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Naughty Boy Stories


These stories are about adults only and intended for adults only!

I've created some tasks at to help us boys improve our behavior. Username: ZacLoughty

Zander - Chastised



By Zac Loughty

This is a fictional story about adults, for adults only

The author would like to thank his Discipline Monitor for his ‘encouragement’ to get this story finished, and for proofreading this story.


Sir wants to have a ‘chat’ with me. The last time we had a ‘chat’, I wound up wearing this ankle monitor to ensure I didn’t skip any of my college classes. He also monitored me to ensure I didn’t arrive late.

Skipping a class would cost me a weekend in our cell. I’d be grounded. Thankfully, my friend Chad helped keep me on track so that didn’t happen. He didn’t want me grounded and unable to spend time with him. The same Chad caused me to be late for a class one day last semester. I had to spend a night in the cell. That was called a ‘detention’. It wasn’t a big deal.

Sir has summoned me to his library for this chat. I take a deep breath, and knock.

Knock. Knock. Knock.


“Um… you wanted to have a chat with me, Sir?”

“Yes boy, come on in and take a seat.” Sir motions to a chair across from him.

“Yes Sir, thank you, Sir.” I sit down.

“I’ve reviewed your grades from last semester, boy.”

“Yes Sir. As you can see, I didn’t flunk any of my classes, Sir. I really appreciate your help, Sir. This ankle monitor really discouraged me from skipping a class or being late, Sir.”

“You received an ‘A’ in your programming class.”

“Yes sir. I really enjoyed programming, Sir.”

“You received a ‘B’ in your psychology class.”

“I was surprised how difficult psychology is, Sir. There’s a lot of terminology.”

“You received a ‘B’ in your English class.”

“That was Introduction to Writing, Sir. The teacher was a real stickler for details, Sir.”

“And then you received a ‘C’ in your geography class.”

“Yes Sir.” I hang my head. “I never expected geography to be that difficult, Sir.”

“Well, I’m disappointed, boy. I know you can do better. Last semester you told me you wanted to become the best teacher you could be. You assured me you were willing to put in the hard work and sacrifice your free time to make it happen.”

I knew that would come back to haunt me. Crap!

“Um… yes Sir.”

“Well, are you willing to put in the hard work or not, boy?”

“I’m willing to work hard, Sir. I want to be the best teacher I can be, Sir.”

“I’m happy to hear that, boy! If you’ll recall, I made you another offer last semester. It involved a chastity cage. I believe you should reconsider my offer, boy. Again, I can’t promise you straight A’s, but I know you’ll be trying your best to keep your boy nub out of that cage.”

“Yes Sir.” I sigh heavily.

“If you try the chastity cage, I’ll remove your ankle monitor, boy. I don’t believe you’ll be skipping any classes or arriving late when your nub’s freedom is on the line.”

“You’d remove my ankle monitor, Sir?”

“That’s right, boy.”

“I need to talk this over with Chad, Sir.”

“I imagine Chad won’t be in favor of this, boy. You’ll need to convince him.”

I need to convince Chad I should have my dick locked up? Um… not likely.

“Um… I’ll talk to him, Sir.”

“Boy! Don’t look so glum! You need to have confidence in yourself! If you keep up with your classes, your nub remains free!”

“So, I provide you with the syllabus from each of my classes.”

“That’s correct, boy.”

“I’ll need to take careful notes in class and provide them to you.”

“Correct again, boy.”

“I need to complete all the assigned and recommended reading and outline every chapter.”

“Yes boy.”

“I’ll also need to turn in both required and recommended homework to you.”

“That’s it, boy.” Sir’s smiling at me.

“Um… when will I sleep, Sir?”

“You’ll be able to sleep, boy. You just won’t have time for much else.”

“No, I guess not.”

“Think it over carefully, boy. I look forward to learning your decision.”

I really don’t have a choice. I know I need to ask for the chastity regimen. I gotta talk to Chad.

“Thank you, Sir. I’ll let you know my decision, Sir.” I stand up and leave the library. Chad’s coming over tonight. I can speak with him then.

* * * * *

Chad and I are on my bed, feeling each other’s boners through our pants, and kissing.

Chad breaks away and asks, “So what did you want to talk to me about?”

I look into his eyes.

“What’s wrong?”

“Um… I have some good news!”

“If it’s such good news, why do you look like you’re gonna cry?”

“Um… I’m gonna get this fuckin’ ankle monitor off!”

“Oh… great! That’s awesome! So, you finally told the old guy to go screw himself?”

“No. There’s kind of a catch…”

“Oh, oh. What’s the catch?”

I take in a deep breath and let it out.

“Zand? What’s the catch?”

“If I fall behind in my classes, my dick gets locked in a chastity cage.”

Chad stares back at me in disbelief. 

“Say what now?”

“Um… if I fall behind in my classes, Sir will lock a cage on my dick.”

“No.” Chad shakes his head.


“No, Zand. That’s fucking crazy! Fuck him!”


“That’s ludicrous, Zand. Tell this fucker to go fuck himself!”

“Chad, he isn’t making me do this.”

“Great, don’t do it!”

“Chad, he’s just trying to help me.”

“Great, he can hire you a tutor.”

