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Hers For a Night

Summary:

“I can’t believe I’m doing this,” Brienne muttered as she took another sip of her dark drink, taking a moment to glance at the other patrons in her restaurant and wondering if they suspected what she was there to do.

“I’m just happy you’re finally going to get fucked the way you’ve always wanted.”

Notes:

Dedicated to winterstale24:

Your prompts challenged me and I thank you for it. I'm sorry I'm so late in posting. I hope you enjoy it! Took two of your prompts and created my first sort of threesome!

Prompt 2: Cleos Frey: Matchmaker or Smutpeddler. - Explicit sex, Jaime/Brienne/Addam, plus size heroine

A huge thank you to my Beta - You rock, you are awesome and I owe you a story :)

Work Text:

Jaime looked on as Cleos stared at the scattered papers in front of him with worry.

He knew he was old school, preferring paper over laptops. Knew he had been teased about it relentlessly by their family, even colleagues, but it hadn’t mattered to him. He had told him it made sense to him. It helped him organize his thoughts, make lists, and find matches he wouldn't be able to digitally.

And as he sat in his favorite booth, at the emptying 5-Dayne restaurant, with a large cup of coffee in hand, it didn’t look like he was finding the answer the papers usually brought.

"You look constipated, cousin." Jaime said as he took the seat across from him, tossing the white kitchen towel he carried over his shoulder. "What's wrong?"

Cleos looked up and offered him a wry smile, his face showing the struggle he had in asking people for help.

"Nothing's wrong... well, not really wrong... fully..." he stumbled.

Jaime gave his cousin time to gather his thoughts, knowing it would take him some time to tell him what he needed.

For the past three nights, Cleos had come in with his portfolio, taking his reserved spot, and mulling over "work" papers. He knew his habits, understood his method, even respected his work, but he knew he had come up against something, or someone, that was leaving him perplexed.

A perplexed Cleos was something everyone tried to avoid, especially when it came to work. It was one of the reasons Jaime had agreed to hire him. After numerous ventures and positions, his Aunt Gemma had finally asked him to hire him. After a disastrous week in the kitchen, he had moved him to the back office. It was there that his never-ending knowledge, photo memory and gentle manner had shown Jaime where he could truly employ him and excel.

And excel in it he did. Having a 100% approval rating.

"I'm having a problem... pairing... someone."

It was an issue Jaime hadn't seen from him yet.

"What's wrong with them?" Jaime asked, assuming the issue lay in the applicant and not the matcher.

Cleos shifted, visibility uncomfortable. Intrigued, Jaime pushed.

"They can't be that bad.... or difficult," he assessed.

Cleos remained quiet, frowning.

"I don't want to turn her away... but I don't think we can fulfill her requirements," he finally said as he handed Jaime a paper with the petitioner's information.

To anyone else’s eyes, the information on the paper was filled with gibberish. Words strung together in silliness. It had been a code that Cleos had created to protect everyone involved. Thankfully, it was also a code Jaime had contributed to and knew its key to decipher.

‘Crescent Moon - New Client - Relocation - Well connected - Referred - Successful - Hard Exterior - New to Spectrum - Vanilla - Limitations - Strong - Tall – Muscular.’

Her name and last few words held his attention. Could it be?

"I can't find anyone I think would be very.... receptive to her."

Jaime knew what he meant and if this was the person he thought it could be, appreciative was the correct term. Because even if she was homely at best, everything else about her was quite agreeable. His body agreed with his statement as he shifted slightly.

"I was thinking about the SellSword, but he doesn't fit her specifications and only remedies half of the problem."

His sentence finally brought him out of his thoughts.

"What specifications?"

Cleos motioned for him to continue reading the paper he had forgotten was in his hand. Once Jaime reached the bottom of the page he couldn't help but smile.

Goddess complex - Triad - Dropper

“Bronn wouldn’t be a good fit,” Jaime quickly responded.

“I didn’t think he would be,” Cleos agreed, looking defeated. “She’s being referred by The Rose. We can’t disappoint.”

“Who said we would.”

“I don’ have anyone else available that weekend. The Spear is out of the town for the next three weeks.”

Jaime cringed at the suggestion. He would have been competition.

“Leave it to me. I’ll make it happen. Put everything into play.”

