Petsitting Ch. 02: Thursday

"All right, Hannah," James said as he heard adjust herself, "I want you to start fucking yourself with the plug that's in your ass. Use the lube if you have to. Pull it out gently, and then press it back inside of yourself, slowly. Tell me how it feels."

Hannah bit her lip as she complied. It was one thing to have James press the plug inside of her. Doing it herself was another matter entirely. It pulled and stretched on the way out, which was something of a mystery. It was a thinner plug, she knew, just by comparison to the plug James had left for her on the bathroom sink. It burned when she tried to press it back inside. She told him so, a hint of tears in her voice.

"Slow and easy, sweet girl," James said in encouragement. "This isn't meant to hurt. Put a little bit of lube on it and try again."

That helped, and so did James' voice talking her through it. "Just relax," he coaxed. "Just relax all those muscles and feel your hole open up. It's just going to slip right in, feel it?"

"Yes, sir," she breathed. "There's a point the plug hits up inside of me and then I feel it all over my body."

"Good girl. You're being so good that I think you should get a little reward," James praised. "Gently take that clothespin off of your clit, Hannah. When you can stand it, I want you to rub your clit while you're fucking your ass with the plug."

The words sent her pussy spasming, desperate to be filled and fucked. She wanted to weep with frustration. There would be no playing with her cunt today. Even in her desperation Hannah could recognize the point of this lesson. James was conditioning her, teaching her to associate anal play with pleasure.

She hissed at the feeling of blood pumping to her clit when she released it from the clothespin. Its freedom stood in stark contrast to her throbbing nipples, still trapped, still aching, especially when she began to circle a gentle finger over that little button.

Her other hand went to the plug, tentatively pulling it to the feel the stretch as the wider phalange slipped past her ring. She couldn't stop a small moan when she pressed it back in. The burn was less this time, easier to handle. And, if she were honest, the feeling of the plug filling her up again was electric, especially as she fingered her clit.

In and out again, and again, with her fingers swirling over her center, the plug grew slippery as her pussy grew so wet that her juices began sliding down to her ass. The burn was still there, but each time she eased that invader in and out of her hole, the ache lessened and the - not quite pleasure, but something akin to it - increased. That feeling harmonized with the delightful sensations emanating from her clit, mixing until her bottom half was buzzing.

Through it all, James' voice was there, encouraging, offering praise, groaning as he imagined the sight she made on the bed. And truthfully, it was his voice, his delightfully filthy words to her as she lay on the bed, that drove her to the edge.

"Yes, sweetheart, fuck that ass for me," he ordered. "Feel that plug fill you up. Do you like that, Hannah? Do you like fucking your ass, feeling so full and stretched? How does it feel, my dirty girl, knowing that hole belongs to me?"

"Please!" she gasped. "Please, sir, I need to cum!"

"Oh, really?" James drawled. "What makes you say that?"

She whined in frustration. "My ass is so full, sir, and it feels good when I'm pushing the plug inside of me. My clit and my nipples are throbbing, please!"

"Hmm," James considered. "I would like let you cum, Hannah, I truly would, but do you remember what you said to me when you opened the nightstand drawer?"

Her heart sank. "I said, 'absolutely not,' sir," she whispered.

"There's your answer," James replied. "That's enough, Hannah. Take your hand away from your clit."

It physically hurt to obey him. She was on that thin razor's edge, where one little nudge would put her right over into a delicious orgasm - but she resisted.

"Replace your plug with the larger one," James continued. "When you're done, you can release your nipples. I'll be home at six, and I expect my puppy to be waiting."

Across town in his law office, he regretfully terminated the call. James' workplace was a converted Victorian home in the downtown, a relic of the past that had survived to match its surroundings by evolving into a place of business. There was a private accountant who rented out the upstairs and across the hall, James' partner had his own office in what used to be the sitting room.

There were advantages to working in such a space, he reflected as he stood from his desk. The biggest one at the moment was that his office had a private bathroom where he could go relieve the erection that was tenting the front of his slacks, and had been ever since he had dialed his pretty little puppy's number.

