When I was 16 years old and growing up in the sticks of Vermont I use to hitch hike to get where I needed to go. Being a girl it helped, in the Spring and Summer it really helped as I would dress for success. I grew up near a college town and there were always cars on the road. I had many opportunities to do just about everything, but always flirted and just got the ride.One day I had hitched into the closest city to see my boyfriend. I went to a regional high school so you could be dating someone 30 miles from your house, which is what was happening to me. He got a ride to the city with his mom and I had to hitch as my mom worked- actually it was my mom who told me to hitch hike (things were a little different 10 years ago in the sticks.)My boyfriend and I had spent a couple of hours in the movies sitting in the back row like we usually did. I had been fingered to a couple of climaxes and he got his weekly blow job from me. I wanted to do more with him but the week before we were going to go ‘all the way" this girl at school had gotten pregnant and I was terrified by the idea.Anyway we left the movies, he got picked up and I headed out of town with my thumb in the air.I got a short ride which actually hurt instead of helped as I was left off in the middle of nowhere. It was dark and I was getting cold. I was there over 30 minutes and swearing like hell that I couldn’t get a ride, every car that went by me got the finger for passing me.A car finally stopped and I went running to it. I got in and there was a college age looking guy. He asked me where I was headed and I told him. He said he wasn’t going nearly that far. I had to think fast. I said "god it feels so good to be in a warm car I was freezing out there." I took off my light jacket. He turned the inside light on and stared at my braless boobs and said "nice." I looked at him and said "what?" playing dumb. He turned the light back off and watched the road. He said "maybe if you showed me your tits I could go a little further." Now I have never done anything but tease in the past, but this guy wasn’t bad looking and I did not want to be on the road alone again. I said "OK" he turned on the light and I pulled my tee shirt up exposing my young firm tits. I pulled my shirt down and he turned off the light. He said , well my turn off is right here, I guess that got you a couple of more miles. "shit" I thought I have 12-15 more to go. He then said – "you know if you pulled your pants down I it would help me take you a little further". I thought about it and figured -what the hell, he would be the 4th boy to see my pussy, and I would never see him again. I said OK and pulled my pants down to my ankles.He turned on the light and looked between my legs, he looked longer than I thought safe and closed my legs so he would look where he was going. As I was pulling up my pants I felt his hand on my thigh. I clenched my teeth and didn’t say anything. I didn’t know if it was because I needed the ride or this whole thing was turning me on a bit.As I was thinking about what to do his hand went right from my thigh to over my pussy and a moment later a finger was inside me. I don’t know why it felt so good so fast but it did. He moved his hand lower and drove his finger all the way in me. His hand was bigger than mine or my boyfriends and it felt great inside me, a moment later there was another finger inside me. I couldn’t help but start to moan and could feel myself getting very wet.He kept up his attack on my pussy till I was about to cum, I think he could tell from my breathing or something and pulled his fingers out of me. I was about to ask him why the hell he had stopped when he turned the inside light on again. I looked at him and then looked down and saw that he had somehow taken his dick out of his zipper- I guess he used his knee to drive—his dick was not completely out of his pants and I could see it was bigger than any other I had seen up to this point in my life. He asked me if I liked it, I told him I thought it was "OK" and didn’t want him to know how exciting his big cock looked to me. He said "why don’t you undo my pants and take it out for me." I couldn’t believe I was going along with all this, but at this point my horny little mind was winning out over any reason.I undid his pants and pushed his underwear down a little and then I could see the whole dick and I loved the size of it, just standing at attention like it was performing for me. He then asked me to suck it- actually he told me to suck it, which was something I like in a guy- just tell me don’t ask. I told him I would if he brought me home and if he turned the light out- he agreed to both and as the light went off I went down on him. As I was sucking his beautiful dick I felt his hand running down my back. I was so glad he was doing this as I needed his finger back inside me and that is right where it was heading. I felt his hand on my bare butt and then felt his finger slide back inside me. Immediately I felt myself getting wet again. I rewarded him by taking his dick further in my mouth. I then felt another finger in my pussy and felt I was back on my way to the climax that he cheated me out of a few minutes earlier. Then I felt something strange, he had taken on finger out and I felt it pushing against my butt hole. I lifted my head off his cock and said "wrong hole" with a little bit of a laugh. This isn’t the first time it had happened with a guy and the guy was usually so embarrassed that he jerked his hand away. But this guy responded with "no it’s not." And he pushed his finger inside my ass. I was surprised how easy it slid in and how it didn’t hurt. It actual felt good. He was fingering both my holes. I had never had anything but a thermometer in my ass, and I guess my pussy juice was enough of a lubricant for his finger. He then took the other finger out of my pussy and pushed it in my butt and then drove them both deeper. He commented "oh I guess someone takes it up the ass" I pulled off his dick and said "no way, I have never even been fingered up there." He told me he had been with a couple of girls whose butt was easy to enter, but usually it was much harder. As