“You?” his cousin asked, surprised. “But you retired.”

“Because there wasn’t anything worthwhile out there. But Tarth is.”

“You know her?” Cleos asked surprised.

“In passing. Conferences here and there,” Jaime said, not bothering with specifics. “It’s hard not to in this business.”

“I’ll have to inform her.”

“Same protocol, no names until meet day,” he warned. “She can come up with her own conclusions and decide if she wants to continue,” which he truly hoped she did.

“And who will be joining you?”

Jaime couldn’t help but smirk as he handed him back his notes.

“The Tree.”

——————————

“I can’t believe I’m doing this,” Brienne muttered as she took another sip of her dark drink, taking a moment to glance at the other patrons in her restaurant and wondering if they suspected what she was there to do.

“I’m just happy you’re finally going to get fucked the way you’ve always wanted,” her dearest and closest friend commented as she continued to peruse the dinner options on the menu.

“And you’re sure…” Brienne began for the hundredth time.

Margaery turned to look at her, setting down the oversized piece of paper on the clothed table.

“He’s discreet. No one will find out and you’ll be pleasantly matched. You don’t have anything to worry about,” she assured her. “I’ve used him several times and have always been more than satisfied.”

Brienne nodded, recalling each time she had, providing, in detail, the “adventure” she’d had over brunch the following day.

“Now, the next time we have brunch, you’ll be sharing instead,” her best friend noted with a large grin.

Taking a deep breath, Brienne wouldn’t help but smile fully, feeling a bit giddy.

She deserved this and more importantly, she wanted this.

“I’m not sure how much detail I’m going to be able to give,” her face turning red as she averted her eyes.

“Oh no, I want it all. Every graphic detail. You are not getting out of that,” Margery replied sternly.

Before Brienne could counter, the clearing of a throat brought their attention to the newest arrival at their table.

“I’m sorry to interrupt…” a soft male voice began.

Margaery turned to look at him, her pleasant mask re-appearing.

“Please join us Cleos.”

The small man nodded, offering a wry smile as he sat, putting down a large brown portfolio on the table.

“Thank you for agreeing to meet me here,” Brienne said, her voice steady and firm.

“On the contrary, it’s my pleasure. I’ve been trying to get a reservation here for a couple of months however haven’t been able to get in.”

“Well, depending on how happy you make Brienne, I’m sure she’ll have a table available for you,” Margaery teased.

Brienne shushed her, even though there was no way anyone else would be able to hear them. She had made sure to sit them in one of the semi-private booths, away from prying eyes.

“It’s a beautiful restaurant,” he continued, his voice a bit nervous, “A three star Dayne recipient.”

“Thank you,” Brienne blushed. “I received the distinction last year.”

As he settled in, Margarey looked at her watch and noted the time.

“It’s time for me to go. I promised Loras a spa day,” Margarey said as she stood. “I’ll speak to you both soon.”

And then she was gone, leaving the two to finalize the details.

“I received your signed NDA last night, thank you," Cleos began, as he opened his portfolio. "And I received the others this morning, completing that portion. This will ensure that anything that transpires now to the end of the meeting day will not be disclosed at any point without swift and severe financial penalties.”

"Have you ever had to... enforce it."

"Thankfully no. But if we had to, we would be prepared. We have the best law firm on retainer," Cleos confided. "But more importantly, our vetting process and fees keep us from needing to. As you've experienced, we do extensive research on our clients, profiles and recommendations. We do that so that every partner feels comfortable and knows they can trust us."

Brienne nodded, recognizing the work he had to do to make such a private and intimate business.

"I know there are other establishments, but we hold ourselves as the best. Our standards are set to the highest. You can see that just by the admission process. We take pride in making sure we are able know what you want and deliver on it."

She agreed... it was hard to feel understood... and to know he had been able to match her... it was more than she could have expected.

"There are some rules everyone will have to follow. This is a full participation activity that everyone must consent to. If you or they do not feel comfortable at any moment, a clear no is all that is needed to stop. There will be security detail a couple doors down should they be needed, and there will be one person listening in to make sure everything remains consensual. The room will be equipped with various stop buttons that will set off an alarm indicating you need to step back and stop. Everyone is to follow their partner's wishes, regardless of stage. Because of your particular request we always try to add additional safeguards and stipulations, for everyone's safety.”

