I become a pimp for my little sister and her friends.
High School Pimp
I was only thirteen years old throughout most of my freshman year in high school. I was only four years old when I entered kindergarten and I had not failed any grades. I was a nerd and had no friends. I just didn’t fit in. High school was nothing like grade school I’ll tell you that.
Then one day in March a senior boy talked to me. I thought that he was talking to someone else and turned around to look. He walked right up to me and then I figured that I was going to get beaten up.
He asked me, “Was that your little sister I saw you with yesterday at the pizza shop?”
I said, “Yes Danielle is my sister. Why?”
He asked, “Does Danielle fuck?”
I said, “No she is a virgin.”
He said, “Too bad I’d give fifty bucks to fuck that.”
During the rest of the day at school all I could think about was him wanting to fuck my little sister. To think that someone would pay me fifty dollars to fuck her. Hell her tits were just starting to grow. I get to see them occasionally but that’s only because we have a bathroom that connects our two bedrooms together. Since we grew up that way we don’t seem to bother with closing the bathroom door or locking it that much. I see her almost every morning in just her panties brushing her teeth. All we ever sleep in is just our underpants. Mom and Dad don’t even wear that much.
That day after I got home from school Danielle was in her bedroom while Mom was downstairs puttering around.
I decided to tell Danielle what the boy had said to me.
Danielle said, “He would really pay fifty dollars to fuck me! Why?”
I said, “I’m not sure but he seemed to really like you after seeing you in the pizza shop.”
Danielle said, “You know that I’m a virgin, don’t you?”
I said, “Yes and I told him that too but he didn’t seem to care and walked away.”
Danielle then surprised me when she said, “We could split the money if I did let him.”
I said, “Why would we split it?”
Danielle said, “Come on you watch all those cop shows with me. You know that the pimp gets most of the money.”
I said, “Yes but that’s television.”
Danielle said, “Then again you would have to get the money, bring him home, and stand guard for Mom while he fucked me.”
I said, “You’re getting interested, aren’t you?”
Danielle said, “Yes, I want to buy some more clothes and makeup. I could use the money.”
I said, “But you’re a virgin. What if it hurts and you scream. Then Mom will catch us.”
Danielle said, “Then we need to do it first and see.”
Danielle then locked her bedroom door from the inside and then went into my room to lock that door too. Then she came back. She took her clothes off including her panties and just looked at me. I took my clothes off too and we stood there looking at each other naked.
Danielle knew more about sex than I did because Mom had ‘the talk’ with her recently. Dad had his talk with me a few years ago but he left out all of the good stuff. Apparently Mom had not left much out at all.
So Danielle got down on her knees and sucked on my cock for a minute. Then she got on her bed and told me to lick her pussy. When I asked why she just said that it was part of making love according to Mommy. I told her that it looked gross. She said that Jenny and Samantha had both licked her pussy and that they didn’t think that it was gross. She told me that she had licked their pussies too. That excited me. I sort of liked seeing pictures of two girls in some of Dad’s magazines. So I just started licking her slit. I actually enjoyed it. It didn’t taste nearly as bad as I had imagined that it would. Danielle sure liked it. After a few minutes Danielle started moaning. She told me to stick it in and held her pussy lips open for me. I slipped my cock into her and it went right in. Danielle tried to explain that it was because we were both ready to make love. I hardly paid any attention to what she was saying because what I was doing felt a whole lot better than jerking off. When I cum in her I really liked it. Danielle said that she liked it too but then I watched as she played with herself. She explained that Mom had told her that women usually had to finish themselves off after sex because men just couldn’t do it long enough. Anyway after she took care of her own needs we got dressed and went downstairs.
When Dad came home it was usually time for dinner and Mom had it almost ready. During dinner Danielle asked Dad to tell her about pimps and whores. That started a very interesting lecture on how pimps take advantage of young girls, get them hooked on drugs, take all their money, and beat them up. Mom talked about some of the movies that she had watched when we were in school. Some expensive call girls make a lot of money and somewhat safer while the street hookers get into cars with complete strangers and are murdered. Then Mom and Dad started going back and forth on whether or not prostitution should be legalized. Dad said that it would just invite more girls to do it. Mom said that it was good because then men would not be raping girls if it was easier to get laid. They even got into white slavery and young girls being kidnapped and sold as whores around the world. Especially young pretty blondes like Danielle.
Then Mom lectured us both on getting pregnant, using condoms, AIDS, and VD.
