Let mommy take care of you, Isobel murmured, her voice a husky whisper as her hand slid from his spent cock to the curve of his ass, fingers digging in with a possessive hunger that belied the tenderness in her eyes. She felt the warmth of his skin under her palm, smooth and yielding, a canvas for her desires that stirred deep within, blending her nurturing instincts with an urge to command. Billy stirred in her lap, his body still humming from the afterglow, but as her fingers traced the cleft between his cheeks, she sensed his uncertainty, the way his breath hitched and his muscles tensed. She leaned closer, her breasts pressing against his back, the damp fabric of her blouse clinging to her skin, and she could smell the faint musk of their shared release lingering in the air, a reminder of the intimacy they'd just shared.

As her touch grew more insistent, circling the tight ring of his entrance, Billy shifted uncomfortably, his cock twitching in a futile attempt to stir back to life. He was trying, she could tell, his hips giving a subtle grind against her thigh, but it remained soft, nestled innocently against his thigh, unresponsive to the lingering heat between them. Isobel smiled softly, her free hand brushing through his hair in a soothing gesture, even as her other hand worked with deliberate pressure, massaging the sensitive skin around his hole. "Shh, my sweet boy, your little penis doesn't need to do anything right now," she said, her tone laced with reassurance and a hint of dominance that made his cheeks flush deeper. Reaching over to the bedside table, she pulled out the strapon harness from its discreet drawer, the smooth silicone phallus gleaming in the lamplight, cool and unyielding in her grasp. "Mommy's got just what you need," she added, fastening it around her hips with practiced ease, the straps hugging her curves and positioning the toy perfectly, a extension of her own desire.

Billy's eyes widened at the sight, a mix of apprehension and excitement flickering across his face, but Isobel was quick to calm him, her maternal energy flowing through her touch as she applied a generous amount of lube to her fingers and the toy. She eased him onto his stomach, pillows propped under his hips to cradle him comfortably, and began with gentle circles around his anus, the slick gel warming under her fingertips as she worked it in. "Breathe and relax, Billy," she whispered, her voice a soft command that cut through his tension, her free hand rubbing slow, soothing patterns along his lower back. The room filled with the quiet sounds of their breathing and the subtle squelch of lube, the scent of it mingling with the earthy aroma of their bodies. She felt him yield bit by bit, his body responding to her care, and as she delved deeper, her finger slipping inside with careful precision, she savored the way his inner walls clenched and released, hot and inviting around her.

Sensing his growing relaxation, Isobel leaned down, her breath hot against his skin as she parted his cheeks further and pressed her lips to his entrance, delivering a sensual rimjob that made him gasp. Her tongue flicked out, teasing the sensitive ring with slow, languid strokes, tasting the faint saltiness of sweat and lube, her hands holding his hips steady as she explored him. Billy moaned into the pillow, his body arching instinctively, the vibrations of his voice traveling through her as she continued the massage, her fingers joining her mouth to work in tandem, stretching and soothing him with increasing depth. The act was intimate, almost worshipful, her own arousal building as she felt the heat radiating from his core, her pussy throbbing with unmet need, the strapon pressing against her mound and heightening her own sensations. She poured her emotions into it, a blend of dominance and devotion, wanting to draw out his hidden cravings and make him feel utterly safe in her control.

When she finally positioned herself behind him, the tip of the strapon nudging at his prepared entrance, Isobel moved with agonizing slowness, inching inside as she whispered encouragements. "That's it, baby, just like that," she breathed, feeling the resistance give way, his body enveloping the toy in a tight, velvety grip that sent shivers through her own core. Billy nodded silently, burying his face deeper into the pillow, his breaths coming in ragged bursts as she filled him, the initial stretch giving way to a profound fullness that made him whimper. She started slow, rocking her hips in gentle thrusts, building a rhythm that allowed him to adjust, her hands roaming his sides and back, tracing the lines of his muscles as they tensed and relaxed. The connection between them deepened with every movement, her maternal instincts fueling the intensity, turning the act into a dance of power and pleasure that left her breathless.

As she picked up the pace, her thrusts growing more forceful, Isobel reached around his waist, her hand finding his cock once more—now miraculously hard, pulsing with renewed life against her palm. She laughed softly, a teasing sound that echoed in the dim room, her fingers wrapping around his shaft and stroking in time with her movements, the slickness of leftover lube making each pull effortless. "This little man down here sure is honest, isn't he?" she whispered into his ear, her voice dripping with playful dominance, her breath hot against his skin as she leaned in closer. Billy's response was a muffled groan, his body surrendering fully now, hips pushing back to meet her drives as she ramped up the speed, the strapon plunging deep and fast, the slap of flesh against flesh filling the air. The intensity built like a storm, her own pleasure mounting from the pressure against her clit with every thrust, their shared rhythm a symphony of gasps and moans, until she went all out, driving them both toward a shattering release that blurred the lines between care and conquest.

As the storm of their shared ecstasy peaked, Isobel's hips slammed forward with unbridled force, the strapon driving deep into Billy's yielding body, each thrust sending shockwaves through them both that made her breath catch in her throat. Billy's moans escalated into high, keening cries that sounded almost girlish, his voice breaking with vulnerability as he surrendered completely to the overwhelming sensations, his body trembling beneath her. "Good boy," she purred, her tone a mix of praise and dominance, her own arousal spiking to a feverish height that made her pulse throb; she shifted her position, rising up on her knees to mount him more fully, her weight pressing down as she bent her legs for deeper penetration, the toy plunging even further into his core.

The intensity pushed Billy over the edge without a single touch to his cock, his body convulsing as he came hands-free, ropes of hot cum spurting out in rhythmic pulses that painted the sheets below. Isobel quickly slid her hand beneath his shaft, cupping the warm, sticky essence as it flowed like an open faucet, her fingers slick with his release. "Let it all out for Mommy," she encouraged, her voice husky with desire, feeling the heat and pulse of his climax against her palm; she savored the moment, bringing her hand to her lips and licking his cum clean, the salty, musky taste igniting a deep thrill within her—she loved it, the raw essence of his surrender making her own pussy clench with unfulfilled need. Billy collapsed fully, spent and utterly fucked silly, his limbs limp and his breaths coming in shallow gasps as he murmured a faint "Thanks" before drifting into exhausted sleep, his face buried in the pillow.

Isobel gently eased out of him, the strapon glistening as she unfastened it and set it aside, her body still humming with residual arousal. She dressed quickly, smoothing her blouse over her curves and adjusting her skirt, the scent of their encounter clinging to her skin like a secret. As she slipped out the door into the cool night air, she nearly bumped into a woman standing in the hallway—Billy's mother, her eyes weary but grateful. "Thank you so much for this," the woman said, her voice thick with emotion. "He hasn't been himself lately." Isobel smiled warmly, the maternal bond still echoing in her chest, and replied, "It was my pleasure, as a mother," before continuing on her way, the night's events leaving her with a profound sense of fulfillment that blurred the lines between duty and desire.

Helena's First Day