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. I opened the makeup case and saw the beautiful shade of lip stick. I quickly applied it in the manner I had practiced so many times imitating my sisters as they were getting ready for dates. My lips were perfect and full brought out by the gloss of the lipstick. As I admired my work a more impatient knock again came at the door. I took one last deep breath, put my head down and turned the door handle to exit. The twenty something guy standing there was clearly miffed and was about to tell me off but stopped dead when he saw me emerge. ‘Sorry girl, if I had known you could have had as long as you wanted. Looking good!’ I felt my face flush but I just kept my head down and mumbled in a high voice ‘Sorry the women’s was out of order’ as I pushed past him. Shivers all over my body especially as I felt his hand brush my upper thigh. The touch made me gasp and I forgot myself for a moment and looked back at him and smiled. He smiled broadly and his eyes almost froze me as he surveyed me up and down. I remember playing dress up with my sisters and Halloween and fell into a convincing feminine walk taking short crossing steps that sent my hips swaying. I didn’t look back but knew that he hadn’t entered the bathroom. I felt his eyes on me and heard the low whistle in my ears. The hair on the back of my neck was on end and I felt electric. My stomach was churning and I knew I dare not look back again. I saw the car on the other side of the parking lot and headed to it trying to be unhurried. Two men pumping gas saw me and their eyes never left me. I reached the car at last but it was empty. No escape. The wind caught the hem of my dress and I wasn’t quick enough to prevent it from lifting and briefly showing my panties. I smoothed it down but saw the looks. At last Jim appeared and was obviously taken aback but clearly also very pleased. He came right up to me and we almost touched as he leaned in to unlock and open the door for me. I got in and tried to be modest as I swung my legs in. I wasn’t entirely successful. He closed the door and climbed in the driver’s side. I could see the approving looks from the guy’s at the pumps and now also the guy at the washroom who had never actually gone in. ‘Wow!’ Jim said. ‘If I hadn’t picked out that dress and those heels I never would have recognized you and never have thought in a million years that someone looking like you would be getting into my car on a business trip!’ The blush that was just settling rose again in my cheeks. ‘I’m sorry about the shoes. I didn’t know what to do. Someone came to the door’, I quivered. ‘Don’t apologize for a second. The view was totally worth it and it was actually my hope that you would wear the shoes.’ Jim volunteered. ‘Did you see those guys drooling over you? How did that make you feel?’ I felt paralyzed in my seat and Jim reached over and pulled my seat belt across me. I felt his hand on my hip as he buckled it and it was like an electric shock. I trembled as I tried to compose myself. The next few minutes were a bit of a blur as we pulled back out onto the road. I shifted self-consciously in my seat as I realized that every movement pushed the hem of my short sundress further up my thighs. It was impossible not to notice Jim’s gaze straying to my feet, calves, thighs, chest, neck, hair and face. After a moment he said, ‘Oh I almost forgot, they didn’t have any milkshakes to replace the spilled one but I thought you might enjoy this.’ He handed me a Rocket Popsicle. ‘I hope you like these. They were all they had. I think that one is lemonade flavored. That’s why it’s deep pink.’ I took off the wrapper carefully and it was indeed pink and like a half of a regular Popiscle only bigger and with just one stick. I put it too my lips and licked it to get a taste of it. It tasted good so I put the tip in my mouth and started to suck on it. I definitely liked it and absolutely didn’t want to make another mess in the car so was very careful to keep licking and sucking the entire length so it wouldn’t drip out of my mouth. A couple of times the car swerved a bit as Jim seemed to be watching me almost as much as the road ahead. He chuckled and told me I should look in the mirror as the pink color was totally coming off on my lips. But he said not to worry as it looked very good on me.
