The Will Ch. 03

Suddenly Jena broke down in tears. She pulled her mouth away from his hard-on and sat up with her head in her hands crying. “What’s wrong with me?” She bawled.

“Nothing. Believe me.” Bill said trying to get her to stop crying. “Most men would cut off their left nut to fuck you.”

Jena stopped crying and looked over at his balls. “Really?”

“Sure.” Bill said happy she had stopped.

“You would cut off your left testicle to fuck me?” She asked.

“Yes.” He heard himself say. At this point he really believed it.

“OK then you'll have to do it.” She said smiling as she lay back down on the towel. She spread her legs wide.

Bill glanced down at what she was offering him. Never in his long life had he been offered something so wonderful and priceless. He thought about the plan. Fuck the plan he said to himself as he slid his body over to lie between her thighs.

Jena didn’t expect the older man to really do it. She had almost given up hope that someone would take her cherry soon before the week was over. Now, it was real as he aimed his hard tip at her entrance.

She is definitely wet enough Bill thought feeling her juices covering his crown.

“You sure about this?” He asked before lowering his hips.

Jena looked up with her baby blue eyes and smiled. She had a hunch and knew it was time to test it out. “Yes Grandpa I want you to be the first.”

Bill almost choked when hearing her words. How in the world did she know? Maybe she was just guessing?

“Grandpa? Your grandpa is dead.” He said in a panic.

“No...no. Don’t lie to me. I know you are my grandpa.” She giggled. Her fingers moved under his stomach to tickle the tip of his prick. It was still hard and ready.

“How did you know?” He said realizing he could not lie to her anymore.

“I just know.” She said smiling. “I can’t explain it. I feel it.” Her fingers made small circles around the moist tip.

“You have to promise me not to say anything to the others.” He whispered.

“I promise if…” She stopped.

“If what?”

“If you fuck me.” She giggled.

Thomas Simpson, alias Bill Patton, felt shivers up and down his spine as he slowly lower his hips driving his penis through her maidenhead. He heard her moan and stopped. “You OK?”

“Yes. Keep going.” She said. At first there was a sharp pain but it was rapidly going away and feeling better and better. All of her feelings were now in her vagina as his penis slowly and deeply invaded it. She felt his stomach met hers. He was all the way in.

“It feels so good.” She whispered as her fingers moved around his ass to pull him even tighter against her.

“I…know.” Thomas’ voice cracked. She had the tightest pussy he was ever in.

“What do I do now?” She asked.

“Whatever you want.” Her grandfather said. He took a deep breath of air when she squeezed her tunnel’s inner wall. “Oh!”

She heard his moan and squeezed his rod again. “You like that?”

“Yes dear.” He slowly moved his shaft out and slowly back in. This time she moaned. “Oh grandpa.”

“You like that?” He laughed.

“I never knew it would feel so wonderful.”

His hips started a slow in and out motion. Her body pushed up as he pulled out. It did not want him to leave. Her legs opened and her feet curled around his hips. She was a natural.

Jena moaned feeling his penis pumping in and out of her. Her eyes opened when he stopped and pulled out of her. “Grandpa, what are you doing?”

“We have to stop.” He groaned.

“No please. It’s OK. I’m on birth control.” She begged trying to pull him back down to her.

“It’s not that. It’s the deck. It’s too hard for my body.” He sat up and took her hand. “Let’s go down stairs.”

Jena noticed a small amount of blood between her legs. She quickly wiped herself as she stood and followed the well built older man down to the cabin below.

*****

Jesse, Carol and Alana knew they had to get back to meet with the others for lunch. Jesse was disappointed he was not satisfied but at the moment his goal was to fuck someone. So far the masturbation and blowjobs were great but he wanted to become a man.

*****

Tom couldn’t hold back because of the erotic view in front of him. His wife’s head was planted between the thighs of a beautiful woman while he pumped his shaft in and out of her. Each time he drove forward Ann’s face pressed against Sati’s pussy. They both moaned together. He cried feeling his hot juices flooding her womb.

*****

“Sorry honey.” Thomas said to his granddaughter. The time it took to move down the stairs robbed him of his hard on.

