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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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She understood and agreed with his measured approach, it was something no guy had ever suggested and she immediately knew that this was what a mature guy would recommend. She was thankful that he wasn’t dismissive of the very obvious mutual physical attraction that existed between the two

‘I completely respect and appreciate that and am in total agreement. Leah and I have some plans for the next few days anyway so I will pour myself into that. And, I, obviously would love to take you up on going out in public, but I will let you lead the way and timing there. Thank you for your openness and honesty, guys my age are anything but that, so it means more to me than you realize’
 
A few days passed in a gentle rhythm. Adrian noticed how Michelle and Leah spent long mornings exploring the nearby trails and afternoons lingering over coffee or helping in the garden. From time to time, he caught glimpses of them laughing together, their bond deepening in ways that reassured him of Michelle's sincerity. He busied himself with household tasks - tending to the vegetable beds, repairing a loose board on the deck, preparing simple meals - while allowing the two friends to fill their days in the way he'd suggested.

Each evening, he'd check in with Leah: she reported that Michelle seemed happier, more relaxed than he'd seen her in a long while. Adrian felt relief in knowing the time apart from their usual routines had been restorative for Michelle, and that Leah's friendship offered genuine support.

On the day Michelle was set to leave, Adrian prepared a light breakfast and made sure the car was ready should she need a ride. When the moment came, he found her gathering her things in the foyer. He remained composed, offering a warm smile as he approached.

"Before you head out," he began, voice steady, "I'd like to ensure we can arrange that outing in the city when the time feels right. Would you mind sharing your number? That way, I can contact you directly to plan something public and relaxed, at your convenience." He met her eyes with sincere intention. "No pressure on timing - just so we can coordinate when schedules align."

He paused, folding his hands lightly. "Thank you for investing these days with Leah. It's been good to see you both so connected." He leaned slightly closer, respectful of the boundary but open in his expression. "Safe travels back."

After she slipped her contact info into his phone, he gave a nod of gratitude. "I'll send you a message later in the week with some options. Take care of yourself until then." As she departed, Adrian watched thoughtfully, mindful of the balance they'd struck: honouring boundaries, yet allowing a door to remain open for what might come in time.​
 
Michelle was rested and her mind restored from the time spent with Leah. She was able to completely clear her mind of things from home and bring light back to the parts that should matter more - connections, friendships, confidence in herself and clarity of purpose.

As she head out she gave Adrian her number and thanked him for having her and for suggesting she spend more time with Leah. She knew he was right but there was also a lingering feeling that even though he asked for her number there was a chance she might not hear from him. She brushed the pessimistic thoughts aside and told him how nice it was to spend time with him as well and for him allowing her to express herself to him about her feelings without making her uncomfortable.

She hugged him and Leah as she headed out. She had scheduled an Uber as Leah was not heading back at this time.
 
Adrian sat in the corner of the hotel's business lounge, a stack of proposals spread before him. His morning meetings had run smoothly, but his mind wandered back to the lake and the promise he'd made. He closed his laptop for a moment, reached for his phone, and paused, considering the right wording.

He tapped out a message slowly, mindful of tone and clarity - Good evening, Michelle. I hope your week has been good. I'm in the city today on business and would like to invite you to dinner tonight at 7:30. I've chosen a quiet bistro where we can talk comfortably in public. No pressure—only if it suits your schedule. If not, I completely understand. Let me know what works for you.

He read it over twice, then hit send. A small wave of anticipation followed, tempered by responsibility: he reminded himself this was a chance to explore their connection in neutral ground, far from the home and lake. He set the phone aside and reopened his laptop, diving into client briefs, though his thoughts flicked back to the message he'd sent.