“He wants me to really learn the material so I can be a great teacher.”

“You’re gonna be a great teacher, Zand. You’re the most caring, loving guy I know. You’ll do everything to help your students succeed.”

“But I gotta know what I’m teaching, Chad.”

“You’re actually considering this?” 

“Um… hey… I know this is too much to ask of you. You deserve better, Chad. You need a guy with a dick.” Tears well up in my eyes and flow down my cheeks.

“Whoa! Hey, hey, hey, it’s okay, Zand.” His arms wrap around me in a tight hug. I sob into his shoulder.

“Zand… look at me.” He holds me at arm’s length.

“I need your heart. I need your caring. I need your love. Your dick is just a fun extra. You’re really serious about this, aren’t you?”

“I kinda am, Chad. I want to do well in school. I just don’t seem to have the self-discipline to do it on my own. Maybe with my dick’s freedom on the line, I’ll buckle down and study.”

“What’s involved with this chastity shit?”

“I gotta provide Sir with the syllabus from each of my classes. That’s so he can monitor the due dates and track my progress.”

“Okay. No big deal.”

“Right. Then, I need to take careful notes in class and show them to him.”

“Okay, no problem.”

“Right. Then, I need to do all the homework, both required and recommended and show it to him.”

“All recommended homework too? Could be a challenge, bro.”

“I know. Then, I gotta do all the required and recommended reading and outline every chapter and show it to him.”

“Whoa! Outline every chapter? Dude, that’s time-consuming.”

“I know, but Sir says it’ll help me be more prepared for tests. I won’t need to reread any chapters. All I’ll need to do is study my outlines.”

“I guess that’s true. But dude! How long is that gonna take you?”

“A long time.”

“So, how does your dick wind up in a cage?”

“If a fall behind in any class, my dick gets locked up until I catch up.”

“Zand! That’s fuckin’ crazy! Your dick could be locked for the entire semester!”

“I know. I don’t see any way my dick’s gonna remain free.”

“When are we gonna go out dancing and have fun?”

“After the semester’s over?”

Chad lets out a heavy sigh.

“If this is what you want to do, I’ll support you. I have my own classes to worry about, but I’ll help you as much as I can.”

“You’re the best guy in the world, Chad. I can’t believe I was lucky enough to meet you.” My arms wrap around him and gather him in a tight hug.

“I guess you can come over and study with me. But we aren’t gonna be able to mess around all the time.”

“Especially not if there’s a cage on your dick!”

“We can still sleep together,” I offer.

“Yeah, that’s nice. I sleep better with your warm body next to me.”

“Besides, maybe I’ll be able to keep up with everything. Then, my dick will be free.”

“It’s gonna be very difficult for you to keep up with every single class, Zand.”

“I know.”

“Well! If you’re gonna go for the chastity regimen, I guess I better treat your guy right while he’s free!”

“That’s not a bad idea,” I agree, chuckling.

Chad moves down to my crotch. He undoes my belt. Then, he unbuttons and unzips my pants. I raise myself so he can take ‘em off.

He nuzzles my dick through my boxers. It immediately rises to the occasion. His mouth wraps around it and gently bites it. He moves to take off my boxers. I raise my butt to help him out. My dick pops out.

“I can’t imagine your beautiful cock being locked in a cage.” His wet, velvety tongue glides along my shaft from my balls to my head.

“How can these plump, juicy balls be denied shooting their load?” His lips deliver wet, delicate kisses to my testicles. I tousle his blond hair.

He buries his nose in my sack.

“God, you smell good! You’re such a stud, Zand.”

Long licks massage my hairless sack.

“Oh… you’re treating my balls real nice.”

My head disappears in his mouth. I close my eyes as his tongue tickles my frenum. His eyes stare straight into mine as he sucks me.

More of my shaft disappears into his mouth until I hit the spongy softness at the back of his throat. He buries his nose in my pubes and inhales.

As he bobs up and down on my cock, my head rams his gullet. My shaft glides along the suede-like pillow of his tongue.

“Ah…” I gasp.

His lips push in on my shaft, grasping me securely me in his warm, wet mouth.

“Ah… I’m gonna cum, Chad.”

The corners of his mouth attempt a smile. His eyes sparkle. He wants my cum.

I close my eyes; I begin to pant. My balls tighten up.

“I’m cumming!”











“Oh… that was great, babe!” I mess up his hair.

He smiles and licks his lips as he laps up cum from my head.

“Gotta get you all cleaned up, Zand.”

“You’re doing an excellent job there.”

He lays his face next to my shaft.

“I’m gonna miss your cock, Zand.”

“Hey! Maybe I’ll be able to keep up with my classes all semester. Then, my cock won’t get locked up.”

“You gotta keep up with your classes, that’s all I can say.”

* * * * *

Well guys, it’s the Saturday before my first day of classes on Monday. I’m going to tell Sir that I want to try the chastity regimen. I figure Chad and I have this one last weekend to mess around until I need to keep up with my classes, so my dick remains free.

Sir is in the library. I approach the door and knock.

Knock. Knock. Knock.

“Yes?” Sir asks.

“Um… Sir?”

“Zander! Come in boy, come in! Have a seat!” Sir waves me in and points to a chair across from him.

“What can I do for you, boy?”

