Young, Gay And In Prison Pt 22

As Bryan started to push the head of his cock against Darin’s hole, Darin tightened, finally relaxing, and allowing the head of Bryan’s cock to slip in, Darin let out a little yelp.

Part 21


Chapter 22 – W3 Saturday Afternoon

It’s 1:00 PM, Jesse and Zach are outside the main building, their personal clothing and any other personal items packed into a couple of plastic bags. While they wait for Ruben to come and pick them up, several of their student friends gather around to wish them a final goodbye.

Luke commented, “I somehow feel especially close to you, Zach, and I am really going to miss you. I feel like I want to kiss you goodbye, may I?”

Zach, tearing up a bit, “I’d be honored, Luke.” The two men shared a short but tender kiss and hug.

“Hey!” Mike hollered, “Don’t leave me out!” Mike stepped to Zach, and also planted a kiss on Zach’s lips, complete with a passionate hug. All three men seemed to have lost control of their tear ducts, as all had some teardrops running down their faces.

Ruben pulled up in his Honda Accord. He exited the driver’s seat, holding the bus tickets for Jesse and Zach, and two Wal-Mart $25.00 VISA gift cards, handing one to each man.

“I know neither of you have money,” Ruben stated, “At least now you will be able to buy a meal or snack on your way home.” Both men smiled at Ruben’s last minute generosity, and thanked him. They got into Ruben’s car, Jesse in front and Zach in the back. Ruben entered the driver’s side and the car took off, leaving the campus.

Suddenly Adam and Nate ran up. “Where are Zach and Jesse?” Nate asked.

“They just left, about 5 minutes ago.” Luke answered.

“Crap!” Adam responded. “We had brunch with Zach, and I thought we had time to go fuck around in the woods, and still get back in time to see them off.” Then added, “We’re going to miss Zach, he was a good friend. By the way, my parents are coming to visit next Sunday.”

“Do they know yet, about you and Nate?” questioned Mike.

“I’m going to drop it on them that day. I’m scared to death, Mike! I have no idea how they are going to react. They may disown me. At least I have love from Nathan’s family, and if my family rejects me, Nate’s family will be my only family. His parent’s are very supportive, and they can’t wait to see Nate and I as husbands.”

“And I am going to be right by his side, when he tells them!” Nate added.

“Good luck, Adam.” Mike said, “Baby, I gotta be to work at 3:00 PM, Let’s go chill till then.”

Mike and Luke headed for the Dorm, relaxed and made out on Luke’s bed until Mike had to leave.

* * * * * * * *

About 2:00 PM, Darin and Bryan were both watching TV in the Dorm 2 rec room. Darin slipped into the sleeping area and into his locker, grabbing a couple of condoms, and a tube of lube, sliding them into his pocket. He then returned to the rec room, and walked over to Bryan.

“Want to go get some fresh air?” Darin asked Bryan. Bryan, smiling, rose from his seat immediately, not needing any coaxing, or a second invitation. The two men walked out of the dorm, and Darin led the way towards the woods.

“Where are we going?” Bryan asked.

“Where we can be alone, and I can get to know you better. You do know, Bryan, that I am quite attracted to you. And I like you, a lot.” Darin continued, “What we did, a few days ago, I liked. I can’t really say that I am gay, but I am definitely not opposed to learning more, if you are willing to teach me.”

At this point they were out of sight of any humans. Darin stopped, put his hands on Bryan’s shoulders, guiding him to face him. Both men’s eyes were gazing into each other’s. Darin slowly moved his lips closer to Bryan’s, and when their lips touched, both of their mouths opened, allowing their tongues to feel around the others mouth. Both men started to feel their jeans getting tight in the crotch area.

“Is that normal?” Questioned Darin, “to kiss a guy and spring a boner?”

“I think so,” Bryan responded, grinding his own erection against Darin’s.

“The other day,” Darin stated, “You asked me to fuck you. Were you serious, and do you still want me to?”

“Absolutely! If we had condoms and lube.”

Darin, reaching into his pants pocket and pulling out something, “You mean these?”

Bryan, grinning widely, “Let’s get naked!”

Darin, cautiously, “Bryan, you’re going to have to help me here. I’ve never done this before.”

“Rape me Darin! I’ll help you!”

Both men stripped except for socks and sneakers.

“Hold on a minute,” Bryan exclaimed, “Would you consider, since I’ve done this a few times, letting me fuck you, to kind of show you how it’s done, then when you fuck me, you’ll have a better idea of how to do it?”

“I don’t know about this.” Darin said, concerned. “Does it hurt?”

“When you’re not used to it, it can hurt a little, or a lot, if you’re not prepared and opened up first. I know how to do that, and once you’re adjusted, it should start to feel really good.”

“Okay, You’re the teacher.” Darin consented. “You show me how it’s done!”

