The Woman You Love the Most

He started driving. It was around a 15 minutes drive to the big shopping center where they were heading. Jake knew the way well since his grandparents took him there every summer when he stayed with them and always bought him something nice he wanted.

He stopped at a traffic light and noticed his mother squirming in the back seat. He adjusted the mirror a little to see what was going on and saw that one of his grandmother's hands was on his mom's breasts and she was groping her slowly over the summer dress. Lana was looking out through the window with her eyes half closed and she was breathing heavily.

Jake couldn't help but picture their asses filled with the butt plugs he put in there. His dick was in constant struggle, trying to get fully hard but being restricted by the cock cage.

They parked in an underground garage and got in the shopping center. Jake observed the way Lana and Angela walked. He wondered what it felt like moving with their asses stuffed like that. The toy in Angela's butt was quite big. He had a hard time comprehending how she moved around normally with that thing inside her.

"Hold your mom's hand, show her you love her." Angela said suddenly.

Lana extended her hand towards Jake and he took it. Angela walked first through the shopping center and Lana and Jake followed behind her, holding hands like a couple. He had a feeling everyone would be looking at them, knowing that something weird is going on. But since nobody knew them in this town, except for the few of his grandparent's friends who visited them while he stayed here, he realized that people had no reason to find it too weird. Yes, there was an obvious age difference, but that's nobody's business.

Angela led them into the large clothing store and into the woman's section. Lana walked slowly between the rows of clothes, looking at the dresses, feeling the fabric. All the while she didn't let go of Jake's hand and he walked with her. His dick calmed down a little and he started enjoying the feeling of his mother's hand without the uncomfortable feeling in his pants. He felt her perfume and watched her figure in that light summer dress as she picked the clothes to try on.

They went into the changing room and Angela followed them. Angela and Lana went into the changing booth and left Jake outside to wait for them to change.

A little while later Lana came out wearing a t-shirt that seemed too small for her as her breasts were stretching it to its limits, and denim hot pants.

"What an obscene sight." Jake thought.

"What do you think?" Asked Angela. "I picked this for your mom."

"She's not going to stay dressed like that here, right?" Jake asked, seriously worried that his grandmother is planning to make his mother walk around the shopping center full of people dressed like a southern slut.

"Don't worry, she's just trying it on." Angela laughed. "You didn't say if you liked it or not."

"I do." Jake replied and watched his mothers soft thighs.

Angela made her turn around a couple of times so Jake can get a good look from all angles.

"Beautiful, isn't she?" Angela encouraged him to comment on his mother's looks some more.

"She is." Jake replied briefly.

Lana changed back into her summer dress and they headed for the next store. Angela picked some bras and bikinis for Lana but they only let Jake see a few of them. He was almost glad as his poor penis had more than enough torture and needed a rest from getting erect constantly.

In the next store there was a big selection of sexy lingerie and outfits.

"One of my favorite stores here, they have a lot of nice stuff." Angela said. "Jake, now it's your turn to pick."

Jake looked at her, surprised. "Pick what?"

"Pick something for your mom, of course." Angela said, smiling.

She came behind Lana, put her arms around her waist and then cupped both of her boobs in her hands. "Something nice for these beauties." Angela said and shook Lana's breasts a little.

"Or maybe you're more interested to see her butt in some tight clothes?" She continued and gave Lana a quick spank that made Lana jump a little.

Lana took Jake's hand like she already got completely used to that and they walked through the rows of women's sexy underwear and various lingerie.

Jake had no idea what to pick. Everything looked great, and everything looked way too much for his mother to wear.

He realized they were together out of earshot from his grandmother for the first time since all this craziness started. He didn't know if he should say something or ask his mom how she felt about this. But he got his answer when Lana spoke looking at sexy black stockings.

"Please pick something like these for me, honey." She said quietly.

She was obviously on board with all this, so Jake decided not to comment on anything.

"I will." Jake said and felt Lana squeeze his hand lightly and caress the top of his hand with her thumb.

Jake picked a few very sexy looking stockings and a pair of pantyhose. He always had a fetish for those and loved seeing his mom's sexy legs when she was wearing a pair of thin black pantyhose.

