My mother and father separated when my mother was till pregnant with me. Although she was still very much in love with my father she left him because he had had an affair and gotten another girl pregnant. My mother told me how he had begged her to stay, but she said she couldn’t stand the thoughts of him being with and making a baby with another woman. She left him and moved from Northern California to Southern Florida where she later gave birth to me.
My mother, Caroline, was only 4 months pregnant with me when she left. My father had told her that about the affair and that the girl was also 4 months pregnant.
My father flew to Florida when my mother called and told him that she had given birth to me. He loved me very much and didn’t want to leave, but he was in the middle of law school and just five days before I was born, the other woman had given birth to his son, my half brother, and he had to get back to California.
My brothers mom was nothing like my mother. She was a wild girl, who slept with my father on the first night she met him. He was drunk and depressed because he and my mother had been fighting over money. She found him in a moment of weakness and nine months later they had a child. She didn’t want to be a mother, so she left my brother with my father and disappeared.
I didn’t meet my brother until I was five years old when my father had finally gotten through law school and had landed a very well paying job. He sent for me and my mother and we went to California.
My father had been the one to name my brother. He named him after himself. My mother and him had always said they would name their child after my father, but my father figured that she wouldn’t because of everything that had happened, so he named his son after himself. Jessie is my brothers name and my mother, sticking to the plan to name me after my father named me Jessica.
When I met my brother he and I hit it off instantly. He was my best friend from the first time I met him. When it came time for my mother and I to leave everyone left with tears in their eyes. I didn’t want to leave my brother and I don’t think my mother wanted to leave my father.
After that I only got to see my brother during the summers. I would go and stay with my father all summer long. My mother never went back.
Jessie and I would always stay in touch with each other throughout the year. We would talk on the phone or e-mail each other.
When I was fifteen I had gotten a work permit and started working as a waitress at a local diner in Florida. I had to work through the summer so for two years I didn’t get to go to California to see my father and my brother.
It was about a week before my seventeenth birthday. I was sitting on my bed with my boyfriend Jason. He had been trying to talk me into the fucking him again. I liked Jason a lot, but I knew I didn’t want to have sex with him. Every time we would make out he would rub on me with his rough hands and he would kiss me so hard it almost hurt. It wasn’t pleasurable at all.
He had just put his hands up my skirt and was trying (unsuccessfully) to finger me. He wasn’t a virgin, but he still didn’t know what he was doing. He and I had messed around a lot, but I always stopped it before it got too far or when he did something that completely turned me off.
He had just reached my panties and was pulling them to the side to put his finger in my pussy (No rubbing my clit or anything first, just straight to the hole), when my phone rang. I pushed Jason off of me when I seen my brothers name on the caller ID.
“Hey, Jessie, I’m so glad to hear from you.” It was true, I was so glad he had called before I had to suffer through Jason trying to finger me.
“Hey Sis.” He sounded depressed. “What are you doing?”
“Me and Jason were just hanging out. What are you up to?”
Jessie had just got a new car and two days after he got it some old woman had rear ended him and his car had been in the shop every since.
“I was just sitting here. Dad is out of town. I haven’t seen you in two years. Everyone here is at work and I’m stuck in this damn big ass house unable to go anywhere.” He paused for a minute. “You aren’t going to be able to come and visit this summer are you?”
I felt a pang in my heart. I missed my brother so bad. He was my best friend in the whole world. I made my decision. I looked at Jason sitting next to me and decided I would have to include him too. “Jessie, I want you to call Daddy and tell him to get me and Jason a ticket. I will be there for your birthday. I have two days, so you better tell Dad to hurry.”
“Do you have to bring Jason?” Jessie loved me, but he hated the idea of me bringing my boyfriend with be, because he was afraid I would spend all my time with Jason instead of him. Jessie sighed. “I’m just kidding. I’ll call Dad and tell him to get you and Jason a ticket and a rental car so you will have a ride from the airport. I can’t wait to see you.”