“Lay on your back.” Darin did as he was told.

“First, I’m going to put the condom on. Now, raise your legs and put them over my shoulders. Now I’m going to prepare you, I’m placing some lube into your crack, and around your orifice. This may startle you a little, I’m going to insert a finger and start to expand your hole a little.”

As Bryan started to insert a well-lubed finger, Darin resisted the strange intrusion. After a couple more try’s Bryan got his first finger in to the first knuckle.

“Relax, Darin, we’re doing fine. Now I’m going to work your hole with my finger, to get it used to the intrusion, and then I’ll use 2 fingers, then 3. That will stretch your hole a little, temporarily, and it’ll be ready for the real thing. I’m now lubing my cock, with the condom on it. It probably will hurt a little when I first push in, but I will go slow, and let you get used to it. Relax, I’m coming in.”

As Bryan started to push the head of his cock against Darin’s hole, Darin tightened, finally relaxing, and allowing the head of Bryan’s cock to slip in, Darin let out a little yelp. Bryan stopped pushing, letting Darin get used to the feel of the penetration. After a couple of minutes, he pushed in a little more, about 1″ of his shaft now inside Darin’s cavity.

He pulled back a little and shoved in again, each time pushing in a little deeper. After about 10 or 12 pushes, he was all the way in.

“I’m all the way in, how you feeling Darin?”

“I’m past the hurting now. It feels strange, but OK.”

Bryan shucked up a little, to get his cock at a better angle to start pounding on Darin’s prostate, and gradually starting to pick up speed.

“Oh shit!” Darin exclaimed, “you’re hitting a very sensitive spot. It’s really exciting! Oh, Fuck, I feel like I’m gonna cum. I am, fuck, I’m – shit, I’m cumming now, damn, stop!” Several ropes of cum shot out of Darin’s cock, splattering all over his abs, stomach and chest.

“Can you handle just a couple more minutes, Darin?” Bryan asked, “I need just a little more time to climax! I’ll try to change the angle to not pound your prostate.”

Bryan slipped down a little, still fucking Darin’s butt, but not hitting his prostate. Bryan could feel his orgasm coming on strong.

“I’m about to explode, it’s cumming now, huff, huff, I’m winded, but my balls are drained. Thanks, Darin, I needed that.”

As Bryan started to slip out of Darin’s ass, and to deflate, he pulled off the overly filled condom, throwing it into the bushes.

“What about this?” Darin asked, pointing to his stomach and chest spattered with a whole lot of cum.

“No problem!” Bryan answered, as he lowered his head and started to lick up Darin’s ejaculate. “You might still need a shower before bed though.”

“I can’t believe I came that much. That had to be the strongest orgasm I’ve ever had, and neither of us ever touched my cock. Wow!” Darin continued, in amazement, “I sure never knew a guy could cum while getting screwed. That was fuckin’ awesome!”

“OK Darin, do you think you could fuck me now?”

“You’ve got to be kidding! I’m drained! Empty. I don’t think I could even get it up right now.”

“Silly, I didn’t mean ‘right now’, I meant like maybe tomorrow. And what did you think about getting fucked for the first time?”

“Let me just say this. If I had known how good it would feel, a few years ago, this would not have been my first time. And I’m sure it won’t be the last. I liked it.” Then Darin added, “And Bryan, I like you too. I like you a whole lot.”

“I like you too, Darin, maybe a little too much. I got hurt the first week here, and I realize I need to hold on to my heart. But you owe me a good fuck now, and I’m gonna want to collect it.”

The two men finally got dressed, preparing to head back to the dorm. Once they were dressed, Darin stood directly in front of Bryan as if to block Bryan from moving. Bryan noticed a wanting look in Darin’s eyes, and was a little surprised when Darin initiated another kiss, placing his hands on the back of Bryan’s head, pulling Bryan’s lips closer to his own and both men tenderly and softly kissed.

“I think you’re beginning to like this man to man kissing.” Bryan stated, smiling.

“It was kinda weird, the first time we kissed,” Darin commented, “But now it feels so natural.” Darin’s eyes are starting to water. “Fuck natural, It feels downright awesome! I know this is gonna sound offbeat, but, do you think a man can fall in love with another man?”

“Of course!” Bryan replied. “Being gay, I couldn’t imagine falling in love with a woman. But the right man could most definitely steal my heart away.”

“I hate to say it, but I think I could fall in love with you, Bryan.”

“CAREFUL!!” Bryan exclaimed. That L word can be dangerous. You don’t even know if you’re gay! And you don’t know me well enough to know if you could love me. I think what you’re feeling is infatuation, or maybe just lust.”

“I think I am gay.” Darin stated.

“Or,” Bryan responded, “maybe you just needed some sex, and there sure are no women around here, so a guy is the next best thing. You know, Darin, there is a world of difference between sex and love. I think we all enjoy sex, and getting it off now and then. Why do you now think you are gay?”