Brienne was almost giddy with anticipation. This was happening. She was going to do what she had always wanted to and someone wanted to do it with her.

"What rules?"

"You cannot stray from your request. You've approved two entry points and they are aware. You've approved some “handling” however nothing that will require additional support," he recited, recalling all her requirements from memory.

"Correct," she nodded, unable to stop her face from heating up.

"All medical exams are clear and you are additionally protected in case of any malfunctions."

She nodded.

"You have been matched with two experienced colleagues who are enthused to meet your acquaintance. They are aware you are a level 1 and will take the time to make sure you feel comfortable."

Brienne took a deep breath, her palms becoming sweaty at the thought.

"Our policy, due to the number of people involved, is restriction of kissing during the event. It helps keep everyone.... uncontaminated."

She couldn't help but feel a bit deflated.

"Is that a non-negotiable item?"

"It will depend on your partners. However, it is also one of their own specifications”, he noted. “I can pass it on as an add on request for you if you like. Is that a non-negotiable for you?"

"No, I'd like to proceed forward even if it is not approved," she quickly responded, hiding her disappointment.

"Per policy, we also restrict alcohol consumption before and during the event. If anyone suspects inebriations, all activities will cease. Each participant must be clear-headed to give full consent. It's the foundation of our service.”

She nodded, agreeing fully.

“Good,” he proceeded on. “The conference room has been booked for the evening, up to the morning. If you would like to extend your stay in your own private room, that can be arranged, you would just need to call us.”

“I may just book that extension now,” knowing she might be sore from her activities.

“I’ll let my assistant know so we can prepare that for you,” he made a mental note. “We will arrange for breakfast to be brought up to you from ‘The Lion" restaurant in the hotel; a small token for choosing our services.”

“Unnecessary, but very appreciated.”

Cleos nodded with a small smile and continued the specifications he recited at each appointment.

“As part of the experience, we’ve taken note of your likes and will have nourishment set up in the room for the evening. Additional toiletries will also be on hand in the bathroom. Should you need anything laundered during your stay, we will take care of it.”

It was a lot of information to take in, but she was pleased to see how much thought and detail went into an appointment.

“Regarding your partners. Both are to your specifications. You matched perfectly with two of our top rated colleagues. I reviewed all your information with them, and they happily accepted. I will just need the same from you today once we go over any questions you may have about them”.

She was surprised he had found two willing participants who had met all her needs and hoped beyond hope, that one of them was who she had envisioned from months ago.

“I need to mention this to you Brienne, because I want to make sure you are aware. The select group of people that we cater to are at a certain tier that run in small circles. There may be a possibility that you know some of them or run into them in the future. Once your evening concludes, whatever transpires behind closed doors will remain there. Should you ever meet anyone outside of it, it should never be mentioned or touched upon. It’s one of the most important parts of the NDA clause. We take it quite seriously. Members come to us for their anonymity. None of our participants would want to be “outed” at any point or be made feel uncomfortable, including yourself,” He caught her eye, looking even more serious. “If you don’t believe you can do that, I am happy to close this request and return your deposit.”

She only thought about it for a moment. She wanted this. She wanted to be worshipped and cherished. To be shown what it meant to see stars and be truly well fucked. This could be it, especially with her luck in men. And if it was him for one night, it would be enough for her lifetime.

“I can do it. We can proceed,” as excitement trickled up her back.

“Good. I will need from you is your signature once we go over their requirements," Cleos continue. “BrightRoar and theTree do know each other. They have been long standing members since the start of this venture. They are highly valued and highly rated. They have done this scenario before and are quite comfortable with all that transpires.”

Brienne couldn’t help but squeeze her thighs together as she listened intently.

“They want to be clear there will be no inclination or interaction between themselves. If any sort of effort is made for them to do so, all activities will cease and they will leave,” he said, making sure to sound firm. “It’s customary for them not to spend the night once activities cease and their preference is no kissing. They enjoy vocalness and do like taking the lead, which may be best in this instance to guide you best. They are very good listeners and will be paying close attention to all your needs and concerns. They require you to always be between them any time an act is taking place together. The Tree enjoys being a spectator but also participates in full activities”.