“Um… I’ve decided to take you up on your offer regarding the chastity regimen, Sir.”

Sir’s whole face displays pure joy.

“That’s wonderful news, boy! Rod! Get in here, boy! Zander has decided to take the plunge!” He stands up and offers me a hug.

I stand up and fall into Sir’s embrace. Sir is the best hugger ever! His arms wrap around me tightly. My face gets buried in his chest.

“You won’t regret this, boy! Your grades are going to soar! You’ll be on the Dean’s List, boy!”

“That would be great, Sir!” I admit.

“What’s Zand doing, Sir?” Rod is standing in the doorway.

“Zander’s volunteered for our chastity regimen, Rod.”

“Zand! That’s excellent news! Congratulations, boy!” Rod’s arms wrap around me from behind.

I’m glad I’ve made them both so happy.

Sir breaks off his hug, places his hands on my shoulders at arm’s length, and looks me directly in the eyes.

“Boy! We must remove your ankle monitor! You’re not going to be needing that anymore!”

“No, Sir! Please remove my ankle monitor, Sir,” I say happily. This definitely was the best decision.

“Absolutely, boy!” He turns to the library shelves, opens a drawer, and retrieves a couple tools.

“Just put your right foot up on this end table here, boy. We’ll have that monitor off in no time.”

“Yes, Sir! Thank you, Sir!” I can’t believe I’m finally getting this monitor off my ankle!

“We’ll just pop off this outer cover,” Sir says as he bends down and uses a screwdriver to remove my monitor’s cover.

“Then, we’ll snip this little tie here.” Sir takes a pair of odd-looking pliers and snips the tie.

“Then, we’ll unscrew and remove it!” Sir twirls his screwdriver a few times. Then, he grabs my monitor and opens it up.

“Voila! You’re free, boy!” 

“Thank you, Sir!” I pull my ankle free of the monitor. Wow! It’s been on a long time!

“You’re welcome, boy!” He returns the tools to the drawer. Then, he opens another drawer and removes something.

“It feels good having your ankle back, doesn’t it, boy,” Rod says.

“It sure does, Boss,” I admit. I’m all smiles.

“Now, it’s time to get you sized, boy. Rod has kindly offered to assist me. We’ll just need you to remove your clothes.” Sir and Rod stare at me.

“Um… sized… Sir?”

“Yes, boy. We need to ensure your chastity cage is properly sized. If it’s too small, you may suffer from edema. If it’s too large, it may fall off. We want the size to be just right.”

“Yes, boy. Fit is everything. We’re going to be sure we have the best fit,” Rod adds.

“Um… but the semester hasn’t even started yet. I’m not behind on anything.”

“We know that, boy! We aren’t saying you’re behind. We need to ensure we have your best fit in the event we need to apply your chastity cage,” Sir assures me.

“Oh. Well, I guess that’s okay then,” I agree. I remove my shirt and pants, carefully fold them, and set them on a chair. Then, I remove my boxers. I’m naked except for my padlocked collar.

“Perfect, boy! Let’s see what we’re working with here, Rod,” Sir says, handing Rod a box.

They both get down on their knees and move in to inspect my groin. Well, this is embarrassing. Rod puts on a pair of rubber gloves!

Snap! Snap!

“Right! Let’s see what we have here,” Rod says, lifting my dick and fondling my balls.

“Perhaps we should start with a medium-large ring,” Sir suggests.

“I think his little nuts will slip right out of that, Sir,” Rod says.

“Well, I don’t want them to turn purple and fall off,” Sir says with concern.

What’s this about my balls falling off?

“Let’s try the medium-large ring, Sir,” Rod agrees.

Sir hands Rod a metal ring.

“Um… that’s medium-large?” I ask. It looks so small!

“Yeah, I think it may be too large, but we’ll try it,” Rod says.

It’s too large?

Rod holds the ring up to my scrotum, puts a bit of lube on his fingers, and starts pulling my skin through the ring.

“It’s important that I pull enough of your boy sack through the ring to give your nuts someplace to go,” Rod explains.

Now, where are my nuts going?

He reaches behind the ring. His fingers coax my left ball toward the ring. He applies pressure on my ball until…


It crosses the ring’s threshold and winds up on the other side. There’s a tug on my sack as Rod pulls more of my scrotum into the ring with my testicle.

“There’s gotta be enough sack for both of your boy nuts, boy,” Rod tells me.

The fingers of Rod’s other hand maneuver my right ball toward the ring. There’s pressure… pressure… pressure…


It jumps into the ring with its brother.

Rod moves my balls from side to side in the ring.

“See, Sir? I think there’s just too much play here,” Rod concludes.

“Um… it feels like there’s barely enough room for them in there,” I suggest.

“Oh, there’s plenty of room, boy. That’s the problem. You don’t want one of your little boy nuts to slip out between the cage and ring, boy. That hurts like heck, believe me!” Rod says.

Sir moves in for a closer look at my ringed balls. My junk isn’t used to this much scrutiny!

“You may be right, Rod. Let’s try the medium ring,” Sir agrees.

Rod’s fingers move in on my unsuspecting balls. There’s pressure as he pops first my left ball, then my right ball out of the ring.

Sir hands Rod and even smaller ring! Jeesh!

