Pimping my sister III
2007-12-28
Before that first night I only thought of my baby sister as a scrawney little girl, even a bit of a pest at times. I never thought of her, or dreamed she could ever be some sort of sex object. But after that time when she stripped for me and swallowed my cock and cum I could never see her as anything but. I would con her into having sex nearly every day sometimes twice a day. We would go into mom's room so Jan could borrow her lingerie. Mom was in good shape and was slim and petite so Jan fit into all of her clothes without leaving a lot of room. Mom had started drinking though as I said earlier which caused her to lose some weight though we were not aware of it. I just knew that it made me hot to see my baby sister wearing silk and satin and mesh and lace. Jan loved to wear it too because she knew that it got me excited and she liked to get me excited. At home she offten lounged around in the nude or with only panties for my benefit (she almost never wore a bra). I could tell she wasn't as excited to have sex as I was but could not help myself when she looked so sexy. But she was really into getting me excited.
A couple months later she had a late period and was kinda worried. We cooled things down a bit for a while but sex was all I could think about around her so I begged and bargained and blackmailed her into sucking cock and still got her into bed a few times. Then after weeks she had bad cramps and bled a lot so we realized that she wasn't pregnant. Looking back we think that it must have been a miscarriage.
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Since then she hardly ever refused me a roll in the hay but often made me beg for it anyways. She got on birth control after that.When I started to set her up with boys at school it didn't take long for word to get around. They would come over to our house after school and she would service them one by one while the others waited in the living room. I was collecting money from them hand over fist and letting sis have just enough to keep her interested and working for me. I took her shopping for more lingerie of her own which she really started to enjoy. What little money I gave her (which was still more than she had ever seen in her young life) she usually spent on a teddy or stockings or crotchless panties. One time we even got away with going into a sex shop without getting carded and got another video along with our purchase.
She didn't wear shirts or blouses to school anymore but teddies under a skirt or shorts or a sexy or revealing camisol. If she wore a bra it was satiny with a see through top. It was a business desision but she also liked the hot look. I'm sure that a lot of the girls were jealous and probably hated her. I tried to graduate the schedule for the rich kids sometimes getting $100 for half an hour with Jan in her bedroom. Some of the less fortunate but smarter kids offered to do homework and term papers for us and she was cool with it so we hardly had to study after that. I was able to buy really nice clothes and trick out my wheels when I got my liscense but then Jan started giving me attitude about our whole enterprise.
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She thought that I was taking advantage of her, which I suppose I was.I thought I'd give her some space and let her cool off a bit so I took my dinner to my room and went to bed. After midnight I hadn't got any sleep so I went to her room for a fuck like I was now in the habit of doing. She was asleep but got up grogily and came to the door. "What is it?" she asked in a stupor.
"I can't sleep," I said.
"So? What do you want?" But she knew what I wanted. There was only one thing I ever wanted from her.
"Come on, let me in," I started in my best persuasive voice.
"Dean, it's late. I'm asleep. Go back to bed. " But her babydoll nightgown and her perfume made my manhood stand up and I wasn't going to take no for an answer. I pushed against the door hard and she fell back from it. I entered her room with a mission and threw her down on the bed and jumped on top of her forcing her legs open to get between them.
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"Stop it!" she cried in a furious, anoyed voice as she struggled against me with all her strength."Why does she have to be so moody?" I thought to myself. "Why doesn't she just lay back and take it like she always does? She doesn't have to be a tease just because she wants a bigger piece of the pie. " I was so frustrated with her. She was just trying to get back at me because I blew her off. She was being such a brat. She wasn't going to get away with it. I would have her like I always did. I held her down and ripped her panties off. "Just shut up and fuck," I grunted through my clenched teeth.
Jan was fighting against me as hard as she could but she gave up obvious opportunities to hurt me such as putting her knee in my groin. She might also have cried out loud enough to wake mother but she never did. I found her pussy and drove my cock into her hard and deep.
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She wasn't quite as wet as she usually was when I fucked her. Usually I slid in and out real slow, thats how I liked it, savoring the feeling of my cock inside her but now I just wanted to slam her as hard as I could. I don't know if she lost her strength or just her will to fight but she was soon as wet as she always was and her nipples were hard. When I had shot my cream into her inermost I didn't say anything or cuddle like we normally do. I just left her there on her bed and went back to my room. I almost didn't have any better luck getting to sleep after that. I couldn't believe what I had just done; I had raped my sister.In the morning Jan acted like nothing had happened except that she was quiet and didn't want to talk to me. I didn't set up any clients for her for the next few days. Finally, almost a week later she came to me after school. "We can't keep this up forever. We need to talk through some things. " The main thing that was bugging her was that I wasn't telling her how the business was doing. "Are you going to get me Johns after you go off to college? I don't know how to do this by myself and I need to learn. " She then explained her vision for her business complaining that she was feeling a bit overworked sometimes when ten or more guys came home to get laid.
