This was to be my final time crossdressing, after many years of wearing womens clothes, I had decided that I would go out on top, with the finest of clothes and the best hotel.
I had been planning my trip for months, getting the wife to go away so I could stay at a fancy hotel I had my eye on, so I could wear all the expensive clothes I had bought for myself.
Back to the story, my wife had left on a girls weekend with her 5 closest friends, I had booked it and told her it was a valentines gift, she was so happy, but all I was thinking about was the wonderful weekend I had planned for myself, It took me months to save for all the clothes I had planned to wear while I was away, the sexiest lingerie, silk stockings, high heels, and a conservative business womans two piece skirt and jacket with a pale blue blouse, I had let my hair grow just long enough to be feminine but not long enough that she would suspect anything.
I had a small bag with makeup and brushes, hidden in the garage, ready to go.
As my wife and her friends drove to the airport in the limo I had rented for them, I knew they wouldnt return before I left, I started packing all my womens clothes in my small carry on bag and pulled on a pair of old jeans and a T shirt, I looked around the house for any tell tale signs of what I had planned, I was free and clear, as I locked the door behind me I a shiver ran down my back, this was to be the best weekend ever, for Charlee, that was the female name I had given myself.
I booked into the hotel, one of the fanciest and most expensive hotels I had ever stayed in as a male or a female, I got to the hotel door but the key wouldnt work, no panic this was a marathon, not a race, I would have lots of time to spend as Charlee, I went back down to the desk and the nice lady told me that the locks were new and they had been having some trouble with them, she played with the key machine and apologized and said “Have a nice day sir” I went back to the room and the door opened easily.
After I carefully unpacked all my clothes and hung them in the closet I sat on the bed and waited patiently for the time I would transform into the woman I would be for the weekend.
As I sat in the bath, full of scented bubbles, I shaved my arms and legs, it was so relaxing, I used a hair removal cream on my face to get the smooth look of a woman, I had removed my man clothes except for my grey T shirt, I always felt that men’s clothes were so boring and plain, and tucked them away where no one would find them, as far as anyone else was concerned I was Charlee, thats all they needed to know.
After the bath I dried my hair and curled it into a feminine style, I wished it had been longer but I didnt want my wife to get suspicious, Que Sera, I was very happy with how it turned out.
After I had finished my hair I started getting dressed, I applied the special glue to my expensive false boobs and applied them to my shaven chest, then I quickly laced my specially designed corset that I had tailor made to fit with the clothes to keep them in place, this gave me the hour glass figure that most women strive for, next were the stockings, Black and sheer, I attached them to the suspenders hanging from the corset, I loved the way they stretched when I walked, hmmmmm.
Anyway after I was fully dressed I curled up on the beautiful white couch to settle in for the night, a bottle of the best white wine the hotel had to offer, it was heaven.....
I picked up my phone to check if there was any messages from my wife and make sure there nothing had gone wrong with my plan, no messages, it was all falling into place, I rubbed my nylon encased legs as I had seen women do so many times.
The evening draws on.
I had done this kind of thing before but never found the courage to leave the room, that was all going to change tonight, what I thought would be my last night, I waited for the right time, late enough that I wouldnt have any contact with others, but early enough that I could have a little stroll then go back to my room and watch a girlie movie
(Not that I couldnt talk to other people, my girl voice was very good)
I put my jacket on that matched my figure hugging skirt, picked up my coach bag that I was planning on giving to my wife for her next birthday, and I decided to wear my 4” heel as I didnt plan on walking too far, I had perfected walking in a 3” heel many years ago, a 4” heel was a stretch, but what the hell this was going to be my finale, I picked up the door key card and headed towards the door.
I dont think I realized just what an enormous thing I was undertaking, I was about to enter society as a full blown woman, but too excited to think it through, I opened the door, took a quick peek to see if I could see anyone in the corridor, it was clear, I picked up my coach purse with lipstick, mascara and key card, I took my first step, checked to see if I had my key and allowed the door to close, “Click”
I walked towards the elevator where the ice machine was, which I had planned would be my turn around spot, and walked right past, as I went further down the corridor I saw an older lady coming from her room, I felt confident enough to say
“Good evening” and she replied “Thank you”
I was flying, half a bottle of wine in me, “I was Invincible”, “ I was woman”
When I got to the other end of my corridor I turned and began my triumphant walk back to my room, again passing the lady again, “Have a nice night” she said, to which I said “You too”
I got back to my room and felt amazing and wondered if I would go out again. As I took off my shoes and curled up on the couch to watch my girlie movie as I had done so many times in the past, I poured another glass of the wine and relaxed.
I was so excited after my very first walk ever I was too hyped up to let this moment pass, I quickly threw on my shoes and jacket and headed for the door, where would I go this time? maybe down to the lobby, It was risky but I knew it would be worth it, I might have to interact with more people but I had passed my test with flying colours with the old lady, as the door clicked shut behind me I didnt even look back.
I got into the elevator with two young men, they were busy chatting to each other, Im not sure they even noticed me, the door opened at the lobby and they allowed me to exit first, I nodded my thanks and moved to the middle of the reception area, then I got the scare of my life, “Over here honey” I turned fearing the worst, it was the old lady, beckoning me over, I still felt mildly confident, so I sat facing her, I was almost wetting my panties, she asked me if I wanted a drink and I told her “I would have a white wine please”, the conversation went well, so I had another two wines, but then she asked, “Are you having trouble with your key as well?” I told her I had had trouble with it when I arrived but nothing since then, she told me I should go back to my room and check it again, because they are moving people to another hotel until they can fix the problem, I tried to make a fast exit without looking panicky, as I walked to my room I could feel the wine taking effect, I hadnt planned on drinking so much, I had forgotten about the half bottle I had drank earlier on. I reached into my purse and pulled out the key, I nervously held it to the door, all I saw was a red light flashing, I tried again but only got the red light.
I was locked out......