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My Best Friend's Dad (AJS Roleplaying x intelligenceseeker)

AJS Roleplaying

Returning veteran
Joined
May 24, 2025
Location
The Emerald Isle

My Best Friend's Dad
A Roleplay Brought to You By:




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Adrian Whitaker
written by AJS Roleplaying




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Michelle
written by intelligenceseeker

 
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Adrian's lips curved into a slow, knowing smile as he watched the surprise flicker in her eyes. That small reaction only served to bolster his confidence, the air between them charged with a quiet but insistent tension. He shifted closer, closing the gap until he could feel the warmth radiating from her. His gaze lingered on her expression - equal parts curiosity and desire - before he allowed his voice to drop to a low, inviting cadence.

Every subtle movement felt deliberate: the gentle rise and fall of his chest, the faint brush of breath against her skin. He took another measured step, their proximity heightening her awareness of his presence. Her pulse fluttered; she was clearly caught between hesitation and intrigue. He held her gaze, steady and unhurried, as if giving her permission to lean in or pull away, entirely at her discretion.

Finally, with a soft exhale that seemed to echo the unspoken promise in his eyes, he asked, "Would you like to touch it?" The question hung between them, charged with possibility - and in that moment, everything felt suspended in anticipation.​
 
When he asked her that Michelle sat up on the bed, knees now hanging over the bed and feet on the floor in front of him

Her hands reached for his chest at first and slowly ran them down before she reached his still soft, yet massive cock. Taking it in one of her hands she felt the heft of it for the first time, looking up at him ‘it’s so huge and so heavy, oh my God’ as she slowly worked her hand around it. Her other hand cupped his loose and heavy balls as well and she began to feel him hardening in her hand. As he grew it amazed her even more, an occasional upward glance to make eye contact showed her disbelief and amazement. She was nervous and almost frozen in a way, she had never been with someone so large and wasn’t sure exactly what to do, the eye contact lingered ‘I definitely was not anticipating this, holy crap!!’
 
Adrian remained still, his breath steady, as he observed her tentative curiosity. She reached out with gentle hesitation, first wrapping slender fingers around the length of him, exploring the warmth and firmness hidden beneath his clothing. He felt the subtle shift in pressure against his skin, a tremor of sensation that hinted at the excitement growing within him. Without betraying anything on his face, he allowed himself to notice how her fingertips traced along his shaft, lingering for a moment before moving lower, cupping him delicately. The faint, involuntary thrum of his pulse at the base of his spine mirrored the growing hardness he could no longer deny. Each subtle squeeze, each exploratory caress, drew a deeper response - heat pooling in his belly, a low hum of desire vibrating through his body.

When she murmured a comment about his size, a flicker of warmth spread across him, fuelling an undercurrent of anticipation. Her words, soft yet bold, awakened something primal in him: a desire not only to feel but to encourage her confidence and skill. He offered a quiet nod, an unspoken invitation for her to continue, keen to witness the extent of her daring and imagination. In that hush between breaths, they shared an intimate understanding: his restraint in expression only heightened the electric tension, while her curiosity guided the journey. As her hands ventured further, exploring contours and textures, Adrian surrendered to the silent exchange, eager to discover how her touch might deepen both their pleasures.​
 
Still making eye contact with him as she let it rest in her hand she closed her hand softly around it ‘It’s so freaking heavy’ she exclaimed as she slowly stroked up and down its flaccid but hardening length

As it became more rigid her hand was unable to fully wrap around its girth and she murmured ‘oh my God’ again as it continued to grow due to her touches. Taking her other hand now she placed it on top of her other, two full handfuls were not enough to conceal his length. His heavy balls hanging beneath she pressed his huge shaft upwards and gave his balls a gentle kiss ‘is this ok?’ she asked trying to maintain the eye contact when speaking
 
Adrian's gaze remained steady as he observed Michelle, a tranquil confidence radiating from his expression. A slow, knowing smile curved at the corners of his lips, betraying the satisfaction he felt in this moment of intimacy. Michelle's features, flushed and wide-eyed, revealed her innocence; every subtle hesitation, every tentative movement spoke of her limited experience - especially when faced with someone as assured and practiced as he was. As he gradually grew to full length, she struggled to encompass him with both hands, and he felt a quiet swell of pride at the sight: a reminder of the dynamic between them, of the power and vulnerability intertwined in their encounter. Yet Adrian's pride was tempered by respect; he was acutely aware that true intimacy demands care and consideration, not merely dominance.