Jena at first was disappointed. “I can give you a blowjob if you want.” She grinned.

Bill looked at the clock on the wall. It was ten minutes until noon and he knew he needed to get back to the island. “Can I have a rain check?” He asked.

“Yes Grandpa.” She giggled. Bill grabbed his swimsuit to put it back on but she stopped him.

“Can we go back naked?” She giggled.

“Of course. It’s my boat and my island. We can do anything we want to do.” Tom said. “But I need you to do two things for me.”

“Yes anything.”

“First keep calling me Bill or Mr. Patton. Second, I need you to pretend to be a virgin when your father fucks you tonight.”

“Tonight? My father?” Jena asked surprised.

“Yes.”

Jena smiled as she thought of the blowjob she had given her father. “I think I can convince him.”

“Good.” Thomas smiled. His hand moved over her soft shoulder and fell down to gently caress her bare breast.

Thomas thought back a year ago when he flew to Europe to a world famous plastic surgeon that did a complete make over of his face and parts of his body. While his face and body was healing Tom worked with a trainer to get his body into shape. He lost the layer of fat around his waist and built up some bulk on his arms and chest. He was looking pretty good for an old guy. When he returned to the island only Sati knew it was still him and not Mr. Patton. She swore not to tell anyone not even her husband.

*****

Everyone was sitting around the lunch table waiting for Bill and Jena to get back from their mini-cruise. Bill walked in first and greeted everyone and about five minutes later Jena strolled in. She sat next to her father and smiled.

“Where were you and Patton?” Tom whispered smartly in his daughter’s ear.

“Out on the big boat.” Jena answered. “Now you worry about what I am doing?”

“Well. He is not really one of us.” Tom replied softly. Jena almost laughed at his remark but kept it in.

“He’s a nice man. You should get to know him.”

“So how was everyone’s morning?” Bill said looking around the room. He did not see the upset faces or stress except for Mark who seemed mad at the world.

“Where did you go?” Mark asked Carol sitting next to him.

“Alana showed Jesse and me a nice pond by a waterfall.”

“Is that all she showed you?” He zapped back.

“No. She showed me how to really enjoy myself. And, you know what? I did.” Carol turned and looked at Alana who was pouring water in her brother’s glass.

“The rest of the afternoon is yours but please be showered and back here at 6:00PM.” Bill announced. “I advise you to rest up.”

They all looked at him and smiled. Their activities tonight would be turned up another notch and they had better be ready for it.

Everyone took Bill’s advice and headed back to their rooms for rest.

None of them were able to fall asleep because of the excitement of what the night would bring. They all knew that with masturbation and oral sex behind them there would be some serious sex ahead.

Bill chuckled as he watched them all hurry to shower and dress. They were waiting for him when he walked into the dining room at exactly 6:00PM.

“I think tonight might separate the men from the boys.” Bill said suddenly realizing the hidden meaning. “Oh no.” He laughed. “I didn’t mean it like that.”

Good Mark thought as he took a deep breath.

“Here are your envelopes for tonight. Do not let anyone else see what they say and do exactly as they describe.” Bill moved around the long table and handed each one an envelope with their names on them.

Ann didn’t wait as long this time to open and read her directions. “Please proceed to the gym room A and follow the directions you find there.” She was not as nervous this time while she walked quickly down the long marble hallway to the gym room. She took a deep breath and pushed open the door. The room was empty except for another envelope on the floor. She closed the door and quickly ripped open the envelope. Naked again she thought as the read her instructions.

***

Tom did as the envelope said. He walked to the designated room and pushed open the door. In front of him was an empty room with an envelope on the floor by a wall that looked to be made out of a cloth material. Tom tore open the envelope and read his new instruction. “Remove all your clothing and when the room light flashes open the cloth flap in the wall and push your penis through the small hole. Do not remove it until the light flashes again.”

“What the fuck?” Tom said out loud. They wanted him to stick his prick through a hole in the wall and let someone do whatever they wanted with it. So far things had been pleasurable. He was starting to doubt it now. He had come this far and was not about to back off now. He jerked off his clothing and walked to the flap. Here goes nothing he thought as he saw the light flash. He pushed his semi-hard prick through the tight hole.

