Randy learned that he would spend the next hour or so training his pussy, while Craig and Calvin watched television. He wasn't exactly sure what they meant by 'training', but he soon found out. They used the suction cup at the base of the dildo to affix it to the middle of the coffee table. He was told to lube it up good with his mouth. He started by spitting on it and stroking it with his hand, but Calvin reached forward and pulled his head down to force the dildo into his mouth. He sucked and bobbed on the big dildo, barely able to fit even just the head of it in his mouth. How the fuck was he going to fit this in his ass.
With the dildo now dripping with spit, they ordered him to get up on the table. Randy did as he was told and got on his knees on the coffee table in front of the two men. He pulled the thong strap out of the way to press his hole to the head of the thick dildo. Calvin lifted his foot and ordered Randy to take off his sock with his mouth. As Randy pressed down on the dildo, he leaned forward and struggled to use his teeth to pull the sock off of Calvin's foot. He was finally successful, the sock hanging from his mouth, just as the dildo popped past his ass lips and he felt the head lodged in his pussy. It felt too large to possibly take more.
Calvin stood up and used his cock to stuff the smelly sock into Randy's mouth, as he pushed down on the top of Randy's head to sink him further down the fat dildo. His cunt felt stretched beyond his limits and he moaned into the rank sock now filling his mouth, his tongue watering from the taste of the dirty sweat soaked fabric. Craig stood up and pulled off his pants and the jockstrap he'd been wearing, draping it over Randy's face so the pouch was covering his nose.
"Okay bitch, now work your pussy on that dildo," Craig ordered, sitting back down with his hard cock jutting straight up. Randy thought that maybe Craig was as big as the dildo he was slowly impaling himself on. Calvin then turned on the television and they sat back, occasionally looking at him but mostly focusing on the show they'd put on.
The spit helped, but not nearly enough. It felt impossible, but eventually Randy felt his butt touch the coffee table and the base of the dildo pressed to his balls. He then proceeded to pull up and then sink back down on the dildo, finding it easier to take with each stroke. Apparently the pussy training was working. He rode it like that as they pretty much ignored him, except to periodically pat him on the head, slap him in the face or rub the jock strap into his nose. Craig's jockstrap was heaven, Randy could make out the ball sweat and the piss that he was now all too familiar with. And he'd grown to appreciate the taste of Calvin's sock and the foot stink that was extracted from the fabric due to his saliva.
At one point, Calvin reached forward under Randy to cup his thong covered crotch. His dick felt hard as a rock, straining against the pouch. Calvin showed Randy how wet his hand was from the precum that must be leaking out of his cock like a faucet to the point of drenching the thong. Randy wasn't surprised when Cavin smeared the precum all over his face. All while he humiliated himself in front of them by riding the dildo.
It was somehow more embarrassing to be riding the dildo while they watched, than if he was taking their cocks. At least if he was riding their actual dicks, he'd be serving a purpose by making them cum from fucking him. Instead, the pleasure they were receiving was from watching Randy degrade himself and perform like a well-trained faggot. It felt pointless to be taking a dildo in his cunt when their were two studs there with big cocks he could be riding instead.
Once their show was over, they told Randy to get off the dildo and show them how good a job it had done opening him up. Randy's legs were sore and his ass felt like it couldn't take any more abuse. At some point in the hour long training, he had drifted out of his own head and almost robotically fucked himself. But the pain was brought back to the fore front of his mind when he heard them tell him it was time to get fucked by the real thing. They sat side by side on the coach, their cocks out and hard. Before he could turn around to present his ass, Craig pulled the suction cups off his nipples.
"Fuck yeah, look at those big titties," Calvin raised up to take one of Randy's nipples in his mouth, while Craig did the same with the other. They sucked and chewed on his tits, making Randy groan until they stopped.
"That's a good start, but they need to be bigger," Craig informed Randy, squeezing and pinching his tits. Randy endured the torment and looked down to see that they were swollen to twice their size, "Chris said he wants to grow them to be like little udders on your chest. So men can clearly see you are a fag, with your nipples poking out obscenely even through your shirt."
"Here, these will help with your tit training," Calvin said, as he affixed the metal clamps to Randy's engorged nipples. Randy winced from the pain as the tiny teeth of the clamp sank into the flesh of first one and then both nipples, "Now ride us like you did that dildo."
"Come here," Craig grabbed his hips, pulled him off the dildo and spun him around. His hole gaped wide and didn't have a chance to close before Randy was positioned so that Craig's cock was pressed to the opening, "Down."
With that one simple command, Randy lowered himself effortlessly onto Craig's cock and didn't stop until he felt Craig's full bush against his ass. Craig moaned in pleasure and Randy was ashamed at how loose his hole felt wrapped around even Craig's long fat cock. But it did feel good to have a real cock in him, rather than a fake one.
"Holy fuck, that cunt feels amazing," Craig exhaled, reaching around Randy and gripping the chain to his nipple clamps to use as a handle to raise Randy up and then bring him back down repeatedly, "You got a nice big cunt from your training, you're taking my whole cock without any problems."
