Prison School Ch. 13

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Jesse is training his replacement, This week's new recruits.
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Part 14 of the 31 part series

Updated 06/08/2023
Created 07/08/2016
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o2byoung
o2byoung
135 Followers

Monday morning 4:30 AM already. James has waken Vern, who in turn is waking Mike. Mike and Vern are dressed and are heading to the cafeteria to start another long day.

"I'm glad you and I and Luke had that chat last night," Mike said. "I have felt that there was a barrier between us, that made it a little awkward to work together. I sure hope we get that help we are needing so bad."

"I'm still looking for love," Vern replied. "Maybe Mr. Styles will send us somebody that would like to fuck around with me." Grins. "At least I hope we get some help." Then, "I realize, Mike, you and Luke have something special going on. I've seen it in both yours and Luke's eyes, ever since we first worked together, every time Luke came through the line. I knew that it was a lot more powerful than what we had."

Getting to the cafeteria, Vern, Mike and James all enjoyed a cup of coffee together then started the morning ritual of prepping everything to have breakfast ready by 6:00 AM.

* * * * * * * *

About 6:00 AM the usual mass confusion was taking place in Dorm 1, everyone trying to get dressed to start another day. The security officer walked in and announced he was looking for Sean.

Sean stood up, not knowing why he was wanted, and stated "I am Sean, what's up?"

"Mr. Styles wants to see you in the main office at 7:30." The officer stated, then left.

Sean walked over to Eric. "Eric, Styles wants to see me at 7:30, do you know why?"

"As a matter of fact, I do." Eric answered, smiling. "He wants to interview you for a position. Don't worry, you're not in trouble, and it's nothing bad. I doubt though, that you will be training with us today. By the way, do you know you are scheduled to take your license test Thursday?"

"No, I didn't," Sean answered. "Do you think I can pass it?"

"I think so, dude, I have confidence in you." Then, grinning, "You've had plenty of experience putting the right pipe into the right hole!" Eric laughed, giving Sean's slight bulge a little squeeze.

Adam slipped over to Eric, asking, "Eric, would it be OK if Nate eats with our group this morning?"

"Sure Adam, our table seats six, and likely Nate will be part of our PG in a day or two anyway!"

About 5 minutes later, the PG, along with Nate, headed to the cafeteria for breakfast. They filled their plates and all sat at the same table. Nate and Adam were the slow eaters, as they spent more time smiling at each other and holding hands than eating. About 7:00 all the crew except Sean and Nate, turned in their dirty dishes and left to catch the bus. Nate and Sean got a 2nd cup of coffee and chatted for a while.

About 7:20 Sean left Nate sitting there alone, as he had that 7:30 meeting with Ruben so Nate went over and sat with the other GM guys.

* * * * * * * *

Ruben came out of his office, spotted Sean, and walked over to him, extending his hand. "Come on into my office." Ruben said. Sean followed Ruben into the inner office and Ruben closed the door. Then, sitting down behind his big desk, indicated for Sean to sit in the chair in front of the desk.

"Sean, there are a number of things happening here that we need to discuss, and then you will need to make a decision. My understanding is that you have nearly completed your plumbing training, and are ready for your licensing test, am I correct?" Sean nodded, and Styles continued. "Even though your training is complete, you still have four months time to spend before your release into society."

"Are you aware, Sean, that my sidekick, Jesse, has nearly completed his time, and will be leaving us after next week?

"I didn't know that, sir."

"So here is the situation." Styles continued. "Most of the students that have finished their training, and still have time left to serve, are usually placed in Grounds & Maintenance. Sometimes, like right now, we have an opening for a desirable man, to act as a liaison, or go-between, to work with the students, especially the new arrivals. Jesse has been filling this spot for the last 3 months, and, since he is leaving, I need a replacement. Are you be interested?"

"It sounds interesting." Sean replied. "If I accept the offer, exactly what are my responsibilities? And what are the pro's and con's?

"It's actually a rather easy job. You will help the new recruits fill out their paperwork, take their measurements for, and issue their clothing, You will help them understand how the system works here, and get acclimated. Help them become comfortable and, hopefully, feel at home here. You are responsible to help them select their beds and record where they sleep, so if we need to locate them, they can be found. You will also issue their bedding and towels."

"Follow me, Sean. I want to show you another enmity of this position." Ruben opened the door to another room. "This is the master bedroom, with an attached bathroom, complete with a queen sized bed! When I am here, which is most nights, you get to share this beautiful room and bed with me!"