~

Pup was dancing at the front door on her hands and knees when he opened it, her grin wide and happy at seeing James walk inside with a leather briefcase in one hand and a bag of takeout in the other. He let his case fall to the floor in the foyer as he knelt to stroke his pet, running his hands over her hair and face. She leaned into his touch, eyes closed in pleasure.

"Good to see you too, puppy," he murmured, noting with approval that the base of the plug peeped from between her rounded cheeks. "Come on in the kitchen. I'm hungry."

He couldn't help a smile himself as she bounced ahead of him, wiggling her sweet little ass. It had to be sore from the fucking and wearing the plug all day, but his puppy didn't let that slow her down. She sat down expectantly beside her dish, looking up at him with a grin.

James returned it with one of his own. "Uh-uh, pup," he admonished. "Not today. Come here."

Apprehension flashed across her face, and James couldn't help but feel a little smug about that. He was careful of his subs, always, but it was nice to know he could inspire trepidation with just a glance or a few words. Pup had learned quickly that any break in their routine meant she was in for a new experience, and she could never be sure if it was going to be painful, pleasurable, or an overwhelming combination of both.

This time, James lifted her onto the countertop of the island in the center of the kitchen. She hissed as the cold granite chilled her skin, but made no other protest as he eased her onto her back. He drew her arms over her head and bent her elbows so that the counter hit right in the crook and her forearms dangled down the side. The opposite end hit the bend of her knees and left her pretty little calves and feet hanging above the floor.

"Stay," he ordered, checking once over his shoulder to make sure Pup obeyed. He never really needed to worry on that front, though, James reflected as he jogged upstairs to gather the supplies he wanted. Pup was a good pet, a perfectionist who viewed disobedience as a personal failing. It was a decent trait to a point; she had a tendency to beat herself up if she messed up, a habit James and Holt were trying to break her of. And while he appreciated her adherence to the rules, it did rather cut down his opportunities to punish her, the little killjoy.

Sure enough, Pup hadn't moved when he returned, and still hadn't twitched by the time James ascended from the basement with two twenty-pound barbells in either hand. She held still as he arranged her to his satisfaction, shivering occasionally under his touch. Desire, not cold, her eyes assured him.

"You're beautiful, my little puppy," he said when he finally stepped back.

Pup was stretched out across the island, her wrists and ankles bound to their partners with soft cotton rope. A trailing piece anchored her limbs to a barbell set on the floor at either end of the island to ensure she'd have no slack for movement. He'd dimmed the lights in the kitchen so that the three hanging bulbs above her were the brightest in the room, and the light and shadows danced over her body in the most enticing ways. Her skin was stretched tightly across her stomach and hips, creating dips and valleys that shifted teasingly with each breath she took.

And at her center, just above her butt plug, a vibrator buzzed lazily, taped to her thigh to prevent it from leaving her clit. Already his little pup's hips were subtly moving, trying to increase her contact with it for more stimulation. She'd get no relief from that quarter. James had kept the toy to the lowest setting. He wanted her in a slow simmer, rather than a fast burn.

He pressed down on her hip, a silent command to stop moving. She whined but obeyed his unspoken order, and earned a gentle stroke up her stomach in reward. James loved that - loved that he could communicate his wishes with just a glance or a touch and that she could understand them and comply. And what was hotter was that she got off on it. He'd love to reward her a little more for responding to those subtle cues, but dinner was waiting.

Pup watched as James unpacked the takeout bag, pulling out various white cartons and lining them up. Her eyes were wide and shining as he opened one after the other and began spooning the contents on to her belly.

A scoop of sticky rice just above her navel, pieces of dim sum on top of that, and a serving of stir-fried vegetables between her hip bones - Pup shivered as she realized James' intent. She was the plate, a vessel to serve him. It was the best sort of objectification.

A heated moan escaped her lips when James met her eyes. He smiled and tore open a packet of teriyaki. Pup nearly orgasmed on the spot as he dripped the sauce over her belly, across the food and down her sides. She could feel the droplets run down her skin and pool beneath her, a sensuous slide that made her shift and stretch from the curious feelings the touch evoked in her core.

