Wall Street Pimp: Open Contract Part 05 The following weekend the memory of Nina was still fresh in Max's mind. He remembered every sweet stroke he made into the Spanish musician's rectum. He could close his eyes and remember the image of thighs with dark Spanish complexion spreading wide to expose welcoming orifices. He remembered Nina's full lips twisted in discomfort, but she kept telling him to push. The smell of lavender mixed with KY stayed with him for days. It was a nice Fall Saturday morning, and Max thought about when he would next call Nina. She didn't want to be fucked in her pussy, because she reserved that for her boyfriend, but she was willing to take it up the ass. That was good enough for Max. Max smiled to himself as he walked down the stairwell of his apartment, wearing his old Wharton sweatshirt, comfortable shorts, and sneakers. He was heading to the park when somebody coming up the stairs in the opposite direction him made him stop. "Max, I'm so glad you're still here," Shannon said coming from the other direction. "Shannon, what are you doing here?" "Sorry I didn't call, but I just needed to catch up with you ASAP, so I decided to just get over here quickly." "Is everything okay?" "Yeah, everything's fine. I was just wondering if you wanted some... business. Today... and for six hundred and fifty dollars... uh... please?" Shannon said stopping a step below Max. She was wearing a blue warm-up jacket, loose cotton shorts, and sneakers. Between working out and fucking, did she have anytime for studies? Max wondered. "Six hundred and fifty dollars? That's a pretty specific number. Are you sure everything's okay? If you need the money for something important, I'll take care of it." Shannon laughed and looked down at her feet. "You're sweet, Max. It's not 'important' like I need an operation or something. I do NEED it, though. Burton just put out its new Thrasher women's snowboard. And I HAVE TO have it. The season is coming up, and I heard some slopes are about to start producing man-made powder. So I was wondering if I could interest you in six fifty worth of fun today..." Max sat down on a step and chuckled. Shannon then kneeled in front of him and moved into gently kiss Max's neck. Her long blonde hair was done in a single braid and smelled like citrus shampoo from a recent shower. "C'mon," she whispered into his ear and nibbled his lobe. "I'll make sure you have a good time today." "Six fifty is significantly more than you've been getting. What are you going to do that'll earn you this snowboard?" "Aw geez, Max," Shannon pouted. She put her head down to think, and in a few moments said, "Okay, you can do ANYTHING you want to me today." "Anything?" "ANYTHING... and yes, you can fuck me in the ass." Shannon said the last part quietly in a defeated tone. Max curled a smile. "Okay, 'anything' sounds like it could be worth it. But first I'm meeting some friends at the park to play football. So I'll have to meet up with you in the afternoon. Unless you want to come?" "Football? I like football. Yeah, sure, I'll come." Shannon had to go to her apartment first to pick something up. Max grinned when he saw the five foot ten leggy blonde run out of her apartment wearing a Steve Young football jersey. The jersey was not an official size jersey. It was cut off just below Shannon's breast showing her well-toned midriff. Max was amazed it could even fit the number eight on the back with so little material. "Have you ever even watched Young play?" Max asked incredulously. "I'm twenty... not two," she said jumping into Max's Cadillac roadster. The XLR then peeled away to the park. At the park Max and Shannon met up with four of Max's friends. One of them Shannon had already met once, Isiah, the star investment analyst working at Max's old firm. Isiah Robinson was an African-American in his mid-thirties. Max took him on early in Isiah's career, spotting good talent. Isiah remained single, and kept himself fairly fit. He and Max were the most fit men there that day. The least fit man was a large man who was named Herbert Janison. He was about forty, caucasion, and had a jolly laugh. He worked at Max's old firm, one of the lead accountants on the team. Max found him fun to be around. He was tall at six foot five, and had about two hundred and eighty pounds of muscle and fat. Probably mostly fat, Max guessed. The third man present was the oldest. At fifty three George Tomlin was VP of Development at the firm which bought Max's firm. He was a tall, six foot two, thin man. He colored his hair, and it was obvious. He was an old friend, and had done Max many favors in the past. The fourth man was the