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"I want to get Lisa to work for us too. She can help take a load off when we are busy. "Lisa was the next door neighbor and Jan's best friend. She went to a private school or charter or something. She was a little younger than Jan who was fourteen by now but she had bigger breasts. It didn't take me much convincing, some of the guys liked to get blow jobs but would prefer a large rack. The best part of the new vision was that she would bring Lisa over and teach her how to suck cock. Jan would demonstrate on a dildo that we found in mom's room and Lisa would practice on me untill I said she was good enough. Then I would show her all the possitions that Jan said the guys liked. Lisa was fun to sleep with but wasn't very experienced. Training a new girl how to have sex was not quite as exciting as fucking Jan. She was a pro and a natural kisser.
I waited for Jan to talk about the rape but she never did. She didn't even mind so much my making money off of her harlotry because I was marketing her and getting her work and managing her in a way that she didn't think she could do herself. She did insist in knowing how much we were making though.
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When she didn't bring it up I knew I had to. "Jan, can you forgive me? I don't know what came over me. ""I will, if you will do something for me. " You see, the videos that mom had were made for women to teach them how to please a man. In all the months that we were having sex and the several months that she was sleeping with all those boys from school she still had never had an orgasm. She had read about it somewhere and learned that many women don't have orgasms from sex. I had never heard of a clitoris before but she asked me to find it and eat her out. I don't know why it never occured to us for me to give her oral because she sucked cock all the time, mine and others.
She had some literature or something to show us how to find her love button. So we made out to get us both excited and then I peeled off her clothes and kissed her all over working my way down to her crotch. I always loved the smell of her skin and her hair and now I was even more aroused by the smell of her cunt. I kissed and sucked on the lips of her baldness making her sigh heavily. She moaned her approval, "Yeah, like that. " I worked my tongue all over from leg to leg and up and down her lips to tease her like she does me. I slid my taster down into her slit.
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I was torn between licking out her hole to devour her sweet juice and findin her clit to send her into orbit. Her first orgasm was a long and intense as was her second and third imediately following. Of course I prefered to be inside her blasting my cum into her tight muff but tasting her cunt while she wrythed around in extacy was a close second and we could go on and on for an hour without stopping or getting tired or having to "recharge". She didn't need an orgasm as often as I needed her body so most of the time we just screwed each other but every week or so I made sure she got hers.Somehow I don't think it ever got out that we were sleeping together. Mom must've had a clue but somehow refused to believe the evidence. Lisa might have suspected something but never let on. The clientell were getting laid so I'm sure they were clueless. Even so, they weren't talking.
Within a year we hired three more girls to service our growing market. Sometimes we would get girls out of class to meet a John in the john or locker room or under the bleachers. We made sure that all of our girls got all the help they needed with homework and term papers. And we started a database of who was sleeping with whom in the various schools where we were soliciting to ensure that we were safe from disease. We made sure all the girls were on the pill and knew how to use condoms (Again, every employee practiced putting one on me before I drilled them in various positions for training purposes. ) We got me some viagra so I could train the three girls all at once.
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That weekend I had sex almost non-stop from friday night to sunday night. I was tired and a bit sore at the end but it was the best opportunity to get all the girls ready to make money. After they all went home I still slept in Jan's bed with her because the viagra was still potent and I was horney but also because I was anxious to fuck with someone at a higher skill level.After I graduated I took some business classes at the local community college and since we were taking care of Jan's grades she was able to load up on classes and graduate early or take one or two classes her senior year. Most of the other girls were still in the schools all day so we had lots of exposure and plenty of clients. When we were open we had blowjobs in the bathroom and sex in Jan's room, my room, mom's room, the guest room, living room and the atic and basement. I got a really good opportunity to work for a great firm and Jan had more time and no how to put into her own business so we kinda parted. Now we live across town but see each other often. Usually when we get together we do sleep together. I don't even know where mom and dad are. We haven't seen dad in ten years and mom is running some AA program in some church somewhere last I heard.
But Jan is running the biggest, most successful escort service in the state. These days they are more mainstream than they used to be so she doesn't get any flack from the authorities. She is even associated with a STD/fertility clinic where they have access to medical records to verify risks of STD's. Their policy is to verify a disease free client or use a condom - or refuse the client.
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Confidentiality is paramount in this business and she is tops. It wasn't till after she graduated that she told me that one of her clients was actually a Math teacher that I had had. He was a man of integrity and would not have come to her if he thought that she would ever have any of his classes. But he found a schedule of services and realized what she was doing. Since he couldn't prove that anything was happening on school grounds he didn't feel obligated to turn her in. But then he got lonely and wanted company once in a while. She was very careful about where and how she met him and never told anyone but me. She was sleeping with him for over a year.Every year at Christmas, New Years, Valentine's Day, Mother's Day, Forth of July, Labor Day, Memorial Day and on my Birthday Jan sends me one of her escorts for some great sex. It's what she does; she personally pickes them for me herself. It's a fabulous gift that never gets old. But Jan is still the best fuck I've ever had and I still try to sleep with her every chance I get.
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