3 comments/ 32600 views/ 1 favorites Risky Proposal By: evershot Exciting wasn't the word Jason Lee would use to describe his career. Being the youngest partner in the firm at thirty two, which was quite an accomplishment in property law. As a partner one would think that Jason would be well respected, but he knew he was often the butt of jokes. Small time was the snide nick name they had given him. He took it in stride, thought. His work was always solid, on time, and he held some very big accounts. It was because of those accounts that they had assigned Sara McVety to him. She was smart and hard nosed, but those weren't the qualities that made her dangerous to him. It was her charming and warm presentation. He had to give her credit she was good at reading people, clients would often ignore him when she was there, clients that were very important to his status as partner. Last quarter they had showed told him that he was steadily bringing in less money for the last two quarters. He wasn't worried. However, the pressure was there. It was this thought that had wedged a knot in his gut. A feeling that was eating at him as he sat in the conference room watching Sara present another compelling presentation to a new client. "Well, I'm sold!" the client said, as his eyes were locked on Sara's ample cleavage. "Thank you Mr. Baxter," Sara said, as she leaned forward sliding the contracts toward the client. When she turned the client stare was fixated at the beautiful view she was displaying. He gave a leery smile as he sauntered out of the room. Sara flopped down in the chair next to Jason and let out a sigh, "What a total perv!" "Well, you were playing up to him," Jason said. "That's not true." "Didn't you have that blouse buttoned all the way up this morning?" She blushed and quickly started to button up again. "That doesn't mean he isn't a perv." "Does that make me a perv?" She playfully punched him in the shoulder. "It shows that you have a pulse Mr. Lee." He smiled at the fact that she still called him Mr. Lee. She was one of the few people in the firm that respected him. She had came to his defense when the partners had warned him about his earnings and she never tried to steal any of his big clients. She worked hard to get new clients, he had often seen her work late at nights and knew her work was as solid as his. "Why do you -- " he said, but stopped knowing that the question might make her feel uncomfortable. "No, go ahead," she said. "Why do I sell myself like this? How else am I going to land those big accounts? I'm thirty five, Mr. Lee and I only bring in a fraction in earnings that you do. I was working my ass off for years in this firm hoping that they would make me partner. When I heard that they were going to expand the property division I thought I was finally going to get the offer. Instead we merge with a small no name firm and I take a back seat to you." He winced and shifted in his seat. Old wounds were bleeding again. "I'm sorry Sara, I didn't mean to --" "Stop it already." She stood up and looked down at him. "That's the worse part of all of this. You actually deserve to be partner. You put in the time most partners let their associates do. You know more about property law than anybody in the firm. I can't stand it when people say that your only partner because of circumstances and I really hate it when they call you small time. You are the top earner in this firm. If anything you did this firm a favor by staying on as a partner. Your clients stick with you because they know you are just that damn good." She paused, cheeks flushed, she took a breath to compose herself. "I should be the one asking you -- how do you do it?" He see her seething, he never knew she was this frustrated. He sat back and thought about his next move. She could be a very important ally in this firm but she could also be his down fall. He looked at her, she was being honest. "Are they pressuring you as well?" he asked. "They told me that I would have to earn at least seventy percent as much as you in order to make partner. It would take me years before I could even earn half as much as you. I'm already doing everything can. I've sacrificed my social life, I've missed birthdays, weddings, my sister already as three kids. And yet you've already attained everything I'm striving for." He stood up and motioned her to follow him. As they walked back to his office he uneasy, but he knew he needed to make a move otherwise the other partners would find some other way to force him out. Once closed the doors to his office he knew it was a risk he was going to have to take. "Why are we here?" she asked. "I have a proposal for you. How far would you go to get a big client?" She pulled back, face twisted with scorn. "Wait let me explain." He walked behind his desk and sat down, trying to keep his distance from her. "You already know that all these clients