I have been dressing for about 15 years. It has been a wonderful experience and I still enjoy the feel of the nylons and the way my legs in high heels. I always wear heels of at least 4 inches and even wear nylons under my awful male clothing everyday. While my life is now exciting and enjoyable my mind still wonders to the excitement of the early days of dressing. I have shared my experiences with others in person and in chat rooms.
I have recently felt an urge to share with even more people the wonders and joy I felt during my first few times out dressed. This is my first installment.
Chapter 1
As a young boy I had enjoyed many times the feel of silk and nylon as I would dress in my mother's sexy undies and nylons when she was gone. I would rush to her room as soon as she would leave for work or run an errand. This was the extent of my dressing until I graduated high school and started living on my own. The dressing progressed and I would spend hours at home perfecting my makeup and my walk. I simply adored garters and heels loved to be slutty in my clothing choices. I did not, however, have the nerve to leave my home as I lived in a small town and never wanted to be seen. I tried a few excursions late at night and drove around some but never went where someone could see me.
That all changed one day when my job took me to another city for a sales call. I was excited for two weeks about the prospect of dressing and not having to change my gender for after only a few hours. I shopped for days looking for the right outfits to take with me. I even bought a new auburn wig and a couple of pairs of shoes. Both pairs had 4 inch heels. One pair was black with metallic spiked heels. The other pair was a royal blue snake skin. I packed early on Friday and left for the city. I would have the whole weekend to dress as I like and would explore the local gay bars during that time.
I arrived at the hotel around three and asked for a room with an outside entrance.
Immediately after arriving in my room I ran a tub of warm water and added some bubble bath with baby oil and soaked my hairy legs. After shaving them smooth I toweled off and proceeded to the bed. I pulled out my new all in one girdle. It was black and helped me to form a nice cleavage. I then slid on my black sheer stockings with the seam up the back and attached them to the garters that were hanging down from my corset. I almost came at the feeling it gave. Not wanting to wait I put on my 4 inch black heels I had purchased that week. I opened my suitcase and starting applying the make-up. Trying very hard to look like a slut. Then I slid on my new full auburn wig and looked at myself in the mirror. I was hot! If I do say so myself. I am 5'8" and weighed only about 125 pounds. My legs were excellent as worked on my calf muscles.
After strutting in the mirror for a few moments I returned to my bag. I pulled out my 8 inch dildo I had so much fun with and started sucking it in my lips as I watched in the mirror. Then after lubing my "pussy" I slid the length up my hot hole and pulled my panties back over my ass.
I then decided on some red nails. I love the way my hands look with long painted nails. I chose a medium length red nails which I glued on. I could not resist taking my nails and rubbing them over my smooth, nylon covered thighs. Mmmmmmmmmm. I came almost immediately had to clean myself. I loved the way it tasted as licked it from my fingers. Feeling refreshed I continued my dressing.
I pulled my short black skirt from the bag. Sliding it up my long legs is always a turn on for me. After zipping the side zipper up I reached for my top. It was a long-sleeved white sweater that showed of my cleavage well. I looked in the mirror and strutted some more. It was now getting dark outside and I decided that I would be safe to leave the hotel now. I had picked out a bar on the north south side of town that had advertised drag shows. I was hoping to be accepted in that environment.
I hesitated as I gathered my purse and headed for the door. I was so scared to go outside. Finally I took a deep breath and headed out the door. The cool air felt good as my heels clicked along the pavement. I was startled as a young man walked around and I avoided eye contact as reached for the car door. I quickly started my ca and headed for the interstate. I drove around the loop several times enjoying it when a trucker would honk at me as I passed as they could see my bare thighs showed above my short skirt and stockings. Feeling bolder I stopped at rest area and walked to the ladies room. I arrived back at my car and headed downtown to the drag bar. I circled the block looking for a parking space and could find none close. I had two blocks away! I looked in the mirror and fixed my lipstick before getting out. Once again the cool air felt good on my legs as I walked to the bar. A group of young men whistled at me I smiled back as "accidentally" dropped my purse and reached over for it. They stopped and I quickly walked away arriving at the front door of the bar. It was already crowded there and I went in. As I watched the people dance I looked around hoping I was sexy enough. I made eye contact with a well built black and he smiled back and then disappeared. I felt rejected and wondered if I was acceptable in my appearance. Then I felt someone pushing from behind and felt a huge hard cock pressing against my ass. I did not turn around immediately and just responded moving my ass from side to side. Then I turned to see that sexy black man standing there. Without saying a word I kissed him deep as his hands covered my ass. So fucking hot. He asked me to leave with him which I did.
He held my hand as we walked to his car. I immediately went for his cock as we settled in the car. Damn, it was huge. My long nails traced up and down the length as my tongue licked the nectar from the tip. Oh shit. My mouth was spread wide as he entered slowly. I could not take it all but surprised that most of it fit. My hands would not even reach around it. I sucked like a whore as he pinched my nipples and moaned in delight. Then he pulled my mouth away and begged to fuck me. I knew that there was no way told him politely that his cock scared me and said I wanted to taste his cum. I went back to sucking he exploded quickly and started gagging as the cum filled my mouth and I tried to swallow it all. I took what spilled out and brought it to my mouth and exploded in my own panties as licked my fingers clean. He walked me to my car and gave me his number which I used later. He drove off, but I headed back to the bar for more fun.
End of Part 1.