Petsitting Ch. 01: Wednesday

It was a quiet little street in a quiet little neighborhood. Even the crickets seemed muted as they chirped in the blanketing darkness, which was interrupted only by the faintest traces of pink in the western sky. The houses stood in a neat row, a respectable distance from each other but still neighborly. The lawns were well-manicured and the trees were primly trimmed.

It was onto this street the SUV turned, bright headlights cutting a swath through the dusk. The man driving it counted the house numbers and finally found a cream brick house near the end of the street - number 405. He nodded and carefully backed into a spot on the driveway.

His movements were deliberate and unhurried as he killed the engine, unbuckled his seatbelt, and exited the car. He walked to the back and opened the hatch, where a dog kennel rested, covered by a blanket and prevented from sliding by a two orange straps running from the side over the top to the other side of trunk. He unbuckled the straps and carefully rolled and stored them. He folded the blanket and set it aside.

The kennel was heavy, but he wrestled it gamely from the trunk and carried it to the front stoop of the house. The porch light glowed warmly and the doorbell sounded a cheery little chime when he pressed it.

The storm door behind the glass outer door opened a moment later, revealing a man with brown hair cut short in back and little longer in front. He was fit but not built, and had a slight shadow on his jaw. He smiled in greeting at his guest.

"Thanks for taking her on such short notice, James," the driver said. "I thought we had her cycle pretty well tracked but it showed up a day early."

"Not to worry. It was a pretty boring Wednesday but this makes it more interesting," James said as he opened the glass door to allow his guest entry. "Come on in, Holt."

Holt hoisted the kennel again and walked inside. The entryway and adjoining living room were covered in a beautiful dark hardwood floor that extended into the kitchen. Holt made his way past it to the den, where thick, brown carpet softened his steps. There was a fire already licking the grate of the gas fireplace across the room and the chocolate brown suede couch curved around the walls invitingly.

He set the kennel on the floor and knelt to unlock and open the door.

"Beer, Holt?" James called from the kitchen.

"No, but thank you. I can't stay too long," Holt replied as he rose from the floor and sank onto the couch. He clicked his tongue and patted his leg.

The girl inside the kennel responded to his summons, carefully extricating herself from her confines. She padded over to him on her hands and knees, stretching each limb as she went to ease the cramped muscles.

"Good girl," Holt murmured as she sat at his feet.

She was on the petite side. Her small breasts could barely fill his hands when he cupped them, and her hands and feet were delicate and finely boned. Her nose tilted up just slightly at its end. She had creamy skin that marked easily and her strawberry blonde hair was gathered in pigtails high on either side of her head.

Holt thought she was absolutely beautiful and James had to agree as he joined them in the den.

"She's eaten already tonight, so don't worry about that," Holt said as he gently pet her head. "She had cramps a little while ago but I gave her some Ibuprofen and she should be fine. If she needs more, there's a bottle of Midol in her kennel. I put some toys for her in there too. I took her collar off so you can use your own, if you'd like."

"Is she wearing her menstrual cup?"

Holt nodded. "That should be taken out, emptied, and cleaned every twelve hours or so. She can do that herself, but you're welcome to do it for her if you prefer."

The girl blushed crimson in front of him but said nothing. Holt noticed anyway and traced a gentle finger down her face.

"Is her safe word the same as last time?"

"Yes - Bethesda. Her hometown. I know I gave it to you last time, but just in case, I wrote down a list of her allergies and her hard limits," Holt said, and he took a folded piece of paper from his wallet and handed it to James.

James looked it over with pursed lips and noted with satisfaction that all of his plans for the week were doable under the limits she had set. "How much anal training have you done with her?"

The girl stiffened under Holt's hands but he continued stroking her just the same. "Sounds like you've got a fun week planned," he joked. "I really haven't done anything with her ass. Anal never did anything for me so I haven't bothered."

"When was her last bowel movement?"

The girl turned an even brighter shade of red, but this time Holt took no notice. "She had one this morning, but none since."

"Anything else I should know?"

Holt shook his head. "That's all I can think of. You can call me if you need it. And you," he added, turning his attention to the girl at his feet, "be good for James. If I hear you've misbehaved, I'll punish you on top of whatever he does."

