Highway in Heels

*Stories from the real world 1

This story is slightly autobiographical.

When I was 20 years old I used to drive a van for my parents from Brooklyn to Tarrytown New York once a week to drop off merchandise for retail shops in the area. I always had a full van on the way up, but on the way down the van was almost empty. It was the summer of 1985 and I was given twenty five to forty dollars, plus gas to make the drive. I did this for the entire summer while I was home from college.

I was a crossdresser for 11 years at this point and I was very good at it. Even when I wasn't dressed as a girl, some people were confused, I always had long hair and sometimes put it in a ponytail. I lived in the basement of my parents' home and I had plenty of privacy. I was ususally the only one home and the house was often empty. My father had a huge warehouse filled with random things and when anything that captured my feminine outlook and was in stock I made sure that I had access to it. My wardrobe at this time was pretty big and I had so many dresses and skirts and blouses that I had hardly any room for them. I used to keep some of my clothes and various pieces of lingerie in a box in my van.

I remember once we got a huge shipment of Candies. They were perfect sexy heels for younger women. I had 14 different pairs and I wore them all out, they were so sexy. I also had dozens of sunglasses, fishnet stockings, leg warmers and tube tops. Well it was the 80's.

When I had nothing to do the rest of the day after a trip to Tarrytown I would go in back of the van and get dressed up and make the drive back dressed as a woman. It was by far my favorite thing to do, and I did it a lot. I had about an hour drive and I loved teasing the truckers that drove next to me on the highways. I wore my Candies and I would flash the truckers my nylon legs and even my panties. Then when I got nearer to my home I would park and take all my female items off. My block when I was a kid was so busy I couldn't chance anyone seeing me dressed as a girl.

***

One of the most exciting things that has ever happened to me, happened that summer. My parents bought a summer house in Connecticut. They asked me to pick up a wall unit in New York City and drop it off at their Connecticut home. The drive was about 2 hours. I also took some of my girl clothes with me for the ride home. I have been dressing so much that by the time I was 20 I had no trouble at all looking like a girl, though I never really went out much, and I never interacted with anyone. The times I have tried to go out en femme, I always felt everyone was looking at me. Being in the van seemed like an easier issue.

Once out of CT and on the way home I stopped at a rest stop and went in the back of the van to get dressed. I had a nice couch in the back and a cooler that I used as a makeup table. The back of the van looked like a small apartment. I even had curtains on the windows and paneling on the walls. I got completely undressed and slipped on a pair of white satin bikini panties, but not until I tucked myself in to give me that perfect female outline. I have been doing this since I was young and was able to walk around completely bottomless, with just one little strip of surgical tape, and no one would ever guess that I had anything less than a perfect little pussy. Next I slipped on a pair of Leggs Nude Sheer Elegance pantyhose. They were so sheer and gorgeous. I had so little hair on my legs, and the ones that I did were so light you could never see it through my stockings. My arms were also very light.

I next put on a bandeau bra, I stole it from my sister, who was a dancer. She would wear it when she wore a leotard. It had no shoulder straps and I put it around my chest. I then slipped in Balloons filled with water into the bandeau bra. I always used two balloons, one inside of the other for extra protection. I hated when they leaked and my top would get wet. I wish they had breast forms when I was young, the freedom I feel wearing those is incredible. Next I put on my peasant top. It was light brown and it was shoulder less. It fit perfect on top of my strapless bra. It also had sleeves which were sheer lace with polka dots. It felt so feminine that I wore it all the time, though it did look a little too fancy for the highway.

I then positioned myself in front of my little mirror to work on my makeup. I didn't really use a lot, I already had some feminine features. I always wore false eyelashes though, and I had to fill my bottom lashes with mascara. Being blonde my lashes were so light, and also my eyebrows, I always had to fill them in with a brown pencil. I put on blue eyeshadow, because that was popular back then, and a slight bit of rouge on my cheeks. I then outlined my lips with a dark red lip pencil and filled them in with a little lighter red lipstick. My lips always looked full and sexy. This was my basic look and I always looked feminine. I then took my hair out of the pony tail and fluffed it up a little using my fingers and some spray. It came down a couple of inches past my shoulders and was a reddish blonde mix. Sometimes I would put a scarf around it to give me more body.

Next came my white peasant skirt with red flowers on it. It came down to my ankles, but had a slit up the front almost reaching my panties. The skirt was perfect for flashing other drivers. Then I would put on my 4 inch leather sandals, my big white clip on earrings and a bunch of bangle bracelets on my left arm. I was now ready to hit the road as a woman.

