The Woman You Love the Most

"Am I really going to do this?! Am I going to touch my mother's asshole?" He just couldn't believe any of this.

"Do it, honey." Angela rushed him.

Jake slowly brought his finger closer to Lana's anus and touched it, spreading the lube over the beautiful wrinkled skin of her anus.

Lana trembled a little and let out a small moan of pleasure and lust. She started moving her ass a little, helping his finger spread the lube.

It was all too much, Jake knew as soon as his finger touched his mother's secret place that it was all over. He knew he was going to fail the test. He watched his mother's ass slowly swaying side to side as his finger was sliding over her asshole and he felt the explosion in his pants building up.

There was nothing he could do to stop it anymore. Angela noticed and watched her grandson as he made a grimace and let out a few quiet groans as he came into his swim trunks. He was still holding his finger on Lana's anus and then slowly moved it away.

He was looking at the floor and felt shame. He didn't know what to say or what they expected of him now. Angela walked over to him and ran her fingers through his hair like before. It felt comforting.

"You failed your test, honey. But don't worry, most do. You basically had no chance to begin with. Your mother is an exceptionally beautiful lady." Angela spoke softly as she caressed her grandson's head.

Jake felt his dick rising again. His mother was still in the same position right in front of him and his grandma's swimsuit hadn't dried fully yet so he could still easily see her nipples through the fabric.

Even though his dick was again almost as hard as it was a minute ago, he had a moment of post nut clarity and decided enough was enough. He wanted answers!

"What test?! What is going on? Why are you all acting like this is normal?!" He raised his voice looking at his grandma, expecting her to answer as it seemed his mother and grandfather followed everything she said.

"First we need to take care of you now that you failed the test." Angela said.

"Go inside and clean yourself up, you made a mess in your trunks. Make it quick, and then come back here."

******Jake's punisment******

He couldn't fight it. His grandmother's tone was not harsh, but it was obvious she was not taking no for an answer on anything. He sheepishly obeyed, went to the washroom and cleaned his dick. When he returned his mother was still in the same position, patiently waiting with her naked ass and pussy in the air.

Jake saw that his grandmother was holding something shiny in her hands, but it wasn't the butt plug. It was a bit larger. She pulled the chair in front of Lana and sat on it, so that Lana could see what she was holding in her hands.

"Come here, honey." Angela said to Jake. "Did you clean your penis?"

"I... yes, I did." He answered.

He walked over to her and stopped just out of reach.

"Closer." Angela said. "And pull down your swim trunks."

"What?!" Jake asked loudly.

"Honey, it will all be clear soon, don't worry. Now, come closer to your grandma and pull down your trunks like I told you." Angela said firmly.

Jake obeyed. Just a few minutes ago he was touching his mother's asshole, so him getting naked was far from the most insane thing that happened today. He stepped closer to Angela and dropped his pants.

"Mmm, what a nice friend you have here." His grandmother purred and gently touched the tip. He had an average length penis, but his grandmother seemed to like it a lot. She was looking at it carefully, judging the shape and thoroughly observing every detail.

In 5 seconds he was fully erect. Lana also lifted her head and looked at her son's dick.

"Don't you think your son has a beautiful penis, Lana?" Angela asked.

"Yes... it's perfect." Lana whispered.

Jake thought he might cum again if his grandmother touched him again. He had no idea what she was going to do.

"Now, let's get to the point, honey." Angela said. "You failed your test and you showed us that you can't be trusted with controlling yourself yet. So you need some self restraint training."

Jake took a better look at what Angela was holding and it looked like something he saw in fetish porn. It was a cock shaped metal cage.

"This is a chastity cock cage." Angela said, showing it to him. "We have to put this on your little friend here so that it helps your self control."

Jake just stared at the shiny metal thing in his grandma's hands.

"I think I got just the right size. It's quite big so it will start tightening around your penis when you start getting fully erect. That way it will stop you from getting too horny and cum in your pants like you did a few minutes ago." Angela said and opened the clasps on the cock shaped metal thing.

Jake watched as his grandmother put the weird contraption over his cock. There was a part that went around his balls to hold it in place and it took all of his concentration not to cum while she fiddled with it and touched his balls in the process.