“Just a logical deduction.” Darin answered. “When I dated women, even when making out, I didn’t have the drive to want to fuck them. Most of the time, I didn’t even get hard. But with you, just a simple two-minute kiss, and my cock is hard, throbbing, and leaking precum into my boxers and jeans. And I want to get it off!”

“And one more thing,” Darin added, “When I’m close to you, I just want to melt into you, as if to be part of you. I never felt that way toward any woman. Ever since the night we sixty-nine’d, I have thought about you, all day every day.”

“It would seem, from what you’re telling me, that you are likely gay. And I am willing to give us a chance to get to know each other.” Bryan went on, “Darin, be really careful with that L word, it can be a real heartbreaker. Tomorrow is Sunday, so we will have some more time to spend together. I want to see how well my student learned!” Bryan grinned.

The two men fell into another kissey huggey session before returning to the dorm, and then just relaxed, and made out, on Bryan’s bed till suppertime.

The two men shared dinner together, enjoying each others company, then made their way back to the Dorm. They decided to watch some TV, so settled down onto one of the two couches in the rec room. After a few minutes, Darin sprouted an erection in his pants for no apparent reason. He quietly reached over, took Bryan’s hand and placed it on his bulge, causing Bryan to grin.

“I’d like to practice what you taught me today.” Darin spoke softly, smiling.

“I would like that,” Bryan responded. “Any place in particular you want to go to? It’s raining, so I think the woods are out.”

“How about your bed?” Darin suggested. “We can check and see if anyone is in the sleeping area. And afterwards, we can grab a shower, I’ve still got some cum on me from earlier”

As the two men made their way down to the end of the room where Bryan’s bed was, they knew they were the only ones in the room. It was only about 8:00 PM, and was a Saturday night, so not too many would be likely to be ready for bed this early.

Both men stripped down, completely naked, dropping their clothing on the floor beside the bed, and removing their shoes and socks. There was still some daylight coming through the windows, and Bryan walked down to the end of the room and turned out the bright overhead lights, leaving just the dim night lights on.

“We need to be as quiet as possible,” Bryan said, “or we may attract an audience!” Then added, “Darin, I can’t wait to feel you inside me!”

Darin, rolling the condom over his hard, leaking cock, “I sure hope I can please you, Bryan, as much as you pleased me this afternoon.”

Darin quietly lubed up Bryan’s crack, and hole, trying to remember just how Bryan had done what, when, earlier. He lubed his middle finger, and started to push it into Bryan’s hole, Bryan relaxed, allowing Darin’s finger somewhat easy access. Then he, remembering how Bryan did, pushed in a second and third finger, stretching Bryan’s rear entrance enough, hopefully, to allow his erection to enter.

Darin’s body was trembling, mostly from nervousness, as he tried to line his cock up with Bryan’s entrance. Bryan used Darin’s shoulders to try and raise his ass a little higher off the bed to make it easier for Darin to enter.

“You’re shaking like a leaf, Darin!”

“I’m sorry, Bryan. You know this is new to me.”

“Just take it easy, Darin. It’s only sex, you’ll be fine. Did you remember to lube the condom?”

“I did.” Darin answered, as he started to push the head of his cock against Bryan’s anus.

Bryan moaned a little in pleasure as Darin’s head popped through Bryan’s outer sphincter. Darin pushed more, sliding his cock about half way into Bryan’s ass.

“Whoa! Darin!” Bryan almost hollered. “Take it easy, let me adjust. Don’t push it all the way in now, gradually give me a little more, as I get used to it.”

“I’m sorry Bryan, I’ll try to do better. With you teaching me, I am sure to be a good fucker someday.”

“If you put your hands on my hips, and pull me to you, it will help you to stay in me. And feeling you in me is already feeling good. I’m ready for a little more, just do it gradually, ok?”

“I think,” Bryan said, “you need to angle your cock up a little, in order to hit my sweet spot.”

“Sweet spot?”

“Yeah, sweet spot, prostate. If you hit my prostate right, you will make me shoot, as I did to you earlier.”

“I’ll try,” Darin answered, “But I’m so hot right now!”

Both men were so wrapped up in their sexual encounter, that neither of them even noticed Luke and Mike arrive at Luke’s bed just 2 beds over from Bryan’s.

“So, slow it down,” Bryan said, “hold it off and try to rub my prostate. If we do it right, we can cum together.”

“You’re hitting it, Darin, just keep going. Oh my gawd, that’s feeling awesome.”

“I’m getting awfully close, Bryan. I don’t think I can hold off very long.”

“Just a few more bumps and I’m gonna blow. Oh shit, I’m gonna cum, in just a few se–cummmming, oh fuck that’s good.” Bryan gasped. “Slow up! I can’t take any more hits.”

