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Introduction:

Callie returns to her new master's home to begin her anal training.

Callie had been instructed by Master Travis to return the following Saturday at the same time for her next round of training. “Don’t forget, you must fast for at least twelve hours beforehand. And I want that little asshole shaved clean,” he had told her last weekend before sending her on a walk of shame back to her apartment.

Of course Callie complied; in a way she had no idea what to expect, so she didn’t want anything going wrong due to her not following the rules. It was Saturday evening, and she had only drank tea and water since the afternoon before. She showered and carefully shaved around her virgin asshole, as well as her pussy lips in order to give an overall groomed appearance. Travis had told her that her clothing wasn’t important, so she wore a soft pair of cotton shorts and a tank top. She arrived at his door promptly at 6:00pm, and he ushered her inside and to the couch.

“Well I’m sure you’re anxious about what to expect tonight,” he said with a mischievous grin that made Callie giggle nervously. “Don’t worry, I’m going to take exceptionally good care of that tight little ass of yours…I’ll be gentle at first, but a bit of pain is to be expected your first time, just like with your first cunt.” Master Travis’s cock was quickly turning rock hard just from explaining what he was about to do to her. “Naturally, I’ll get first privileges on your asshole. But Master Wilson is on his way to help me train you as well.” He watched Callie’s eyes widen as she heard this unexpected information. Wilson had assisted Travis in training well over twenty assholes over the years…it had become something of a tradition at this point. Plus, Travis liked that Wilson was methodical and had a somewhat clinical process of preparing a virgin asshole to become a slutty second cunt. “But before he gets here, I want you to suck my cock to get me nice and hard for that tight ass.”

“Yes, Master.” Callie immediately complied and briefly stood to remove her clothing. Travis had taught her that all acts of service were to be performed completely naked. After shedding her shirt and shorts, she got on her knees and knelt in between his legs. She briefly rubbed her hand on his bulge over his pants before slipping her hand inside and grabbing his semi-hard cock out. Callie went to work sucking and licking on his tip; she hadn’t yet gotten to his shaft when there was a knock at the door.

“Be a good girl and go open the door,” Travis commanded.

Callie nervously obeyed, standing and walking to the door, still stark naked. She turned the lock and opened the front door which led out to the shared hallway, where any neighbors were subject to walk by and see her. There stood Wilson, dressed in practically the same clothes she had seen him in last weekend and carrying a backpack. His eyes turned to saucers the second he saw Callie standing there, her chubby naked body on fully display. She let out a meek “hello sir.” He came inside and immediately began groping her exposed tits and ass.

“Goddamn,” Wilson said while playfully bouncing her tits in his hands, then he wrapped his arms around her waist, sliding his hands down to her ass. “Oh we’re going to have fun with this one,” he said as he suddenly grabbed both her ass cheeks hard and spread them apart, exposing her asshole to Travis who was watching and stroking his cock on the couch. Callie gasped as she felt the air hit her freshly shaved hole.

“I was just having her start on my cock,” Travis said to Wilson. “She’s ready for training…she’s been fasted.”

“Excellent,” Wilson said as he led Callie back over to the couch. “Keep servicing your Master’s cock while I get a good look at this little shithole…” He guided her to get on all fours with her face in Travis’s crotch and her ass up in the air. Travis fed her his cock while Wilson knelt behind her and spread her ass cheeks once more. He put his nose in close and smelled her scent before taking his tongue in circles around her tight, wrinkled hole. Callie moaned with Travis’s now fully hard cock shoved deep down her throat.

After he had sufficiently tasted her, Wilson opened the backpack that he had brought with him. He took out a large bottle of lube, a slender glass dildo, a bulbous metal buttplug, an enema kit, and a towel. He opened the towel and placed it underneath Callie, slipping it under her knees. He then grabbed the lube and pumped out a generous amount onto her puckered little asshole, letting it drip down between her pussy lips. Callie continued throating her Master’s cock as Wilson then plunged his middle finger inside the lubed up hole that would soon become her second cunt. The sensation was mostly pleasurable as it didn’t stretch her too much. As she felt his finger slide deep inside her, Callie let out a loud moan which subsequently caused her to choke and gag on Travis’s cock.

