Amanda's Highschool Lover

by Angelgirl

Caution: This Sex Story contains strong sexual content, including Ma/Fa, Teenagers, Rape, Drunk/Drugged, Heterosexual, BDSM, Sadistic, Gang Bang, Fisting, Bestiality, Enema, Violent, .

Desc: Sex Story: Amanda's first high-school date turns into a night of torment and gang rape.

[Book4]


This story begins three years after I met Billy and his Daddy. My life has completely changed since then. I still see Billy on occasion but his father died two years ago. I think I'm getting a little too old for him now; I'm fourteen, and Billy likes girls that are just starting puberty, like I was the first time they abducted me. My relationship with my daddy has improved 100% also; I finally know how to give him pleasure. But that's another story. That's why I found it so strange when my daddy started talking about one of the boys from my school. I should have known from the beginning there was something wrong. My father has always claimed me as his private possession. Now he seemed to be directing me towards the boy. He told me that I should have friends. He said he knew Raymond and considered him a very nice young man. I should have known it was too good to be true. Anyway, here's the story.


All week long I could think of nothing except Friday night. It was going to be the first school dance of the year and I would finally get my chance to meet Raymond. I was a freshman at St. Mary's High School and Raymond was in his senior year. If I hadn't chosen to sit in the schools gym during lunch breaks I never would have met him. I would sit high up in the bleachers so I wouldn't be disturbed by other children. I didn't have much use for children my own age, as I considered myself far to mature to associate with them.

I had been eating in the gym for about three weeks not paying much attention to the other kids in it. Then one afternoon things changed. I was sitting high in the bleachers as usual, when I heard a loud crash over my head. I dropped my sandwich and pop spilling it onto the floor. I saw a basketball bouncing back towards the gym floor. There was a young guy standing at the edge of the gym looking up at me.

"I just wanted to know if you were alive or not," he laughed loudly.

"You fucking Ass Hole," I yelled back at him. "You made me spill my pop."

He just laughed louder as I displayed my little temper tantrum. I couldn't stop myself from looking back at him as I got up to leave; he seemed to stand out from everyone. I could feel his eyes burning into me as I walked towards the exit. It felt like I was walking in slow motion. His white shorts fit tight as skin on his muscular legs and his narrow waste expanded into a beautiful chest with wide shoulders. His blue eyes seemed to sparkle like diamonds. His broad smile was almost impossible to turn away from. His hair flowed across his forehead in waves of pure gold. As I reached the exit I was unable to turn away from his hypnotic smile. I could feel tingling throughout my body and a wetness between my legs. I stood like a statue staring back at him. He started to laugh. It was like he knew what he was doing to me as he turned and walked away; but still I couldn't take my eyes off of him. He had the most beautiful body I had ever seen. I heard laughter coming from a bunch of boys sitting on the other side of the gym; they had been watching me the entire time. My cheeks began to redden with embarrassment. I knew they had seen his effect on me. I turned quickly to leave but in my haste I bumped into another girl. She looked to be about seventeen years old.

"His name is Ray Richards," she said to me. "I'd stay away from him if I was you. He's a real prick."

"What do you mean?" I asked trying to hide my excitement and obvious interest in him.

"He's broken a lot of hearts in the time he's been here. Let's just say he likes to play rough. Stay away from him. Hurting people is what he does best"

The girl turned and ran out of the gym. I could see she had tears in her eyes. It was obvious she was talking from experience. I looked back towards the gym only to see that Ray and his friends had left.

That night as I lay in bed I couldn't get the image of Ray's muscular body out of my mind. It was almost midnight and I was still awake. I could feel the wetness between my legs as I touched my fingers to my vulva; it was puffy and wet. I opened my legs and placed a pillow over my swollen cunt. I squeezed my legs around it pulling it into me. I could feel its pressure on my clit. It wasn't long before I was erupting in a beautiful orgasm. The pillow was soaked from my juices. I couldn't believe that a boy was having this effect on me. He couldn't have been much more than eighteen years old. For some reason I couldn't get him out of my mind.