He saw his grandmother approaching them and the store lady was coming with her. It was a young woman, around 25, dressed very nicely, wearing high heels and a pencil skirt. He noticed the woman checking out his mother and him intensely. They were still holding hands and this lady obviously thought they were a strange couple.

"Jake, honey, this nice young lady offered to help you choose something for your fiance." Angela said and smiled devilishly. His grandmother was obviously determined in making his life difficult today, he thought.

"Hi, I'm Kelly. How can I help you?" The store lady said politely.

"Can you please show them the outfits you showed me over there." Angela pointed back to where she and the store lady came.

"Sure, follow me, please." Kelly said.

All four of them followed Kelly into a section with various ladies outfits. It seemed like a fetish section. There were all the classics like a sexy nurse uniform, schoolgirl uniform, Playboy bunny costume, etc.

Kelly tried staying completely professional, but she could help but thinking what a strange group this was. "A grandmother coming along with her grandson and his girlfriend to pick sexy underwear and outfits. And his girlfriend looked at least 10 years older than him." She thought.

Jake looked at the huge offer of insanely sexy costumes and then noticed one that especially caught his eye. It was a nun costume. "Am I really going to pick the naughties one?!" He asked himself. "As if this day can get any crazier, so why not? If my grandmother and my mom can act like crazy sluts I can play along."

He pointed to the nun costume and he felt his mother clench his hand. He wasn't sure what that meant. "Does she like his choice or is she shocked and embarrassed that he picked that outfit in front of the store lady?"

Kelly raised her eyebrows, took a glance at Lana who squirmed a little like she needed to pee. Kelly handed the outfit to Lana. "Here you go. The changing cabins are over there if you want to try it on."

"Can you please come with us?" Angela quickly said not letting Kelly get away. She was visibly getting a little bit uncomfortable and wanted to give this weird group privacy she thought they needed.

"Lana might need some assistance, this outfit seems a bit tricky to put on for the first time." Angela added, knowing that the poor store lady can't say no. The customer is king.

They all went to the changing room and Lana entered one of the cabins. Kelly was hoping she could put on the outfit by herself but soon they heard Lana from the inside saying she's stuck and can't close the zipper. Kelly went inside reluctantly.

"Grandson and grandmother waiting for me to help this woman get dressed like a slut and come out to show it to them?! I've seen all sorts of weirdos coming into the store but these people take the cake." Kelly thought.

"I can tell how weirded out she is." Jake thought. "If only she knew the whole story..."

A few minutes later Kelly and Lana emerged from the cabin. Jake used all his willpower to stop himself from getting erect. The anticipation of seeing his mother wearing such a dirty costume was driving him insane.

Lana was now standing in front of her son and mother in law dressed like some stripper.

"This can't even pass as some sort of a slutty Halloween costume, it's simply too obscene." She thought as the taboo of this whole situation made her tremble.

"What do you think, Jake? How does Lana look?" Angela asked.

"Really nice." Jake replied as he ogled his mother.

Angela walked over to Lana to get a better look. "Yes, I like it too." She said.

"Thank you, Kelly. You were very helpful." She said to the store lady who seemed very relieved that she could get away from this weird group of people and she left the changing room.

When Kelly left them alone Angela stroked Lana's ass, admiring the sexy costume.

"This looks so good on your mother, Jake. I like your taste."

Lana changed back into her dress and Angela paid for the costume.

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

As they were on their way out of the store someone called Angela's name. It was her brother in law, Hank's brother, Richard. He was 68, but still held very well for his age and still had all of his hair. He played lots of sports in his younger years and was still in good shape.

Alongside him was his granddaughter, Monica. She was a very cute girl with beautiful long, blonde hair. She was wearing skinny fit ripped jeans and a light white t-shirt.

"Hey Richard! So glad we ran into you. Are you two also getting ready for the weekend party?" Angela asked while the two of them were approaching.

"What party?" Jake thought.

"Yeah, we can't wait." Richard said cheerfully.