talk to each other and if you get one of them your reputation with that client will drawn in more big clients. Now my proposal is a simple one. I'll introduce you to my first big client and you help me establish a steady stream of new clients." She had a stern look on her face. He had already knew that she had filed a sexual harassment suit against an associate that had gotten that associate fired. Even thought she played up her sexuality for clients, she did not play nice with frat boy antics. "What do you mean how far would I go?" "It means that when you meet this client you will do whatever it takes to make this client trust you." Her stone exterior did not break. "Who is this client?" "I can't tell you that. I can assure you that she is very picky with the type of people she trusts and that she will test you. So I ask you are you willing to do anything to please this client." He watched her think out his proposal. He had purposely let it slip that the big client was a female, hoping that this fact would ease some of her very valid concerns. After what felt like an eternity she stood up, face still stern but with the posture of confidence. "Fine, it's a deal you introduce me to this client and I help you gain new clients, on one condition. Nobody ever learns about this meeting or deal." "She wouldn't want it any other way." He stood up and held out his hand, she shook it with a strong grip. "Meet me here tomorrow, wear something conservative -- no perfume, no blouses that show any cleavage and no skirts that highlight your amazing ass. Think nun in a business suit." She nodded, walked toward the door, before left she looked back at him. "Mr. Lee?" "Yes?" "So you think I have an amazing ass, huh?" She gave him a wink and waltzed out. *** The next day Jason sat in his office watching the clock. His office door opened and Sara walked in smiling. She had on a tan pantsuit that seemed one size too big. "Is this austere enough for you?" He walked up and inspected her. "Lose the make up." "What, you did not say anything about no make up." "Just go take it off and meet me at my car. We can't be late." He took off for his car not waiting to hear her response. He knew he had to trust her but her last words last night made him feel uneasy. It was a the type of comment she usually reserved for her clients. Was he being played? The car door open and Sara slid in with her game face on. Her blonde her was up in a bun and despite having no make up on Jason still thought she looked beautiful. She held up her hand. "Not a word. Drive. Now." As they hit the road he could see her looking out watching familiar business watering holes known for high powered meetings pass by. It wasn't until they were on the highway did she start to give him a look of concern. After a couple of miles she turned to him. "Country club?" "Don't worry about it. She is very private." After a couple of minutes they pulled off the highway and took a country road that seem to go into the middle of corn fields. An iron gate pulled into view and Jason rolled down the window and pushed the intercom. "Ms. Johnson? It's Jason Lee with my associate Sara McVety." "Bring visitors are we?" a voice on the other end said. The gate open and they drove in. A well manicured lawn and garden greeted them, but they were only a prelude to the mansion that was at the end. They parked in front of a garage and made their way to the front door. Before he rang the door bell, he looked at Sara. "Remember she will test you. If you don't want to do something just say no." "But I'll miss my chance if I say no right?" "Pretty much." He rang the doorbell and a butler answered the door. Wordlessly he guided them to room were a lady sat in a chair. She was dressed in a conservative blue dress with her hair in a bun similar to how Sara had her's. "Hello Jason, it's good to see you again. Have a seat." She motioned at the butler and he left the room. "Sara is it? Has Jason ever told you how he became my lawyer?" "No Ms. Johnson." "He became my lawyer because he earned my trust. Now my daughter is also in need for a good lawyer and I was inclined to refer her to Jason again, but he told me that there was another young lawyer that would benefit from my goodwill. Now, Jason knows how much I place on trust and he clearly thinks he can trust you. I ask you can I trust you?" "Yes, Ms. Johnson. I assure you that I will be able to -- " "That's not what I asked!" Ms. Johnson turned toward him. He knew what was coming next, he had thought that it would be Sara put through the paces, but he now knew that this would be an exercise on how much he really trusted Sara. And to be honest he wasn't completely sure he could, yet. "Jason, you seem to be over dressed for our meeting," Ms. Johnson said. Without a moment of hesitance, he stood up and began to take off his clothes. He kicked off his shoes and socks and took off