A Summer Ride by drivingallnight..,

This story is based on an experience I had as a teen and the fantasies (and realities) that grew from the experience. , When I was a teenager, my mother and father divorced and I moved from a small town to a large city with my mother and two older sisters. In the following summers I hitchhiked back and forth between the two places a few times. On one of the occasions a guy who was about 45 picked me up and gave me a ride.

I have never been a large person and didn’t really have my growth spurt until I was 19 so at 18 I was maybe 5’ 6” at the time and very slim maybe 110 lb. It was a hot, sunny summer day and I was wearing cut off jean shorts and a t-shirt. He was a very nice guy and we were chatting about lots of things. His name was Jim.

He didn’t live too far from my new home so it was a huge bonus when he picked me up over an hour and half away and he was heading home. It’s not often that I got such a long ride and it was going to save me a huge amount of time. So we talked quite a bit on the way. He had two daughters that were 16 and 18. I told him that I had two sisters who were also close together in age.

My mom had all three of us in rapid succession and my sisters were 1 and 2 years older than me. He said that he had been away for a week on business and always made a point of bringing his girls something nice home as a gift. He asked me what it was like to have two older sisters and I said that it was fine but that I was sure that they had wanted another sister and that having two sisters and no brothers meant that I was always stuck playing Barbies and that dress up time could be interesting but that it was all good and I didn’t really mind.

I even told him that I had one a prize in school at Halloween for my costume as a princess and that I loved the beautiful blue gown I got to wear and that I got used to the shoes in no time. I told him how many compliments I got at Halloween that year. Even as I was telling him the Halloween story, a voice in my head was saying, ‘too much information!’ But although he seemed to be looking at me a bit oddly as I told the story, he was really nice and interested and totally accepting and for whatever reason it made me very comfortable opening up to him.

After about 40 minutes he asked if I wanted to stop for an ice cream as there was a spot along the highway coming up where everyone stopped. It was a warm day so I said sure of course. I got a chocolate milkshake and he got a strawberry ice cream cone. We got going again and I was really enjoying the milkshake though it was so thick that I was really having to suck on the straw quite hard.

He saw me and laughed and said that I sure was working hard at it and he admired my determination. He asked me if I would like to lick his and of course I wasn’t going to refuse. I had a few really good licks and couldn’t help but notice how he was looking at me. It was same way a few guys had looked at me when I came to their house in my princess costume but I wasn’t really sure of what it meant just that it made me feel a little funny and tingly inside. It was a nice feeling. Kind of exciting in a way.

Very shortly after I was busy working on my milkshake when he had to brake suddenly for a truck in front of him. I was so embarrassed when the shake spilled all over me and onto his seat. I had milkshake on my shirt and soaked right through my shorts and it was on his car seat. I couldn’t believe how good he was about it. I was figuring he would be so angry. I apologized so much! Fortunately, the seats were leather and there was a gas station right up ahead that he quickly pulled into.

He grabbed a bunch of paper towels from the pump area and came over and wiped the milkshake off me. He rubbed me everywhere the milkshake was and it made me feel really weird. I could feel myself rising my nipples got totally hard. I had to ask him to stop as I was worried what might happen. He went around to the trunk and got a towel out and told me to get up out of the car so he could clean the seat. He had pulled around the side to where the washroom was and told me he would go get the key so I could go in and get cleaned up. He gave me the key and said that I should go into the men’s room and get cleaned off.

I was almost in the door when he called me and said ‘wait a minute’. He went to the trunk again and brought out two gift boxes with bows on. He could see I was puzzled. ‘These are the things I got for my daughters. I can see that your shorts are soaked right through and your shirt is a mess too and you are going to be miserable for the rest of the drive in those things. I know that these are girls’ things but I am sure you will be more comfortable. Both my girls are about your size so I am sure something will fit. You can rinse your stuff in the sink in there and wring them out. By the time we get you home everything should be dry and you can change back and no one will be the wiser.’ I smiled nervously but did feel wet and sticky in my things and said ok.