Jason and I got off the plane and picked up the rental my father had provided for me. I couldn’t believe how fast my father had gotten everything together. It had only been two days since my phone conversation with Jessie and here I was pulling into the drive of my fathers house.
The house was huge. He had done well for himself since he finished law school. I always marveled at all the nice things my father had. The whole house was dark. It looked deserted. There were no cars in the drive way. Every light in the house was out. I had called Jessie and told him that I was on my way from the airport. It wasn’t like him to leave knowing I was on my way. I pushed my key in and unlocked the door. The lobby was so dark you couldn’t see a foot in front of you. I felt my way to the light switch and flipped it on.
“SURPRISE!!!” Several voices screamed at once.
I nearly jumped out of my skin. I looked up and everyone that I new in California was standing there and Jessie was in front of them all with a huge smile on his face. “Surprise Sis. Your birthday is in five days. I thought it would take longer for Dad to get you here, so when he got you a ticket for today I had to plan fast.”
I felt tears coming to my eyes. “But, Jessie, today is your birthday.” I ran over and hugged my brother. “Thank you and Happy Birthday. I love you.”
Jessie squeezed me tighter. “I love you too sis. Happy Birthday to you too.”
My father had spared no expense for my surprise party. Even though Jessie, me and almost all of our California friends were under the legal drinking age, my father had bought every kind of alcoholic beverage you could think of.
It was getting late. Everyone in at the party was pretty well wasted. Some had called cabs to come and pick them up, some had called their parents to pick them up. There were still plenty of people there though.
After the party got in full swing Jessie had disappeared with his girlfriend, Rachel. I didn’t even know he had a girlfriend until I got there. I was kind of annoyed at Jessie, because he could see this girl anytime he wanted, and I had come all the way from Florida to see him.
Jason and I were sitting on the couch in the den. He was kissing on my neck. He leaned over to my ear and whispered. “Where am I sleeping tonight?”
I smiled at myself. Jessie and I had already worked out the sleeping arrangements. I was going to sleep in my room. Jessie would sleep in the guest room, because it was being renovated. Jason was going to sleep in Jessie’s room. “You will be sleeping in my brothers room.”
Jason, smiled. “And where will you be sleeping tonight?”
I laughed a little. “I’ll be sleeping in my room.” I knew what Jason was getting at. I decided then and there that I was going to give in this time. I was going to lose my virginity tonight to Jason.
Jason shook his head. “Nope, we are going to sleep in the same room.” He stood up and leaned over and kissed me on the cheek. “I’m going to go to the restroom and I’ll meet you there. He walked off towards the steps that led upstairs to the bedrooms and the master bathroom.
I got up and decided I was going to find Jessie and tell him goodnight. I figured he wouldn’t notice Jason missing with all of the people here and Jason and I would be safe. I walked up the steps after looking for Jessie downstairs for over twenty minutes. I walked to the guest room and opened the door. The room was dark, but I could hear the tell tale signs of a couple having sex.
I heard Rachel panting and saying “Fuck me, harder, harder.” I knew it was Rachel, because Jason had made a comment earlier that evening that Rachel and I looked and sounded alike. I remembered hating the sound of her voice and hoping that I didn’t really sound like that. Hearing her panting while she was fucking my brother made me dislike her even more. I didn’t think she looked like me either. Even though she had long brown hair like me, her chest was about the same size as mine, and she was pretty much built exactly like me. I knew I looked better than her.
I closed the door and walked to my brothers room to meet Jason. I opened the door and the room was dark. I flipped the light on and decided that I would make this as easy as possible for Jason. I took off all of my clothes. I turned the light out and climbed into my brothers bed and couldn’t help but wonder how many girls he had had sex with in this bed. I was getting ready to lose my virginity in my brothers bed. I wondered what Jessie would say about that. I quickly pushed the thought out of my head. Thinking about my brother was a total turn off. Wasn’t it?
I must have fallen asleep because the next thing I know there is someone climbing in the bed with me. He jumped a little when he felt someone next to him. He put his arm around my waist and then pulled me close to him.
