All characters are 18 plus.
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.