I got the chance to teach my little sister about sex and it started like a sex joke I heard as a kid.
The publishing rules say that everyone in these stories has to be at least 16 so even though the story is totally fiction, everyone in it is at least 16. Enjoy.
One of my favorite sex jokes is one we probably all heard when we were kids.
Little Debbie came skipping into the kitchen with a shinny new quarter in her hand. Her school uniform skirt swaying around her, she showed it to her mother. "Debbie, where did you get the quarter?" "Billy said he would give it to me if I climbed the tree," Debbie answered. Mom replied, "Don't you know he only wanted to see your panties?" "Yes Mom, so I fooled him. I took them off."
Here's how it really happened with me.
I was lying on my bed playing a video game when my (16)-year-old sister, Joan skipped into my room. She is three years younger than me but we have always gotten along well. She waved a five-dollar bill in the air and danced around a little. You could tell that she was happy. "Where'd you get that?" I asked. Donny, Frank and Jim gave it to me. They said that if I would take my panties off and show them my bottom they would give me five dollars."
I told her that she needed to be really careful because she and her friends were getting to the age where, especially guys start to be really interested in sex and she could get into a lot of trouble if she let them do too much. "You don't want to do anything that would get you a bad reputation and you sure don't want to get pregnant." Over the last couple of months Joan had started asking me questions and I had answered most of them for her. Then I jokingly said that I would give five dollars to see her cute little bottom too. Before I could stop her, she had her panties down and her skirt up to her waist. "Give me the five dollars." Then she dropped her skirt. I could feel my cock stirring even though my sister should not have that effect on me. She was a cute and sexy young woman. She was even starting to get boobs and I couldn't help but look.
I sat her down on the edge of my bed and talked to her more about sex and the act of having sex. We didn't have a dad and Mom had not had 'the talk' with Joan yet so I took it on myself to educate her more than the school had. We talked for some time. I could feel my dick getting even harder. Without thinking about what I was saying I said, "Hell Sis, I'd give you ten dollars to be able to touch your pussy. "Deal, pay up. That's fifteen bucks now." I started to back out but decided not to. "That's not for just once. You would have to let me do it any time I want for the rest of the month." There were three weeks left in the month. I thought that would make her chicken out. "Deal. Pay up."
She pulled her skirt up and spread her legs. I looked between her legs. Her tight little lips looked like a closed clamshell. I wasn't a virgin. My girlfriend let me suck and rub her tits and finger her pussy any time I want but we had only had sex three times. I reached over and rubbed my palm over the outside of my sister's pussy. After a couple of minutes I told her that she had better go now. She went to her room. I promptly shut my door, took my aching cock out and masturbated till I blew my load all over my chest.
The next afternoon, after school I took Betty, my girlfriend into the woods and fucked her twice. She didn't really want to but I was so excited that I would not take no for an answer. She finally let me.
After supper Joan came into my room. "Today Donny, Frank and Jim told me that they would give me ten dollars if I would give them a blowjob. I said no and came home. What's a blowjob?" I told her that it was another name for oral sex. I had told her that a man putting his penis into her and moving it in and out was fucking. She said that she had also learned that in sex ed at school. Now I told her that oral sex, or a blowjob, was the same thing but in her mouth rather than in her pussy. I told her that some people do that because the girl can't get pregnant and that I heard President Clinton on TV saying that oral sex was not sex. "I want to try it," Joan said reaching for my pants. I stopped her and told her no, but that I did want to rub her pussy again. She jumped out of her jeans and up on the bed. Again I put my palm on her crotch and rubbed. This time I slipped a finger between her pussy lips and rubbed across her hole and clit. My sister moaned and jumped a little. "Oh Paul, that feels nice. Don't stop." After a couple of minutes she started to breathe hard and I stopped. "No, don't stop. I really like it." I told her that if she really wanted to try putting my cock in her mouth that she could do it for just a little bit.
Her response was, "Yippy, take it out." I had trouble getting my six inches out from my jeans and under pants because it was so hard. Betty had never sucked my cock so this was going to be the first time for me too. I had watched a couple of adult movies so I knew what to do. I told Joan to open her mouth and put as much of my cock in her mouth as she could, then suck hard on it and move her head up and down on it. When her lips first touched I she stopped and told me that the end was wet and tasted salty. I told her that that was ok and to just do what I told her. She did just like I said and it felt wonderful. After a minute I could tell that I was about to come so I told her to stop. Joan took her mouth off my manhood and told me that that was fun but her jaw was starting to hurt. She asked me if we could do it again and I told her yes but not right now. I also told her not to do it with anybody else. She said ok. She left the room and I quickly jerked off again to relive the pain in my throbbing cock.
