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.

The car went to the highway. Rick handed Kathleen a drink. He told her to drink. A drink was given to Harry and Chris. Chris said he didn't want to ruin Beth's dress. Harry drank his beer. He didn't want to do this. He looked out and saw the inn on the hill on the other side of the Cape Sound Canal.

Harry looked at his sister's outfit. He couldn't believe that Kathleen thought that was a dress. Both his mother and sister are wearing lingerie for a make believe wedding. He was worried about them. His feelings got worse when he heard he rented a whole hotel for this.

The car turned into the driveway of the small inn. The inn has twenty rooms, an indoor swimming pool and a large banquet hall. It was settled in a large forest on the other side of the canal.

Harry got out first and waited until everyone got out. Chris headed off to the manager's office. Beth was checking Kathleen's blonde hair.

Harry remembered Rick tell him that he was going to walk down the aisles of the large backyard courtyard. He would hand off his mother and watch the wedding. Then the lucky couple will match off to the banquet hall. After that he would have to do what is needed.

Beth spoke to Harry, " I am so happy that you and your sister are here for my wedding today to Chris."

" I know, Mom.", Harry answered. " We wouldn't miss it for the world."

Beth asked for a hug. Harry couldn't believe that he was going to hug her. He wrapped his arms around his mother and felt her nipples through the veil rub against his jacket. Harry closed his eyes and thought to himself that he wanted those nipples brushing his bare chest. He couldn't believe he thought that. He looked at his sister, " You ready as a bridesmaid?"

Kathleen nodded her head. She joined Harry and Beth into a hug. Harry groan silently at the feel of her bra against him. He shouldn't be thinking this about his mother and sister. He opened his eyes and saw Chris watching them. Harry broke the embrace.

Chris told them. " We are ready to begin. Will you get in line to march down the middle to the front. I will meet you there."

The three members of the family walked toward the back of the inn. They waited inside a closed in area. They had to wait until the music began. Harry waited impatiently for Chris. He looked at his mother. She was cool about it. His sister stood and showed a little bit cold. He couldn't believe that Kathleen thought she was wearing a dress.

Monica opened the door, " The music is starting."

Harry heard the wedding march. Kathleen started to walk down the middle aisle toward the front. Harry noticed she had a slight wiggle to her ass. Beth turned to Harry, " Ready?"

" Yes.", Harry answered as he held her gloved hand and started to walk down. They walked slowly until they came to stand in front of an elderly gentleman in front. Chris and Rick stood to the right. Kathleen was on the left. Harry released her hand and raised the veil to kiss her cheek. He stared at her naked breasts. He loved the sight of them.

He looked at Chris, " Don't hurt them."

Chris raised his hand, " I swear I will not hurt them."

Harry watched and listened. He answered the question who gives away the bride. He watched and almost cried. He watched as Chris slipped a wedding ring on her finger after the I do's. The diamond was huge it was close to two carats. Chris pulled the veil to kiss her on the lips. Harry watched Chris's hands feel the breasts as he was French kissing his mother. His fingers pinching the nipples. Harry felt slightly aroused at the sight. He didn't like it.

Chris broke off the kiss. He walked over to Kathleen, " Why don't you give me a kiss since I am family now."

Kathleen started kissing Chris. His younger sister was kissing him deeply. His hands roamed over her bare ass... He felt it and said aloud, " That's one firm ass she has. It is going to be fun to loosen that up."

Harry couldn't watch this. He closed his eyes. Chris saw it and yelled at him, " You gambled and lost. Now you will watch everything that happens."

Harry was angry over the fact. He didn't want to watch it because he was afraid that he would enjoy the sight. He was half aroused. He had to admit that he wanted to see his sister naked and being fucked. He had the same but more powerful emotions about seeing his mother like that. He really did want to see his mother doing that. He wished he could do that.

The kissing between Chris and Kathleen stopped and Beth's hand was inside her husband's hand. Kathleen and Rick led the way to the banquet hall.

Harry heard some music being played inside the hall. He heard voices too. What was going on? Was there people inside the hall. He turned and asked Chris, " Are there people inside there?"

" Oh course. It is a wedding.", Chris laughed at him. " What did you think that I would keep it a secret fantasy of mine. I don't think so. Now go inside and find your seat."

Harry looked down at his feet again. He asked again, " Who is in there?"

