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Day: 132

"Now it's your turn to ask the questions," I said, eager to see what she would come up with.

"What can I ask, what can I ask... mmmm. Are you rough in bed?" Lily asked, a mischievous gleam in her eyes.

"It depends on the girls," I replied, considering the question carefully.

"So for Grace, gentle or rough?" she asked.

"Of course gentle. Grace won't be able to take the full force," I replied, thinking of Grace's delicate nature. "And I don't think I can do that to her anyway."

"Aww, you love her so much that you don't even want to give her pain pleasure. I wish you would care about me as you do about her," she said.

"I also care about you, but in a different way," I replied.

"I know. Then what about me? Gentle or rough?" she asked, her gaze lingering on me expectantly.

"I guess you'll find out the day after tomorrow," I replied.

"Can't wait for our date. Ooh ooh, what about Mom?" she asked.

"What? Are you losing your mind?" I said, taken aback by her question.

"Sorry, sorry, I didn't mean it like that," Lily apologized, her words a mix of sorry and explanation. "Emily, Nicole, and Grace are all the same size, so I just asked about Grace. Mom is the biggest and thickest girl here, so it just slipped out."

"Come on, don't try to change me in one day," I replied, chuckling at her persistence.

"Don't get angry, but are you into older women?" she asked.

"Yes, and don't try to relate this with Mom now," I said, trying to steer the conversation away from the Mom-son incest. I already broke one, so I really don't want to cross that one too.

"I won't. But then the rumor was true that you were seeing Liam's mom?" she asked.

"She was single, and she's pretty hot. Can you blame me?" I asked.

"Nobody was blaming you. They were admiring you, or at least I do," she said.

"I see, jealous then. Didn't you say you always see me as your boyfriend? How come you're not jealous when I date other girls?" I asked, genuinely curious about her perspective.

"Who said I'm not jealous? But I also like to see you in action," she said. "I still can't believe you did it with Liam's Mom. She was the hottest mom in our neighborhood. Not just our neighbor, she was the hottest woman in our town. She was a lingerie model before she had Liam."

"Actually, I'm good with older women. They are always thirsty for good sex. You just need to know how to play with words until they wet their panties," I replied.

"Do I know them?" she asked.

"Yes, most of them," I replied.

"What?" She was shocked.

"Don't tell mom. I pretty much fucked every single of her friends," I replied with a chuckle.

"Wow, you're such a player," she said. "Ever fucked them in our house?"

"Yeah, multiple times. But you wouldn't know. I only did it when the house was empty," I replied.

"So they just came to our house for you?" she asked.

"No, it's just Mom was busy with her friends when I was busy with one of her friends in my room," I replied.

"So Mom didn't wonder where her one missing friend was and why the weird sound coming from your room?" she asked.

"Sometimes I hold their mouths shut, and other times, I put on music," I replied.

"Super," she nodded. "Just asking. Does it feel different with experienced women?"

"It's different with every single woman. Nobody is alike," I replied.

"Does it count the pussy too?" she asked.

"Alright, think of it like this: just as no two snowflakes are exactly alike, no two vaginas are either! They've got their own little quirks and patterns inside, but overall, they're built pretty similarly. So, yeah, you might notice some differences, but that's all part of the fun of getting to know someone intimately!"

"I don't get it," she made a dumb face.

"It's just they use it differently. Like blowjobs. You have your own technique. Same mouth but it can differ from time to time," I replied.

"Wow, never think of it like that," she replied.

"Now, you won't ask me who is better, will you?" I naked playfully.

"I don't want to ruin my confidence. But I'll ask one thing. Were Mom's friends tight like me?" she asked.

"My cock is not a foot long, but it's pretty thick, so every pussy feels tight around it," I replied. "I like it more when the pussy grips my cock."

"You know, Mom would feel bad if she knew you were banging her friends," she said.

"Okay, she should have been careful to introduce me to her depraved hot friends," I replied playfully.

"It's so hot to think about you're fucking Mom's friends. You fucked them pretty rough, right?" she asked.

"Not all of them. Only the naughty ones like you," I replied.

"Is it bad that I want to see you fuck older women?" she asked.

"No, not at all. I think that works perfectly for me. Now, only if Nicole and Grace also think like you," I replied.

"I think only Nicole is your problem now. Grace is like a walk in the park for you," she replied, her tone tinged with amusement and teasing.

"I'm not sharing anything with Nicole then," I said.

"That's the smart brother I know," she replied.