Later that night when my father came to visit me I told him what happened in school and the effect it had on me. I expected him to be enraged with me. I even anticipated him beating me when he found out I had masturbated. My father asked me the boy's name. I told him that it was Ray Richards. I was surprised to see a smile appear on his face when I told him the name. He said that he knew the boy. He said he met Ray several times at a friend's home. He said I should pursue a relationship if I wanted. After my daddy left I was so happy I couldn't sleep the rest of the night thinking about Ray and what he might be like.

Over the next two weeks I saw Ray in the gym almost every day, but neither he nor his friends acted as if they saw me. I started sitting closer to the court each day until I was just one row up. It was Friday, the day of the school dance. I could hear Ray and his friends laughing. I heard Ray saying that he wasn't taking anyone to the dance.

"All the girls in the school are too immature for me," I heard him saying.

Ray had no idea how wrong that statement was. I hadn't been a virgin since I was ten years old. I wanted to tell him. I couldn't understand what it was about him that excited me so much. All I knew was that I wanted his attention more than anything. I lifted my legs onto the seat in front of me. I was wearing a short skirt. I knew that if Ray looked my way he would be able to see my panties. I could feel my heart pounding wildly. I had to make him notice me; the dance was tonight. I looked down into the book on my lap, but I wasn't reading it. Out of the corner of my eye I was watching Ray. I could see his friends laughing amongst themselves as they pointed in my direction. Ray had his back to me. He was the only one not to see my wanton act. I dropped my eyes back into my book. I felt like such a fool for what I had just done. I lowered my legs and was about to leave when I heard a voice.

"Are you going to the dance tonight?" The strong masculine voice asked.

He seemed to have appeared from nowhere. I hadn't seen him come over to me. He was standing in the aisle just a few feet in front of me. As I looked up from my book I could see his thick legs just a few inches from my face. They were covered in fine blond hair. I gasped when my eyes rose to his crotch and saw the bulge of what looked like a very large penis trying to push its way out of his tight shorts. I had to stop my hand from reaching out to touch it. My body wanted him so badly that I was losing control of myself. I was sure he thought me a little virgin ripe for the taking. He had no way of knowing what I had been through. I was going to enjoy playing the innocent girl for him. If he knew how badly I wanted his affection I'm sure I would have scared him away.

"I might be going," I said smiling up into his face, not really wanting to look away from his swelling crotch.

"I read the story you wrote for your literature class," he said with a smirk. "I loved it. I think it was the wildest thing I ever read. I have wanted to meet you ever since. You must be a very interesting girl. I would love it if you would save a dance for me." He said as he turned back towards his friends.

I was in shock; "How did he read that story. I got in so much trouble for writing it that I had to see the school psychologist for months after. The teacher flipped when she read it." I thought to myself as a cold chill ran its fingers up my spine.

We were told to be creative; she said the more creative and original our stories were the better our marks would be. I decided to write a story about someone I had been infatuated with most of my life. I wrote about the "Marquis de Sade". In 1772 he used Spanish fly to drug two girls so that he could have his way with them. I thought it would be a wonderful story. The experience taught me a very important lesson about life. I could never let anyone know the things that were in my mind. Somehow Ray must have gotten a copy of my story. My father said he knew Ray, could he have possibly given a copy to him. I felt both ashamed and proud at the same time. Knowing that he had seen my story and was still interested in me excited me terribly.

"If after reading my story he is interested in me there must be more to him than just a beautiful body," I chuckled to myself. "I can't wait to find out what he is really like."

I had just stepped out of the shower and was drying my body when I caught my reflection in the mirror. I remembered the first time I had seen a woman looking back in the reflection. It had been almost four years ago now, when I was ten years old. It was the first time I had been with Bobby and his father. It was the day I had lost my virginity and almost my life. When I stepped out of the shower that day it was the first time I saw a woman looking back at me. My pussy was swollen and red from the abuse it had received. My breasts were covered in teeth marks, and my nipples looked huge. As my mind wandered to thoughts of Ray's cock again, I could feel the lips of my freshly shaved pussy filling with blood. I looked quite different now. My hips were wider and my waist seemed narrower. My breasts had growing to a respectable 36C cup. My curly auburn hair was almost down to my waist. I still weighed a hundred pounds soaking wet and I was just over five feet tall. I wondered if my plan to play the naive virgin for Ray was still a good idea now that I knew he had read my story.