Later, during a break between meetings, he checked his calendar and scrolled through nearby restaurant reviews to confirm his choice. He selected a well-reviewed bistro known for its calm ambiance and tasteful menu—appropriate for a respectful, mature encounter. He bookmarked the address and made a note to arrive early, ensuring a smooth start.​
 
Michelle’s heart skipped a beat when she received Adrian’s text. She wasn’t sure if he would actually reach out so she was incredibly excited when he did. She quickly and eagerly replied

‘Hey! That sounds wonderful and my schedule lines up perfectly for that. I’ve never been there before so let me know what kind of attire it calls for and I will be ready. I am super excited to see you’

She sent it, feeling perhaps a bit too excited in how she responded but it was genuine excitement. This was an invite for us to see if any of those conversations from the lake house were real or if it was just a proximity thing, at least for him. She knew how into him she was…in several ways
 
Adrian glanced at his phone after reading Michelle's enthusiastic reply. He paused briefly to choose his words carefully, then typed back:
"Smart casual is perfect. Looking forward to seeing you at 7:30." He added a polite smile emoji and hit send.

He set the phone aside and checked his appearance in the hotel room mirror: a crisp, well-fitted polo and tailored chinos. Satisfied, he gathered his lightweight jacket and walked toward the lobby. During the short ride to the restaurant, he reviewed the evening's plan in his mind - selecting a table in a quiet corner, ensuring the setting would be relaxed yet public.

Arriving early, Adrian stepped out of the car and scanned the façade of the bistro. The warm glow from inside promised an inviting atmosphere. He secured his jacket over his arm and approached the entrance, pausing to smooth his shirt. He offered a polite nod to the hostess and indicated he was waiting for someone. Standing just inside the foyer, Adrian folded his arms loosely, attentive to the surroundings: muted conversations, soft lighting, and a gentle hum of activity. He took a steadying breath, recalling the lakehouse conversations - how honest and unexpected they'd been. He reminded himself to remain composed, respectful, and present in this new context away from familiar settings.

He checked his watch: a few minutes before 7:30. He allowed himself a moment to note how the environment felt different from the lakeside hush - here, life moved in gentle bustle, offering them the privacy of public space. He leaned against the wall, arms relaxed, eyes occasionally drifting toward the doorway.

As he waited, he reviewed what he might say: ask about her week since leaving the lake, share a light anecdote from his city meetings, and listen attentively to her responses. He aimed to balance warmth with propriety, aware of the boundary they both respected. With each passing moment, his anticipation settled into a steady calm: he was ready to greet her politely and see where this careful, mature invitation might lead.​
 
Michelle finished getting ready by slipping on a pair of black panties and then stepping into her matching black dress, it was more a casual and summer dress style, her breasts were left exposed under the dress with no bra on. She took one last look in the mirror and then headed to her

Arriving at the restaurant a few minutes before 7:30 she felt her heart rate quicken, a sudden rush of nervous excitement had built on the drive and was at its peak in the moment. She took a few deep breaths before heading inside. Seeing Adrian waiting for her only confirmed her attraction, he looked mature, his strong body very easy to notice through his top and his tailored pants fit his frame perfectly

Greeting him with a nervous smile, ‘hey! I hope you havent been waiting long?’ she said as she leaned in for a welcoming hug
 
Adrian stood as Michelle arrived, offering a warm smile. He stepped forward and placed a gentle kiss on her cheek. "Good evening," he said, voice low and sincere. With one hand lightly at the small of her back, he guided her to their table, conscious of the subtle electricity between them. Once seated, he settled into his chair and lifted his gaze to her. "That dress is stunning on you", he commented, watching her reaction but keeping his tone composed. He gestured for the server and placed their orders, choosing dishes he'd thought she might enjoy.

When the food arrived, Adrian raised his glass in a brief toast. "To a pleasant evening," he said, then set the glass down and leaned slightly forward. "How has your week been? I've found myself thinking about our conversations by the lake and wondering how things settled once you returned home." His voice conveyed genuine interest, inviting her to share without pressure.

As she spoke, he nodded and offered gentle affirmations. Taking a sip of wine, he added, "It's been good to reconnect like this, isn't it? There's something rare about our conversations - honest and unhurried. I appreciate that." He paused, letting the moment linger before steering forward. "Have you had any moments where you surprised yourself this week? New insights or experiences that stood out?"​
 
‘You look amazing too’ she offered after his compliment

‘Admittedly I haven’t stopped thinking about you since I left. Probably a bit creepy to say but just being honest’ she said with a nervous giggle

‘But my week has been good, work has been nice to get back to. How about you? How have you been?’ she asked and he responded in kind

The conversation was flowing effortlessly which was not surprising but very welcome. A huge turn on for Michelle was good conversation, so this was stirring some feelings in her that she was trying her best to hide

‘It really is nice to connect like this. I haven’t felt an immediate attraction and connection to someone like this ever. And the fact that it’s with my friends older dad, admittedly adds to the excitement of it all, even if a little unusual’

She continued ‘I have noticed this week I feel a lot more confident, I think opening up the way I did with you showed me that while it is nerve wracking, it is empowering and gave me a big boost of self esteem, if that makes sense at all?’
 
