After some careful planning and serious consideration I had made the decision that I would use my parent's birthday present to me to travel to Orlando, FL. They have a University there and tons of other things to see. For a kid from a little town in NC it felt like the biggest city that I could visit and still be safe (they have the house of mouse what's the worst that could happen). It was settled and within a few hours of talking it over with my parents they had purchased my plane ticket, gotten me a room at a hotel near a convention center (because, you know, cheaper than most other places) and had set up a campus tour for me. Being from a little place you kind of have a warped sense of distance between places. It turns out the University and the hotel were nowhere near each other. So yeah I never made it to the campus.
I had busied myself for several weeks leading up to the trip. I had decided that I would spend my whole trip wearing panties in public and every chance I got. I had started to wear them more often and had gotten to the point that I could pretty well control the erections. I had worried for some reason that when I got to the airport they would ask to inspect my suitcase and I would be outed. So I had taken special consideration on putting my collection of panties into tube socks, folding them together and stuffing them in my shoes. I had taken my contraband dress and placed it in the leg of my dress pants and folded those too. As the time drew nearer to my trip I was a bundle of mixed emotions. Should I be doing this, could I actually do this, even better would I actually do this?
On the day of my flight I decided that if I was going to actually do it I was going to have to start right then and there. I dug into my suitcase and withdrew a sock ball from my shoe reached into a sock and pulled out a cute little yellow cotton brief. I slipped them on and slid my shorts on. They were so soft and light and rode just slightly up my pert ass. As I rode the hour and a half to the airport my folks droned on about staying safe and checking in regularly. About how proud they were that I was growing up so fast and to not feel pressured to go to school so far from home. My mom at least ten times reminded me that her and my father met at a community college forever ago.
After what seemed like forever I finally boarded the plane to sunny Florida. On my short flight down I chatted up the business man next to me. It turned out that my folks had gotten the hotel they got because there was a convention at the same hotel and a couple of the big companies scheduled to attend had backed out. According to my new friend there was a sleepy little bar in the hotel but the real action was out and about near the convention center. He was also nice enough to offer to split a cab with me to the hotel. He was a father of three who traveled all over for business, but he loved Florida and always looked forward to "blowing off some steam"! I knew what that meant and no doubt he "blew off steam" everywhere he visited. He was a mid forties business man who's best days had probably already passed him by. All I could think was how bad I hoped that I would not have to spend my life traveling to "blow off steam", but at the same time here I was traveling somewhere to be free of the community I lived in. We bonded over playing high school sports and I could see that he had probably once been very athletic, but comped dinners and breakfast buffet's had put some extra weight on his 5'9" frame.
The cab ride took what felt like forever, again spatial awareness I guess. But as we pulled up to the hotel I was amazed by the amount of activity occurring all over. This was the place that you could get lost and blend into if you wanted to. I handed my new friend some money for my half of the ride and we grabbed our bags from the driver. In the lobby the level of busy did not subside in the slightest, as I waited in line to check in the area was awash in business men and women as far as the eye could see. The hum of conversation was incredible. I got my room card and shuffled off through the crowd. I was on the eleventh floor and shared an elevator with a group of very tan gentlemen that were speaking a level of Spanish above the two years I got in high school. I disembarked the elevator and found my room, as the door closed behind me I placed the safety bar for extra security and stripped down to my panties. I walked to the window of my room and peeked through the shades, outside was a plethora of opportunity and activities. I could see a Walgreens and several other shops, I waned to go shopping. I jumped in the shower and cleaned the flight off of me, toweled off and slid into a fun little gray lace thong, some shorts, a bra and a heavy tee. I trotted down the hallway to catch the elevator and within a few minutes I was out on the busy street in the heavy Florida heat. The thong seemed like the best idea I had ever had.
My first stop was the Walgreens, which though new and brightly lit, had very few customers. I quickly dashed to the cosmetic aisle and began picking up the necessities (lip liner, mascara, etc.) then I made my way to an aisle that had women's hosiery and to my wonderment I found bra lifts (inserts to make it look like I had breasts). I was in heaven, I was buying things for myself in a place where no one knew I existed. I scurried to the counter to pay and without even a sideways glance from the cashier I was out of the store with my bounty. Next I hit up a Payless shoes about three stores down and with little trouble had found a pair of black heals women's size 12 that fit my feet. Another quick cash transaction and I was headed back to the hotel. On my stroll back I passed a tourist trap shop that caught my eye, all the manakins in the window had different colored wigs on. I popped in and to my amazement found an aisle of costumes with a dearth of wigs to choose from. Being a natural blond with blue eyes I decided on a jet black wig. I thought why not match my dress and set off my eyes. At this point I was so thrilled with what I had acquired and almost skipped back to the hotel.
In a matter of 45 minutes I had found all of my goodies within one square mile, Orlando really was a magical place. As I walked back into the lobby I became painfully aware that I had only eaten some airplane pretzels and a cookie all day. I walked into the "sleepy little bar" my business man friend had told me about. He was completely right about the place, with all the bustle around it, this little bar was inhabited by three patrons and two wait staff. I sat down at a booth and looked over the menu, settling on a burger and some fries I flagged down a waiter and placed the order. The food was nothing to write home about but in my hunger state I wolfed it down and headed up to my room.
Once the door closed behind me and I had locked the lock I was a light with giddy. I spread out all of my goodies on the bed and began unpacking my bag. I stripped down to my bra and panties. I slid on the hose I had just bought and slid the bra lifts in. I slid my dress on and went to work applying my make-up. I fitted my wig and straighten the hair the best I could, then sliding on the heels I began to walk to the bathroom to take a good look at myself. Unfortunately walking in heals is not a natural thing and I toppled quickly, bouncing off the corner of the bed. I abandoned the shoes and walked into the bathroom. I was amazed at the woman that stared back at me from the mirror, sure my make-up game needed more work but for all intents and purposes I was a passable woman. I gave the heels another try just to see what the finished product could look like. Standing still in heels was still a task and unfortunately made me 6'5" which to me seemed less passable then I had been before. So heels were out, but in that moment I was probably the happiest with myself I had ever been and in my triumph I walked to the window of my room and threw open the curtains. For anyone interested in looking, there I was, proud as a peacock. I took it all off and made a few notes on some makeup changes, slipped into a pair of Lycra boy shorts and crawled into bed for the night.
The next morning I woke with a massive case of morning wood. I stoked myself to climax in my panties, cleaned up, slid on a basic black bikini cut, some shorts, a tee and headed down to continental breakfast. The place was abuzz with activity and the breakfast area was packed with the business crowd, all dressed to impress and ready for their days. While I ate my Belgian waffle I was taken aback by some of the gentlemen in the group. They had on fitted dress shirts and suit coats that were tailored to there form. Before I could realize I was doing it I had been caught staring at a handsome 30ish business man in a grey suit with a lights blue dress shirt and peach colored tie. He was probably my height with light brown hair. What had caught my attention was the form fitted pants that made his muscular buttocks look amazing and they were tight enough that the outline of his flaccid penis was slightly visible. He didn't see me staring but I became quickly aware that the gentleman he was talking to was looking right at me. I quickly busied myself with something on the table and when I looked back up the man in the grey suit was looking at me. OMG he had beautiful green eyes, I freaked, turned flush red and scrambled back to my hotel room. Once back in my safe place my embarrassment was brought to bare by the fact that I again had a raging hard on and had probably run from the lobby with said boner. What was happening to me? Aside from the confusing moments with Nate I had never ever looked at a man that way.