a finger would dry out he would run across my labia and get it wet and slide it back in my butt. I couldn’t believe it but I felt I was about to cum and his fingers weren’t even in my pussy.He asked me to look where we were and let me know if I lived near there- I couldn’t believe that this guy stopped me coming again. I sat up a bit and told him we were about a mile from house (I lived on the main road). He asked me if there was someplace to "park" I told him to go past my house and there was a research company building with a parking lot. As I was sitting up a bit his fingers were deeper inside me and I was really enjoying the anal attack. I went to go back down on him and he told me to wait till we got to the lot.A minute later we were there. He pulled over, turned his car off and said let’s get out. "get out?" I wanted to cum already and I wanted to take his load- I loved the taste of guys cum and was hoping that this big dick would have a big load. He told me to just slide to the end of the seat and he would come around to me. I did and I had my legs out of the door but was sitting on the seat. He came around with nothing on but his shirt. He then said "well this might not work the car light is on" he was right I thought he was going to lick me (I only have had 2 other guys do that and came with both of them.) He said ‘here get out…’ I slid my shoes back on and got out. He told me to suck his cock and I did- this time he was directing me and I loved it- he had me lick and suck his balls- I had never done that before and it was neat to feel his cock on my face as I was licking him. He then told me to lick his shaft all over. I was about to take him into my mouth when he told me to stand up. He told me to turn around "I want to see that ass in the moonlight." I turned around and he told me to bend over the hood of the car, which was nice and warm. He asked me if I wanted his fingers back in my hot ass and I told him "yes" I heard him spit and then his wet fingers (2 together) went right into my ass. He again asked if I had been fucked up the ass as I was letting him so easily and I told him "no." He then said something that changed my whole idea of being fucked at that young age. "You know I know a few girls that will only take it up the ass as they can’t get pregnant that way." Here I wanted to make it with my boyfriend but was scared of getting pregnant, condoms or not.The guy took his fingers out of me and I heard him spit again. I felt his fingers about to reenter me, no this was not his finger, I felt my hole spreading out much bigger than before and then he rammed his cock into my ass. I may not have had pain before but I did at that moment. I screamed out and he told me to relax. He held his position and didn’t move. Me on the other hand, I thought my legs were going to buckle. He reached around my leg and started to play with pussy with one hand and my tit with the other, never moving his cock. I guess my body started to accept his dick as the pain was being replaced with the pleasure from his hands and fingers. I learned never to let a guy ram me like that – that if a guy enters slowly you don’t have the reaction I had those first few minutes. Finally I (and I guess he did too) felt my ass relax and relax the grip I had on his cock. He started to pump me and took his hand away from my pussy. Even without him fingering me I started to feel really good between my legs and the felling was getting better with every thrust of his dick. I was felling a climax coming again and prayed that he wouldn’t stop this time. He didn’t and the next thing I knew, in the middle of outdoors I was moaning loudly with my first anal orgasm. My coming got him to quicken his pace and he was pumping his whole body into my butt. I could hear the slapping noise and the whole idea of being fucked in the ass was such a turn on that I kept cumming. I heard him say "here it comes" and I actually felt him shoot his load in my ass. I was disappointed that I couldn’t take his load in my mouth but the feeling I was experiencing was worth it. As he came his cock was more lubricated and the feeling in my ass got even better and I reached another climax. He pumped me for a few more moments and then pulled his dick out of my ass. I couldn’t even move for another minute or so and almost laughed that my legs felt frozen. All of a sudden I felt some of his cum run out of my ass and down toward my pussy. I stood up quickly as I didn’t think that was a good idea and put my hand between my cheeks and took the cum in my fingers. He was opening the back door and told me he had a towel. As his head was in the car I brought my hand to my noise- It smelled like sex and not something else that I had feared, and while he wasn’t looking I ran my fingers across my tongue and took a handful of his come into my mouth. He came out and I think caught me but never said anything. He gave me a towel and I cleaned up.We got back in the car and I had him drop me a few houses from my own so he wouldn’t know where I lived. He told me "I’ll look for you on the road" I told him he could pick me up anytime (we actually did hook up twice more over the next year)… and we parted without ever knowing each others name.I walked to my house and my ass felt funny and I wasn’t sure I was walking straight. Luckily my mom wasn’t waiting up for me.I got ready for bed and washed up a little extra. I got into bed and before long I was fingering myself as I was still turned on. I got up and got some Vaseline from the bathroom and started to use both hands – I had two fingers in my ass and two in my virgin pussy. I was about to cum and the fingers in my butt went in even deeper. I stopped and got up and got on the floor in front of the full length mirror on my door and watched myself attack my two holes I cam like crazy and was bucking on the floor. When I took my fingers out of my butt I couldn’t believe how big my hole was- I watched it with amazement as it went from this huge hole to its tight normal self in a mater of moments. I washed up again and went to bed. I laid there thinking how I was going to let my boyfriend fuck me, but not where he was thinking.