Sean, backing out of the doorway, "So that's the catch? I would have to sleep with you?"

"I've done some investigating about you. I know you have sucked quite a few guys off, so I would have to assume that you are gay. Styles continued, "Am I correct?"

"To be honest, I've never considered myself to be gay, but I do like to suck dicks. " Sean continued, "I've only been fucked a couple times. What do you like, as for sex?"

"Actually, I'm pretty versatile. I love blowjobs, both ways, I love to cuddle, touch, kiss, and, sometimes I like to fuck. Jesse really liked my cock up his ass, and I'm going to miss that bottom of his! If you accept the offer, I would treat you very tenderly. I wouldn't want to hurt you."

"So, if I agree, when would I start?"

"I could have Jesse start showing you the ropes today. We have several new recruits that will probably arrive around 10:00 or 10:30. You can shadow Jesse today, and next Monday, as the newbys always come in on Mondays. Two weeks from today you will be on your own."

Styles went on, "You still have a little plumbing training to do, but should finish up tomorrow and Wednesday, then, assuming you pass your test Thursday, you'll just be working here until your time is done. What do you say, Sean? Are you in?"

Sean, rubbing his chin in thought. "Mr. Styles, I accept!"

"Good boy!" Styles, smiling, put his arms around Sean, hugging him. "You'll be fine, Sean, and you can call me Ruben."

Ruben and Sean walked out of Ruben's private office into the main office. Jesse was sitting at the desk, looking at some papers.

"Ruben, you've got six recruits coming in today?" questioned Jesse.

"Yes. Culinary Arts really needs at least two or even three trainees. I pushed the warden to really try to get me some CA trainees. Jesse, do you know Sean?"

"Yeah, we're only a couple beds apart in Dorm 1."

"Sean is going to be your successor. Today Sean is going to shadow you, so do the best you can to show him what he needs to know. OK?"

"Sure Ruben," Jesse smiled and gave Sean a welcoming handshake. "Mondays are the most interesting and fun day of the week, Sean. We usually have about four new recruits every week, but today we have six coming in, probably at about 10:00 or a little after."

Sean, thinking back a couple years, "Let me guess, these guys are fresh from the pen, wearing those orange coveralls, and we get to strip them naked! And they get all red faced like they've never seen a naked guy, or been naked before in front of anybody!"

Jesse is starting to giggle hysterically, "You just took half my fun away, like you know the game already!" Grins, "I can tell we are going to have a good time today! Let's go outside and watch for the van."

Ruben came back out of his office, holding a sheet of paper. "Hold on, Jesse!" Ruben exclaimed. Do you know Nathan?"

"I don't really know him, but I know who he is." Jesse answered. "He is in the GM group."

"Give him this paper, please. It is his acceptance into the Plumbing Group, effective tomorrow." Ruben said. "In reality, Nathan is replacing Sean, after Sean passes his plumbing test Thursday."

* * * * * * * *

The van is on its way to the prison school. It left the penitentiary about 7:00 AM that morning loaded with six men today. Two or three of the guys are urgently in need of a rest room. They asked John, the driver, to please stop somewhere so they could pee, and he said he wasn't permitted to stop anywhere until he reached the school property.

Bryan was holding himself, and every time the van hit a bump he lost a squirt into his orange coveralls, which now had a noticeably darker orange crotch.

"How much longer?" Bryan cried. "I'm leaking!"

John answered, "Try to hold on for just about 4, maybe 5 minutes, and we'll be on school property."

Once John pulled onto the gravel road heading into the school, he stopped the van.

"Pee stop, make it quick." John hollered.

Four guys quickly exited the van, preparing to relieve themselves. They were, of course, all wearing those orange prison coveralls, with one zipper that could unzip from either the top or bottom.

"The fuckin' zippers stuck," Bryan cried, "And I can't hold it!"

Cory said, "Open it from the top!"

Bryan reached up to his neck, unzipped his coveralls and popped the already dribbling penis out of his coveralls, finally getting relief.

Stephen puts a hand on Bryan's shoulder, "Sorry man, sometimes shit just happens."

"It's just embarrassing," Bryan uttered, "21 and peeing in my pants!"

John pulled the van up to the main building, and told the passengers to just follow him into the main office.

"Hey Ruben," John hollered, "I got you a big load today!"

Ruben came out from his inner office. "Thanks John," he replied, as he eyed the newcomers. "I'm Mr. Styles, and also the head cheese around here. You guys will not normally have to deal with me, unless you get yourself in some kind of trouble. I will be assisting you with orientation in the cafeteria after lunch."

