The Woman You Love the Most

First time publishing a story. All characters are 18 or older and entirely fictional.

Short description: It's summer and Jake turned 18 recently . He and his mother are visiting his grandparents. He has no idea that his grandmother has a lot of plans for the two of them...

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

Jake turned 18 a few weeks ago and graduated from high school. The summer was ahead of him and like every year he was about to spend a few weeks with his grandparents on his father's side.

They lived in a smaller town about an hour drive from where Jake lived with his parents.

Jake's grandma, Angela, was only 55, but most people would probably say she was in her early forties. She still went to the gym regularly and it showed, her big breasts and ass still holding firm.

This year Jake's mother, Lana, was going to stay too. Jake wasn't sure why, none of his parents stayed there before with him. Lana was a school teacher and had a lot of free time during summer, so he figured she just wanted a change of scenery for a few weeks.

They arrived early on Saturday and Jake's dad, Mike, quickly left.

Lana and Jake got comfortable in their rooms and by noon they were all sitting and relaxing by the pool.

Jake's grandparents were pretty well off and had a very nice, big house with a huge backyard and a pool. He didn't mind spending time here one bit.

Angela brought drinks for everyone and they talked for a while about this and that.

"Anyone up for a swim?" Angela asked. "It's such a hot day, I sure could use a refreshing dip in the pool."

She got up and turned to Lana. "Come with me dear, I got some new swimsuits. Some of them might be a bit too small for me so if you like them you're welcome to have them."

They could easily try on the same clothes as Lana was of similar build as Angela, big breasts and wide hips, with a flat stomach. People would probably think they were mother and daughter.

Lana followed Angela into the house without a word. Jake thought his mother was acting a bit strange for the whole trip, like she was nervous or something.

Jake and his grandfather, Hank, remained sitting by the pool and had small talk while sipping on their drinks. It was a beautiful day and Jake planned on jumping into the pool soon too.

Angela and Lana change into swimsuits

After some while Jake heard the voices of his mom and grandma behind him coming back. He turned around and the sight he saw made his head spin. His grandma was wearing a white one piece swimsuit that was revealing most of her huge boobs and barely covered her nipples.

Even more shocking was what his mom was wearing. A tiny red bikini which you would never expect a classy lady like Lana to consider putting on. The upper part was just enough to cover her nipples. You could see the shape of her erect nipples through the thin fabric.

And the lower part was basically just a few pieces of string. Her ass was completely naked with the thin thong disappearing between her soft butt cheeks.

Jake was stunned and had no idea what to say. He was absolutely stunned. He never saw his mom wearing anything remotely this revealing.

"What do you think, Jake? How does your mom look?" His grandma asked with a grin on her face. Jake never before saw her smile devilishly like that.

"What is going on?!" Jake screamed inside his head. "Why is mom just standing there without a word, waiting for me to comment on her obscene look?!"

He just barely muttered "Okay", hoping they would reveal some sort of a weird joke between them and Lana would go get changed into something decent.

Hank spoke suddenly. "Jake, you're 18 now. A real man. We all waited impatiently for you to come of age so you could finally become a part of this beautiful tradition that our family has kept going for generations."

"What the hell is he talking about?!" Jake's mind was racing trying to figure out the logical explanation to this.

"W... what tradition?" Jake muttered.

"You will see. You will have a lot of fun. Don't worry, honey." Angela said and walked to him. She leaned over him and ran fingers through his hair. Her fingernails felt good and he felt his dick twitch in his pants. He had a full view at her huge cleavage and soft skin of her breasts.

And just a couple of feet away standing there was his mom, dressed like she was the biggest slut at a spring break college party.

Angela told Jake to put on his swim trunks and come back to the pool. He went to his room to change and when he came back all three of them, his mom and both of his grandparents were in the pool.

As he came closer he realized his grandmother had pulled the straps of her swimsuit to the side and her big natural double Ds were hanging out. He felt his cock getting hard again and quickly got into the pool to hide it.

"Jake saw my boobs before, haven't you honey?" Angela said, looking him straight into the eyes, expecting his reaction to a sudden question. The pool was quite big so they weren't close to each other.

