Archive of Our Own

Lily tossed her golden brown hair over her bare shoulder. She wasn’t usually the tube top and short-shorts kind of girl. She aimed for serious and professional attire, largely because she knew people barely took her seriously as is, but this was an exception. This was a real vacation, for the first time in years - one whole month at a gorgeous lakefront cottage on its own private lake. No motor boats were even allowed on the water to distract from the delirious quiet of the location. 

Pulling up in front of her friends’ apartment building, she popped the trunk of the convertible and climbed out. She had it open and waiting as her friends tumbled out of the building, shining hair and long glossy limbs in shorts and sundresses. The trunk was crammed full as the three other girls loaded in their gear. 

“Are you sure we have everything?” Harmony worried. The redhead was a notorious worrier. 

Lily nudged her shoulder reassuringly and nodded as she replied, “The cabin comes well stocked and we can hit the market in the nearby town for anything extra we need. Now hurry up, you know if Jane and Emily beat us there then they will definitely steal the best bedrooms.”

“Good point.” Risa muttered, climbed into the backseat and pulled out her phone to hook it up to Lily’s bluetooth. Elena nestled beside her. The two dark-haired beauties worked at the same engineering company and one would think they’d be sick of each other’s company. However, it appeared that Risa and Elena were incapable of being separated. 

Harmony slid into the front passenger seat as Lily rearranged the trunk so it would actually close around all their luggage. She could hear Harmony continuing to fuss, apparently unable to help herself, “You two good with the backseat?” 

“You know those two nerds will end up talking the entire time anyway. They can’t help themselves.” Lily interjected to Elena’s gasp of feigned outrage. It felt good to get behind the wheel again, stretching out on the highway, letting it consume the kilometres as Risa’s playlist filled the car with music to accompany the soft giggles and discussions about the weeks ahead. Lily let it all just float over and around her. She savoured the pull of the drive, the brilliant sunshine overhead and the roar of the vehicle. By lunch, they were pulling into the small town that was less than an hour away from the cottage.

“Let’s get a few things here. I have been assured there are staples at the cabin so concentrate on perishables.” Lily instructed.

“Yes, bossy boots.” Harmony teased as she clambered out of the vehicle, stretching such that her short dress nearly flashed panty. Elena tugged it down and Harmony laughed, seeming to suddenly realise they were in town and could be seen. Elena’s shorts were a scandal, barely covering her round butt and her bikini top didn’t exactly hide much. Risa’s knee length sundress with the tiny spaghetti straps was downright conservative compared to the rest of them, or would be if it wasn’t so sheer. As they strolled through the open air market, picking out fruit, Lily noticed the locals giving them the once over but with that mild sort of approval. Pretty girls having a good time were rarely offensive, especially in these tourist trap towns which counted on their summer patronage. It was good to see a proper small community again, where men were appropriately deferential. 

They hit the indoor market like a tornado, picking up dairy, items for the grill and ice cream. The liquor store was last but since none of them were big drinkers, it was just a few bottles of wine and mixed cooler style drinks. The convertible felt overstuffed, most of them having to hold some of the groceries on their laps as they travelled the rest of the way to the cottage. 

As they rounded the gated entrance, held open for them, Lily slowed the car just a little to appreciate the beauty. A mountain gleamed in the distance and the trees towered overhead, casting shadows even in the warmth of the day. Harmony let out a soft gasp when the trees parted enough for them to see the lake and cottage in the distance. 

“Oh Lily. How did you get this place?” Elena asked, her voice awed by the beauty. Elena had grown up in a dusty desert town. This kind of lush greenery was new to her and she apparently loved it as much as Lily, who had grown up in the City.

“Friend of my old boss owns it. When I mentioned our previous rental cancelled on us, she called in a favour.” Lily explained.

“We should definitely send her a thank you note and some wine.” Harmony murmured as Lily continued to drive. The cottage came into view and it was even more lovely up close. It was a classic log cabin but with big windows, thrown open at present to catch every breeze. The entire structure had a broad wrap around porch overlooking the lake in the distance. Carrying bags of groceries, they were almost at the door when it was thrown open. 

A man stood there. He was handsome in that unassuming way. He looked to be in his late thirties, with a stocky sort of build. He had an olive-toned complexion, dark curls and a winsome smile. She knew the girls would have fun with this one. It was strange having a man own such property but odd things did happen every now and then. “Hello. Come on in. Please. I’m Jack Sampson. This is my cottage.” he greeted, stepping back as he did so. 

The cottage was lovely with six good sized bedrooms and one bathroom on the upper floor. On the main level there was a kitchen with a large passthrough to a dining room. There was another bathroom with a separate tub and a spa shower with gorgeous looking jets. The living room was big enough for a dozen people with reading nooks and a window seat that had a gorgeous view of the lake beyond. There was also a library sort of office room. “I have just updated everything in here, so you should have a lot of choices should you want something to read. There are also puzzles and board games. I’m still working on getting a good wifi signal throughout the house. It is definitely best here or in the living room. The bedrooms are spotty. I’m sorry about that.” 

“Do you stay here?” Elena asked the question all of them were thinking, especially the girls into dick. Lily was not but good service from an obedient man was always a pleasure. 

“No, oh no, I’ll mostly leave you in peace. I have a small cabin about a fifteen minute walk away. I can be here quickly if there is an emergency but otherwise I’ll stay out of your way. I wasn’t expecting to have guests this month so I am still completing a few projects but I will try not to be an annoyance.”

The man then promptly excused himself and just…just left. Lily was appalled. What kind of man didn’t offer to serve? It was perplexing. The situation did not improve. It would have been less troubling but when he was around and did not believe himself to be seen, she would catch him looking, with something akin to an ogle, at Elena’s tits, at Emily’s long legs, at her ass, at all of them really. She could see his interest.

However, his rudeness continued. Jane held up a bottle of sunscreen one day and asked him to apply it and the man declined. Just said no, like that was a permissible answer. He was the most bizarre combination of obedient and disrespectful she had ever seen. When he came down to show them the boats, Elena asked him to take her out in one, wearing a downright tiny bikini and despite the fact the man clearly checked out the brunette, he said no.

Lily almost died of shock. First, it was almost funny but as the days passed, her initial shocked bemusement settled into real anger. They obviously had to do something but what? Finally after a semi-drunken night, a decision was made. 

Lily waited until she saw Jack arrive and she tried to contain her irritation with the man. His disobedience was ongoing and unacceptable. Risa and Elena were annoyed too but too soft to take care of it. Jane would make it too much of a game. She, Harmony and Emily drew straws and Lily had won, or lost, depending on how they defined it. The other girls had piled into the cars and headed into town for a little shopping and a lazy lunch at the market while Lily took care of setting appropriate boundaries.

“Hello, Lily.” he greeted, a smile warming his features.

“Hello Jack.” she replied but there was no bright smile in return. His smile flickered and faded. 

“Everything alright?”

Lily sighed and shook her head. “C’mon. I want to talk to you for a bit.” She turned on her heel and headed for the library room that was also a delightful office. It was one of her favourite spaces in the cottage with its old leather chairs, broad table that served as a desk and shelves of books from current best sellers to old leather bound volumes. She and Elena had already dipped heavily into those shelves. 

Jack followed, indicating to her that she was entirely correct about the man. He just needed a firm hand and they were the girls that would give it to him, starting with Lily. She seated herself on the desk and gestured to one of the chairs in front of it, the one close enough for her to touch him in her current location. He reached for the other one.

“No Jack. Here.” she gestured at the chair again. He flushed but followed her instruction.

“Is something wrong, Lily?” he asked quietly.

“Your cottage is lovely. The location is amazing and all the amenities, from the hot tub on the back deck to the boats by the dock are absolutely wonderful. But there is a niggling disappointment and frankly it is starting to taint everything.” 

He jerked in his seat, clearly shocked by these words, “Is there something I can do?”

“Yes, because the problem is you.”

“Me?” he exclaimed. “What did I do?”

“Your continued disobedience is unacceptable.”

“I…I… what?” he stared, “What haven’t I….”

“You were asked to help Jane with her sunscreen. You declined. You were asked to help Elena with the boat, declined. I asked you to put lotion on my back, another decline. Dinner, decline,” She rattled the offences off, counting them down on her fingers while regarding him with a stern expression. There was frustration she was trying to contain in her voice, “You even started using our first names instead of appropriately addressing us as Miss or Mistress.”

“But that w-w-would be in..inappropriate.” he tried to interject. 

“That’s it. I’ve had enough.” Lily slid down from the desktop and then patted it with her hand. “Bend over. Chest here.”

“What… No…I…”

“Do not make me repeat myself.” her voice took on a hard edge, one that caused most people to watch her apprehensively. He rose to his feet and then leaned over the desk, chest down. He was clearly confused, which in any other circumstance would be quite adorable. She loved taking control of men older than her. This one wasn’t quite old enough. Maybe fifteen years older, tops. She preferred at least double her age. Her hands circled his waist and started to unbuckled his belt. 

“Please.” he whispered.

“You’ll feel better once the boundaries are in place but you must be corrected for your earlier failures. Do you understand?”

He hesitated for a long moment, the seconds ticking by but then he said, “Yes.”

“Yes what?”

A shudder ran through him and with her hands where they were she could feel his cock stiffening. Oh yes, they had been entirely right about him. The next three weeks were going to be so much better, she was sure of it. He just hadn’t had anyone hold him accountable to proper behaviour in too long. 

“Yes, Mistress Lily.” he replied contritely. 

“What is your safeword?”

A soft sound, a cross between a moan and a sniffle came from his parted lips, “I…I the stoplight system, Mistress Lily.”

“Good boy. See. That wasn’t so hard now was it? It’s all going to feel better really soon, isn’t it?”

The pants came down easily enough but he whimpered a bit when his boxer briefs followed. His dusty olive toned skin looked to be in need of a good layer of colour and some lotion. Men never did use enough lotion, one more reason that she preferred women. However, this older fellow was going to learn a stern lesson today. She started with her bare hand. A firm smack followed by her rubbing over the spanked spot. He flinched, his hips jerking into the table but the blow was more about the humiliation of being disciplined by a girl so much younger than him, and not any real pain.

“From now on.” she stated harshly as she continued to spank him, “If one of us gives you an instruction, you will follow it, unless you are already under orders. You are ours. Now say it.”

“I … I am yours… Mistress Lily. You and the other girls, women, girls…” a soft shuddering cry issued as Lily picked up a wooden spanker, thin and a bit cruel, it was pliable, expensive and had a comfortable handle. Lily used it to work over Jack’s thighs and his sit-spots. Now he was making real noise, shuddering, broken sounds that only encouraged Lily.

“So when one of us asks you to apply sunscreen or lotion, what do you do?”

“What you say… I promise. I can be good. I was just…”

Lily spanked him hard, making him squeak out a sound, “I do not want your excuses. Pathetic, miserable excuses, as if we didn’t see the way your eyes rest on us, on the way you look at our legs and asses and tits when we are out on the beach or sitting outside. You want to touch us, caress us and then you are rude and stupid and don’t do what you are told. You want to touch us, don’t you? Admit it right now!”