The whole scenario had the potential to be degrading, but it wasn't. It couldn't be, not with James staring at her like he was, with reverence and lust in his gaze.

"You look fucking beautiful, puppy," he whispered. "You are such a good girl. Be still for me. I need to eat."

Pup yipped her compliance, and waited patiently while James retrieved a Tsingtao from the refrigerator. He pulled a bar stool up to the island, cracked apart a pair of chopsticks, unfolded his newspaper to the sports section, and began to eat.

It was quiet in the kitchen aside from the buzz of the vibrator and the rustle of the paper, but they were the hottest fucking sounds Pup had ever heard in her life. The chopsticks scraped her belly slightly as James ate, and her skin chilled a little each time he ferried a warm vegetable to his mouth. The ropes around her wrists and ankles had only the tiniest amount of give to them, which, for some reason, made her feel safe and secure - like she was wrapped up in a blanket, cared for and loved.

She closed her eyes and let herself revel in the feel of the rope on her skin, the warmth of the food on her stomach, the vibrations teasing her soaking wet pussy. Every time the chopsticks clicked or the paper rustled, she sank just a little deeper into that special space where everything got hazy around the edges, where all she had to do was let herself feel good -

And then cold shocked her nipple.

Pup yelped as her eyes flew open. James was looking down at her sternly as he held the bottom of his beer bottle to her right breast.

"Focus, puppy," he admonished softly. "I'm glad you like what we're doing, but you need to concentrate on serving me, not on your own pleasure."

She whimpered, half in shame for allowing herself to get carried away, and half in discomfort. Her nipple was hardening under the chilled glass, and there was just a hint of pain beginning to creep in the longer James held it to her skin. She wanted to writhe, to wrench herself away from it, but that would be focusing on her own desires rather than her master's.

She got an approving nod and a small smile when she fought to remain still, but James still didn't move the bottle. One hand held it steady while the other scooped another load of vegetables and rice from her belly.

It was hard - oh God it was hard, with her nipple pebbled and freezing - but Pup kept herself motionless as James ate. Cold was radiating through her areola, turning it from pink to red the longer James kept the glass in place. It didn't hurt quite as much as the clothespins. That had been more of a biting, burning pain. This was a chilling, throbbing pain, but it did center her, keep her attention on the task at hand - and kept her very still, because if she inhaled too deeply, that would push her breast harder up against the cold.

James smiled as he gazed down at his puppy. Her shoulders were tense with the effort to be motionless, her eyes wide and focused on him, probably gauging whether he'd give her relief soon. Well, she'd been good after her reminder, so he relented - and immediately brought the bottle to the other nipple. Pup whined, but made no other sound of protest.

And God, but it made him hard. The sauce dripping down her sides, the perfect sight of her nipple tight and red, the way she fought to stay still, was fucking sexy. She was his plaything, his plate, his object to shape and use as he wished. Having that sort of power was a hell of an aphrodisiac, one James promised himself he would never take for granted.

He switched the bottle from between her nipples a few more times before he finished eating the dim sum and vegetables. There was only a bit of rice left, but he'd long since soaked up all of the teriyaki sauce that had pooled on her belly. No matter.

"Nice and still, puppy," he reminded his charge. Her eyes watched him, fascinated and a little nervous as he finally put the bottle on the counter. Her nipples had to be aching with cold, and they were puckered into the tightest little buds James had ever seen.

Perfect for licking, if he was any judge.

She gasped and then moaned as he took another packet of teriyaki, poured a bit of sauce over her right nipple, and immediately bent to take it in his mouth and lick it clean. With the taste still on his tongue, James took a bite of the last of the rice. A bit more sauce on her left nipple this time, another bite of rice. Pup shivered and moaned low in her throat, the sound thick with desire.

She had never felt so deliciously used, she thought as James chased a drop of sauce sliding down her breast with his tongue. Each soft lick, each gentle suck and bite, fanned a little spark that had started deep in her core until Pup was panting and trembling with the effort not to move. His mouth was so warm after the cold of the beer bottle and she didn't know quite how to reconcile the sensations.

She didn't orgasm by the time James had finished, but it was a close thing. And the smug bastard knew it, too.