Adrian smiled, inclining his head as he absorbed her compliment. He let a brief silence settle before responding. "Thank you. And I'll admit, you've crossed my mind often as well," he said, voice steady yet earnest. "Not creepy - honesty is valuable, especially between us." He took a measured sip of his wine, gathering his thoughts.

He shifted in his seat, settling into the comfortable flow of conversation. "Work's been productive," he continued, offering a glimpse of his week: meetings went well, but he found himself reflecting on our talks more than usual. "The city often feels frenetic, yet I've discovered calm in thinking back to moments like tonight." He paused, eyes meeting hers - an acknowledgment of their shared experience.

Noticing the ease of their exchange, he leaned forward slightly. "It's rare to connect so naturally," he observed. "I feel that too. The immediacy of our rapport is unexpected, but genuine." He allowed a knowing smile. "The unusual nature of it - yes, I'm aware. But authenticity matters more than convention in my view."

He placed his glass down gently. "I'm glad opening up gave you confidence. That took courage, and it shows strength. Feeling empowered by honesty is something I respect deeply." He paused to let the sentiment register. "It's important we acknowledge the complexity yet honor what feels real."

Adrian glanced at the surroundings - the soft lighting, the gentle murmur of other diners - then refocused on her. "I value this evening. It's helping me understand what I want and how to proceed thoughtfully. Whatever unfolds, I believe we owe it to ourselves to be sincere and considerate." He reached for his water, maintaining a composed posture.

Adrian glanced around the bistro as the check arrived, reluctant to let the evening end. He folded the bill and slipped it into his wallet, then leaned forward, lowering his voice. "There's a speakeasy just down the street - quiet, intimate. Would you care to continue there? A chance to sit a bit closer in a dimmer light." He offered a tentative smile, aware of the delicate balance they maintained.

He rose smoothly, straightening his polo. He extended his arm politely, a gesture meant to convey both respect and invitation. As he led the way out, he thought of the soft ambiance awaiting them: low lighting, plush seating, jazz murmuring in the background. He imagined the subtle proximity that might reveal more about their connection. Walking down the street, Adrian maintained a composed gait, though his pulse quickened at the prospect. He reminded himself that this was still a public setting - appropriate yet charged. Arriving at the unmarked door, he produced the password with a quiet nod to the doorman, then guided them inside. The warm hush enveloped him: velvet walls, muted lamps, the faint clink of glassware.

He guided them to a small corner table bathed in the soft glow of muted lamps. Once seated, Adrian shifted his chair slightly so it faced hers more directly, legs uncrossed and feet planted firmly yet relaxed. His posture was open: shoulders back, arms resting casually on the table with palms visible, signalling ease and invitation.

He caught the bartender's attention and ordered two cocktails, then turned back with a warm smile. As the drinks arrived, he lifted his glass in a soft toast. "To an evening that keeps revealing itself," he said, his tone inviting. When he set the glass down, he leaned forward just enough that his gaze met her eyes, conveying genuine focus.

Adrian gently gestured with an open hand toward the seat next to him. "Feel free to scoot closer if you like," he offered, voice low but steady. The motion was natural - not demanding, but clearly welcoming her company at his side. He leaned in slightly, elbows resting on the table, creating an intimate yet respectful space between them.

He maintained relaxed eye contact, letting the silence hang comfortably before speaking again. "I appreciate you coming along," he said, pausing to let the words resonate. He tilted his head in a quiet, encouraging nod. "It's rare to find someone you connect with so effortlessly." His smile softened as he observed her reaction, posture still open, inviting.

