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MILITARY SCHOOL TRAINING & MANAGEMENT, Chapter 19
Guided by the sheriff's strong, thick arms and hands, the "colonel" bobbed up and down on the erection. Before long, he tasted the Man's slick, salty precum and slid his hand along the hard shaft, as the sheriff chuckled.
"That's right, Chucky boy, give it a good tight suck," the sheriff commanded. "Y'all know how to do that real good."
Once again, he felt the rush of conflicting emotions, hating what he was doing and the denial of normal sex, while being attracted to the sheriff's authority to the point of being addicted to the shaft he despised, and especially to the years of humiliation that had turned him into a groveling, housebroken servant.
Now the sheriff was panting hard. His dick swelled and ejaculated, shooting waves of Man milk into his throat.
"That's a boy," the sheriff said, as he withdrew his tool and sent the last couple of squirts onto the top of the Trainee's head. He added some saliva, and rubbed the mixture into the Trainee's scalp, topping it off by spitting directly into his upturned mouth. "Chuck here knows how to treat a Man, doesn't he?"
"Yes sir," the docile "colonel" replied, meekly. "Thank you, sir."
"Okay, fellas, time to acquaint Caleb Jr. with the fine points of squirting off the Trainees," the sheriff said, smiling as he stood and pulled up his uniform pants. "Let's take Chucky and Clifton to the bedroom, and show Caleb how it's done."
They walked into the larger of the cabin's two sleeping rooms, and the sheriff ordered Chuck to strip and lie on one of the beds there.
"You have to clear out the Trainee's pipes every so often," he said. "It should be done at least every six months, but they can be drained more often."
Because a Trainee is strictly forbidden from stimulating his own dick or having it jacked off, the sheriff explained, the "drainings" were achieved through the anus, by way of prostate stimulation. It could be done by screwing, either with the Top's dick or a dildo or buttplug, or with fingers and a vibrator.
"It's often better to start with your fingers," he said, pulling a rubber glove onto his hand, lubricating two digits and slowly working them into Chuck's rectum. "It'll take longer for him to cum, but he'll get there."
After about 10 minutes, the "colonel" was moaning and panting, and finally he dribbled onto his stomach. The sheriff scooped up the slime and rubbed it over Chuck's hair and face, followed by a "thank you, sir."
"The best part is that the Trainee can be fucked over and over," the sheriff said, with a chuckle. "He'll keep getting those buttgasms. They'll be dry squirts, but them's the breaks. Want to jam the old boy, Caleb?"
"You bet, sheriff!" the young Captain replied to his father, flashing a malevolent grin. He stood up, showing a thick bulge in his tight uniform, and unzipped his pants. He hauled out a thick erection, spread lubricant on it, and moved into position. He slowly entered the Trainee's rectum, and soon built a steady rhythm.
"I always knew you liked dick," Caleb said to the Trainee who had once called himself his father. The young Man's voice was hard as nails as he relentlessly pushed in and out, now pumping past the second ring that gripped tight. "Oh yeah, squeeze down on it, queer old man."
The "colonel" bucked and moaned again, tightening further on the rail he was riding while the sheriff's son shot deep inside.
In the meantime, Zeke secured the younger trainee in a reclining chair that backed up to a wall. He worked for a few minutes, using a series of leather straps to render Clifton immobile, his arms and hands bound in back of his head, his midsection held tight against the reclined chairback, and his legs spread wide to expose his rectum.
After Caleb was finished with the "colonel" and had received the appropriate thanks, meek and dutiful, Zeke smiled from across the room as Captain Harlan stepped up to continue the assault on the "colonel."
The sheriff watched as his son pulled on a glove, lubricated it, smiled widely, and began to massage Clifton's prostate. The prone Trainee's involuntary movements eventually caused the leather restraints to creak softly as he struggled.
"It's a good way to start things out, junior," the sheriff said. "Sometimes I like to squirt off Chuck with my fingers, then fuck him. If Zeke's around, maybe he'll fuck him too, and there are times when the other deputies will be there."
"Yeah, I heard all about it," Caleb replied, watching Clifton's cum dribble out from the end of his dick, which had been freed from the cage to show that it had been reduced in length to 2-1/2 inches hard. He dipped his fingers into the small pool of liquid on the Trainee's stomach and fed it to him.
"Thank you, sir," Clifton said, looking into his half-brother's eyes as he prepared to follow up. Soon, Caleb was pumping his hardness deep inside, and the Trainee moaned and bucked and squeezed again. He had just fucked both of them, and when he was finished he sat back in another chair and smiled widely.
A week later, the Commandant and the Tops gathered again.
"I've been giving the following talk for almost 30 years, and the Captains who hear it for the first time are often surprised to hear me speak on the theme of compassion as it applies to Trainees," he began.
A long time back, a recently-graduated Top had called him, worried and in need of advice, the Commandant said. He had felt sorry for his Trainee, and had removed his cage and was going to set him up with prostitutes. After the rigors of the Trainee program, the Top thought it was the compassionate thing to do.
"He came to his senses and pulled back at the last minute, but when he told me about it I decided that future Tops needed to fully understand what 'compassion' means," he said.
"Keep in mind that Trainee status is never imposed, but is always voluntary," the Commandant said. "A cadet is offered a choice between staying as a Trainee and leaving with no prejudice. The program is outlined, and they choose. Trainees are a breed of their own, but they are never forced into it."
It is commendable for a Top to feel some sympathy for his Trainee, he said.
"These poor fellas will never have normal sex, and a Top can't help but recoil at the idea," he continued. "Tops and Trainees have male bodies and Tops will often feel a kinship that makes them want to relax."
But they're wrong about that, the Commandant said. Any similarities begin and end with the same body structure.
"Trainees are distinguished by their disordered character," he said. "They were raised wrong and they know it, and their need for structure and submission to authority overrides their fear of the rigor of the training program. To put them through it and then remove the most important tools of their discipline is not compassion."
At that point, the sheriff spoke up.
"I am the Top that the Commandant was talking about," he told the group. "I was ready to give my Trainee what I thought was a break, but before it was too late I realized that I was doing the wrong thing, and have realized it ever since. You really can't let up. Trainees will always be liars and cheaters underneath. Training shows them their place and puts them in it, but it's up to us to keep them there."
"I would point out that even the body similarity isn't quite there either," the Commandant added, noting that the cages reduce a Trainee's dick size, and that all body hair is removed as well.
"I had thought that maybe my Trainee wasn't a queer and should be able to roll with a female every now and then," the sheriff said. "But after talking with the Commandant, I realized that it doesn't matter."
"He's absolutely correct about that," the Commandant said. "Apart from the need for periodic draining, the sexual component of training exists because it has been a central element of conquest and subjugation forever. It benefits the Trainee by ordering his life, and it benefits the Tops by educating them in the means of conquest and management of the conquered."
"Most of the Trainees are queers," one of the Tops said. "Sometimes I wonder who's really getting conquered when I fuck one deep."
"The Trainee must know his place and stay there, but there's nothing wrong if he finds it satisfying," the Commandant said. "Look, if it was just a matter of them being queer, they could keep their head down here, or leave if they are unmasked. What's satisfying to them is submission to authority. The means of submission are secondary."
"I still think that my Trainee isn't queer down deep, at least not totally," the sheriff said. "But I honestly don't care. It's not some sort of romance. It's about who's boss, and I very strongly believe that Chuck Yarrow needs one. His son Clifton is definitely a queer, but that doesn't matter either. He needs a boss."