Gambling Weekend

by The Jint Fan

Caution: This Sex Story contains strong sexual content, including Ma/Fa, Teenagers, Consensual, Hypnosis, Drunk/Drugged, MaleDom, Gang Bang, Voyeurism, .

Desc: Sex Story: Harry James lost everything including his mother and his sister. His sister loses her virginity and mother is married off.

Harry James knew he was in trouble with his gambling habit. He watched the guy across from him closely. Chris Benoit was ahead of him by twelve thousand dollars. He needed to win this hand of poker or that's it.

Harry was sweating because he was holding only a pair of threes. He knew he had to bluff his way through it.

Chris raised his bet. Harry was on credit with him. He countered him. The cards were shown. Harry lost his hand. Chris was holding a pair of fours. Harry couldn't believe it. The other guy out bluffed him.

Harry almost started to cry when he showed the cards. He was in deep trouble. He owed Chris thirteen thousand dollars.

" Ok. Harry, you owe me thirteen.", Chris informed him.

" I don't have it.", Harry informed the man. He was a dead man. He knew it. He wasn't going to be alive when he left.

" You have something that could work. I have known you for the last ten years. Since you were eighteen.", Chris informed him.

" What do I have?", Harry asked. " I don't have anything that's worth that much."

Chris smiled, " Oh yes. You do have something. Two very special things and they will work out for payment"

" What?"

" Your mother and sister.", Chris informed him.

" You can't be serious. Not Kathleen and my mother!"

Chris nodded his head. " Then I will kill you! I'm no bank."

" Please something else.", Harry was begging for his life and his family. He didn't want Chris with them. Chris is wealthy and he can do anything he wants against his family. Harry didn't want him near them. Harry had no choice. He slowly nodded his head in defeat.

" I can't but I promise they won't know a thing. I will place them under hypnosis They will not remember anything. It will be just a dream to them. I just want them for one weekend of sex.", Chris informed him. " Full blown sex that is."

Harry had no choice. He had to do it. " Ok."

" I will contact you in a week with details.", Chris told him. He told him to leave the hotel and return to his house. He also told him that he was lucky to be alive. " Don't tell them or you are a dead man and I'll still have them."

Harry left the hotel room, where the gambling was being played. Harry didn't know what to do. He was going to have his mother, who is fifty-two and still married to his father and his fourteen year old sister would have sex.

Harry drove his car to his house. He opened the front door of the house. His mother, Beth was awake watching television. Harry asked, " Where's dad?"

His blonde hair mother looked at her son, " He's asleep. He had a long day at work. He is going on a business trip in two weeks."

" How long will he be gone?", Harry asked.

" Fourteen days.", a simple reply came from her lips. She seemed disappointed.

" Really?", Harry was shocked over the news. How did Chris know or did he?

Harry told his mother goodnight and went to his bedroom. He couldn't believe he was actually going to do it. He was going to let Chris to have them. Harry had no choice in the matter. He was in too deep with him.

Harry fell asleep after thinking about his mother, Beth and Kathleen having sex with Chris. He hated to say it but he wanted to see them fucked. Harry had fantasies of seeing his sister having sex. And his mother also.

Harry was reading his email when he spotted the email from Chris. Harry opened the email on his computer. The message said that everything would start on Friday afternoon at three afternoon. He wanted Harry to send the measurements and shoe sizes of both his mother and sister. Harry had until tomorrow afternoon to get the information.

Harry searched the closets of his mother and sister while they were out. Harry sent the information out to Chris. He knew it was over. It was going to be a long weekend.

On Thursday, a package was delivered containing two small vials of a clear substance. The note with the package was from Chris and they were directions on how and when to drug both his mother and sister the next day.

Friday came too quickly and Harry was there at the house waiting for the arrival of Chris. Harry watched as his mother and sister were talking in the kitchen sipping their drinks. The minutes went slowly. He wanted this to be over. It was taking too long.

He saw the stretch limousine arriving in front of the house. Harry watched as Chris stepped out of the car and walked toward the front door. Harry knew it was time. He walked to the front door. Harry opened the door. Harry spoke to him, " Hi."

" We ready?", Chris asked.

Harry nodded his head to him, " I gave them the drug. I slipped it into their drinks."

Chris asked the important question, " Are they asleep?"