***

Jena giggled as she stood naked watching the pink mushroom head of a penis come through the hole in the wall. Her envelope said to get the penis hard by doing anything she wanted to it but to not let it ejaculate unless it was inside of her vagina. Her fingertips gently rubbed across the purple tip which quickly caused it to rise upward and outward. Her mind quickly came up with things she could do with her own penis. She put her hand over her mouth as she turned her body and pushed upward on her toes until her cute round ass rubbed against the penis. Her hand moved the tip up her ass crack and slowly back down. How does that feel daddy? She laughed to herself.

***
Jesse didn’t hesitate pushing his already hard prick through the hole. He was determined not to ejaculate early like he had done the past few days. He had thought about peeping through the hole to see who was on the other side but he knew it was against the rules and he could be disqualified. Right now he didn’t care who was on the other side.

*****

Carol was reading the envelope when a flap in the wall opened up and a long pink penis pointed through. She jumped back at first not expecting it and quickly finished reading her instructions. This will be fun she thought because she will get to touch and play with a hard prick and the person on the other side of the wall would not know it was her. As she stripped she glanced down at the instructions again. They said she could do anything she wanted but it could only ejaculate inside of her pussy. Damn. It was time for some serious fucking.

Her fingers quickly tested the moisture in her bald pussy and the results came back dripping wet. Fuck foreplay. She thought while she turned and pushed her ass up against the rigid digit.

Jesse waited for someone to touch his rod or maybe even give him a blowjob. He felt something brush against it and couldn’t figure out what it was. He smiled when his tip pressed against some warm flesh and then a hand curled around it. He gasped when the hand pulled his meat deeper into the cut-out hole and against something hot and wet. It was a feeling he had never experienced before. He suddenly hoped it was a……it was…..his penis was moving into a pussy for the first time. OH MAN. He moaned. He pushed against the moveable wall as hard as he could and felt his long prick move deeper into this woman’s pussy. He heard her moan when he was in as far as he could go. The wall prevented him from going any deeper. The rest was up to her.

Carol closed her eyes and walked backwards while letting go of the huge cock. It had to be either Jesse, or Tom’s, or even Bill Patton. She knew for sure it wasn’t her husband’s small penis as her pussy slowly engulfed his whole length. It was the first time she felt completely full. She moved slowly forward and back while trying to keep her balance. It was not easy fucking a penis sticking out of a wall.

*****
Ann touched the hard penis timidly at first. From what she had seen so far it had to be her brother-in-law Mark. The note said she could do anything she wanted to it. She had never seen a penis up close before so as she jerked her fingers up and down her face moved only inches from the tip. Her eyes moved up and away while her mouth moved forward to taste the juices forming on the tip. Her teeth scrapped along his crown as she experimented with new techniques. She heard him moan slightly as her lips formed a tight suction around the base. She giggled as she took hold of the base and pulled his prick hard through the hole. Suddenly his balls came through as well.

“Ouch.” Mark cried out when his balls followed his prick through the hole. He tried to pull them back out but it hurt. He was stuck. His pain quickly went away when a mouth took in one of his balls and then the other. “OH GOD!” He cried as the tongue flicked in circles around each of his testicles. He was about to come when her mouth moved away. For almost a minute nothing happened. Then he felt a hand pulling and aiming his penis at …..oh my…..her pussy. Her warm dampness surrounded his length. He managed to push forward and back almost ten times before he climaxed.

*****

Jena’s pussy was still a little sore from losing her cherry on her grandpa’s boat that morning but not so sore she couldn’t enjoy another penis deep inside her hole. Jena had no problem pushing her ass back with her legs wide until his tip was buried at her entrance. He was definitely bigger than his father she thought as her body pushed back against the wall. His long penis slid deep into her tight pussy.

Tom could feel how tight this woman’s pussy was. Could she be his daughter he thought? At least that’s who he pretended it was as he moved his prick in and out of her hot oven. He could hear her moan each time he pushed forward. This is even better than the glory holes he had heard about at the X-Rated Video booths.

“Yes. Fuck me Daddy.” Jena moaned. She wished the wall was not between them and that she could do it with him on top.

