Sister's Pimp

                       Sister's Pimp - Chapter 26

       By now the interaction between the two family groups had been concluded. Considering the variety of sexual preferences and quirks that were unearthed, our efforts had been successful in the majority of cases. There were new alignments as the members of the various families made more knowledgeable decisions thanks to the greater variety of selections that were now offered. The departure of Karen Bross and Pat Carmody left some significant voids that needed to be filled. In tandem the teenagers were taking a more active role in their families, especially the newer families created by the elimination of other groups that could not survive intact. Through it all I still had two major failed responsibilities to exercise.

       It would have been easy to just kick back and let nature take its course. I was certain that Martine would be delighted to effectively adopt Carly Carmody, who was showing all the signs of a budding lesbian and a tendency towards servitude and masochism. Add to that her beauty and youth and you had a nearly perfect package that would appeal to almost any pervert. Somehow the idea of Martine having total power over this child bothered me. Carly still didn't know who she was in many respects. She needed a guide or teacher not a mistress, at least not yet. My mom and sister had shied away from that responsibility early in the game, leaving yours truly holding the bag.

       Megan had developed into one fine piece of ass and yours truly had no problem moving her into my bed on a semi-permanent basis. In fact the prospect of a threesome featuring my sister, Carly and lucky me sounded like a winner. The big obstacle to that arrangement was anal compatibility. Would Megan's asshole enjoy my cock, and vice-versa; that was the big issue? An added problem had to do with Megan's recovery from the botched sex session we had with the older couple; especially what happened to her with Jonathan, who turned out to be an experienced gigolo.

       A lot of things, all bad according to mom, happened to Megan while I was away learning my trade. Dad beat her constantly when he wasn't "supervising" Megan while she took on his friends for free to gain experience. Just before he died he had started pimping her out to perverts who did things to her that she refused to tell even her mother. At the rate she was going, her career as a professional prostitute would have ended before it truly began. Those dark times still remain hidden from sight. The more I thought about things the more important it became that she reveal to me what did happen to her, regardless of how painful it might be. For this I'd need mom's assistance. I just couldn't bring myself to allow Martine to poke her nose into family business.

       Then there was the issue of prying Carly away from the baleful influence of Martine. The French woman was a very valuable member of my organization and I would hate to lose her. However I was having second thoughts about effectively leaving Carly to her tender mercies. At her age the teen should be experiencing sex in all its forms with both sexes. Instead she seemed to be concentrating on sixty-nine exclusively and only with older women who Martine trusted. I knew for a fact that Carol Faust and Pat Bromback spent plenty of their free time enjoying Carly's tight body under Martine's supervision. It was doubtful if any male had ever gotten within arm's length of her. Home schooling, Calvert style, precluded members of the opposite sex. I resolved to end this unnatural situation even if it meant losing Martine and adding the extra burden of teaching Carly the tricks of the trade to yours truly.

       Not unexpectedly Megan stonewalled my suggestion that she unburden herself about the dark times with the family, especially dad. That led to a discussion with mom about the situation. Even though I got her off twice with some triple tonguing and cock in every hole before shooting my load all over her big tits, and she provided one of her spectacular blowjobs, we were not any closer to solving the Megan problem. It was while we were resting up that I made an off-hand remark about turning Megan over to Ian Connors and Ralph Graves so they could get the truth out of her. Mom's face lit up and she announced that was the answer to the Megan problem. Personally I thought she had lost her mind.

       While mom set up the rendezvous that she claimed would break the silence about what happened to Megan while she "serviced" her perverted clients, I had a heart-to-heart talk with Martine and got the answer I expected. That's when I played my ace and announced that Martine's services were no longer needed in this manner. Since Pat Carmody had given me the responsibility to educate Carly, I was going to turn the girl over to the Graves clan until such time as I could take over the duties of educating her myself. My adversary's face grew tight and blanched; she had lost the game to me and knew it. I wasted no time collecting my charge and escorting the hot bodied teen to her temporary home, warning her that she was now under their discipline and things would go very hard on her if she proved to be a disobedient member of this family.