She clicked the clasp and Jake felt his dick hurting as the cage was tight around his dick.

"Does it hurt, honey?" Angela asked.

"Yes, a little." Jake said as he looked down at his caged dick, shocked that this just happened.

"Good. It should hurt when you're erect like this. That way you will learn to control your penis. A man has to be in control of his body." Angela said and gave him a little tap on the cock cage that was firmly squeezing his dick.

"One more thing." She said as she took a tiny key from the table and placed it inside a small keyhole on the clasp. She turned the key and Jake's cock cage was now perfectly in place. "There we go." His grandmother said. It seemed that she was now the master of his dick's destiny.

Lana was just a meter away from it and had a good view of her son's dick struggling inside it's prison.

"Do you know why we had to do this, Jake?" Angela asked as she watched his cock cage.

"No..." He answered.

"Look at your mother here." Angela said and Jake made eye contact with Lana who was still on all fours on the deck chair.

"Do you think it's fair that she's still waiting for her gift? Do you think it's fair that you climaxed before she got what she asked you for?" Angela asked.

"No..." Jake answered again.

"Is that the way to treat the woman you love the most in the world?" Angela insisted.

"No..." Jake said.

"Now, do you understand why we had to make sure your cock is restrained so that you learn how to treat your mother like a princess?" Angela asked.

"I understand." Jake said.

"Good." Angela said. "Now that your cock is dealt with, you can start concentrating more on what you need to do."

Angela got up from the chair and walked to the chair with towels on them. She placed a couple of towels next to the pool.

"Lana, honey, come here." She said.

Lana finally got up from the deck chair where she was in a doggy style position for the past 15 minutes at least. She made no attempt to fix her bikini that was still pulled to the side. Her boobs were hanging out and her ass was bare. Jake watched his insanely hot mother as she walked over to where his grandmother was standing next to the spread towels.

"Come Lana, stick that pretty butt back up in the air. Jake needs to finish what he started." Angela said. Jake had a pretty good idea what she meant and he saw the butt plug and the lube bottle on the table.

"Jake, you know what needs to be done. Your mother is waiting. Oh, and take that other bag too." Angela said and then got on her hands and knees on the other towel right next to Lana.

They were now both lined up with their asses turned to Jake.

Jake brought everything from the table and walked over to his mom and grandma who were waiting for him.

"Why is grandma positioned like that too now?" He thought and then looked at what was in the other bag.

He pulled out a big black butt plug. Compared to the small metal one that was meant for Lana, this one was at least double its size in width.

Angela turned her head around and saw Jake watching the big butt plug in his hands.

"That one is for me, honey." Angela said. "My ass is well trained, so mine is a bit larger." She laughed a little as she said that and wiggled her butt at Jake.

"Grandma can take something like this in her ass?!" He couldn't believe it. "What kind of sex freaks are my grandparents?!"

"First, make your mother happy already and give her her present." Angela said.

Jake didn't want his grandmother constantly telling him what to do so he decided to act by himself. Listening to his grandmother telling him what to do to his mother made him even hornier than he already was and it really did hurt when his dick would get fully hard, so he wanted to prevent that.

He squirted some lube on Lana's ass crack and slowly spread it over her anus. She moaned softly as his finger caressed the opening of her asshole.

"Give it to me, honey." Lana moaned.

"This is absolutely insane." Jake thought as he took the small butt plug and placed it at the entrance of his mom's anus. He made several small pushes and then Lana slowly leaned into it and it popped right in, a lot easier than Jake expected. Only the small base of the plug was now visible.

"Thank you, honey. Thank you!" Lana kept moaning softly and it seemed like she was enjoying every second of it.

"Does it really feel that good?" Jake thought as he watched his mother's ass slowly moving side to side.

"Good job, Jake!" Angela said and lifted herself up a little to give Lana's ass a firm squeeze. "Look at how happy you made her. Don't you like seeing your mom happy and enjoying herself like this?

"I do." He muttered.