"My turn," Calvin announced, sounding impatient. Craig slapped Randy's ass, indicating he should go to Calvin now. He rose off Craig and shifted over to Calvin and slid onto his slightly smaller cock with even more ease, "God damn, that feels almost as loose as a real pussy. You are gonna have to train on that dildo every day from now on. We want to be able to sink into this cunt easily whenever we need to nut."
The next half hour went on like that, Randy going back and forth between their cocks, riding them. He was embarrassed at how effortlessly he sank down on them and the sloppy sounds his cunt made as he took their dicks. There was no denying the strong friendship the two men shared as they bonded over using their faggot. They spoke as if Randy wasn't there, comparing him to Matty and the times Calvin and Craig had shared Craig's bitch back home. While Calvin said he appreciated Craig letting him get his dick sucked by Matty regularly, there was no comparison to a man being able to sink his cock into faggot pussy.
The clamps jiggled on his chest from the fucking motion. They tugged on the chain to his nipple clamps, but eventually they went numb and it didn't hurt like it did at first. The pain to his ego didn't stop though. He took in deep huffs of the smell of Craig's jock, as he sucked on Calvin's sock and swallowed down the foot sweat.
Calvin was the first to blow his load. Randy had just left Craig and sank down on Calvin, starting to raise up, when Calvin grabbed his hips and slammed him back down. He roared behind Randy and bit into his shoulder, as his cock spasmed in Randy's ass and sprayed his insides with hot cum. There were probably seven or eight shots of cum pumped into his ass, before Calvin's balls were emptied into Randy. That moment of being filled with cum made Randy feel closer to the men who were depositing their semen into him.
He raised up off Calvin, trying to be careful to keep his hole clenched to not spill any of the precious seed. Randy was horrified to realize he couldn't get his hole to close and some of Calvin's spunk drained out. Craig pulled Randy over and he sank down on his big cock, emb embarrassed at the squelching sounds his cunt made as Craig drove in and forced out more of Calvin's cum.
"God damn, that pussy is a sloppy mess," Craig sighed, "I love fucking his pussy with your load lubing him up, dude."
"You're welcome, buddy, any time," Calvin stood up in front of Randy, pulling the jockstrap off his face and yanking the sock from Randy's sore mouth, "Now clean up your mess, bitch."
"Yes, Daddy," Randy responded without thinking, deep into that delirious submissive headspace that he now associated with being a faggot. He began by lapping up the cum that had soaked into Calvin's pubes, making sure to clean up the cum from his balls, before he took Calvin's cock into his mouth.
Calvin reached down and tugged on the chain to the clamps on Randy's tits. This reignited the pain in his nipples, as Craig pushed him forward. Randy pressed into Calvin, who sat on the coffee table, forcing Randy down on his still hard cock until it penetrated his throat. Craig stood up behind and began to deep dick Randy's cunt. Just as Craig slammed into Randy with a loud triumphant roar, his cock expanding and spurting, Calvin pulled down on the chain and ripped the clamps off Randy's nipples.
The heat of the cum flooding his ass was joined by the fire on his chest that were his nipples. The numbness in his tits was replaced with a sudden excruciating pain as the blood flowed back into the abused flesh. He moaned around Calvin's cock and began to choke on it, feeling tears running down his face from the pain and humiliation of the moment. In that instant, he despised the tit clamps and hoped they'd never be used again. But he knew there was no chance of that. He was purely a fuck toy for these men to use for their pleasure.
Craig continued to drive into his ass, while Calvin forced him to breathe around the cock lodged in his throat. It wasn't until Calvin reached under Randy and began to molest his already sore nipples, that he felt the orgasm quickly approach and his clit spit up in his thong pouch. He groaned and thrashed under the two men, but they held him in place. He felt his entire body orgasm even as he felt the weird sensation of cum oozing out of his cock in a slow stream, rather than spurting during a normal orgasm.
His body was still tingling from whatever he'd just experienced, as the two men withdrew their cocks from his holes. They high fived each other and talked about how great Randy's cunt had felt. They reminded Randy that he was to now train his pussy on the dildo for at least an hour every day.
As if his ordeal was never ending, Calvin then grabbed the new plug they had bought. He held it up to Randy's face to remind him the size, before he slid it into Randy's cum filled ass without any trouble. Randy was barely able to close his hole around the tube once the plug had sunk in, but he was happy once the base of the plug was resting against his hole. He willed it to stay in place. It was definitely an odd sensation to feel the metal plugging his cunt, the bulb deep in his pussy and filling him, while his opening was closed tight around the tube. He was already dreading when it came out, but wanted it out at the same time.
"Now keep that in until morning, baby," Calvin said, kissing Randy on the forehead, "You want to hold our babies inside you all night so they soak in that pussy, don't you princess?"
"Yes, Daddy," Randy looked into Calvin's handsome face, and was happy when he gave Randy a wide smile.
"What's with the daddy stuff," Craig asked, chuckling, "You really have this bitch wrapped around your finger, I'm impressed my friend."
"It was pretty easy. Just needed a little encouragement," Calvin said to his best friend, before turning his attention back to Randy, "Now since you were such a good girl, you can sleep with Daddy tonight, baby. Tell Craig good night."