My Lesson In Hitchhiking

Hi, this is my first story here. It happened to me a couple years ago when I was in grad school, 26 years old.

My boyfriend and I broke up that semester a couple weeks before final exams. I did relatively OK since I was busy working on my experiment, writing a paper and studying for two exams. After it all winded down and break came up—the first I had in a long time, I started to feel a bit lonely and didn't know what to do. I was studying in a college town that was mostly surrounded by farmland and small towns with nothing to do or see. Not having had sex in a while, and being near my period which always makes me horny, I was also getting quite hot and frequently found myself using my vibrating massage tool for its unintended use.

Not into going out and picking someone up from this small town to take home with me (they probably knew people I knew anyway), I started thinking of adventurous sexual escapades I could get into. The one I decided on was to hitchhike with one of the many truckers that brings stuff in and out of town, go a ways to another town and then hitchhike back. The fun part would be that I was going to wear my light summer dress without bra or panties, seeing as how it was so hot out anyways. It was concealing enough that I could look decent if I didn't want to be seen, but also let me reveal a few things if the right opportunity arose. When standing up, it revealed my upper chest down to where the top of my small breasts just started to show (but no nipples). On the bottom, it came down to mid-thigh. I liked to reveal just enough to get someone excited, then think of them going home and jacking off while they think about me.

I hid $80 in my sock just in case and I headed out mid-day to the road most trucks leave from. The second one I hailed stopped 30 feet in front of me, so I ran up and got in the cab. I looked over at him and noticed that he was actually good-looking, rugged, but nice and I was happy to know things were going well. I asked where he was going, and he named a town about 65 miles away. I said that was where I was going too, I had a friend there to see. I thanked him, closed the door, and we were on our way. He tried to make conversation, obviously interested in me, but I just sort of dismissed the horribly boring small talk and said I needed to get some rest. I strategically turned to my right side and bent my legs up a bit so that the bottom of the dress was just below my ass. I curled up and pretended to drift off to sleep. I was in a position that was just right for looking into the side mirror so I could see the driver out of the corner of my eye.

It didn't take long for him to stare down at my revealed legs. I could feel myself getting very wet. This was exactly what I was looking for, I thought. I pretended to stir to get more comfortable, having the effect of making the back of my dress ride up just a bit more, now exposing the bottom inch of my ass. I could feel the air on my upper thighs, and it made my juices start to flow. I was afraid he would see or smell them, and think I wanted more than just his eyes. If he could see my pussy lips, it was just a little and they were closed, so I thought it was probably safe to assume he wouldn't notice my wetness. I just relaxed and watched as he stared down at my "accidental" exposure, and I could hear him rubbing his jeans and trying to get comfortable. I wanted to be able to reach down and touch myself, but that would be impossible without him noticing, and I didn't want him to expect anything more than what he was already getting. It wasn't long before we came to our destination, and I yawned, casually readjusted and stepped out of the cab. I thanked him for the ride and walked in the other direction.

I looked back and watched him go towards the restaurant that was connected to the gas station, and saw him greeting another guy who it seemed he knew from before. It was obvious he was explaining his "lucky ride" and that settled it for me—I got exactly what I was hoping for and couldn't be more happy. Pleased with myself, I went to have a bite to eat. It was starting to get late, so I decided to head to the road going East of there, planning on making somewhat of a semi circle. I wanted to get home soon so I could relieve myself. Again, not surprisingly, it was easy to wave a truck down and soon I was climbing up into the second cab. He was going exactly where I had wanted to go, so I sat down and closed the door as we took off.

He wasn't nearly as attractive as the first guy. He had a gut, but at least he wasn't completely round or flabby. He just wasn't much to look at. He was rugged like the first, and as I looked at him he looked more and more familiar. Then it hit me—he looks exactly like the guy that was talking to the first trucker. My blood suddenly ran cold with embarrassment and worry. I was not in the least attracted to him, and did not intend to give him the same show. Intent on covering up as much as possible and hoping the ride passed quickly, I sat up keeping my eyes open. Unfortunately, I realized because of his height advantage he had too good of a view down my front, with a good amount of my breasts visible and my nipples poking through the fabric of the dress. I finally opted on turning to my right like I did with the previous driver, but this time loosened the straps just a tad so I could pull the dress a little farther down so it covered my back all the way down to my mid thigh. Again I could see his face in the side mirror, so I felt pretty assured that this would go OK in the end. Of course he was constantly looking, disappointedly, over at my ass, but I knew he couldn't see too much so I just sat there and rested. Eventually I started to drift off to sleep, soothed by the motion of the truck on the road.

A while later I woke up and noticed that air seemed to be somehow reaching my ass as before. I looked in the mirror and noticed the driver still staring at my ass, but this time I feared there might be something to see. It was clear he was jacking himself off—I could hear the movement of his hand and see his head shaking in time. I soon realized that my dress had been pulled up to the top of my ass, and I'm sure it couldn't have ridden that far up on its own. My entire ass was now exposed, and with my knees bent up I knew that my pussy lips, although closed, were also visible. I didn't know what to do. I didn't want to get up and let him know that I knew because I didn't want to have to address it and deal with the awkwardness afterwards. I thought I would stir and make him think I was waking so he would put everything away.

I yawned and stretched my arms out, and in my half asleep state I hadn't thought how the stretch would affect his view—I felt my pussy lips part slightly, and felt them stick with the moisture that I could not help but produce considering the thrill of the situation. I relaxed back to my original position, and waited for him to cum so he would put his thing back in his pants and cover me up. However, after several boring minutes I only fell back asleep again as I waited. I woke up again as we pulled into a rest stop, and was very pleased to find my dress back where it was, covering me completely, and him sitting there fully clothed and not touching himself. He went over to the men's room, probably to finish jacking himself off, I assumed.

Relieved, I got out of the cab and headed towards the bathroom. I could still feel that I was really wet, but then realized that my period had actually started as I felt it drip down my leg. I was embarrassed to think he might have seen it. I rushed to the ladies room and into the stall to clean myself off. To my surprise, there was no blood but thick white liquid that was dripping down from my ass. In a panic, I wiped his cum off of my ass and legs, being careful not to get any of it in my vagina. This jerk had an impressive amount of sperm, it had filled up my ass crack and covered my anus, and I had to be very careful as I wiped the stuff outward off of my pussy lips and pulled it out of the untrimmed pubic hair that covered the sides of my vulva. After the outside was as clean as I could get it, I nervously put my finger on the inside to make sure nothing got in. Fortunately, it was clean. Nonetheless, I started heavily considering taking the "morning after pill" when I returned just to be on the safe side.

I finished wiping what dried cum I could off my ass cheeks, then tried to think of what to do next. Despite my worries, it was nonetheless a very erotic situation and had me quite turned on. I though of getting myself off, but decided it was best just to get out of there and find another ride home, so I walked back out to the parking lot.

to be continued...