After dinner we went back up to our rooms just to get away from them. We locked ourselves in and Danielle wanted me to fuck her again and this time harder and longer as if I were paying for it. Being thirteen I did the best that I could, then about twenty minutes later I fucked her again. She begged me to do it as much as I could. She was training herself to please me. She said that I seemed to like it when she squirmed, when she cooed softly, and when she panted during her orgasms.
That night I fucked Danielle six times and she slept in my bed. In the morning we did it twice before school. Danielle really wanted me to invite the boy home after school.
I found him and asked him if he was serious about paying me fifty dollars to fuck my little sister. He sure was and said that he had a few friends that would like fuck her too. I told him that I could only take one home at a time and he said that he wanted to be first. So he told me where to meet him after school.
When we went into the house Mom said hi and I told her that he was going to play a video game with me for a while. She just smiled and told us to enjoy ourselves.
Danielle always gets home before I do so she was sitting on my bed when we walked in. I locked my door and Danielle said that she had locked her door too.
Danielle opened her knees up and let us see her pink panties as she asked, “Did he pay you yet?”
I patted my pants pocked and said, “Right here.”
Danielle stood up and took his hand then she led him into her bedroom. She closed the bathroom door on my side. So I just sat there wondering. Finally I sat down on the floor near my bathroom door and cracked it open to listen. There wasn’t much to here so I went to play a video game.
I had looked at the clock when they went in and noticed that he came back in just twelve minutes holding his hand over his cock. Danielle was naked and standing in the doorway of the bathroom. He handed me another thirty dollars and said that Danielle told him he could have a discount for doing it the second time. They went back into her bedroom. Fourteen minutes later he came back out dressed. He thanked me for letting him fuck my sister and said that he would be back in a couple of weeks to do it again when he got some more money. He said that he would be sure to tell his buddies too. Then I walked him to the front door. Mom told me that it was almost time for Dad to come home.
I went back upstairs and found Danielle still naked and on my bed. She wanted more sex so I fucked her then we talked about it. She really liked getting fucked and she had really liked him. His cock was bigger than my cock was, but he wasn’t as good at using it. He had told her that he was still new at sex and thought that girls his age would laugh at him. That was why he was so interested in younger girls. Danielle had told him that she might be able to get some of her girlfriends to let him fuck them too. That had excited him.
We both got dressed and looked at the eighty dollars. Danielle was excited and only took thirty dollars. When I asked her why she said that it was because it felt so good. She also thought that I should pimp out two of her girlfriends too. She wanted me to give the girls twenty dollars and keep thirty for myself. For the second fuck she wanted me to give the girls ten dollars and keep twenty. That added up to the thirty dollars that she wanted for the two fucks. I asked her about me and she said that her pimp should be able to fuck her anytime that he wanted too for free. I could not see anything wrong with her facts.
During dinner Danielle asked Mom if two of her girlfriends could come over and play for awhile. It was okay with her so Danielle called them. I went up to my room to play video games.
Shortly Danielle arrived with Jenny and Samantha. She entered my door, which seemed to surprise both girls. Danielle locked the door behind them and that seemed to surprise the girls even more. Next Danielle blurted out that she had just been fucked by a senior in high school and that he had paid for it. Of course they didn’t believe her. Danielle leaned back on my bed, removed her panties, and told them to examine her pussy if they didn’t believe her. Both his and my cum was dripping out and her panties were really wet and slimy. I noticed that her pussy was reddish from being fucked. They agreed that she looked like she had been fucked but that they wanted more proof. Danielle went into her bedroom and got her digital camera. She pushed me away from my computer and downloaded the pictures. There was Danielle naked with Roger Reed fully clothed next to her. The next one was with both of them naked. The next one was of him fucking her and her legs up around his waist. After that she had a dozen pictures of his cock in her tiny pussy then of the white goo flowing out and down into her asshole. Danielle told the girls that pictures were part of the deal. She had to send him the one of him fucking her in an email later.
Then Danielle showed them the thirty dollars, twenty for the first time and ten for the second time. Danielle pointed at me and said that her pimp gets the rest of the money. She then asked the two girls if they wanted me to be their pimps too. Hell thirty dollars was six weeks of allowance to these girls. They asked what it involved.