youngest, Paul Cray. He was only thirty two, and worked for another investment firm. He use to work for Max's firm, but transferred over to a rival after Max left. He was a shorter, five foot ten, wormy man. But Max admired his determination. They all greeted Shannon warmly. "This is Shannon, my... gym buddy," Max said. "I hope you guys don't mind an extra player." "Not at all, Max," George said. "Jeff wasn't able to make it anyway, so we're even now. Though, I don't know about you younger guys, but my old legs are going to have difficulty keeping up with young Shannon's." "Speak for yourself, gramps," Paul said defiantly. "I use to do track in college. I still have some spring to these legs." Paul was already smoking a cigarette. He could probably get good speed, but Max wasn't sure if he could maintain that very long. "Okay, let's play," Max announced. "Everybody get your flags on, and we'll split into teams." "Flags?" Shannon asked incredulously. "You're not playing tackle?" "Whoa... she's a tough one," Herbert chuckled. "I'm okay with tackle. Size gives me an advantage then. I'll sumo your asses... oh yeah!" "Most of our bodies can't take as much punishment as your can, Shannon," Isiah said. Even though Isiah ran five times a week, and was on a recreational rugby team, he probably could take it. Max knew that Isiah was speaking on behalf of George, the oldest, to spare him from admitting his frailty. "Alright," Shannon said, "flags it is." Everyone tucked colored flags into the back of their waist bands. It was Max, Shannon, and Herbert versus Isiah, George, and Paul. Max was quarterback. "Let me snap the ball!" Shannon volunteered eagerly. Max grinned as Shannon bent over the ball pointing her ass straight at him. He then placed his hand between her legs ready to receive the snap. The top of his knuckles brushed furtively over her crotch as he shouted the count. Shannon ran rings around all of them. On the open field, nobody could catch her, and she was Max's number one option. Max went to Herbet occasionally to make him feel good and for short yardage. Shannon once made a diving one-handed catch, and rolled right back up to her feet - her jersey almost coming off and showing off a zip-front sports bra - to sprint to the end zone. Isiah almost caught her, but he couldn't keep up. "Wow she's athletic," was all Paul could say wheezing next to Max. "Where'd you get this ringer?" "The Olympics in volleyball just barely cut her, so I got her." Isiah quarterbacked for the other team, and they were pretty good too. While Shannon covered the older George well, especially with her height and speed, Herbert couldn't cover the smaller Paul. When Shannon covered Paul, Isiah would go through George, who would always be in the right place at the right time against Herbert. Max's team was still winning. One play that might have been the nail in the coffin, Max threw deep to Shannon. She jumped high to get it, but Isiah was right there with her. He tried to grab Shannon's flag before she could sprint away from him, but was only able to get the bottom of her cotton shorts. He held on anyway and they were pulled down to her ankles. Shannon didn't care - focused on the game - she kept going. She just avoided tripping over her shorts and jumped out of them. In her white panties - her flag had been tucked into their waistband - she sprinted for the end zone. Shamelessly she turned and spiked the football into the ground. Turning around her panties showed volleyball pictured right over her crotch. She crossed her arms under her breasts and looked back at the admiring older men in triumph. "Very impressive," George said, "her and you, but mostly her." "I think you better take possession of these," Isiah said to Max handing him Shannon's cotton shorts. Max waved Shannon's shorts in the air. Other park goers were starting to stare at the tall blonde in her underwear. Max decided to have fun and get her out of public at the same time by throwing her shorts behind some trees and bushes near the field. "You bastard!" Shannon shouted running into the vegetation to look for her shorts. "What an old man like me wouldn't give to be with a girl like that," George said as he stood next to Max and the others watching Shannon's pantied covered butt enter the woods and go out of sight. "Really?" Max said considering what he just heard. Shannon had a hell of a time finding her shorts. Max had thrown them deep into the area over grown with trees and bushes. She finally found them in a small grassy clearing, hanging from a tree branch. It was quiet there, and out of sight of the rest of the park, but there was an opening in the tree canopy to