Leaving my part time job at a bowling alley it was always too late to catch the last bus home so I’d hitchhike. It generally didn’t take too long to catch a ride and the city was still small enough for hitching to be fairly safe. An older car driven by a middle aged man pulled over. I got in and told him where I was headed and he said he’d wasn’t going that far but where he planned to turn was only a twenty minute walk from home and a lot closer then where I was now. We started to talk a bit as he drove along and found we were both interested in electronics. It wasn’t long before we got to where he was supposed to turn off but instead he went straight. We continued talking and eventually he asked for directions to where I lived. He parked across the street from where I was living with my mother and sisters. We continued to talk and I noticed that now that he didn’t have to keep his hands on the wheel he started gesturing a lot. He’d gesture then let his hands drop which always ended with his closer hand resting on my leg. I didn’t notice this at first and have no real idea how long he’d been doing it before I did.
I sorta lost track of what he was saying at times after I noticed his hand placement as I became focused more and more on his hand and where it was landing. A bit higher, then a further bit higher, then just a bit higher again. Trying to think back I realized it had started about my knee but now it was halfway up my inner thigh! He let it rest there longer and started to gently squeeze and make small circles with his fingertips between further gestures and movements up my leg. I kept trying to catch up to what we were talking about but the sensations generated were making that difficult. The back of his hand just started to brush against my crotch and he was watching me stare at his hand with a smile on his face and who knows what might have happened if a police car hadn’t slowed down as it passed by and scared him into basically kicking me out of the car and hurrying off. As I got out I let him know that I would be hitchhiking three days from now at the same spot.
For three days I spent a lot of time thinking about what his hand had felt like and how it had resurrected feelings I hadn’t had for a long time. When I was entering my teens I’d been babysitting for one of my sisters and looking for something to read when I saw her open lingerie drawer. I have no idea what came over me as my mind blanked out and I didn’t consciously think until after I had stripped off my male things to slip on a white lace corset, tan nylons and the matching panties. My only conscious thoughts at that point were to wonder what heels and dress I should wear over them. After I managed that I felt so relaxed and relieved and like something was set right with the world. I’d felt a flash of that again but it didn’t feel quite right either. It took a day before I thought of what that was.
I’d felt feminine and passive as I accepted his hand exploring my leg and when he did it again, and I knew I’d manage to somehow make that happen, I wanted to be properly dressed and done up for the occasion! I managed to make myself do some shopping at a local thrift store. A blouse, skirt and a pair of three inch heels added to what I’d stashed in the garage from younger days were stuffed in my backpack along with some stolen and purchased make up. I’d thought about it, planned it, and now it was time to see if I’d have the fortitude to show someone what I looked like in feminine clothes. I shaved my body when I got home from school, dressed and headed off to work.
At work I was distracted and the boss noticed but I put it off to meeting a new girl. Not that this job required much concentration. I managed to leave a few things to do late, like the washrooms, and despite having to hurry to get them done I had the time to slip on the lingerie, apply what would be called a base coat of foundation, concealer and light blush that looked natural from a distance so no one noticed. I left work feeling so surreal in the lingerie’ and light make up but still in my male outerwear. Now I just had a few more things that had to click into place.
I waited till I saw his car coming along and with a sigh of relief stuck out my thumb. I hadn’t known for sure he’d show up and had been anxious about it; really anxious! He slowed and stopped and a slight smile crossed his face; he was still interested and a lot calmer then he had been. I put the backpack between us on the seat and smiled at him as he drove off. We talked a bit and then I asked him if he could stop at a gas station so I could use the restroom. I was shaking a bit as I got the key and grabbed my backpack from the car. Inside the restroom I had to take a few deep breaths to calm myself before I could do anything. First I finished my face, eyeshadows, more rouge, eyeliner, mascara and of course shocking pink lipstick. It only took a minute or two. I combed out my hair and sprayed it into a feminine updo then slipped off my pants, shirt and shoes.
