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Chapter 106 - Convincing the Family

I've never loved anyone the way I love Emily. She's warm, clever, and lights up every room she enters. After two years together, I know she's the one I want forever. Proposing feels like the natural next step, but first I have to get through the final hurdle: winning over her family completely. Her mom, Sarah, and her nana, Grace, have always been polite, but there's a lingering skepticism in their eyes whenever marriage comes up. They want to be sure I'm "the right kind of man" for their girl.

We're spending the weekend at their big old house on the outskirts of the city. Emily's asleep upstairs after too much wine at dinner, and I'm downstairs pouring myself a nightcap when Sarah glides into the kitchen. She's wearing a thin silk robe that clings to her full breasts and hips, the belt loosely knotted so the fabric parts just enough to reveal the soft inner curves of her cleavage. The air carries her scent—warm vanilla and something darker, like aged bourbon.

"Couldn't sleep either?" she asks, voice low and velvet.

Grace appears a moment later, moving surprisingly quietly for a woman in her seventies. Her silver hair is pinned loosely, and she's in a long satin nightgown that skims her still-shapely legs. The fabric shimmers as she walks, catching the dim light. Both women regard me with the same knowing smile, and my stomach tightens with a mix of nerves and something hotter.

"We need to have a little chat," Sarah says, pouring herself a glass of the same whiskey I'm holding. She leans against the counter, robe slipping a fraction more. "About Emily. About you."

Grace settles into a chair, crossing her legs so the gown rides up, exposing smooth calf and a hint of thigh. "We love our girl," she says, voice husky with age and something else. "We just want to be sure you can… satisfy her. In every way."

The words hang heavy in the warm kitchen air. My pulse kicks up. "I love her more than anything," I manage. "I'd do anything for her."

Sarah's eyes drop to my crotch, slow and deliberate. "Anything?" She steps closer, the silk of her robe brushing my arm. "Then you won't mind if we… inspect the goods. Just to be sure you measure up."

I swallow hard. My mind flashes to Emily upstairs, trusting, innocent. But the heat radiating from Sarah's body, the faint scent of her arousal mixing with vanilla, clouds my judgment. Grace watches with bright, hungry eyes.

Sarah's fingers trail down my chest, unbuttoning my shirt one slow button at a time. "Relax," she whispers against my ear, breath hot. "We're just measuring."

Grace stands and moves behind me, her hands sliding over my shoulders, down my back. Her touch is surprisingly firm, experienced. Together they guide me to the wide kitchen island, pushing me gently until I'm leaning against it. Sarah's fingers find my belt, unbuckling it with practiced ease. The clink of metal sounds loud in the quiet house.

My jeans slide down, boxers following. My cock springs free, already half-hard from the charged atmosphere. The cool air kisses my skin, then Sarah's warm palm wraps around the base. She inhales sharply.

"Oh my," she murmurs, stroking slowly from root to tip. Her grip is perfect—firm, teasing, thumb circling the head where a bead of precum has already formed. "Look at this, Mama."

Grace steps around, eyes widening appreciatively. "Well, well. He's thicker than I expected." She reaches out, fingers tracing the veins along my shaft, cool at first, then warming against my skin. Both women work in tandem now—one stroking the length while the other cups my heavy balls, rolling them gently.

The sensation is overwhelming: Sarah's soft, manicured hand gliding up and down, slick with my precum; Grace's slightly rougher fingertips exploring every ridge and pulse. Their perfumes mingle—vanilla and something floral from Grace—filling my lungs. My hips jerk involuntarily, and Sarah chuckles low in her throat.

"Sensitive," she observes, squeezing just hard enough to make me groan. "Good. Emily will like that."

They produce a soft cloth measuring tape from a drawer—Sarah's idea of a joke, apparently. Grace holds one end at the base while Sarah stretches it along the top, pressing the head gently to get the full length. The tape is cool satin against my burning skin.

"Eight and a quarter inches," Sarah announces, voice thick. "And such lovely girth." She wraps the tape around the thickest part, fingers brushing sensitive skin. "Almost six inches around. Very respectable."

Grace licks her lips. "More than respectable. Delicious."

The word sends a jolt straight to my cock, making it twitch in their hands. Sarah notices and smiles wickedly. She sinks slowly to her knees, robe falling open to reveal full, heavy breasts with dark rosy nipples already hard. She leans in, breath ghosting over my tip, then her tongue flicks out—hot, wet, tasting the salty bead of precum.

I groan, hands gripping the counter. She takes me deeper, lips stretching around my girth, cheeks hollowing as she sucks. The wet sounds fill the kitchen—slow, obscene slurps as she bobs, taking more each time until I feel the back of her throat. Grace watches, one hand slipping inside her own nightgown to touch herself, soft moans escaping her lips.

After minutes of exquisite torture, Sarah pulls off with a wet pop, strings of saliva connecting her lips to my glistening cock. "Your turn, Mama," she says, voice husky.

Grace doesn't hesitate. She kneels beside her daughter, silver hair falling forward as she takes me into her mouth. Her technique is different—slower, more experienced, tongue swirling in lazy circles while she hums, the vibration shooting straight to my balls. Sarah stands, letting her robe fall completely open, and guides my hand between her thighs. She's soaking—hot, slick folds parting easily for my fingers. I slide two inside her, feeling her clench greedily, and she gasps against my neck.

Grace pulls back, lips shiny. "I need more than a taste." She stands, hikes up her nightgown, revealing she's wearing nothing underneath. Her pussy is neatly trimmed silver, lips swollen and glistening. She turns, bending over the island beside me, presenting herself.

Sarah guides me behind her mother. I grip Grace's hips—soft, pliant flesh—and slide my cock along her wet slit, coating myself in her abundant arousal. She pushes back impatiently, and I sink in slowly, inch by inch. She's impossibly tight for her age, velvety walls gripping me like a fist. The heat is searing; the scent of her arousal thick and musky.

I start to thrust—slow, deep strokes that make her moan with each impact. Sarah watches, fingers working her own clit furiously, then moves to stand in front of her mother. Grace buries her face between Sarah's thighs, licking eagerly while I fuck her from behind. The sight is filthy and perfect: mother eating daughter while daughter's future son-in-law pounds her relentlessly.

Sarah comes first—back arching, thighs trembling around her mother's head, a low cry muffled against Grace's mouth when they kiss, sharing the taste. The clench of Grace's pussy as she follows—walls fluttering wildly around my cock—nearly undoes me.

I pull out just in time, stroking myself as both women turn and kneel. Sarah takes the head into her mouth again, sucking hard, while Grace licks and sucks my balls. The dual sensation—wet heat and gentle suction—sends me over. I come hard, thick ropes painting Sarah's tongue, dripping down her chin onto Grace's waiting mouth below. They share it greedily, kissing deeply, tongues swirling my cum between them.

We stay there panting for long minutes, bodies glistening with sweat, the kitchen smelling of sex and whiskey. Sarah finally stands, tying her robe loosely. "You'll do very nicely for our Emily," she says, voice satisfied.

Grace pats my spent cock affectionately. "More than nicely. Welcome to the family, dear."

I pull up my pants with shaking hands, guilt and exhilaration warring inside me. Upstairs, Emily sleeps peacefully, unaware that her family's final approval was sealed in the most taboo way possible.

And when I propose next week, I know they'll both say yes.

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