Prison School Ch. 20

Story Info
School in Jeopardy, Darin - Bryan connect -last week for 2.
3.4k words
4.53
7.1k
2

Part 21 of the 31 part series

Updated 06/08/2023
Created 07/08/2016
Share this Story

Font Size

Default Font Size

Font Spacing

Default Font Spacing

Font Face

Default Font Face

Reading Theme

Default Theme (White)
You need to Log In or Sign Up to have your customization saved in your Literotica profile.
PUBLIC BETA

Note: You can change font size, font face, and turn on dark mode by clicking the "A" icon tab in the Story Info Box.

You can temporarily switch back to a Classic Literotica® experience during our ongoing public Beta testing. Please consider leaving feedback on issues you experience or suggest improvements.

Click here
o2byoung
o2byoung
135 Followers

Authors note:

The idea for this story hit me back in early July and I was up until the wee hours of the morning writing on Chapter 1. It was the second story I wanted to write and get published here. The first story, titled "Hot Cargo," is partially based on a true personal experience, and is still in draft stage.

I have had some strange experiences while writing this. I know I am rather soft hearted, and there have been a number of emotional circumstances where the characters shed some tears, and so do I! I will admit to my shortcomings as an author. I am likely better at writing romantic parts than writing steamy sexual activity.

I've also had some situations where the characters "come alive" and do things I didn't plan. An example at the end of #19 I planned on Adam and Nate just going to bed and cuddling before drifting off to sleep. I didn't know they were going to catch Jeremy masturbating, or that Kurt was going to pop in and add to the circle jerk.

It's been fun writing it, and even though it seems there are a lot of views and a reasonable number of votes, (all the chapters have at least a 4+ rating,) the lack of feedback tells me it is not liked very much. I do not intend to leave the readers I do have in the lurch. I am going to try to end this monster within the next 4 or 5 chapters.

*****

Chapter 20 - W3 Monday Morning

Preview: This is Jesse and Zach's last week of incarceration, and they will both be leaving to return to live in the free world. Ty, the Senior Trainer in Masonry, and Glen, in GM, have only two more weeks. Smitty, in CG will be taking his certification test this week, and, assuming he passes, will be joining the GM for about 6 weeks while he completes his time.

* * * * * * * * * *

It's about 7:30 AM and most of the trainee's have already left the cafeteria to go to the training sites. The four GM guys just left to face another day of mowing grass and trimming shrubs. Jesse and Sean have turned in their dirty dishes, and are sipping a last cup of coffee.

"Well Sean," Jesse said, "We should be getting some new recruits today. I'm going to let you handle everything, but I will be hanging around if you need me to help you with anything."

"I don't foresee any problems," Sean answered, "I think I can handle everything okay." Then added, grinning, "I really like Mondays."

Jesse spoke, "Since this is my last week, I'm handing the keys over to you now." Jesse handed the keys to Sean. "So if any of the guys need anything, like lube or condoms, or applications for commissary accounts, they will need to see you instead of me."

Ruben walked into the cafeteria with a sober look on his face. He walked over and got a cup of coffee, and joined Sean and Jesse at the table, sitting down.

"Bad news, Guys." Ruben said, looking very serious. "The state is claiming budget shortages, and has suspended any new transfers to the school."

"When does that happen?" Sean asked.

Ruben answered, looking down, "I just got the email this morning. It's effective today, so we have no recruits coming in!" Shakes his head.

"What happens to the men that are already here training?" Jesse asked.

"They'll continue," Ruben said, "As far as I know. Hopefully, this is only a temporary suspension."

"That sucks!" Sean stated, looking sad.

"I'm supposed to be leaving Saturday," Jesse said, "How do I get rid of this bracelet?"

"There's a corrections officer scheduled to come here Friday afternoon, that will remove and deactivate both yours and Zachs. You're not scheduled to leave until Sat, and we trust you won't try to escape before you can legally leave on Saturday. I will stay over, Friday night, and take you and Zach to the bus station on Saturday." Ruben said. "Is that cool? And I already have your bus tickets in the office, to send you both home!"

"Wow! That fabulous!" Jesse exclaimed, smiling with a couple teardrops sliding down his face. "You've always treated me well, Ruben, and I'm going to miss you, and some other friends I have made here."

"I'm going to miss both of you faggots," Ruben replied, grinning widely. "And I hope Sean doesn't mind, if I take you to bed that last night. You know Jesse, I really like that little ass of yours."

"That's cool, Ruben," Sean said, "Get it while you can, cause it ain't gonna be 'round much longer!"

"Since we have no 'cruits this week, you guys don't have a lot to do. Enjoy the free time." Ruben said, "Let me go see what I can find to busy myself in the office." Ruben left.

