together by one thin strap that went around the back of the neck and it had a length of ribbon that went around the back of the top and would be tied just below my breasts. This made it totally backless and only the tiny ribbon would keep it closed in front. I put the halter aside and saw there was a very small bathing suit in the bag. It was a very pretty pale yellow, the top was very small and thin. I was sure that when I wore it there would be lots of cleavage and the bottoms of my breasts would be at least partially exposed. The bottom was a very small triangle of cloth connected by a very thin string for the waist and a thin strip of cloth which really wouldn't cover anything in back.

There was another small skirt but not as small as the first. It also had no buttons or anything but it was split up both sides all the way up to about two inches below the waist. I found one more top that was more like what I typically wear. It was a scoop neck and cropped short with buttons down the front. This was all that was in the bag except for a pair of sandals with about three- inch heels. There was no bra or panties of any kind. I looked at everything laid out on the bed. One nearly non-existent bathing suit, a man's button down white shirt, a split halter top, a skirt for a little girl, one crop top and one more mini skirt with slits all the way up both sides and the sandals. This was going to be one challenging weekend.

To be continued

Love to all

Nikki