The Will Ch. 03

PUBLIC BETA

Note: You can change font size, font face, and turn on dark mode by clicking the "A" icon tab in the Story Info Box.

You can temporarily switch back to a Classic Literotica® experience during our ongoing public Beta testing. Please consider leaving feedback on issues you experience or suggest improvements.

Click here

“And, I’m Carol your sister.” Carol said. The rest of them were introduced and Hillary and Bill joined the family for the rest of their breakfast.

“Before I give out the envelopes for today’s events I need to have a discussion with Hillary. Would you please excuse us?” Bill said while standing to lead Hillary to the small office next door.

“I think I can convince the rest of the family to include you as an equal family member in the events going on this week if you go along with my plan.” Bill said wondering if she would by in.

“I’m sorry. I’m not sure what you are talking about.”

Bill took the next ten minutes explaining to Hillary the rules of the game the family had been playing except for the specifics of what they had to do to get this far.

“What kind of things did they have to do?” Hillary asked nervously.

Bill took a breath. “Sexual things.”

It took a minute for the words to sink in. “With each other?” She asked shocked.

Bill shook his head yes.

“No way.” She said still not believing what she was hearing.

Bill again shook his head yes. “Whoever makes it through the week will be favorably positioned in The Will.”

Hillary thought about her own life at the moment. The divorced had left her with little money to live the life she wanted. She didn’t know these people from Adam so what difference would it make if she had sexual relations with them. She was not that experienced in sex so maybe this would widen her sexual horizon.

“What do you want me to do?” She asked with a smile.

Bill told her and she paused before answering. “OK with me as long as it’s OK with them.” Bill took her hand and they walked back to join the family.

The family again got quiet as Bill spoke. Hillary looked down at her feet.

“I would like for Hillary to catch up to the rest of you if it’s OK with you.” Bill asked.

“Catch up? Shit. I’ve walked naked in a jungle. Been caressed and sucked by someone unknown to me. And last night had intercourse with a woman on the other side of a wall. How is she going to catch up so quickly?” Mark asked noticeably pissed off.

“Mark. Let’ hear what Bill has to say.” Carol said trying to calm down her husband.

“I propose that Hillary does whatever you want her to for the remainder of the morning.” Bill said while watching their faces.

“What do you mean by whatever?” Tom asked. He sat up thinking about the possibilities that could happen with this good looking woman.

“Whatever. Short of pain.” Hillary answered. “I’m yours for the morning.”

“How will it work?” Carol asked. Her session with Alana yesterday warmed her body.

“Everyone goes to the large gym room. Mats will be placed around the room for you to sit on. Hillary will be on a mat in the middle of the circle. She will do what each of you command.”

Hillary suddenly realized she would be with another female for the first time. Sex with a man would be no problem but she was not sure how she would react having sex with a woman. She thought about the money and took a deep breath.

“OK with me.” Jesse quickly replied. Maybe he would be able to fuck her. Why not? She had to do what he wanted right?

Tom looked at Ann and Jena who smiled back at him. “Count us in.”

“Us too.” Carol answered without giving Mark a chance to reply.

“Good. If everyone is finished with their breakfast lets all head to the gym.” Bill said excited that everyone will see each other perform sexually for the first time as a group.

No one said a word as they walked into the large room with the mats already arranged for them. Hillary’s knees shook as she slowly walked to the mat in the middle and stood. She was wearing a short sundress with only white lace bra and bikini panties. She now wished she had worn sexier undergarments.

“I have a question.” Tom asked excited. He looked at Bill.

“Sure. Go ahead.”

“Can we ask her to do things with more than one person?”

Hillary realized what he was asking. “No.” She answered quickly.

“Yes.” Bill replied. “Anything short of pain.” Hillary knew he was right.

“How do we start?” Jesse asked impatiently.

“Hillary gets to choose the order.” Bill answered. His heart was beating faster as they all sat waiting for things to get started.

Hillary whole body was sweating with desire as she looked around the room. She had not had sex for over two years and today she was going to have about three straight hours of it. She turned around three times before she made her first choice. She pointed to Mark.

Mark coughed when she pointed at him. Shit. He didn’t want to go first. “Do we only get one turn?” Mark asked.

“No. You have three hours.” Bill replied.

“OK. I think I would like to see her take all her clothes off.” Mark chuckled.