“Um… I don’t think my balls are going to fit in that one, Rod,” I advise.

“Nonsense, boy! Your boy nuts will feel right at home in this ring,” Sir assures me.

Rod holds the smaller ring against my scrotum, pulls my skin through, pops my left nut in, pops my right nut in, and moves them around.

“We can try this, Sir. He might need a medium-small,” Rod says.

An even smaller ring? My nuts barely fit in this thing!

Sir scrutinizes my ringed balls. 

“Let’s stick with this one for now, Rod,” Sir concludes.

“What cage size were you thinking, Sir?” Rod asks.

Gulp! I guess that’s why it’s called a chastity ‘cage’.

“I was thinking we’d start with a small cage,” Sir suggests.

Um… excuse me… small? Who’s small? What’s small?

“That’s pretty big, Sir. I’d recommend a nano to start, Sir,” Rod suggests.

Um… if it’s small, how can it also be big? What’s a nano?

“You think so, Rod?”

“It’ll be easier for him to adjust to a nano, Sir. It pretty much eliminates the ability to get hard,” Rod says.

Gulp! It eliminates my ability to get hard? That’s not good.

Sir hands a hunk of metal to Rod. He puts some lube on my cock and puts the cage against it. That’s where they think my penis is going? In that tiny thing? No way!

“Um… that’s way too small for my penis,” I state.

“Nonsense, boy! Your little nub will feel right at home in its cage,” Sir tells me.

I look at the bars on the cage. There would be two vertical bars over my head on either side of my pee hole. Then, there’s one horizontal bar covering my head except for my pee hole. The head of my cock would be jammed up against those metal bars. My cock starts to chub up.

What the fuck? Why is my cock getting excited about being locked in that tiny cage? There isn’t anything sexy about it!

“Oh, it looks as if someone’s getting excited to wear his new chastity cage, Rod,” Sir says.

“That’s no problem, Sir. I have the perfect solution to that,” Rod says. He gets up, opens a drawer in the bookcase, and returns with a magazine.

“What do you think of these pics, Zand?” Rod says, opening a Playboy centerfold.

“Eww!” I say with disgust.

“Get a load of them boobies!” Rod says.

“That’s gross, Rod!” I protest.

“Don’t you want to squeeze them, Zand?” Rod teases.

“No. I don’t want to go anywhere near them!” I declare.

“I know what you want, Zand. You want that thing between her legs,” Rod says.

“Eww! My penis isn’t going anywhere near that!” I assure him.

He drops back to his knees and places the cage against my rapidly deflating cock.

He applies constant pressure, using the cage to push my cock back toward my body (and the ring).

“This is where it gets tricky, Zand. I gotta ensure I don’t pinch you.” 

Two metal prongs advance to match up with holes in the ring. The skin on my cock is bunched up and in the way. It doesn’t look good.

Rod uses his thumb and index finger to pull my cock skin down and out of the way of the prongs. He pushes the prongs into the holes. The skin on my cock is safe.

I was so concerned about those prongs, I didn’t notice the cylinder on top lining up.

“I think we’re ready for the key, Sir,” Rod says.

“Here you go, boy,” Sir says, handing Rod a long key with a tiny piece at the end of it.

“You see this bit at the end, boy?” Rod asks me.

“Yes, Boss,” I reply.

“This goes right in here,” Rod tells me as uses the key to slide the end into the cylinder on top of the cage. He turns the key and withdraws it. 

“That’s called the locking piece, boy,” Rod informs me. “That stays in there, locking the cage to the ring.”

“You mean it’s locked on?” I ask. How can that little piece of metal lock my dick in this cage?

“Your nub’s been caged, boy,” Rod tells me with a smirk.

I reach down, grasp the cage, and try to pull it off. It’s stuck.

“You’re all set, boy,” Sir tells me.

“So… you know which size chastity cage I should wear?” I ask.

“No,” Sir corrects. “We THINK we know what size chastity cage you should wear. It will take a number of days to ensure we have the right size.”

“Um… days, Sir?” 

“Yes, boy. We’ll let you wear this cage for a few days and watch for problems. If you notice any swelling, let us know immediately,” Sir warns me.

“Um… I thought I wouldn’t be locked until I fell behind in my studies, Sir,” I protest.

“This is a one-time thing, Zand,” Rod assures me. “Next semester you won’t need to be sized at the beginning.

“This will be great, boy!” Sir assures me. “You’ll hit the ground running! You’ll start in on your studies right away to ensure your boy nub’s let out of its cage at the first opportunity.”

“But… I kinda promised Chad that we could still mess around this weekend,” I whine.

“Won’t HE be surprised!” Sir says with a laugh.

“He’s going to LOVE your cage, Zand. It looks real pretty on your nub,” Rod says.

I stare at my imprisoned cock. It looks so pathetic and helpless behind the metal bars of its cage. Will it ever forgive me?

“Don’t look so glum, Zand!” Rod says. “Your grades are gonna be amazing, dude! Your father’s gonna be shocked.”

“It’ll be okay, Zander,” Sir assures me. “As soon as we know this cage fits, we’ll remove it as long as you’re keeping up with your classes. I promise.”

I’m in shock. I don’t know what to say. What am I gonna tell Chad? Crap!