"So you must be here to get a gift for your granddaughter. Happy birthday, honey. When was it? Yesterday, right?" Angela asked Monica.

Monica just nodded.

Jake knew Monica from when she was a kid, but hasn't seen her for years. They lived across the country so there was rarely an opportunity where they would all get together. He also knew that Monica's dad left when she was little.

"Jake, you remember your cousin Monica, right? She just turned 18, just like you." Angela said.

"Yeah, hi." Jake said and then realized his mother was holding his hand this whole time.

"It's so nice seeing mother and son this close." Richard said, referring to the hand holding. "How are you, Lana? We haven't seen each other for years."

"She's great. We just got her a new costume for the party. Jake picked it, it's absolutely wonderful." Angela said before Lana could answer herself.

"For the party? And these two are coming over?! What the hell is grandma talking about?!" Jake thought as he glanced at Monica.

"That's great! Can't wait to see it myself." Richard said.

They went their own ways after that and Angela led them to the upper most level of the shopping center. There were only a couple of small stores here and a movie theater.

"Jake, wait for us here, honey. Your mom and I just need to go to this store quickly." Angela said and they went in.

It wasn't very obvious from the outside but Jake realized that is was a sex toys shop.

He realized he almost forgot about his cock cage already. Slowly getting used to the perverted setting he was in his dick wasn't getting erect so often.

Around 15 minutes later Angela and Lana emerged from the store. He noticed a new accessory on his mother's neck right away. It was a small black collar that was wrapped around her neck pretty tightly.

The other thing that was almost as obvious was that his mother wasn't wearing a bra anymore and her big titts were now swaying freely in her summer dress. But that wasn't all that was different. He noticed that her nipples were sticking out unusually much.

"We had to get a few things for your mom. What do you think?" Angela asked.

He just stared at his mother's breasts trying to figure it out.

"You don't miss a thing." Angela said, laughing, seeing that Jake was so concentrated on Lana's tits.

"I see you like your mom's nipple clamps. I realized that her nipples were seeking attention the whole day. You could see how hard they were even over her bra. So I decided that we need to do something about that." Angela said.

Jake was mesmerized by the way that looked. It wasn't that obvious if you didn't look straight into her tits, but if you looked for more than 2 seconds you would realize there's something there.

"People will probably think she has huge nipple piercings or something." Jake thought. Coupled with the collar on her neck and the thought of the butt plugs in her ass, looking at his mother like this was enough to make his dick want to explode.

"There's one more thing we got for her." Angela showed Jake the small pink device she was holding in her hand. She pressed one of the buttons and Lana crossed her legs like she needed to pee and her whole body shook a little.

"What is going on?!" Jake thought, watching his mother still squirm a bit.

Lana looked at Angela and the look in her eyes was pure lust. Angela pressed the button again and Lana started trembling again and moaned a little.

"Your mother has a fun little device in her panties. As you can see I can control that device with this little thing here."

"Holy shit!" Jake thought. "How is mom letting all of this happen? Why is she letting grandma have her way with her like this!?"

"I think your mom is very horny, honey. I think she needs some fresh air." Angela said and watched Lana's lustful eyes and the lewd expressions on her face.

*****In the park*****

Outside of the shopping center there was a big park with benches, trees and a small pond. On a nice summer day like this the park was obviously full of people of all kinds.

Angela made Lana walk in front of Jake and herself so that they could enjoy the view of her round ass as it shook a little every time Angela pressed one of the buttons. She wasn't doing it often so Lana never knew when to expect the next vibration in her panties. All she knew was that she was going crazy with horniness and felt that her panties were completely drenched.

Jake was constantly looking around whether the people nearby were noticing anything unusual about his mother. Most people were preoccupied with themselves and people they were with so no one really paid attention to them. For afar you couldn't notice anything unusual about Lana's outfit anyway. She was just a lady in a summer dress taking a walk.

They got close to the pond and Angela suggested they sit down on the bench. The bench was facing the pond and when got to it Angela told Jake to sit down first.

"Jake, honey, would you make your grandma happy and grant her a wish?" Angela said when Jake sat down on the bench.