Hillary gulped. She had never been naked before anyone but her husband, her doctor and a few ladies at the gym where she worked out. Now, she would have to take off all her clothing for strangers. Her fingers trembled as she closed her eyes and pushed the shoulder straps of the sundress down her arms. The dress fell off her bra covered breasts and down over her hips. Her body glowed bright red as it fell at her feet.

Jesse sat forward while watching this woman strip naked before his eyes. He could see the dark shadows of her nipples through her bra and her dark bush through her panties. His prick was hard and ready to go. Why didn’t she pick him first?

Hillary didn’t know which to pick first her bra or her panties. She felt shy about showing her breasts because they were only size 34 Bs. She could tell the other women were bigger than her on top. She surprised them all when she pushed down her panties over her pure white hips and down to her feet. She kicked them and her dress aside.

I should have trimmed my bush. Hillary thought as she reached behind her to release the bra snap. Her fingers froze and held onto the straps until she got enough nerve to let them go. The bra quickly fell off her creamy mounds and her tiny hard rosy nipples. She stood naked looking at Mark. He smiled which made her feel good. She again turned around to select the next person. She stopped and pointed at Ann.

Ann was not ready to tell this woman what to do. “I don’t know.” She said. “Can you skip me and come back?”

“No mom. It’s your choice.” Jena quickly replied.

Ann knew she had to choose something sexual but did not want to get involved with the woman herself. There was really only one choice. “I want you to touch yourself all over and then between your legs.” Ann said softly.

“What? I can’t hear what she said.” Mark said from the other side of the room.

Hillary turned to him. “She wants me to touch myself all over.” Hilary again froze for a moment. Not only was she the only naked one she would now caress her body and masturbate in front of them. They were making it tough for her but she was determined. The only way she could do this was by pretending she was alone in her bedroom like she had done for the past two years. The wetness between her legs would soon give her away but it didn’t matter because in her mind she was alone.

Tom’s prick pushed up painfully at the zipper in his shorts. Her body was very well proportioned and even though her breasts were not very large they matched her slim waist and narrow hips very well. His hand slid down to gently stroke his bulge while he watched her fingers start at the top of her head and slowly move downward. The fingers moved over her face and down her neck. She teased by faking a motion down to her breasts but instead moved over her shoulders and down her arms. The arms raised as her fingers moved underneath to the delicate skin, down to her armpits and to her sides. She hesitated and slowly brought her hot fingers up and over her firm cones to her rigid nipples.

Even Jena was breathing heavy as she watched her new Aunt toy with her pointy nips. She looked down to see her own nipples hard and begging to be touched. Heck why not? She asked herself before her fingers moved up to copy what Hillary was doing. She moaned softly at the same time they all heard a low sound of pleasure rise up from the naked woman’s throat.

Thomas took more pleasure watching his family’s reaction to Hillary’s self caresses. He could see Tom and Jena touching themselves and Jesse almost ready to prance onto the mat in front of him. He realized he was doing the same thing as his son as he squeezed his hand around his shaft.

Hillary’s body glistened under the bright overhead light that only shined down on her. The rest of the family sat back in the shadows looking, staring passionately at her. She knew they all wanted to ravish her body, to touch it like she was doing now, to kiss it and suck it and even fuck her. The thoughts drove her fingers quickly down to her dripping hairy pussy and deep into her furnace. Her knees were too weak to hold her up so her body slithered down to the mat where she fell onto her back with her legs spread wide. Her fingers flicked across her clit and she cried out. “Ohhh!”

Mark had the best seat in the house because her opened pussy lips were directly in front of his face. He watched her pink fingernail polish split the thick hairs apart before her fingers rapidly flicked up and down her pussy. That’s when she came. Hillary somehow managed to keep in her screams as she climaxed. Her body twisted and turned and her hips shot upward towards the bright light. Suddenly it crashed back down.

“Holy shit.” Jesse exclaimed. A wet spot had formed on the front of his pants.

Hillary came back to earth and sat upward closing her legs. She looked at Mark and smiled. She stood and looked at Bill. “How much time left?” He looked at his wristwatch. “A little over two more hours.” She wondered if she could make it without having a heart attack.

Hillary stood again and slowly turned. She wanted some action and knew Jesse was ready to give it to her. She smiled at him and he jumped from his seat.

