"Maddie, yesterday you were tanning out by the pool, please continue to do so for now. Lisa here needs to be punished for not turning up the sybian yesterday. Just don't spy on us this time." With a look of relief, Maddie left for the pool to tan and rest her pussy more.
"Alright Lisa, follow me to my bedroom, it's time for your punishment." Lisa had a worried look on her face but followed anyway. Jason made her drop her g string and bend over the bed. He then placed a blindfold over her eyes. Lisa stood there bent over nervously. She could only hear Jason's footsteps, then she felt her ass cheeks be spread, exposing her tight asshole. A cold sensation spread on her asshole. Lisa shuttered, knowing that she was in for anal. Then instead of feeling a cock enter her, Lisa felt a hard silicon butt plug enter her ass. Lisa gasped and moaned as it was pushed into her depths, until nothing but the handle remained outside. Jason loved the view from above as Lisa's asshole had to stretch around the intruding plug. The plug was about 6 inches long and 1.5 inches wide and Jason was surprised how much resistance he encountered pushing it in. After it was into the maximum depth, Jason let her ass cheeks fall back into place, and the toy was completely hidden from view. Lisa never really enjoyed anal but pretended to for her films. She shifted uncomfortably, trying to get use to the feeling of having her ass filled.
"Alright, like I said, the punishments start small for the two of you. The only thing you have to do is leave this inside you for the rest of the day." Lisa agreed, just wanting the day to be over. However, Jason wasn't done with her yet. She felt her bikini top be removed and her large, saggy tits were out in the open. Jason turned her around and pushed her onto her back on the bed. He then pushed his 6.5-inch-long cock into her pussy. Lisa could take big cock but was much tighter currently because of the toy in her ass. She could feel his cock touching the toy through the thin back wall of her pussy. Lisa soon got used to the feeling if the double penetration and began to breath heavily as she neared orgasm. Lisa finally came and her pussy muscles tightened around Jason's cock, lubricating it with her cum. Jason pulled out with a bit of her cum dripping off of his cock and then pushed it into Lisa's mouth.
Lisa had tons of experience sucking cock from all of the work she had done over the years and quickly sucked Jason dry as his hot cum ended up on her tongue and Lisa gulped it down. Jason then began to play with her pussy, licking it and gently forcing fingers inside her. He started with one and as Lisa got more turned on, he slipped a second one in and there was a little extra room and Lisa was moaning with pleasure, so he pushed a third in. It was a snug fit as the walls of her vagina tightly hugged his fingers, her pussy lips gripping them as they slid in and out of her pussy. Lisa soon came a second time, and her white thick cum made a squishing noise as Jason pumped his fingers in and out of her dripping hole. He slowed gradually, and the slurping noises subsided and were replaced by the pleasure moans and heavy breathing of Lisa, which also began to stop after the fingering did. The blindfold was removed and Jason was staring into her eyes and said,
"Lisa remember, do what I say when I say or the punishments get worse. Understand?"
Lisa said yes and was told to dress. Once she was back in the skimpy outfit, Jason kissed her on the lips and reminded her that the plug does not come out until later that night. He then told Lisa to go rest with Maddie, as they would both need it for later. Lisa went downstairs and out to the pool area where she found a pool chair next to Maddie and laid down, trying to forget about the 6 inches of hard silicone up her ass. Jason came out not long after and the three of them relaxed near the pool, only getting up for drinks or food.
For Maddie, it was just a relaxing day wearing a very tiny bikini top and a g string which was swallowed up by her toned young ass. She knew Jason was looking at her toned body. Part of her liked that she was getting the attention, but another part of her wished the older man would leave her alone and focus on her mom. Lisa was having a much different time. Lisa's ass swallowed her g string as well, but the 6-inch plug felt like it was much larger in her tight ass.
The three of them made small talk, and the topic of sex was largely avoided. At 5:30 pm, the plug had now been in Lisa for almost 7 hours. Jason announced that they would go inside and eat, then the nightly fun would begin.
