The Woman You Love the Most

Characters in this chapter:

Jake (18yo)

Lana - Jake's mother

Angela and Hank - Jake's grandparents (father's side)

Richard (68yo) - Hank's brother

Hanah - Richard's daughter

Monica (18yo) - Hanah's daughter / Richard's granddaughter

Short recap of the Part 1: Jake just turned 18 and is visiting his grandparents with his mother. His grandmother, Angela, reveals that he is now ready to join the family tradition and leads him and his mother through a series of taboo scenarios.

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*********Second day at grandma's*********

After the day he had, Jake fell asleep quite early and woke up around 9 the next day, feeling well rested. As he was waking up it took him a minute to realize that what happened yesterday wasn't just a crazy dream he just had. Then he felt the annoying metal thing under his boxers and the feeling made him think of his mother. Now that he slept on it it all seemed even crazier.

"What the hell was all that?! Grandma kept mentioning some tradition, but didn't explain anything." He thought as he got dressed. "I gotta tell her to get this thing off me. This is ridiculous".

He went downstairs and found no one there. He got some breakfast and then returned to his room to play a video game on his laptop, expecting to hear his grandmother calling him to come down sooner or later.

It was a little past noon when he heard a knock on his bedroom door and saw his grandmother enter.

"Hey sweetie, did you sleep well?" Angela asked.

"Yeah, great."

Jake looked at her and kept thinking how hot his grandmother is. She was wearing a tight casual dress that revealed most of her fit tanned legs.

Angela noticed his glare and smiled. Even though she was used to getting looks from men, she found it especially flattering when she'd catch a very young man staring at her. The fact that her own teenage grandson couldn't help himself from staring at her titts made her horny.

Slowly she lowered her eyes to his crotch and let out a small giggle. Jake frowned a bit.

"Is she mocking me?!" Jake thought and frowned a little.

"Would you like to get rid of this thing?" Angela asked, teasing him.

"Yeah."

"I know you would. But do you think you can control yourself better today?"

"I'll try."

Good. We have to continue with your practice so you can be ready for the big event."

"What big event? What are you talking about?!" Jake raised his voice a little, irritated by this repeated vague talk about some tradition or whatever.

"Patience sweetie. The big event where you and your mom will officially become a part of our family tradition." She said calmly. "But don't worry about that just now. Come with me now, let's set your little friend free."

He followed her downstairs and kept looking at her ass. Her dress was tight around her waist and emphasized the shape of her body perfectly. They entered the living room and found Lana sitting on a couch in a light summer dress. Her face got a bit red when she saw Jake.

"Lana, what do you think? Does Jake deserve another chance today? Shall we release his caged little friend?"

"Yes." Lana answered right away.

"Do you think your mother just wants to tease you and make you fail your tests again?" Angela turned to Jake and laughed.

Jake watched his mother smiling shyly and realized he was barely recognizing her with the way she was acting.

*******Backstory: Jake and Lana*******

He knew his mother as a calm and composed woman who everyone liked for her cheerful personality. He probably saw her drink too much wine on special occasions once or twice at house parties, and even then she remained perfectly ladylike. She just seemed to laugh at everything a bit too loud and was even friendlier than usual with everybody.

The only time he saw her in a completely different light was a couple of years ago when he came home from school early.

He entered the house and heard a woman's voice coming from the living room. He always had some voyeuristic tendencies so he instantly got curious, quietly sneaked through the hallway and peeped into the living room.

There was his mother on the couch, lying on her back with both feet spread in the air. She was wearing a bathrobe which was completely open and Jake could clearly see her naked body. He thought she had the most perfect big boobs he ever saw and her pussy was completely shaven.

Her hair was wet so she obviously just got out of the shower and thought she had the house for herself for at least another hour.

There was a laptop on the coffee table in front of her and a video was playing. He couldn't see the screen very well but it looked like there was a blonde woman talking dirty as two older men were having their way with her. It seemed like a pretty hardcore amateur video.

Jake watched his mother as she rubbed her pussy while watching the video. One of the men in the video started fucking the woman and Jake saw his mother pick up a big cucumber she had next to her. She rubbed it a few times against her wet pussy before she started sliding it in.