Not even in her wildest dreams could she have envisioned this outcome.

“BrightRoar has agreed to your petition to enjoy the afterglow however the Tree has declined."

She could handle that, agreeing instantly.

“If you are in agreement with their specifications, all I will need is your signature.”

And she was in complete agreement. It would be worth every penny.

——————

He had first met her over a year ago. It hadn't been his best moment and by the end of their short acquaintance, they were more foe than friend. He could admit now that there had been an underlying pull he had felt towards but hadn't recognized it until after he was back home, still nursing a broken heart from his recent break-up. The second time they met had been a few months after, at the Dayne Culinary Conference, where they had been slotted together in various activities due to their thriving restaurants.

He hadn't been able to read her fully at the time, didn't want to make her feel uncomfortable with his attempt to flirt. Addam had always teased him about being horrible at it. If truth be told, he had rarely needed to. Women naturally gravitated towards him with little effort on his part. But Brienne hadn't. She hadn't fallen all over him, no matter the amount of charm he had used on her. There had been some lingering stares, but not enough to deduce if she wanted to know more about him past the event.

On the times they had been able to chat he had been surprised to find she liked a lot of the things he did, including house crests and post dragon history. It was how her pseudonym had caught his attention, the Crescent Moon. He hoped his own name would spark recognition in her. That she knew he would be there when she opened the door, waiting for her... choosing her.

If all he could have was one night, it would have to be enough for his lifetime.

-----------

Brienne hadn't been sure what to wear. Margaery had been little help, at first, while they ate a light dinner in her hotel suite.

"Why wear anything? It'll get you faster to the main event."

“You aren’t helping. I’m not going to walk in naked,” she argued.

“Then let’s find something in the middle.”

As they looked over options, Brienne mentally went through the list Cleos had gone over with her once more last night. Her request for kissing hadn’t been fully rejected but had also not been completely approved either. Both men had elected to decide once the meeting had begun, wanting to see how comfortable they felt with her.

She was content with their response and had finalized the transfer of two thirds of the payment into the requested account as instructed.

As crazy as she had thought Margery was for suggesting this idea at first, she was now grateful for it.

It hasn’t been easy navigating her way through a male dominated field, even more so with her features. She wasn’t blind to what people saw, wasn’t deaf to the jokes both men and women made. Her father had taught her from an early age to ignore it, ‘words are wind’, he would say. What she had done was stop letting it define her. She learned to defend herself and pave her own way. Now, one of the most successful chefs to come to Kings Landing had given her the confidence she had lacked as a teenager. But even with a new sense of worth, she seldomly dated, let alone had any earth-shattering experiences like her friends would share over brunch.

And it was after her last horrible date more than a month ago that her best friend had suggested a ‘service’. She had been skeptical at first and was surprised to find out Margaery herself currently used it and had for some years.

“BrightRoar.”

“What did you say?”

“BrightRoar,” she repeated. “Intriguing, right? Our code names per say. It’s a way to keep us as anonymous as possible. I’m the Rose.”

“And BrightRoar?” Becoming anxious to know.

“He’s the elusive white whale,” she smiled conspiratorially. “Rumored to be the best. We’ve all requested him but no one I now has been lucky enough to be paired with him. We aren’t a match for him.”

That name alone had propelled her to request a meeting with “The Matchmaker”, Cleos Frey. She had heard it once before, reciting its historical significance not too long ago. She had made sure to fill out her requirements with him in mind and in correlation with her fantasy’s. If she was going to do this, it would be based on her deepest wants. She could let the Gods do the rest.

And they had chosen to shine upon her.

In a couple of hours, she would know if it was him, and either way, would have the best night of her life.

————————

She shivered at the contrast in their touch as they lightly trailed their fingers down her bare arms, a wake of goosebumps appearing in their aftermath.

She stood between them, their warm breaths hitting the sensitive spots of her neck.

By all the Gods, how was it possible to feel this much?

When she first stepped into the dimly lit bedroom, the beauty of the half-clad men standing on either side of the large bed took her breath away. But finding his emerald eyes staring back at her had made her forget how to breathe.