Throughout the conversation, Adrian's body language remained intentionally inclusive: when he talked, he faced her fully; when he listened, he gave gentle affirmations with a nod, hands occasionally sweeping toward her as he referenced shared moments. He lightly draped one arm along the back of his chair, subtly creating space for her to draw nearer if she wished.

In that intimate speakeasy setting, his open stance and measured gestures made it clear he welcomed her closeness - testing the waters of their budding relationship with thoughtful warmth and poised invitation.​
 
Michelle, not a drinker, asked for an ice water as the waitress at the speak easy took their orders

Her legs crossed, causing her dress to rise up a bit to give a view of her upper leg. She didn’t try to adjust it, she was fine if he wanted to look, in fact, she was hoping he would

The intimacy of the setting was not lost on her, the eye contact was intense, the attraction between them was undeniable

‘Thank you so much for dinner and for taking me here, it is so nice to spend more time with you. Would it be a bit much of me if I said I hope the evening doesn’t end here?’

She may have been feeling the moment a bit too much, but there was a yearning inside of her that she needed to let out, even if in subtle ways
 
Adrian leaned forward in the low light, noting how her dress had subtly ridden up her thigh when she shifted. He offered a slow, deliberate smile as he met her gaze. "I was hoping you felt that way," he said softly, his tone both warm and charged. "This evening feels too rare to end abruptly."

He gently rested his hand on her bare leg, fingertips brushing lightly against her skin. The contact was casual yet deliberate - an invitation to share the moment more closely. "You look incredible tonight," he murmured, keeping his voice steady even as his pulse quickened. "I can't deny how much I've wanted to be near you again since our last conversation."

He shifted so his chair was angled toward hers, open and inviting. "There's something about this space—dim light, quiet music—that makes it easy to be honest. I value that honesty with you." Adrian's gaze flicked to the glass in front of him, then back to where she sat. "If you're comfortable, I'd like to stay a bit longer. Maybe walk you home afterward." He brushed a fingertip along the back of his hand against her thigh, then withdrew his hand slightly, watching for her response in the intensity of her eyes. "I know the risk in wanting this - I'm keenly aware - but I also know how genuine this connection feels."

He offered a reassuring smile, voice dropping to a private timbre. "We can go as far or as slowly as you wish. But I want you to know exactly how drawn I am to you - body and mind. And if staying here a while longer lets us explore that safely, I'd welcome every minute." With that, he leaned back slightly, hand still resting near her.​
 
Feeling his hand against her bare skin sent an electric shutter throughout her body. The touch awakened every part of her, she felt the blood rush to the most sensitive parts of her body and they began pulsing in anticipation

She touched his hand momentarily rested on her leg ‘you have no idea how bad I want you Adrian’ she said in a moment of extreme vulnerability and directness ‘I want to explore any and everything you want to, what I am feeling throughout my body right now is something I’ve never felt. And if you can make me feel that way simply from a touch of my leg and a look in my eyes I can only imagine what anything else would feel like’

She had never spoken to a man like this before, she was being raw, open and direct. His closeness was doing something to her….and she needed more
 
Adrian heard her words, but his mind had trouble computing their very direct nature. Despite their significant age difference, it was clear that they were very attracted to each other. And now it had been communicated. He didn't expect the night to take this turn, and certainly not as early as it had since their time at the lakehouse.

"Michelle, I will guide you in any way that feels comfortable to you. Say the word and let's leave".

Blood rushed to his groin, with such a ferocity that he hadn't felt in over ten years. He had doubts about his ability to perform as he got older and remained alone. But having this gorgeous, young woman sitting beside him in a very revealing dress removed all of those doubts.
 
‘I need you to show me what it’s like to be with a real man…’ she said directly

The words were blunt and honest, she felt the vibe between them and felt she was reading it correctly. She wanted him, she needed to be taken by a real man, she had never gotten off with a guy and she already felt like she was going to cum, simply from talking to him
 
Adrian remained composed as she spoke, his expression steady and attentive. He listened not just to her words, but to the emotions woven between them - the quiet tremble of vulnerability, the weight of something deeply personal. It was clear to him that she was revealing a part of herself she had long kept hidden. There was a raw honesty in her voice, unfiltered and sincere, unlike anything he had heard from her before. Her eyes, however, spoke even louder. In their depths lay a truth too profound for language, a silent confession that words could never fully capture.