Finally after what seemed like forever he asked again, ‘You didn’t say how all that made you feel? Was it like Halloween again?’ I felt myself blushing again but words escaped me. But inside I knew that that is exactly what it felt like. Like Halloween. Knowing guys were watching me. Imagining what they were thinking. Imagining what they wanted. Imagining above all what it would be like. I remembered a day when I had stayed home from school feigning being sick but really planning to spend the day in the empty house in my older sister’s bedroom playing dress up with her things. She had such beautiful things. I hid in her closet when she came home at lunch with her boyfriend. I peeked through the closet door louvers and listened as she gasped and moaned and almost screamed for the next 40 minutes and then left all too soon. The memories of how she took him first in her mouth and then below were burned into my mind. The look on her face. I had always thought she was gorgeous but I had never wanted to be her so badly as for those 40 minutes…
His voice again, ‘Did you like the way it felt? Do you? You can tell me, I promise that I would never tell anyone. You can trust me.’ And at last I let it out and I did trust him. ‘Yes, Yes I did like the way it felt and I do like the way it feels. I love the way it feels… I’m sorry. Is that wrong?’ ‘No no of course not. Everyone has the right to feel how they feel. It’s absolutely not wrong’, he said supportively. I felt tears in my eyes. ‘It’s alright’ he said. I couldn’t stop from crying ‘I’m sorry’ I said. ‘It’s ok’ I felt his hand on my thigh as he repeated himself. I could barely hear his words. My body was shivering and on fire at the same time. I felt tingling in my bottom, my nipples were erect and straining against lace and silk, the hair on my neck was on end, I gasped. I felt like I was going to pass out. And then my left hand became separated from my body. I just couldn’t help myself. This nice man who had been so helpful and understanding… the hand found its way to his thigh then his groin and far beyond all its hope it found him… hard! Straining at the fabric of his pants. I squeezed. The car swerved and lurched to the side of the road. Suddenly my hand was mine again. I pulled it back. ‘I’m so sorry. So sorry’ and started crying again. He leaned over and took me in his arms. I sobbed but drank in his strength and masculinity. ‘You took me by surprise’ he said. He apologized for his aroused state but said that it was a natural thing when in the presence of such beauty. He said that he was sure that my appearance left every man at the gas station in the same state as he was and that I should be flattered. I was very confused but I was very excited by the thought of these men and the effect that I may have had on them. He spoke softly in my ear and the feel of his words were intoxicating. After a time he said that we were almost to his home and I realized that we were not far from mine either. He calmed me and said that we should carry on to his home where I could get cleaned up and change back into my dry clothes.
When we pulled into his house I was surprised that it wasn’t bigger as I knew he had a family and was driving such a nice car. He pulled the car straight into the garage and the door came down behind us. He said that I could be totally relaxed as no one was home and I was so relieved. He came around and opened my door for me and gave me his hand to help me out. I once again tried to exit as modestly as I could. The cool air in the garage felt strange on bare legs and my almost bare bottom. I had almost forgotten how I was dressed in the last part of the ride. He gave me a long look again and then reached into the back to get my clothes out. ‘Still damp’ he proclaimed. He said that he would put them in the dryer and that I could have a shower to get any residual stickiness off. He led me into the house and directed me up the stairs and then followed. He led me to a door and said that this was his older daughter Megan’s room and that she had an en suite that I could use to shower. He was going to go down the hall to the master bedroom and then he would check on my clothes and bring them to me. I thanked him but felt a pang of disappointment deep inside that seemed very strange. I went into his daughter’s room and closed the door. I couldn’t resist glancing around. It was very girly just like my own sisters’ rooms but also there were some more grown up things. The newer pictures on the mirror showed her and her friends at parties and they were all gorgeous. What I figured was Jim’s daughter was smoking hot with gorgeous legs and shortish hair that she wore tussled. I looked in her closet and there were heels and boots and dresses and skirts to die for. Her dresser was right by the bathroom door and I just had to! The top two drawers had some of the sexiest bras and panties I had ever seen. I felt myself growing as I played with them. There was nothing I could do. I undressed and laid the sundress and undies out on her bed and got in the shower. The water felt so good. I