***Last summer***

He wasn't sure what to say. Last summer while he was staying here he was extremely horny most of the time. He jerked off 2-3 a day. Since he didn't have a laptop or anything here he couldn't watch porn or read sexy stories like he usually did. So his main source of fapping material was taking glances at his grandma while she was by the pool in her revealing swimsuits.

But there was one night in particular that remained engraved in his horny memory. Jake's grandparents were watching TV late that evening and sipping on wine. Hank went to bed at some point but Angela stayed lying on the couch trying to finish watching the movie.

Some time after midnight Jake got up to go to the kitchen for a glass of water and saw his grandma lying on the couch, wearing only her nightie and panties. One of her tits was dangerously close to spilling out of her nightie and Jake noticed that. He figured that Angela had a little bit too much to drink and fell asleep on the couch, so in his horny state of mind he tiptoed closer to her and watched her softly breathing. Her breasts rising and with every breath the nightie was closer to revealing the nipple.

He couldn't control himself anymore and got even closer. As slowly as he could he pulled the thin fabric to the side and one of Angela's breasts was now fully exposed. He was trembling with excitement. He couldn't believe what he just did. His own grandma!

He managed to collect himself from staring into the beautiful nipple and that perfect full, round breast. He already had a whole story in his head in case she woke up. He would say that he wanted to cover her with a blanket. But deciding not to risk it any further he tiptoed back to his room and fapped furiously before quickly cumming, thinking about his sexy grandma.

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

"You thought I was asleep when you took a peek at my boobs last summer. Oh, that was so sexy, Jakey. I was so happy you liked your old grandma so much that you would sneak around the house. And you kept watching me when we were here by the pool. I felt your pervy little eyes on me all the time. It was hard waiting for a whole year until you could join us having fun." Angela said before Jake had time to come up with any kind of response.

"And your mom too." She continued. "Until her boy reaches 18, the mother can't join the tradition either. Same goes for the father. Until your sister reaches 18 your dad will unfortunately have to wait to join us.

"Come closer to grandma, honey, let me explain it better." She said.

Jake pushed through the shoulder high water to get closer to his grandma who had her heavy breasts on full display. Jake's eyes were pulled to her big areolas like magnets to metal.

"It's kind of complicated, but let me give you the basics." Angela started explaining.

"When a child is born it is the day that one of the parents starts their 18 years long wait. So in the case it's a boy, a mother is waiting for her son to turn 18. And this is where you and your mother are right now. Right, Lana?" Angela turned to Lana who spoke for the first time since she came out wearing that slutty bikini.

"That's right." Lana responded quietly, looking at the water, too shy to make eye contact with anyone while dressed like that.

"Waiting for what?" Jake thought, but expected his grandma to continue explaining so he kept quiet.

"Look at how shy your poor mommy is.This is just a result of her 18 years long wait with you. She acted like a good girl for 18 long years. Well done, Lana, you did very well. And you gave us such a fine young boy here." Angela said, looking at Lana and then continued.

"I guess the most important, and the most interesting part for you is what does that mean for you. Right Jake?" Angela turned back to him.

"Tell me, who is the woman you love most in the world?" Angela asked Jake.

"Umm... What do you mean?" Jake was a little surprised by the sudden question.

"Well, just tell us the truth. Is there a woman you love more than your mom?" Angela moved slowly through the water towards Lana as Jake watched.

Just as he was about to say something, Angela came face to face with Lana who was still avoiding eye contact, and pulled the strings of her tiny bikini to the side. Both of Lana's big, perfect breasts fell out. Her nipples were just under the water so they were still partly hidden, but Jake felt like he could cum into his pants right then watching his grandma being so dominating with his shy, but incredibly sexy, mom.

Hank was watching it all from the other side of the pool. It all felt so wrong and awkward to Jake, but he couldn't help himself from getting excited. Of course, he was always aware of his mother's big breasts and he often got horny when she would wear something a bit more revealing, but he never thought one day he could see her like this.

"Tell us, Jake, isn't your mom the woman you love the most in the world?" Angela asked again.

