Ginny again shook her head yes. Dean reached over and took off the tape from around the squash and let it slide easily from her ass. He then removed the tape from around her thigh holding the vibrator allowing it to fall from her pussy. Ginny did not say a word when they were both out of her. Dean walked over and picked up the whiffle ball bat and began. Tap tap,... tap tap,... tap, tap,... tap, tap,...tap, tap, tap, tap, tap, tap, tap, tap, tap. As soon as he finished he walked back to Cindy and played the same cadence again on her ass.
Dean again returned to Ginny and played it all over again. Dean decided he should give them a little rest and explore the barn to see if he could find something else to use on them. During his explorations Dean came across a box of brand new latex gloves. He thought to himself that this could be fun but he kept moving. In a cupboard in the tack room Dean found something that really caught his eye. He found several feet of flexible tubing about an inch in diameter. Lying under the cabinet was a 5 gallon bucket that someone had written water only on. He took those items with him and then walked out across the barn again exploring when he heard one of them say something to the other. He walked over and picked up the bat and played the cadence on Ginny's ass and to make sure he got the right one he played it on Cindy's ass as well. This time the strokes of the bat were harder and each tap left a red mark across both there asses. "When I want you to speak I will tell you or I will continue." Dean started going through closets along the barn wall and he asked Ginny what was in the cabinets. She told him that they contained items that they used for cooking turkey's and other things for large groups. He didn't expect to find anything in there but he came across a couple of turkey basters which he eagerly grabbed. Now if he could only find connectors. He asked Ginny if they had any plumbing supplies and she looked at him and told him in the garage.
Dean headed quickly to the garage and found what he needed and then returned to the ladies.
"Ok ladies, here is how this is going to work for starters. We are going to play a game and each time you win you get to pick what I do to the loser. Hope you enjoy this because I am going to." Dean walked over and put a pail in between the ladies and then handed them each a washer. "You are both going to try and get the washer in the pail. The one that is the farthest from the pail is the loser."
The ladies flipped their coins and Ginny was thrilled when hers hit the pail and landed a few inches from it. Cindy flipped hers and from the angle she was at it was difficult but she landed just outside her mothers. Cindy sighed as Dean walked up behind her and picked up the whiffle bat and the 2 inch butt plug. He looked at Ginny and said, "Either 25 whacks with the bat or the plug goes in 25 times."
Ginny pointed to the plug and Cindy yelled, "Mom no how could you." Dean greased up the plug with KY and inserted the plug slowly into Cindy. He again slowly removed it. He repeated this until she had loosened up her ass a bit and then he just finished the last 15 quickly. Cindy was moaning as Dean finished with the last plunge up her ass.
"That's the end of round one ladies lets go onto round two." Dean's cock was starting to get hard after playing with Cindy's ass and since he had not had her ass yet he looked forward to it.
The ladies again threw their washers and again Cindy lost. Dean walked behind her and held up the bat and he dropped his pants and held his cock. "25 of each what is your choice?" Ginny smiled and pointed at his cock. Cindy could not see what had been chosen but she felt Dean move up behind her and he took his hard cock and rammed it into her ass in one stroke. He then grabbed her hips and told her to count to 25. When she got to 25 Dean pulled out and looked at her as her gaping asshole twitched. He didn't know if Cindy was enjoying it but he was.
"It's time for round three." Dean gave them their washers and Ginny threw hers and it just missed the bucket but landed very closely. Cindy threw hers and this time she got lucky it landed in the bucket. All you could hear was "Oh yeah mom is going to get her ass reamed."
Dean didn't even bother with the bat he picked up the latex glove and the 2 inch butt plug and showed them to Cindy. Cindy started laughing and pointed to the glove. Her mother had no idea what was going to happen. Dean walked in front of Ginny and put the glove on his right hand and lubed up the glove. "You can't be serious you can't shove your hand up my ass. Oh my god it won't fit and you know it. Cindy how could you do that to me?"
Dean walked behind Ginny and slowly inserted one finger and he pumped it in and out a few times and then added another finger. After a few minutes he added a third finger and then a forth. Dean tucked his thumb inside his fingers in order to try and make his hand smaller and proceeded to slowly insert his hand into Ginny. He started to push and told her to push as well and slowly his hand started to disappear into Ginny's Ass. When he got the widest part Ginny's ass just sucked his hand right in. Dean then proceeded to give her a moment to get used to it and then he slowly withdrew it and then pushed it back in again. Dean wondered how many times he was going to do this. He decided ten should be enough and he proceeded to push his hand in and out until he pushed in for the last time. Once his hand was inside Ginny's ass he made a fist with his hand then proceeded to pull it out of Ginny. The pressure became too tight and he released his hand and let it slide out of Ginny.