allow some sun in. Shannon wasn't quite tall enough to reach her shorts. She tried jumping a couple times, but even her good vertical couldn't reach it. Next she scanned for a stick or something to prod it down with when she saw Max enter the area. "Hey, Max, can you reach my shorts?" "What's the hurry? Maybe you should stay like this for a little longer." Max came up to Shannon and pulled her towards him. He kissed her deeply and sent a hand up her Steve Young jersey. "Mmmmm... why Max... isn't this illegal use of hands?" "There might be some unnecessary roughness too," Max said and quick pulled the jersey over Shannon's head. She gave a startled yelp, but then continued to deeply kiss Max as he unzipped the front of her sports bra. While still kissing the topless girl he tossed her sports bra up to the branch with her stranded shorts. "I think we should get the guys." "Yeah, we should get back to the guys," Shannon said. "They're probably wondering what's going on in here. Can you get my shorts and bra? Oh wait, just get my shorts." Shannon stooped low and picked up her jersey and put it back on without the bra. "I'll bet they'll love it if I finish the game with a little more jiggle," she said conspiringly. Max wasn't really listening and moved a little closer towards the park. Shannon returned to under the branch to reach for her shorts again and continued her plan. "And if they're lucky," she continued, "they might get to cop a feel. Will you get my shorts down already?" "Hey guys, why don't you come in here?" Max shouted back towards the park. "What are you doing? Don't ask them back here!" But the other four men must have been standing right on the edge of the bushes, because they immediately entered the little clearing. They older men all had a smirk on their face and leered at Shannon. The leggy blonde took a couple steps back, not sure what to make of all five men in front of her. "Come here, Shannon," Max said. "Why?" "Because I said so, and you said you would do what I said." Paul was smirking a rodent-like smile. The others just had smiles of curiosity. Shannon walked over to Max and the others after a moment. Max put his arms around Shannon and made her face the other men. "Why don't you tell them, Shannon, what they might get to do if they're lucky?" "What? I... uh... nothing... I didn't say anything about that." "Now, Shannon, you said: if they're lucky they could cop a feel. They're pretty lucky guys. I think you should let them have a feel." "Uh... Max... no..." Shannon said struggling as Max held her in front of the others. "Now, Shannon, are you going to do as I say? I thought we had agreed on this. You were going to do as I say right? Or was I wrong?" "Yeah, but... Max, come on..." Max could feel Shannon's six-pack clench and unclench as he held her. Her long hair done up in the single braid had started coming loose from the game and her current struggling. Finally she stopped. "Fine," she said defeated. She reached at the edge of her Steve Young jersey and pulled them up to reveal her perky c-cups. "Nice..." Isiah said admiringly. Max moved his own hands up to fondle them and said, "Aren't they nice? Give them a squeeze." Max moved his hands back to where Shannon's narrow waist started to flare into her hips, and held her steady as the four men reached out to touch Shannon's breasts. Shannon closed her eyes and tried to ignore the sensation of having four - and sometimes more - hands moving across her breasts. "This is awesome!" exclaimed Herbert as his chubby fingers pinched a nipple. "I think she's starting to like it," Paul said pulling at the other nipple. Max looked to see that Shannon's nipples were standing forward on their own, and a familiar rosy hue had appeared across her chest. "Oh yeah... this little sweetheart loves getting her tits felt up. Isn't that right?" Shannon remained silent and with her eyes closed. She didn't want to admit it, but she was starting to get turned on with the five men all around her... touching her. Max then moved his hand into her panties and started to massage the lips of her vagina under the volleyball picture over her crotch. "Aww.. come on, Max. Please don't do that..." Shannon squirmed a little, but eventually gave up and let Max's fingers dig in between her legs. Max then started pulling down the girl's panties until they were stretched across the middle of her athletic thighs. "No... fuck..." Shannon said squirming a little more. "You guys have to feel this sweet little cunt." Paul's hand was the first to dive into Shannon's vagina. Herbert stroked her trimmed pubic hairs and mons. Isiah and George continued to fondle Shannon's