The girl gave a little yip in acknowledgement and Holt's stern expression melted into a smile. "Good girl," he murmured. "Have fun. I love you." He bent and pressed a kiss to her lips that she returned happily.

James walked him to the front door as the girl padded behind them on hands and knees. "I'll call the minute her period's done," he promised Holt.

"Thanks again, man," Holt said as he got into his car. "See you in about five days, pup."

The girl watched as he drove away, and then looked up at James with just a bit of apprehension.

"You're okay," he assured. He crouched beside the girl and offered her a hand to sniff. She nosed against his fingers gently, and then relaxed as he moved to stroke her cheek and down her neck. He chuckled at her blissful expression as he pet her. "You're not so hard," he teased. "Go get reacquainted with the house, puppy. I'll call when I need you."

Pup watched as he jogged up the stairs to the second story, then turned to take in the house. She had been here last month and the month before that, and still she'd never seen it on two feet. The thought crossed her mind but the next step, standing up, never occurred to her. She crawled carefully over the wood floors, stopping to admire the plush furniture and décor of the living room before making her way back to the kitchen. Here there was an empty food dish sitting next to a full water bowl. She took a quick drink, mindful of her pigtails that swung like dog ears around her face.

There was a comfortable dog bed in the den, close to the fireplace, and there was already a blanket folded inside of it for her comfort. She looked at both approvingly.

She perked up a little as James' footsteps sounded on the stairs. He found her waiting at the bottom, looking up at him with bright eyes. He smiled at her and stepped around to the hallway to spread out the runner rug he'd retrieved from the upstairs hall.

Pup nosed at it as he smoothed it into place. "That'll be easier on your knees, puppy," he said. "Holt doesn't like when I send you back to him with any bruises you didn't earn."

She gave a little bark in amusement.

James smiled back at her and started toward the stairs again. "Heel," he directed.

She clambered up the steps behind him, obediently following him down the hallway, through his bedroom, and into the master bath. It was a beautiful room with burnished metalwork, a freckled stone sink, a standing shower and a large tub. She startled for a moment as he gently lifted her in his arms and placed her in the tub so she was kneeling on all fours.

"Well, little pup, it's just you and me for the next few days," he said, running his hands over her skin. She shivered as his touch raised goosebumps when he went from her back to the sides of her breasts to her hips. "And you seem to be down one hole for me to use. But we know what to do about that, don't we?"

Pup heard trouble in his words and raised her head sharply to find his eyes.

"Stay," he commanded softly. She watched as he went to the bathroom sink and rummaged in the cabinet below it. He came back up with a bag and some tubing, and something that looked suspiciously like a nozzle. She whimpered and he turned and caught her gaze at the sound. He must have seen something on her face, because he dropped the materials and strode out of the room.

He came back a moment later, a thick leather collar in hand, and sat himself down on the edge of the tub.

"Have you ever had an enema, puppy?" he asked softly as he placed the collar around her neck and did up the buckle with deft, gentle fingers.

Pup shook her head and leaned into his hand when he lifted a palm to her cheek.

"I'm going to give you one tonight. A couple, actually." He smoothed his thumb over her skin when she looked up in alarm. "It's okay, puppy. I know you can do this for me. It's going to be a little uncomfortable, but we need to clean you out. I'm going to train up your ass this week."

She must have looked uneasy at the prospect because he sighed and framed her face with both hands, so he could direct her to meet his gaze.

"Tell me your safe word, Hannah."

The use of her name meant she was to answer verbally, as a human.

"Bethesda, sir."

"Are you afraid, Hannah?"

She wanted to duck her head in embarrassment, but his grip on her head, gentle but firm, prevented it. "Yes, sir," she whispered. "But excited, too."

He smiled at that. "Do you trust that I'll keep you safe, and not harm you, Hannah? And that I can make you feel good?"

It was her turn to smile. In the end, he made her feel amazing, every time. It was just that, often, the journey to that incredible end was laced with pain. "I do trust you, sir," she answered.

"And can I trust that you'll use your safe word if you need it, Hannah?"

"Yes, sir." She hoped she wouldn't need it. She didn't think she would. James was frighteningly skilled at skirting and nudging at the very limits of what she could tolerate without ever quite pushing her over.