I loved the first look in the rear view mirror at the cute girl staring back at me. Fixing the seat belt around my breasts, and adjusting my skirt. I then tried to make eye contact with people in the parking lot to help my confidence. Sometimes I would put my hands behind my back and stretch. My breasts always look huge when I did that. Sometimes I got honked at before I even left my spot.

Once I was on the road I was in all my glory. I felt the wind in my hair and my breast bounce when I went over any bumps. Since I was in the van only trucks were able to see in my window, usually the cars were too low. I would sidle up next to a truck on their right side and slowly start bringing up my skirt. I would hang around the driver's window for a while. When the truck would stay next to me, I knew they were watching. Usually once I showed my panties the trucker would honk, and then I would take off ready to flash the next one. A number of times I would lean over and wave if I found them cute. I would drive next to a number of trucks and flash most of them. As long as they were paying attention they got an eyeful of my glistening legs and silky panties. The crazy thing is that it made me so excited, I loved showing off to these men.

I remember I was next to a truck driven by an older man who waved to me with his hat. I always imagined they were talking about the hot blonde in the blue van with incredible legs on their CB's. I slowed down and hovered next to him, slowly once again showing off my legs and panties. I would run my fingers up and down my thigh as I drove, inching closer to my panties. Once he honked his appreciation I just sped up ahead looking for my next flirting victim.

It was then I heard a bang, shit my tire popped. The van started to veer left, and I had to get off the highway. I was in the middle lane and slowly made my way to an on ramp of a weigh station. I didn't get too far off the highway. I pulled over to the side cursing that I was going to have to change clothes before I fixed a flat tire. I was so worked up flirting with the men that I had to rest on my couch for a bit. Just as I was about to change there was a knock on the back window. And then I saw a man sidle up to the open passenger side window.

"Hi, Miss. Are you okay?" To say I was startled is so misleading, I was suddenly frightened. I could barely talk.

"Yes." I said in my female voice I have been practicing forever. Never planning on actually using it. "Do you need some help?" I heard him ask. It was then that I knew I had to get out.

I took a deep breath, did a quick check in my mirror and opened the sliding side door. He stood right in front of it with a huge smile on his face. It was the trucker with the hat, the older man that I just left. "I see you have a flat, baby girl, come on let me help you with it." He had a slight southern accent and he was tall. He then grabbed my hand and helped me out of the van. He watched my legs and heels as I made it out. He then made me stand on the side of the road, in view of all the truckers at the weigh station, while he fixed the van. The slight wind of the trucks passing by would make my skirt fly around my legs, and I was getting embarrassed whenever any of the truckers would beep or say hello to me while I waited. He was almost done and two other men came over to offer some more help. I was so out of my league, but I was strangely excited. Another five minutes and the three of them were done.

"There ya go Miss." He said while he wiped his hands on a rag. I thanked the other two men and they left leaving me with my initial trucker. "Hi, I'm Branson." and he reached out for my hand with his, and then held it up when he noticed it still had some grease on it. I noticed he had a wedding ring.

"Hi." I said for the first time ever as a girl. "I'm Donna." He smiled.

"Hi, Donna glad I was right behind you when you pulled over. I'm so happy to see a pretty girl up close. Are you okay, can I do anything else for you?" He smiled again and I felt very content, he was thinking I was a real woman and I was liking it very much. I went to the van to get my wallet. I was wishing that I had a pocketbook, to find some money to give him. "Don't be silly. Hey why don't you buy me a cup of coffee at the next rest area? That will be sufficient enough." He smiled again and I said yes. "Follow me." He then jumped in his truck, pulled around me and I followed.

I was thinking that once he pulls into the rest area I will just keep going, but the closer I got, the more brave I became, and all of a sudden I was following him into the parking lot. I fixed my hair and put on a little more lipstick. He watched me as I fixed my lips. I even sprayed a little bit of perfume on my wrists that I had hidden in the glove compartment. I smiled at him and he helped me out of the van. "What's a pretty young thing like you driving this big van." I swallowed and told him it was my parents and I was driving it to Brooklyn for them.

We went in the diner and Branson headed to the mens room while I excused myself and went straight for the ladies. This I have done before, so I wasn't too nervous about it. I went to the sink and cleaned up a little, I didn't really know what I was doing or what was going to happen, but I was still a little excited and I wanted to see this through. This was literally the first time I was out as a girl with someone. Usually I would run into rest rooms and pray no one was paying attention to me.

When I came out of the ladies room I found the table and he stood up and helped me into the chair, he was being so polite and nice to me. I was simply loving it. I remember fixing my skirt as I sat at the chair and crossed my legs. I felt like I was overcompensating and being hyper-feminine, if that's a thing. He complimented me on my hair and perfume.