He noted the way her breath hitched, the slight tremble in her fingers, and the rapid flutter of her heartbeat beneath her skin. Each sensation heightened his own awareness, compelling him to guide her gently rather than rush. He leaned closer, his voice a low murmur that carried warmth and encouragement. "That feels incredible," he said, his tone both reassuring and inviting. "Keep going at your own pace—don't hesitate to explore however you like. If you want, I can share some pointers to help you discover what feels best." His words offered permission and support, underscoring that their shared experience was built on mutual trust and the promise of deeper connection.​
 
Nodding her head in response to his words, with his cock pressed against his stomach she licked his balls gently and took one in her mouth momentarily.

Moving slightly back she let his cock slip from her grasp and as it fell it slapped her face from its heft. She smiled and giggled nervously before taking it back in her hands and kissed the head of his cock and slowly licked around the head ‘I don’t even know if this will fit’ she said somewhat seriously but with a cute smile

She ran one hand up his stomach to his chest as she then took his head in her mouth, backing off ‘oh my God, it’s for freaking huge Adrian’ she exclaimed yet again
 
Adrian leaned back slightly, a slow, appreciative smile spreading across his face as he felt her tentative movements. His soft moans of approval were meant to reassure her - to let her know that he genuinely relished each moment of this shared intimacy. Watching her gently work to accommodate his length was both humbling and intoxicating; the sight of her lips stretching to welcome him sent a fresh pulse of desire through him, solidifying his arousal even further. Despite the powerful urge rising within him to guide her more forcefully, he remained attuned to her pace, choosing patience and encouragement over haste.

He observed the subtle tension in her jaw, the way her eyelids fluttered as she found her rhythm, and he marvelled at her determination. A flush crept up his cheeks at the vulnerability she displayed - this trust she placed in him - and he felt a deep respect for her willingness to explore. He resisted any impulse to seize control abruptly; instead, he lowered his voice to a warm, steady tone, offering gentle guidance.

"Just breathe and relax," he murmured, his words smooth and reassuring. "There's absolutely no rush. Take as long as you need to adjust - let me feel you comfortably. I want every sensation to be as pleasurable for you as it is for me." He paused to watch her reaction, noting the slight curve of her lips around him and the soft catch in her breath. "If you need to stop or slow down at any point, just let me know. I'm right here with you."

By emphasizing her comfort and pleasure, Adrian fostered an atmosphere of trust. His encouragement was sincere: he intended their shared experience to be a moment of mutual enjoyment, where her confidence could blossom and both could lose themselves in the sensual exchange without pressure or expectation. As he continued to support her with gentle reassurances and careful attentiveness, their connection deepened - each breath, each movement, each soft moan weaving them closer together in this unhurried, intimate dance.​
 
His words elicited comfort, care and patience, it was not something she had ever experienced but she felt it through her body. His words alone made her moan in pleasure, feeling her pussy swell again in response to it

She took her time adjusting to his size. Managing to get a few inches past his head in her mouth but unable to go further ‘I’m sorry I cannot fit more’ she said almost embarrassingly

Feeling her body react in the way it was from her giving someone else pleasure shocked her, she felt as if she might cum simply from tasting his cock

Taking a break from his cock she lowered herself to her knees on the floor in front of him and took his balls in her mouth again, each huge in their own right. One hand reached around to press against his butt as she situated herself more comfortably beneath him. Her moans became more rhythmic, was she really going to get off from this? She was a bit embarrassed to let herself go like that thinking he might find it weird
 
Adrian's breath hitched as Michelle carefully guided the swollen length of him past her lips. A low, guttural moan escaped him, resonating with both surprise and pleasure as she took a few inches into her mouth. When Michelle pulled back, flushed and apologetic, Adrian offered a warm, encouraging smile. "You don't need to apologize," he murmured, voice husky with desire. "I love the way you're trying."

Michelle's cheeks tinged pink as she shifted onto her knees before him, a posture of trust and vulnerability that thrilled Adrian more than he could articulate. He watched her with rapt attention: the soft curve of her neck, the slight tremor in her shoulders, the intensity in her eyes as she focused on pleasuring him. Every detail felt electric - the gentle glide of her tongue, the careful rhythm she set, the way her hand cradled the base of him, guiding him deeper when she felt ready.

His reassurance seemed to bolster her confidence. She leaned in again, opening her mouth wider, welcoming him with a mixture of eagerness and tenderness. The sensation of her lips and warmth created a heady rush, each movement drawing a deeper response from him. He could sense her passion in the slight catch of her breath, the way her brow furrowed in concentration and delight. Every soft swallow, every gentle tug, every pause for her to look up at him brought a fresh surge of arousal. He offered quiet praise - "Just like that," "Yes, that feels amazing" - words meant to affirm her, to let her know how deeply he appreciated her devotion. Her pleasure in giving pleasure was clear: the slight flush climbing her neck, the way her eyes glistened with intent, even as she concentrated on the delicate balance between pressure and speed.​
 