"Will you stop grinding now?" I asked as she was grinding her hip on my bulge for a long time. "That's exactly how Grace had her first orgasm."

"I can't blame her. I'm also getting close to having one for myself," she teased.

"Just stop," I replied playfully.

"No, not until you make me," she replied.

I quickly moved, so now I'm on top. Lily tried to push me off, but I grabbed her hands mid-motion. With a quick move, I held her wrists above her head. She struggled and made it even more exciting. I could sense her yielding to my grasp, her body now entirely at my mercy.

"Now I can do anything I want with you. You won't even be able to stop me," I said, a hint of playful dominance in my voice.

"Who said I'll stop you? But if that's your thing, I can roleplay," she replied.

"Not a bad idea, but it'll be pretty hurtful for you," I said.

"You can hurt me," she replied.

"But I don't want to," I replied back and kept staring at her.

"Don't look at me like that," she said.

"Like what?" I asked.

"The way you're looking at me now," she said. "You don't need to wait if you want it now."

"But I want to wait... for you," I said, my voice husky with desire.

I leaned in to kiss Lily. Our lips met with a fervor, igniting a passionate fire between us. I could feel the warmth of her body beneath mine, and the way her lips softened under my touch.

Then I pulled away, and Lily's head instinctively rose, seeking more of it. She was burning with pleasure and desire. When she paused to kiss me again, I leaned in and stole one from her. I couldn't resist devouring her while she was helpless. Her lips were so soft and delicious that I became addicted to her. It was hard to control my urges, but I wanted to make her first time memorable and give her a chance to fulfill her fantasies. There must be something she wants to do with me on our date night.

"So you want me here like this all day?" she inquired, a playful glint in her eyes.

"At least until breakfast," I replied.

Suddenly, my phone rang with Mom's call, abruptly breaking the spell of our intimate moment. I couldn't help but feel a pang of frustration. Breakfast time already? I wanted nothing more than to linger with Lily to tease her for just one more hour. With a reluctant sigh, I released her from beneath me.

"Sorry, Lily. Seems like it's breakfast time," I lamented.

"Next time, then," she replied, giving me a wink as she sat up with a smile. Then she started adjusting her messy hair. "Go on, don't keep Mom waiting."

With a sigh, I rose from the bed and reluctantly tore myself away from her irresistible presence.

"Hey, Mom," I greeted cheerfully, answering the call.

"Put it on speaker," Lily whispered, and I complied, holding my phone between us so we could hear the conversation.

"Morning, sleepyhead. Finally awake, huh?" Mom teased, her voice lighthearted.

"Yeah, just woke up," I replied with a chuckle.

"Sleeping in late, I see. Must have been a good night," she teased further playfully.

Lily giggled softly. Then she quickly pressed her hand against her mouth to stifle any further sound. Her eyes sparkled with mischief as we listened to Mom's playful teasing.

I also couldn't help but laugh at her playful teasing. "Just catching up on some rest, Mom."

"Uh-huh, sure. Well, don't keep your girlfriend waiting too long. She might start to think you're avoiding her," Mom teased.

"Don't worry, Mom," I reassured her.

"Alright, just make sure to behave yourself," she teased before our farewells, leaving me with a smile.

"Wow, I've never seen Mom like this before," Lily remarked. "Is she always like this with you, or just today?"

"Yeap, she's always playful with me," I replied with a shrug. "Why do you ask?"

"Oh, no reason," Lily replied quickly, shooting me a subtle glance. "Just curious about your dynamic with her."

I nodded, understanding her silent message. "Yeah, Mom's always been like this. She likes to tease me, especially about my girlfriends. She introduced me to one of her friend's daughters after my first breakup. It really helped me to overcome it."

"Did you also sleep with her mother?" she asked.

"What do you think?" I asked.

"I think a lot of things, but I need to hear from you," she replied.

"Let's save it for another day," I said.

"Alright then, but I still can't believe mom is so open with you," she said.

"After dealing with you three bitches, she needs someone to bring a little fun into her life," I replied playfully.

"Well, you two seem to be doing a good job of it," she said. "Btw, I never asked. Who gave you 'the talk,' Mom or Dad?"

"Definitely, It was Mom," I affirmed with a chuckle. "Dad's not exactly the talkative type when it comes to that stuff."

"She gave you the talk willingly, or did Dad push it?" Lily prodded.

"You're lucky that I also asked Mom the same question. Actually, it was Mom who wanted to give me the talk, and Dad was happy to hear that he could skip his duty," I replied.