"Just because I wrote a story about rape, drugs, and promiscuity doesn't mean that I am that kind of girl," I laughed to myself. "I am going to play the little virgin to the hilt. I am going to have so much fun watching Ray try to seduce me. The only thing I know for sure is he will probably succeed."

I placed small dabs of "Tommy Girl" around my breasts and the outer lips of my pussy. It was twitching wildly with anticipation. I finally understood what it was that excited me so much about Ray. He had a strong masculine body, but he was a boy. I was sure that I would be able to control him. The thought of making him plead for what he wanted really turned me on. I would drive him crazy before I would let him have me. I decided to wear the most erotic underwear I had. I slipped into a pair of red crotch less panties and a red silk bra that almost pushed my breasts out of it. Next I squeezed my body into my dress. It was a long tight fitting black dress. It plunged indecently low in the front. With my breasts bulging from my bra and my dress cut so low it looked like they were going to burst out at any moment. The long skirt was slit up the sides almost to my waist. It looked more like a long native loincloth that a skirt. It would split open revealing my legs all the way to my panties. I thought I looked extremely sexy as I spun around in front of the mirror.

"I think I am ready to drive Ray crazy," I smiled to my reflection.

"I see that you are ready to go to the dance," my father's voice boomed from behind me.

I turned to see him staring lustfully down on me. From the look in his eyes I wondered if I was going anywhere. But again he surprised me.

"I couldn't let you go without having one more look at you; you look so beautiful tonight. I want you to enjoy all the fruits of your womanhood. It will give me such pleasure imagining what is happening with you. Something tells me you are in for the experience of a lifetime. You will be a different woman. Now go to your young man and make me proud of you." He said in a rather strange way.

I didn't arrive at the dance until eleven p.m. as I didn't want to spend time socializing. The gym was packed with people. They all looked like children to me. Many of them were sitting in the bleachers necking. Hardly anyone was dancing. Maybe I had made a mistake coming so late. I wondered if Ray had already found someone else, then I felt something brush against me.

"May I have this dance with the most beautiful girl in the room?" The voice said.

I would have recognized his voice anywhere. I turned to see his outstretched hand waiting to take mine. He pulled me tightly into his arms. I could feel my breasts pushing against his chest. As the dance ended he gave me a little spin. My skirt flew into the air splitting wide open and his eyes widened as my body revealed itself to him. He pulled me back into his arms and began to tell me how beautiful I was. He said he loved the smell of my hair.

"That is the sexiest dress I have ever seen. You are absolutely beautiful in it." He said to me.

He was getting braver; trying to see just how far I would let him go. During the next dance I turned my body a little sideways to his. My hip fit perfectly between his legs. I began pushing it into his crotch; I could feel his manhood reacting.

"I could use a little fresh air," he said as the dance ended. "Would you take a walk outside with me?"

I felt so pleased with myself. I knew that my plan to drive him crazy was working. He led me to a bench that was fairly secluded. Ray lit a cigarette and asked me if I would like one. I told him that I didn't smoke. He put his hand into his inside pocket and pulled out a small bottle. He put it to his mouth and then offered it to me. I didn't really feel like drinking. The fact was I didn't need any booze. I could already feel the wetness between my legs, but if I was going to play the innocent virgin I would need to pretend that he was getting me drunk. I put the bottle to my lips. I was expecting the sharp taste of whiskey. I was greeted by a sweet pleasant flavour. I had planned on taking a small sip of the liquid, but I found myself drinking down two large gulps before I handed it back to him.

"What was that?" I asked as I felt warmth throughout my body.

"It's my secret recipe," he said as he smiled down at me. "I call it, "Panty Remover"."

I was a little surprised to hear him speaking like that; I didn't think he would be so bold. I decided to play along with him.

"Well then, you had better give me more," I said giggling like a schoolgirl.