       Claire Graves was only too happy to take charge of Carly Carmody until such time as I could take full responsibility for her education and discipline. Little did I know that five minutes after I left, little Carly was naked as a jaybird, her hands tightly tied behind her back, and being marched towards Mrs. Graves' bedroom for her first lesson on how to properly satisfy her new mistress. On the way to her first of many lessons she saw the Graves girls with their brother. The trio was as naked as Carly, one girl sucking her brother's long, thick cock, the other seated on his face with a blissful smile on her face. At that moment Carly realized there was a lot more to having fun than just eating Martine's wet hairy cunt all the time.

       

       The next day mom accompanied Megan to the Connors place, or what was left of that family. Four family members, two of each sex, had gone to live with different families, leaving only Mary Connors, Ian and Marian. Ian ran a very strict operation, and his hot, bisexual mother and lesbian sister had the bruises and welts to prove it. Mary was in love with her son's dominant characteristics, not to mention his hard cock. Marian on the other hand was terrified to be around members of the opposite sex except when her big brother ordered her to service them. Ian was thinking ahead and planning for the time when he would have a stable of hot whores that would make him lots of money and provide all the great sex he could imagine. He and I were already discussing ways to train his lesbian sister so she could work both sides of the street. I had to admit that at fifteen, she was built like a porn star. I loved to fuck Marian despite her reluctance to really get down and dirty unless Ian threatened her.

       I was kept busy with a number of problems that arose from the new families. On paper almost all of the new arrangements looked great. Then reality would begin to expose the minor flaws in some of the groupings.  My job would be to straighten things out quickly before the tiny fissures became deep cracks and finally chasms. It was a thankless task, but one well worth the trouble when I did the books and saw what kind of cash flow was being developed by the new organizations. There was no doubt about it, sex sells.

       We were providing custom-made porn films for Japan, other Far East countries and the new rich nations that had oil for sale. Porn films led to invitations to satisfy the needs of those wealthy enough to rent a teen or two for their pleasure. It turned out there was also a market for mature American women with good bodies and a willingness to go the extra mile for their clients. A pain slut like Pat Carmody or an anal queen like Karen Bross were making huge amounts of money for one or two trips every six months or so. In the case of pain sluts, it usually took many months for them to return to normal when the surgery provided by Dr.Patterson and recovery time were added.

       That evening mom had some clients to handle, which meant no information concerning what was happening at the Connors' place until she got back. However she did leave a message on the machine asking me to avoid visiting my little sister as she was being kept rather busy by Ian and some of his close friends, including a few hotties from school who were eager to see just how hot Megan really was. Her laugh was chilling. Then came the kicker, she had left me a little tape of the proceedings to let me know Megan was still alive and kicking thanks to the uppers Ian was feeding my sister every few hours to keep her in high spirits.

       In a matter of a few minutes I was in my favorite chair watching the monitor as the picture came into focus revealing Megan in the nude. She was on her back, arms and legs pulled out to the corners of the bed and tied tightly to the posts. A large ball gag was stuffed into her mouth and it looked like her jaws would fracture any second. Her bald pussy was stuffed with a king-size dildo that was so thick her cunt lips looked like narrow bands of rubber. I nearly jumped out of the chair when the rubber hose came crashing down on her taut belly. By the time I caught my breath, it had struck twice more in the same area. Megan's face quickly turned ruddy. There was laughter from the group surrounding the bed. I identified Mary Connors, her daughter Marian, and a couple of studs that looked familiar, but didn't register. It must have been Ian doing the beating. Again the hose came down, this time flattening Megan's left tit. I winced at the sight, but that didn't stop the hose from drubbing her firm titties for at least a couple of minutes. By the time he got finished, Megan's knockers were beginning to turn black and blue and had grown a couple of cup sizes as well. I relaxed and watched my sister's stuffed pussy take half a dozen vicious hits before this segment ended.