his suit. "Stop," Ms. Johnson said as Jason was about to take off his boxers. "Face her." He turned and looked at Sara. She had the same stern poker face, but her eyes betrayed her. They were examining him up and down. His hairless chest and tone chest accentuated the v shape taper of his back. His solid midsection built from his dedication in the gym. He could feel his dick slowly becoming hard. "Sara, is it? Take off his underwear." Sara reached up and pulled down his boxers. His cock sprung, sticking straight out. He was a good seven inches in length and good six inches in girth. He heard a small gasp escape Sara's lips. "Oh, you have never seen him naked before?" "No, Ms. Johnson," she said. "I thought the reason why he trusted you was because you had shared his bed. This changes everything." Ms. Johnson got up and walked to a nearby cabinet and took out a small cigar box. "It makes me wonder why he thinks he can trust you. I now know it can't be an strong emotion such as love or lust -- the difference is debatable -- it must because you have a mutual goal or even something more rare than love...loyalty." She placed the box beside Sara. "Open it." Sara slowly opened the box. Inside was a ten inch crystal dildo and a bottle of lube. His heart sank, it wasn't uncommon for Ms. Johnson to use the dildo on him, but he was hoping she would not make Sara use it on him. Without being told he got on all fours. "Wait you want me to stick this in him?" Sara said, her voice had cracked, her facade had fallen and a look of total surprise was on her face. He held his breath this was the point of no return, either she would go all in or she wouldn't. Ms. Johnson raised her eyebrow and nodded. Sara picked up the lube and coated the dildo. "Don't forget to loosen him up with your fingers, my girl." Sara looked at Jason with wavering eyes. She lubed up her fingers and began to play with his anus, rubbing his opening gently at first coaxing him to accept one finger, and than two, and than eventually three. Their breathing had become shallower, faster and hotter. He couldn't believe that she was actually doing this. He felt that Ms. Johnson would somehow try to push her limits of decency, how easy those limits were broken were quite evident. He looked back and saw her biting her upper lip in concentration. With her free hand she began to trace light circles around his anus, slowly trailing down toward his balls, sending a shiver up his spine. He moaned. "You have a gentle touch," Ms. Johnson said. "Let's see how you handle the rod." Sara pick up the dildo, she glanced at him, but her eyes quickly went back to his ass. He felt the hard pressure against his opening, he exhaled and tried to relax. Slowly she began to stretch his opening, he felt the head push through sending another shiver up his spine. And than she did something he did not expect, she angled the dildo until it was pressed up against his prostate sending waves of pleasure through him. He looked back again and saw Ms. Johnson helping her guide the dildo. A small smile was on the edges of her mouth and her cheeks were a rosy tinge of arousal. "That's it my girl," Ms. Johnson said. "You've found his pleasure spot, keep at it. Watch his breathing, notice how it quickens as you massage the area. You don't have dig deep to find pleasure. Oh no, you've neglected his member. Yes, that's right, a little bit of cock play can go a long way. You can almost see him quiver with your touch. So my girl, what do you think of your boss' cock?" "Excuse me?" Sara stammered. "Well, I'm sure this is the first time you have ever handled his member. It may not be a monster, I have seen many monsters in my day, I find that it is his girth that makes me love his cock, wide enough to stuff any wanting pussy. Is it not?" "Yes," Sara said softly. "Oh my, I embarrassed you," Ms. Johnson said. "A deep seeded lust, perhaps? How is he as a superior? He must treat you well, seeing as your touch is every so light. Any resentment at all?" Jason felt the pleasing massage pause, he swallowed hard, not wanting to turn and face Sara. Surely there must be some resentment. Would she take it out on him now? "Yes, I see it now," Ms. Johnson said. "Past over were we, by this cock? Maybe a little retribution is in order huh? Time to stick to the boss." A surge of pressure shot through Jason as he could feel the dildo plunged to the hilt. Unprepared bowels let loose a mortifying groan and his ass squeaked out a little bit of gas. Ms. Johnson smack his cheeks. "Bad boy! You know better than that." Another involuntary moan slipped from his mouth. He dare not look back. The pilfering of his ass soon took a long and methodical rhythm and moans were replaced by grunts. After a couple of minutes he realized that Sara was grunting along with him as she plunged into him with controlled enthusiasm. He felt his cock begin to sway heavily