"This is Jesse, and Sean," Ruben continued, "They will help you guys get your clothing straight and I'll see you after lunch."

"Now, first things first," Jesse stated. "This is a training school, not a prison, so we've got to get you guys out of those ugly orange prison uniforms and into something more comfortable. Now if you dudes will just follow us we'll see what we can find!"

Sean, noticing that Bryan's coveralls looked wet in the crotch area, reached in and felt his coveralls, confirming that Bryan likely had peed in them.

Sean, loud enough for all to hear, "Dude, you're supposed to pee outside your pants, not inside." Bryan's face immediately turned red.

Bryan replied, "The ride was too long, and I just couldn't hold it!"

Jesse and Sean led them to a room marked "Clothing Issue" and the guys all followed them in. Jesse pointed to a large box and told the newcomers to strip and drop the prison coveralls into the box.

Usually there are one or two in each group of newbys that have a problem with being naked, but for some reason, all six of these guys just went with the flow.

Jesse and Sean are trying to make a mental note of what these guys look like. Jeremy, on the end is 23 and looks 16. He is about 5'4, and quite skinny with curly red hair, and the red hair extends to his armpits, a light dusting of red hair on his chest, and a red trail running down to his red pubes. He is sporting about a 4" cut cock, and with his freckles he is rather cute.

Cory is 24, 5'10, Black with captivating green eyes, a lean, muscular build, and has about a 7" cut cock.

David is 26, 5'9, lean, with brown hair and eyes, lots of body hair and a 6" uncut cock.

Bryan is 21, 5'10, with blonde hair, blue eyes, solidly built, with a very attractive 6' cut cock resting in a nest of blonde pubes.

Stephen is 20, 5'9, with shoulder length, light brown hair, hazel eyes, slender and sporting about an 8" soft, cut cock.

Troy is 24, about 6' tall, light skinned black with almost yellow hair, soft brown eyes, medium build and a 5½ " cut cock.

For some unexplained reason, some young men, when naked around other naked men seem to grow boners, for no reason what so ever. Three or four of these guys are no exception, although they maybe are not completely erect, they are more than flaccid.

Jesse spoke, "Guys, we need to get your measurements, waist and inseam, to make sure we give you jeans that will fit properly. Belts are not permitted, so waist size is important, as we don't want your pants to sag either."

"Sean, here, is training to take my place, as I am finished after 2 more weeks, and I'll be a free girl!" Grins, not afraid to indicate his sexuality. "This is Sean's first time, taking measurements, so I may have to help him out a little. I'll write them down."

"What is your name?" Sean asked the first man, who was standing there with a small, but very stiff erection that was jutting almost straight out from his red pubes.

"Jeremy."

Sean, while putting the tape around Jeremy's waist. "Waist, 22." Sean couldn't resist pushing the head of Jeremy's very stiff cock all the way to one side, then let his fingers slide over the head, releasing it, and it sprang back to the straight out position. He looked up to see Jeremy's face, which was almost as red as his hair, but he was also grinning from ear to ear.

Jeremy spoke, smiling, "I might not be very big, but I can get very hard!"

"So I see!" Sean replied, smiling. "Almost like steel!" Then Sean took the tape and measured Jeremy's inseam. "Inseam, 25." Then, wrapped his hand around Jeremy's stiff, giving it an affectionate squeeze, looking up at his face, and winked, causing Jeremy to smile.

Sean had to adjust himself, hardly believing that a guy with such a small dick could arouse him this much. He had never sucked a dick as small as Jeremy's, and yet he wanted it. And he also noticed that Jeremy seemed to enjoy the touching that Sean had done on his cock. Is Jeremy gay? Don't know, but most likely he can be had. Sean is hoping that Jeremy ends up in the same dorm.

Sean then measured Cory's waist, then dropped down on one knee to measure his inseam, accidentally on purpose sliding the back of his hand along Cory's substantial length, making it jerk just a little. He looked up into those captivating green eyes and had an urge to want to kiss Cory's lips. He did notice a little smirk on Cory's face, indicating that the touch did not irritate him.

He then moved on to David, measuring the waist then the inseam, again, accidentally touching David's six inch, thick, uncut, but flaccid penis. Sean noticed the difference, just in that instant of feeling the foreskin, and seemed reluctant to pull his hand away, liking the smoothness of that velvety foreskin, while looking up into David's face and eyes.

David, grinning and speaking just above a whisper, "You want it, don't you!"