       Megan was now tied in a different position. Her legs were pulled up and over her head and anchored to the posts at the corners of the bed, spreading her thighs and making it easy to access either her cunt, which was now open for business, and her tight asshole. As I watched, a disembodied finger applied a dollop of lube to Megan's asshole. She tensed and grunted at this hint of some one or something going up her tight asshole. I didn't have long to wait on this; Megan was about to be corn holed with a strap-on attached to Mary Connors' loins. She uttered a loud grunt and her entire body stiffened as the head of the dildo began breaching her sphincter. Then inch by stubborn inch it penetrated into her anus, and she couldn't do a damned thing about it. One of the studs grabbed a handful of Megan's swollen, bruised tit and squeezed it until tears flowed down her cheeks. I made a mental note to see who this character was and whether he was worth the money it would take to arrange for a convenient accident that would put him in a cast for a couple of months. Suddenly the screen went blank, leaving me hanging.

       When the screen brightened I was caught by surprise. Megan was still the center of attraction, but plenty had changed. She was now in the bathroom, on her feet, still naked with her hands tied tightly behind her back. Moreover she had a belly on her that should have belonged to a woman in her seventh month or so. Her head was pulled back and the screen showed her jaws propped open with some type of dental fixture. What blew me away was the hose running into her mouth and attached to a bulging enema bag hanging from the shower rod. Then Mary stepped into the scene and mugged for the camera as she measured Megan's bulging belly, declaring that it was almost forty-five inches around. There was laughter and a voice claiming my sister should be able to hit fifty inches if she was properly incentivized. Then the camera moved to show Megan's asshole. It was distended and what looked like cum was oozing out and sliding down the backs of her legs. Then it was dark for good. Until mom returned, I sat in darkness and watched the tape over and over, each time getting me a little hotter at what it showed. What at first was pure anger was now almost pure lust. I hate to admit it, but I wished I'd have been there watching my sister getting worked over good and proper. It would take some time for me to understand my feelings that evening.

       I must have fallen asleep with the tape running. It was mom who woke me up with a knowing grin on her face. My cock was hard as steel, the result of watching my naked sister being put through her paces. Mom pleaded exhaustion from a long day keeping an eye on Megan to make sure Ian and his buddies didn't ruin her for life. Then there was the matter of taking on four clients in their early twenties who had a mom thing and took it out on her with a vengeance. The look on her face told me that she always had them under control and more than one would sign up for another chance to lay the lumber to her. Just to make sure that all was well at the Connors residence she put in a call to Mary and got a blow-by-blow account of what was going on as they spoke.

       Megan was back on the bed, tightly roped and gagged. There were two giant dildos churning away inside her asshole and twat that had been fucked raw for hours after her trip to the bathroom for water sports. They had given her two gut busters by the time they finished. Neither one hit fifty inches, but the last came close enough to make it a foregone conclusion that tomorrow she'd break fifty inches, but hopefully her belly would recover its normal dimensions within a few days. Once they emptied her as much as possible, everyone took a turn making her drink their piss and there was plenty available. Mary had made a tape of that part of the session and she would share it tomorrow when we visited. Megan was on uppers and wouldn't sleep for at least another day. According to Ian it might take that long to break Megan's will and have her spill her guts with all in attendance. I was too confused and mom too tired to have a little friendly fuck session, but she promised me some action in the morning.

       The next morning mom delivered as promised. Last night he'd been too tired to shower and by morning she was over-ripe and frisky, insisting that I go down on her before she would suck my hard cock to make it even harder. Mom's muff was salty, wet and stunk of dried cum. She had me do a fairly good job of cleaning her cunt out so that I could dump my first load of the morning into it. I added a little tease by sucking her clit and then once it got stiff, nibbling on it until it practically hummed. We moved almost seamlessly into a sixty-nine and chowed down, mom getting the better of things. Mom teased me by offering her asshole if I rimmed it for at least ten minutes, kept my erection and fucked her for at least ten minutes. I passed on her generous offer. Still in all, her pussy was a good consolation prize under almost any circumstances. I flooded her loose, sloppy cunt with a huge load of wigglers and she just looked at the ceiling and moaned during the entire time. Afterward we hit the shower and got ready for the day, despite her teasing me that once was definitely not enough for her these days.

