Once Dean was hard he walked up behind Ginny and again started playing with her pussy. This time he drew the moisture from her pussy up and over her anus until he had it good and wet. He then proceeded to shove his middle finger up her ass and watched to see her reaction. He did not see much reaction so he inserted another finger as well. He then began pumping then into her ass in slow even strokes for about 5 minutes. Dean then said, "Since I am going to punish you in much the same manner as you did Cindy I decided to work you up in steps until we reach the final toy that I have selected for your ass. I hope that you enjoy all of them."
Ginny looked back over her shoulder at Dean when he said all of them and said, "I only used one dildo to punish Cindy."
"I realize that you only used one to punish Cindy and I will use that one as well. I have one to use before that and two that are slightly larger than it as well so your ass will never again forget." Dean answered with an air of superiority.
Dean then walked over to a shelf and grabbed a tube of KY and began to rub it into Ginny's ass. After it was ready to go and Ginny was lying with her face turned Dean applied the KY to his hardened cock. Dean walked up to her and in one thrust ran his cock up Ginny's ass. He grabbed her hips and started thrusting fast and hard as he listened to Ginny's grunts and ooh's and aah's as he continued to punish her asshole. Dean pounded Ginny until he could take it no more and with his still hard cock in her ass he began to spank her again with his hand while he listened to her moans. "You really have a nice ass cousin you know that and I am going to enjoy fucking it off and on today."
Dean again continued you thrust into Ginny's ass until he finally came with a loud grunt and then a well-placed smack across Ginny's ass cheeks after he pulled out. "I am so glad you gave me that blowjob earlier this morning. I knew that I could last much longer that way." Dean said with a bit of a laugh in his voice.
Dean decided it was time to up the ante a bit so he picked up the child's plastic whiffle ball bat that he found in the closet. It was only about an inch in diameter but he was sure that it would leave some nice marks and the sting should be felt without a problem. Dean stood behind Ginny and then began to swing the bat and listened to the snap, snap, snap sound as it landed repeatedly on Ginny's ass. "What the hell is that thing?" Ginny cried out to Dean.
"Oh it's only a child's bat that I found in the closet last night after you went to bed. You told me I was to make it more severe than what Cindy received and that is exactly what I am doing." Dean replied.
Dean continued to give Ginny about 50 smacks across her ass with the bat and then he stopped to look at his handiwork. He could see lines across her ass where the bat had struck. Much like belt marks just not as wide. "I think it's time for a little change and since you were so fond of this dildo last night I am going to use it on you just so you know how Cindy felt. Remember it's only the second item and I have two others left that will definitely enlarge your asshole." Dean laughed.
Dean lubed the dildo and then slowly shoved it up into Ginny's ass. He then proceeded to give her stroke after stroke with the dildo into her upturned ass. Dean continued to thrust the dildo into her ass for about 20 minutes never stopping for a break and his arm was getting tired. He was sure however that his arm felt better than Ginny's ass. Dean finally pulled the dildo from her ass and then picked up the paddle that Ginny had used on Cindy the night before.
"I am not going to count the strokes that I am going to give you I am simply just going to paddle you until I get tired of each implement." Dean said and with that he began to paddle Ginny.
Ginny was able to hold on for a time but the repeated almost constant swats finally took their toll and she started to move her hips side to side trying to avoid them and her oohs and aahs became almost constant after each repeated blow to her already reddened ass. Dean took delight in making her acknowledge each and every blow. Dean also noticed that the wetness along her thighs was much heavier than it was when he started. He knew that what he was doing was turning Ginny on.
Dean also knew that this was supposed to be a punishment spanking and he wanted to make sure that she was satisfied in that account as well. Dean had finally tired of the paddle and decided that since his cock was as hard as steel again that he would again take Ginny's ass. He walked behind her and then with a quick thought he shoved his raging cock into her pussy on one full stroke. Ginny quickly turned around and looked at him glaring and said, "What the hell do you think you are doing I am not on birth control."
Dean just looked at her and continued to pump in and out over and over and then pulled his cock free from her pussy and shoved it into her ass. He continued to stroke into her ass, holding her hips until he came. Once Dean had finished he walked around to Ginny and said "Clean it."