breasts, but watched eagerly for an opening to her crotch. Shannon had let her jersey drop, but Isiah held it up on his own. Shannon's arm moved randomly, at first going to pull the hands off of her, but then pulling back as she concentrated on letting Max and his friends do what they wanted to her. "Pull her panties all the way off," Max said. Paul did it as Herbert moved his fingers into the briefly vacant vagina. Shannon let out a little sigh of pleasure as Herbert's thick and fat fingers probed her. When Paul threw the panties to the side, Shannon was then only clothed in her jersey and sneakers. "You know, Shannon," Max said into her ears. "These guys are really lucky. In addition to feeling you up, I think I'm going to let them all fuck you." "Geez! Fuck no," she swore. "Absolutely not. I'm drawing the line right there. You're not all going to gang bang me." Shannon struggled harder, but Max grabbed her arms and pinned them to her side. "Remember our agreement," Max said. "If you want to back out, you can. We'll call the whole thing off. But I want you to fuck every one of my buddies here. Will you do that for me, honey? Remember our agreement..." Shannon fought a little more, but then remembered. She had agreed to anything. She wanted that snowboard. And finally: she really wanted to make Max happy. "Okay... you can all fuck me. I'll fuck whoever you want me to, Max." "That's a good girl," Max said lowering Shannon to the grass. The others gathered around her, five men, circling the bottomless blonde with her jersey pushed up to her neck. Paul and Herbert were both between her legs, holding them apart, feeling her out. Isiah and George were on either side, each fondling a teat, and George was also caressing Shannon's well-toned stomach. "Pull her legs apart, guys," Max said. "Pull them wide. You're going to like this: she's really flexible." Shannon's legs went up and out. They put her easily into a full split, opening her vulva and asshole up for full access. Isiah and George put a hand each between Shannon's legs. It was crowded, but four of them now were fondling Shannon between her legs. Herbert also stuck his pinky up Shannon anus which brought a grimace to her face. "Yeah, jam it up her butt, Herbert," Max said. "Fuck her in the mouth or pussy, guys, but no dicks in her asshole. That's reserved for me only right now." The four nodded still stroking the girl. "Max," Shannon mumbled up to him. "Make them use condoms. I only want you to fuck me without one. And I don't want to kiss anyone on the mouth. Please Max." "You heard the little lady. Sheath it or you're not going in." Isiah then pulled out a large pack of condoms from behind his back. "Good thing I got these from the car," he said. "In return," Max said into Shannon's ear, "we're going to let the boys get a little rough with you. You can struggle, and if you get away, you don't have to fuck anybody. It'll be a fun game. The guys can rough you up a little bit to hold you in place. No serious rough stuff, guys. How's that sound? It'll be like a new sport. You like sports, right, my little varsity athlete? And, Shannon, no kicking in the crotch and no biting. If they get a dick into your mouth.... no teeth. Gentleman, fuck away." Max then got up and walked away to sit on nearby stump. He watched as the others positioned themselves around the struggling Shannon. "I think we should let George have first dibs," Isiah offered. "What? Why?" Paul said. "Seniority," Isiah said. "I second that," Herbert said. Isiah held Shannon's arms down over her head while Herbert and Paul kept her legs apart. Isiah pulled Shannon's jersey over her head, covering her view. She was only a naked girl on the ground between four men. George found himself between her legs and he couldn't get his shorts off fast enough. He quickly strapped on a condom and wacked at his penis a few times. He was the oldest, and needed a little help to get fully hard. It didn't take long, though, as he looked at Shannon splayed out before him. "Ungh.... fuck..." moaned Shannon as she felt George's penis up against her vagina. George penetrated Shannon and held himself fully inserted for a moment, relishing the sensation of the young blonde around his cock. Shannon tried to buck him a couple times but couldn't with the other three holding her down. Soon her body surrendered and she relaxed as the sixty year old man started to violate her. In about three minutes George's body stopped moving and shuddered. "Fuck," he mumbled. "She's got some great poontang." The guys chuckled as George pulled himself off. As they tried to switch holders Shannon broke loose. She scrambled on the ground, but