They finished their drinks not long after, the conversation slowing into a comfortable silence. With a subtle gesture, he stood and offered a hand to her. She took it, and he led them toward the exit, the city's evening air wrapping gently around them as they stepped outside. "My hotel is just around the corner," he said, his voice low and measured. There was a suggestion in his words, an unmistakable invitation - yet it was carefully framed with space for refusal. It wasn't a demand, nor even a strong persuasion, but an opening. He met her eyes, giving her a moment to respond, to turn away if she wished. He believed she wouldn't,felt confident in the connection they had built, but he knew that her choice mattered above all else. Consent wasn't just important; it was everything.​
 
As they got up her heart began beating even faster than it already was. Something was happening, she not only wanted it, she needed it. It didn’t mean she wasn’t nervous, she was terrified, about her inexperience, about how she would be to him, what she would say, how she would react…but she needed to experience this

His words needed no response, a simple nod of her head was enough to let him know that she was his from that point forward
 
A simple nod was all the confirmation he needed. Without a word, he turned and began walking, guiding her gently down the quiet street. The silence between them wasn't awkward - it was purposeful, filled with an unspoken understanding. Their steps fell into rhythm, the night air cool and still as they made their way to his hotel, a sleek, modern high-rise just a few blocks away.

Within five minutes, they had arrived. He led her through the grand lobby with quiet confidence, exchanging a polite nod with the doorman before heading toward a private elevator reserved exclusively for guests on the suite level. Years of disciplined service in the Navy, followed by a successful career in high-level consulting, had afforded him a certain lifestyle - one that included top-tier accommodations wherever he travelled.

The elevator glided upward in smooth silence. When they reached his floor, he stepped out and walked her down the plush, softly lit hallway. Stopping at a polished oak door, he pulled out his key card with practiced ease and opened it without hesitation. The door swung inward, revealing a spacious, elegantly furnished suite. He stepped aside to let her enter first, offering a quiet gesture of welcome. Then, with a brief but courteous smile, he excused himself and disappeared into the bathroom, leaving her alone to take in the space.​
 
The environment was perfect. Clean, very modern yet with touches of timelessness to it. As he stepped into the bathroom Michelle looked around, making her way to the large floor to ceiling window wall overlooking the bustling street below. People could see, she thought to herself in a playful way, that was exciting to her for some reason

She set her purse down on a table and stared out of the window, anticipating what was to come, still nervous, but incredibly excited
 
Adrian returned from the bathroom after only a few minutes, the scent of his cologne now freshly lingering in the air, subtle but unmistakable. His breath was minty, and there was a quiet confidence in the way he moved toward her - slow, deliberate, as though savouring the moment. He stepped behind Michelle and gently placed his hands on her shoulders, his touch warm and steady. His fingers began to knead the tension from her muscles with a deliberate, languid rhythm, a silent expression of care and intimacy. After a moment, he turned her to face him, his eyes holding hers with quiet intensity.

"You are incredibly beautiful, Michelle," he said, his voice low and sincere. "And I can't believe how lucky I am to be here with you."

Then, without hesitation, he leaned in and kissed her. It began softly, a tender brush of lips that spoke of affection and admiration. But soon the kiss deepened, infused with growing passion. His hands traced the elegant lines of her figure, reverent and unhurried, exploring her curves as though memorizing them by touch. He trailed kisses along her jawline, then down the column of her neck, his lips brushing her skin with featherlight pressure. Occasionally, he nipped playfully, eliciting small shivers in response. His fingers found the delicate straps of her dress resting on her shoulders, and with careful precision, he began to ease them down.