“So what do you want me to do?” She purred as he stalked towards her. He slowly walked up to her and whispered in her ear. She listened and moved back from him and acted shocked. “You want to do that to me?” The rest of them laughed. So did Jesse when he realized she was only acting.

“Can I undress you?” She asked. He shook his head yes and stood tall waiting for her.

Hillary could see the large bulge in his pants and decided to tease him as much as possible. She pulled off his shirt and his sandals. Her fingers played with his belt and slowly released the catch on his pants. The room was completely silent except for the sound of his zipper as she slowly pulled it down trying not to touch the tent.

Jena was now the one sitting forward to see what weapon her cousin was packing and it looked to be pretty big. She now envied Hillary as she watched the woman pull off his pants and grab a hold of the waist band in his boxers. “And now I present to you…..” She hesitated and suddenly jerked his boxers down over his hard-on and down his legs. His prick popped outward and stood up proudly. “Damn” she mouthed when she saw the size of it. He was much bigger than her ex.

“Take it easy because it’s been a while.” She whispered in Jesse’s ear as she moved down on her back. Jesse knelt down at her feet and looked down as her legs slowly opened.

Carol’s own pussy was dripping as she watched her son move his long shaft down towards the hairy well of her new sister. She was sitting next to her brother and saw him squeezing his own hard-on. Her hand moved over to push his away and take over the caressing. Tom watched his nephew’s prick sliding slowly into Hillary’s furry mound.

At first his long and thick shaft caused her some discomfort but Hillary’s juices and body made a quick adjustment. “Oh yes.” She moaned as he buried it to the deepest part of her womanhood. Her legs wrapped around his body and she held on while he quickly fucked in and out of her. But, Jesse could only last about six strokes before his body tensed and he came, and came and came.

“Sorry, I….” Jesse stuttered as he pulled out of her dripping hole.

“It’s OK.” She said giving him one last kiss before he stood up off of her. Hillary looked over at Bill.

“Hour and 45 minutes.” He said.

Hillary was really starting to like this game. But, Jesse did little to fulfill her spent up desires. She needed more. She didn’t stand up all the way but instead remained on her back when she reached her hand over her head and pointed to Tom. “Are you ready brother?”

“He sure is.” Carol answer letting go of his shaft. All eyes were on him as they watched him get up from the mat and walk over to stand over her naked body. She was his for the taking.

Ann was somewhat jealous seeing her husband getting ready to fuck this woman. She knew he was fooling around with the others but she didn’t have to see it happening. She was looking down when she felt someone reach down and grab her arm. It was Tom and he wanted her to join him on the mat. “Me?”

“Yes. Come and join us.” He remembered their threesome with Alana and wanted it again.

“In front of everyone?” She whispered to him as she stood. “Yes.” He whispered back.

Tom led Ann to the mat and slowly removed her clothing. Hillary was nervous while looking up to see Tom strip off Ann’s panties. Her pussy was shaven. She wondered what Tom would want her to do. It didn’t take him long to position Ann on her back on the mat next to Hillary. Tom leaned over and whispered in Hillary’s ear. “I want you to get on your hands and knees and kiss my wife’s pussy.” Hillary just looked at him. Kiss another woman’s pussy? She had never even touched another woman’s vagina before.

“I don’t think I can.” Hillary said looking past Tom at Bill. They all froze and turned to look at the family lawyer.

“Oh, I think you can. Try it I’m sure it won’t be so bad.” Bill answered.

“She doesn’t have to.” Ann said feeling bad for the woman especially in front of everyone else.

“I’m afraid she does.” Bill responded. This time all eyes turned and looked at Hillary.

“I will try but…OK let’s do it.” She said. Hillary moved down between the woman’s legs and looked down at the bald swollen lips.

Ann watched her move her face forward until her lips were directly above her steaming slit. Her legs opened wide to give her an easy pink target. Hillary slowly dropped her mouth down until her lips touched the top of the wet slit. She planted a light kiss on it. Maybe if she kept her mouth closed she thought. Her lips were squeezed shut while moving them around the swollen outer lips.

Tom pulled off his briefs and saw what she was doing. He figured he would at least get to fuck another woman as he dropped to his knees behind her and aimed his prick at her opened pussy under her ass. He didn’t give her any warning as he rammed his shaft deeply inside of her.

Hillary’s mouth opened wide when she felt his long penis moved deep inside of her. Ann’s wet pussy smashed against her teeth and tongue. As Tom pulled back Hillary kept her mouth where it was. Her tongue moved on it’s own to explore another woman’s dampness.