"Looks like we got nuthin' to do today." Jesse mentioned. "Wanna go watch a movie till lunch time?"

"Sounds like a plan." Sean answered. The two men headed to the rec room in Dorm 1, found a DVD neither had seen, and settled down to watch it.

* * * * * * * * * *

It's about 11:45 AM and the bus was coming back to the campus, bringing all the trainees in for lunch. Bryan was sitting next to the window and Darin selected the isle seat next to him. They were talking small talk, and Darin placed his hand on Bryan's thigh, rubbing it lightly, and causing Bryan to grin a little, and he was also starting to feel his dick starting to get hard.

"I don't really mind," Bryan spoke softly, as he moved Darin's hand off his thigh, "But I don't need to walk into the cafeteria with a boner!"

"Sorry," Darin replied, smiling, "Maybe we can get together later?"

"That could be," Bryan smiled, "interesting. I'm game."

As usual, the Carpentry Group ate together, Bryan made a point to not sit next to Darin. When they got back to the job site, the memory of Darin's hand on his leg kept popping into Bryan's mind, and every time, caused him to feel an arousal in his genitals. Bryan can hardly wait for this training day to be done.

The bus pulled in front of the main building at just about 5:00 PM, and unloaded it's cargo of about 18 or 20 men. Some headed to Dorm 1 and some, including Bryan and Darin headed to Dorm 2. Several of the men quickly stripped and headed to the shower.

Darin sat on his bed for a couple minutes, and Bryan went to his bed, he looked down and saw Darin sitting on his bed, just 4 beds down from him. Bryan walked down to Darin.

"May I?" Bryan said, indicating he wanted to sit down, next to Darin on his bed. Darin motioned him to take a seat.

"Darin," Bryan nervously spoke, "I might be, well, can I ask you a question?"

"Sure Bryan, just ask it."

"I'm not sure how to, well, are you, in some weird way, I don't know, attracted to me?"

Darin smiling, "I'm not certain why, or how, but yes, I am attracted to you. I think we should get our showers and grab some chow. I think most of the guys that want to shower have, or are maybe just getting out."

Both men stripped, got their towels and soap, and headed to the shower. Luke was the only one still in the shower, and Luke and Bryan felt comfortable around each other naked. Both Darin and Bryan kind of eyed each others cocks, likely realizing they were very close in size, neither one very thick and both about 5½" long in the flaccid state and both cut. They finished quickly, dried themselves and headed back to get dressed for dinner.

When they got their trays filled, then went to the table where the rest of the CG were seated. Luke had just sat down there a couple or three minutes ahead of Darin and Bryan. The other three were already done eating, excused themselves and left.

Bryan spoke, "Darin, this is only my second week here, and I would like to get to know you a little better. Would you like to take a walk with me around the campus after dinner?"

"I'd like that Bryan." They all finished eating, and turned in their trays and dirty dishes. Luke hung around to wait for Mike. Bryan and Darin headed outside, and toward the woods. As they were walking slowly, Bryan started a conversation.

"Darin, remember what you did to me earlier? Before lunch?"

Darin, grinning, "You mean when I touched your leg? I was just playing with you, to see how easily I could make you hard. And I found out it doesn't take much to get you hard."

"I thought about what you did, all afternoon." Bryan said. "Every time I thought about it, I got a tingling sensation, an arousal, in my crotch. Can I see if I can make you hard?"

Darin, laughing, "Go for it, Bryan! Hey, there is a bench over there, let's sit down." They walked over to the bench and sat down.

Bryan placed his hands on both sides of Darin's head, then pressed his lips onto Darin's lips.

"Whoa, Dude!" Darin exclaimed, loudly, pulling back and almost tipping the bench backwards.

"You've never kissed?" asked Bryan.

"I've never kissed another man!"

"That's my favorite way to make a guy hard!"

"OKAY! You can try, but I hardly think a guy kissing me is gonna make me hard."

Bryan pressed his lips onto Darin's lips again, softly at first, then pressed his tongue between Darin's lips, swirling it around inside Darin's mouth, and against Darin's tongue. It was only about 30 seconds, and Darin's tongue started dancing with Bryan's. About 3 minutes and both men needed to come up for air.

Bryan, feeling Darin's crotch, and laughing, "So what is this I feel?"

"Ok, so you got me hard as steel, and hotter than hell!" Exclaimed Darin. "I hope you've got a plan to take care of this!"

"Let's get naked!" Bryan said, as he started to peel off his tee shirt, jeans and boxers, releasing his erection to the air. Darin just stood there, paralyzed, looking at the beauty of Bryan's magnificent erection. Not that it was huge, but it was very pretty and inviting to a hungry mouth. Finally, Bryan took things into his own hands, and started to strip Darin, exposing Darin's substantial and erect phallus to the open air.

