Over the course of the next week, Travis had Callie over to his place every night to continue training her asshole. He’d start out by fucking her with a dildo, the size of which increased each day, and then at the end of the night he’d fuck her with his cock, finish in her ass, and send her back home with a sore, dripping hole. By the end of the week the soreness began to subside and Callie started to very much enjoy the feeling of her ass being used and filled up. Travis was ecstatic with her progress and how quickly she’d assimilated into being such a good whore.
The next big event in her training was a bachelor party for Ryan’s brother; he had booked Callie as well as another of Travis’s slaves named Gia for a few hours of debauchery. The attendees were of course Ryan and his brother, as well as another one of their married friends. “My bro will only fuck his wife’s pussy,” Ryan had texted to Travis as they were setting up the evening. “So we want to pound a lot of ass.”
Travis had the two girls over to his apartment before the men arrived to prep them. Callie knew that she would be performing service with another woman, but when she got there she was surprised to see that Gia was someone who also lived in their apartment complex; she remembered seeing her a couple of times at the mailboxes. Gia was around the same age as Callie, and she was also thick with large, pendulous breasts. She was Italian and had warm olive skin and long black hair. It made Callie wonder how many other girls living in their complex were a part of this harem that Travis was running.
Gia was very warm and friendly and appeared very comfortable. The two girls chatted while doing their makeup and Callie learned that Gia had been a slave for about two years now. Callie had never had any kind of sexual experience with a woman, but she immediately felt extremely comfortable and safe with Gia. They changed out of their lounge wear and into their lingerie in the living room with Travis watching while he rolled a joint. Ryan had requested they wear neon colored fishnet stockings and matching thongs with no tops.
“You girls look amazing,” he complimented his two scantily clad, curvy sluts. “The guests will be here any moment. Go ahead and assume your positions.”
Gia and Callie both got on all fours on the couch, sticking out their asses so that their holes were almost visible under their skimpy thongs. Just a moment later, Travis was opening the door for his guests. The three men started jeering as soon as they set their sights on the two plump asses that were just waiting to serve them. There was Ryan, his brother, Brad, and one of Brad’s groomsmen named Scott. All three were similar in stature; average height, decently good-looking white dudes whose biggest kink was stepping out on their wives to perform kinky sex acts on the neighborhood whores. All of them went over to the couch and immediately started to spank and jiggle the girls’ asscheeks. Not surprisingly, Ryan was the most aggressive and acted as the ringleader of the group. One at a time he yanked down each girl’s thong and roughly spread their cheeks open to expose their service holes to the other men.
“Fuck yes,” Ryan growled before biting on Gia’s left cheek and then firmly slapping Callie’s. “You fuckpigs are going to give my little bro the bachelor party he deserves, aren’t you?”
“Yes, sir!” Callie and Gia said in unison.
“That’s right…all three of us are going to pound your fat fucking shitholes, but Brad goes first as the guest of honor.” Ryan took a step back and began to pull his cock out like the other two men had already done. “Go on bro, which slut’s pighole do you want first?”
Hard cock in hand, Brad walked up behind Gia and began sliding his meaty cock between her asscheeks. Having been a fuckslave for as long as she had, her ass was now well trained and almost immediately began to gape even before Brad’s dick came anywhere near it. He circled the tip of his cock around her widening hole while simultaneously spitting onto it, watching his saliva slide down inside her well-stretched rectum.
At the same time, Ryan kept Callie bent over and began to finger her asshole with his thick middle finger, sliding it all the way to his knuckle. Brad had finally popped his meaty cock head inside of Gia’s asshole and was gently stroking it in and out. Scott had come around to Gia’s mouth and was shoving the length of his shaft down her throat.
Callie’s pussy started dripping as she watched her counterpart get her holes stuffed. Before long, Brad was stroking his full length in and out of Gia’s ass; her eyes began to roll back into her head as she moaned with Scott’s thick cock in her mouth.
Then Ryan took his finger out of Callie’s ass and told her, “On your knees, bitch. And face Master Brad.” To which she immediately complied, turning around and kneeling right next to Gia’s round ass. Ryan stood up behind Callie and reached down to place two fingers from each hand into her mouth, grabbing the insides of her cheeks and spreading wide. “Stick that tongue out like a good little slutpig,” he commanded her.
Callie was beginning to feel especially degraded, which was also turning her on immensely. She stuck her tongue out as far as she could with Ryan’s fingers still roughly keeping her lips open. Then, Brad pulled his cock out of Gia’s asshole, turned to Callie and slid his cock onto her wet tongue and down her open throat.
