Mom & Aunt Teach Me S*X CHAPTER 5

Chapter 5

June 18, 2026 View all chapters

“Mom… Julie …” I hesitated for a moment, my cheeks warming. “You’re… good-looking too. I mean, really good-looking. You’re just… beautiful in a different way.”

She blinked at me, then smiled softly. “Thanks,” she said. “I’m glad you think so.”

Across from her, Jessica raised an eyebrow and leaned back in her chair, swirling the ice in her glass.

Mom turned to her sister suddenly, her gaze sliding up and down in an almost appraising way. “I’m sure you’ve heard this before,” she said lightly, “but now that I’m looking at you… you’re really hot, Jessica .”

Jessica ’s lips curved into a slow smile. “Thanks. I’m flattered,” she said, her voice softer than usual — almost guarded. “You’ve always praised my looks.” She hesitated, then added with a strange little tilt of her head, “You’ve never been… jealous of me, have you?”

For a beat, Mom didn’t answer. Instead, she brushed the question aside and said, “I haven’t seen you with short hair before. It… suits you.”

Jessica touched the back of her neck self-consciously. “I had it cut shorter for a wedding. Wasn’t sure if it would work on me.”

“I’m glad you cut it,” Mom said, and there was something in her tone I couldn’t quite place. “I’ve always liked you more with short hair.”

I sat there, my glass in my hand, watching the two of them trade quiet compliments like they were playing some secret game I wasn’t part of. They’d always been close, but this… this felt different. Like there was something underneath their words that neither of them was saying out loud.

“Uh, hey, you two,” I interrupted finally, forcing a smile. “Wasn’t I supposed to be the one flirting here? You’re doing a pretty solid job without me.”

They both turned toward me at the same time and — like some kind of synchronized act — giggled. Giggled. At me. Then exchanged a quick glance before settling back into their seats, looking just the tiniest bit self-conscious.

Mom cleared her throat. “You’re right,” she said softly. “We should… continue.”

“Okay, where were we?” Jessica said, holding up her empty glass with a lazy smile. “Other than getting another round.”

“I was flirting with her,” I reminded them.

“Yeah,” Jessica said, smirking. “But you weren’t exactly killing it, kid.”

I squinted at her and leaned back. “I’ll try harder,” I muttered. “You, on the other hand, are doing a great job.”

“Thanks,” she said with an exaggerated little bow in her seat. “But honestly?” She chuckled lightly. “The drinks are definitely helping.”

“Yeah, well,” Mom said, tilting her head at her sister, “you didn’t seem like you were enjoying his attention that much.”

“We didn’t even do anything yet,” I cut in defensively. “She kissed me, sure, but then you two went off on your little sidetrack.”

“Fair,” Mom said with a small laugh. “Alright. Back on track.”

She leaned forward slightly, resting her elbows on the table. “At this point,” she said, fixing me with one of her patient-teacher looks, “you’re supposed to start an actual conversation. Figure out if she likes you.”

“Okay,” I said, scratching the back of my neck. “What exactly am I supposed to do now?”

Mom sighed — loudly, dramatically — and gave me that look, the one she used to give me whenever I forgot my homework as a kid. “ David ,” she said slowly, “converse with her. It shouldn’t be that hard. Just… talk about something.”

I nodded, swallowing my nerves, and turned back to Jessica . “Okay,” I said. “Anything you want me to talk about?”

She leaned forward, resting her chin in her hand, watching me with that same teasing spark in her eyes. “Anything,” she said. “Just… don’t overthink it. Keep it natural.”

I sat there for a moment, racking my brain and coming up blank. The silence started stretching just a little too long, and I almost gave up right then. “How about…” I stalled, fumbling for words. “…we talk about the weather?”

Jessica burst into soft laughter, covering her mouth with her hand. “The weather?” she said between giggles. “Wow. Smooth.”

“Or the news,” I said quickly, half-defensive.

“Literally anything.”

She grinned, sipping her drink before leaning closer — close enough that I could smell her perfume again, warm and faintly sweet.

“Try again, David ,” she said softly. “Something… better this time.”

They both exchanged a glance and let out synchronized sighs.

“Let’s just skip the conversation for now,” Jessica said finally, her voice calm but teasing. “Let’s imagine that you already know I’m interested in you.”

I furrowed my brow. “How would I know that? I’ve never really known if a girl likes me. That’s why… we’re in this situation in the first place.”

Jessica tilted her head thoughtfully. “Well… there are signs. She laughs at what you say, mirrors your movements, licks her lips… looks into your eyes when you talk. There are others too, but it really depends on the girl.”

I swallowed, feeling my pulse quicken. Gathering some courage, I tried to focus on the conversation, pushing my nerves aside. We started talking — about my work, her interests, everything that came to mind. To my surprise, it flowed naturally. Mom occasionally pointed out the little signs Jessica was giving me, and I started to pick up on them.

With each word, I realized I was seeing more of her — not just the funny, teasing aunt I’d known all my life, but someone new, someone vibrant, intriguing. A side of her that felt… unfamiliar, yet captivating.

“ David ,” Jessica said suddenly, smiling warmly. “I have to say, you’re doing really well. Handsome, polite… just a bit more confidence, and girls will fall for you without even trying.”

She got up to stretch and walked toward the drink cabinet. My eyes betrayed me, catching the subtle movements of her body, the way her shirt stretched over her chest. I quickly looked away, my face heating.

Mom’s voice floated from the living room, approving. “I like it when you call him David .”

Jessica glanced back over her shoulder and smiled. “I like calling him David too. It suits him. Strong, sensitive… a good name.” She shook her head slightly, a faint wistfulness in her eyes. “Almost makes me feel like I’m dating my son… not that I am,” she added quickly, laughing softly, and picked up her drink.

Mom’s voice chimed in again, playful. “I’ll go to the little girl’s room for a bit. Then we can start role-playing again.”

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