and soon he was erect again. He felt the familiar snap of his cheeks being smacked again. A lighter touch than before. It must be Sara. Each smack became stiffer, harder, stronger. He risked a glance back and saw a wicked smile on her face. He yelped as one smack had finally sent a painful shock through his body. "That was for taking my job," she said. The dildo pressed against his prostate and he felt his throbbing cock caressed. A wave of pleasure. "That's for being worthy enough to deserve it." He could barely stand the ecstasy he was in, his cock was begging to be held, to find release. "Stop my dear, don't want him to cum so easily," Ms. Johnson said. The dildo slipped out of him, his head dipped in disappointment. Close but so very far. "Get up." He staggered to his feet his, ass burning red and cock pulsating for attention. Sara was flush and she shined lightly from a touch of perspiration. The wicked smile did not fade as he looked into her eyes. "You look too excited, Jason," Ms. Johnson said. "Some jumping jacks should help calm you down." He started the requested callisthenics. As he jumped up and down his cock began to flop around obscenely. Sara's eyes were fixated on his face, he found it difficult to to reciprocate the smile back. She was taking pleasure in his sexual frustration. "That's enough," Ms. Johnson said. "You two have a seat. I'll be right back." The each found their seat again on the couch and waited for her to return. He stared straight forward, unwilling to engage in conversation. He knew that her test wasn't over. She was the one to break the silence. "I guess I've been a real pain in the ass this morning, huh?" He laughed. He looked over to his associate. "It's okay, I've been a dick." "A very big dick." They both laughed. The whole morning seemed to slip into perspective. "What do you think she has in store for us next?" she asked. "You never know with Ms. Johnson. The first time I had met her, I spent an hour performing cunnilingus on her." "That doesn't sound too extreme." "It was during a conference presentation. My whole staff was there." "Well that's one way to seal the deal." "They didn't know I was there." "Why she ask you to do it?" "She didn't ask," he said. " I walked into the conference room determined that I would get the account. When I greeted her I just knew she was the type of woman that wanted control and I told her that with me should would have total control of her assets. I got on my knees went under the table and went to work." "Oh my god and you give me a hard time for selling myself.' "I know," he chuckled. " I'm a whore" "Glad to see that you are both in good spirits." They looked up and saw Ms. Johnson. "Follow me." She lead them to the front door, her butler opened it letting a breeze brush against Jason's nakedness. A black car was running outside and they got into it. They drove away from the tucked away mansion and back onto the highway. Sara was once again stern. To Jason's relief he notice that they weren't going toward the city. He remembered the one time Ms. Johnson had forced him to jack off in the middle of a women business luncheon in a busy restaurant downtown. He was so nervous that it took him a eternity to cum. He was so embarrassed that once the deed was done he ran out the back in shame. They pulled into a private golf course. Once out of the car the butler lead them to two golf cart and left them. Ms. Johnson got into one cart and they got into the other. Jason could see some women in the lobby pointing at him. Ms. Johnson waved at them and they politely waved back with leery grins. Sara drove the golf cart as they followed Ms. Johnson through the course. He noticed that only women were on the golf course. Each time they passed a golfer he received the same grin. They pulled up to the eleventh tee box and were greeted by two golfers. "Mother, well this is a pleasant surprise," a brunette golfer said. "Jason! What has mother got you doing now? Up to no good I see. Are you here to land another big account?" "You might say that Matilda," Jason said. He had met Matilda under many circumstances and this was his normal attire on each occasion. "I like to introduce you to my associate Sara McVety." "A pleasure to meet you," Sara said. "Well, I'll let you feel each other out," Ms. Johnson said. The other female golfer got into the golf cart with Ms. Johnson and they drove off, leaving the trio behind. "Do you golf?" Matilda asked. "Of course and necessary skill in our line of work." "Great, look in the cart, I'm sure mom packed a pair of golf shoes for you." Once Sara had her shoes on they teed off. As Matilda swung Jason caught a glimpse of her bare pussy. Game on. "You have a very nice swing," Matilda said as they walked up to the green. "Thank you, so do you." "I've been working at it. I'm still a little be tight in my follow through, which follows me when I