Danielle told them that they had to let me fuck them as often as I wanted too especially tonight so that I could tell the guys in school what a good fuck they were. They had to let me take nude pictures too for advertising purposes. She handed me her camera and told the girls that they needed to lick her pussy too so that they would get used to the taste of cum. I got hard instantly but took a lot of pictures. Then I told Jenny that I wanted to fuck her. She was already moist but I licked her pussy anyway. Danielle tastes better but it didn’t matter. I fucked Jenny while Samantha watched intently and Danielle took pictures. Then I licked Samantha’s pussy and got hard again, so I fucked her too. Danielle made the two girls eat each other out while she took more pictures. As soon as I was hard I fucked Jenny again and then Samantha. Both girls said that they would come home with Danielle after school if I wanted to bring three boys home too. Okay!
After the girls went home Danielle practiced sucking my cock until she fell asleep. She got me to cum in her mouth twice and she swallowed it. She said that she had heard Mom talking about doing that to Dad. Wow! My little sister was really something.
The next day at school, Wednesday, I was just about the most popular boy there. Roger introduced me to about half of the senior boys. He was showing off the picture of him fucking my sister. I showed them nude pictures of Jenny and Samantha and suggested that I could take three of them home with me that night. Then there was a fight over who would get to go home with me. Roger said that he had done it twice so if they only went once each that six of them could fuck the three girls before my father got home. Okay! But then they fought about that. Roger said the first six that put fifty dollars in my hand would get to fuck the girls that night. That worked, plus I started a list. I had Thursday and Friday full and was working on Saturday. Saturday morning was good because Dad was off with his buddies most of the day and Mom was off with her friends most of the day too. So I would be fine with several boys.
That night after school Mom was surprised to see me with six boys but I just told her that we were having a video game contest and that I was the judge and referee. She believed me.
The six boys walked into my bedroom and saw the three girls dressed and sitting on my bed showing off their panties under their short skirts. The boys had already picked their girl from the photos I had shown them. I just patted my pocket. The boys knew that they were to get a picture of them fucking their girl and that the girls got several other pictures. Danielle rolled out two sleeping bags and asked the boys if they were shy. Hell no they lied. They watched as Danielle, Jenny, and Samantha took off all of their clothes. They all had A-size boobs and very little hair on their pussies. They posed with the boys for pictures and then had the boys undress for the nude pictures with them. Then it was time to fuck.
The three boys let the girls suck their cocks for just a minute then laid them back and fucked them. I looked at the clock. The first boy took three minutes, then four minutes, while the last boy took five minutes. Then the next three boys climbed on the girls and fucked them too. Then the first three gave me another thirty dollars and fucked their second girl. After that the next three paid me and fucked a different girl too. When they were broke I walked them to the door.
I counted out the money while Danielle took the girls into the bathroom to clean up. Each boy had paid me eighty dollars. I was to give each girl thirty dollars. It just didn’t seem right but I put the money in three piles for them and put the rest away. When the girls returned they said that they had a great time and asked me if I wanted to fuck them too so I let Jenny suck my cock until I came in her mouth. All three girls got dressed. When Mom called us down to dinner the girls took their money and went home.
Danielle couldn’t wait to talk to me after dinner. She had really enjoyed having six boys there and had been thinking about Saturday. I told her the way that it was working out. Danielle was impressed with my pimp capabilities. We figured that the three girls could handle six boys every hour and that we were good for about eight hours. So to be safe we would do it for just six hours allowing an hour on each end for safety. Six times six meant that each girl could satisfy thirty-six boys. At fifty dollars each we would bring in a small fortune. Wow! Fucking wow! Danielle was astounded. She knew that she could go shopping with on Sunday. Sunday? How could the girls get fucked on Sunday? Good question!
The next day at school, Thursday, I talked to Roger about my Sunday problem. He suggested his grandmother’s house. She was in the hospital recovering from a broken hip and he checks on her cats every day for her. All he wanted was to be able to fuck each girl once that Sunday. So I asked him about Saturday too. Sure with the same three fucks. Hell yes. That way I could let the girls work most of the day. So that day in school the word spread. It was nice having seven guys praise my girls. Roger told me to let twenty guys come over each hour and see how it goes. He said that most of them would come back in a couple of hours for seconds and maybe even thirds. After all what horny senior wouldn’t want to fuck all three of my girls.
That day after school I took six more boys up to my room. They each fucked two of my girls and said that they would be at Roger’s grandmother’s house on Saturday then they left. I explained to the girls about Saturday and Sunday. They were excited before but now that they knew that they might earn a small fortune it was even better. They figured that their pussies would be sore but what to hell. Samantha suggested that we recruit a couple more girls to help out. The girls got permission to stay for dinner and to invite the other two girls to come over afterwards to play. Mom was easy.