“That’s it.” Carol cried out seeing Hillary’s tongue sliding into Ann’s pussy. She remembered how nice it was when Alana went down on her. Maybe she would soon experience the same thing?

The only sounds in the gym were Hillary’s and Ann’s moans each time Tom drove his body forward. Flesh slapped against flesh and a wet mouth smacked against a dripping pussy. “Oh yes. Fuck me!” Hillary cried as she felt her body ready to come again. She cried out loudly as she exploded. Tom grabbed her hips and pushed deep inside her to fill her cavity with his juices. Her body fell forward on top of Ann’s.

“An hour left.” Bill chuckled as he watched Ann and Tom move away from her. Hillary opened her tired eyes and looked around to see who was next. She realized there were two women. Carol and Jena. She looked their way. “Want to do it together?”

“Sure. Why not?” Carol said pulling off her clothing. Watching had raised her body heat to a new level. She pushed down her damp panties and turned to see if Jena was ready. Jena was already naked and was sitting on the mat next to Hillary.

“What do we do?” Jena asked looking at her Aunt.

“We don’t do a thing. She does it all.” Carol said lying down next to Jena. Jena smiled and joined her Aunt.

Hillary gathered up the energy she had left and moved up to her knees. She knew she had to use her mouth and her fingers to please them both at the same time. “Open up.” She ordered and watched as two new bald pussies opened for her to please.

Bill wanted in on the action as well but knew it was not time. He had planned it for him to make his grand appearance on the seventh day. When he planned this week he had no idea his family would completely go along with his devilish agenda. Now one of his daughters had her head between the legs of his other daughter while her fingers finger-fucked his granddaughter. Shit. Things had turned out wilder than he had imagined.

It didn’t take Carol or Jena much of Hillary’s tongue or finger to come up to their climaxes. Carol looked over at Jena next to her and made eye contact. Both of them moved their head towards each other until their mouths locked together.

“Twenty minutes.” Bill announced looking at the naked women who held back their pleasures a little longer.

“Hey. Don’t I get another chance?” Mark asked. Hillary’s ass was lying down in front of him. He looked over at Bill. Bill smiled and shook his head yes. Mark quickly stripped and jumped down on Hillary’s ass. Hillary’s mouth was too busy to move away and tell Mark his aim was too high. His hard penis pushed into her rear opening. Shit. He was fucking her in her ass and she wondered if he really knew it.

Mark didn’t care what he was fucking. His short shaft was pushing into a tight hole and it felt really good. His eyes were locked on Hillary’s fingers as they fondled Jena’s young pussy. “OH SHIT!” Mark yelled as he came. Carol and Jena heard his excitement and soon followed. All three were crying out in joy.

Hillary felt Mark’s hot liquid fill up her backside as she heard the screams of the women she was pleasing. She smiled as she fell down face forward between the two females. Her body didn’t have another ounce of energy. If anyone could be fucked to death she was close to it. Her eyes closed and her body drifted off into a deep sleep.

“I think she has caught up.” Tom chuckled looking down at her body with white come oozing out of her body cavities. “Welcome to the family sis.” Everyone smiled and walked out of the gym. It was time for lunch and they had worked up a good appetite.

They were almost through with lunch when the door opened and Hillary staggered in. “God. I am so hungry.” She said walking to the table, grabbed a slice of bread and crammed it into her mouth.

“Good, build up your energy because the day is just starting.” Bill laughed as he opened his briefcase and reached inside to pick out only one envelope. “Since everyone will be involved doing the same thing we don’t need to keep it secret.” He tore open the envelope and read it out loud.

“Today the women will be the hunted and the men the hunters. All the women includes the employees…” Bill stopped and looked at Sati, Utam and Alana standing smiling by the kitchen door. “whl will get a thirty minute head start to leave this room and hide. Each woman will be given a flag belt.” Bill reached down into the briefcase and pulled out a small belt with a piece of cloth attached to it with Velcro. “You will have two hours to hide out on the island anywhere you want and try to prevent a man from getting your flag. You cannot return to the dining room until the two hours is up. If a man gets your flag you must submit to his desires and then return to the dining room. The man with the most flags will win the game. Each woman who returns with a flag will also win.” Bill stopped and looked up. “Any questions?”