"Um, sure." Jake wondered what she had in mind now, but he was pretty sure it wasn't going to be something you'd normally expect. He was getting used to expecting the unexpected from his grandmother.

"Let me sit on your lap." Angela said. "I know my ass is a bit big, but you're a strong young man."

Jake definitely didn't expect that and he knew she wasn't really asking for permission. His grandmother somehow had control over him and his mother and he felt like he couldn't say "no" to her anymore. Not that he wanted to say no to this. He was checking out his grandmother's ass constantly for years when they were by the pool. It was still so round and firm, it was hard to believe she was 55.

"Okay." He simply said and waited for the mature ass of his grandmother to lower itself on his lap.

She sat with her legs to the side of him and then leaned on him to give him a hug and a kiss on the cheek. "She smells so nice." He thought.

"I can feel your little cock cage." She smiled and wiggled her ass. That made him hard instantly and she knew it.

"Did my ass make your little friend get up?" She asked.

"Yeah." He knew there was no point in lying.

"Does it hurt?" She asked.

"A little."

"Oh, you poor boy, I'm sorry. But it's for your own good, trust me." She said and put her arms around his head and pulled his face into her cleavage.

The feeling of the soft skin of her boobs on his face would be enough to make him cum if it wasn't for the little bit of pain that the cock cage was causing him.

"Lana, honey, what do you think? Do we make a cute couple?" Angela asked Lana who was watching her son and his grandma sitting like they were a teenage couple.

"You do. Very cute." Lana replied.

"Do you see what a good son you have, Lana? Do you see how willing he is to endure the torture of his cock for you?"

"Yes. Jake is such a wonderful boy." Lana said and felt the vibration on her pussy as Angela pressed and held the button.

"Why don't you lie down on the grass." Angela said and pointed in front of where her and Jake were sitting.

The whole park was covered with nicely cut soft green grass. As Lana slowly sat down on the grass Jake could hear the buzzing sound again. It was coming from his mother's panties as his grandmother pressed the buttons on the little device she was holding.

Lana lied down on her back and closed her eyes. Jake saw how she pressed her thighs together whenever the buzzing sound started. The third time the buzzing started Lana began to moan softly.

Even though he was fascinated by the sight of his mother clearly enjoying the sex toy in her panties in a public park in broad daylight, Jake still kept looking at other people in the park. The closest group of people was at least 50 yards away so no one could easily notice that the woman lying in the grass in front of him was squirming with pleasure.

"Look at your beautiful mother, Jake." Angela said and continued holding the largest button. "Look how happy she is."

At that point his mother didn't seem to hear or care about anything around her anymore. She had her eyes closed and she was tilting her head left and right in the grass. She kept rubbing her thighs together. Suddenly, as if she couldn't take it anymore, she grabbed her big tits with both hands and started pulling on the clamps that were still firmly pinching her swollen nipples. There was a small chain linking the clamps and Jake saw as she pulled the chain over her dress and then squirmed even more, enjoying the pain that her nipples were enduring.

Jake felt his cock twitching in its cage and Angela felt it too on her ass. She turned to him and gave him a small kiss on the lips. He looked at his grandmother's pretty mature face for a second, before she grabbed his face with both hands and stuck her tongue into his mouth.

He felt her hand reach under her ass and she grabbed his balls that were free from the cage.

"What is she doing?! I can't take this!" He thought as she stopped kissing him and started to softly speak into his ear while massaging his balls.

"Listen to your mother's horny moans. Does your little friend enjoy this torture?" She whispered in his ear.

"Look at this beautiful woman that gave birth to you squirming here in public like a shameless little slut."

"I can't take this!" He thought as he heard his mother moan more and more as she fondled her breasts and pulled on the nipple clamps.

His grandmother tickled his balls and kept whispering insanely dirty stuff into his ear. He crossed the point of no return. His dick was trying to break out of its cage and it hurt, but there was nothing that could stop him from cumming anymore.

When he heard his mother's moans get really loud he knew she was having a huge orgasm. It sounded like she was trying her hardest not to scream in pleasure as the little device still buzzed in her drenched panties.