I was wishing I wore nail polish, so I kept my hands in my lap most of the time. "You know, when you came up next to me and slid up that dress, it made my whole day." He whispered. "I don't get to see too many fine legs while I drive, and there is nothing like seeing a pretty woman on the road." We ordered coffee and we talked, I noticed his wedding ring was gone and it felt strangely intriguing. He kept referring to me as baby girl, even to the waitress and I was loving it. We talked a little bit more and then he asked me if I wanted to see his truck. Back then, I didn't know why anyone would want to see a truck, so I declined and said I had to get home.

He wouldn't let me pay and then he took my hand as we made our way back to my van. "Thank you again." I said. "It was a very nice afternoon. I'm glad we met."

He smiled again and said. "Why don't we just stay and talk in your van I see you have it fixed up pretty nice." I started to get nervous, and he took my keys and opened the side door. He stepped in and pulled me up, I had to bend low so I didn't hit my head. And then we both ended up on the couch together.

I was so nervous but in my heart I loved it. He did most of the talking and he took my hand a couple of times and we sort of intertwined fingers. Our hands were just touching but I found it so erotic and exciting. "Maybe I should close the door." He said and then, thump, we were alone together on the couch. I tucked my legs under myself and I drew my skirt around me. It was still a little light out being about 6PM, and I knew noone would be able to see inside with the curtains closed. He moved over and started to touch my hair. "You have beautiful hair, I love blonde women." I then asked him if he was married. He didn't stop playing with my hair when he told me. "I am, but I only get to see her on weekends. A man misses a woman on the road."

He then said something that I still dream about, it made me melt inside. He was lightly putting his fingers on my earring then cheek when he said. "I'm going to be thinking about your pretty face when I'm with my wife this weekend."

It sounds a little creepy now, but to a twenty year old crossdresser it was a perfect compliment. I don't know what happened to me but I looked at him and suddenly we kissed. It was my first kiss from a man, an older one at that. He had to be at least 35, and he was married, and so good looking. I let him kiss me and suddenly we were making out on the couch. I was sitting on my legs and I moved closer to him as we made out. I felt him rub my bare shoulder and he moved down to my breasts and I got so nervous, I steered him to my nylon clad legs. While he played with my thighs I put my arms around him and felt my body and breasts press against him. "Mmm." Was the only thing I could say.

His hands roamed my legs and down to my feet and heels. I was getting very excited as he started to kiss my neck and play with my hair. He kept telling me I smelled so good. He then looked at me and grabbed my hand and put it on his crotch. I could tell he was gauging my reaction. We just looked at each other for a couple of seconds, and then I started to massage him through his jeans. "Your hands feel so good baby." I guess I made the right decision, because he was smiling and I felt myself getting so wet.

He was tremendous in his pants and I knew I had to take care of him. We stopped a couple of seconds later while he fished his dick out. Once he was standing tall I barely got to touch it and I started to cum in my panties. The orgasm just came, I was totally unprepared for it. I moaned and kissed him while I jerked him off. I have never been so turned on. I played with his dick and even reached down and rubbed his balls. I felt so wanton and slutty playing with a man's cock when we only met an hour and a half ago.

As I was coming down from my orgasm he told me. "I'm gonna cum baby girl." I pushed on this dick some more and heard the jangle of my bracelets as I felt it pulse, and soon his cum was in my hands. He was breathing heavy as he nuzzled my neck and shoulder. He must have spurt about seven times, I was amazed at the amount of jism coming out of him. It was all over his jeans and the couch, and some on my skirt. "Now that." he exhaled. "Was fantastic, thank you darlin'." He smiled at me again and kissed me once more. I was so content, I didn't want to let go of his cock.

I cleaned him up with a tissue and when he wasn't looking took some of sperm into my mouth. I had to do it. I sucked the bit that was on my finger, and I'm so happy that I did. I still dream about that moment to this day. "I better go baby girl. Let's meet again." He gave me his number and I gave him the number to the Pizza Place near my house. We both got out of the van and he put his arm around me. I looked at him and put my arms around his neck and brought his face down to mine and kissed him again. We made out a little while longer in the parking lot with truckers and families driving by. I didn't want him to leave. We said goodbye. I stayed there and watched him move toward his truck. He turned around and smiled at me and then made his way to the door. And then he was gone. Of course I went in the back of the van, sat on the couch and came again. My legs looking even more feminine in my pantyhose than before. God I was so excited. My first man.

***

The next couple of weeks I often fantasied about meeting him again and calling him up. A little make out session on the side of the road. Super excited that I might end up talking to his wife. I have flashed truckers a couple of more times after that but never did get to meet another one. I always remember that summer and driving on the highway in my heels. I wish I had the nerve to do it again.

The End