Jake was mesmerized by the sight. He was staring right into his mother's and his grandmother's naked tits in the warm summer sun. They were both absolutely perfect. He wanted to bury his face in them and suck on their nipples. But he was also absolutely confused about all of this and felt like he's having one of his wet dreams.

"Yes... She is." he managed to say.

"Good." Angela said. "Of course she is. Every boy should love his mom the most in the world. Until his daughter is born, that is, of course."

Jake had no idea what she meant by any of that.

Angela and Lana get out of the pool

Angela got out of the pool and Lana followed closely behind her. Angela pulled her swimsuit back to its place covering her tits, but the white fabric of the swimsuit was so thin that you could still see everything through it, now that it was all wet.

Lana, however, did not fix her bikini. It seemed like she was only doing what Angela told her and since she didn't get the permission to cover herself up, her breasts were still on full display, swaying and bouncing softly as she walked.

Angela and Lana walked to the deck chairs and Angela took the sunscreen from the table. She showed Lana to lie down on the deck chair and squirted some sunscreen over her breasts.

Jake was still in the pool and watched all of it with fascination. His mom who always acted properly and was a perfect lady was now obeying every word from his grandmother. He was still absolutely bewildered by the situation and couldn't understand why this was happening.

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

As his eyes were fixated on his mother's breasts and his mind was racing he didn't even notice that his grandfather also got out of the pool and was now walking towards Lana. He walked up to her, leaned down and said something to her in her ear.

Hank was 60 and looked like it. Unlike his wife who kept in shape, Hank had a belly and was mostly bald by now. He still kept his charm and was always in a good mood, ready to crack jokes.

Jake watched as his grandfather sat down next to his mother and started applying sunscreen. First he rubbed it on Lana's belly, but soon he started massaging her big bare breasts.

"Why is mom letting grandpa do this?!" Jake thought, shocked at the sight.

"My grandmother is standing next to my mom in a see through swimsuit and grandfather is groping her breasts. This is surely the most obscene sight ever..."

Jake saw his mom close her eyes, and his grandfather kept on massaging her tits. Now and then he would tease her nipples or give a harder squeeze to one of the soft, heavy breasts.

Angela looked at Jake and smiled at him. His grandmother was still a knockout at 55. His dick twitched in his pants as he looked at her breasts, clearly visible in the sun through the wet, transparent swimsuit.

"Jake, what do you think of all this?" Angela asked suddenly.

Jake had zero idea what to think of it. He understood nothing about the situation.

"I... I don't know." He said.

"Do you want your mom to enjoy herself?" Angela asked.

"Yeah, I suppose..." Jake answered, having no idea what his grandmother was really asking.

"Good. That's what we're doing right now. Your mom needs to get relaxed and should be treated like a princess. After all, she endured the long 18 year long wait, raising you properly to becoming a handsome, strong young man. Don't you agree that she deserves to be rewarded for that?" Angela continued with her questions that seemed mostly rhetorical, but still, she waited for Jake to respond to each one.

"Yes, I agree." Jake said.

"Now, come here, honey." Angela said to Jake.

Jake got out of the pool and walked over to them. Hank was still dutifully massaging Lana's big tits. He was wearing speedos and Jake now noticed that his grandfather had a huge erection.

Angela placed her hand around him and pulled him closer to her, he could feel the wetness of her swimsuit on his skin and the softness of her boobs on his arm. They were both facing Lana and Hank and had a great view of the ongoing boob massage.

"Isn't she beautiful?" Angela said.

Jake stayed quiet this time and just watched, his own erection also very obvious.

"Take the towel and dry yourself off a bit." Angela told him. "Then go inside, to the living room and bring me the little red bag from the coffee table. Don't peek at what's inside, it's a surprise for you and your mom." She gave him a little tap on the butt as he headed for the house.

He soon returned with the little red bag and handed it to Angela.

"You didn't peek?" Angela teased, smiling.

"I didn't." Jake said with a serious tone. It was hard for him to force a smile, the whole situation was so bizarre that he still expected to wake up from this crazy lucid dream.

"Now, Jake, it's time for your first test as a man." Angela said.

"A test?" Jake asked. "Why does she have to be so cryptic about everything? Just tell me what's going on already!" He wanted to say, but managed to remain patient.