" As of a few minutes ago, They were talking but getting tired. I don't think they realized they were drugged.", Harry told him as he walked into the kitchen.

Chris and Harry entered the kitchen. They watched as Kathleen and Beth are sleeping at the table. Kathleen's head was resting on table. Her hands acting like a pillow. Beth wasn't like her daughter. Her head fallen back as she slept in the kitchen chair.

" Good.", Chris smiled. " Go get my friends from the limousine."

Harry obeyed him and walked back to the limousine. He watched for a second as Chris was checking to see if they were asleep.

Harry walked to the waiting car. He knocked on the window. The door opened and Harry watched as a large man stepped out followed by a tall thin woman. Harry was amazed at the size of the man. They walked back to the house.

Chris met them at the front door. He instructed Harry to follow them to the master bedroom to watch them get Kathleen and Beth ready for the weekend activities.

Harry walked behind the two men and one woman. They entered the kitchen as Chris begins to use hypnosis. He was working on Kathleen. She nodded her head at the part of doing whatever someone says directly to her. She will not listen to Harry. She was told that when she awakens that she will go with Monica to get dressed for her mother's wedding. She was going to be the maid of honor. She will love the dress and shoes that she will be wearing. Kathleen nodded her head.

Chris went to Beth. He talked her into the trance. He told her that she had to do whatever he told her. He told her that she was a bride and she was marrying him. He instructed her when she awakens that she goes into the bedroom with Monica to get dressed. She will like the her dress and shoes. The final instruction was that Harry was giving her away at the wedding.

The girls awakened and walked upstairs followed by Monica and the large man carrying boxes. Chris told him to go to his bedroom and dress for the wedding.

After thirty minutes Harry and Chris waited with the large man, whose name is Rick. Rick was drinking another beer. Chris spoke to Harry, " You see. Beth will be marrying me for the weekend. Rick and Kathleen are going to be witnesses and you are going to watch what happens tonight and then you will can go home or stay and watch Then you will return on Sunday afternoon.

" Yes.", Harry was looking at his shoes.

The sound of clicking heels on the hardwood floors brought the men's attention to the living room. They walked into the room. Chris spoke. " Let's see them."

" Can't wait to see them in their outfits." Rick smiled.

" Me too." Chris smiled.

They watched as Monica walking down the stairs wearing a red dress to her knees and a pair of five inch red high heel pumps. Chris turned to Harry, " She is for the driver."

Harry felt bad that this was going to happen. He watched as the door open and heard the click of heels as Kathleen walked down the stairs. Harry was shocked to see his sister wearing a red bra to hold her large breasts, a red g-string, red thigh high stockings, and a pair of four inch black paten high heel shoes. Harry couldn't believe that his sister was looking like a slut.

" How am I looking, brother?" She asked sweetly.

" Beautiful."

Harry pulled his eyes away from his sister to his mother trying to walk down the stairs. He lost his color as he looked at her wedding dress or the lack of dress. She was wearing a long white veil that went down to her waist. The dress was a white teddy, which her breasts were exposed and pulled through where the cups should be. Harry had seen teddies like this before but not on his mother. Her legs had a pair of white thigh high stockings, a blue garter on her right thigh. Her feet were covered with a pair of white pumps with a thin five inch heel. Harry never seen her wearing that height heel before.

She turned to her son, " Honey, do you like my wedding dress?"

" Yes. I love it.", Harry couldn't lie. He looked at her ring finger. Her wedding ring was missing. He looked at Monica and it was hanging from her neck on a gold chain.

Chris informed the people, " Lets get going to the inn."

" Inn?", Harry asked as they walked to the front door.

" I rented the Cape Sound Inn for the weekend.", Chris informed Harry.

" Just a room, right?"

" Nope. I rented the whole inn for this. The employees and all rooms.", Chris was smiling at him.

Chris entered the car followed by Rick. Monica sat up front with the driver. Harry held the door open as Kathleen stepped inside. Beth stepped inside after Kathleen and sat next to Chris. Harry was next Kathleen. Harry was looking at his mother and noticed a zipper at her crotch. He couldn't believe he was looking at his mother's crotch area.

Rick's hand was playing with Kathleen's underpants as he rubbed at her slit.

.... There is more of this story ...

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