The first time it happened I was 12 years old. Mom and Dad had decided that I should go to an all girls school -- while my brother Bill was 18 and old enough to decide if he wanted to continue school or just go on to get a job. His grades had been pretty bad so he opted to go straight to work at the local mill.
Sometimes on the way to work, Bill would see me and give me a ride up to school. He'd stop, push open the door on his old Chevy Station Wagon and I'd climb in. He wouldn't say much to me. I was better in school than him and I think he was mad that Mom and Dad had made such a fuss over me.
This one particular day, I was walking to school when Bill pulled up alongside me and offered me his usual ride. I got in and we started along when I noticed the two cases of beer on the floor at my feet. From the looks of Bill, he had already had a few and was going to meet some friends to drink some more. It wasn't far to the school but I was scared shitless; I was afraid we were going to get hit or pulled over the police.
When the school came into view I was so relieved that I jumped out of the car before he came to a complete stop and went straight up to the playground. It was only after a couple of seconds that I realized I had left my schoolbooks and homework in the Station wagon. It was too late though, Bill had pulled away and I knew my teacher would be mad with me for not having the homework.
I remembered the sand pit where Bill and his buddies always hung out before going to work. I figured they were probably drinking their beers there so I cut through the woods behind the school and headed out to the sand pit.
Sure enough, when I got there, Bill was sitting around with his buddies. There were five of them in all. Bill, Ted, Tony, Edgar and a woman I didn't know. Ted was about Bill's age and was about the same grade average. Tony was 35 and was divorced from his wife whom he constantly complained about. Edgar was kind of a halfwit, he laughed at things no one else understood but he could put down more beer than anyone. And the strange woman looked quiet and brooding to me.
The minute I walked through the bushes, they all grabbed their beer bottles and hid them. When Bill saw it was me they relaxed and got angry with me for scaring the shit out of them.
"Jesus!" Bill yelled, "What the fuck are you doing, you scared the hell out of us!"
"Sorry Bill," I said, "I left my schoolbooks in the car. It's got my homework." They were almost finished with the second case of beer and none of them looked like they could walk a straight line to save their life. Bill gave me a strange look. He motioned me to come over. I walked slowly; ready to bolt if he decided to hit me. He didn't hit me often but when he did I usually ended up on the floor.
"Lemme see your uniform," he said, "Spin around."
All his friends were laughing and encouraging me to turn around so they could see my school uniform. I did a little pirouette so they could see my uniform from all sides. I couldn't figure out why they liked it so much. All it was, was a white cotton blouse under an argyle blue sweater and a plaid skirt. The skirt had red trim and ended at about knee level. My shoes were black flats and the socks were the same blue argyle as the sweater.
"Nice," said Tony. He looked at me like he was appraising a cut of steak.
"Your weird," I said, "This dress is ugly!"
"Then take it off," my brother said. He laughed and all his friends including the strange woman agreed with him that I should remove the dress.
"Fuck off!" I said, "You're a bunch of freaks!" At this point I stomped over to the Station Wagon to retrieve my books.
Bill's station wagon was old and the handles were rusted. The front passenger door couldn't be opened from the outside and the backseat door was permanently locked. It also had the window rolled up. Bill usually left the front seat passenger window open so I figured I could reach in and get my stuff. I could see it sitting on the middle of the bench seat but it meant pulling myself half way through the window to get it. I had barely reached it when I felt two hands pin my legs to the side of the car.
"Hey!" I said, "Let go of me!"
"Not until we make you pay for scarring us you little bitch!" said Bill.
I must have really pissed him off and his friends were helping him. I started screaming and crying while trying to break free. From the angle I was hanging at I had to keep one hand on the seat, otherwise the window frame would cut into my stomach. Whenever I reached back with a hand to hit them they merely pushed it away or held it.
I felt hands pull my legs apart so I was no longer standing on the ground. This forced me to use both hands to keep my balance and not let all the blood rush to my head. Another set of hands reached up under my skirt and flipped it over my back, exposing my panties.
I felt the hands grab my underwear and what felt like a knife was inserted under the material cutting through it. They removed the rags that had once been my underwear and I felt hands running all over my ass and pubic area.
"Stop it!" I screamed and cried but they only laughed and continued to pinch my butt cheeks and pull at my pubic hair.
Someone's finger started rubbing me between the folds of skin of my privates then I felt the lips being pride apart and a finger was force inside. At the same time someone else's finger poked into my butt hole and started pushing in and out. The fingers hurt and I cried and screamed at them to stop.
Then I felt my shoes and socks being removed and my legs were pulled farther apart while fingers continued to probe my anal cavity and pussy. I looked back to see Bill unzipping his fly cried in dismay when I saw his cock spring out like a fishing rod released from a bag.