He rewarded her answer with a smile and kiss on her forehead. "You are such a good puppy," he whispered.

And just like that, Hannah was Pup again. She relished being Pup. It was simpler and less stressful than being Hannah. Pup did not have deadlines to meet or bills to worry about. All she had to do was obey orders and make her masters happy, which they returned ten-fold. She never felt as cherished and protected and cared for as she did when she was Pup.

Except now she was feeling nervous as James returned to the sink and began to fiddle with the tubes and bag again. She watched as he filled the bag and tested the temperature of the water, then brought the whole apparatus over to the tub. He placed it on the tub floor between her lower legs, then returned to the cabinet briefly to snag a bottle of lubricant.

James settled himself on the side of the bathtub and thumbed open the top of the bottle. Pup glanced over her shoulder in time to see him squeeze a generous amount onto his forefinger. He casually reached an arm around her middle to pull her a little closer to his side.

"Relax for me, pup," he directed.

She tried, but jerked forward when she felt the cold, wet touch of lube on her asshole. He merely tightened his grip around her hips to hold her in place.

"Easy, puppy," he murmured, soothing. "This is going to go in, so you may as well relax to make it hurt less. I don't want you in pain. Yet."

Pup felt a little thrill of excitement race through her at the words, and in that moment James took advantage and pressed all the way in in one smooth motion. She gasped and stiffened, but it was far too late.

"There we go. That's it," he praised. "Just get used to it, pretty pup." He gently began to move his finger around, slowly pressing and retreating. His other hand, down beneath her from where he'd wound his arm around her middle, found her shaved pussy and began to gather the dew that had been collecting there ever since she'd been put in her crate at Holt's house.

His finger felt strange inside of her. It wasn't painful, exactly, though certainly not comfortable. Just, strange, Pup decided. It felt stranger when he pulled it out almost entirely and then thrust back in. There was pain then, a burning from the friction of his skin against her sphincter, despite the lube.

"Relax," he reminded her in a seductive whisper, and this time when he pulled out and thrust in again, it didn't hurt quite as much.

And that was the lesson, she realized. Stay relaxed, stay loose and unclenched, and there would not be pain.

James finger-fucked her ass a few more times before he was certain the point had hit home with her. She wasn't exactly moaning in pleasure, but neither was she fighting it when he thrust inside of her. At the end of her time with him, he thought with a smile, she would remember back to this night when a single finger inside of her ass was a trial, and laugh.

He pulled out completely, satisfied that he had worked enough lube inside of her. She looked over her shoulder curiously when she felt him pull away.

"Time for your enema, puppy," he said softly. "It's going to be uncomfortable, but I know you can be a good girl for me and take it. Just relax for me, little girl, just stay loose and -"

She gasped and arched under his hands as he slid the nozzle inside of her without warning. It was only partially inside by the time she clenched in surprise, so he held the nozzle and tube steady, talking to her to soothe her and coax her into easing her muscles. The moment she did, he slid it home so she wouldn't have time to be anxious about it.

"This is a smaller enema, pup, but it's mixed with soap that's going to cause a little cramping," he said, stroking one hand over her ass and down her thigh. "I'm going to have you hold it for about fifteen minutes to make sure it works through you."

It would feel like a lifetime for her, he thought as he opened the valve on the bag. He held it just above her cute little butt to let gravity do some of the work. The water was lukewarm, just about her body temperature. It was the time and the soap that would get her. He knew he was a sadistic bastard even as he thought it, but a part of him was looking forward to seeing her writhe, to watch her face as she weathered the pain of the cramps that would wrack her little body. There was something so fucking hot about watching her bear the pain, just for him.

He kept up a steady stream of compliments and soothing nonsense as the water flowed. Pup whined occasionally, but she would always quiet down when he rubbed a gentle hand down her back or over her belly. This enema was too small to do it, but the next enema he planned for her would distend her belly, draw it taut and round. James was already hard, but just the thought of her stomach swollen and aching made his cock stiffen to the point where he had to adjust the front of his jeans.

Pup was whining in earnest by the time the bag was empty. She shivered in place as she crouched above the tub floor, bending every now and again to try and shift the water within her to a more comfortable position.