About fifteen minutes Joan stuck her head in my door and said, "Paul, I want you to be the first one to fuck me." Then she quickly left.
Several days went by. I spent a lot of time thinking about my sister wanting me to be the first to fuck her. I knew it was wrong but I also knew that I wanted to do it. Joan and I were alone at home in the living room and Mom would not be home for a couple of hours when she said, "it's been days from when you last rubbed my pussy. Don't you want to do it any more? Don't you like it? There's still a couple of weeks left in the month." "Come over here and I'll show you that I like it." Before she got across the room to me she had her pants and panties off. She jumped up in my lap, took my hand and put it between her legs. I rubbed between her pussy lips and this time I pushed my finger into her opening and finger fucked her. When she started to breath hard I did not stop. I kept it up till she had her first orgasm. "Wow, that was really something. I thought I was gonna bust. I want to suck on you again." I said sure and this time I dropped my pants to the ground. She looked at and played with my balls and cock for a couple of minutes, flopping it around and stroking her hand up and down on it. Then she leaned down and put it in her mouth and started sucking it the way I had showed her before. It wasn't long before I could tell that I was close to coming. I had told her about the stuff that came out of a man's cock and into the woman to make babies. She had also heard that in class at school. I asked her if she wanted to see it and she said yes. So when I was ready to come, I pulled her head off me and squirted my cum all over her shirt covered chest. "Wow, there was a lot of that stuff," she said. "You'd better go wash that shirt." Ya. I think so." and she pulled her shirt off. She wasn'y wearing a bra. It was the first time I had seen my sister's B-cup tits. I stopped her and sucked on them before I let her go. "That felt nice, Paul. Thanks."
The next couple of days we did not get any time alone. I snuck a few feels of her tits when nobody was looking and she got one good grab of my cock in my pants which was almost always hard around her now. I admit that I was not paying the attention that I should to my girlfriend and Betty was feeling put out about it but I was spending all my time thinking about my sexy little sister.
Saturday night Mom's friends had invited her out to a wedding shower. I begged off the movies with Betty, telling her that I did not feel well. After Mom left I took joan by the hand and led her to my room. "I want to show you something new tonight." "Neat. What." "Take your clothes off and get on the bed." Joan was undressed before me. I got on the bed and started licking her nipples. Soon I started working my way down over her tummy till I got to her hairless mound. I slipped my tongue between her cunt lips and started licking. Right away she started moaning and wiggling. Next I told her to get on top facing my feet. I pulled her pussy to my face and told her to suck my cock at the same time. "This position is called 69." I ate her thru two orgasms and she got my face soaking wet. Finally she had me ready to come. I told her to stop and jack me off till I came but she didn't stop. She sucked me till I shot in her mouth. She gagged and sputtered a little but worked thru it and swallowed my load. It was the strongest feeling orgasm I had ever had. I moaned and tried to shove myself down her throat.
"Joannie, next time, I want to put my cock in you and fuck you." "I've been waiting for you to say that. I want you to do it, really bad. I want your cock in my .... cunt." I talked to her about the first time and how it often hurt when a girl got her cherry broken and how she would probably bleed some. I told her that if she did not want me to hurt her she could do it herself with something like a broomstick or something. "No Paul, I want you to do it. I want you to take my cherry." She kissed me long and hard on the lips.
Several days later Betty told me that we were over. I apologized and begged her not to leave me. "I'm going to be with Steve. He'll pay attention to me." When I got home, there was Joan, naked and watching my porn tape in the VCR. "Where's Mom?" "At Aunt Sue's. Today's the day. I want you to fuck me now. BUT the month is over. Are you going to pay me again to play with me?" She laughed. I grabbed her and kissed her hard, slipping my tongue into her mouth and enjoying her sucking on it. "Let's do it in Mom's bed." "Ok but we need to put a towel down in case you bleed." We got into Mom's room and I started to unbuckle my pants. "I want to do that," Loan said and she slowly undressed me. She got on her knees to pull my pants down and when I popped out she sucked me into her mouth. It didn't get me any harder because I was already as hard as I could get. She jumped up on the bed. "Now. Do it now!"