“Um… I think I’m gonna go to my room now if that’s okay,” I say.

“Of course, boy! We’re all done here,” Sir says. “Let us know if you have any problems at all, boy.”

The problem is that my cock is locked in a cage!

I pick up my clothes from the chair and go back to my room. I close the door. I sit down at my desk and stare at my locked-up cock.

I pull the cage forward. It grabs the skin of my cock with it. I try to get my fingers between my body and the cage to try to pull my cock out the back. I’ve heard of guys doing that before. But the cage is so narrow, it seizes my cock and won’t let go.

I turn the cage sideways to examine my trapped balls. Jeesh! The gap between the ring and the cage is tiny… no more than ¼” thick! There isn’t any way my balls can fit through there. They’re stuck dangling under the cage.

I try to stick my pinky through the gap between the bars on either side of my piss slit. No go. The slot just isn’t big enough.

My cock stares back at me with its one eye. It feels betrayed. It doesn’t give a shit about my grades.

Knock. Knock. Knock.

Now what?

“Zand?” It’s Rod.

“Yes, Boss?” I answer.

“Can I come in? You can drop the Boss stuff.”

Wow! This must be serious! Rod told me to always address him as Boss.

“Yeah, okay.” I really just want to be left alone with my locked-up penis.

Rod enters my room and takes a seat on my bed, facing me.

“Hey… um… you’ll get used to it, Zand.”

“I don’t think I’m ever gonna get used to having my penis locked in a cage, Rod.”

“Well, it’ll get okay. You’ll def want the fuckin’ thing off your cock, but it isn’t the end of the world.”

“What’s the longest you’ve gone wearing a chastity cage?”

“Three months.”

“Three months? Three months?” My stomach does somersaults.

“I’m not gonna lie. It was tough. But guess what! I got straight A’s that semester.”

 “What did you tell guys?”

“I didn’t go out. But you’re lucky… you have Chad. I think he’s a good guy, Zand.”

“I know he’s a good guy. He’s supporting me while I do this. But he thinks we’re gonna have sex tonight.”

“He’ll understand. He doesn’t want anything to happen to your penis. He wants your cage to fit properly.”

“He wants me to fuck him!”

“That’s not gonna happen.”

“Tell me about it.”

“Look, Sir holds your key. If you ever get to a point where you can’t take it anymore, just ask him to allow you out of the chastity regimen.”

“He’d do that?”

“Zand, Sir NEVER will do anything against your will. He knows you want to improve your grades and he believes the chastity regimen will help you. But if you ask to be let out, he’ll let you out. He’ll be disappointed, but he’ll let you out.”

“Oh. I guess I forgot that.”

“Now, if I were holding your key, I’d tell you to suck it up and deal,” Rod says, smirking.

I smile. Rod’s just trying to cheer me up.

“When’s Chad coming over?”

“He’ll be here soon.”

“I’m sure you’ll both find ways to have fun.”

“I hope so.”

Rod leaves, closing the door behind him. I purchased a couple textbooks for my classes this semester. I open one and start reading it. I decide to throw on a pair of shorts so I don’t have to see my imprisoned dick.

* * * * *

Knock. Knock. Knock.


“Hey, Chad, come in.” Chad lets himself in and shuts the door.

“Um… Rod told me that your cock’s locked up. I’m sorry.”

“Not as sorry as I am! I wanted to pound your hole tonight!”

“Ha! Ha! That’s okay, I’ll find ways to cheer you up.”

“That’s gonna be difficult, babe.”

“Aww. I want to see it. Can I see it?”

“It’s really pathetic, Chad.”

“I can’t imagine your cock ever looking pathetic.”

I’m embarrassed to show Chad my locked-up dick. But I guess I can’t put it off forever. I strip off my shorts.

“Wow! Your cock looks like a caged beast, Zand! It looks really hot!”

“It looks small, pathetic, and defeated, but that’s okay.”

“No, Zand, I mean it! Wow! It’s really testing the confines of its cage.”

“It’s no match for the metal bars, bud. It’s stuck.”

“Hey! I can still lick and suck on your humongous bull balls!”

“You’ll have to be careful, bro. This cage hurts when my guy attempts to get hard.”

“I’ll take it easy, Zand. So, what can I do for you tonight?”

“Um… can we just cuddle and go to sleep?”

“Sure, Zand! Can I be the big spoon this time? I hardly ever get to be the big spoon.”

“Yeah, that sounds great, dude.”

We brush our teeth and get ready for bed. When we get back to my room, we strip out of our clothes and hop in bed. We kiss slowly and passionately. I have to take a break when my cock tries to get hard; it just hurts too much. When we’re ready to go to sleep, I roll over on my side and Chad lies behind me. The weight of his arm over me comforts me. Our hands find each other. Our fingers intertwine. The warmth from his body is cozy. His cock rests against my ass cheeks.

“What did Rod say about me?” I ask.

“Nothing much. Just that your cock’s locked up. And… um… that you’re vulnerable, which is okay.”

Wow, Rod knows me better than I thought. I’m loved and secure with Chad’s body wrapped around me. I go right to sleep.

* * * * *

“Ahhhhhh!” I wake up in extreme pain.

“Zand, what’s the matter?”