“Just a few more pushes, aaaaannnnnnddddd,” Darin took a deep breath, “I just filled the condom. That was–exhilarating! I loved it.”

“Don’t pull out yet!” Bryan commanded. “I don’t want to lose the feeling of you in me. At least, not yet.”

“That’s a good feeling isn’t it Bryan.” Luke commented.

“Shit, we got company!” Bryan exclaimed, grabbing Darin’s butt and holding him in.

“We’re not company,” Mike stated, “You just got here ahead of us, thinking the same thoughts. Looks and sounds as if you’re about finished! The woods are a little to wet tonight, with this rain.”

Luke and Mike both started to undress, just disregarding the pair on Bryan’s bed. The two men started to kiss and hug, rubbing their hardening cock’s together, until Mike shoved Luke onto the bed, and then lay next to Luke, face to face, and cock to cock. Their hands busy, roaming all over each other bodies.

By this time, Darin had collapsed on top of Bryan, squishing Bryan’s cum between them. Having been caught, there was really no reason to hurry to get showered at this point.

“Let’s go ahead and shower now, Bryan. I need to dispose of this condom anyway, before it spills all over your bed. Now that I filled it, it won’t stay on my dick.”

Both men rose, went to their respective lockers, grabbed towels, soap and wash clothes, and headed to the shower.


“Fuck me, Mike!” Luke begged, “I want to feel you inside me.” Luke rose from the bed, went to his locker and retrieved the lube and a condom, and then handed them to Mike.

“Okay if I ride your horse tonight?” Luke asked.

“Ride away, baby,” Mike answered, smiling, as he rolled the condom onto his dick.

Luke carefully lubed Mike’s condom covered cock, his first two fingers, and his crack and man pussy, using his fingers to work his hole a little in preparation.

Then he straddled Mike’s torso, lining his hole over Mike’s pole, and started to lower his hole over the pole slowly sliding down, pushing onto Mike’s shaft. It seemed to Luke, that once the head popped in, the rest went easier.


The hot water of the shower felt good spraying on Darin and Bryan’s bodies. They migrated to soaping and scrubbing each other, once they had both done their own face and hair. As Bryan was washing Darin’s private areas, Darin spoke.

“I remember, as a little boy, how good it felt when Mama gave me a bath, and she always made sure my penis and scrotum were cleaned well.” Darin reminisced, “And it always felt so good, and still does, even when you do it.”

“I wonder,” Bryan mused, “being that our mom’s were women, if they even realized how good it feels to little boys to be tenderly washed down there? And I have to agree, it does still feel good today!”

As the two men finished their showers, Darin couldn’t resist, while still under the running showers, putting his arms around Bryan, drawing him close, their cocks touching, and placing his lips on Bryan’s and finding no resistance at all, just reception. In just a relatively short kiss, both men felt their cock’s swelling.

“Let’s get dry, and go back and lay on your bed.” Darin suggested.

“Sound’s like a plan, man!” Bryan commented. They stepped out of the shower, and proceeded to dry off.

* * * * * * * *

By this time, Luke and Mike were really into it. Luke was riding Mike’s cock like a pro, shifting a little now and then, to keep Mike’s cock where it was tapping on Luke’s prostate.

“Do me a favor Luke?” Mike asked. “Pull off when you are ready to shoot, and let me take it in my mouth. I’m gonna blow pretty soon myself.”

Luke, riding even harder, hitting his prostate on every down stroke, noticed that Mike was breathing really heavy.

Darin and Bryan had returned and were just watching the ‘show’ from the view offered them from by Bryan’s bed, both starting to get hard again.

“Oh god, baby, I’m fuckin’ close! I’m about to fill that condom. Oh, fuck, here it comes!” Exclaimed Mike.

Luke bottomed out, the head of Mike’s cock nudging his prostate, and he started to grip Mike’s cock by tightening, causing Mike to spasm.

“Ooooohhhhh Gaaawwwwdd!” Mike hollered, “That’s done me in! I just lost it all! Baby you close?”

“Open up, Mike, I’m about to nut!” Luke pulled off Mike’s cock, ramming his own into Mike’s open and waiting mouth. No sooner was Luke’s uncut manhood comfortably accepted inside Mike’s mouth, he started to pulse.

“Here you go, baby, be ready. Oh, Oh, Oh, Sheeeeeet!” As Luke Gasped, he could feel spurt after spurt of his man juice, escaping his cock and going into Mike’s warm and waiting mouth. Mike was swallowing every spurt, almost gagging on the first couple of spurts. Then, the last he milked out of Luke he rolled around in his mouth, spreading the flavor around.

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One thought on “Young, Gay And In Prison Pt 22

  1. Penfire says:

    Well hot the Darin gave his virgin 🍒 to Bryan. Darin loved the sex and now can’t get enough of Bryan. Luke has a major decision to make, Mike or his old girl friend.

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