"Bry," Darin asked, "Have you ever sucked a cock?"

"Does a bear shit in the woods?"

"So, how many times?"

"Hey Darin, I'm only 21, probably about 6 or 7 different guys, but a couple of them I did a lot of times. I've never even dated a woman, nor have I even wanted to. What about you?"

"I guess I'm kind of a novice. I've been sucked only once, and sucked a guy just once. I would guess you are gay?"

"I am." Bryan answered, unashamedly. Aren't you gay also?"

"I honestly don't know, and I never really thought too much about it."

"How old are you, and how many women have you fucked?" Bryan asked.

"That's easy, 25 and none. I figured I was young and had plenty of time to find a woman to fuck."

"Okay, let's put this stuff all on a scale." Bryan explained. "I find you attractive, and I really want to have sex with you, but that is understandable as I am gay."

"Now you told me you are attracted to me, you're 25, never had a woman sexually, and actually did have some male sex, aka blowjobs, both ways. So how does it look to you? Likely your wrist is either sore, or very muscular!"

Darin, grinning, "Yeah, I do use my hand a lot."

Bryan closed the gap between the two men, hugged Darin, and initiated another kiss, without an objection this time. The result was the same as the first kiss, two very hard cocks touching and making two bodies tremble with anxiety and desire. Both men were leaking pre in a big way.

Bryan asked, "Darin, you want to try a sixty-nine?"

"Sure," Darin said, "Lead me and I'll follow!"

"Darin, lay down on your left side," Bryan instructed, "Then I'll lay in position to line us up properly."

Both men lay down, and their cocks were perfectly aligned with the other's mouth. Bryan extended his tongue out, and licked the pre off the head of Darin's cock. Then he reached up and lightly flicked one of Darin's nipples, making Darin whine, then took the head of Darin's cock into his mouth, twirling his tongue around it, making Darin squirm just a little.

Darin copied, step by step, also tickling Bryan's nipple, and taking about half of Bryan's shaft into his mouth, starting to slowly move his head back and forth, exciting Bryan into moaning loudly. Bryan moved his hand from Darin's nipple, sliding his hand down over Darin's stomach, abdomen, and slipping it under Darin's cock and started to massage Darin's sack and balls.

Darin, letting Bryan's cock slip out, "Do you have any fuckin' idea how fuckin' good that feels?" Then took Bryan back into his mouth, working his tongue and mouth just a little faster.

Bryan swallowed the entire length of Darin, into his mouth and throat, and with the additional hand action on Darin's balls, Darin was crying in ecstasy, but still working Bryan's shaft, trying to get Bryan to shoot. Darin knew he couldn't hold off very much longer, and really wanted to make Bryan cum at the same time.

"BRYAN! I can't hold off!" Darin hollered, letting Bryan slip out of his mouth. "Jesus fucking Christ, I'm cummmmmiiiiiiinnnnnggggggg!"

Bryan took Darin's hot load, spurt after spurt of creamy white seed, filling his mouth and throat, making Bryan gag just a little at one point.

"I'm sorry Bry!" And took Bryan's still throbbing dick back into his mouth, continuing the assault. He is wondering if he really wants Bryan to cum in his mouth? He did take Josh's load a few days ago, so what the hell.

"Hey, Darin," Bryan said, "No need to be sorry, you're doing fine! I'm not far off, when you feel my dick start to pulse, you'll know I'm starting to shoot."

Darin continued to work Bryan's cock, then slid his hand under Bryan's balls, then using his finger started to lightly rub Bryan's perineum and rosebud, making Bryan jerk, and sending chills up his spine.

"Shit! That's gonna finish me off, I'm so hot and close now! Fuck! Here I come! OOOOOOOOOOOOOHHHHHHH, Oh, Oh, Oh, Fuuuuuck!"

Darin has all he can do to swallow the several rather large wads of Bryan's ejaculation. He then used his mouth to milk the last few dribbles out of Bryan's cock. The two men sat upright, next to each other, both quite well satisfied. Darin extended his hand toward Bryan, and Bryan accepted it.

Bryan is trying to be cautious about his feelings toward Darin, as he doesn't want another experience such as the one he'd had with Zach a week ago. At the same time, he is looking for someone to chum up with, and maybe have some regular sexual activity.

"Darin, " Bryan asked, "Have you ever fucked with anybody?"

"No, why?"

"I think I would like for you to fuck me."

"I don't think I could even get it up again this soon."

"I didn't mean right now," Bryan said, smiling. "Like, maybe in a day or two. I can almost imagine what it might feel like to have you inside me. We would need to round up some lube, and maybe some condoms."