" People from my neighborhood."

Harry gave up and walked inside the banquet hall. He found out that every male in the neighborhood came over to the inn. The rooms were rented to them. He found his table in the front where Monica and the driver were sitting and waiting for the reception to begin.

Harry took his seat. He looked around. There are about fifty men and about twenty women. The color of their skins are more than half are black. Harry hated the knowledge of the people from his neighborhood. Harry had a really bad feeling about this. He didn't like it.

There was a disc jockey working at the other end. He started the entrance music and starting announcing the wedding party. Harry watched as the double doors opened. The Disc Jockey announced to the crowd, " Now stand and clap for the wedding party. First is the Maid of honor Kathleen being escorted by Rick."

Harry watched as Kathleen and Rick entered holding hands. The cheering for Kathleen wearing only the bra and panty was loud. The disc jockey spoke again, " And now, I am happy to announce the bride and groom. Beth and Chris."

Harry look at his mother and Chris as they entered. The cheers were louder for his mother. Harry could hear a couple of the guys talk about her breasts. Beth and Chris joined Kathleen and Rick at the front of the room. The disc jockey started to play a slow dance.

The two couples started to dance on the dance floor. Chris was whispering into Beth's ear. Harry figured he was programming her for the rest of the reception. Rick was whispering into Kathleen's also. Harry couldn't believe he was watching his two lingerie clad mother and sister dancing with two complete strangers.

The dancing continued at the slow pace as their hands roamed over the women. The look on their faces showed that they are enjoying it.

The music ended and so did the dancing. The two couples walked to the head table. The disc jockey walked over to Rick. " Now the best man's toast."

" I just wanted to thank Chris for allowing me to be here to help him. I know and wish you the best time this weekend.", Rick was smiling and then high five Chris. Harry looked at Kathleen and Beth. They sat and watched Chris and Rick.

The meal was being delivered to the fifty people. The meal was prime rib, baked potato, and mixed vegetables. Harry knew Kathleen hated prime rib. He watched as she ate the red meat. Harry was amazed that she was eating the meal. Harry didn't want to. He wasn't hungry by watching what was happening to his family.

The disc jockey announced, " Time to cut the cake."

Chris and Beth stood and walked to the small cake. They each cut into and fed each other. Beth's mouth was smeared in white frosting. Chris had small amounts on him. " That isn't the only white stuff on your face tonight."

The disc jockey announced, " Time for the throwing of the bouquet and garter."

Harry watched as single girls walked up front. Kathleen was in the front. Beth turned her back and flowers squarely into Kathleen. Beth went to the chair in the middle of the room. Chris knelt in front of her. Beth didn't cross her legs. Chris pulled the zipper down on her crotch. Chris went high on her thigh and planted a kiss on her crotch and stuck his tongue into her crotch as he slid the garter off her long leg.

Beth started to squirm in the chair as Chris's tongue is licking at her pussy. She is closing in on an orgasm. The garter has been long removed.

The men and Rick were ready to catch the garter and have the chance to slide the garter on Kathleen's leg. Chris threw it in the air and was caught by Rick.

Kathleen was brought to the chair. She didn't cross her legs. Chris moved the zipper down on her underpants. Rick knelt in front of her and slid the garter up her leg.

As the garter was sliding up the leg, Rick's tongue was tasting the virgin Kathleen. His tongue darting in and out of her pussy. Kathleen gave off a mourn as Rick continued to taste and eat Kathleen. Kathleen gave of a loud cry. The disc jockey announced, " I believe he has made her come."

Harry was in awe. The reception continued for another hour. Chris and Beth walked up to him. Chris spoke to him, " Are you ready to watch me and Rick with them."

" If I have to.", Harry replied.

Chris smiled, " You do."

The wedding party plus Harry walked away from the still partying fifty people. They waked up a flight of stairs to the second floor. They walked down to the corner suite. Rick opened the door. Chris carried Beth over the threshold. Rick and Kathleen walked behind them. Harry was last and he closed the door behind him.

Chris told him to bring two chairs into the bedroom. Harry followed his orders and carried two chairs from the living room to the bedroom. He emerged from the bedroom to see Chris sucking on the right breast of his mother. Kathleen was watching from standing next to her. Chris pulled off of the breast. Harry heard her mother gave off a sigh.

" Lets go to the bedroom.", Chris spoke. " All of us."

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