       Mom had some business to take care of and so did I. While I made my rounds of the various new groupings and collected my cut of the money the girls were generating in their spare time jobs as semi-pro prostitutes, mom was meeting with Martine to hear her side of the story. By the time I got over to the Connors house things were going full blast and mom was in the middle of things. Megan was obviously juiced to the eyeballs, and from the looks of her body she'd been given a taste of the whippings that were to come today and possibly tonight as well if she proved to be uncooperative. Two teens, who must have been auditioning to be members of Ian's yet to be formed stable of whores, were taking turns fisting Megan. It was astonishing just how much of their fists and forearms my sister's cunt was swallowing.

       Squatting over her was Ian, presenting his bared ass and package for her to worship. Megan's tongue was gliding in and out of his asshole as part of the rim job she was providing. Ian evidently had her totally under his control, ordering her to suck his balls when he got tired of her tongue licking his asshole. My sister's eyes were slits and her face drawn tight, as she worked to meet his demands. It was easy to see that Ian had made quite an impression on her already. He looked up and our eyes met. He grinned and shook his fist, indicating that Megan was doing a good job on him. I gave him the high sign and checked out the two working intently on reaching Megan's cervix.

       They both were stripped down to just their panties, giving me a good look at their tits. One had a set that were perky with nice nipples, but on the small side. Her companion had a pair of grown up tatas with dark areolas and fat, hard nipples. She gave me a look that she must have practiced before her mirror for hours on end. I responded with my middle finger and a tongue wiggle. She colored, while her little buddy giggled and worked her forearm a little deeper into Megan's bloated cunt. It was at that moment the doorbell rang, followed by a pounding at the door. Ian was too busy getting his balls licked to tell them to enter, so I did the honors, almost getting trampled under foot as what seemed like the entire high school football team had just arrived. It looked like Megan was about to become the fuck pig for another gangbang. I decided I had better things to do with my time then watch some high schoolers destroy my sister's twat and perhaps her asshole as well.

       Mom motioned for me to join her in another part of the house where we could have some privacy. We found a quiet place on the second floor for our discussion. It seems mom and Martine had a long talk this morning about her future with the organization, Carly and yours truly. For a change, I didn't blow my top, listening and thinking about what my position was on each topic. Mom smiled happily when I admitted that losing Martine would be a big blow to my plans for the future of the organization. However I was less than enchanted by what was happening to my charge, Carly, under her direction. It bothered me to discover that the teen was being exposed only to women, many of whom were dedicated lesbians with an agenda that included making sure that Carly became one of them. In my opinion Carly needed to see both sides of the coin, and the fault there was my own for not paying any attention to what was going on between her and Martine.

       Mom grinned and casually mentioned that she loved sex with women, girls, men and boys, depending on her mood and their availability. She and the surgeon had discussed her tastes more than once and he didn't seem to have any problem with sharing her with members of the other sex. Naturally he hoped that perhaps threesomes might soon become the norm rather than an isolated event. He didn't know it, but she had already lined up some ladies who expressed a great deal of interest in discovering how the doctor was in bed. That made me chuckle and also offered a way to mend fences with my star employee. Perhaps a threesome now and then with Martine and a lady friend might be just what the doctor ordered. It would be a win-win situation if the third party turned out to be Carly, who wanted to go both ways. When I broached that idea mom beamed.

       We checked back with Ian who had just given Megan a double dose of uppers since she was going to be gangbanged all day without any water or bathroom breaks. She'd not be shown any mercy by the teen male animals that had been saving up their sperm for this event. Ian knew better, but he let them think that Megan was without any protection and might get knocked up before the gangbang was done. That's all these sex-crazed animals had to hear and the fun began in earnest. Mom nodded her head, giving her tacit approval. I bit my tongue since in a court of law she would have jurisdiction over Megan, who was technically still under her mother's, not my responsibility. As we headed out the door, another group of cars was circling the area, looking for a place to park so they too could get in on the action.

                       (To be concluded - rolf palsy)