"Wow. Dad let Mom do it even after you're the only son. Dad must be looking for an excuse before Mom even brings it."

"I think it would be awkward if Dad did it. We did talk about girls together but having a sex talk, no way," I replied.

"And here I thought Mom was too shy to give any of us the talk," Lily remarked, her eyebrows raising in surprise.

"I guess she loves me more than you three," I joked, a playful glint in my eye.

"Now it's proven," Lily replied. "How was it, though?"

"I knew the stuff, but she insisted that I needed to hear it from her," I replied with a shrug.

"Maybe she knew you'd become a playboy, haha," Lily joked. "But she gave you the talk even though she knew you knew everything?"

"Yeah. Is it a big deal for you?" I asked, wondering about her perspective on the matter.

Lily shrugged. "I guess not. It's just funny to imagine Mom having that conversation with you."

"Yeah, it was a bit awkward," I admitted with a chuckle. "But Mom did her best to make it informative and not too embarrassing."

"At least she cared enough to give you the talk," Lily remarked.

"Yeah, she did," I agreed. "Maybe she thought I'd make someone pregnant too early, haha."

"How come I've never seen this side of yours?" Lily asked.

"Which side?" I inquired, slightly puzzled.

"That you're a mama's boy," she implied with a playful smirk, teasing me gently.

"You're calling me a mama's boy because Mom is closer to me. And she loves me more than you?" I echoed a hint of amusement at Lily's playful accusation.

Lily chuckled and replied, "Maybe just a little bit."

"Well, can you blame her? After all, I am her favorite," I teased.

Lily rolled her eyes playfully. "Sure, keep telling yourself that."

"You don't believe me?" I asked.

"No, convince me," Lily challenged.

"Have you ever had a drink with her or been to a party?" I countered, raising an eyebrow.

"You drink with her? Did she drink also?" Lily asked surprisingly.

"Yeah, sometimes she even gets wasted. I think she brought me along so I could bring her home after she got wasted," I replied.

"Wow, that's something she never did with us," Lily remarked. "How come she felt comfortable knowing she would be senseless after the party?"

"What do you mean by that?" I asked, sensing her underlying concern.

"I mean. You could have taken advantage of Mom," she pointed out.

"Come on, she's my mom," I replied, dismissing the notion.

"But you were drunk too, weren't you?" Lily pressed.

"I had a drink or two, but I had to drive us back," I explained.

"So you're telling me Mom never acted weird with you, and even if she did, you didn't take advantage of the situation?" Lily probed.

"No, never. Like always, just a peck on the lips if we get too excited. Otherwise, it's always on the cheeks," I replied.

"One last question. What did you do when Mom had a wardrobe malfunction, and she was too drunk to fix it herself?" Lily asked.

"Oh, that? Well, I just helped her out, like anyone would," I replied casually.

"Helped her out, how?" Lily pressed, clearly intrigued.

"You know, adjust her dress; fix any straps or zippers, nothing scandalous," I clarified.

"So you've never taken advantage of the situation?" Lily probed further.

"I've seen something I shouldn't have. If you count that as an advantage, I have to say yes to your question," I answered.

"Now you have to share that with me," she insisted.

"I don't think that's necessary," I replied.

"Please, bro," she begged.

"Okay, but brace yourself," I warned. "One Day, we left the lively cocktail party. I was walking beside my stunning drunk mom, haha."

"What was she wearing?" she asked.

"She was bold that night. It was a deep V-neckline mini dress," I replied.

"How much boobs she was showing?" Lily asked.

"Lily, you're..." she cut me off.

"Just be in the moment and keep sharing," she pushed.

"Her neckline dips lower than usual, revealing a generous amount of cleavage. Actually, she was showing off half of both her beautiful breasts," I replied.

"Beautiful?" she raised her brow.

"You want me to stop?" I asked.

"No, no, keep going. What else did Mom wear?" she asked.

"And high heels," I replied.

"I never saw her go out wearing that revealing dress," Lily exclaimed.

"Actually, she did, but before us. Dad told her to stop wearing skimpy dresses because of you girls," I stated matter-of-factly.

"Then why did Dad allow it again and send you with her instead of him?" Lily asked.

"Oh, Dad didn't. She took me with her so that nobody else would know about it. You guys just thought Mom and I were going out and having a boring dinner," I clarified.

"Now I'm convinced you're her favorite," she admitted. "But holy shit, you guys really did that under our nose, and not a single of us could tell."