"Condoms?" Darin questioned. "I didn't think guys needed to worry about pregnancy. And we've all been tested for STD's"

"If I'm going to bottom," Bryan stated, "Especially here, I think I would prefer my top is wearing a condom."

"What's meant by top or bottom?"

"I think those are gay terms." Bryan explained. "When two guys fuck, the one receiving a dick up his ass, is often called a bottom, and the other is a top." Bryan continued, "Some guys only want to bottom, and some only want to top, and some, like me, are versatile, and can be comfortable doing either."

"So why use condoms"

"It's cleaner." Bryan replied. "When a guy has just dumped a big load into your ass, you can't usually hold it all inside. It dribbles out into your underwear, and even down your pant leg. If he is wearing a condom, it catches the load, can be slipped off afterward, and, no mess!"

"I'm learning," Darin replied, smiling, "and I think I found a good teacher! Maybe we should get dressed and head back?"

The two men pulled their clothes back on.

Darin, wrapping his arms around Bryan, "Thanks a lot, Bry, that was fun, and I hope it was good for you also. I was hoping we could both get off together, but I guess that wasn't to be."

Bryan, hugging back, "It was still good, and I think we both got some needed release." Bryan was tempted to kiss Darin, but then decided not to, as he is not quite ready to become romantically involved, after the hurt he suffered from Zach.

Bryan, as they are starting the walk back, "Darin, how much time do you have left here?"

Darin, thinking, "Almost a year total, about six months of training. What about you?"

"Well, as you know, this is only my second week, so I've got nearly 8 months of training, and 12 months to serve."

"So, it would seem we have plenty of time to have some fun." Darin said.

Bryan is contemplating in his mind. Darin is definitely not homophobic, and seems receptive to learning the art of gay sex. I wonder how he will react if I try to take his ass? At least he'll be around for a while, nearly a year. Maybe, just maybe, but I have to be on guard.

Darin, As they reach the dorm, places his arm around Bryan's shoulders, "Bryan, I really want to know you better. I like you, a lot." Then, "I think I need to see Sean, and see if I can get some condoms and lube." Grins. "I think I'm going to watch some TV for a while before bed."

Bryan just heads toward his bed, removing his clothes, and laying, naked on top of the sheet. He has some thinking to do. He really likes Darin's cock, almost a twin to his own. Thinking of Darin's sweet cock causes him to start getting an erection, and he covers his body with the top sheet.

Now, Darin is planning to get some condoms and lube from Sean, so, evidently, he must want to try something new. Is Darin really gay, and just not out yet? Maybe he is just starting to accept himself. We guess time will tell. Bryan wants to be a lot closer to Darin, and at the same time, he is trying not to set himself up for heartbreak.

Suddenly the bright lights are turned off, and seconds later, Luke and Mike appear by Luke's bed, just the 2nd bed over from Bryan. They are both stripping, preparing to sleep together, as usual.

"Bryan, I can't believe you're in bed already." Luke said.

"Yeah," Bryan responded, "I'm just trying to think some things through and clear my mind."

Luke said, "I've noticed you seem to be getting a little close to Darin. He seems like a decent dude. Anything happening there?"

"I don't know yet," Bryan said, "We're just getting to know each other a little. We did take a walk in the woods tonight."

Mike, grinning, "Around here, a walk in the woods usually means some kind of sex!"

"No comment!" Bryan answered, thankful the lights were dimmed, so the redness of his face couldn't be seen.

"4:30 comes early," Mike said, "We've got to get some sleep. Goodnight Bryan." He and Luke cuddled together for the night, Luke spooning Mike.

Bryan is trying to get to sleep, but has a lot of thoughts spinning around in his mind. He was vaguely awake and aware when Zack came to bed, and shortly after, drifted off to sleep.

(to be continued)

o2byoung
o2byoung
135 Followers
Please rate this story
The author would appreciate your feedback.
  • COMMENTS
Anonymous
Our Comments Policy is available in the Lit FAQ
Post as:
Anonymous
1 Comments
AnonymousAnonymousabout 6 years ago
Great read

I've read all the chapters so far and am loving it. I always prefer to read a proper story, rather than guys just meeting and fucking. There's certainly a sense of real people meeting. Keep it up!

Share this Story

READ MORE OF THIS SERIES

Similar Stories

Sharing Five men form a loving family, and yes, sex is involved.in Gay Male
Backseat Introduction Girlfriend's dad and boyfriend share the back seat.in Gay Male
Step-Dad Screams My Name Tyler makes step-dad, Andy his bitch.in Gay Male
New World Beasts Pt. 01 Ch. 01 A werewolf creates a new son for himself.in Gay Male
Summer Sausages Ch. 01 2 horny college boys seduce the fireman next door.in Gay Male
More Stories