Sean tried to just ignore the comment, stood up and gave the numbers to Jesse and moved on to Bryan. While measuring Bryan, Sean couldn't keep his eyes away from David's now erect cock, the head of which had poked through the end of the foreskin, the entire cock now close to 8" long and hard, and a couple drops of pre had formed on the tip. David's eyes never left Sean's face, and Sean finally smiled and winked at David. Sean's own cock was begging for release from the confines of his jeans, and had leaked a noticeable dark spot on his jeans.

Now finished with Bryan's measurements, Sean moved on to Stephen. Stephen's waist was 32", and so was his inseam. Sean wanted to, but was almost afraid to touch Stephen's huge manhood. It was easily 8" long and more than 1½" thick, in its soft state. Sean couldn't help but wonder how big it might be when hard.

Sean obviously acknowledged Stephen's huge manhood, as he looked first at the monster cock then up at Stephen's face, smiled and nodded his head in approval. Stephen then grabbed Sean's hand, drawing it toward his crotch and placing it on that huge dick.

Stephen spoke very softly, "It loves to be fondled!" and smiled.

Sean, grinning, "Is that an invitation?" Stephen nodded. "Another time and place, maybe." Sean answered.

Finally, Sean was down to measuring Troy. Sean noticed that, not only was Troy's skin light, his hair was golden and kinky, he also had a smaller dick than most black guys. His chest was smooth, with no hair, but he had the typical wider nose and thicker lips of most black dudes. Sean took his measurements, and accidentally wiped the back of his hand along the length of Troy's nearly erect cock, causing troy to grin, knowingly.

Now that all of the measurements were recorded, Jesse showed Sean how the clothing was handed out to the new students. Three pairs of jeans, a 6-pack of socks, and 2 3-packs each of white boxers and tee shirts. It's been realized that 3 each of boxers and tees are not enough, so it has been doubled.

"OK Guys," Jesse said, "go ahead and get dressed, and we can go down to the cafeteria and have some lunch. There are," pointing, "some plastic bags you can use to hold your extra clothing, until we assign you beds and lockers, after orientation."

Jesse and Sean led the new guys to the cafeteria. On the way, they passed by the restroom. Sean pointed it out to, in particular, Bryan, just in case, causing the poor boy to blush again. A couple of the other guys took advantage of the facility.

"I would suggest," Jesse stated, "That you men all sit at that table down there at the end, then, after lunch, you'll be there for orientation. Sean and I will sit elsewhere, as we have some things to discuss."

* * * * * * * *

"Well Sean, " Jesse asked, "Do you think you're going to like this job?"

"I think so," Sean replied. "I can see where Mondays can be a lot of fun. It seemed to me that none of these guys minded me touching them, down there, and some seemed to actually enjoy it. Two of the dudes actually tried to come on to me!"

"This group is a little different than most." Jesse stated. "There are nearly always at least one or two guys that are very straight and homophobic, and fuss about the nudity and get really irritated when touched. My intuition is that all of these men are open to some experimentation. My Gaydar says Jeremy is 100% gay, and a couple of the others are at least Bi."

"Next time," Sean exclaimed, "I'm going to jack off before I try to take the measurements. My cock was so hard and leaking the whole time! I'm normally not turned on, seeing small dicks, but with Jeremy, I had to restrain my self from wanting to take that little pecker in my mouth. His little cock is hard as steel! And he is cute too."

"What about David?" Jesse asked. "You seemed to turn him on."

"Oh god! His foreskin is so smooth and velvety. I've never done, or even felt, an uncut dick before. I can almost imagine how good that would feel in my mouth!" and, while making an adjustment, "Shit, I'm hard again, just thinking about it!"

"See why Ruben always likes to get a gay guy to do this job?"

"But I don't think I'm really gay, I just like to suck cocks." Sean replied. "I never have had any emotional feelings towards any guys, just a desire to suck them off."

"Well," Jesse said, "If you don't give Ruben a little ass now and then, he'll replace you."

"I can't say I'm thrilled about that aspect, but, if that's what it takes." Sean replied. "This job is a lot nicer than cutting grass for the next four months!"

Jesse inquired, "Sean, did Ruben tell you he will expect you to sleep with him?"

"He said just on the nights he stays here."

"That's most nights." Jesse responded, "Haven't you noticed I spend hardly any nights in the dorm? Ruben goes home maybe a couple nights a week, usually on the weekends."

"I never see Ruben in the cafeteria in the evening. Where does he eat dinner?"

o2byoung
o2byoung
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