“I do… I do…” he confessed, a broken sound that finally seemed to send him into tears.

Lily set down the spanker and reached low enough to pull Jack’s belt out from the loops of his jeans. “You are a dirty man. Filthy slut and you deserve your spanking. You are wilful and disobedient. You are so lucky we are prepared to give you a chance to make this right, serve us properly. You should be grateful. Are you grateful?”

She folded the belt so that the buckle rested in her palm and then swung, making him jump and cry out again. “Mistress Lily, please!” he cried out, begging, soft, almost incomprehensible, pleas for her mercy. As if she had any for a man? It was laughable.

The belt was thick and made lovely dark stripes on his spanked ass. “Are you grateful for your second chance, Jack? Thank me for being so kind to you.”

“You are gracious and perfect and kind… thank you Mistress Lily. Thank you.” he sobbed, his voice heavy and anxious. 

Lily set down the belt and touched his shoulder. “Come here,” she instructed, her voice soft now, lush and alluring. She guided the shaking man over to the deep leather chairs, soft with age and so ridiculously comfortable. She sat down and stripped off the rest of his clothing before having him come to kneel in front of her. Her hand slipped up his back, stroking his warm skin, now hot. His face was covered in tears, flushed red, and his nose was running. Those lovely dark curls were messy now. She picked up a handkerchief and dabbed at his cheeks, clearing away some of the result of her attention. 

“That was a good warm up. I bet you’re feeling better now, hmmm? Come… I’ll let you have a little reward, a little comfort before we go upstairs for the proper spanking.” Lily soothed as she lowered the strap of her sundress, revealing that she was not wearing a bra. Her hand curled around the nape of his neck and pulled him in. He latched with a soft shudder and began to suck on her breast. It was tentative at first but as she soothed and stroked, kissing the top of his head and the curve of his cheek, he settled in. He sucked gently then built to a fierce, pulling tug and Lily smiled at him.

“See…good boys who do what they are told get treats. Don’t you want to be my good boy?”

He nodded, breaking off his suction but flicking out his tongue to tease over the peak before he replied, “I do. I didn’t…I’m so sorry I was bad. I thought I was imagining it or you were just teasing me…I didn’t understand. I’m so sorry.”

“Shhhh…I know you are sorry and it is such a shame you already wasted an entire week with your poor behaviour. But you are going to do so much better from now on, aren’t you? I know every one of us girls is going to be pleased with our Jack. Are you ready for your proper spanking now?” 

He shuddered again, aching and needy. Nude she could see how hard his cock was, how it already dripped a little precum onto the floor. “Yes, Mistress Lily.”  Then his mouth latched again, sucking firmly on her peaked nipple. 

Lily laughed, soft and indulgent. “You can have another suckle later, dear boy. C’mon up with you. Then you are going to give me your hand and help me up too.”

Jack pressed another soft kiss to her breast before gently pulling up the strap. He rose to his feet and held out his hand toward her. She took it and did not let go. Instead, she led him out of the library, up the stairs and into her bedroom. It wasn’t one of the larger rooms but it had a stunning view of the mountains behind the building. Her clothing was all put away, her suitcases neatly stowed and she even set out a few personal items, making it truly look like her room. Jack hesitated as she took a seat on the mattress and then reached for him.

It took a few minutes to arrange him as she wanted, a pillow under his hips, propping him up. Already his ass glowed a bright red and she teased a fingertip over the curve and watched him flinch and hiss between his teeth.

“That was a good warm up wasn’t it, Jack?”

“Yes, Mistress Lily. You have a strong arm.” he affirmed. 

“Wait until Emily gives you your maintenance spanking, she makes me look like a weakling.” Lily teased and Jack’s eyes snapped to her face. His limbs trembled.

“Maintenance, Mistress Lily?” 

She nodded, “Since you wasted an entire week already, it’ll be required daily. You will also probably need to move your essentials into the building since you have a lot of service to make up and we can’t have you spending unnecessary time going back and forth every day.” Lily leaned in to kiss Jack’s shoulder, savouring his delightful obedience. 

“Yes, Mistress Lily.”

“When you see the girls again, you will apologise to them for your foolish behaviour. I am sure that most of them will be forgiving. After all, you are just a silly slutty man and we all know they don’t always think properly.”

“You are all just so beautiful. It…it was too much to hope.” he muttered and her heart, already softening, melted completely.

“Of course it must have seemed too much. I do forgive you. I am sure the other girls will too. And you are so brave for honouring your mistakes and being such a good, apologetic boy. I was so worried you’d make a real fuss today but you’ve been such a delightful man. You’ve taken your spanking so well and I am going to work on finishing it now, okay?”

“Yes, thank you Mistress. I … I appreciate your forgiveness.” 

She started with her hand again, savouring the heat and the warmth of him. The sun poured through the windows over him, adding a brightness to the event that made it almost feel a little magical. He whimpered and writhed against her bed, as all men do really when punished. But he took it well. When she picked up the tawse, he made a terrible deep shuddering sound that she delighted in. So she added a few extra strokes to the total. His ass and thighs glowed as she nudged them apart and worked on adding some colour to his inner thighs. When his words and sobs were inarticulate, his entire body shaking, and his ass right at the cusp of impossibly dark red and glowing, she finally set down her implement. She fetched a cool cloth and wiped down his skin, washed his sweet face before applying the aftercare cream to his rosy ass and thighs.

Stretching out next to him, she caressed his upper back and shoulders as he curled around her, his lips seeking her breast again. She let the strap fall on the other side, giving him a fresh nipple to suckle until at last, the man fell asleep. She stayed with him for a few minutes, her fingertips gliding over Jack’s cheek and down his back as he slept. 

She forced herself away, changed into her bathing suit and went down to wade in the water. They had a rule, no swimming alone, but her skin felt flushed and her energy was at a boil after such an intoxicating punishment. Honestly she should make a point of doing it more often. It was only healthy and proper after all. Years they spent in training to ensure they were good Mistresses and she all too rarely used those hard earned and studied skills. She waded, savouring the cool water against her calves and feet. She heard the car before she saw it. She climbed out of the water, pushed her feet into her flip flops and walked up to greet the girls.

“Well?” Harmony asked.

Lily just grinned and the girls all laughed, warm and merry. 

Elena lifted two bags from the trunk and chimed in, “Oh thank goodness. Now we can have a proper beach day.”

“And we can discuss his maintenance schedule.” Emily said firmly.

“Knowing Lily, he got a hell of a roasting. Maybe we should give him a day or two to recover.” Risa proposed.

“Ah nooooo.” Jane said as she pulled open the door, a bag of vegetables in hand and a bottle of wine in the other. She shifted the bottle to the crook of her arm and pushed her sunglasses up from her nose to hold back the silky strands of her bright blonde hair. “He got what he deserved. And maintenance might suck for a few days but he needs it.” 

Everyone came to a stop when they spotted Jack in the kitchen. He was just wearing his boxers and he had an expression of uncertainty that indicated he wasn’t sure that was allowed but felt weird about walking around nude. Since she had not given him instruction either way, Lily was not angry but rather pleased he hadn’t been so foolish as to dress completely. 

“You’re right, Mistress Jane. I did deserve it and I do need it. I am so sorry if I spoiled anything, especially your vacation. You are all such clever and beautiful girls, I just didn’t think it was possible and I acted poorly. I hope you can forgive me. Please.”

Elena, of course, melted first. She was such a soft touch. She rushed across the room, tossed her grocery bags onto the counter and wrapped her arms around him. Her shorts pulled up and when Jack hugged her back, one hand curled under her bottom, stroking the silky skin he found there. 

“Was it just an awful spanking, Jack?” Elena inquired, pressing soft kisses to his cheek.

“Mistress Lily was very strict.” he conceded, his eyes flashing to Lily’s as he spoke, “But I am so grateful she settled me. I understand now. I’m sorry if I disappointed you, Mistress Elena.” 

Emily groaned before Elena could reply. “I’ll believe it when I see it. Stand still.” She glided over, her long sundress had a slit that bared her leg almost to her hip and when she walked over, bare feet on the cool hardwood, she placed her knee between Jack’s thighs and nudged them apart. He obeyed without hesitation. Elena had stepped back, also fascinated with seeing the results of Lily’s discipline session. Emily slipped her finger into the waistband and tugged it back. 

Lily smirked as Emily’s eyes grew wide, flashed up to Lily’s and then back down again. Jane stepped around the man to have a look and finally Harmony and Risa peeked in. Elena laughed out, “This is silly. Jack should just take them off and bend over the counter so we can all inspect him properly.”

Jack’s face was glowing red but not quite as red as his ass, which became immediately obvious when he followed Elena’s instructions. “Oh my, remind me never to piss you off, Lily. You’re a beast,” Jane muttered as she poked a finger into one bright ass cheek, making the man hiss and then moan at the touch. 

“So maybe less maintenance…” Harmony started.

“No. That doesn’t change my opinion. He deserves it and he needs it. He even said so.” Jane interjected, “It’ll be a rough week for him but honestly after being such a complete brat week one, it is what he deserves.”

Risa replied, “Complete brat is overstating. I mean… c’mon.” Even still she traced her fingertips over Jack’s ass and then sighed. “But at the same time, I still want to have my turn.”

He whimpered at the press of Risa’s hand but didn’t move. Lily could see the blazing blush in his cheek that travelled back to his ears and along his forehead now. His chest heaved in an effort to restrain himself from moving. “Now that we have things properly in hand, shall we put away the groceries and go down to the beach? I don’t think we’re going to have much fuss from our fellow here about sunscreen application any longer. He can give us a good going over and then collect his essentials from his place and get back in time to make us all dinner.” Lily proposed.

Jack straightened slowly, gauging permission carefully. Six different bossy little queens ordering about one man was probably a lot for the dear man but Lily had limited sympathy - not after his earlier disobedience. He had settled well, it was true, but she was still suspicious. 

He reached for his boxers but Emily beat him to it. “No, I don’t think that’ll be necessary but since you’ve been good, I’ll put your sunscreen on before we go outside.” 

Lily almost laughed at the wide-eyed astonishment on Jack’s face at those words. She touched his arm and his head snapped to look at her. His hand lifted, caressing the soft curve of her breast as if seeking reassurance. “You’re a good boy, Jack. I know this is hard but I am confident you can do it. Settle yourself.”

“Yes, Mistress Lily. I, just, this is a lot. I don’t want to disappoint again.”

“I’ll stay right here with you for the next bit. I’m sure if you behave yourself you can have another suckle soon,” Lily offered as comfort. His cock visibly jerked at the suggestion, making Elena and Harmony both giggle. 

“So he likes classic comfort hmm? I’d say he was just a silly boy but I love it too, feels so good doesn’t it?” Harmony affirmed, reaching up to run a hand along his back and dust through his hair. “Who is he sleeping with tonight?”

“Obviously whoever does his maintenance gets him for bed if she chooses so Lily, this time, unless you would prefer to decline? I know you like punishing men way more than you like fucking them.” Jane stated as she slipped the snacks she was carrying into a low drawer and then gave it a shove with her hip to close it. 

