It was cool spring in my 25th year and I had grown very fond of the feminizing and cross-dressing experiences. I was between girlfriends and so was completely free to indulge my deepest sexual fantasies. It was at this point in my life that I decided to enjoy a completely sensual and sexual couple of days travelling by car across New Jersey and New York. At this time my already attractive youthful italian looks were complimented by a completely slender 155 lb firm hairless body. I had sensuously discovered the power of Nair one evening while showering! Wash away unwanted hair! Imagine that.. well anyway, that was just the start of my lovely and delicate transformation for my horny escapade.
I had spent some time shopping online and in some lingerie stores and here's what I had decided upon for my slutty outfit. It really wasn't terribly difficult for me to choose what I would be wearing as long as it was tight and smooth in all the right places. ! I would always start with the basics and for me that would include a perfect pair of pantyhose. Pantyhose have always been one of the most sensual parts of my feminine wardrobe leading to many other soft and lacey choices to add later. Today I had chosen a pair of sheer jet black silky hose to wear. They would match perfectly with the 6" juliet heels I had recently bought online. And just looking at those shoes was enough to bring me close to orgasm... but that's another adventure altogether. The rest of my outfit consisted of a tight black mini skirt, tight little shiny black panties, tight waist-cincher, silky red lacey 34c bra, very tight lime green short sleeve stretch t-shirt and my reddish brown gidget cut wig. Makeup consisted of red lipstick for my full round lips and light foundation. I didn't want my makeup to appear fake... so I would always apply just enough to look natural, but not heavily madeup. My face was already very pretty so once I was wearing my wig, it was possible for me to pass as a woman...
My destination was upstate New York and I began my trip in New Jersey. Not wanting my neighbors in the city to see me leave my place fully dressed, and also enjoying the thrill of removing my "normal" clothes and dressing in my "sensual" clothes was very arousing for me. So it was that I stopped in a large parking lot in a shopping center and parked a good distance away from most of the cars. It was there that I removed my pants, underwear, socks, shoes replaced very slowly and sensuously by pantyhose, panties, cincher, and bra ( the lovely waterballoon full form breasts would be added later). These were the basics that I was really in a hurry to be wearing. I then put my pants back on leaving my bare pantyhose feet to manipulate the car pedals. After this I got back on the highway, knowing that there was a rest area not too far from here which might offer the opportunity for my first encounter of the day.
After about 20 minutes I saw the signs for the first rest area just outside NYC. The sign said open from dawn to dusk... so it being daytime, I knew it was ok to stop. I took the winding exit which led to a parking lot overlooking a wonderful view. I parked about 10 spaces away from a van that was parked already. I wanted to finish dressing here so I would need to put my seat down and lay back in order to do so. First I lay back and removed my shirt replacing it with the tight green-t just below the sight-line of the nearest vehicle. As I stealthily found my red breast forms in my bag, I eased them under my tight shirt and into place. They very nicely filled out my red bra under the tight green t and my femine form had now decisively appeared. I then removed my pants to reveal my very smooth, long and sexy legs encased in black sheer nylon pantyhose. It was easy to pull my very tight short black mini up my legs and into place as I made sure to avoid rubbing my erect boy pussy against the steering wheel. After this I tenderly put my 6" juliet heels on. Now that I was totally dressed, I was completely flushed with horniness. I felt a growing warmth between my legs which soon spread to possess my entire body. The erotic feeling of my hair resting on my shoulders, round full breasts stretching my tight green t, they gentle caress of cool air on my bare pantyhose legs and the slight pinch of my high heels gradually caused me to move and quiver in very feminine convulsions of pleasure. I licked my lips and and gazed seductively around me.
I was still in the parking lot when I noticed another car pull in to my left. Since I didn't want to attract immediate attention - this could have been law enforcement- I backed up my car and proceeded to the end of the parking lot parking with the drivers side door facing the sidewalk. It has always been erotic to feel the cool air on my sexy legs, feet and thighs... and I could barely resist opening the door to my car to get out and wander onto a little trail l could see at the bottom of a short hill leading into a wooded area. I opened my car door and felt the cool air on my legs and a feeling of true abandon came over me. I felt totally feminine in my tight skirt, heels and pantyhose. Soon I was out of my car and delicately making my way down the moistened ground. Thankfully someone had thought to put some small stones there that prevented my from sinking in and tripping. I quickly made my way to the wooded area and gently rubbed my boy pussy there in a secluded area... I couldn't resist any longer, however I would not make myself cum yet! After enjoying the seclusion I got a bit chilly and made my way back to my car.
No sooner did I close my car door when I noticed an older gentleman walking toward my car. I believe he must have been watching me from his car which had just pulled in to the parking lot and was parked about two spaces away in the opposite direction. I could see in my rear view mirror that he had his eyes on me. He clearly didn't seem to be in a hurry and he slowly approached my open window with his moving hand in his pocket and looked in. He smiled and looked at my face, chest and sexy legs then he said, "Wow, how are you today? Don't you look just lovely?" I of course said hello and thank you etc. He then proceeded to say how pleased he was that I was there- all the while moving his hand in his pocket more vigoruously -He said that this was primarily a gay hang out and very few hot looking CD's came by there but that he was very nicely surprised to see me there that day. He then invited my to get out of my car, which I did. I stood up against my car in the cool daytime air, but out of sight of the rest of parking lot in case someone should pull in. He then asked if he could touch me and I said please do sir. After I said this he asked me what I liked and I said that I liked pleasurable things and that if he'd like to offer me some pleasure that I'd gladly oblige him. He really enjoyed my submissive attitude and began to more aggressively touch and feel my sexy legs and thighs. His touch was electifying as he teased my legs with light caresses and then firm massages reaching back to my firm ass. He was now brazenly fondling me under my skirt in broad daylight.
Slowly he made his way up and under my tiny black skirt and began to caress my hard boy pussy. He said that he liked it very much and that I was certainly one of the hottest dressers he'd ever seen. While he was fondling my boy pussy he asked if I would be willing to meet him again soon and of course being in the heat of passion, I agreed to it. At this point I could feel the cool breeze directly on my now exposed pleasure spot and I could not hold back any longer. He was gently probing my rear hole and massaging my boy pussy to the point where I was melting with pleasure and soon I was exploding into his loving hands with wild abandon. Purring and almost screaming .... it was amazing!! He told me he'd like a chance to make me cum again orally and to penetrate my button, but not here in public. He was afraid to get caught.
After the smoke cleared from that first encounter, I gave him a kiss and said thanks for all the pleasure and good day He passed me his phone number which I never did get a chance to call again.... It was simple to cleanup since I didn't cum on myself... rahter in his hand. Then I was back in my car in a jiffy to fix my makeup and hair and on to the next adventure... as Julie Hourglass!!