“My dick’s gonna explode!”

Chad turns on the light.

We look at my cock. It’s trying to burst out between the bars of its cage. It’s purple and angry! The metal bars are digging into my sensitive head.

“Take deep breaths, Zand!” Chad advises.

“Fuck! Fuck! Fuck! Fuck! Fuck! God, this hurts!”

“Shush, babe. Calm down. Think about ocean waves, or a forest, or a meadow or something.”

My poor cock wants to become erect. Blood is pouring into it, but the fucking cage won’t let it grow. All that blood has nowhere to go. I suck in as much air as my lungs will hold. I let it out slowly.

“That’s right, take a deep breath and let it out slowly,” Chad counsels.

“Ow!” I give Chad a pouty face.

“Aww, my poor baby. Your cock doesn’t want to be tamed, Zand.”

“I know! It needs to be free to get nice and hard so it can fuck!”

“But you need to think of other things now so it will give up and stop fighting its cage.”

“I know, I know.” I take in another deep breath and slowly exhale. Chad massages my neck and shoulders.

“Calm down, babe,” he says.

“It’s gonna take some time for it to learn its new limitations,” I admit.

“Exactly. Once it learns its boundaries, you should sleep better,” Chad agrees. He rubs my arm.

My cock gradually calms down. It fought the cage and lost. I gotta try to control these nocturnal erections. I don’t want to keep waking Chad.

I fall asleep with Chad’s hand gently rubbing my arm.

* * * * *

The following Tuesday…

Knock. Knock. Knock.


“Um… Sir?”

“Zander! Come on in, boy! What do you have for me?”

“These are the syllabuses for my Tuesday, Thursday classes, Sir.” I hand them to him.

“Wonderful! So, do I have a syllabus for each one of your classes now, boy?”

“You do, Sir.”

“Great! That’s all I need, boy.” He begins reading one of the syllabuses.

I just stand here looking at him.

He looks up.

“Anything else, boy?”

“Well Sir, I was wondering if you would please remove my chastity cage, Sir.”

“Is something wrong, boy?”

“Well Sir, it’s just that I believe we’ve found the right fit now.”

“Let me see, boy.” 

Crap! I’m still embarrassed to show my caged dick. I unbuckle and unbutton my jeans, unzip, and pull them down with my boxers.

My cock likes the attention, though. It presses up against the bars of its cage.

“Let’s see how your nub is doing, boy.” Sir moves in to closely inspect my caged dick. His hand moves the cage around so he can check my cock. His other hand grabs my sack and moves my nuts around under the cage. He examines my sack.

“I believe you may be right, boy. This size ring and cage appear to fit your boy nub well.”

“Oh, I’m really happy to hear you say that Sir. I appreciate how you wanted me to wear the cage for a while to ensure we got the right fit. If I begin to fall behind in my studies, it’s great to know I’ll have a chastity cage that fits perfectly.”

“You’re welcome, boy. I don’t want you to wind up with sores on your boy nub or nuts.”

Sir leans back in his chair and returns his attention to the syllabus.

“So, if you could just get the key and unlock me, I’d really appreciate that Sir.” As soon as he unlocks me, I’m gonna stroke out a huge load!

“Boy, according to the syllabuses you’ve handed me so far, you have a lot of work to do before I free your nub.”

“Huh?” What? I just started. I’ve only attended my first classes.

“You need to read a minimum of the first two books in your literature class, boy. Your calculus class requires you to read the first two chapters and do all the exercises, boy. I don’t need to remind you that you must outline those chapters. Should I go on with the requirements of your other 3 classes, boy?”

“But… but… I just started, Sir. I can’t be behind already.”

“But you ARE, boy! You need to get busy. You shouldn’t be standing around here with your pants down, boy. You need to be reading, outlining, and doing those exercises. Get to work, boy. Come back next week. We’ll see if you’re caught up enough then.”

“Um… next week, Sir?”

“Boy, there’s no way you’re going to get caught up in less than a week. Come back in a week. I’ll check your progress then.”

“A… a week, Sir?”

“I know that’s soon, boy. But I have faith in you. I’m sure your little nub will urge you to work hard and get caught up, boy.”

I look at my sorry nub, hopelessly locked behind metal bars.

“Don’t look so glum, boy! This is a great opportunity. The first few weeks of classes are very important, boy. Work hard now so you won’t need to work as hard at the end.”

“But… but what about Chad, Sir?”

“Chad will be fine, boy. He’s a fine young man. I expect the two of you will learn to enjoy each other in different ways.”

“Um… different ways, Sir?”

“It’s not all about sex, boy.”

I just stare at him. He’s not gonna unlock my dick?

“Well, if you’ll excuse me boy, I have some syllabuses to read.” He turns back to reading the syllabus.

I guess I’ve been dismissed. I pull up my boxers and jeans. I fasten my jeans and buckle my belt. My gut aches like it’s been punched. I turn, exit the library, go into my room, and dive face-down on my bed.

OUCH! My trapped balls hurt! I quickly roll over face-up. Should I just give up and tell Sir I want to abandon the chastity regimen? I picture Sir’s disappointed face. I let out a massive sigh. Fuck!