soaped myself all over and it felt so good. I lingered on my bottom and I felt ashamed and excited when my finger found its way to my special place. I played there for a few minutes with the warm water and soap pushing me past the edge as it always did. My legs felt weak afterwards but I wanted to be completely clean. There was a bottle of strawberry shampoo that smelled so good and it felt so good in my hair. Finally I rinsed and got out of the shower and dried myself. My hair was still damp when I went back to the dresser mirror with her pictures. I looked at her hair and took the brush and thought I could get it just so and after a few minutes I thought I had done a perfect job. The dresser was covered in different makeup things and I knew from my sisters what almost all of them were for. There was a beautiful shade of dark pink lipstick just like the Rocket Popsicle and just like the shade she was wearing in three of the photos. I laughed ‘why not?’ and applied it. It made my lips look so full. I was surprised. I feigned pouting and kissing. And then of course I realized I was naked in a strange girl's bedroom in a strange house. With no clothes of my own… I thought that I had better put something on so I am at least covered when Jim brings my clothes back. The panties and bra I had been wearing had a bit of stickiness on them so I thought better to put something clean on. Jim was going to have to do laundry anyway. A very sexy red satin and lace pair of boy shorts and matching lacy padded bra caught my eye and I was in love. I put them on and looked in the mirror. OMG! It turned out that the sundress was a bit too sheer to hide the red undies so I went to the closet and found a short red cotton Lycra dress that I pulled on. It was almost too short but it gave me curves that were amazing and I did a little dance in front of the mirror. What else was in the closet? The perfect black clubbing ankle boots among the many pairs of gorgeous heels. I tried them on and my legs and ass were absolute 10s!! What I wouldn’t give for all of this!! Lol.
It seemed like Jim should be back with my clothes and now I was worried that he would be furious that I had touched any of his daughter’s things. I poked my head out the door. Definitely no sign of Jim. The door to the master bedroom was closed but I thought that I could hear something coming from inside. I quietly crept down the hall on my newfound heels. I was at the door now and the sound from inside was definitely louder but still indistinct. Both male and female voices. I freaked thinking that Jim’s wife was home and that I was going to be in so much trouble. I cracked the door open and was relieved when I saw that the voices were just from a TV at the foot of the bed. ‘It’s ok. You can come in if you want. I’m sorry I just couldn’t wait and figured you would be a bit longer.’ I heard Jim’s voice say. I saw him on the bed as I entered and I realized that video on the large screen TV was that of a gorgeous teen tending to a man with her mouth. He looked at me and his jaw dropped. His cock was hard and it was beautiful. I couldn’t take my eyes off it as I blurted out that I was sorry and that I was worried when I heard voices thinking maybe his wife was home. My eyes looked back and forth at the TV screen and his perfect cock… he motioned me towards him. ‘You don’t have to worry. My wife won’t be home. We’ve been separated for almost a year and I moved into this house 6 months ago and keep the other two bedrooms for my daughters but they are only here every other weekend.’ He must have seen the wheels spinning in my head and seen my face brighten. Here he was. All alone. Maybe 15 minutes from my new house. All alone. So understanding. All alone. And with that… that beautiful thing! I found myself at the edge of a precipice, confused but certain. ‘You’re very beautiful’ he said. ‘Every bit as beautiful as my daughters or your sisters I’m sure’. ‘Do you like what the girl in the video is doing? Is it what you saw your sister doing? Have you been thinking about it a lot?’ I nodded catching a glimpse of myself in the mirrored doors of the closets that covered one entire wall of the master bedroom. God, he’s right, I am beautiful and crazy hot. ‘Come sit down and watch with me for a minute. It’s ok don’t worry.’ I instinctively fell into my most seductive walk, practiced hundreds of times while play acting movie stars with my sisters, as I approached the bed and sat my bottom on the edge. I wasn’t really worried at all but the butterflies I was feeling were making me crazy.’ I watched the video. It was all so beautiful. I remember the afternoon in my sister’s bedroom and I so wanted to be just like her in every way. Jim’s cock was so hard. So perfect. I licked my lips. I had forgotten that I had put the lipstick on. On the stand beside the TV were 8x10’s of Jim’s daughters. Both gorgeous and Megan wearing the very lipstick that I had on now. I took one last look at the video, then into Jim’s reassuring eyes and finally leaned forward licking and then parting my lips… to be continued.