Tom heard her words and stopped his pumping motion for a few seconds. Shit. It was her. He continued to pump forward and back with more vigor.

“I’m coming baby.” He yelled feeling the damn burst. “Me too Daddy.” She yelled back. The whole wall was about to come down.

*****

“Oh.” Ann cried when Mark’s penis slipped easily inside her wetness. Her passion was on high while feeling another man’s penis inside of her for the first time. He might be smaller than Tom but he knew how to move it the right way. As his hips moved in small circles his penis rubbed on every inch of her pussy walls. Her fingers moved up under her ass to gently milk his balls. Her other fingers found her hard clit. “Fuck me.” She cried as she raced for a climax.

“I am!” Mark cried out in pleasure when he heard his sister-in-laws voice. “I am Ann!”

“I’m there!” Ann screamed. Her body flew forward at the same time his hot juices flew out the tip of his rod. Ann felt his warm pleasure splatter against her ass cheeks. She scooped up his juices and turned to rub it on his balls. “Some lubrication.” She laughed as he pulled his creamy family jewels back through the tight hole.

*****
“Don’t stop!” Carol cried out as she approached her climax. But he did.

Shit. It’s my mother. Jesse thought after hearing her voice. She said don’t stop. He laughed as he continued to do as she ordered. Always listen to your mother.

Carol’s whole body tingled when her explosion came. She now knew what it felt like with a large penis in her. Forget about those stories about how it doesn’t matter how big the ship is. A big ship feels a lot better than a dingy. She screamed and heard him do the same. It sounded like her son.

*****

The six of them took some time to calm down before they dressed and exited the rooms. They all managed to get back to their rooms without running into anyone else. Fucking through a hole in a wall took all the energy out of them. They all feel quickly into a deep nights sleep.

Day Six.

Bill got the phone call at 9:00PM and was surprised to hear the voice on the other end.

“Is this Bill Patton?” A woman’s voice asked.

“Yes.” He managed to say.

“Mr. Patton. This is Hillary Swan. I’ve been out of the country for over a month and just got back into town. Am I too late to come to the island?”

Thomas thought quickly. Hilary was a daughter of his that he did not find out about until about five years ago. Her mother was his financial assistant Betty who was his mistress for almost five years. When she suddenly left he just figured it was because he would not leave his wife.

“Well yes. It is too late. The rest of the family has been here for five days and it would not be fair to them if you only come in for the last two days.” He answered. Thomas had never met his daughter but had paid a detective agency to find out as much about her as possible. She had recently divorced her husband of 15 years and had one son who was in the military. He had hoped she would come but when she didn’t Thomas forgot about her. Until now.

“I would like to meet the rest of the family even if I don’t qualify for any of the will.” She said.

Thomas thought about it. “Sure. Come on down.” Thomas gave her a phone number to call to make travel arrangements. If everything went as planned she would arrive during breakfast. He spent the next hour revising the plan for the remaining days.

*****

Day Six

The whole family was sitting around the breakfast table talking like nothing had happened the night before. Jena had a grin on her face that wouldn’t go away. She noticed her father looking at her a few times and when she made eye contact he quickly turned away. Jesse also seemed different. The monkey was off his back and he was now looking for new conquests. He noticed Alana had rubbed her breast against his arm more than once during the breakfast. They all suddenly got quiet when Bill walked into the room. Next to him was a nice looking woman who was maybe in her mid-thirties.

“Good morning everyone. This morning I have a surprise for you.” He turned and motioned for Hillary to come past him. “This is Hillary Swan. She is one of you. Her father is the late Thomas Simpson and her mother was the late Betty McManus.” Hillary smiled.

The family sat shocked that she had now showed up. They all thought the same thing. They had sucked and fucked to get to this point and she gets to miss all the fun.

“I guess you are my aunt.” Jena said while moving over to Hillary and giving her a hug. But, Jena was the only one to give any type of warm greeting. Bill could see they were all upset and he knew why.

“Before anyone hangs Hillary let it be known she has agreed to not be included in the will because she had missed the first five days of this week.” Suddenly all their faces changed from anger to happiness.

“Hi. I’m your brother Tom.” Tom quickly said while joining Jena.