Lily paused, thought about it for a moment and then nodded, “Sorry girls, he’s mine tonight. I want to warm him up a little more and then have him lick me out.”

“Ooops, there he goes.” Elena murmured, acknowledging Jack’s rising interest with some amusement. His size was quite satisfactory, even Lily had to admit that. 

“At least we know he doesn’t object to the suggestion.” Then Elena leaned in and pressed a kiss to his shoulder, “I’m going to go get changed and get my sunscreen. Stay here.” 

Lily was the last to leave the kitchen, leaving the man looking almost bewildered at how his life had changed. She wondered if the degradation and humiliation bothered him as much as it turned him on or if it had all settled into a strange blur for him. She visited the washroom, pulled her hair up into a slick ponytail and perched her sunglasses on her head. She was already in her bathing suit. Her bikini was a simple black string affair because she liked minimal tan lines and the thong was oddly quite comfortable. Also she remembered Jack’s gaze on her the first time she had worn it and knew he liked it, even when he was pretending not to notice them in that way. Risa was in an equally brief bikini while Elena’s had more of a bandeau style top so a little more fabric to cover up. It was unnecessary in Lily’s opinion but fortunately the other three girls made up for it, in tiny triangles of fabric and the only one with a full bathing suit bottom was Elena. Their newly reformed man was getting quite the eyeful. 

“Do you want me to grab your water bottle, Emily?”  Elena offered as she reached into the fridge to pull out hers. 

“Sure.” Emily murmured as she uncapped the sunscreen and poured a large dollop into her palm. It was probably cruel of them to all watch but they did. Watched as she started on his back and shoulders before moving to his chest. Only then did Emily move her way downward. Knowing she was being observed seemed to have inspired her to make it more of a show. Jack’s cock was hard before she ever put her hands on it. She smoothed the sunscreen over his length and then down to his balls, squeezing, testing their weight and then gliding down his inner thighs. He was shaking, tears on his cheeks as she slid her hands down his legs and then back up the other side. His sobs became audible when she reached the back of his thighs. By the time Emily was finished, he was a shaking mess. “Good boy.” Emily said with a soft pat to his tender ass.

“Thank you, Mistress Emily.” he managed to get out between sobs. 

“Let’s walk down to the beach. He can apply our sunscreen down there.” Elena suggested as she reached for Jack’s hand and gave it a gentle squeeze. “Such a good boy. Just think you could have been giving us these kinds of rubdowns the whole time.”

“I was very silly, Mistress Elena. But I didn’t understand. I really didn’t.”

“I know, which is why we forgive you.” 

“Thank you, Mistress Elena.” 

Lily smiled at him approvingly and nodded at him as he passed. The walk down to the water, a mere five minute journey, was so entertaining to her, watching his bare butt next to all her friends’ glorious beauty. It really was such a silly thing but then again most men were. She directed him quietly to take care of the others first and then come to her. Her chair was half in the shade as she was not looking to get a burn this summer, just a nice even golden colour. 

Jack approached, his thick cock still quite hard, hard enough that as his slick hand slid over her skin, applying the sunscreen, she toyed with it. She ran her fingers up and then down. She held the weight of his balls in one hand and stroked his shaft with the other. A pinch applied to the base of it made him gasp, loudly, and drop the bottle of sunscreen. 

“Sorry Mistress Lily.” he whispered as he picked up the bottle again.

“It’s alright, Jack. This has been an intense day but now that you are behaving properly I find myself unwilling to stop toying with you. That is quite mean of me, isn’t it?” she murmured quietly as she turned over so he could apply the sunscreen to her back. His fingers plucked at the string of her top, parting it completely. He smoothed it out of the way and then rubbed in the fluid, almost as if he were giving her a massage. He glided his hand over the curve of her ass, toying with it, stroking her. It reminded her of worship, gentle and loving.

“Jack?”

“Yes, Mistress Lily?”

“It’s okay. If you want to, I wouldn’t mind.”

“Really?” his voice broke over the word and she had to laugh as he then tried to correct it. “I mean, thank you. I mean, Mistress Lily.” She laid her head down on her arms, letting her cheek rest against her smooth skin, sun warmed and smelling of sunscreen.

Her suit was adjusted to the side, her thighs parting that much further as his tongue flicked over her. His hand slipped under her belly, lifting her slightly as he settled into place. The spanking earlier had gotten her wet so it didn’t take his tongue long to have her groaning quietly. She offered little in the way of assistance, making him work hard to have her cum. He smoothed the suit back into place when he was done and applied a little more sunscreen to her inner thighs and if his fingers pressed into her pussy a few times while he did so, well she found no cause to object. He retied the strings of her top carefully, dusting his cheek against her shoulder. 

“Thank you, Mistress Lily.”

Lily lifted her head and smiled at him, “Good job. Go ahead and get your things. You’re in charge of dinner tonight.”

He scrambled away, unable to hide the fact that he once again was incredibly hard. By the time she ventured up to the house again hours later, he was in the kitchen, wearing an apron and his boxer briefs but fair enough when he was cooking. She rinsed off from the beach and pulled on a short sundress, not bothering with underwear. When she came down, she found most of the girls had thought the same. Only Emily was wearing a loose pair of sweats with a tank top that did nothing to hide her braless state. Apparently they were going commando given they had a boy to play with and Lily, who loved the look of half naked women, certainly had no cause to object. 

Elena poured her a glass of white wine, cool and refreshing after the afternoon at the beach. Lily sipped it as she took a seat at the kitchen island. It seemed their Jack was a competent cook by the looks of it and Lily was impressed. The others had wandered away, talking among themselves, gossiping about this and that. Lily reached out and brushed her hand down his arm. His eyes shot up to hers and he smiled, “You look happier, Mistress Lily.”

“I am now. How do you feel?”

He shrugged lightly, turning his attention back to his task, “Settled. Better. A little nervous about trying to keep up with so many women.”

Lily looked around and nodded, “Do you have a friend who can come help you serve? We can give him a good roasting too and settle you both into it?” 

“Oh I….” he paused, thought about it, and nodded, “There is someone I could call. If you think that would be a good idea?”

“That doesn’t mean you aren’t going to get some time with each of us but that may take the edge off. Let me know if he consents.” Lily murmured.

“Could…could someone else be his first big… I mean, Mistress Lily, could I….” he stopped and Lily couldn’t help but grin.

“The girls would never be so generous as to let me have both of you anyway so yes, obviously. One of them will take care of your friend.” Lily turned to look at her dearest friends, “Our Jack might need a little help managing all of us so he’s going to see if a friend can come help him with his service. Who wants to be the first roaster to catch the poor fellow up? Assuming he says yes of course?”

“ME!” Three of the five women exclaimed at once, making both Lily and Jack laugh.

As dinner was served, Jack was required to kneel by Lily’s chair, as it was her maintenance day and therefore she was his primary. She fed him bites of food and pressed kisses to his cheek. Jane was blatantly envious and particularly irked that Harmony had won the short straw contest for discipline number two of the day. Jack had already called his friend and the man was expected any time. 

Dessert was just being served when they heard a tap at the door. “That’s for me…please excuse me ladies.” Jack murmured, excusing himself.

~

Mark set his duffle bag on the deck and stared at Jack’s cottage, which looked much the same as always with the exception of the collection of what looked like colourful strings and microscopic fabric hanging over the porch railing. His friend had gotten into a pickle with some renters and needed help managing six young women. Hard to believe but that was what he understood. Given he was currently on leave, Mark had spent plenty of time with Jack at his cottage over the last few months and the man knew he was available. 

The door creaked open and Mark blinked and tried to process this red faced man wearing only his boxers out on the front porch. “Jack? Are you okay?”

“I need your help. There are six of them. Six. I can’t… I thought they were just teasing at first but they got mad that I wasn't taking orders properly.” his friend started, his words rushing together.

“What?”

“Look!” His friend turned and tugged down his briefs slightly, showing off a particularly well spanked ass. Mark gasped despite himself and then felt embarrassed. It was just a spanking after all. Most men got them at one point or another. Women had every right to discipline. It was just a long damn time since either of them had gotten such attention. 

“Jack…I’m…it’s okay. You know, a few weeks…it’ll probably be good for you.” Mark started.

Jack turned and met his eyes, desperation shining through, “Please, I need someone to help me for the next three weeks. Will you stay? Will you help me?” 

“Yeah, of course.” Mark couldn’t say no. Not to his friend who was so obviously upset and feeling overwhelmed. 

The relief was palpable as Jack surged forward and wrapped his arms around him. “Thank you. Thank you so much. It’s… they already drew straws on who would take care of you tonight.”

“What? Take care of me? Why? I didn’t…do anything.” he stammered out.

Jack shrugged, “I know but they said something about it being fair given I got a roasting. That the other girls deserved a chance to apply one too and to make it even between us. I think it is just an excuse. They are riding a summer high and I think they just want to. I’m sorry, you’ll still stay, right?”

His pulse started to pick up. Six young women and only two men available to serve them? This was going to be a long three weeks, especially if they were already applying absolute rippers of punishments like this. He shouldn’t be excited but fuck, it had been a long time since any women paid much attention to him. “Of course.” 

Mark was practically pulled through the door and his bag followed, set on a low bench near the entrance. A collection of sandals and flipflops were by the door. Jesus, there were only six of them, right, he thought as Jack tugged him through. He wasn’t sure what he expected but this glorious collection of glossy beauties was not it.

“Everyone, I’d like you to meet my friend, Mark Kopin. He is taking a sabbatical this year and has helped me with renovations to this place. He’s almost as familiar with it as I am. He has kindly agreed to help me with serving you for the next three weeks or as long as you would like him here I guess. Mark, I’d like to introduce you to the Mistresses staying here for this month. This is Elena, Risa, Harmony, Emily, Jane and Lily. Lily is in charge of my discipline today.”

Mark was sure he was sweating. He should be at least. Fucking hell, it had been years since he’d had this many gorgeous women even know he existed much less looking at him so intently. “Hello Mistresses. Thank you for the invitation. I look forward to serving you.” he tried for good manners because legitimately it was a necessary refuge.

Mistress Lily rose to her feet and circled around the table to stand in front of both him and Jack. “Hello Mark. I hope you understand that we know you haven’t done anything wrong but Jack got a fairly intense discipline session today and is going to get another one shortly. We just don’t think it is fair for him to be punished so thoroughly and for you to remain as you are. Do you understand what I am saying?”

She was so calm and collected that the temptation to kneel in front of her and kiss her feet was strong. He nodded, “I understand completely, Mistress. I wouldn’t want there to be bad feeling between Jack and me either so I know I’ll probably regret this shortly but I consent to whatever discipline schedule you feel is appropriate.”

Lily’s smile was broad and he felt himself melt that much further. Oh fuck, he was in so much trouble. “I am so pleased. Jack, what a clever man you are for finding so quickly a perfect supplement to your service.” She tipped her head up to press a gentle kiss to the curve of Jack’s mouth. “Go clean up the kitchen and then head up to my room. Good job. Dinner was lovely.” 