Her body continued to writhe in pleasure beneath him, his words and gentleness and affirmation were bringing her to a place where she now knew she was going to burst into another orgasm. She decided not to fight it anymore, taking him out of her mouth she pressed her face firmly into his stomach ‘I’m going to cum, fuck’ she growled with intense pleasure. Her body pulsing and convulsing uncontrollably

Her eyes made their way back to his as her orgasm subsided ‘that’s never happened before’ she said with a renewed eagerness. She stood in front of him to kiss him deeply as she stroked his massive cock with one of her hands

‘I want to do and give you things you’ve never had before…’ she said intimately before continuing ‘tell me what you want, please’
 
Adrian leaned back slightly, a low, amused chuckle escaping him as he felt Michelle's body tremble and release around him. The intensity of her pleasure, sparked by the simple but intimate act of her oral attention, sent a ripple of satisfaction through him. When she rose from her position and looked down at him with a questioning glint in her eyes - asking what he wanted - he responded by deepening their kiss. His lips moulded to hers with deliberate slowness, and his hands roamed over the generous curves of her body, exploring the warmth and softness of her skin. He paused at her chest, fingertips grazing and lightly pinching her nipples, drawing a subtle gasp from her that only heightened the electric tension between them.

Their kiss broke only long enough for him to meet her gaze: there was no need for words. He guided her gently toward the bed, laying her down with a tenderness that contrasted with the raw heat of desire in his eyes. He placed a pillow beneath her hips, angling her body to offer himself a clearer path - an act both practical and charged with anticipation. Michelle's breath caught as she settled into the raised position, offering him access and inviting him deeper into the moment.

Adrian paused, taking a moment to drink in every detail: the flush of her cheeks, the sheen of moisture glistening at her entrance, the soft rise and fall of her chest beneath his hand. He brushed a strand of hair behind her ear and allowed his fingers to trace idle patterns along her thigh, stoking the anticipation. Then, with measured intention, he aligned himself with her wetness. He brought the head of his cock to her lips first, gently coaxing it along, making sure she was comfortably opened and fully lubricated. He watched her reaction - her eyes half-lidded, breathing shallow and eager - to confirm she was ready.

When she silently signalled her consent, arching her hips toward him, he began to push forward. The initial entrance was slow, almost reverent, as he felt the exquisite tightness envelop him. Each inch was savoured: the subtle squeeze of her walls, the soft heat that welcomed him in.​
 
The anticipation for Michelle was heightened, she had never been with someone so big before and was worried about it hurting or not fitting. But he had her so wet that it made things a bit easier

Still, the intensity of feeling her pussy be stretched to its limit was incredible. The pain was a good pain and it was a huge turn on for her. Her eyes and facial expression told the story of her pleasure and initial discomfort and the sounds she made added to it all

She was loud, louder than she ever imagined she might be but his massive size was driving it out of her
 
Adrian hadn't expected Michelle to take him so well - not with how thick and hard he was, straining with the kind of pressure that always made him doubt whether full penetration was even possible. But there she was, her body welcoming him inch by inch, her breath catching in short, shaky gasps, her eyes locked onto his with a mixture of determination and desire. It was almost surreal. The tight heat of her wrapped around him like a vice, and he had to clench his jaw just to keep himself from losing control right then and there. Every twitch of her muscles around him was a pulse of pleasure that shot through his spine. "Fuck," he muttered, voice thick with disbelief. "You're taking me so well."

He paused once he felt resistance - a point where he knew pushing further might hurt her. He wasn't fully in, and he hadn't expected to be. Physically, it just wasn't going to happen. Still, the way she gripped him, how unbelievably snug and warm she felt, was almost too much. He looked down at where their bodies met, then back at her flushed, beautiful face.

"You feel fucking incredible," he murmured, awe and heat mixing in his voice. He leaned in to kiss her, slow and deep, letting his hips remain still for a moment to give her time. His hand came up to cradle her cheek, his thumb brushing along her flushed skin. "Tell me if it's too much."

Adrian stayed there for a beat longer, letting her adjust to the fullness, his hands roaming across her sides, her waist, grounding both of them in the moment. Then, slowly, deliberately, he began to move. Long, steady strokes that had his hips rolling into hers with practiced control. He was careful at first, listening to her body, watching her reactions - how her eyes fluttered closed, how her lips parted with each slow thrust, how her hands gripped his back tighter each time he pushed in.

The sound of their bodies moving together - wet, rhythmic, heated - filled the room, along with the low growl of his breath and the occasional moan that slipped from her throat.

"Goddamn," he muttered under his breath, barely able to think straight. "You're so fucking tight."

He increased his pace just a little, testing, feeling her rise to meet him, her hips lifting, her thighs squeezing around him. The way she responded - hungry, aching for more - only made his restraint harder to maintain. He swore softly again and dipped his head to her neck, kissing and nipping along her skin as he thrust into her with slow, deep rolls of his hips.