I put on a condom and got between my sister's legs and reached between her legs to rub her and get her wet but she was already soaking wet. "Do we have to use that?" "Yes." I lined my cockhead up to the opening to her hole and started slowly and gently started to work my cock into her tight love tunnel. "Do it now. Fuck me hard, now." She put her hands on my ass cheeks and pulled me toward her. I understood what she wanted so with one thrust I buried myself balls deep in my sister. "Aggghhh !" It was almost a scream but not quite. "Fuck me Paul." I started pumping my cock into her, slowly at first and then faster and harder. Joan gritted her teeth and closed her eyes. Soon her eyes were open and she was thrusting back at me. I could feel that I was close to coming but I held back as best I could and I was able to get her to come before I did. "I love you Paul and you're my best friend." I love you too, Sis."
We found time to fuck four more times over the next couple of weeks and now I first ate her till she came first, then we fucked till I was ready to come and she would take the condom off and suck me as I came. One time I didn't get out soon enough and I filled the condom. She took it and pushed the cum out of it into her mouth, showed me her mouth full and then swallowed my load. Neither of us liked the idea of using the condom so I said I would see if I could find a way to get her the pill. Our school had just started giving them to high school girls. We were one of the first in the country to do it. But there was no way they were going to give them to an eleven year old.
I came up with a plan that I thought might work. I went to the nurse and told her that my girlfriend was at a different school that did not give out the pill and that we did not want to use condoms. She asked me if we were already having sex and I said yes. Ms. Green looked at me for some time and then told me that she might be able to take care of me. She paused and said "If you're willing to take care of me." She locked her office door and started to take her blouse off. Then I knew what she wanted. Ms. Green was about forty, 5'6" and weighed around 160#. She was almost flat chested. But, at lease she wasn't ugly. She slipped off her skirt and panties and stood there in just her nurses shoes with a big bush of pussy hair between her legs. She was wearing a wedding ring. "Well, get undressed."
She leaned over her desk. "Fuck me from the back. You don't need to use a condom." I had seen it on the VCR tape so I knew what she wanted. I got behind her and she spread her ass cheeks. I shoved into her. She wasn't very tight. Not like Betty or my sister. I fucked her for several minutes. "Get your finger wet and shove it in my ass." That was gross but I licked my finger and did what I needed to do. When I did, she came. Her cum was dripping off my cock. Ms. Green spun around and dropped to her knees and cocksucked me till I came in her mouth. We got dressed and she gave me the box of pills. "Each month when you get a new box, this is how you will pay me for them." I nodded my head. She told me to tell my girlfriend to take one every day and that we should still use the condoms till the first box was gone.
I gave Joan the pills and told her what Ms. Green had said but I did not tell her about having to fuck the nurse. I actually ended up enjoying it although I would not have thought of it on my own. We found times to fuck one more time that month and go 69 twice. Finally the end of the box of pills came. I went to Ms. Green and got another box. Like she had said, she expected me to fuck her again. This time she wanted me to put two fingers in her ass right as soon as I started fucking her and to pump them in and out the whole time and spit on them to keep them wet.
That night Mom was home but we could not wait for the first time we could have sex without a condom. We told Mom we were going to the school to watch a ball game but we took off into the woods. We got to a grassy clearing that I knew deep in the woods and I grabbed Loan and kissed. I had brought a blanket and I threw it down. We dropped down and wrestled each other’s clothes off. There was no foreplay today. We fucked hard and fast till I shot a huge load deep into my sister's hot, tight cunt. It did feel better without the condom. "Paul, I love the feeling of your wet cum filling me. She sucked me clean and we lay on the blanket hugging and rubbing each other. Before long I was getting hard again. I had her get on her knees and fucked her doggie style like Ms. Green had had me do to her. It was a great position with Joan, who was so much tighter than the school nurse. I could hear my cock making squishing noises in her cunt as it already had a load of cum in it, but it was wonderful. Soon I came again and Joan cleaned me again. We redressed and went home. We held hands till we got to where people could see us. When we got home she whispered to me that she had to get those panties off and washed. They were soaking wet.
We found one way or another to be alone and fuck. I was in heaven fucking my little sister. The end of another box of pills came. This time Ms. Green had me put my cock in her ass hole and fuck her that way. Her ass was much tighter than her cunt and I found myself really liking stroking in and out of her shitter. After I came she sucked me clean and gave me the box of pills.
About a week later I was on my way home from school when I saw Joannie coming out of the woods with Donny, Frank and Jim. They were pawing at her tits and ass as they walked out of the woods. "Joannie, What are you doing with them?" .......................