I take down my jeans and boxers and stare at my cock peeking out from behind bars. I’m horny! I grab my caged package and shake it. My cock starts to chub up, but rams into the bars. Ouch! I pull the cage away from my body as much as my balls will allow. I attempt to fuck the cage. The cage is too small. There isn’t any room at the end for my cock to get any friction… enough friction to cum. Crap!

I roll out of bed, take a seat at my desk, and open my calculus book to Chapter 1.

* * * * *

More than two weeks later…

“He didn’t unlock you?” Chad asks.

“Nope. Says I need to read and outline more chapters.”

“FUCK! I really want to feel your dick up my ass.”

“Not as badly as my dick wants to be in your ass.”

“That’s probably true. I won’t argue with you.”

Chad pushes me backward onto my bed. He climbs on top of me, staring into my eyes.

“Now what?” 

“Your eyes are beautiful.”


“I mean it, Chad. You have incredible eyes.”

“Um… okay. Thank you.”

“They show how kind and caring you are.”

“Aww, thanks, Zand. That’s really sweet.”

“I mean it, Chad. You’re the most caring, loving, kind guy I’ve ever met. I’m very lucky you’re my friend.”

“Wow! Thank you, Zand.” He moves in for a kiss. We suck face for a while. We have fun tongue wrestling. I break off.

“You have a great smile too.”


“Really. I can be depressed, but as soon as I see your smile, I feel better.”

“Jeesh, Zand. That’s a really nice thing to say!”

He moves in for another kiss, then breaks off.

“I miss your cock, but I miss something else more.”

“Really? You miss something more than my cock?”

“I miss Boss.”


“From the cell. I mean, I don’t need to share the cell with you again cuz your bed is WAY more comfortable than that mat. But I miss Boss.”

“Bossy Boss?”

“Ha! Ha! Yeah, bossy Boss!”


Chad’s eyes sparkle. I love that mischievous grin.

“Strip, boy!”

“You want me to take off my clothes, Boss?”

“I do! NOW!”

“Yes, Boss.” Chad giggles as he removes his shirt. He removes his shoes and socks. Then he pulls off his pants. He stands before me in his boxers.

“What part of ‘strip’ didn’t you understand, boy?”

“Yes, Boss.” He pulls down his boxers and steps out of them. His erect cock pops out. I’m jealous.

“That’s better, boy.” I stand up next to the bed.

“Take off my shirt, boy.”

Chad lifts my t-shirt. I raise my arms to help him out. He pulls it over my head and off.

“Hmm… you smell good, Boss.” He sticks his nose in my pit.

“You like my stink, boy?”

“I do, Boss. You smell like a man.” He buries his nose in my pit and takes deep breaths.

“I got something else you can smell, boy. Take off my pants.”

“Yes, Boss.” Chad smiles as he undoes my belt, unbuttons my jeans, and unzips them. He pulls them down to the ground and I step out of them. He nuzzles my balls and cage in my boxers.

“Okay boy, remove my boxers.”

“Yes, Boss.” He grabs the bottom of them and pulls them down. I step out of them.

He sticks his nose in my trapped ball sack and takes a deep breath.


“You like the stench of my ball sweat, boy?”

“I do, Boss!”

“Lick and suck on them, boy.”

“Yes, Boss.” The softness of his tongue caresses my snared testicles. 

I’ve trained my cock not to get too excited. Still, it notices the attention my balls are getting. My cage gets… tight.

He takes my left teste into his mouth. He rolls it around and massages it with his tongue. He does the same to my right ball.

My cock tells me it wants to pee. Then, a thick drop of pre appears in my piss slit and starts heading to the floor. Chad is quick to move in and lap it up.

“Hmmm… yummy!” He licks his lips and smiles.

“Okay, come up here, boy.” I motion for him to stand up.

He does.

“Turn around.”

He turns his back to me.

I move up behind him and wrap my arms around him. I hold him tight.

“Umph! You got me, Boss.”

“I got you, boy!” I move in close to his right ear. I lick his ear lobe.

“Hee, hee, hee. That tickles!” 

I bite it playfully. Then I whisper…

“Here’s what you’re gonna do, boy.”

“What, Boss?”

“First, once I let you go, you’re gonna rim my ass, boy.”

“Yes, Boss.”

“You’re gonna really get your tongue up in there, boy.”

“Yes, Boss.”

“While you’re up there, you’re gonna take your hand and stroke your cock.”

“Stroke my cock, Boss?”

“That’s right, boy. You’re gonna get it nice and hard.”

“Nice and hard, Boss.”

“Then, you’re gonna slip on a condom and lube up my hole and your cock.”

“Yes, Boss.”

“Once you’re lubed up, you’re gonna slide your fuck stick up my ass.”

“Oh wow, Boss!”

“You’re gonna fuck my hole hard and fast, boy.”


“You got that, boy?”

“I think so, Boss.”

“Get to work, boy!” I let my arms down and turn to face the bed. I bend over it, sticking my ass out nice and far.”

Chad kneels behind me. His tongue glides over my rosebud.

“That’s nice, boy.”

“You like that, Boss?”

“I do, boy.”

The soft, wet tip of his tongue stabs my hole. It pushes inside. It explores every angle down there. 

Slap. Slap. Slap. Chad’s stroking his cock. Getting it ready to enter me.

