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."