I went into the bathroom, locked the door and did what he said. I was totally nude when I opened the two gift boxes. I figured he must have bought jeans and some t-shirts for them if he intended me to wear them. My heart sank when I open the first box and found a matching white lacy floral pantie and bra set and sundress. The things were gorgeous but definitely I was mortified though I felt other feelings as well. They were hard to describe. My hope was on the other gift box but I had no luck there either.

The box contained a very pretty pair of open back heeled shoes and a travel makeup kit complete with lipstick, blush and eye makeup. I definitely didn’t need blush at that point. My face was flushed beet red. So now I was in trouble. My shorts, underwear and shirt wear soaking wet and no amount of wringing was going to make them wearable. All I had were my shoes. I hadn’t even been wearing socks that day.

I looked again at the things meant for his daughters. They were gorgeous and I loved the way they looked and felt but just felt that there was no way I could wear them. Just then a knock came at the door and a reassuring voice asked if I was ok and said that I shouldn’t worry as no one would see and that it would totally be our secret. I could change back into my own clothes once they were dry.

He was so nice and I really did love the way the clothes looked. He said he had to run into the gas station for a minute and that he was just going to move the car to the side of the station’s parking lot and to come out to car when I was ready. He told me to hand out my wet clothes so he could put them in the back window of the car so they could start to dry. His voice seemed a bit firmer that it had been during our conversations. I weakly said ‘ok’ and opened the door a crack to hand out my clothes and then quickly locked the door again.

I took a deep breath and looked at the things again. The bra and panties were so pretty. But also sexy with their lace. I imagined what his daughter might look in them and felt a stirring in my loins that I immediately realized would lead to a big problem if I were going to actually pull this off so I put the image out of my mind. So there I was. Confused and excited at the same time but now with really no choice in the matter. I picked up the undies and gently put them on. The feel of the material took my breath away as it contacted my sensitive areas. Trouble again! I reached down and tucked my somewhat my small penis deep into the cleft of my legs and my sack was pushed far back. I looked at the myself in the mirror and saw that it might work.

The front of my panties was convincingly flat. I couldn’t help but turn and look over my shoulder at my behind. I had been skating my entire life and the panties made my butt look truly gorgeous. I closed my eyes to stop what was for sure going to follow if I kept looking at the panties and my ass. My nipples got hard in response to my thoughts of my behind and I now pondered the sundress. It was beautiful. The material was quite thin and almost sheer but thankfully not quite. I was worried though about the effect that it might have on my nipples and convinced myself that it would be safer to put the lacy bra on first to give myself some protection.

It felt marvelous too and had just enough padding to give the illusion of maybe a pert B breast. I wondered again about his daughter… So finally the dress. I quickly pulled it over my head eyes closed. When I opened them I was surprised. I actually looked very pretty. I guess I shouldn’t have been so surprised given my experiences playing dress up with my sisters and at Halloween but this was striking. I wasn’t sure quite what it was, the perfect bra or the cut of the dress or the fact that my hair was a bit longer than usual for summer or my summer tan.

I admired myself in the mirror. I looked at my hair. I tossed it a bit and I realized that I looked just like one of those incredibly hot somewhat athletic long-legged gorgeous ass girls that always made me wish that I were the captain of the football team. I gave myself a flirtatious teasing pout and had to stop again before I totally ruined my look. My fantasies were interrupted by a knock on the door.

He’s back already… how long has it been? I was filled with panic when I realized that the voice on the other side of the door was not that of the nice man who had shared his ice cream. ‘Come on. I have to use the washroom’. Oh my god I thought. What am I going to do? Then I caught my reflection in the mirror again and I knew exactly what I was going to do. I quickly went through the gift wrapping and boxes in the trash. The makeup kit was essentially in a small purse so that was no problem. I looked at my worn running shoes and thought ‘no way are they working’ and threw them in the trash. I slipped the heels on thanking God that they pretty much fit.

I looked back at the mirror one last time and it took my breath away. The heels were the finishing touch to make my legs and butt look perfect in the sundress that came to mid thigh and was maybe a bit tighter on me than was meant to be. I was for once thankful that I had so little body hair, something that had always led to teasing in the gym change room and shower. Knowing that there was a somewhat angry stranger standing on the other side of the door gave me one last push – I couldn’t be found out.