“Don’t cum, boy!” I warn him.

“No, Boss.” Slap. Slap. Slap.

“Are you ready, boy?”

“Ready, Boss.” He puts on a condom, lubes up his sheathed cock and my hole, and puts his dick at my backdoor.

“Here I come, Boss.”

“Go for it, boy!”

Pressure builds on my hole as his battering ram seeks entrance. I try to relax, but my ring resists him. His head pops inside.


“You okay, Boss?”

“I’m good, boy. Keep going.”

“Yes, Boss.” His cock slithers inside me, breaking through my defenses. I forgot how good it feels to get fucked.

“Fuck me hard, boy!”

“Yes, Boss.” 

He backs out a bit, then rams home. His balls slap against my ass. His hands grip my loins, pulling me back on him. Precum drips from my piss slit as he hits my prostate.

“Oh yeah, fuck me, boy!”

Slap. Slap. Slap. Slap. Slap.

“Ahhh… you have a tight hole, Boss.”

“Open it up, boy!”

Slap. Slap. Slap. Slap. Slap.

“Fuck me, boy. Fuck my hole!”

Slap. Slap. Slap. Slap. Slap.

On every thrust, his cock runs over my prostate. My cock presses against its cage.

Slap. Slap. Slap. Slap. Slap.

“Ah, ah, ah, ah, ah. I’m gonna cum, Boss!”

“Empty your load in me, boy.”

Slap. Slap. Slap. Slap. Slap.

“Ah, ah, ah, ah, ah. I’m cumming!” His cock expands as he unloads his balls inside me.

“Oh, oh, oh, oh, oh.” His last thrust pushes me over the edge. My cock tells me it needs to pee, but instead, cum squirts out of my slit.






“Ahhh…” Bliss spreads over me as the tension in my balls is released in a warm, sticky, gooey mess.

“Did you cum, Boss?”

“In a way. It wasn’t a full orgasm, but it released some of my pent-up cum.”

“That’s awesome, Boss!”

“It is, boy. But we’re gonna have to wash our top sheet.”

“Ha! Ha! That’s okay. I’m happy you were able to sorta cum, Boss.”

I pull the top sheet off the bed and head to the laundry with it. I throw it in the washer and turn it on.

“What now, Boss?”

“We need to take a shower, boy.”


“I got the perfect treat for you, boy.” I head back to my bedroom and pull out a dildo and a strap-on harness. I also grab the lube.

“Oh wow!” Chad says, eyeing the dildo.

“I can’t fuck you with my cock, but I can fuck you with this.”

“Okay, Boss.”

We head to the bathroom. I slip the tag on the doorknob to alert Rod that the bathroom’s off-limits for a while.

“It’s time to get you fucked, boy.”

Chad bends over and spreads his hole for me. I can’t resist. I kneel behind him and start lapping away at his rosebud. His butt smells fantastic!

Lap! Lap! Lap! Lap! Lap!

“Oh Boss, your tongue feels great.”

My tongue explores every wrinkle in his pucker. I put pressure on it to force my way inside. 

Chad shivers with pleasure.

My tongue explores as much of his hole as it can. I grab the lube and get my index finger and his hole nice and slimy. I stick it in him.

“That feels great, Boss. Your cock will be better though.”

I slip my middle finger inside him too. Then, my ring finger. I three-finger fuck him a while.

“I’m ready for your cock, Boss.”

“Don’t you worry, boy. You’re gonna get my cock.” I put on the harness and attach the dildo. My sorry caged cock hides underneath. I wish I could really fuck Chad, but this will have to do. I lube up the dildo and put it against his pucker.

“You ready, boy?”

“Ready, Boss.”

I press against his muscle, demanding access. Suddenly, I slip in.


“I’m in, boy.”

“I figured that out, Boss.”

I let his sphincter adjust to the invasion.

“Fuck me, Boss.”

“You got it, boy.”

I gradually slide into him until the dildo’s balls rest against his ass. I wish my own cock was in him.

I pull out a bit, then thrust back in.


“You okay, boy?”

“Yeah, I’m okay. Just fuck me, Boss.”

I begin thrusting in and out of him. My cock presses hard against the bars of its cage. It resents being replaced by a silicone stick.

In and out, in and out, I fuck his hole.

“Oh, oh, oh, oh, oh. I think I’m gonna cum again, Boss.”

“Go for it, boy.” I wish I was unloading my load inside him.






His cum splats on the bathroom floor. I’m happy the dildo made him cum.

“Ahhh… That was nice, Boss. It won’t ever replace your cock though.”

“My cock’s happy to hear that, boy! Clean up your mess, and let’s hit the shower.”

Chad grabs a washcloth and wipes up his cum. We hop in the shower together. We wash each other’s hair. We wash each other’s body. We’re very thorough cleaning the other’s groin and hole. As we rinse off, we stand under the stream and kiss.

“I think you’re gonna be the small spoon tonight, boy.”

“That’d be great, Boss.”

We towel off and head back to my room.

We collapse on the bed, hugging and kissing.

When we’re ready to go to sleep, I curl my body around Chad’s. My caged cock rests in his butt crack. I drape my arm over his shoulder. We fall asleep.

--- The End ---