Wilson squirted a generous amount of lube onto her asshole before beginning to rim her with the tip of the dildo. The cold sensation made her tense up slightly. “Relax your muscles,” he advised her as he began to push the tip slowly inside her tight entrance. “And push out that little shithole, it will make it go in easier.” Callie did as she was told, and as she pushed out she felt the hard glass sink deeper into her butthole, whimpering as it passed the point where a finger would have stopped. Inch by inch, Wilson fed the ribbed glass into her hole that was opening just enough to accept the foreign object. Any time he stopped, her little rosebud puckered up around the shaft of the dildo. “Very, very good…,” Wilson said under his breath as the length of the toy was halfway buried inside her tight ass. Callie would describe the sensation as strangely pleasurable; it felt much different than being fucked in her pussy. Once the dildo hit the halfway point, the depth in her rectum caused full body shivers, which she had never quite experienced before.
Master Travis came around to Callie’s other end and had her suck him off again while Wilson spent some time steadily fucking her asshole with the glass shaft. He took a good ten minutes to slowly stretch her to the point where her ass could swallow the entire length of the dildo. With Travis’s cock balls deep inside her throat, Wilson shoved the toy’s whole length inside of her, and then pulled it all the way back out in one swift motion. He repeated this technique a few times, until her little hole gaped slightly when the tip of the dildo popped out of her. It wasn’t a huge gape, maybe just a half-inch in diameter, but it was all that Wilson needed in order to move on to the next phase of her training.
“She’s ready,” he nodded to Travis, who removed his shaft from Callie’s slobbering mouth and stood up to walk behind her. Wilson took a seat on the couch and took out his phone to begin recording. They always commemorated the first moments of a girl getting her anal cherry torn out. Then, they would send the footage to the other men who took part in her slut training, who would then share it with whoever they pleased to get the word out about the newest neighborhood fuckslut.
Master Travis stood behind Callie and mounted her, then spit onto her asshole for lube before rubbing his big cock head against her slightly dilated asshole. “Are you ready for me to take your asshole as your second cunt, whore?” He asked Callie in a deep growl.
Callie did her best to fully relax her muscles instead of tense them up, which was difficult to do considering how nervous she was. She was ready, but she was anxiously anticipating the pain that would come along with this necessary task. “Yes, Master,” she finally said after mustering up the courage. With that, Travis carefully massaged his cock head inside her tight little butthole; he instantly groaned and grabbed both her cheeks as her warm hole pulsated around his tip. Callie gasped, feeling her rectum stretch when he popped his head inside of her.
“That’s it…good girl,” Travis said as he pushed his cock deeper inside her, filling up her little asshole and stretching her walls. He had to use his hand to guide his hard cock into her ass because it was so tight, but once his head popped in he was able to sink his shaft pretty easily; he was rather impressed at how well she was taking it. Callie was moaning loudly and whimpering, but she hadn’t screamed yet which he was proud of. He went balls deep inside her virgin asshole and held it there at the hilt for a moment, letting her feel his full girth stretching her anus. At that moment Callie felt a burst of sharp pain which caused her to yelp and tears began to roll out of her eyes, but Travis held her down and kept his cock steady inside of her. “Don’t you push me out,” he warned her, to which she immediately relaxed her muscles again as best she could.
He pumped his cock into her ass for a good five minutes straight, stroking it just like he would a pussy. But oh, was it fucking tight…Travis had to focus hard in order to keep from busting too soon; it was important that he give her shithole a proper first fucking. He had to make sure that she really was capable of having her ass treated like a second cunt, so he needed to test her. The pop of pain she had experienced moments earlier was what Travis considered the official popping of her anal cherry; it was almost like her rectum muscle snapped like a rubber band, which was normal for first time taking the full length of a cock. It also typically came with a trickle of blood from a small tear in the skin, which was another marker of deflowering. Sure enough, Travis’s cock was tinted red when he finally pulled his shaft out of her tight little shithole, but not before filling it up with his thick cum which immediately began to leak down between her pussy lips.
Wilson, still recording, zoomed in on the cum shot before ending the video and promptly sending it to Jay, Ryan, and about six other men in their circle (and of course to Travis so that he could receive the replies) with the caption: “Fresh meat: new hole for rent!”
Travis went to the bathroom to grab a damp towel, with which he wiped Callie’s blood off his member. “Only for your first time will I clean my own cock,” he informed her as he finished up. “Now that you’ve been stretched, the worst of the bleeding is over. From here on out you’ll clean every cock that fucks your first or second cunt with your mouth, understand?”
“Yes, Master…,” Callie rasped out, her face still pressed against the mattress as her stretched asshole remained spread open and leaking his spunk.
“Now, push the rest of it out so that Wilson can finish with you,” Travis commanded.
Callie flexed her muscles to push out all the cum from the depths of her bowels, and in doing so she let out a loud squelching fart that made both the men chuckle in unison.
“That’s how you know that ass has been good and stretched; plenty of air in there!” Wilson bellowed as he stroked his fat cock and approached Callie. “Keep pushing that hole open,” he instructed her as he took his free hand and scooped out the rest of Travis’s cum from her asshole with his thick finger. He then shoved the finger into Callie’s mouth, forcing her to clean off and swallow the sperm that had been inside her asshole. “Like that, you dirty little bitch?”
He then spread her cheeks forcefully with both his hands, helping her to stretch her shithole as far as it could go. “Keep it open just like that, perfect…” Wilson sunk his throbbing cock head inside of Callie’s gaping, raw hole.
She immediately started to squirm; his cock was so much wider and thicker than Travis’s, and it stretched her asshole even farther than she thought possible. Callie began to whimper in pain louder and louder as Wilson shoved his fat cock deeper and deeper inside of her, stretching her insides so far that she felt like she could explode. Now she knew what he meant about needing to restrain her with the handcuffs; otherwise she definitely would have tried to push him off by now. Wilson was now full on rabbit-humping her ass, pumping his fat six inches in and out of her as fast as he could. At this point Callie was crying and drooling all over the mattress. She couldn’t even believe he was able to fit his cock inside her asshole, the discomfort was so sharp. But all she could do was lie there and shriek in pain while he had his way.
“Keep taking it baby,” Travis coached her as he sat on the couch with his post-nut joint. He could tell that she was really in pain from her gasps and moans; her face was also beet-red and covered with snot and tears. Her cuffed hands were balled together in tight fists. It was somewhat hard for him to witness, but he also took solace in knowing that just like with her first cunt, she would no doubt come to enjoy and even crave having her second cunt used with enough practice.
Just a few moments later, Wilson finished inside her ass with a roaring groan. “Fucking amazing,” he remarked as he pulled his cock out of her gaped, raw hole. “Nicest asshole I’ve had in quite awhile. The guys will love it.” He moved around to Callie’s face and had her clean his softening cock, which was covered in a film of blood and semen. His hot cum leaked out of her stretched hole as she meticulously licked and cleaned every inch of Wilson’s nasty cock, just like her Master had taught her to do. It was her slut holes that made the cock so filthy, so it was her responsibility to clean up her mess.
“Yeah man, you know I’m already getting blown up from the video,” Travis smirked as he scrolled through the texts on his phone. Wilson put his clothes back on and packed his training kit, and then fist bumped Travis before he departed. Another successful ass training on the books. After Wilson left, Travis helped Callie to shower and gently douche out her asshole until she was squeaky clean. She was exhausted and passed out in his bed immediately after the warm shower. While she slept, Travis replied to his texts and made plans for her next slutty venture.