Angela pulled the contents of the bag on the table. There was a small black box and a bottle of lube.

"A lube?! What the hell does she need that for?" Jake stared at the small black box, dreading what surprise was in there.

At that moment Hank finally stopped fondling Lana's breasts and stood up.

"Lana, get into position". Hank said. "Just like we said. That's it, on all fours. Yes, just like that." He continued as he helped Lana turn over on the deck chair and get on her knees. She lowered her head down and only her big, firm, round ass was now sticking up, pointing straight towards Jake.

Jake was mesmerized by the sight of the red thong between his mother's ass cheeks and the small patch of clothing barely covering her pussy.

Just an hour before he never saw his mother be anything but perfectly proper and decent all the time, and now she was here almost completely naked, sticking her ass out for him to feast his eyes.

Angela handed the small black box to Jake. "Open it, honey."

Jake slowly opened the box and saw a shiny, round metal object inside.

"Do you know what this is?" Angela asked.

"An... ass plug..." Jake muttered.

"Haha, you sure are well informed." Angela laughed. "That's right. It's a gift for your mom. And a test for you." She said.

"What?..." Jake asked, trying to figure out what that might mean.

"First family test for a young man is his ability to self-control. A man can't be trusted if he can show restraint." Angela said with some sternness in her voice.

"So, Jake, do you have any idea what the test is?" Angela asked as she got close to Lana's deck chair and slowly caressed the beautiful round butt.

"I... don't..." Jake barely managed to say. He had the biggest lump in his throat.

"It's simple. You need to give this gift to your mother without cumming into your pants." Angela said and squeezed Lana's ass.

Jake just stood there frozen. "She wants me to do what?..." He thought, his dick throbbing in his swim trunks at the thought of even touching his mother while she was in this position.

"Was I not clear enough, honey?" Jake's grandma gave him that devilish smile again.

"Let me make it clearer. Take that little but plug, spread your mom's ass cheeks and stick it inside. She needs it." She said and Jake almost came in his pants. His grandmother talking like that was the sexiest thing he ever heard in his life.

"Don't forget the lube, of course." Angela laughed. "Your mom is a proper lady, her ass hasn't been trained yet. You need to be very gentle."

Jake just stood there. "I can't..." He said.

Angela gave Lana's ass a little squeeze and, as if she took that as a signal, Lana turned her head around and looked Jake in the eyes for the first time since she put on that string bikini.

"Please, Jake, put that but plug in my butt." Her face showed shame and lust at the same time. Jake thought he might faint. The rush of blood to his head was almost too much.

He took the but plug and the lube from the table and got closer to Lana's ass.

"Now it's all up to you." Angela said as she and Hank stepped back to enjoy the view of mother and son about to cross the line of taboo for the first time. It was a sight to cherish.

Jake sat down on the deck chair next to Lana and he had full access to her ass with both hands.

"Be gentle with me, honey." His mom said softly.

That almost made him cum. She was using her sweetest voice while in this position. Jake was sure no one in the world was ever as horny as he was at that moment.

"She's waiting, Jake. Pull the bikini to the side." Angela said.

He slowly tried to grab the string without even touching the skin, but failed, his fingers were shaking. "I just touched my mom's ass"

He finally managed to calm down enough to control his fingers to grab the string and pull it out from between the ass cheeks and to the side.

Lana's bare pussy and anus were now on full display and Jake felt dizzy again.

"You have to put some lube on it first." Angela instructed.

Jake didn't think he had it in him. Just lightly touching the skin of his mom's ass almost made him jizz in his pants. If he touches her asshole he honestly thought he might faint.

"Please, Jake, put lube on my little asshole." His mother whispered.

At that moment Jake noticed that her pussy was visibly wet.

"She's turned on by this?! Why is mom acting like this!? She was always the most ladylike woman I knew. What got into her!?" He taught, staring at the wet pussy and the beautiful tight asshole in front of him.

"Go on honey, give your mother what she needs." Angela said, smiling lovingly.

"Put some on your finger and spread it gently all over her pretty asshole."

This was all so unbelievable, Jake felt like he was in some sort of trance.

He put a little bit of lube on top of his index finger and looked at his mother's ass.