Ginny just looked at him but did as he asked. She licked and sucked on Dean's cock until it was clean. Dean then pulled from her mouth and walked back behind her and told her it was time to up the ante so to speak. He walked to the bench and opened a bag that had a summer squash in it. It was long and yellow with a neck on it that had to be about three inches in diameter. He had shaped the end of it so that it was smooth.
Dean walked the squash up in front of Ginny and said this dear cousin is what is going up your ass next. I hope you enjoy it. Remember you told me to be more severe and that is what I am doing right now.
Dean walked up behind Ginny and picked up the KY tube and squirted a large amount into her awaiting asshole. He then covered the end of the squash with a good dose as well and then placed the end of the squash against her asshole. He started to slowly push and he told Ginny to push as well. It took some time but her tight anal ring finally allowed it to pass and Dean carefully pushed the squash up her rectum until it would go no farther.
Dean left the squash up her ass for a few minutes and then he proceeded to use long slow strokes taking the squash out and in, out and in. Ginny was almost beside herself. Her hips were gyrating and she came from the repeated thrusting in her ass. The fluid ran down her legs in a stream. Dean continued to ream out her ass with the vegetable for about 15 minutes and then pulled it out again with one strong pull leaving her anus gaping. Ginny let out a large breath of air and her chest and head went down as she waited for what Dean would do to her next.
Dean gave her a few minutes and then walked up to her and with his hands behind his back he told her that the last implement he would use on her ass today was one that he found in the house. He looked at her and said, "I thought it fit the moment and the words on it were inspiring." With that he pulled a paddle made of wood out in front of her and read the inscription, "Spare the Rod and use this Paddle."
"Quite fitting for the moment don't you think cousin?" Dean said with a smirk.
"Are you crazy that's an old fraternity paddle. It was made for each and every pledge in the fraternity. I had to work very hard to steal it away from them and it is not made to be used. It is a decoration for my room." Ginny said with a real sense of concern on her face.
"Well this little decoration will have a lot more meaning when we are through with it today. You should not have stolen it and today I will make sure that you know the error of your ways." Dean said as he walked behind her.
Dean lifted the heavy paddle and began to blister her ass with it. He gave her stroke after stroke after stroke with it. Her bottom had gone from light red to red to crimson and now was approaching purple. Ginny was howling with each and every stroke that Dean gave her. She was crying and sobbing and begging him to stop to no avail. Dean continued to spank her with it until he decided she had enough and his arm was tired.
Dean glanced down at his watch and noticed that it was after 5 p.m. and that he had been at this for over 6 hours already today. He knew that Ginny had to be exhausted and he was willing to give her the last item on his list for her punishment. Dean asked her if she was comfortable and she just shook her head yes.
Dean told her he was going to complete her little punishment with one last item and then he would let her rest. Dean walked over and got another Squash that was over three inches in diameter and he lubed it up and began to shove it up Ginny's ass. Ginny screamed at him when it finally gave way and went in passed her sphincter. Ginny had never been stretched so far in her life. She thought that she would never be able to walk again after Dean shoved it up her ass and then he began to pull it and shove it in again fucking her ass with the huge vegetable. Dean fucked her ass with it for over fifteen minutes and then he stopped with it completely up her ass. Dean again walked over to the table and took an electrical dildo that was about two inches around out of the bag. He placed the head of the dildo at Ginny's pussy and shoved it in as far as it would go.
Dean plugged in the vibrator and then took tape out and taped it firmly around her thigh so that it would not come out. He also made a loop of tape or two around the squash and around her thighs so that it would not slide out easily. Once he was finished he switched on the dildo and the humming began. Ginny immediately went crazy. Having a huge vegetable up her ass and the large dildo in her pussy was driving her crazy. Dean walked over to her and said, "You just lay here and rest and whatever you do make sure that the squash stays in your ass until morning. If I come back in the morning and find it is not there I will have to repeat this little sequence all over again. It looks like this indeed might be the best S and S session you have ever had."