Isiah and Paul each got a leg and she fell to her belly. George and Herbert quickly got around to hold her down from her back. "I'm next," Paul said from Shannon's left leg. "Make her kneel. I want her doggy-style." Isiah and Paul lifted Shannon's rear up while George and Herbert held her face and chest firmly on the ground. "Oh yeah," Paul said looking down at Shannon's pretty ass. "Come to papa." Paul pulled down his shorts and put on a condom. After mounting Shannon's rear Paul began to thrust immediately. Paul pumped her doggy-style with a wicked grin on his face. Isiah didn't need to help hold Shannon down at all from that position, and moved to Shannon's head and took off his shorts. He pulled out his black penis which Shannon looked at with a little fear. He quickly strapped a codom on. "Get her head up guys," Isiah said. George and Herbert pulled Shannon's face up and right at Isiah's large penis. She held her mouth shut as its head brushed up against her lips. "Come'on, baby," Isiah coaxed. "You want this nice black mamba." Isiah then pinched Shannon's nose so she couldn't breath. She held her breath for as long as she could, but eventually opened it for a gasp of air. In addition to air, Isiah's penis jammed into her mouth. "There ya go, girl," Isiah said. Paul continued to pound Shannon's rear as Isiah filled her face. Max watched intently as Shannon had a penis enter and exit from both ends. Herbert and George fondled her dangling breasts which swayed with the rocking motion of her body. Paul came first and pulled out limp. Isiah was still going full force into Shannon's mouth. Herbert quickly replaced Paul as they switched off more smoothly the second time. Herbert pulled off his wide shorts to reveal layers of chubby skin. Underneath that skin, though, Herbert's penis was only second to Isiah's in thickness. Shannon produced a muffled yelp as he put a condomed penis into her. Shannon's body was sweating buckets, and her vagina was producing a river of moisture in response to three penises having hammered into her. To Shannon's shock her body was getting really turned on. She had never been penetrated so intensely for so long. Her body was beginning to climax. Isiah climaxed first though, squirting his juices into the condom in Shannon's mouth. Isiah pulled out and they put Shannon's head back on the ground. With just the sensation of Herbert into her vagina, Shannon climaxed... her vagina clenching in orgasm around Herbert's penis. In response he came and ejaculated. "Oh fuck," Shannon mumbled into the grass. Her body shook and gasped in celebration. "Look at that," Isiah said. "Max, your girl likes to be gang banged." "Isn't she a dirty little cunt?" "Yeah," Paul said. "I'm ready for more. Anyone mind? Excellent. Roll her over. Got doggy-style down, I think I want a little flat on the back action." The men rolled Shannon over. She was getting exhausted and made some useless flailing motions, but they posed her like a doll. Paul put on a fresh condom and pulled her hips upward towards him. "You ready for this pretty little mouth, George?" Isiah asked. "Don't mind if I do. You're a gentleman and a scholar." Isiah and Herbert raised Shannon's back until her head was off the ground. They tilted her back with her chest pointed to the sky and her loose braid trailing the ground. George put on a new condom and placed his head against Shannon's lips. This time they just pried her mouth open with their fingers and George got in no problem. Again Shannon was being penetrated from two directions, but now she was being held suspended in the air, her back toward the ground, two jiggling breasts towards the sky, and only her feet touching the ground. Max watched appreciatively as one man was between her legs, another man had his penis in her face, and two others each held her back up and an arm each out so she couldn't effectively struggle. Paul between Shannon's legs held on to her hips to drive into her vagina more deeply. George held Shannon's head with one hand as he guided his penis deeper into her mouth, and with the other he fondled a breast glistening with sweat and sunshine. Paul finished first, but was quickly replaced with Isiah between Shannon's legs. Shannon whimpered in despair as her vagina so desperately wanted a break. Her jaw was exhausted too, but George continued to snake his penis down her throat. Isiah kept Shannon in her elevated position as he penetrated her vagina for the first time, though he was the fifth successive penis to do so. George came next into Shannon's mouth. They let the fatigued girl drop her back down so only Isiah held up her pelvis as he penetrated her. Soon Isiah