putt, but I've found if I could relax my rear end more during putting, it real improves my stroke." She wiggled her ass at Jason and he knew what he had to do. He walked up behind her and got to his knees. He lifted her skirt and began to lick her crack. A half a round's worth of salty crack sweat with a hint of cherry body spray rolled onto his tongue. Risky Proposal "Thank you, Jason," she said. "Sara, it's too bad you're in slacks otherwise I would offer you some. He really is quite good. Why do you take off your jacket, it's warm out here." Sara took off her jacket and handed it to him. They both sank their putts. On the next hole, he was once again behind Matilda this time he spread her cheeks wider and gave her a good rimming. "Easy there tiger, don't want to make me too loose," she said. She gave his cock a small squeeze. "Let's make this interesting. If I win a hole, you have to place a golf ball into Jason's ass." "And what if I win?" Sara asked. "Call it." Sara leaned back and gave Jason a wicked smile. "If I win Jason has to cum into the hole." "I like how you think girl," Matilda said. "You better have eaten your spinach today, Jason. If you can't perform there will be a penalty." As they teed off, Jason was unsure of which golfer to root for. He was unsure if he would be able to take six golf balls in his ass and he was definitely sure he wouldn't be able to cum six times. When the approached the green he saw that Sara was away. She lined up her putt and drained it from twelve feet. She gave a small fist pump, which digressed to a jerking off gesture and blew Jason a kiss. Matilda putted and fell an inch short. "Come on tiger show me a hole in one," Matilda said. He massaged his tool as he walked up to the hole. He squatted at the hole and began to stroke in earnest. The warm sun bathed his back as he worked himself off. "Just tap it in, tap it in," Sara said. "It's all in the hips," Matilda chimed in. They giggled together as they watched him unleash one into the hole. Matilda let out a hoot and grabbed a towel from her bag. "A good golfer leaves the course as they found it," she said, leaving Jason to clean up his mess. As he walked back to the carts his cock hung loose between his legs, relieved from the mornings stress. "That will not do," Matilda said. She reached into a bag and produced a cock pump. Sara raised an eyebrow. Jason got the feeling she had never seen a guy use a cock pump. "I like my caddies ready to go." She tossed a tube of lube at him and he got busy lubing up his softened cock. He inserted himself into the cylinder and slowly pumped himself up, filling it up. "It looks so much bigger now," Sara said. "It takes a long time to see those results. Jason has certainly been practicing." Matilda smiled approvingly. "Keep it on until you need to rub one out." They played the next hole and Matilda easy won. Jason dutifully lubed up a golf ball and eased it into his ass, as he was peppered with hole in one punchlines. As they continued to play, to Jason's dismay Matilda won the next two, forcing him to carry three balls in his ass. To make matter's worse he felt his cock begin to strain against the cylinder. He was careful not too over pump the tube, but his years of cock pumping had made it easy for his cock to succumb to the pressure and stretch and fill the tube. He had now filled the nine inch tube and was straining to be released from his chamber. "Only two more holes to go," Matilda said, as they watched Sara set up for her tee shot. "Are you going to be able to make it?" "Sara will come through in the clutch," he said. "I take it you've had experience cumming through her clutch, huh?" "Actually no." "You've never touched that sweet ass?" "Nope." Matilda looked at Sara as she finished her follow through. "She must be a good lawyer for you to introduce her to our family, Jason." He shrugged. "What can I say? I take my job seriously." When they came to the seventeenth green Sara came through for Jason's aching cock and ass and sank another impressive putt. He quickly released the pump and shuffled to the hole. "The way you hurried to the hole one might think it was the first pussy you've ever seen," Matilda said. Jason squeezed his puffy and engorged cock at the base. He knew he had to prevent his cock from becoming flaccid after he came and he put on a cock ring he had found in another bag in the cart, Ms. Johnson had planned for everything this afternoon. "Clever," Matilda said. Sara was staring at his enlarged red member. He massaged the head of his cock. The prolong time in the tube made getting off a bit more difficult, it also didn't help that he had already blew a huge load three holes back. He began to milk this cock and play with his balls. "If you don't hurry up, you may be penalized for slow play," Matilda said. Sara gave him a coy smile and winked at him. "Come on Mr. Lee, milk that fat cock