"Now, would you make your grandma happy as well? Please honey, I need it too, just like your mommy." Angela looked him in the eyes as she said this in the sluttiest tone possible.

Jake couldn't believe his grandmother could be this sexy.

He pulled Angela's swimsuit to the side and was now staring at her mature pussy and anus. Despite being 55 Angela's private parts were beautiful and completely hairless. She obviously took great care of every part of her body.

Like he did to his mother, Jake put lube on his grandma's ass and slowly applied it over her asshole. His dick was raging hard in its cock cage and it hurt more and more, but there was nothing he could do to stop his erection. He was doing the unthinkable to his mom and grandmother. How could he not be turned on?

"Good, you're very gentle, honey." Angela said. "Now take this big toy and stuff it in my naughty ass."

He took the butt plug and started rubbing his grandmother's asshole with it. It was a bit pointed at the top so it could slide in easily. He pushed it in a little and listened to Angela moan. "That's it, honey. Give it to me. Fill up my nasty hole."

He started pushing more as Angela pushed her ass back at him, but it was so big that it took some effort for it to slide in. Jake watched in complete amazement how his grandmother's asshole was spreading and taking the big toy inside. She let out a loud gasp as the butt plug finally went completely inside. "Thank you, honey. Oh, thank you for filling up my ass!" Angela moaned.

*****************

Angela and Lana remained on all fours for a little while, letting Jake get a good look at what he just did. It really was a sight to behold. Angela then got up and Lana followed her inside the house.

Jake was left there by the pool, naked, with only the cock cage torturing his dick. He waited a little for his erection to calm down and then walked over to where he dropped his swim trunks and put them back on. His grandfather was sitting there on one of the chairs, calmly sipping on his drink.

"So, how about that?" Hank said, like he was commenting on something barely a little unusual.

Jake looked at his grandfather, hoping he would say something and make a little more sense of all of what happened today.

"Those ladies are quite something, aren't they?" He asked.

"Yeah..." Jake said and sat down on the chair. He felt his cock cage rattle a little under his swim trunks.

"Can you tell me what the hell is going on?" Jake asked his grandfather.

Hank let out a hearty laugh. "I know you're confused. And your grandmother likes the tease so she's not telling you everything right away. How does that chastity cage feel?"

"It's fine as long as I don't get hard." Jake said. He still hoped his grandfather would start explaining the situation so he didn't want to change the subject, even though it felt awkward talking to his grandpa like this. He never talked about anything sexual with his grandparents before. This was all completely new and weird. But somehow both of his grandparents acted completely natural about it.

"They obviously planned all of this in advance. Mom never stayed here before and this year she acted like it was expected of her to stay. What was grandma talking about with the 18 year long wait. And why the hell am I being tested like this. I'm still a virgin, how could I not cum? It was a miracle I lasted as long as I did." Jake couldn't make sense of it.

"Like your grandma said, you are now part of the family tradition. As you turn 18 and become a real man you have to take responsibility for the women of the family. More specifically, you have to take responsibility for their pleasures and make sure they are satisfied. That's why your dick is in the cage now. A man has to learn to have control over his cock otherwise he can't fulfill a woman's needs. And it all starts with your mother. The woman who gave birth to you and raised you to become the man you are today. You have to show her the ultimate love and respect." Hank said.

"None of this makes sense. Who came up with this? This is not normal!" Jake said. He was glad his grandfather was talking about it. He feared that he would avoid the subject and he would have to wait for his grandmother to come back and say something.

"It may not be normal for other families, but ours is special." Hank continued.

"So, what are the rules? What is that about waiting for 18 years? Waiting for what?" Jake asked.

"I'm sorry, you'll have to wait a little bit more to get the full story. But I promise you it's all worth it. Just trust your grandma and do what she tells you. You will have lots of fun, I promise, and you will make your mom a very happy woman." Hank said.

Jake stared at the water in the pool. Images of his mother and grandma in their indecent swimsuits flashing before his eyes.

"Now, go get changed, your grandmother will call you when she and your mother get ready. They plan to go shopping and you will go with them." Hank said.

******Shopping trip******

Jake went to his room and decided to take a shower. He realized that washing his dick is going to be a bit tricky through the cage.