came, and the pulsation of his large penis caused Shannon to orgasm again. "Fuck... dammit... aaagh..." she moaned from the ground. Isiah pulled out and then lay the blonde limp on the grass. "Maxy, I think she likes it," George chuckled to Max. Herbert had one last go - doing Shannon's limp body missionary - and the four were done. They thanked Max and Shannon, who didn't respond while panting on the grass. Then the four left for their respective cars leaving Max alone with Shannon. Max kneeled next the exhausted blonde, limp on the grass. She had lost one sneaker, and her jersey was pulled up and just hung around her neck. Sweat glistened over her body. Her legs were spread apart showing a wet vuvla, aroused and raw. Since they all used condoms, none of their fluids were on her. It was just the smell of Shannon and sex. "God, you're so sexy," Max said. "Dammit, Max, I'm never doing that again. I hope you enjoyed it, because it's not going to happen again." "Then you shouldn't have agreed to 'anything'. The anything is still open for today. I think there are some others people I want you to fuck." "Aw... please Max. Don't!" Shannon whimpered from the ground. She tried to close her legs, but her soar pelvis preferred to be open. "Are you saying no to me?" "Fuck, Max... no... I'm not saying that." she said looking away. "Just please... please don't make me." "Okay, no more fucking others today. But, you're not done yet," Max said pulling down his shorts. Shannon looked warily at Max's penis. She was so sore, but she also wanted to give Max what he wanted. "Oh... ouch..." she grimaced as Max penetrated her, while she lay on her back. He slid in slowly, sensitive to her condition. "You're cunt's already warm for me. And it's so loose already." "That's because... ow... you're the fifth guy to fuck me... ungh..." Max suckled on a breast. Shannon grit her teeth, because they were sore too. Max slowed the motion of his penis into and out of Shannon until his shaft was drenched with her fluids. He then withdrew and put two fingers into her vagina. Shannon closed eyes and concentrated on the good sensations while trying to block out the raw pain. A new sensation startled her as Max put his wet fingers into Shannon's anus. "Hey..." Shannon said trying to move her anus off of Max's fingers. "You don't have to fuck anybody else today, but I'm tapping your ass, girl. That's something you specifically said I could do." "God dammit..." Max rolled Shannon over, and spread her butt cheeks apart as she lay on her belly. Slowly, he forced himself into her anus, as she continued to lay limp on the ground. She whimpered into the grass, but made no physical move to stop Max from violating her anus. Shannon's fist clenched as Max made it halfway into her, introducing all new pains to her body. Max then slowly worked himself in until he worked her open enough for easy motion. "You're tighter than Nina is... your ass feels so fucking good." "Thanks... Nina likes it... back there... I don't let... people fuck me... there." "Except for me right?" "Except for you... only you can... shove your cock... in my ass." Max didn't last long. After watching Shannon get done from every direction, and now being in her tight rectum, he shot a heavy load deep into her. She sighed with relief as he pulled out. Max got Shannon's clothes and she gingerly put them back on. Shannon started walking slowly back to the car, but seeing her struggle, Max picked her up and started to carry her. "Thanks," she whispered into his ear. "No problem. You were great this morning. It's the least I can do." "Well, enjoy it, because I'm not doing that again." "You're not going to get gang banged or you're not going to fuck other people when I tell you." "Either." "So you don't care about the extra four thousand dollars you made today? And this is on top of the $650 we agreed on this morning." "What?!" Shannon asked perking up as they got to the car. Max placed her into the Cadillac roadster. "They each paid a thousand dollars to fuck me?" "They each paid two thousand. We struck a deal before we came into the bushes. I'm taking my cut of course. You get half. Unless you don't want it. You did agree to do anything for six fifty." "No, no, I want it. Wow... they paid that much?" "These guys have a lot of disposable income. They'd pay good money for a good piece of tail. And that's what you are, sweetie. I know a lot of guys with cash flow like them. Just let me know if you want to make a buck." As they drove away Shannon chewed on her finger in thought. "Holy shit... I could be a high class call girl and you'd be my pimp?" "I guess so." "That'd be da bomb!" THE END