Jack shot him a look of profound gratitude and Mark’s relief at helping his friend in this sticky situation made what he knew to be forthcoming almost worth it. Mistress Lily turned to him, hand coming up to run over his cheek, toying with his beard as she did so. “What is your safeword?”

“Lemon for slow down or discussion, Melon for stop.”

“Melon?” she laughed out.

“Hate them so seemed a perfect choice, Mistress Lily.” 

The women laughed and the pleasure that buzzed through him at that sound was intoxicating. “Alright, this is Harmony.” Lily gestured to a pretty redhead with bright eyes. He just wished he couldn’t see the play of muscle in her arm. This girl wasn’t weak. This was going to hurt.

“Good evening, Mistress Harmony.” he murmured.

“Harmony is going to prepare you and you’ll stay with her tonight. We’ll work out a schedule so you and Jack rotate through all of us. We are straightforward girls so no mean games, I promise. But that said, we expect our instructions to be followed, unless you are already following another girl’s instructions. You’ll look primarily to your maintenance person for that assigned day to simplify matters. Safewords are always honoured. We are respectable girls after all but that said, you can expect daily maintenance for the next three weeks. After today’s proper roasting of course.”

He swallowed hard, the lump in his throat threatened to choke him, and not for fear but due to the rush of intense excitement. This sounded like fucking heaven to him. He hadn’t gotten daily anything in years. “I will do my very best to serve you, all of you, and help my friend please you and enjoy your time here.” Mark managed to get out and ignore the strain of his cock in his jeans. He could hear the water running in the kitchen as Jack cleaned up the dinner mess but knowing his friend that wouldn’t take long. He was a clean as you go kind of guy. 

Harmony smiled up at him, “Well we were quite naughty and mean with Jack today but it does feel wrong for him to have had to show us all his bits and pieces and you to get the privilege of going to my room to strip.”

“Ohhh fair point, Harmony.” the blonde stated, her eyes watching him speculatively. If he remembered correctly that one was Jane. She looked like a cat with cream, all soft skin and a silky sort of mischief. The two brunettes at the end were giggling to each other and then looking him over. 

“Are you instructing me to remove my clothing, Mistress Harmony?” he asked, not wanting to make an error in mere minutes after his arrival.

“I am, Mark. Strip please. Then I will take you upstairs for a proper one.” 

He waited for the embarrassment, the sense of humiliation but he saw no cruelty in their expressions. Mischief, pride, interest, humour and even kindness all resonated there but nothing that made him fear for his safety. He was sure if Jack had that bad feeling, he would have kept him away. Instead he felt a tingling sense of building contentment. He loved clear orders. He loved attention. So he began to undress, neatly folding and stacking his clothing on a low chair and then stood still, raising his hands to place them behind his neck, his feet spreading to allow a proper inspection.

“Oh he is a good boy!” one of the little brunettes said. Fuck they both had gorgeous mouths. Stop looking, stop looking, he reminded himself. He was making himself hard. They might not like that, he scolded himself. Lily nodded approvingly but she turned, disappearing into the kitchen area. The other five women rose to their feet, almost in unison and he drew in a sharp breath, reminding himself not to move. 

He kept his gaze straight ahead as they circled, stroked, caressed. He felt fingertips pressing into his skin, holding his cock, cradling his balls and fingernails grazing over his skin. “There isn’t a mark on him,” Harmony murmured. He flushed, not wanting to admit that he hadn’t gotten a request for personal service in at least two years, maybe longer.

The tallest of them, with long light brown wavy hair and a reserved expression, replied with a soft laugh, “You’ll soon fix that, Harmony!”  The rest of the girls giggled and the apprehension muddled with intense lust at such focused attention. 

“Please, Mistress?” he asked, not at all sure what he was asking for but needing something, some reassurance from her. She rose up to her toes and dusted a soft kiss over his lips. 

“Come on, Mark. Time to begin, yes?”

“Yes Mistress.” Mark replied, relaxing his posture so he could follow her. A hundred times he had climbed these stairs before but they had never felt so long or so short. He also had never walked up naked before so there was a first time for everything it seemed. There were six bedrooms on this level so he followed Harmony to the one that was hers. He looked up in time to see Lily close the door to her room, Jack behind her. He caught his friend’s eyes and nodded, offering an encouraging smile. The door shut and he followed Harmony into hers. It was a mess, clothing everywhere, a tangle of swimsuits on one dresser top and a small pile of cheerful bright fabrics at the end of the bed. Compulsively, he started to tidy, shaking out and hanging up each item. Harmony sat herself on the bed, watching him with some amusement. 

“Are you sure you don’t have a group of women you already take care of?”

Mark laughed, “Ah no, just me, for a long time now.” He shrugged as he reached for the pile of swimsuits, sorting out the pieces. He held up one and couldn’t figure out which part was the front or the back. His brain sizzled slightly. 

“Like that one?” she murmured, glancing down his body as she said it.

He looked down and realised that he forgot for a moment he was naked. “Oh I…I was picturing how this would umm look on…well, you.” Fucking hell, at this rate, he was going to earn his punishment.

“Leave those things and come here.” 

“Yes Mistress.” He crossed the short distance to the bed, looking down into those warm blue eyes, he felt a shiver of fear. This was going to hurt. She patted her lap and he understood what she was going for, placing himself over her thigh, chest on the bed. It took some sorting to get his legs into the right position but eventually she placed him over one inner thigh, using the other to pin him into place. He could feel the radiant heat of her sex against his hip and he was suddenly and keenly aware she was not wearing any panties. Fucking hell, how did Jack land in this situation? He wasn’t sure yet if he should thank him or be furious about it. He consented, he reminded himself, tasting regret in that thought for the first time. No matter how much he enjoyed them, there was no doubt that spankings hurt and the plan here was to roast the hell out of him. Fucking Jack. 

Then it began. The first crack made him jump. It had been so long since he had been given this kind of classic discipline that it startled him. He tasted the difference from memory instantly. Her hand was firm and Mistress Lily’s words were true - they were respectable girls and clearly well trained. He groaned softly as she adjusted slightly, rubbing his red bottom with a firm hand. “How are you feeling now?”

“Oh god, it has been so long, Mistress.”

“I know, I know… still a long way to go.” 

“Yes Mistress.” 

A drawer opened and then closed with a sharp snap. He was expecting it and yet not all at the same time. Harmony was a ruthless little Mistress as she applied the paddle with efficiency. He flinched and moaned, unable to help his shifting body, grinding against her thigh. His cock was hard already and he couldn’t help that, not with her heat pressing against him. His hands pressed to his face and she stopped.

“No. Do not cover your face. Hands down now, turn your head toward me. Do that again and I will cage your cock before I continue. Do you understand me?”

The shame had a taste, a cruel bite that danced over his tongue and filled his mouth. “Mistress. I am sorry.” he pleaded as he moved his hands down, fisting in the bedding as he tried to steady his own breathing. 

Harmony sat up and nodded, “Up onto the bed fully Mark.” 

He did, letting her shift the pillows out of the way so that his face would always be turned toward her. She set up her phone, into a little stand and he knew exactly what she was doing. “Just for you Mistress?” he asked quietly.

“And the girls, and no, I will not post it. I promise. I am a respectable girl.” she assured him, stroking his back gently. “But you don’t mind if I show the girls, right?” 

He shivered as he replied, “No Mistress. You can show the other Mistresses if it pleases you.” 

“Good boy.” 

Oh it had been too long since he had been told that, praised sincerely, and he felt himself melt into the bed, his mind, once so busy, settled into a quiet calm. She circled the bed, and touched his cheek. “Look at the camera baby.” Her voice was a dulcet whisper and he could deny her nothing. 

He gave a shout when the strap came down, thin and vicious, leaving a white stripe across his ass before brightening to a livid red. He stopped counting at 20, letting himself just feel it as the flickering flame in his skin became an inferno. Tears pricked his eyes and his breath came in soft sobs. Finally she set down the strap and lay next to him on the bed. “Look at the camera, my good boy. Let them see your tears. Let them see what a beautiful man you are.” Her hand stroked his back, slow and gentle. His mind settled, content in the moment. 

Her hand cracked on his ass, just a simple hand spanking but after the vicious bite of the strap, it felt intense and intimate. He could feel only her, on this bed, that smelled like her, her body against his side, her skin caressing his between spanks. At some point, he didn’t know when, didn’t feel the transition moment, her hand became the paddle, rougher, cruel, making his ass bounce, lifting him, driving the bruises deep. He gave in to full sobs now, just let it all go. 

When it stopped, she stayed with him for a long while, stroking his skin gently, caressing him. The bed shifted, moved and he heard the door click open and then close again. He waited, trying to pull himself together, hoping that she was not angry with him. Mark’s mind was starting to spin when she returned. “So sorry, Mark, I should have thought ahead. I will be more thoughtful next time.” She held the cup to his lips and he sipped, letting cool water restore some of his lost fluid. A cloth, damp, stroked over his heated skin. He felt better, soothed and content as her arms slid around him. He shifted over her body and he realised she was nude, her body firm and perfect beneath him. 

Her hand wrapped around his cock and she directed him into her core. He gratefully sank into her pussy. Filling her slowly, savouring the press of her pussy, that tight wet heat around him as he fucked into her. “Thank you, Mistress. Thank you.” he whispered, just as her lips found his. 

He was bad, so very bad, but he couldn’t help himself - not after being teased and punished, not after it had been so long. He came, jerking into her body hard as he did so. 

“I’m sorry.” he muttered as he wrapped his arms around her shoulders, pressing his body to hers. Her hand met his ass again in a sharp crack and he jerked against her. “Mistress.” he whined.

Her hand pressed on his shoulder and she whispered, “Finish me. Now.”

The relief at the clear instruction made him lightheaded. He shifted down her body, beard brushing against her soft curves. She was so fit and yet still so silky and delicious against him. He didn’t deserve this, it was too much, how did he get this lucky, he’d have to thank Jack profusely later, he thought as he guided her thighs around his shoulders. His tongue lapped at the mess he had made of her, tasting himself and her. 

~ 

The exhaustion was evident in the droop of her shoulders and the way she curled herself around his warmth. The man had managed to deliver two orgasms after she applied her belt to the curve of his incredibly well roasted ass. He took it though, not using his safeword one time. She suspected he knew he needed it, no matter how much it hurt. He was so well-behaved that she allowed him to suckle at her breast again as he nodded off, his tear stained cheeks leaving little trails of dampness on her skin. Her hand curled around his cock, stroking lightly. Sex with men did almost nothing for her so she didn’t let him fuck her or cum. That was pointless in her opinion. But she did like playing with his body, liked how even in his sleep it became hard and he whimpered just a little. 

When she woke, he was soft under her hand, his expression so smooth and clear that she assumed he was asleep. That was until she lifted her head and he opened his eyes. “Good morning, Mistress.”

Lily propped herself up on one elbow, hand on her cheek as she used her other hand to toy with his soft appendage, rapidly becoming hard again. His eyes grew unfocussed but he didn’t move. She glanced over his shoulder to note it was barely 7:00. She should get up and have a run before the day got hot but she couldn’t bring herself to move just yet. 