All the while, his mouth stayed close, his kisses unbroken even as the fabric slid lower. He controlled the pace, slow and deliberate, as if drawing out every second. The dress descended inch by inch until, finally, it slipped from her form and pooled silently at her feet. He took a small step back, just enough to take her in fully. His eyes moved over her with awe and appreciation, as though seeing her for the first time - utterly captivated.​
 
As he turned her around, her back against the window, it was happening how and where she was hoping it would the moment she entered the room

As his mouth found hers she let out a soft, yet intentional moan, letting him know this is what she needed. The kiss deepened with her tongue playfully entangled with his before he moved down her neck

Her breath and light moans quickened as he slipped the straps off of her shoulders. Her heavy and visibly excited breasts came into view for him. Her large areolas surrounding nipples that were very much at attention from his kisses. A hand moved to the back of his head as he kissed down her neck
 
He paused, heart quickening, as his gaze roamed over her almost bare body - only a slender strip of black lace hugging her hips, leaving little to the imagination. Her skin glowed softly in the low light, taut and inviting, and his eyes were irresistibly drawn to the swell of her breasts, where her nipples stood firm with need. He inhaled, savouring the faint scent of her arousal, then leaned in with deliberate calm. Pressing his lips to one hardened peak, he tasted her, drawing her nipple between his teeth just enough to elicit a sharper intake of breath, then traced slow, languid circles with his tongue. Meanwhile, his free hand found its way to the opposite breast, kneading it with tender insistence, rolling the engorged nipple between finger and thumb as he felt her body respond beneath his touch.

After a few moments, he shifted, trading sides to ensure each mound received equal attention. The room was filled with her soft, rhythmic moans and the subtle rustle of skin against sheets, and each sound affirmed the power he held to kindle her pleasure. He studied her expression - flushed cheeks, half-closed eyes, lips parted in rapture - and felt a surge of astonished satisfaction: that someone so much younger, so vibrantly alive, could surrender so completely to the sensations he provoked. He allowed himself a private thrill at this realization, relishing the intimacy of their connection and the exquisite vulnerability she displayed. In that shared space of trust and want, he continued to explore, determined to coax every shudder and sigh from her trembling body.​
 
As he found her breasts with his mouth she felt an electric pulse surge through her body and she moaned, loudly

Her stomach began convulsing rhythmically in response to the sensation ‘mmm, I’m going to cum’ she said softly at first. Surprised by how quickly her body was reacting. She felt her knees weaken a little bit so she leaned back against the glass window and placed her hands on his shoulders to steady herself as her body continued pulsing…
 
Adrian's breath caught in his throat as Michelle's soft confession hung in the air: she was about to come already. He could scarcely believe it. He had been an attentive, passionate lover to Claire until her illness fifteen years ago, but since then, he hadn't shared that kind of intimacy with anyone. The realization that something as simple as gently sucking on Michelle's nipples could send her spiralling toward orgasm stirred a potent mix of pride, desire, and a sudden rush of youthful confidence deep within him.

He eased away from her, guiding her gently toward the bed with steady hands. Each movement felt charged: the way her skin warmed under his touch, the slight tremble in her hips as anticipation coiled between them. As she settled onto the mattress and arched her back, he slid his fingers beneath the waistband of her panties, removing them in one fluid motion. The evidence of her arousal was undeniable - her lips glistening, her breathing shallow - and it only inflamed his desire further. When he saw her neatly trimmed pubic hair framing her already damp folds, his pulse quickened; the sight was almost overwhelming.

Standing above her, he began to peel away his own clothes with deliberate slowness, relishing the moment when he too would be bare. At fifty-four, his body still bore the disciplined lines of his Navy days: defined shoulders, a strong chest, and a core that had never truly forgotten its rigorous routines. Even as his erection remained soft in the initial moments, it looked impressively full, promising more with each heartbeat. He paused briefly to drink in the scene - Michelle spread out before him, her eyes dark with need, and himself reborn in this shared intimacy.​
 
Watching intently as he undressed himself standing in front of him. Her pussy now feeling the cool air of the room around its wetness was a vivid sensation. Her hands found her breasts as he slowly undressed

Her eyes told the story of how hungry she was for him and how much she loved his body. As he slipped his pants and boxer briefs off though her facial expression changed dramatically. It was that of disbelief, almost startled by the sheer magnitude of his size her eyes opened widely as did her mouth

‘Holy crap Adrian!’ she said in a shocked tone ‘you are freaking huge!’ she added in disbelief, eyes moving back and forth between the huge and heavy cock hanging atop his loose massive balls, reaching well past the middle of his thigh
 
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