Now between them, hands began to trace her body. She could hardly keep herself standing. Soft lips inches from her own, she felt his breath caress her cheek.

“Only what you want Brienne and nothing less,” he promised.

Her already tight nipples tightened further, and she cried out as the first set of hands begin to caress her small breasts.

“Are you ready for us to fuck you, Brienne?” the voice behind her asked, his tongue drawing out the shell of her ear.

“Yes,” she consented, breathless, unable to control the pounding of her heart.

One hand pulled down the dress’ zipper as another pair slowly pulled down her straps. In a matter of seconds, she was naked against them and unable to think. Two pairs of large, warm hands began to caress her everywhere. A rush of sensations flooded her as lips joined, humming their appreciation against her scarlet, heated skin.

She cried out as Jaime’s mouth engulfed her nipple, sucking it deep into his scorching month. Addam’s hands pulled her ass towards him, cradling his cloth-covered, hard cock between her cheeks. She gasped at the contact and flinched.

“Nothing back here tonight, Brienne. I just love how this ass feels in my hands. So firm,” he soothed as his teeth bit down carefully on her earlobe.

“You feel so hard,” she found her voice as one of her hands carded through Jaime’s soft locks. She reached to squeeze the muscular thigh behind her.

“I’ll be hard all night because of you,” Addam assured.

She was beside herself with pleasure when she felt Jaime’s lips switch breasts. He gazed up at her with each bite and pull, comforting her with a concentrated swirl of his tongue. She felt Addam’s hand move to cup her unoccupied breast, his long fingers pinching her nipple to make her moan louder.

She nearly screamed as Jaime’s finger slipped between her drenched folds, his lips slipping away from her small breast.

“So wet, Brienne. We’ll make sure to keep it that way all night,” he smiled deviously as he slid his finger deeper inside her.

“Oh Gods, Jaime…”

“It’ll be his cunt and my pussy to keep occupied tonight,” Addam added huskily.

Lost in sensation, she was unsure how she found herself on the bed. Jaime spread her legs to accommodate himself between them as Addams moved to her side, his mouth tasting any skin available to him.

“I can’t wait to taste all of you,” Jaime groaned as his lips traced her hips, making a trail to the spot she needed his mouth the most.

Brienne reached for both men, her hands touching them anywhere they can reach. One, firmly on Addam’s broad back and the other holding onto Jaime’s gorgeously silky hair. She tried to be gentle with her tugs when his teeth scraped across certain spots. Her body arched the moment his mouth finally parted her dripping folds, the feel of his tongue licking her for the first time causing her to moan so loudly she didn’t care who might hear.

Her eyes closed tightly when she felt everything cease. Her breathing went ragged at the loss of sentation. She opened her eyes to find them staring at her.

“Keep those beautiful eyes open and on us,” Jaime throatily instructed, lips slightly wet. “Remember whose making you cum tonight.”

She could only nod in agreement, willing to give him anything he asked for at that moment.

Jaime’s mouth moved back to where she wanted it most, lips teasing once more before delving into her heat.

“Please… please…”, she pleaded as she held his head against her tightly.

And he didn’t stop. Tasting her; enjoying her like his favorite meal.

When the first orgasm came, it hit her like nothing she had ever felt before. She felt the strength of them, holding her against them as she shook against the sensation of their large bodies around her. Jaime’s face sparkled with her juices up to his chin, the lewd smile on his face making her bite at her lips.

A pair of fingers slipped back into her sensitive folds causing her to shake.

“My turn to taste you,” Addam whispered as he let his finger slip out.

They gave her a moment to recuperate as they both took off their own garments, and Brienne had the best view of her life. Tight, plump asses, and cocks she could have only dreamed of.

She remained on the bed, slight aftershocks cursing through her, trying to think past the warm fuzziness in her brain. If this was any indication of how the night would go, she wasn’t sure she’d survive its pleasure.

“My turn to taste that sweet pussy,” Addam said with a grin.

They moved slower this time, seeming to know how over stimulated she was. Jaime nuzzled her sweetly as Adam began his warm kisses on her thighs. Jaime’s large, warm hands caressed all of her skin he could reach as his mouth followed in a whispered, wet kiss.

But it wasn’t enough for her. She wanted to touch him, wanted to hold what would be inside of her soon.