He was shocked by the size of the cucumber. At first he thought that there was no way that his mother could take something so wide inside her pussy, but soon she was fucking herself with it as fast as she could and moaned in pleasure.

"Oh yeah... fuck me like that... fuck my pussy..." Lana moaned softly with her eyes closed while the big vegetable ravaged her pussy.

The rush of blood from the excitement made Jake feel dizzy and he decided to get out of there before he got caught. He thought it would be best to sneak back to the front door and close them loudly so he could pretend like he just came in. He heard the sounds from the living room video suddenly stop after he slammed the door. His heart was racing and he went straight for the stairs, up to his room.

A few minutes later Lana knocked on his bedroom door and entered, still wearing the bathrobe and he knew she had nothing underneath. He couldn't get the image of his mother's big heavy breasts out of his head and was still rock hard from thinking about the whole scene he just witnessed.

"Hey honey, you didn't come say hi when you came in." She said. "How come you're home already? Is everything okay?"

"Yeah, all good. They just canceled the last class today." Jake said. He was visibly red in the face.

"Okay." She said and walked over to where he was sitting at his PC desk and placed her hand on his shoulder. Her bathrobe was tied rather loosely and revealed a lot of cleavage. It was impossible to ignore Lana's big tits even without cleavage and Jake was used to noticing men staring at her whenever they were somewhere in public.

She leaned forward on his desk still facing him and both of her boobs almost fell out, but the bathrobe held just enough to prevent that. She looked him in the eyes and he had to muster all of his willpower not to lower his look at the huge cleavage in front of him.

"I'm gonna go make lunch. Is there something you'd like me to make?" Lana asked with a smile and placed a hand on his cheek.

"Anything's fine." Jake answered and his eyes betrayed him and went to his mother's soft breasts. Even if it was just for a second, it was too obvious for her not to notice.

She smiled at him and straightened herself back up but didn't bother to fix her bathrobe in the slightest. Jake was trying to look away but then she leaned over him to give him a kiss on the forehead and for those two seconds he had a clear look inside of her bathrobe at one of her boobs. The smell of her body lotion was intoxicating.

She turned and went to the door and then stopped.

"Love you, honey." She smiled warmly.

"Love you, mom." Jake replied, captivated by the beauty of the woman in front of him.

An hour later his father and younger sister got home and the lunch was ready. There was chicken meat and rice, but what got his attention was the salad that Lana placed between herself and Jake. He knew that his sister and father ate only green salad so Lana made a separate one for them.

"I hope you like the salad, Jake." Lana said. "I made it just the way you like it, with lots of cucumber."

She chuckled quietly and bit her lip. It was definitely the best salad he ever had.

********End of backstory********

"Go over to your mom and drop your shorts." Angela said.

"What?" Jake looked at his grandmother shocked by the sudden order.

"Do you want to get rid of that thing or not? Drop down your pants and let your mom take care of it."

He hesitated for a few seconds but knew that there was no point arguing. He dropped his shorts and boxers to his ankles and was now standing right in front of Lana.

Angela got closer to get a better look also. "Don't you feel guilty for making his penis suffer like this with your lewd body?" She asked Lana teasingly.

"I do..." Lana replied blushing, looking at her son's caged cock.

"I think he deserves another chance today. He had enough punishment for yesterday's failure to control himself." Angela said and offered a small key to Lana.

Lana took the key and kept staring at the cock cage in front of her.

Jake just realized that although he touched his mother yesterday in the most perverted ways, she hasn't touched him once. He felt like this was another taboo entirely that was about to be crossed.

"You're so cruel, Lana! After he endured a whole day with his penis trapped like this you're still making him wait longer." Angela egged her on.

Jake looked down at his mother's soft hands as she gently raised the cock cage to insert the key and felt relief when the buckle clicked open. Finally, his dick was free again, standing rock hard in front of his mother.

********Richard and Monica visit********

A few hours later a big black Range Rover drove up the driveway and Richard and Monica stepped out. With them was another blonde woman and it took Jake a few seconds to recognize her. He hasn't seen Monica's mother, Hanah, for over 5 years, but she didn't actually change that much.

