Dan the virgin: Part 1 (a fresh cherry to pop)
It’s a soft Saturday dusk when Sofia arrives home from a late community event, guiding a young man by the wrist. He’s tall-ish, skinny in a boyish way—curly hair flopping into wide brown eyes. His cheap cologne tries to mask the anxious sweat rolling down his neck.
His name is Dan—and he just turned 18 not too long ago, still lives with his single dad, never been laid but swears to his locker-room friends he’s “saving it for a real MILF, not some immature high school girl.”
Tonight, Sofia’s about to grant that fantasy—and a little more.
She closes the door behind him with her usual calm, motherly authority. He stands frozen by the hallway coat rack, eyes locked helplessly on the deep curve of her soft hips and the faint sway of her full breasts under her wrap dress.
“Relax, love…” She purrs, stepping closer to fix his rumpled collar.
“You trust me, yes? Tonight we go slow. I’ll teach you everything.”
Dan stammers, voice cracking: “Y-yes, Ms. Sofia— I mean— Sofia— I mean— oh, God, you’re so—
She giggles, kisses his hot cheek. “So polite. So shy. Let’s get you comfortable…”
She leads him by the hand to the big, plush den—the lights low and soft. She pushes him gently onto the couch, climbs into his lap like she weighs nothing, her warm thighs hugging his narrow hips.
Dan tries not to moan when she rocks once—just enough for him to feel the thick warmth of her plush bottom against his painfully hard cock straining his jeans.
Sofia cups his face with both hands, her voice a whisper: “You’ve never done this, hm? You’ve only dreamed?”
He nods frantically, biting his lip.
“Tonight is your first time. And your first lesson…”
She kisses him slow—one hand slipping into his hair, the other drifting down to squeeze his thigh. His fingers twitch, desperate to touch her huge breasts but too shy to grab.
Dan’s brain is mid-fantasy—“I’m gonna lose it to the hottest MILF ever”—when a soft laugh bubbles from the hallway.
Riley appears, sleepy and pretty as ever: loose tank top slipping off one shoulder, soft lounge shorts, hair tousled like they just woke up. They pause in the doorway, blinking curiously at the sight of Sofia on this trembling boy’s lap.
Riley’s soft voice, gentle but sly: “Oh? Did Sofia bring home a new boy toy?”
Dan freezes. His eyes drag from Sofia’s cleavage to Riley’s delicate collarbone… then lower. The soft curve of Riley’s thighs. The shy sway of their narrow hips. The faint line of a bulge under those shorts.
It hits him like a car crash: “Wait. Boys aren’t supposed to look this…pretty. F-Fuck.”
His cock twitches again, harder than before.
Sofia smiles—motherly but mischievous. She feels his lap twitch under her plush weight and purrs at Riley: “Come here, Riley babe. He’s never touched anyone before. He wanted me to pop his cherry—but I think now he wants to see you first.”
Dan chokes, cheeks flaming. His voice is a broken squeak: “No, I— I mean yes— I don’t know— oh God—”
Riley pads over, slips between Sofia’s knees, cups Dan’s blushing face in both small, soft palms—their smile wickedly shy.
“Relax, cutie pie. You’re gonna love it. You can watch… or maybe taste, too…”