"You better hope to hell that you do not lose another game tonight sweet daughter because you will pay."
Dean handed them each a washer and Ginny made hers right into the bucket and she began to laugh. Cindy missed the bucket completely and Dean moved in behind her again. He held up the bat and the butt plug and Ginny shook her head no. He held up the Butt plug and the latex glove and Ginny shook her head no. She pointed at his cock and she shook her head yes. He then held up the butt plug and the latex glove and the pointed to the glove. Dean knew this might be difficult for Cindy but her mother wanted her revenge.
Dean walked up behind Cindy and took the lid off the tube of KY and aimed it up inside Cindy's ass so that she had as much lube in her as possible. He then lubed up his cock and got behind her and shoved his cock in again all in one thrust. He grabbed her hips and fucked her hard until he came. Once he pulled out of her he took the 2 inch butt plug and put it up her ass. Cindy thought that this was the end of it she but she did not know that Dean was trying to stretch her a little at a time to get her ready for his hand.
Dean pushed and pulled the butt plug in and out of her ass until it was loose enough that she could not hold the plug in without it falling out. Cindy was exhausted but Dean knew he had to at least try to get his hand inside her. He lubed up his hand and started to push into her ever so slowly and all you could hear was, "oh my God mother how you could do this to me. I have never had anything that big in my ass before."
Dean continued to push and pull and he slowly got his hand into Cindy's ass. When it finally went in Cindy started to shake and quiver as she had a violent anal orgasm. Dean slowly pulled his hand out and he did not try to put it back in. When he had removed his glove he said I think it's time to play warm the asses for a bit. When I start with the paddle I am going to give you 5 stokes with the paddle. The one who concedes first is the loser. If there is a tie we will have a tie breaker.
Dean walked up behind Cindy and gave her 5 hard slaps in a row without a break. Ginny just laid her head down and waited until she heard slap, slap, slap, slap, slap. The slaps came so fast she almost heard them before she realized it was her ass they were hitting. Dean walked over to Cindy and started to repeat the process of slap, slap, slap, slap, slap. Cindy almost gave in with those slaps because Dean was hitting them harder with each round of slaps. He walked behind Ginny and again gave the same 5 slaps with equal force causing Ginny to gasp. Cindy was hoping her mother would give in but she did not she held her own and waited for Dean to walk up to Cindy again hoping she would quit.
SLLAAAP, SLLAAAP, SLLAAAP, SLLAAAP, SLLAAAP, you could hear from outside the barn if you were there. The force of those five slaps made Ginny cringe and she knew that she was next. Ginny knew if she did not take them she would be the loser. She took the slaps again and she hoped Cindy would say no more then she would only have to take one slap to be the winner. Dean walked over to Cindy and she told Dean she could not take anymore. Ginny was elated. "Give me one good slap and I will be the winner."
Dean told her if she took one he was going to ask Cindy if she also wanted one and then if she told him that she could not take any more then Ginny would be the winner. Ginny's ass was on fire and she didn't want any more strokes so she told Dean she was not going to take another stroke either. "Well it looks like we have a tie ladies and that means I get to use the tie breaker. All you have to do ladies is stay right where you are and I will get it set up. Dean grabbed the 5 gallon bucket that he had before only he had installed a plastic fitting in the bottom of the bucket. He pushed one end of the flexible hose onto it and then shoved a tee coupler into the end of the hose. He then added a short piece of hose to each end of the tee and then shoved a plastic turkey baster onto the ends of each short hose. He lubed them up and shoved the turkey basters into each of the ladies and told them that this is the finale for the evening.
Dean tied the bucket up to a rafter about three feet above both women and said, "I am going to start filling the bucket with water from the garden hose. The water will start flowing down the hoses and through the turkey basters into each one of your asses. The first one to lose their turkey baster is the loser. If you lose you will have to sleep with the 2 inch plug up your ass until the alarm clock goes off at 7 tomorrow morning."
Just as Dean was about to turn on the water his phone rang. "Yes mother, I am glad that he called, did he tell you what he needed to talk to me about? Yes, great mom thanks that is good news. Yes mom I took out a loan because I can do that you know." Dean made faces showing his displeasure with his mother. "Okay mom, I bought a house to live in while I am finishing college. I am going to rent out four of the rooms and have one to myself. No mom I have not found anyone to rent them yet I just found out I got the loan. No mom I don't know who to rent to yet and I will look into it as soon as possible quit worrying."