"Easy girl," James murmured, petting her back. "I'm going to pull the tube out very slowly. I want you to clench your little asshole so you don't lose any of the water, understand?

She yipped an affirmative and he slowly began to draw the nozzle from her bottom, stopping every few centimeters so she had time to acclimate to the feeling and to get ready for its exit. When he finally pulled it out, she clenched every muscle.

"Good girl," he praised. "I'm very proud of you for that, pup. Just fifteen minutes and then I'll let you release it all."

Pup shivered again, leaning into his side so she could press her body against his. James would never be as versed as Holt in the subtleties of her body language - Holt could carry on entire conversations with her based on the tilt of her eyebrow or the twitch of her lip - but he knew his little puppy well enough to know when she needed a soft touch, a kind word, or a sharp slap to her bottom. Right now, with her hip pressed to his legs like she was trying to fuse to his body, she needed every possible piece of encouragement he could give her.

He reached down and began to massage her stomach, pressing here and there with warm, steady hands to ease the pressure that was cramping her gut. Pup leaned into his touch, turning slightly to nuzzle against his knee to show her gratitude.

He had to laugh when her eyes flashed at the sight of his cock tenting the front of his pants.

"See something you want?" he teased.

She gave him a shy little yip and licked her lips, which was an invitation if he ever saw one.

"All right, pretty pup. Far be it for me to deny you a treat." James rose and moved to the end of the tub in front of her face, and obligingly pulled out his cock. It grew even harder when he saw her give a happy little shiver and press her legs together.

"Let's see what you remember from last time, puppy," he said. "Go ahead."

She looked like she wanted to pounce, but she held herself together and began to lap at his cock, her soft, warm tongue brushing his skin like a butterfly's wings. He groaned and ran a hand over her cheek to cup her jaw.

"Keep going," he directed when she looked up questioningly. "You're doing well, pup."

They'd worked extensively on oral training the last time she had stayed with him. Holt never did do well with the sight of blood, and had once passed out when his mother had cut her hand chopping vegetables. Just knowing his pet was on her period, even if he never saw the blood, was enough to make him uneasy. Three months ago, James volunteered to take puppy for the week, and both Holt and his pet were intrigued by the idea.

The first month had been a bit of a trial period, just to see how things would go. Last month was dedicated to curing Pup of her gag reflex and developing the skills of her lips and tongue.

She remembered well, James thought, and she'd been practicing. She ran the flat of her tongue up the underside of his shaft and then wrapped her lips around his head, sucking with a strong pull that made him buck his hips so he could thrust further into her mouth. The moan she emitted when he did was one of the hottest sounds he'd ever heard.

Pup bathed his cock with her mouth, massaging its length with her lips and glancing up now and again to make sure she was bringing him pleasure. She was tight and hot around his length, especially when he thrust in further and hit the back of her throat. The feeling was exquisite, and when James closed his eyes he swore he could see the sun. She didn't just blow him - she worshipped him with her mouth and it was one of the hottest fucking things he'd had the privilege to watch or feel.

Occasionally, though, her rhythm would falter and a look of pain would cross her face as her stomach cramped. James would stroke her face and murmur kindly to her to help her weather it, and once, when she took too long to resume her licking, he had to tap her nose to redirect her focus.

"Just a couple more minutes, puppy," he told her when one cramp hit her particularly hard. "Make me cum and I'll let you release it."

She wanted to bob her head up and down, to use her tongue and lips to tease, but James wanted that throat. He wrapped her pigtails in each hand and gently, but firmly, began drawing her head slowly down his shaft.

"Relax," he instructed. "You remember how to do this. You can do, it pretty pup. Relax and swallow - oh, good girl!"

He felt his cock slide home into her throat and looked down into her watering eyes, just above where her nose was pressed into his pubic bone. She swallowed convulsively and her muscles bunched and shifted and squeezed his cock like the tightest fist. He threw his head back and exhaled in a relieved rush, moaning when she moved her tongue against the underside of his dick. James began thrusting, short little bursts at first so as not to overwhelm her, and then longer and harder, pushing into her mouth and over that silken tongue that felt so damn good.