I put the bottle to my lips and took a sip. Just as I was about to bring it down I felt Ray's hand over mine.

"If I am to have my way with you, you will have to drinking more than that," I heard him say rather coldly.

I could have pushed his hand away, but for some reason I enjoyed him acting forcefully with me. After all it was what I wanted him to do. He held the bottle to my lips until I drank three more gulps from it. I knew that I could drink quite a lot of alcohol before it would have much effect on me, but for some reason I was starting to feel light-headed after just a few sips. I felt relaxed, almost heavy feeling. I felt Ray's arms going around me, pulling me into him. His body felt hot and hard. I could hear his heart pounding. He eased my head back and placed his mouth over mine. His tongue rushed past my lips. It felt longer and hotter then any I had ever felt before. I wondered why I was experiencing such weird sensations. It felt like his mouth was smothering me. I could feel his hands on my breasts. Hands were on my knees spreading my legs apart, and another hand was sliding up my leg spreading my panties to one side as its fingers pushed into me.

"Holy fuck. Is she ever hot!" I heard a voice I didn't recognize say.

The sound of the strangers' voice shocked me back into reality. It was impossible for Ray to be touching me in so many places at the same time. My eyes didn't want to focus. I could tell that there were several forms lurking around me. I knew that they must be Ray's friends. I was about to scream when I heard Ray talk.

"All right guys, back off. She's my date. She'll need a lot more to drink before she is ready. So just back off before she gets too frightened. "He said to them.

I didn't really understand his words, I just knew he was mad at them for touching me and it made me feel a little more at ease when I felt the hands leaving my body. I was happy that Ray was protecting me.

"You are the sexiest girl I have ever known. When I read your story I knew I had to have you. You can't imagine how badly I have wanted you. I even asked your dad about you. He said you were perfect for me. Tonight my torment will end; tonight you are mine. I have never wanted someone as badly as I want you."

His words were melting my heart. If I had any fears they were gone now. I felt like my body was turning to molten lava. A fire was burning inside me like never before. He seemed to know all my weaknesses, my needs for love, affection. I didn't even mind when I felt the hands returning to my body. My legs were being spread again. I knew that it wasn't Ray's fingers that were trying to push into me. My head was being pulled back again and the coolness of the bottle pressed against my lips. It was held there until I drank several large gulps.

"That should be enough," I heard Ray's voice say." The slut should be ready now. Her daddy says she likes it rough; is everybody ready to give the cunt what she wants?"

I heard a roar of approval erupt from the other boys. I tried to understand what he was saying. My daddy would never say that. "He must just be trying to impress the other boys." I thought to myself as it nevertheless upset me a little.

"Get the car, and make sure no one sees you." Ray was telling someone.

I felt like a rag doll. I didn't have any strength in my body. I tried to speak, but I couldn't move my jaw. Even my eyes seemed hard to control. I should have been frightened, but instead I felt totally at ease. The words Ray had spoken just a few minutes earlier had completely vanished from my mind, I felt wonderful, and it was like I was on a cloud. I could feel hands touching my body again. A hand was pushing into my pussy; it was being very rough. It was pushing so hard that my bum was sliding on the bench. I wondered why it wasn't hurting. I was sure that he was trying to shove his entire fist into me. I could hear grunting as he trust his hand toward. Instead of hurting, it felt wonderful. I was even trying to spread my legs as I heard a car pulling up. Arms wrapped themselves around me lifting me to my feet. I couldn't move a muscle; I was totally limp. Ray must have put something into the drink. I was fully conscious, but I had no control over my body. They carried me into the front seat of the car. Ray got in behind the wheel. Another boy got in on the other side of me. I could hear others climbing into the back seat. I figured there were three boys in the back. I should have been terrified at what was happening but I felt no fear. I could feel wetness between my legs. The thought of five boys lusting after me was really turning me on. I was sure the worst that could happen would be they would all fuck me. I was sure that I wasn't going to be hurt. They were just a bunch of guys about to gang- bang a drunken schoolmate. The thought of being fucked by all of them really excited me. I had fascinated many times about having several men at the same time. I had imagined it as the ultimate form of attention as they would all be trying to give me pleasure. I had no idea just how wrong I was. A boy in the back seat stood up leaning over me. I felt someone pushing his fingers under my bra. He grabbed onto it pulling it over my head. The straps were snapping as he ripped it from my body. The large strap around my chest was the last to go. It felt like it was ripping my flesh as it shredded from my body. The boy beside me started to join in. They were pulling at my clothes from all sides; the fabric ripping and shredding from my body. It just a few seconds I was naked. I tried to cover my nakedness with my hands, but I was still unable to move. I was at their mercy. They were laughing as if they had all gone mad.