“Good morning, Jack. How are you feeling today?”

“Sore,” he laughed out, “But good. Content. Thank you for…educating me.”

Lily grinned before leaning in to press a kiss to his shoulder. “Go on. Go make us breakfast and coffee and all that good stuff.”

“Yes, Mistress.” he replied as he crept from the bed and she rather missed the feeling of his cock in her hand. Weird. Men were so gross. She would have to change her bedsheets after he made them icky with his man-ness. So why did she want to call him back, bend him over and make him sob again? Why was he so delightful now that he was finally obedient? Was it his earlier disobedience that sparked this fire in her to make him pay and pay or the fact that he now seemed to have settled into the role as their literal whipping boy? Hard to say. Either way, it was going to be a fun day. 

She slipped from the bed and managed to use the washroom quickly before any of the others were awake. She pulled on her running bra and shorts followed by her favourite outdoor runners. With her earbuds in and her phone strapped to her upper arm, Lily made her way out of the gorgeous cottage and hit the trails. The scenery was incredible and she felt every single one of her worries simply float away as she pushed through the terrain. She didn’t push herself particularly hard and after a week, she already had her timing down. 

The house was just coming alive when she entered again. There was a waft of baking and coffee as she padded through the house, runners by the door so she could clean them later. By some miracle, she snagged the downstairs shower with all its jets and the better water pressure. Still, there were currently eight people in the cottage so she didn’t take her sweet time. 

Pulling the towel around herself, Lily dumped her running gear into the laundry hamper and headed back up the stairs. Jane walked past her, feet bouncing on the stairs as she went down. “Looking good, Lily. Shall we take the kayaks out later?”

“Definitely, Jane. Maybe you’ll finally beat me.”

“Does everything have to be a competition?”

Lily laughed, “Like you aren’t planning it already?”

“You know me far too well!”

She pulled on her bikini again with a pair of jean shorts. After brushing out and braiding her hair, Lily applied a little moisturiser to her limbs and face. Once she was satisfied, she headed back to the kitchen. Jane and Risa were at the table with a calendar page for the month in front of them and little slips of paper with their names on them. “Oh good, glad you are here, Lil… come see.” Harmony exclaimed as she wandered from the kitchen area, a coffee in hand.

“What’s up?” 

“So this is names jar…” Harmony tapped on a floral jar. It was obviously for decorative purposes. “So first I wrote our names here on day one, and counted out to fill in our other dates for each and then I halved us again for the other male, see.”

“Okay that’s cool. Every three days each of us gets to be primary. Love that…” Lily nodded, agreeing with the system Harmony proposed. “So draw names and you do the same math for everyone else.” 

Risa nodded, “Got it in one. Except I think we make Jack pull his first name and then Mark can do the same and we can organise from there. Each selecting who will be their primary until we have it all labelled out.” Jane finished writing out names on slips of paper and tossed them into the jar, shaking them around. 

“Jack! Mark!” 

“Ugh why are we yelling this early in the morning.” Elena grumbled as she stumbled down the stairs. She was still in her nightie, a frothy concoction worn over a matching set of panties. Elena had many delightful qualities in Lily’s opinion. She adored the woman’s kindness and intelligence and she had to admit her beauty was nothing to shake a stick at either. However, she was absolutely not a morning person.

“We are organising who is in charge of the men today.”

“Fine.” Elena pouted as she plunked herself into a seat. Before either of them could say much further, the two men came into the dining area and laid out two laden trays. There were muffins and scones, still warm from the oven as well as sliced fruit on Jack’s tray while Mark was carrying coffee. 

“Oh that’s better,” Lily affirmed and Elena was in clear agreement as the men poured and dressed their coffee as each woman directed. By the time each of the girls was at the table, all but Elena dressed for the day and ready to play. Harmony picked up the jar and held it up to Jack.

“Take a name.” she ordered crisply. Jack paled and glanced over at Lily. She nodded encouragingly, understanding his apprehension but knowing it was time for the other girls to get a real chance to play with him. He reached into the jar and withdrew a name. Mark did the same, his cheeks as flushed as Jack’s were pale. 

“Jack first!” Risa ordered and he looked down. 

His breath came in a shuddering sigh as he read, “Mistress Emily.” 

“Oh brilliant.” Harmony nodded and Jane immediately started to fill in the calendar, showing where Emily would get the chance to play with each of the men. Emily smirked over the coffee, her eyes flicking to Jack’s face and back down again. “Now Mark.”

His throat cleared as he read, “Mistress Risa.”

The calendar was filled in again. “Okay, I just need our Jack to pull one more name and then everyone can be jotted in. 

Lily watched as both men flushed and then watched as he pulled out another name, “Mistress Elena.” Harmony completed the calendar and then smiled. 

“Oh look at that. Jane you are jotted in now on all the missing slots. We are all set. It actually works out perfectly evenly, assuming we leave on time. When does your next booking start, Jack?”

The man cleared his throat and shifted uncomfortably, “There isn’t one until September. I wasn’t supposed to…this was a favour.” he started explaining. 

Lily took a sip of her coffee before setting down her cup and reaching for a scone and the butter. “Well no wonder you were so confused at first. If you didn’t even expect to have us.”

“I am better now.” he replied stoutly. Lily watched as Emily circled around, her arms coming up to slide around his shoulders. 

“You are,” Emily whispered, “You are so good. Do you have more to do in the kitchen?”

“Only if someone has another request, Mistress Emily?” he replied and Emily folded her hand into his and tugged him over to her seat. A spiral of something akin to anger flooded through Lily’s veins. She wasn’t jealous, was she? He was a man. She didn’t even like men. They deserved every punishment she gave them.

~

Her hand folded over his as they walked. It had been a week now and this handsome older man had been treated to discipline each and every day since as well as lots of teasing. He served well. Mark was serving well. Lily gave Jack’s hand a gentle squeeze and savoured the moment. The weather had cooled over the last few days but was supposed to be back to hot soon enough. Last night there was such a wild storm that Jack asked permission to go check on his little cabin this morning. She offered to come with him. The ground was muddy but the air smelled fresh. She always enjoyed a walk after a storm. 

“Thank you for coming with me today, Mistress Lily.”

Lily laughed, shaking her head such that her hair shimmered around her shoulders. She had left it down today and savoured the silkiness against her bare shoulders above her tube top - the same one she had been wearing two weeks ago when they arrived. “I like having you to myself for a little while.”

“I think you are flattering me.” he replied quietly, humour threading his words. 

“Not at all, Jack. Well, maybe a little, because I have gotten time with you but I was a little envious of the others applying your discipline. I wanted to do it. I don’t even completely understand it. I don’t usually…I’m not…” Lily paused and then continued, “I’ve disciplined many men of course, it is expected of any woman of reputation. But there was something about you, about this situation. I…I think I’ve grown a little attached.” She could see the cabin looming ahead and she felt a spiral of anticipation. 

“Do you think, after this vacation is over, for you, you could visit me sometimes, some… before you, before this, I haven’t had this in so long, Mistress, I know it probably seems ridiculous to you, but if, every once in a while, you’d be willing, I’d be so grateful.” 

Lily tightened her hand in his and nodded, “We can work something out, Jack. I promise.”

“Thank you, Mistress.” His gratitude was a physical entity that washed over her in a wave and she savoured that sensation, let it slake her, satisfy her. “Excuse me.” he continued, reluctantly releasing her hand to circle the little cabin. 

Lily entered the code she had for the main cabin into the door key pad and to her pleasure, it opened. This cabin was smaller. Only a main room, loft and small washroom. It was a little dusty after Jack had been at the main cabin for the last week but it was clearly usually kept very orderly. Dishes were stacked neatly on the open shelves. The wooden table was polished to a shine. She poked her head into the washroom and while small, it was well appointed and quite pretty. There were central beams to allow the ceiling to feel higher and a small staircase up to the loft on the second level. She wandered up to find a surprisingly large bed set on a low platform underneath a bright window, casting sunshine over the bed, even on this greyish sort of day. Lily opened a series of drawers until she found what she was looking for and carried her find back down the stairs. She set it on the small dining table, built for two. 

Stepping outside again, it only took her a few minutes to find what she needed and return to the interior. Her shoes were left by the door and she sat at the table, using a sharp utility blade to strip the thin branch. Jack stepped inside and toed off his shoes before stopping at the sight. “Mistress?” he whispered.

“Yes, Jack?” she returned, her smile a slow, wicked thing. 

“Please?”

“Finish up what you need to do Jack and then find a rope long enough to go over that beam please.” She instructed firmly, gesturing above her head. Jack trembled but he nodded.

“Yes Mistress.”

“Good boy.” 

She wasn’t sure if he took his time or if the chores really did take him another hour but soon the small cabin smelled of lemon scented cleaner and furniture polish. He tossed the rope over the beam and then waited, standing next to it, eyeing it like it was a snake about to bite him. He was right to be apprehensive. She was very well trained after all. This was going to hurt.

Lily set down the branch, now rid of its bark, next to Jack’s thick belt and a wooden spoon. Jack did not keep a lot of implements in his cabin but Lily was creative and knew how to improvise. Jack waited patiently for his instructions, keeping his gaze on her. 

She rose to her feet, slow and graceful. Her shorts hung low on her hips and her tube top showed off the curve of her breasts. Jack’s eyes clung to her skin, tighter than her clothing. She circled him, hands brushing over him, feeling the warmth of his skin through his t-shirt, caressing his arm as she moved around to the front again. He had gotten used to his spankings, no longer moving like he was wincing in agony. She was about to change that and they both knew it. 

“Stoplight system, right?” she murmured.

He shuddered and nodded, “Yes, Mistress.”

“Take off your clothing, Jack and come stand, right here.” Lily directed to the spot just below rope ends that hung over the beam. He didn’t hesitate, although she could feel his apprehension. Once he was nude and in position, she wove the rope around one wrist and down to his ankle before leaving the end on the floor. She then did the same with his other arm and ankle, forcing them apart, holding them in position. “Good boy. How do you feel? Try to move.”

He wiggled and tugged and then let out a soft groan, “It is secure, Mistress. I can’t move.”

“Good.” Her hands slid over him. His ass was bruised and a little pink but not nearly the colour it was after their first session together. “I love how perfect your skin colours, it gets all mottled and red and purple. So pretty.” 

“Thank you, Mistress.” He whispered, a soft choking sound, “Please will you….”

“Will I what?”

“Discipline me… I want…I need it.”

“I know, darling man, I know. You’ve needed this for so long, haven’t you? And you’ve been so alone.”

His chest lifted, heaved and then he nodded in his restraints, tugging on them lightly but finding himself still bound, “Yes, Mistress. I only have two weeks left. I wasted one already… being so stupid.”

“Shhhh… no. none of that. You were already forgiven, you didn’t know. Shhhh… no need for punishment. This is about my pleasure. Do you understand?”

“Yes, oh god yes please Mistress.”