I rolled over and was met with a kiss. I couldn’t see because it was so dark. Jason kissed me differently than he ever had. He kissed me more gently. I could actually feel myself getting turned on by this. I had always hated kissing Jason before, but now he was doing a pretty damn good job.
He ran his hand from my waist and I felt him jump again when he realized that I didn’t have any panties on. He rubbed my ass and then ran his hands up to my breast. I moaned when he started caressing my left nipple.
I was in shock. I couldn’t believe how gentle he was being. Jason had always been so eager and fast that it turned me off. Now he was doing everything just right. He was taking his time and not slobbering all over me. He was kissing my neck now and he moved his hand from my breast to belly and kept caressing further and further down.
When he reached my pubic hair he pulled back a little. I grabbed him and pulled him back to me. I couldn’t believe Jason was actually waiting for me to give him the “ok” to go on. I had always had to make him stop before.
I was so turned on that I grabbed the waist line of Jason’s shorts. I thought it was kind of weird that he had on jean shorts now, because he had on basketball shorts earlier. He must have changed. I undid the button of his shorts and pushed them down. His cock sprang out of the hole in his boxers. Boxers? Jason had always worn briefs. Not the sexy ones either, he wore the ugly whites ones. He had went all out for me. I had begged him to wear boxers. He always wanted me to jack him off in his car and I never could really get a good grip on him because he always had on those stupid underwear.
I wrapped my hand around his cock and started stroking. Wow, it was bigger that I remembered it being. He must be really turned on. It seemed at least an inch longer and I could barely get my hand around it. Was that even possible? Maybe it was because he couldn’t really get fully exposed before because of his underwear.
Jason finally started rubbing my pussy. He was moving so slow and easy. Again I marveled at the care he was taking this time. He had never been so gentle before. Even his fingers felt soft where as they usually felt rough. He rubbed my pussy with his four fingers. Taking them all in a circular motion over my entire pussy. Then he let his middle finger fall into my slit. He slowly rubbed my clit in a circular motion, every now and them running his finger down to my hole. He never put a finger in my hole, just ran his finger over it to get it wet. Jason had never been able to find my clit before, but now he was teasing it with his fingers. Every other time he would just plunge his finger into my hole a couple of times before he would get off. Jason had never brought me to an orgasm, but right now he was bringing me closer and closer. I could feel it coming on.
I was holding Jason’s cock in my hand, but I wasn’t stroking it anymore. I was too lost in what he was going to me to be able to do anything for him. I found that strange too, because Jason had always been selfish before. Maybe he had realized why I wouldn’t ever have sex with him.
My thoughts were shattered when I felt a finger move ever so gently into my hole. He was moving in and out with his index and middle finger and he was using his thumb to rub my clit. It was too much. I decided then that I didn’t want to get off yet. I wanted him inside of me when I came. I grabbed his hand and pulled it out of me. I pulled him on top of me and I felt him hesitate. “It’s okay” I whispered. I didn’t even recognize my own voice it was so full of passion.
He slowly lowered himself on top of me. I took his cock and lined it up with my virgin hole. I felt him push and then hesitate. Only the head of his cock was inside of me and my pussy was adjusting to his size. I wrapped my hands around him and grabbed his ass and pulled on him and he pushed in a little farther. I felt him hit something inside and he gasped. I thrust myself forward and forced his cock into my pussy the rest of the way. Tearing through my hymen. It hurt, but it also felt so amazing that I had to have more. He was very still now. He didn’t move. I was under him pushing my hips up to his, forcing him inside of me. Finally, as if he couldn’t stand it anymore, he started thrusting with me.
We were perfect. Our rhythem was identical and we were meeting each others thrusts. In and out he went and I could feel his big cock getting harder against the tight walls of my pussy. I knew I was going to cum, and I wanted him to cum with me. I squeezed my walls as tight as I could and I felt him loose all control. He exploded inside of me and I exploded on him. My whole body was shaking and I didn’t want it to stop. He kept thrusting at our same rhythm. I could feel his cock getting softer with each thrust and finally it slit all the way out with his retreat. He collapsed on top of me. He head…
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