"Pull her into the back seat," I heard a voice yelling.

Two the boys from the back grabbed me under my arms and began to pull me over the seat. My spine felt like it was going to break as they pulled me over the back of the seat. They stopped when my bum was rocking on the top of the seat. Ray grabbed my left ankle and pulled it across his chest till it went out the drivers' door window. The boy in the passenger seat spread my other leg so that my right foot was out the passenger door window. I felt the windows being shut on my ankles and screamed in agony as I thought they were cutting off my feet. My head was lying on the lap of one of the boys in the back seat. He leaned forward and began biting my nipples. The pain was unbelievable, I tried to move but couldn't. I felt the boy from the front passenger seat leaning over me. His face was just a few inches from my pussy and I could feel his fingers pushing into me.

"Are you ever fucking wet. You really want this don't you? Your cunt is on fire," he yelled at me.

He was right. Just a few moments earlier I had thought I might enjoy their attention. I was sure that they would not hurt me, but now all my clothes were in shreds. My breasts were bleeding from being bitten so hard and my ankles were squashed in the window. The boy in the front seat was trying to force his entire fist into me. I heard a scream burst from my chest as his fist drove into the depths of my body, smashing against my uterus. There were stars flashing all around me. Their laughter seemed to be disappearing. I was in a dark place, [for a moment]. I woke up to the sound of my teeth chattering. I was lying on cold concrete.

"The cunts awake!" I heard someone laughing.

There were legs all around me. The next thing I knew a foot buried itself in my tummy. I groaned loudly as I rolled backwards still unable to move. The drug must have been wearing off a little because I could see better now. All five of the boys were standing in a circle looking at me lying on my back with my legs and arms spread wide apart. The boys began laughing and kicking me. I couldn't do anything to protect myself. I just laid there feeling the pain from their kicks.

"Don't hit any of the good parts until we are finished with her," I heard Ray's voice yelling. "Hold the slut down."

Two of the boys held my arms while another two grabbed onto my ankles. A stabbing pain shot through my body when they grabbed onto my ankles, it really felt like they were broken. I wondered why Ray wanted me held down. I was totally unable to move. I guessed it just made him feel more powerful. I saw Ray removing his pants. His cock jumped to attention as they dropped to the ground. His penis looked huge as it swayed over me. Before I could blink my eyes he dropped onto me driving its full-length into me. My insides were really hurting; the fist had damaged something in me. Ray's long cock was filling me with pain. I had anticipated this moment for so long. I wanted him so badly; I thought it would be beautiful. Now, all I could feel was pain. Terrible pain.

"Look! The cunt is crying," one of the boys shouted, seeming to make Ray thrust his cock into me even harder.

"Oh fuck, is she ever hot," Ray yelled as I felt his hot sperm filling my insides.

I heard him telling the other boys that I was all theirs. They seemed to go wild. They were like a pack of wolves during a feeding frenzy. They started fighting, trying to decide who would be next. After what seemed an eternity of listening to them yelling at each other they turned towards me lifting my limp body throwing it over a small steel table. I was lying on my belly with my head and legs hanging over the ends. They spread my legs apart and tied my ankles to the legs of the table. They tied my wrists to the other side of the table. I felt a stabbing pain in my anus as someone was beginning to shove his cock into it. It felt like I was splitting wide open. I tried to scream but only a whimper came from my lungs. Someone was pulling my hair, trying to lift my head. He began to push his cock into my mouth.

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