"Let's go. Breakfast is probably ready," I said, trying to get up.

"First, finish the story," she insisted, pulling me back into bed.

"What else do you want to know?" I asked.

"I'd love to see her in that dress too, but I'm guessing you don't have any photos of her either," she said. "Tell me how she looked. Don't give me your opinion, okay? Give me a real man's opinion."

"I'd rather not discuss it," I replied. "Let's just go grab breakfast."

"Please, bro. I always shared everything with you," she begged.

"I'll tell you, but I can't give you what you are actually asking," I replied. "Mom looked absolutely stunning. The way that dress hugs her curves and accentuates her figure is just... breathtaking. And that neckline? It's... well, it's definitely turning heads. Let's put it that way."

"I still can't believe she wore a deep v-neck with her D-cup breasts," Lily was surprised.

"Double D," I said.

"What?" she asked.

"It's a DD cup, not a D-cup," I corrected her.

"You sure?" she asked.

"No need to pretend or be shocked. I know, because we've gone shopping together and I also know why you don't. Because Mom doesn't buy anything with you girls," I replied.

"Ouch, that stings," she replied.

"Sorry, couldn't resist," I said with a playful grin.

"You're mean," she pouted.

"I promise I'll make it up to you," I replied, leaning in to plant a quick kiss on her cheek.

"Hmm, that might just be enough," she teased. "Now continue the malfunction part."

"She was drunk. We were heading to my car. I held the car door open for her, a gentlemanly gesture that came naturally. As she maneuvered herself into the seat, I noticed a slight shift in her demeanor. A hint of discomfort that wasn't there before. My eyes quickly darted to her dress, and I saw the problem: the plunging neckline had shifted, and one of her breasts was fully exposed," I paused. "Now, guess what happened?"

"I don't know, but If I were you, I would definitely take a chance to grab them in the name of fixing her dress," she replied. "Maybe one or two squeezes too."

"And why would you do that?" I asked.

"Why not? Have you seen her size? They are huge," she replied, making a hand sign. "You don't like big boobs? As far as I remember, Liam's Mom also had boobs like Mom's."

"You're quite the troublemaker today, aren't you?" I asked with a raised eyebrow.

"I'm just keeping up with the atmosphere," she replied with a mischievous glint. "Okay, what happened next?"

"I guess it wasn't just a wardrobe malfunction causing her discomfort. She looked like she was about to hurl," I replied. "Yeah, Mom had a little too much to drink that night. She wasn't feeling too great."

"Then," she asked.

"She was sitting on the edge of the car seat, and I noticed her face suddenly contorted with discomfort. Without warning, she leaned forward and retched violently, narrowly missing the door frame as she expelled the contents of her stomach onto the ground," I replied. "Luckily, I moved in time."

"Her boobs are still hanging out?" she asked.

"Yeap, but only one of them," I answered. "Then I reached for the tissue box tucked in the car and handed it to Mom. She was too disoriented and drunk to manage it herself, so I took charge and wiped her mouth and face."

"Alright, no need to toot your horn. It was your job," Lily quipped with a playful smirk. "But how did you fix her dress, or did you just ogle her all the way back?"

"Nah, I fixed her dress?" I replied.

"Oh my god. Then you touched her boobies. There is no way you can tuck her boobs without touching them even if it's one of them," She shockingly covered her face.

"I had no choice. Mom was drunk. That was the only way to tuck it in," I replied. "I reach over and gently adjust the fabric of her dress, securing the neckline and ensuring her modesty is preserved."

"So does this happen only once?" she asked.

"A few times," I replied.

"So you have touched her both boobs?" she asked.

"Yes," I replied. "Hey, it was just for a split second."

"Does she know that her sweet son molested her?" Lily asked teasingly.

"She knows that she lost control, and I had to deal with something like this, but we never shared details," I replied.

Lily raised an eyebrow, her playful smirk widening. "Or maybe you conveniently forgot just so you could play hero again, huh?"

"Will you stop teasing me if I say yes?" I asked.

"No, I won't," she replied.

"Then?" I asked.

"You have to share these details with Mom and see if she is still up for this super secret little adventure with you," she said with a mischievous chuckle.

"You want Mom to get mad at me?" I queried.

"Maybe a little. But it would be more interesting if I could see Mom's reaction," Lily replied with a grin.

"Alright, I'll talk about it with her later. Plus, it has been a long time since I have spent some quality time with Mom," I said, nodding. "Let's eat some breakfast. I'm so hungry."