Lily reached down and picked up the switch she had just carved. It was a light, whippy sort of implement, designed to sting and create delightful stripes. She brought it down swiftly, marking him. Her energy was high but she was well trained. The stripes lined him. Upper shoulders, over the rump of his sweet sore ass and down his legs. Careful careful around all those delicate spots like his knees and lower back. She knew what she was doing after all and she wouldn’t fail herself by getting too carried away. She worked him thoroughly and by the time she set it down, he was groaning, tears pouring down his cheeks and still she picked up the wooden spoon. A smaller implement, she pressed in close, let him feel her body, pushed down her top, just a little, so he could see the dusky pink of her nipple. His tongue lolled out slightly, unconsciously, as if willing her body to get that much closer so he could lick, suck on it. But she was too short to facilitate such a move. 

Still, with her body pressed to his, she began to spank his tender skin with the harsh little spoon, over his ass, between his spread thighs and along the front of them. He groaned and flinched and hissed between his teeth. He sobbed when she applied a dozen strokes along one inner thigh to then mirror it along the other. He writhed, his cock now straining, dripping mess onto his formerly clean floors.

Finally she picked up the belt and he jerked in his bindings again, “Please Mistress,” he begged.

“Do you need to use your safeword, Jack?” she offered quietly.

“Please… please please.” he begged. It wasn’t his safeword, and as much as she did like him, he was still just a man. So she folded the belt, careful to control the buckle and stepped back enough to get a good swing in the smallish space. He howled as it cracked down. She paused between each blow, listening to his mumbled pleas and hoarse shouts but no form of his safeword was uttered. So she continued until she felt sweaty, hot and finally a bit tired. Only then did she toss down the belt.

She reached for the end of the rope and gave it a tug. She knew her ties and it unwound swiftly. The other side released just as quickly, allowing her to wrap her arms around the sobbing and now freed man. She guided him up the stairs and let him collapse onto the bed. She stripped and then began to wash down the man, as praise dripped from her lips. “Good boy. Such a good boy. You knew how to be so good. So lovely. So perfect. I am so happy with you, my darling boy. Come, let me give you sweet kisses.”

Her lips found his, dusting those offered kisses against the panting lips of the sobbing man. He was a mess, clinging to her, holding her close. His mouth trailed downward and latched on one breast. “That’s right,” she praised, settling on the man’s bed comfortably and let Jack suck on her breast, a fierce, desperate sort of suckling that gradually calmed.

His senses returned slowly and he rolled her onto her back. She allowed it because he was still soft and pliant with her caresses. “That’s right, see, my good boy.” she murmured, tracing fingertips over the man’s cheekbone and along his jaw.

“Mistress? May I lick you please?”

“A fitting reward for a good boy, yes?” Lily teased but Jack’s responding nod was endearingly earnest. “Okay, Jack. You can, let me get comfortable.” Lily shifted upward, letting her back rest on the slightly padded headboard, her face upturned to the early afternoons sunshine. She adjusted one of the pillows and then sighed in pleasure at the comfortable position. Jack didn’t need telling twice, he curled around her hips and abdomen, exerting his energy to lick her pussy, suck on her clit and kiss along her thighs. She let him. She let his tears mingle with the juices flowing from her core, let him savour her. At one point she dozed, almost asleep but not quite. She enjoyed the filtered sun on her skin, the replete sort of exhaustion of her limbs and the gentle, eager motion of Jack’s tongue. He was not wearing out in his task and she was starting to suspect he’d dipped further into his submission. She had no reason to be bothered by it. It wasn’t even mid afternoon yet so the man had much ahead of him still - pleasures and pains. 

Lily sighed as another personal discomfort made itself known. Damn and she was just comfortable too. Her hand traced over his dark hair, toying with the soft curls for a minute before sighing, “My darling man, I must go to the washroom.” 

Jack didn’t move away. Instead he pressed closer, his mouth sealing over her core, tongue probing. Lily let out a soft groan and continued warningly, “Jack. Jack, if you don’t move soon….”

He didn’t move away, if anything he was now pressed firmly against her, his tongue still working over her pussy. “Fuck.” she growled, “Jack. I’m going to…” As if she couldn’t stop herself, she released a squirt, promptly clamping down her muscles to prevent herself from literally pissing on Jack’s bed. He swallowed it, greedily drinking her delivered fluid down, his tongue washing over the entrance as if trying to lure out more. So she gave it to him, her eyes flashing to his as he looked up the length of her torso to meet her eyes. 

Her hand folded over his as her other hand buried itself in his hair. She let it trickle out and he swallowed it, all of it, taking everything she had and as she lay there gasping at the intensity of feeding this man her piss, he proceeded to continue licking her out. She came, a flinching grind against his face, coating it in her pussy fluid. She collapsed onto the bed, shocked, amazed, turned on and slightly horrified all at once. Jack stayed between her thighs for some time, slow languid licks until finally his cheek settled on one thigh. His breath tickled her wet folds.

“Jack?” she finally whispered.

“Yes, Mistress.”

“You drank my piss.”

“Yes, Mistress.”

She sat up, looking down at him as she did so, the way he had curled his sore body onto the bed so he could lay so perfectly between her thighs. His body looked violently sore and brutalised. His cock, still mostly hard and largely ignored, lay between his thighs, thick and heavy. 

Her hand stroked his face. He hadn’t allowed a drop of piss to escape. His face was still a little shiny from her pussy. “I … I feel like I should be ashamed but I have honestly never loved anything more in my life. Have you done that before?”

“No, Mistress. But I would, I would do it again if you wished, if you would let me. I loved it too. I love serving you. It is the most complete I have ever felt.” 

She frowned and shook her head, “But I am so cruel to you. The other girls let you cum, let you have some of your own pleasure too, but I will never want your cock in me.”

“Perhaps you can share me sometimes with someone who will allow me such a reward. But I live for your cruel hand, for the way you touch me, even when I know you will allow me no release.”

Lily let herself collapse back onto the bed, “This can’t end in another week or two or even this summer. This is…this is…you are mine. Make an appointment with your doctor. I want to meet with her to discuss the impact of this on your health before we commit to anything.”

Jack nodded, applying another series of soft licks to her pussy before stretching up enough to lay claim to her breast. She ran her hand up and down his back as he replied, “I …I have a new doctor. I don’t like her. She wants me to do a full physical and…”

“Jack, was it a question or an order?”

He paused before replying in a low whisper, “Order, Mistress.”

“So what will you do?”

“Make an appointment with my doctor.”

“One I can attend.”

His sucks on her breast became fierce, pulling roughly. Funny how she could lash him brutally, drive him deep into submission, piss into his mouth after he delightfully made her cum, and then he would make a fuss about a doctor’s appointment. She remembered suddenly that in this territory, they strongly recommended cages for any unclaimed male over 40 and she knew then why he was being silly about the appointment. “Jack?” she stated, her tone full of authority once again.

“I will make an appointment with my doctor, one you are available to attend, Mistress.” He replied, letting his cheek nestle into her breasts. “And even if that doctor says it is no good, I still want to.”

“We’ll see, my lovely man. We’ll see.” 

~ 

She had left work at lunch hour and made it to the cottage just in time to collect the man. Jack had walked down to the end of the drive, waiting there in the jeans and henley she told him to wear. That thick belt was at his waist and soon enough that leather would taste his skin again. She had packed a few extra implements as well. The vacation had ended two weeks ago and she hadn’t seen him since then. Mark, Lily knew, was travelling every weekend to see Jane and Emily, both of whom had taken a particular interest in the man. Jack, however, had been working hard on his property, getting it ready for the upcoming September wedding. 

She missed him. 

She had never missed a man before in her life. She doubted herself nearly constantly since leaving the cottage but seeing him standing there, waiting for her, she felt a rush of such intense pleasure and possessiveness that it took her breath away. Jack tugged open the passenger side door and seated himself, buckling in carefully. His hands were shaking slightly and Lily found it absolutely endearing. 

“All set?” she asked.

He nodded, “Yes, Mistress, I am just nervous. I don’t like doctor’s appointments that much. I’m glad you’re here.”

“We’ll get through this together and then you and I can have a nice weekend. Well…” Lily continued as she pulled the car back onto the road and turned the vehicle toward the small town where the doctor’s office was located, “I’m going to have a nice weekend. You are going to be…”

“In heaven, Mistress?” Jack teased, laughing as he did so.

Lily grinned and reached over to cup Jack’s cock through his jeans, giving it a light squeeze. “We’ll go for a nice swim after your punishment, you can rub on my sunscreen and then I’ll return the favour.” His cock jerked and his body shuddered. His reactions were so visceral that they sent a shiver of pleasure through her.

“And you will use me for your relief, please, no matter what…”

“This weekend, yes but after that, we’ll see what the doctor says.”

“Oh please…”

“Enough Jack.” she scolded with a sharp snap and felt his cock jerk again. This man loved her cruelty almost as much as he enjoyed her generosity, perhaps more. She smiled at him as the car ate up the distance. “We were fortunate the doctor was able to fit you in for an end of day appointment.”

Jack nodded, his hand curling around her wrist, not to control but to caress the silk of her skin, a light golden colour after her vacation that had yet to fade now that she was back to work. “They were accommodating once I explained a lady was accompanying me and wanted to be present. They said it was best for…” 

His voice trailed away and Lily gave his cock a hard squeeze, making him gasp softly. “It is best. You know that, Jack. You’ve needed a stern hand for a long time and you should be grateful I am willing to provide it.”

“I am, I promise, Mistress. It’s just a big change for me.”

Lily’s temper softened and she used her thumb to caress his cock through the denim in gentle empathy. The town was small and it didn’t take her long to pick her way through it to find the doctor’s office, a pretty little building with an impressive garden out front. There was only one other vehicle there, a smallish SUV that looked a little out of date and splashed with mud on one side. The door opened as she approached and an older woman greeted them brightly. 

“As soon as I have you checked in properly,” the woman explained, “I am heading home for the day. The doctor will be right along.”

“Thank you so much for accommodating such a late appointment. I really appreciate it.” Lily replied, smiling broadly. 

The clerk smiled in response, expression warming to Lily’s good manners. “We are always happy to go above and beyond for our patients. Now please, come to my desk and then I’ll put you both in the patient room. The doctor will be in shortly, she’s just finishing up her notes. She’s an absolute stickler for getting them done straight away.”

“A good practice,” Lily affirmed with a nod. The questions the clerk had were brief and Jack had the answers easily at hand. It was also abundantly clear he hadn’t been in for a proper check up in quite a while. She sparkled with irritation at his lax behaviour but in truth knew she was seeking excuses when she needed none. He was getting a thorough session later regardless. 

“All right, Mr. Sampson,” The clerk stated politely, “In you go. Strip off completely. We don’t bother with gowns for males as a rule but there is a blanket at the end of the exam table if you’re feeling modest, or chilled.” She tittered in amusement at her own words and smiled at them both. “I’m locking the front door behind me but the doctor will let you out after the appointment. I understand it is a full physical so it might be a bit.”

“Thank you for all your help.” Jack replied politely and the woman beamed at his good manners, closing the door behind herself as she left.

Jack paused for a moment once they were left alone and Lily nodded at him. “If you pick up that blanket for anything other than moving it out of the way, the first thing your doctor will see is me beating your ass. Strip Jack and don’t even pretend modesty.”