"I guess all of this will be over soon and grandma will unlock this thing. This is ridiculous." He thought as he sprayed the shower through the small cage.

He got dressed and stayed in his room, watching random videos on his phone, trying to get his mind off of the things that happened today.

A while later he heard his grandmother calling from downstairs.

"Jake, come down here please."

He went downstairs and saw his mother standing in the living room. She was wearing a light, short summer dress and flat shoes and had her hair raised into a bun. She looked beautiful, her big breasts and hips nicely highlighted by the slim waist.

Angela appeared from the kitchen. She was wearing a white sleeveless shirt with a very deep cleavage and a long light skirt that swayed when she walked.

"You're here, good." Angela said. "We're going shopping and we need a driver, so you're coming with us."

Jake thought it's time to act normal for a change and it would just be a simple shopping trip. He would soon learn that that was not the case.

Jake's grandparents had a big yard with a very big driveway. Lana and Angela walked to the car and waited for Jake. Jake got to the car and was about to get in when Angela said "Before we go, you need to do an inspection, honey."

Jake waited for her to explain, he had no idea what she was talking about.

Angela and Lana walked to the hood of the car and they both leaned on it. "Come here, honey, and check that everything is still in place." She said and stuck her ass out.

Jake got behind them and watched their nicely shaped asses. "She wants me to take a look at the plugs in their asses, doesn't she?! Is grandma trying to drive me insane?!"

His cock was hard already and it started to hurt in its cage. "Better get this over with quickly." He said to himself and lifted his mother's dress over her ass.

She was wearing a lacy white thong. Jake never thought his mother even had such underwear. Despite her great body she was always acting so decently that it was hard to think she would wear such underwear.

"So? Is everything in order?" Angela asked.

Jake spread his mother's ass cheeks a little and saw the butt plug underneath the thong. He moved the thong to the side a little bit and touched the base of the butt plug with his index finger and then gave it a little push and wiggle. Lana was a little shocked. She expected that her son would need some encouragement from Angela before he does anything. She felt her pussy getting wet. "My son is playing with my asshole, why does it feel so good..."

Jake's dick endured the torture as he adjusted his mother's thong back between her ass cheeks and he lowered her dress back down over her ass. She remained in that same position as Jake moved over behind Angela. It was her turn now for an inspection.

Her light summer skirt was long, reaching her ankles so he crouched down and slowly lifted it up to reveal his grandmother's firm, suntanned legs. Finally he revealed her ass and discovered that she didn't wear any panties. "Grandma is full of surprises." He thought.

He leaned to get a look as he spread her ass cheeks and expected to see the base of the large butt plug sticking out. But all that he saw was his grandmother's anus.

"I'm sorry, honey, I had to take it out while I was getting ready. It's so big, it was too much to handle." Angela said with her sexy voice. "Do you think you could put it back for me now? My ass had enough rest."

"If that's what you want." He remembered what his grandfather told him about pleasuring the women of the family and making sure they got what they needed.

"It's right here in the little bag." Angela said, and Jake took out the big black butt plug and a bottle of lube. He applied lube over it and slowly spread some over his grandmother's asshole.

"Put your finger in just a little bit, please honey." Angela pleaded.

"Oh God! I'm going to cum if I do that, it's too much!" He thought as he watched his index finger sliding over the entrance of his grandmother's asshole.

Slowly he pushed his finger inside. It went in with almost no resistance. His grandmother's ass was obviously used to having things go inside.

"Yes. Yes. Oh yes, honey!" Angela moaned softly.

"I'm holding a finger in my grandmother's ass with my mom right next to us. I think I'll have a stroke."

He pulled his finger out and placed the tip of the butt plug inside and started slowly pushing it in. It went in smoothly and popped in. Angela's asshole was completely filled with the large toy and she let out a couple of loud groans. "That's it Jake, you're learning quickly." She said as she lowered her skirt.

She and Lana got in the backseat of the car. It was his grandfather's new Mercedes and Jake was very nervous driving it for the first time. And as if that wasn't stressful enough he had his mother and grandmother distracting him by acting like this.