"Lana, I haven't seen you for so long! How are you? You look great!" Hanah said with sincere friendliness and gave her a hug.

"Hi Hanah. You look wonderful too." Lana replied.

Hanah was 40 and was still in great shape. She was skinnier than Lana and her breasts were noticeably smaller than Lana's double Ds, but she was still a very attractive woman. Her blonde hair falling over her shoulders and her pretty face easily charmed any man.

"And Jake, look at you. You have grown so much since I last saw you." She said as she hugged him.

Both her and Monica were wearing very short mini skirts and Jake kept looking at their butts.

"So, you ready, Lana?" Hanah asked and Jake realized that his mother was all dressed up and she was even wearing makeup.

He was about to ask where they were going when Angela put her arm around him.

"Today you and I will spend some time together, your mother has other things to attend to today." She said to him and they watched his mother get in the backseat of a car with Monica. Hanah took the front seat and Richard waved to Jake as he drove away with the three ladies.

"Where are they going?" Jake finally asked.

"Your mom and Monica need a dress for the party on saturday." Angela replied like that was obvious.

"A dress? Why won't you tell me anything?" Jake was visibly irritated by the constant vague replies. Angela laughed like he told her the funniest story.

"You're so cute when you're angry. Okay, come with me and I'll show you something."

********Angela's wedding dress********

Jake followed his grandmother upstairs to her room where she told him to sit on the bed as she went for the closet.

"You and Monica are now 18, and on Saturday we will have a party for you and her to celebrate you joining the family tradition. Of course, your mother is your partner in the celebration. And for Monica, it's gonna be her grandfather, Richard (because, as you know, her father was never in the picture)."

"What do you mean "partner"?" Jake asked.

Angela unzipped her dress and let it drop on the floor. She was wearing a lace bra on and Jake could see her nipples through it. She wore a matching see-through panties.

"Do you want to see what kind of a dress your mom is getting right now?" She asked while Jake stared at her large breasts. He didn't even try to pretend that he wasn't staring at her body. He knew that she was teasing him on purpose so he figured there was no point in denying himself the opportunity to freely look at such a perfect pair of titts.

"Yeah."

"She reached in the back of the closet and pulled out a large box and laid it on the bed next to him.

"Open it." She said.

Jake removed the cover and saw the silky white fabric. On top were a pair of white stockings and a white g-string.

"What is this?" He asked.

"What does it look like?"

"A... a wedding dress?" He asked, not really knowing what to make of it.

Angela took out the dress and laid it on the bed. It was a very short dress that was mostly transparent, except for the breast cups. It looked nothing like any wedding dress he ever saw before, that was for sure.

"Do you want to see me in it?" Angela smiled, standing in front of him in her bra and panties.

"Yes." Jake muttered.

"Haha, how did I know you would?" She laughed. "Well then, you'll need to help me."

She threw herself on the bed next to him and raised her legs up. "Take off my panties."

He stood in front of her and pulled the sexy black panties from under her ass as she wiggled it a little.

"You can keep those as a souvenir if you want." She teased him and still held her legs up towards the ceiling. Jake watched his grandmother's shaved pussy and wanted to bury his face in it. He put the panties in his pocket and knew he would sniff on them later. "I really am a pervert." He thought.

"On Saturday your mom will become your bride, so, obviously, she needs to get a wedding dress today." Angela said while taking off her bra.

"What is that supposed to mean?" Jake asked. He was rock hard watching his naked grandmother lying on the bed in front of him.

"Let me demonstrate. Come here." She said and Jake sat down on the edge of the bed next to her beautifully tanned legs. She got on her knees behind him and kissed him on the neck and reached around to grab his penis over his shorts and felt it throb.

"Sit here and enjoy. I haven't worn it in years, I hope it still fits me." She got off the bed and slowly put on the g-string. She turned around to look at herself in the mirror, and also to give Jake a better look at her ass.

"You men can't get involved while the bride is getting ready, so you're getting a special treatment here watching me put this on." Angela teased her grandson, enjoying every second of knowing that his eyes are glued to her and how hard he is from watching her.

"Uncle Richard went with them today. How come he is involved?" Jake asked.