His cheeks flamed such a bright colour that it trailed along his neck and up to his forehead. It was honestly so endearing to see him blush like that. He stripped hastily while Lily looked around the room, checking out the posters. When he was bare, she noted his ass and thighs had faded to a dull yellow and otherwise he was substantially healed from his three weeks of continuous correction. The sight filled her with inexpressible anger. It was so wrong to see him return to such an unmarked state. 

“Oh Jack.” 

He looked down and sighed, “I know. It feels wrong to me too, Mistress. But it makes it a good canvas for your handiwork later.”

She laughed, softening instantly at his quip, “That it does.”

The door pushed open and she heard a bright voice say “Knock, knock.” Almost all physicians were women but Lily wasn’t expecting this beauty. Now she wished she had dressed better than her shorts and sleeveless blouse. 

Jack’s face was red again, his hands flexing as he resisted the urge to cover up, “Hello Doctor Greer.”

“Jack Sampson! I am so pleased you finally made an appointment.”

Lily was struggling with getting enough oxygen as this bright eyed blonde turned to look at her. Jack replied as Lily tried to remember how to process words, “Doctor Greer, please meet Lily Woods. She’s been…assisting me lately.”

“With correction?” the doctor replied, making a small note on her ipad screen with one of those apple pencils. The gesture had Lily’s gaze drift downward, where she noted the impressive curve of the woman’s breasts. 

Lily swallowed hard and then finally spoke, “It is nice to meet you, Doctor. I met Jack a few weeks ago when we rented his cottage. Some things came up and I wanted to ensure he had a proper medical appointment.”

“I see. Would you mind stepping out for just a minute? I need to ask Jack a few questions.” the doctor turned those bright blue eyes to the man, obviously expecting Lily’s compliance. Unable to stop herself from doing just that, she nodded.

“Of course. Be good Jack.” Lily replied as she collected her purse and stepped out of the examination room and into the hallway. A few minutes later, the door opened and the Doctor smiled at her.

“He confirmed that you are entitled to all information, be present and provide instructions. Also, he signed the forms that indicated your instructions would take precedence over his own, with a few limited exceptions of course. Please come in, Lily. Is it alright if I call you Lily?”

“Oh yes, I mean, sure, I don’t mind.”

“Feel free to call me Cristiana. After all, he is my patient but you are not. But I am also comfortable if you prefer to remain more formal.” Cristiana continued, holding the door so that Lily could re-enter the room. Their bodies brushed past one another and the electricity danced between them, making Lily’s skin sparkle.

“Alright, let’s begin.” Cristiana reached into the pocket of her crisp white lab coat and withdrew a pair of gloves. She slid them on with that snap and crinkle that only medical gloves ever seemed to make. “Now I am quite thorough when giving a full exam so please let me know if you have any questions.” 

Cristiana picked up one of Jack’s hands. “Try to stay relaxed,” she continued as she glided her hands over his skin, feeling his muscle and curling and pulling straight his fingers before moving up his arm. “Any pain in your joints?”

“Umm, not usually. Sometimes after a punishment.” 

“Good good. At his age, I don’t recommend he is bound in a single position for longer than two hours. Too hard on the joints.” She pushed up Jack’s arm and palpated under his armpit, feeling for something that had Lily watching in fascination. “Generally, these bursts of extreme punishments followed by nothing are not ideal but I recognise that sometimes it can’t be avoided.”

“Daily is my preference too and Jack takes it well. But work…” Lily made a face. 

Cristiana laughed, “I know exactly what you mean. It is hard to find a balance, especially when a dynamic is new.” Her fingers pressed into his throat, feeling for something before continuing downward. “Remember at any age, motion is lotion, but most especially at your age. Do you understand?”

“Yes, Mistress… I mean, umm Doctor Cristiana, Doctor Greer.”

Cristiana laughed delightedly, “Shhh, no need for stumbles. I don’t mind any version of the title, as long as you give me one. Now lay down on the examination table, feet into the stirrups.”

Jack’s gaze flashed up to Lily’s. She nodded encouragingly and he let out a breath before complying with the physician's instructions. Cristiana looked over at Lily as he settled into place. The doctor attached the velcro over his ankles, pinning them into the stirrups. Jack released a soft noise, akin to a sob. Lily folded her hand over his and he clung just as Cristiana nudged the stirrups further apart and shifted to stand between his spread legs. It reminded Lily of the diaper position, one she had yet to thrash Jack in if she remembered correctly. She’d have to do that soonish. It was so humiliating and would allow her to really crack down on some sensitive spots. 

“Wow, he got hard fast.” Cristiana commented and Lily followed the other woman’s gaze to the thick erection laying over his abdomen and along his thigh. 

“I don’t let him cum usually. I just like playing with it a little.”

More than a little but Lily kept that thought to herself, not wanting Cristiana to think she was a monster to the poor man. “Do others allow him to cum or does he have a weekly masturbation session?” she proposed and Lily bristled instantly. 

“He isn’t allowed to touch himself for anything other than cleaning or dressing. When my friends were here, they let him cum. Some of them enjoy the feeling of a man’s cock in their pussy or mouth.” Lily made a face, grimacing at the idea. Cristiana laughed, soft and delighted, making Lily grin unconsciously. She watched as the woman’s gloved hand stroked Jack’s thick erection.

“Poor boy. Your primary mistress has no real appreciation for your pretty cock.” she teased and Jack’s chest heaved, one hand coming up to wipe away his tears. Then Cristiana turned those pretty blue eyes back to Lily and smiled, “Then I am going to strongly recommend you consider caging him. The law right now says age 50 but there has been a big push to lower it and I think it is likely going to become the legal standard shortly.”

“What kind of cage?”

“For him, I would suggest a full immersion, solid base, the toggles to hold in place and then the magnetic latches so that when you unlock it, all of it is quite easily removed but when in place, it keeps the entire package in a good position.” Cristiana stated firmly, running her fingertips along the shaft, “You could even do the bubble trails along the head and down the length so that if he is ever given permission to penetrate, it feels quite… quite painful.” 

“I like playing with it though. I don’t let him cum but I do like the feel of him available to me to touch, to hurt.” Lily explained. 

“Oh well, then you could leave him free at home. After the week to ten days of healing time post caging, it can be removed and put back frequently, even daily.”

“So he could be caged off the property and kept uncaged on?” 

Cristiana nodded, blonde hair bouncing, “It is how my mother has kept my father since their wedding night. He loathes it but every year she upgrades it and every year he accepts it. I strongly recommend it to encourage true obedience. I don’t think too much freedom for a man is healthy”

“No, no… please.” Jack whispered, tears in his voice, as he interjected. He was shaking with distress. 

“Excuse me. I need to comfort him a little to settle him.” 

“That’s fine. I’m going to set up for his probe.” 

Lily wasn’t quite sure what that meant but her attention was now on Jack. He reached for her as she approached. “Please, I don’t want…” 

She unbuttoned her blouse and leaned forward, letting Jack latch. It was harder than usual, making Lily groan slightly. Gradually he settled. Lily pulled back, forcing him to release as her hands rose to stroke his cheeks and along his chin. “We will talk more. I won’t decide today because I want to look into this more and talk to your doctor a little. We have other more pressing concerns, right now, my lovely man. Settle.”

“Yes Mistress. Thank you. Is Mistress Cristiana….” 

“I’m ready to begin. Lily, would you like to observe or stay up there with him? Does he need to be gagged?” The doctor questioned. 

“He’s fine, aren’t you? No gags needed.”

“I’ll be good, Mistress. I promise.” Jack pledged and Lily’s heart softened at his earnest plea. She leaned in to press a soft kiss to his lips. 

“That’s my good boy. Be good. Lots of ouches ahead, right?”

He laughed quietly, soft and watery, and nodded, “Yes, Mistress.”

She kept her hand in his and shifted down to watch as Cristiana lifted a thin shaft. “We’ve recently started using this to facilitate the probe. I’d like your consent to insert it.” 

Lily looked it over, noted the wide base and the pull string before nodding. “Go ahead.” Jack’s hand squeezed in hers but she didn’t consult with him or look at his face again. Cristiana applied some lubricant to the shaft and then pressed the head to Jack’s rear entrance. He let out a soft gasp as it filled him slowly. Then she set the base into place. “Good boy.” Cristiana praised, running a free hand along his inner thigh. “Now we inflate.”

Jack whimpered and Lily had to admit, it was riveting. “How big will you go?”

“It can go as wide as 12 centimetres but generally speaking I only need around five or so to get the probe in and have a look.”

Lily nodded, “Take it to seven, maybe eight. You need the room to work.”

Cristiana’s smile was broad, “Thank you, that will make my job easier. It is disposable so you can keep it in for the ride home. Don’t let him sleep in it though.”

“Will it last through a whipping?”

“Of course. I have done it frequently.” 

Lily nodded, “Your male must be so spoiled with all these toys at your disposal.” 

“Oh I don’t have one right now. Work is so busy and this town is so, so small.” Cristiana commented blithely as she continued to fill the inserted stretcher. Jack’s chest heaved and his thighs trembled. Cristiana stroked one with her free hand while Lily pet the other.

“Maybe you’d like to come out to the cottage, have dinner with us one night. He’s a good cook. You … you could tell me more about the cage options.”

Jack’s hips lifted and then settled, “Please.” he whispered.

“Almost there, Jack. We’re just over three centimetres now. It’ll be just a little longer. Hold still.” Cristiana said, her voice jolly and reassuring.

“I can’t…It’s too much. I can’t. Please Mistress.”

Lily reached out to touch his cheek. “Yes you can. Deep breath, let it out.”

She watched as Cristiana removed an incredibly thin wand from its packaging and applied a little lube to it. “How does that go in?” 

“Well you see there is a hole right here, when it inflates, allowing me to insert the wand. We’ll turn on the camera, have a good look and make sure he is healthy.” 

Jack shuddered as Cristiana explained but Lily could see the drip leaking from the man’s cock, indicating he was not nearly as disturbed by that as he was pretending. Cristiana turned on a small panel and shifted the screen so Lily could also see. “And here we go.” 

It was fascinating and entirely unlike anything she had seen before. “So as you can see the covering of the insertion allows us to see the walls clearly and helps us capture the information we need.” Cristiana murmured, then she tsked slightly, “Someone has not been using enough lube when they pegged him. See… abrasions right here. That’s clearly from an inserted object given the direction of them. Do you peg him?”

Lily shrugged, “I’m going to be honest, sex with men has little interest for me. I just like his service. I like hurting him and I like toying with him. He is also good company. He does…some other things as well. I’ll let anyone to whom I lend him to know that he requires additional lubricant.” 

“Good good.” Cristiana commented, moving the wand around with smooth motions. It was so deep now she barely had her fingers on the base. Jack was groaning so Lily suspected it felt good. Finally Cristiana removed it, tucked the wand into a cleaning tray and tugged off the gloves. She pulled on a fresh pair as she rose to her feet. 

“Since you don’t allow him to masturbate and don’t like to bring him to completion yourself, do you mind if I stroke him until he releases? I’d like a sperm sample.”