After dinner Bethany and Tiffany were hired. The other girls talked them into it easily and I fucked them both twice while the others watched and Danielle took pictures. I took some nice full frontal and top half pictures to show around school the next day. The two new girls had to eat the cum out of one another. All five girls would be ready to go to Roger’s grandmother’s house before eight o’clock to get started. They would not go home until about six that evening. That would be a ten- hour day.
Friday at school I had over two hundred guys ask me what time to show up on Saturday and on Sunday too. I told them to just show up and wait their turn. Roger suggested that I buy movie tickets at Staples and then hand them out to figure who goes next. I could get everybody’s name too so that if they came back for seconds that they could get the discount rate.
That day after school I took ten more guys home with me. All five girls were there on my bed showing off their panties for us. The guys each fucked one girl and two of them fucked a girl for the second time. Danielle was one of those girls and Tiffany was the other. The boys liked the fact that Tiffany was only ten years old. I took in a lot of money and paid each girl her share. It just didn’t feel right giving them less than I got for doing all of the work. They didn’t seem to care at all and I got to fuck Bethany and Tiffany again before they had to leave. That night Danielle tried to fuck me to death.
Saturday morning the four girls were at our house bright and early. Danielle told Mom that they were going to watch the boys play baseball at the park. Mom was not too concerned as long as they were back before dark. Mom was responsible for them all since the other girls were spending the night at our house.
When we got to Roger’s grandmother’s house there were already twenty or more guys waiting for us. Roger showed the girls which rooms to use upstairs while I started selling the tickets. He said that he would take the pictures to help me out. The five girls came downstairs naked and asked who was next. It wasn’t even eight o’clock yet but they were ready to go. After that the guys were willing to take the next girl that came down the stairs. Things were going real well. The girls took care of fifty guys in that first hour. They were so anxious that they were running downstairs before the last guy had even gotten dressed. I told them to slow down, wash up between guys, and to take it easy. I figured that each girl would have to let a hundred guys fuck them that day at that rate. The girls didn’t mind but they did wash up and escort the last guy back downstairs before getting her next guy. After that we were down to about forty guys an hour. They did not stop coming in either. Some guys came back with friends too. At five o’clock I had to slow things down so that the girls could stop at seven. They sure needed a nice bath after that. I had sold four hundred and fifty tickets that day of which a hundred were seconds. I had a whole lot of cash too. Each girl had earned sixteen hundred dollars each. I got to keep the rest so I gave Roger five hundred for helping us out. He was very appreciative and said that we could use the house anytime that we wanted too.
That night at home the girls went right to bed. They were exhausted. After all each girl had been fucked ninety times that day. It was decided to stop at five o’clock on Sunday.
Poor Tiffany’s pussy was raw from being fucked so much. She was the youngest and had the smallest pussy but she got fucked just as much as the other girls had. She never said a word until it was all over either. She even went along with the extra hour and didn’t say a thing.
That night at home I put some antibiotic cream in her pussy and very gently used my finger to rub it around. Sunday morning she said that she was ready to do it again but I knew that she wasn’t up to it. I applied some more cream and this time I used my cock to rub it around inside her. She cried so I knew she couldn’t do it. I didn’t want her to go home and tell anyone so I made her come with us anyway.
I calculated that with four girls I could handle thirty-two guys an hour. With a half-hour for lunch I could sell two hundred and seventy tickets. I was much better today at it and could tell them almost exactly when to come back. I had sold the two hundred and seventy tickets by ten o’clock in the morning. I knew that I needed more girls. Roger and I talked it over and figured that the girls could use the rest during the week and then use the house on weekends. We could get the girls to tell their parents about a sleepover and just let them stay right there all night. If their pussies didn’t wear out they could work later too.
For entertainment every half-hour little Tiffany let all of the boys waiting watch her get on the dinning room table and then she would let one of them apply her antibiotic cream. She offered to give them blowjobs too but just two an hour to see how it went. The guys got the ‘seconds’ rate for a blowjobs.
The guys were complaining that I had sold out too early for the day and were demanding that I sell them tickets for the next weekend already. Sure! Why not! I calculated that Tiffany would be up to about half speed and started telling them when to come back based on thirty-six per hour.
Sunday went very well and even ended on time. The girls were paid and sent home. Danielle and I were tired. Soon I got a panic call from Tiffany; her sister wanted to see me. Now! As soon as they hung up they were on their way. I panicked but Danielle calmed me down.