I started to shake again as I stuffed my bra with the partially filled water balloons and did up my blouse. I straightened and tightened my garter belt and nylons, slipped into my skirt and and took a few more deep breaths to calm myself down a bit more. I looked at my reflection, wondering if my skirt was too short; it ended about where the tops of my nylons started, just managing to hide the dark bands on the tops. I stuffed everything into my backpack quickly and wondered if he was still waiting, hoped he was still waiting. He was! His eyes opened wide for a few seconds then he acted like there was nothing different as I got into the car. This time I placed the backpack on the floor and slid across the seat to sit beside him. I was still trembling and nervous, wondering what he was thinking, how he’d react to this, would he still be …..
I needn’t have worried, I discovered, as his hand caressed my leg for a few seconds and he smiled at me widely. Raising his hand he tilted my head up, leaned forward and kissed me. Not the long deep kiss I wanted but a simple kiss befitting where we were, yet it still sent a thrill running through me and shook me from head to toe. Leaning back he took a minute to run his eyes up and down my body appreciatively before putting his car in gear and resuming the drive. His free hand returned to caress, fondle and squeeze my leg and send shivers through me. Again it slowly moved upwards until I softly moaned as the first finger slid up above my nylon top and touched my smooth bare skin.
Stopped at a light his eyes held mine as he stared deeply into them as his hand pushed up the front of my skirt. He glanced down and my eyes followed his. The sheer front of my panties were exposed and my throbbing clit filled the front, stretching it outwards. So softly I could barely feel it his fingertips, he traced the outline. I closed my eyes and trembled at first then shuddered when he pressed his hand down and used his palm to stroke it. He told me he liked my panties as he lifted his hand and I smiled widely as I thanked him. In fact, he went on about how he liked the way I was dressed from head to toe; was it just for him?
Unable to talk at the moment I just nodded as he chuckled and went back to tracing his fingertips along the lace trim of my panties while he drove. I didn’t object when he turned early; in fact it barely registered in my mind! I was more overwhelmed by the sensations his hand was sending through my thigh. It ran all the way up and down my body making my breath short and my heart race. I wasn’t in real control of my actions or responses. Like when I was dressing before, I was along for the ride and enjoying every tingling sensation, every sensual wave of pleasure, every caress of his hand along my thigh or across the front of my panties. I couldn’t have done a thing to stop it; I didn’t have the will or desire to.
He turned down a street and into a driveway then shut off the car. Looking into my eyes as his hand stroked the front of my panties and made my body shake and tremble uncontrollably. Leaning forward he kissed me first softly and then deeper, plunging his tongue between my lips. I closed my eyes and returned his kiss; flicking my tongue around his and feeling myself melting against him. I have no idea how long we sat there kissing before he sat back straight, opened his door and came around to open mine. My knees buckled as I got out but I was able to catch myself before I fell. He smiled at that and put his arm around me to steady me then helped me up to his house.
By the time we reached his door I was steady on my feet and while I didn’t need his arm around my waist I liked having it there. Once we got inside my knees buckled a bit again when he kissed me deeply. He chuckled at my reaction then steadied me over to his couch and left me there while he fixed us drinks. Returning with the drinks he sat beside me. We talked a bit while he idly played with my legs, running his hand along one then the other; making me a bit distracted and slower to answer his questions.
No, I hadn’t ever done anything like this before. Yes, I had thought about it ever since the first ride. I was both scared, excited and wondering why I had done this and had no real reason aside from some need inside. Yes, it was the first time I had ever let anyone see me dressed this way. No, I hadn’t thought about anything like this before. If I hadn’t met him I doubt I would have tonight. I asked him to call my mother and explain that I was staying over with his son if that was OK with her. He did with a smirk on his face then asked me if his son would have had the pleasure to bring me over like this. I blushed and said it wouldn’t have been likely unless his son was the one to play with my leg.