"Need something, puppy?" he teased, gently running a warm, wet rag over her belly to clean the last traces of food away. "Those hips are moving again. That vibrator's not going to do anything else for you until I allow it."

She whined, pushing her pussy toward him in a silent plea.

"Down, girl. Be still. I'll take care of you," he promised. Dear Lord, she hoped so. She could feel the wetness between her legs, knew she was soaking the countertop beneath her.

James bent and loosened the ties around her ankles until her legs were free. He gently parted them with one hand, exposing her slit and making the plug shift inside her ass.

He stepped away for a moment and came back with a toy in hand. It was a dildo, smooth and uniform down its entire length until the end where the base flared outward to stop it from sliding inside all the way. It was, in fact, a perfect object to fuck her back passage, and Pup realized the next step of her anal training.

The plug hurt just a little as James gently unseated it.

"Relax," he reminded her. His voice was gentle and soothing and she clung to that as he lubed up the dildo. Remembering her lesson from last night, Pup took a deep breath and let it out slowly as the toy slid in. James murmured reassurances the entire time, praising her for taking it so well until the thing was fully worked into her ass.

It didn't hurt, she was surprised to realize. The plugs were tapered and so forced her hole to open wider the deeper they went, but the dildo was all one width - perhaps as big around as two of James' fingers - and didn't stretch her to the point of pain. In fact, when she really let herself relax and loose the tension in her thighs, it felt ... not great, exactly, but good. It touched nerve endings inside of her that had never really been stimulated before last night, and this time the stimulation was without the pain of an enema.

"How are you doing, puppy?" James asked. His hand was warm as he stroked her stomach, hips, and thighs. At her nod, he began to work the toy, sliding it out just a little and then back in. Back and forth, back and forth, each time pulling a little farther out and pushing back just a bit harder in.

Little by little, her tension eased until she was pliant and relaxed on the counter. James cooed praises as he fucked her puckered hole, increasing the speed now that she had surrendered to the feelings the dildo teased out of her.

When she moaned low in her throat he began angling it, brushing the walls of her ass.

"Can you feel that, pup?" he demanded, watching with satisfied eyes as she panted. "Feel your ass taking it, taking everything I give you? You like it, baby. You're turning into my sweet little anal slut, aren't you? I'm so fucking proud of that ass, puppy."

The words went straight to her clit. It was such a turn on to know that James found her pleasing, and her pussy fairly wept with cream when he praised her.

And each time he thrust the toy inside of her sensation rocketed outward from her center, leaving her breathless. The vibrator helped, especially when he bumped it up to the next setting and pressed it a little more firmly against her mound.

She found herself moaning as he fucked her harder. She couldn't help her hips from moving again, and this time, James allowed it. She rose to meet the dildo each time he thrust it in with a little breathy cry.

"God yes, puppy, make that noise again," he ordered when he heard it. She couldn't stop herself from doing anything else.

James watched the dildo disappear inside his little pup's ass, and it was so fucking sexy that he couldn't help unzipping his slacks and fishing his cock out. One hand kept the toy pistoning in and out of her hole while the other fisted his dick, pumping in time with her fucking.

He could see the walls of her pussy flutter as he pushed her closer to that edge. He was hard to the point of pain. He wanted nothing more than to replace the dildo with his cock, to watch it sliding in and out of that tight ass, but she wasn't ready for it. She would be soon, though, he reminded himself, and that thought had him almost instantly ready.

Pup was writhing on the counter beneath him, begging with that little puppy whine that never failed to delight him. He could see the strain on her face as she struggled to hold everything together, to wait for permission.

Such a good girl.

"I'm going to count down, pup," he warned her. "Wait for it. Five."

He watched as her hips suddenly went into overdrive, fucking the dildo as hard as it was fucking her.

"Four."

He gripped his cock tighter, pumping it faster as he felt his balls start to tighten.

"Three."

She was begging for it now, a high-pitched whine that spoke of her overwhelming need to cum and the strain of holding it back.

"Two."

He was fairly slamming the toy inside of her. It slid in her little hole as smooth as butter, testament to how turned on she was.

"One."