When the girls arrived Danielle brought them straight to my room. I knew Tiffany’s sister Sherri from grade school. Sherri was my age but a year behind me. She looked real pretty too. I was expecting her to threaten me but instead she wanted to become one of my girls. What! That’s right she saw her sister’s pussy and had gotten her to talk. Sherri wanted in on the action. Danielle told her that the boys didn’t like girls with tits. Sherri told her that the boys did like tits and that they really liked hers. Then she explained that her father had raped her several times and that when her mother found out about it she had thrown him out and put her on birth control pills. Then as time went on her mother had let some of her boyfriends fuck Sherri too. She wanted to start getting paid for it.
I explained about the pay, the nude pictures, and that I get to fuck her all that I want too. She agreed and undressed right there in front of our sisters. I took pictures and then Danielle took some of me fucking Sherri. She really did have nice tits. Sherri had sure grown up over the last summer. To help get her used too fucking a lot of boys Roger came over after school and help me fuck Sherri. By Friday we had used her pretty well and she seemed to really enjoy it. Tiffany was back in shape too. Word had gotten around that I had another girl and that I could handle about fifty guys an hour. By the close of school on Friday I had sold out the entire weekend. Twelve hours on Saturday and eight hours on Sunday meant one thousand tickets. Holy shit! Fifty thousand dollars. I couldn’t figure out if a guy was going back for seconds or maybe just selling his cheaper ticket so I decided that one price fit all from then on. I had a few guys buy four tickets with different numbers so that they could fuck my girls a few hours apart on both days.
Saturday morning Danielle, Jenny, Samantha, Bethany, Tiffany, and Sherri were all set to begin. We arrived at Roger’s Grandmother’s house early and the girls just undressed there in the living room, grabbed the first six boys, and walked them up the stairs. Sherri was right the boys went crazy over her tits and hairy pussy. They were all hoping that they would be next whenever Sherri came back down to get one of them. Guys started trying to bribe me to let them fuck Sherri but I just couldn’t figure a way to do it. However I told them that I would sell them special Sherri tickets for the next weekend. I had a new roll of movie tickets that were a different color but I could only sell a hundred and sixty tickets for the two days. I even charged seventy-five dollars for them and no one cared. Wow what a business to be in.
I had sold out of Sherri tickets on Saturday for the next weekend and did not really want to sell them too much further ahead. On Sunday I had sold out of the following weekend for the other five girls as well. I had guys requesting that I get more thirteen-year-old girls too.
After we closed up on Sunday the girls had decided on an even split so I gave each girl thirty-four hundred dollars each. Holy shit were they ever impressed. It was a lifetime of allowances and they had earned it in just one weekend. I told Sherri that I had sold her out for the next weekend at a higher price because of the high demand to fuck her. Then I asked her if she knew any girls her age that would be willing to join in. I mentioned the high demand again. She smiled and said that she would check with a couple of her girlfriends. I told her that she was right about the boys liking her tits too.
Monday after school Sherri was waiting in my bedroom with Danielle and three other girls. I noticed their tits right away. Michelle, Rhonda, and Yvonne were there to join up. They had listened to Sherri and had seen her thirty-four hundred dollars for two days work. They were ready to get naked, get photographed, and get fucked by me. I took the pictures and fucked them all once each. I told them to come back every day after school so that Roger and I could fuck them some more so that they would get used to it by Saturday. No problem they were ready to cooperate.
I now had nine girls in my stable, one ten-year-old, four eleven-year-olds, and four thirteen-year-olds.
The next day I started selling the thirteen-year-old fuck tickets. By Friday I had sold the additional four hundred and eighty tickets at seventy-five dollars each.
Saturday morning the new girls were excited. As usual we got to grandmother’s house about twenty minutes early. The girls undressed in the living room and took the first nine guys upstairs. That morning I received a lot of compliments on my new girls.
At noon after the pizzas arrived I had the girls stop after the guy they were with had finished and come down to eat. The guys loved seeing all nine naked girls sitting at the dinning room table eating pizza. Sherri announced that she had let three of the boys fuck her asshole for an extra ticket each. She said that after about every twelve guys she started looking for a smaller cock with two tickets and made him an offer. She said that it isn’t for every girl that’s for sure. She said that she didn’t think she wanted to do it too often but that she would see. Tiffany asked her about it and her older sister told her point blank not to try it for a couple of years and only with small cocks.
Sunday evening when I settled up the younger girls got four thousand dollars each. The older girls got almost seven thousand dollars each. I got to keep forty thousand dollars after giving Roger a thousand dollars and buying the pizza.
At thirteen years old and only been a “Pimp” for a couple of weekends now I had a small fortune in my hiding place. I was the most popular guy in my school and I knew that I had a great future in this business.