The hands pulled my pussy lips wide open and suddenly I felt a larger flesh finger push its way into me. It hurt so much I thought I was going to die. I screamed and received a harsh slap in my butt cheeks.
"Shut the fuck up, you little shit!" Bill yelled. I could feel him continue to push his cock into me until he was buried to the hilt. I felt something inside of me rip and then I became slick inside. The pain grew worse as he continually push-pinned me to the car. All the time he continued with a forceful in out motion that dug deeper and deeper into my pussy.
Soon I felt a hot gushing sensation inside me that began to leak out of me and down the insides of my legs. Bill exhaled in great relief and pushed a few more times before pulling out and stepping back.
Then in disbelief I saw Tony step in behind me and he rammed his cock straight into me. The sudden burst inside of me caught me by surprise, it wasn't as painful as before but it evoked a scream from me anyway and I received another slap in my ass.
Tony repeated Bill's performance with the occasional slap on the ass for effect. I think he liked it cause whenever he'd hit my ass, I'd flinch and grip his cock with my pussy in reflex and he would moan with pleasure from the sensation. Then I felt the same hot gushing as before and more warm liquid oozed down my inner thighs.
When Tony pulled out, I watched as Ted stepped up to my ass. He looked at me with disapproval but took out his cock and pushed it into me anyway.
By now my eyes were streamed with tears and I was crying continually, unable to stop if I had wanted to. Between the pain and humiliation I was totally balling.
Ted however wasn't much for repeating the previous two performances. He removed himself after about four strokes in me and placed the tip of his cock against my asshole. I knew what was going to happen about one second before he pushed the head of his cock into my ass.
I screamed like bloody murder, the pain was excruciating and I released my arms so that my upper body could be pulled away from the opening of the window. It did nothing to help me get away but it took the tension off of my weakening arms and caused blood to start flowing towards my head.
Ted grappled with my hips until he had a straight line which my chest dropping to the car seat only helped improve. He forced himself the full length into my ass hole and just kept it buried there while listening to my tortured sobs.
"Please," I cried, "Stop it! It hurts so bad, please stop it!" I continued to cry while my eyes and nose filled up with fluids. Ted did the push and pull routine like Bill and Tony and then I felt his warm fluid run into my ass and flow towards me.
None of it leaked out until Ted pulled out and then a large gob of the white stuff ran down my ass, over my pussy and onto the car door.
I heard Edgar laugh and I grew horrified to think what that halfwit would do to me. I heard some shuffling behind me and felt one pair of hands replaced by another as Edgar's turn came due. He wet his thumb and middle finger and plunged them into my cunt and ass simultaneously.
With his free hand he reached into the car and started pulling my blouse out of my skirt. Once it was free he reached up underneath the blouse and unhooked my training- bra, which he pulled on so hard that it ripped free of my shoulders and left me with nothing on under the blouse.
When I tried to reach up and tuck in my shirt again, he pinched the skin between my ass and cunt, which hurt like hell. I screamed again and that fetched a firm hot slap on my ass. From the feel of the pain I was certain there would be a handprint.
I felt Edgar's hand snake past my hips in the window and fondle my small breasts while occasionally pinching the nipples (when he could find them) and grasping my breasts in his hands till they hurt. It was now that my body started to convulse and my legs started to jerk and twitch. Edgar started laughing and he forced his fingers deep inside me while running them back and forth like Bill and Tony had done with their cocks.
At this point I heard the woman tell Edgar "She's gonna have an orgasm, let me have my turn." I was horrified that this strange woman was letting this happen to another girl but that she was actively going to participate was unbelievable.
My legs were grabbed by two separate sets of hands and suddenly I was pulled as far apart as my legs could be spread. I felt a soft wet something touch my cunt lips and start rubbing around my opening. Suddenly teeth bit into my flesh and I howled with the pain through my sobs.
Then the tongue (which is what I know it was now) began moving around and my hips began to writhe and I grew warm inside. Suddenly my body convulsed and I felt my insides knot up and freeze as my thighs twitched and a great release of tension began deep inside my body. I realized that I was having first orgasm straight into some strange woman's face.
All this time, the blood had been rushing into my head. Sweat was pouring off of me in buckets and with the final release of my orgasm I couldn't handle it and passed out...
...I awoke later to discover I was alone with my dress up over my head amongst a pile of empty beer cans. I straightened myself out and wiped away the sticky mess built up on my inner thighs with the rags, which used to be my underwear and walked home. The bus had passed me on the way home so I knew that school had ended. Bill and his friends had left for work long before and I probably wasn't going see Bill again until late that night.
To wrap up the end of this story; Bill had threatened me, saying that he'd tell all my friends that I was a fucking slut.
I had tried to refuse future rides from him but he threatened with tell on me if I didn't. Most of the time he would drop me off at school and drive off but occasionally we'd drive right on by the school to the sand pit. Those were the days I hated the most.