“Jaime, I want to touch you,” her voice quivered as Addam hummed against her mound, his touch still light.

Jaime looked up at her, his eyes so intense, searching hers.

“Do you want to touch my cock, Brienne? Because it’s been dreaming about you touching it for some time now,” he whispered in her ear.

It made her whimper, confirming what she has secretly dreamed of.

“I want to feel it… taste it… fuck it,” she whimpered, simply not caring how desperate she sounded.

He took her hand in his and repositioned himself on the bed, groaning loudly as he wrapped her hand around his length.

Thick and hard and smooth and hot and everything she’s ever wanted.

She moved against Addam’s mouth, matching the speed of his tongue in her cunt. Her whimpers began to increase. The look on Jaime’s face alone made her want to come. But before she could increase the speed of her hand on his cock he stopped her, bringing up her once occupied hand to his lips and kissing the palm.

“No more for now Brienne, I want to fuck you first,” he declared, his short breaths ghosting over her heated skin. “But later, you can touch it all you want.”

“Yes, please Yes!” she cried out as her third orgasm from Adams skillful mouth overtook her.

When Jaime finally filled her it’s with Addam watching them.

The words spilled out of Brienne, gasping in time with Jaime’s thrusts. “Fuck me deep Jaime… I want to feel you for days.”

She hears him groan at her request, his fingers gripping her hips tightly and thrusted inside her in one heavy, forceful swoop, burying himself inside her to the hilt.

Her back arched off the bed, screaming his name, wondering how it was possible to feel so full.

“Fuck Brienne… fuck,” he mumbled, reaching for her hands, squeezing tight as he held her against the mattress, a rush of words escaping his lips.

“So fucken tight… hot and tight… so good Brienne…”

Spreading her legs wider, he sank in deeper, causing them both to curse.

“I need to touch you… fuck… you feel so big…”

The moment he untwines their hands, she wraps herself around him, hands holding onto his strong broad back, pulling him tightly against her. He rocked against her, starting their dance.

His nose grazed her neck, as his lips moved up to kiss her chin, his question a puff against her lips.

“Ready?”

“Yes,” she immediately replied.

And then he started to fuck her, slow and deep, each new thrust a little harder.

“Yes, please.. fuck, yes, yes, yes,” she moaned, unable to stop.

It become a flurry of raw and hungry strokes, strokes that craved more, needed more, desperate for more.

“Gods! Fuck… so good… so good… fuck,” his lips so close to hers, his sweaty body melting in hers. Her nails dig into his back as his finger moves to rub at her over-stimulated clit.

Unable to only feel and no longer able to reason her lips pressed hard against his, wanting to be swallowed up my him in every way. He kissed her back fiercely, slamming into her as she screamed her release into his month, her fingers digging deeper into his shoulder. He followed her over the edge, moaning her name moments later.

Little aftershocks kept them connected, only pulling apart with care after. His lips left hers softly, his eyes still focused on hers.

“I didn’t…I know…” she tried to speak, but with her body so relaxed, her brain was unable to complete sentences.

“Just means you can only kiss me now,” Jaime smiled, his lips kissing hers softly, moving down to her neck.

She turned her head slightly to catch the moment Addam released, groaning as he spilled onto his stomach.

By the Gods, it’s one of the sexist things she had ever seen.

Jaime pulled her attention back to him, nuzzling her face with the tip of his nose.

“We should clean up. We aren’t done by a long shot.”

Brienne smiled the largest smile she’s ever felt at his words, hoping to survive the night.

After some nourishment and clean up for all, the festivities continued. Addam took her from behind, his cock longer but less thick than Jaime’s but no less satisfying. She tasted one, then the other, as different fingers filled her cunt each time.

She rode one as she filled her month with the other, letting Addam spill on her breasts as she found her climax, squeezing Jaime for all his worth.

By the time her body gave out, it was Jaime’s arms that pulled her under the covers, promises of a deep soak once they woke up.

But before she drifted to sleep, a different pair of lips kissed hers.

“Thank you, Brienne. I do hope we can do this again,” Addam softly whispered in the dark.

She gave him a sweet smile as she drifted off into sleep, Jaime’s strong arms holding her and a fluffy comforter cradling her.