Lily briefly considered granting a limited exception to her masturbation rule but quickly decided watching her humiliate Jack was an excellent idea. “If that’s necessary, I think that would be best. Exceptions confuse men.”

“I agree. We don’t want him to suddenly think that sometimes bringing himself release is acceptable or that you would do it.” 

Lily grimaced slightly and shook her head. She watched as Cristiana unbound Jack’s ankles and then had him rise to his feet. He was unsteady, shaking, and the plug in his ass had a funny little tail poking out from between his too-pale butt cheeks. It was adorable and Lily shifted closer, seating herself on the exam table. She nudged aside her blouse again to allow Jack a few moments of comfort. The pull of his lips was satisfying as always, more so with Cristiana’s warm blue eyes on her. 

“Is he good at that?” 

“He has a wonderful mouth. I don’t even mind his kisses, which I ordinarily don’t like from men. Between my legs, he is heavenly but I like it when he nurses off me. He suckles so prettily and I love how it comforts and soothes him.”

“He does seem to steady almost immediately. I have to admit it is very nice to see such a well trained man. I see them very rarely.” 

“He settled beautifully and now when I am away, I miss him. I miss the sound of his tears and the way he admires my body, almost as much as I miss the workout I get when I give him a good going over.” Lily affirmed and then met Cristiana’s gaze. “Would you like to let him have a suckle? It really is quite nice.”

“Let’s….let’s get his sample first.” Cristiana murmured, clearly tempted by Lily’s proposal. She wrapped her hand around his length as the other held a small container. The stroke was smooth and even as she was obviously experienced. Jack shook, his body clinging to Lily’s as Cristiana worked him over. Lily’s green eyes clashed with Cristiana’s bright blue gaze and Lily was struck again by the sense of connection she felt with the other woman.

Jack came with a grunted gasp and filled the jar to the point of brimming, splashing just a little onto the floor. “That’s right. Good boy. Fill it up.” Cristiana praised enthusiastically, “See how good you are. Good boy.” Jack’s legs almost gave out but as Cristiana released her hold on his shaft, Lily turned him toward her. He latched to her breast again, hot tears on his cheek. 

“Mistress.” he whined. 

“Shhh…” she consoled, “You did so well and I am so proud of you my Jack. Good boy. Mistress is so pleased with you.”

Cristiana placed the jar down on a tray, changed her gloves again and picked up another one. “Jack, do I need to hold your cock while you relieve yourself? I need a urine sample too.” 

Lily was so distracted by the Doctor’s beauty she had forgotten her primary reason for coming along with the appointment. She nudged Jack’s shoulders and directed him to the space near the sink. “May I go to the washroom, Mistress?” he asked quietly.

Cristiana responded before Lily could. “No, I must witness it. Go stand by the sink, Jack. Keep your body turned toward us and fill that jar. Do not spill any on the floor.” 

It was a miracle Jack’s face didn’t burst into flames, it was so red and Lily kissed the apple of one cheek before sending him away. She didn’t bother to adjust her blouse, liking the look in Cristiana’s eyes at her half displayed breast. 

“You said there was a specific concern you wanted to address when the appointment was booked. Well Jack said that but he said the concern was yours. I didn’t detect any underlying health issues. His complexion is good, his response times above average for his age and whining aside, he took his insertion extremely well. I’ve had men safeword at merely a couple centimetres but he took it up to a full seven and half centimetres. I’ll give him a script for blood work as a precaution but I see no reason for concern at this time.” Cristiana commented and Lily felt a rush of pleasure that her man was such a good boy. 

The tray rattled as Jack set down the now full jar. His face was burning and he was using the sink to wash his hands. Cristiana pushed herself up onto the exam table, her body brushing against Lily’s as she did so, and murmured, “Are you sure you don’t mind? It has honestly been ages for me.”

“Of course.” 

Cristiana’s fingertips flew down the front of her blouse, revealing an undergarment that almost looked like a weapon of war. She understood Cristiana was busty but now understood that she was that after making efforts to contain her assets. She released one strap with a sigh, the breast almost spilling out, the pink of her nipple a bright colour. 

Lily could barely tear her eyes away. She flicked her gaze to Jack and nodded as he waited expectantly. “Come take care of Doctor Greer, Jack. You’ve been very good and she needs it too.” 

He obviously didn’t need to be told twice. His lips grazed the skin above her pink nipple. “Thank you, Doctor Greer.” Then he latched. Cristiana’s head fell back and she gasped. 

“Oh shit, he is good at that. Good boy, Jack. Good good boy.'' The words were a husky whisper. Cristiana’s arms tightened around his shoulders, her hand in his dark hair. The cream and pink of her complexion against Jack’s darker one was an intoxicating vision. 

“He drinks my piss.” Lily blurted out and then blushed as Cristiana’s eyes turned to look at her. She didn’t push away Jack, who had firmly latched now and was intent on seeking his own comfort. “I mean, during one of his rather extreme punishments, he was in a really submissive headspace. I had to go. I told him, he latched on tighter. I thought if I gave him a bit, he’d let go, you know.”

Cristiana nodded, her eyes on Lily as the woman spoke, her hands still carding over Jack’s back and then into his curls before sliding out again. 

“He didn’t. I fed it to him. All of it. Then I did it again, and again, and… and I need to know if this is safe for him.”

“Because you don’t want to stop.” Cristiana finished.

“He doesn’t want it to stop either. He loves my cruelty.”

Cristiana’s hand shot out and caught Lily’s, holding it gently. The room fell quiet, the hum of the air-conditioner and the soft suckling noise from the man. “He deserves it and you deserve that release, especially if you’ve avoided men due to lack of sexual interest. This will bind you and hopefully your next romantic partner will be more…”

“Bi?”

Cristiana giggled. “There are lots of us out there. As for your question. I will check his sample. I will give you a prescription for him to take on days when you…supplement his thirst. It can’t be the only thing he drinks. He needs water and I suspect the occasional coffee. The meds will help his kidney and liver function with the additional processing. Will any romantic partner you have be permitted to use him as a receptacle too? Or just you?”

Lily’s tongue flicked out, dragged over pink lips and then she nodded, “It’ll depend on her. What she likes, I guess? I can share. That’s a lot for him though.”

“Your worry about his well-being is so lovely to see. You are such a good Mistress to him. Are you going to legally claim him?”

Lily nodded, “Yeah, one year trial first so I already filed the intention. He has a house in the city too, where I live but I’ve been talking with my boss about making my job remote, at least part time, so I can keep him more rural. I don’t want to share him with too many people and in the city, all the girls, well, they’ll regard his cock as a free-for-all or insist on sharing.”

She hadn’t talked to Jack about any of this of course but she knew he would do as he was told. Cristiana shifted her shirt again, reaching up to undo the clasp to allow her other breast to spill free. Jack palmed it gently and then shifted over, his hand coming up to caress the breast he had just been suckling from. 

“Are there any other health concerns?” 

“No, that was it. I’m glad there is a prescription. I’m not sure I could give it up now. I love the feeling so much.” 

Cristiana nodded, stroking the back of Jack’s head as she did so. “So dinner?”

“Tomorrow? You could come up early, for a swim. I let Jack finger me and lick me out after he applies my sunscreen but you don’t have to.”

“Oh that sounds lovely. We can milk his prostate too. I love doing that.”

Lily laughed, “I hardly ever do that. You are welcome to. Later in the evening or first thing in the morning, I let him enjoy himself by applying my body lotion.”

Cristiana swallowed, her eyes flicking down and then up, “And when he gets thirsty?”

“He’ll drink whatever we allow him to have.”

“Oh god Lily. I can honestly say I’ve never wanted anything more in my life. That’s…I’ve…this is amazing.” Cristiana shuddered, “I don’t… God, he’s so good at that.” She gestured to the man thoroughly latched to her breast and playing with the other one. Lily just smiled.

“He is. I will need that prescription though. I’d like to fill it before the pharmacy closes.”

“While they do, walk away, make them announce it, everyone will know what it is for…it’ll completely humiliate him.” Cristiana whispered. Jack jerked and the noises, wet and silky, grew louder. The physician sighed and clutched the man closer just as Lily leaned over him and kissed her lips. The kissing lasted several minutes and finally, reluctantly, Lily broke it off and sat back. Her entire body felt like it was lit on fire, sparkles in her skin. 

“Should I bring an overnight bag?” Cristiana asked.

“When do you work next?”

“Tuesday.” Cristiana replied.

“I’m here till Wednesday. You’re welcome to stay as long as you wish. I’ll write out directions to his place while you get that prescription. Jack, step back.” 

The man did so quickly but it was clear he was not thrilled at having to stop. He wanted to continue. Cristiana’s large pink nipples were darker in colour, wet and peaked. She reached up and did up her bra again, stifling those magnificent orbs. Lily looked forward to seeing them again, soon. Lily reached into her purse, pulled out a notepad and got to write, she diagrammed the road and the gate to ensure Cristiana would know where to go. The man pulled on his clothing quickly, flinching with a hiss as his jeans hit the end of the insertion. It poked awkwardly and Lily couldn’t resist patting his ass. 

“Don’t worry, my darling man. That will come out after your discipline session tonight. I just need to make sure you are appropriately grateful.”

Cristiana passed over the prescription and smiled as Lily gestured toward the man, leaned in and kissed her softly. “Until tomorrow Doc. Come up any time. I’ll be waiting and Jack will be too.”

Cristiana nodded, “To drink from me too.” 

“He’s a thirsty boy. We need to fill him up.”

The trip to the pharmacy was amusing as she made Jack pass over the prescription and the pharmacist also handed over a jumbo sized brand of specially medicated mouthwash designed to protect against ulcers and sores that arose from frequent urine consumption - that was what the label said in bright pink letters. 

She made him carry it out of the store but did not follow through on Cristiana’s teasing comment about making the announcement over the intercom. She thought about it but there were very few people around so it didn’t matter. She knew how small towns were, even if she grew up in the City. It wouldn’t take long before everyone knew the extent of his obedience. 

He sat in the car, awkward and visibly uncomfortable as Lily picked her way through the streets of the small town and finally turned onto the highway home. “Thank you for coming with me today, Mistress.”

“I can see why a full physical is challenging for you, Jack. I will come every time from now on. Even if Cristiana is not your doctor.”

“You like her.” It wasn’t a question.

Lily nodded, “I can honestly say I haven’t been this attracted to another person in years.”

“Do you think sometimes she’d let me come into town and bring her lunch?”

Her smile was soft, able to picture Jack doing just that. “And have a suck? On those incredible tits?” she teased.

Jack’s grin was wide as he turned to look at her at last, “Yes please.”

“We can ask. I’ll also let her know if she wants to allow you to penetrate her, she can.”

“Thank you, Mistress.” 

“You’re very welcome, Jack. I can’t wait to hurt you. It’s going to be such a rough night for you.”

His response was a soft shudder but he did not raise a single objection. His submission had already deepened, humiliated as he was during his examination. She needed to sort out her work situation, now that there was a Jack and a possible Cristiana connection.