"Oh, he's just a driver for the ladies today. Hanah is the one who will help your mom and Monica with everything. But also, you are not in the same position as uncle Richard since you're just entering the family tradition while he has been a part of it for a long time. So don't worry about him, your role is much more special and interesting." Angela said and pulled on her g-strings, pretending to fix it, but she just wanted to wiggle her ass some more for Jake.

"Besides, I'm making you company here. Don't tell me you're jealous for not going with them. Am I not fun enough?" She pouted jokingly.

She sat on the bed again, took out the white stockings from the box and started putting them on slowly. Jake watched her every move and imagined kissing her thick thighs.

Angela stood up on the bed and looked down at Jake. She moved like a playful schoolgirl and it drove Jake nuts watching her large, heavy titts swing freely. He couldn't think of a woman he'd rather fuck right now than the sexy mature woman in front of him, that happened to be his grandmother. Well, except his mother.

"Let's play a little game. You need to earn seeing me in that dress, so you need to pass a test first." She said and got down on her knees so she was eye level with Jake.

Jake definitely wanted to see what "game" she had in mind. He was sure it would drive him insane, but he was also determined to pass the test this time. He wasn't going to wear that damn cock cage thing again.

"So, the rules to pass the test are simple. You can't cum." She said and gave him a quick kiss on the lips and giggled.

"Why the hell didn't I jerk off earlier today?" He thought. "It would make this so much easier."

"I'll even let you choose. Kissing test or sucking test?"

Jake thought about it. "What's a sucking test?" He asked.

"Haha, I can't tell you more than that. Choose whichever sounds like you can pass it." She said amused by his hesitation and flicked her hair over her nipples to tease him.

"Kissing test, I guess." He said, already doubting his choice. Is he really going to make out with his grandmother on her bed?

Without a word she took off his shirt and pulled down his shorts. He was left only with his boxers still on.

"Lie down." She instructed and he listened. She went for the drawer and pulled out a pair of pink handcuffs.

"Wait, can we do it without that?" Jake asked, a bit worried. He was quite ticklish and he wasn't crazy about the idea of having his arms tied.

Angela just giggled and hopped on the bed again and then straddled him cowgirl style. She held his left wrist and clicked the handcuff on it, and then closed the other side on the bed frame. Jake tried to dissuade her before she did the same with his other wrist. She pressed her huge titts in his face as she clicked the other handcuff on the bedframe and laughed happily watching her grandson bound on her bed.

"Oh, I have an idea!" She said and took her phone from the nightstand.

She giggled wickedly while she took a photo of him.

"Aaand - Sent."

"What?! Who did you send that to?"

"Your mother, of course." Angela laughed. "So she knows she's not the only one having fun today."

"Now, let's start with your test." She said and dropped down on his chest while in a cowgirl position and kissed him lightly on the lips. He felt her big titts on his chest and desperately wanted to grab her ass.

"How many girls have you kissed? You're a cute boy, I'm sure horny girls at your school are all over you." She asked and started kissing his neck.

"Three, I think."

"You think? Only three?! And how many girls have you slept with?" She asked and slowly started moving her hips. She still had those white stockings and a g-string on.

He thought about lying for a second, it was a bit embarrassing that he was still a virgin at 18. Most of his friends lost their virginity but he was simply unlucky. He was close to doing it with a cute girl from school that he dated for a month. They were naked in her room and extremely nervous. She was very shy about all of it and they weren't relaxed at all, but he was hard and already put the condom on when they heard her parents drive up to the house. She got so scared about almost getting caught and stopped answering his texts after that day.

"Zero." He replied truthfully.

"Oh, my sweet baby." Angela suddenly seemed extremely turned on and started grinding his dick faster and kissed his neck and ears while breathing heavily.

His dick was rock hard and lined up perfectly against her pussy. She was so dripping wet that he already felt the wetness through his boxers.

"My sweet boy. Fuck me. Fuck your slutty grandma. Fuck my dirty little cunt, Jake." She whispered in his ear and then stuck her tongue in his mouth and kept grinding.

He thought that those three girls he kissed could barely count as "making out" compared to this. Angela's tongue swirled around his mouth and she kept moaning louder and louder. He wished his hands were free so he could grab her sexy hips and her thick ass.