Every movement was deliberate - sensual, intense, and full of heat. He could feel her starting to tremble beneath him, the telltale signs of pleasure building fast. Her nails dug into his back, and she moaned louder now, no longer able or willing to hold it back.

"You're doing so fucking good," he murmured against her skin, his voice rough. "Taking every inch I can give you."

He pulled back just enough to look into her eyes, catching the raw need there. It hit him hard, that look - how much she wanted him, how much she was giving. He leaned down to kiss her again, slower this time, almost reverent. And then he kept going - pressing into her over and over, his rhythm steady but intensifying, each thrust deeper, more powerful, coaxing cries of pleasure from her lips. The way her body welcomed him, clung to him, moved with him - it was all-consuming. He knew he wouldn't last much longer, not with how tight she was, how good she felt, how completely she had him unravelled. But he held on, determined to give her everything he had before he let himself go.​
 
She could feel herself tightening even harder around his cock as she knew she was about to cum again

The noises from her now were palpable, loud, rhythmic and intense

Hearing his words about how tight she felt sent her over the edge.

Her hands reached to his arms initially and squeezed before they fell and uncontrollably started reaching for the sheets to grip. Her body convulsing, hard and fast with little control over them

‘I’m cumming on your huge dick’ she screamed not concerned about how silly it may have sounded. She felt his huge balls slap against her and she gyrated uncontrollably into her first orgasm on a dick
 
Adrian could feel the unmistakable tightening around his cock, her climax blooming beneath him like a slow, electric surge. The way her body responded - rhythmic, involuntary, almost trembling - only pushed him further toward the edge. He watched her unravel, a raw and beautiful surrender that left him breathless. The sight alone might have been enough to undo him, but it was the feel of her - wet, pulsing, impossibly warm - that sent another jolt of hunger through his spine.

Each thrust now was met with a slicker glide, her orgasm making everything more intense, more desperate. His grip tightened, the pace instinctively shifting, not out of aggression but from the deep, coiling need that had been building low in his gut since the moment he'd first slid inside her.

He was close - achingly so. That familiar heat began to flood his core, a pressure swelling and relentless, curling his toes and making it hard to breathe. The pleasure was maddening, relentless, impossible to ignore. It clung to him, pulled at him, begged him to let go.

"Fuck," he growled under his breath, jaw clenched as the tension mounted. "I'm getting close…"​
 
As her orgasm finally subsided she heard his words

She slid out from under him and had him stand in front of him as she knelt on the floor in front of him.

Pressing his cock against his stomach she took his huge, loose balls in her mouth as she stroked him.

‘Will you finish on me?’ she asked shyly, almost embarrassed to ask it but wanting it so badly that she couldn’t help herself from her own vulnerability in the moment
 
Adrian could hardly trust his senses as he took in the scene before him. The sight of her on her knees, her hand wrapped tightly around the base of his cock, was almost too much to comprehend. It was the image of pure submission, raw and intimate, a silent acknowledgment of trust and lust tangled together in something that felt far more carnal than merely physical. His breath hitched as he looked down at her, completely taken by the view. There was power in her vulnerability, and it thrilled him to his core. She wasn't just kneeling in front of him - she was giving herself over, wordlessly inviting him to release everything onto her. The invitation was silent but absolute. That simple, stunning act of surrender unspooled something deep in Adrian, something that had been coiled tight inside him for far too long.

Then, with a suddenness that stole the air from his lungs, his climax overtook him. It wasn't a gentle crescendo but a ferocious eruption, wild and unrelenting. His seed shot from him in thick, hot streams, the sheer force of it making his body jolt. Spurt after spurt poured out, more than he'd thought possible - an almost obscene amount, painting her with his lust in broad, messy strokes. It splattered across her mouth, dripped from her chin, and ran down her breasts in rivulets. A few errant streaks reached her thighs, the last of it clinging to her skin like the remnants of a storm.

Adrian gasped through the last pulses of his orgasm, chest heaving, legs trembling. The room around him blurred at the edges. His cock throbbed with lingering sensitivity as the final drops leaked from him, still guided by her unwavering grip. He looked down at her - coated, glistening, utterly still - and was seized by a sudden, visceral awe. It wasn't just the physicality of the moment, though that alone would have been enough to scorch itself into his memory. It was the absolute contrast - her calm composure against the chaos of his pleasure, her quiet stillness as he came undone. She had taken everything he gave, without flinching, without looking away. The contrast of control and release was intoxicating.

Adrian stood there, overwhelmed, panting softly, heart hammering in his chest. He didn't speak. He didn't need to. There were no words that could capture the gratitude, the desire, the sheer reverence he felt for what had just passed between them. And still, she remained before him - his pleasure etched across her body, marked by him. The image of it, of her, would haunt his fantasies for weeks. Months. Maybe longer.​
 
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