for me." He noticed that her blouse was unbutton showing him her ample cleavage. He felt the pressure build at the base of his balls and he squirted out another decent load. "Alright big boy!" Sara shouted. His cock remained heavy and thick this time, thanks to the cock ring. "Last hole," Matilda said, as she set up for her drive. It was a par five and both golfers were swing for the fences, landing on the green in two. Matilda was away and had eased her first putt three inches from the hole. Sara had difficult downhill putt, which skipped over the hole leaving her with difficult second putt. She gathered herself, found her line and putted. It rolled with good four foot left to right break and sank it dead center. "Great putt, Sara," Jason said. Matilda came up to her easy putt. The ball hit the lip and rimmed out. She cursed herself and cleaned up the hole. "I guess you get another chance to get off," She said, eyes twinkling with mischief. "Good game Sara, you really proved yourself out there." Jason gave Sara a thumbs up and trotted out to the hole. He took a deep breath, the fact that they were able to get on the green on two did not leave him a lot of time to recover from his last load. He hoped he would be able to rub just one more out. He started out with long slow strokes, focusing on trying to get the maximum pleasure on each stroke. Minutes passed and he was wondering if he would be able to let another one loose. "Remember the penalty Jason," Matilda said. "If you don't perform on this hole, I'll suggest to my mother that she should give her account to Sara over here." He began to stroke harder, knowing that Matilda was not one to joke about the deals she made. He stuck a finger in his already crammed ass and tried to massage his prostate. He wriggled his finger searching for the spot to push him over the edge. No luck. He jumped up and ran to the cart. He grabbed the lube and took a pitching wedge. At the hole he got on his knees and worked up the lubed handle of the club into his ass. "Playing it were it lies," Matilda said. "Come on Jason work your ass. " He tried to ignored the distraction and began to stroke furiously. He was so close. Just a little more. "Hey!" Sara shouted. He looked up and saw her standing there topless. Her breast seemed to defy gravity as they perched perfectly on her. Pink silver dollar nipples perked out begging for him to suckle them. She pinched them and gave him a seductive moan. He groan in wanting and he felt a surge rising from deep in his ass, he pushed the club deeper and his body shook and he felt his cock jerk and small creamy load squirted out. He collapsed, exhausted. "Good play, Jason," Matilda said. "Clean up the hole and meet me in the club house." He got up and watched Sara and Matilda drive off. He cleaned up his mess and drove up to the clubhouse. Walking through the clubhouse he was met with many grins and hellos. He had removed the cock ring, but his member was still very thick and long and stick straight out. Sara and Matilda were in the lobby drinking lemonade. Ms. Johnson was also there. They looked like they were enjoying a lazy afternoon. "Jason, there you are," Ms. Johnson said. "We were just finishing up business. Sara is going to be taking care of Matilda and you of course will continue to be my lawyer, as if there was any doubt. You always come through for me. I took the liberty of bring you your clothes and your car. I hate to rush you out,but management is getting anxious with a half cocked naked man wandering around here." He picked up his clothes and put them on as the girls talked about when they were going to play a full round of golf, a girls outing if you will. Overall the day had been a success, a bit stressful at the end, but Sara really helped him out in the end. As he straightened his tie Sara handed him a glass of lemonade. "You earned it out there," she said. He downed it quickly, parched from the sun and all the fluids he had loss. He thanked his hostess again and they walked out to the car. They pulled back onto the highway, a relax smile was still on Sara. The whole day had really proved to him that he could trust Sara and it had definitely brought them closer. "You did good today," he said as they drove the lull of the highway home. "I did good, you were superhuman out there. I didn't think you could top what you did at the house, but you did, under the gun even." "Well, I did have some help on the last hole." She blushed. "I couldn't leave you hang there. It was nothing." "Trust me, those are certainly not nothing." "Remember our deal nobody learns about what happened today." "Like I want to tell anybody I stuck three golf balls up my ass." "Where are those golf balls by the way?" He gave a sheepish shrug. "They're still up your ass!" She started to laugh uncontrollably. "Mr. Lee, I think you are the one with the amazing ass." "Call me Jason."