“That’s right, clean that cock with your hungry pighole,” Ryan continued to hold Callie’s lips open as his brother began to fuck her mouth. Before he felt like he was going to cum, Brad pulled his throbbing cock out of her throat and plunged it back into Gia’s waiting asshole.
The three men proceeded to take turns fucking Gia’s ass and then Callie’s mouth, back and forth. They took their time filling her asshole with their thick cocks, pumping their length in and out, and then making sure that Callie licked them clean each time it was her turn for service. She knelt with her hands behind her back while the men degraded her mouth over and over; tasting Gia’s asshole off of each men’s cock made her pussy incredibly wet. Once Callie’s makeup was completely smeared all over her face and she was nearly out of breath from all of the cock being roughly shoved down her throat, Ryan decided it was time for her and Gia to switch places.
Instead of being on all fours though, Callie was guided to lay down on her back with her legs pulled back as far as they could go so that her tight, puckered little asshole was perfectly exposed below her puffy pussy lips. Meanwhile Gina took her position on her knees, mouth already open and waiting to accept a cock.
As the guest of honor, Brad got first turn on Callie’s ass as well. He went to her and bent his knees until his cock head was perfectly aligned with her shithole. He looked down and spit a huge gob onto his shaft before firmly prodding his tip inside of her rectum. As turned on as she was, Callie found herself suddenly nervous to be offering up her asshole to these three men. She had performed an enema on herself before she came to the party, but she was still a bit nervous about what else could happen after the three bachelors tore into her ass. Nonetheless, she did her best to relax her muscles as much as possible as she had been trained.
“Fuck, this one’s tight…,” Brad grunted as he continued to push his entire head inside of Callie’s ass.
“She needs breaking in, brother – don’t go easy on her now!” Ryan roared with laughter as Gia throated and gagged on his throbbing cock.
With that, Brad began pounding away at Callie’s asshole, slamming his thick cock in and out. It was slightly painful how quickly he was stretching her rectum; as much as she tried to relax, Callie could feel her sphincter contracting around his cock. She let out a sharp gasp followed by light panting as Brad roughly fucked her hole. Finally, he pulled out of Callie and ordered her to gape as wide as she could. All three men angled themselves to observe her opened butthole.
Without wasting any time, Brad moved over to Gia and fed his cock into her open mouth. Ryan, who could wait no longer, eagerly moved into his brother’s place between Callie’s wide open legs. He slapped her pussy a few times with his mushroom head before sliding it down between her lips, over her first hole and down to the second, where he swiftly plugged his cock into her still slightly gaped ass. Callie let out a shriek; her asshole was sore from the pounding she had just received from servicing Brad. Her scream only turned on Ryan even more, and he sunk his cock as deep in her ass as he could.
“Shut the fuck up and take it like a good pig,” he growled as he began forcefully pumping his thick cock in and out of her shithole. “That’s some good fuckhole right there, nice and wet just like a second pussy!” He and the other men roared with laughter while Callie bit her lip and tried to keep in her sobs and moans. She now understood what her Master Travis meant when he spoke about training her asshole to become her second cunt. At this point Callie’s ass had been used by multiple cocks, all in just one short week. After today her ass would be blown out and ready for use just like her primed little pussy.
Ryan took his time fucking Callie’s fat little ass before releasing his nut deep inside her rectum. At the same time, Brad was cuming in Gia’s slutty mouth. Then for the final round, Scott got sloppy seconds on Callie’s shithole while Gia sucked Ryan’s cock clean. Scott’s cock wasn’t as thick as Ryan’s so Callie felt a bit more pleasure as she serviced him with her ass, but he was just as merciless on her as the two men before him. He thrust his hard cock balls-deep inside of her until he also came with his dick buried in her rectum. Callie’s stretched and used hole gaped wide after Scott pulled out his milked cock.
“Look at this shit!” Ryan grunted as he went over to Callie and spread her cheeks with both hands, putting her blown out shithole on display. “Push that cum out of that wrecked little fuckhole,” he ordered Callie, who instantly complied by bearing down and flexing her sphincter muscle; she could feel the hot, wet jizz push up and out of her asshole, trickling down between her cheeks and onto the floor. On the second push, some air accompanied the last of the cum that was in Callie’s rectum, causing her to let out a squelching fart that made the men roar with laughter. It was the final humiliating cherry on top of the cake that had been her first anal gangbang.