“Mmmm, good girl,” Wilson purred as he twisted his finger around inside her warm, tight hole. “She has a very soft little shithole,” he said to Travis. “I think it should stretch nicely.” He slowly retracted his finger, which was knuckle deep, and began to prepare the enema kit. He took the bag, hose, and nozzle out of his backpack, along with a bottle filled with his own homemade enema solution. “I can tell that you’ve prepared your ass as instructed like a good little whore,” he said to Callie. “But we’re going to make sure that your little fuckhole is nice and cleaned out.”

Travis, who had been holding Callie’s head in both his hands as he fucked her throat, slid his head off his cock momentarily so that she could squeak out a “Yes, sir,” to Wilson.

Still kneeling behind her, Wilson filled the enema bag with his bottle of special solution. He then lubed up the nozzle and slowly pushed it inside Callie’s hungry butthole, watching it swallow the inch-long tip and then tighten back up around the hose. “Very good,” Wilson said as he raised the bag above his head and started to gently squeeze the fluid down into the hose. Callie began to whimper as she felt the nozzle prod inside of her tight asshole; it wasn’t as thick as Wilson’s finger but it was hard and inflexible. As soon as the tapered plastic tip went far enough inside of her, it hooked to the inside of her rectum. The foreign object felt uncomfortable and made her squirm. Then, the solution trickled down the hose and inside her ass which was another very odd sensation.

“Very good,” Wilson said again. “Keep very still now.” Callie did her best to control her wriggling as Wilson pumped the enema solution through the hose and continued to fill her entire ass and colon. She felt like she would explode at any time, but the nozzle kept her plugged. “Perfect, that’s all of it,” Wilson said as he squeezed the last drops of the solution into Callie’s bulging rosebud. “Okay if I take her to the tub?” he asked Travis, who nodded.

While holding the hose that was still hanging out of her ass, Wilson helped Callie to her feet and walked her down the hallway and into the bathroom. Callie could feel the liquid sloshing around inside of her intestines, and the way she had to waddle down the hallway made her feel quite embarrassed. When they entered the bathroom, Wilson pointed to the tub. “Get in. Squat down as much as you can and I’ll take it out.”

“Yes, sir,” Callie said as she carefully climbed into the bathtub, standing with her face to the wall and squatting down as much as her belly would allow.

“You’ll need to push as I pull it,” Wilson instructed her. “Then, I want you to push everything out until you’re totally empty, every last drop.”

“Yes, sir,” Callie chirped, beginning to feel nervous. The bathroom was cold and her nipples were pointed rock hard. She had never felt more vulnerable than in this moment.

“Such a good little fuckwhore,” Wilson cooed as he swiftly tugged on the enema hose while Callie pushed and dilated her opening. The nozzle tip slid out with not much resistance; Callie kept bearing down and the liquid went shooting out of her asshole and into the tub. “Yes, keep going,” Wilson coached her. At one point she had to stop and her hole closed back up, so when she pushed again a loud fart noise accompanied the solution pouring out of her ass. Callie was surprised at how much it was.

Travis, who had been setting up the air mattress in the living room for their next training phase, entered the bathroom and chuckled at the site of his girl being cleaned out for use like a propter fucktoy. “You pissing out your ass, baby?” He taunted her with a grin, standing in the doorframe.

Callie had her back to him so his voice slightly startled her, causing her hole to clench up again. “Yes, Master,” she said before pushing a final time to get out the last of the solution.

“She prepared herself well, it’s all coming out clear,” Wilson observed as the last of the liquid snaked down the tub drain. He helped Callie out of the tub and toweled down her inner thighs which were wet with the enema solution. He also had her bend over at the waist so he could dry her asshole.

They walked back into the living room and Wilson instructed her to get on all fours on the air mattress. While she complied, he retrieved a zip tie from his backpack. “Let’s tie this bitch up, she’ll need to be restrained while we open this ass up,” he said as he fastened the ties around Callie’s wrists. “Just makes it so much easier to get a nice stretch without you trying to push me off.” He fastened them as tight as they could go without cutting off her blood flow.

Once she was in position, Wilson retrieved the lube and the glass dildo from his training supplies. It was about eight inches long and ribbed along the shaft. Once again he knelt behind Callie and her exposed fuckholes, ready to initiate the next phase of her anal whore training.

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