Re: The Landlord (M/M) - Chapter 6&7 - June 27th
Posted: Sat Sep 20, 2025 10:24 am
by Bound Down
Hi All. It's been a while. As a reminder/if you didn't read the bonus chapter. Dylan intentionally earned three punishments on their non-bondage date.
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Dylan woke up needing to relieve himself. Still locked in his cage, he scanned for options. His water bottle was still mostly full, but it was really all he could use. He chugged the water, hoping he wouldn’t regret that later and positioned the bottle at the bottom hole of his chastity belt, letting the piss collect in the bottle. Damn that felt good. Dylan just hoped Ben would come get him before the water he drank caught up with him.
When Ben came, Dylan was nervously squirming trying to hold his bladder. “Could you please let me out, Sir. I really need to pee.”
Ben laughed, “What a good boi, taking care to hydrate yourself.” Ben took his time grabbing the keys and fumbled with the lock more than Dylan had seen him fumble with anything. Before opening the door, Ben ordered, “When I open the door, you are going to crawl out and sniff my shoes until I say otherwise. Got it boi?”
“Siiiiiir!” Dylan whined, but Ben just held the cage door closed, not responding. “Yes, Sir.” Dylan gave in. Better to just get it over with. Dylan crawled out and lowered his head to Ben’s worn-out sneakers. The smell was bad, but Dylan’s focus was still on his need to relieve his bladder. “Sir please.” He whimpered.
As Dylan continued to sniff Ben’s left shoe, he felt his right shoe pat his cheek. “Now boi, the correct response to being allowed to smell a real man’s scent is, ‘Thank you, Sir.’ This is a privilege.”
“Thank you, Sir.” Dylan was ready to agree to anything to be allowed to pee.
“Thank you for what boi?”
“Thank you for letting me smell your manly shoes, Sir.” Dylan whimpered.
“Good boi. Now go to the restroom we’ve got fun to have today.”
“Thank you, Sir.” Dylan said over his shoulder as he rushed towards the bathroom.
When Dylan returned, Ben was holding coils of rope. Dylan stared at Ben taking him in. He wasn’t exactly less dressed than other days, but the clothing definitely revealed more of his muscles. He wore a blue soccer jersey and shorts, and under that he wore black tights and a gray long sleeve compression shirt. While Dylan couldn’t see more skin, he was definitely appreciating the lines of Ben’s muscles he was able to make out.
“Ready boi?” Ben asked, but rather than waiting for an answer he simply started manhandling Dylan into position. He tied Dylan’s wrists halfway up his back before proceeding to anchor them and his upper arms with a chest harness.
Dylan loved the feeling of the slow application of rope to his body. Ben’s strong attentive fingers carefully laying the rope exactly where he wanted. As Ben was pulling the rope across his chest tight, Dylan let out a short moan.
“Oh boi. We haven’t even started.” Ben joked, giving Dylan one his telltale smirks saying he knew exactly what he was doing and how much control he had over his boi. After finishing the chest harness, Ben pressed down on Dylan’s shoulders forcing him to kneel. “It’s been a few weeks since you’ve been locked in your chastity belt boi. How would you like your dicklet to get some attention today?”
“Yes Sir. Please Sir. I’ve been so horny.” Dylan pleaded.
Ben ruffled Dylan’s hair. “That’s how a boi should be. Horny and eager to please. But I’ll tell you what. I’m going to let you suck my dick, a privilege in itself. If you’re able to please me well enough, I’ll give your dick some attention.”
“Yes Sir.” Dylan agreed readily. Ben blindfolded Dylan before lowering his shorts and guiding his head. Dylan sniffed first. Ben definitely hadn’t showered today, but damn it was hot. He started sucking Ben’s dick, slow but steady, taking breaks to lick and suck his balls as well. Taking notes of Ben’s breathing to see what turned him on.
Ben was periodically taunting Dylan as he sucked. “What a good little bitch. Do you like the taste of a real man’s dick?”
Dylan moaned in response to Ben’s jibes but kept his mouth busy not wanting to lose progress.
“Maybe I shouldn’t unlock you. You’re such a good horny boi and bois like you don’t make enough seed to spare.”
Dylan whined as he continued to suck. As he felt Ben’s dick surge more frequently, Dylan felt Ben’s hands pull the back of his head forcing him on Ben’s dick until it was in the back of his throat. Ben grinded his hips until he came. “Swallow it boi.” Was Ben’s only command in between his post orgasm gasps.
Dylan dutifully obliged but wished he could get some water. The taste lingered heavily in his mouth for several minutes.
When Ben finally released Dylan’s head, he pulled up his shorts, took off the blindfold and ordered him face up onto the bondage table.
Dylan eagerly laid his bound form onto the bondage table, using his free legs to wriggle him into place. Ben used more rope to tie his ankles shoulder width apart to the sides of the table. Then he attached the rope over the shoulders of Dylan’s chest harness to the top of the table, preventing him from sitting up.
“Do you think your dick earned some attention, boi?” Ben asked, dangling the keys to the chastity belt in front of Dylan.
Dylan paused trying to think what the right answer was. If he said yes, would Ben use that as a chance to punish him say his dick never deserved attention? If he said no, would Ben simply agree with him and move on? When in doubt, joke your way out. “I don’t know Sir. I think the taste of cum lingering in my mouth says I pleased you well enough.”
Ben pinched Dylan’s right nipple hard enough to make him grunt. “I’ll have to work on a special gag for you if you think the taste of my cum in your mouth is all it takes to please me. Maybe sucking on my cum rag all day while I ignore you will teach you the difference.”
Dylan grinded his hips in the air in response. Ben had such a calm command and easy response to every sarcastic quip Dylan could think of. Ben was in charge, not just in action but even in their conversations.
“You’re lucky there is nothing you are grinding against, or I’d have to punish you.”
“Sorry Sir. You’re just so hot.” Dylan added the second part without thinking. That wasn’t saying much, was it? Ben was obviously hot, but Dylan wasn’t sure he’d said it outright before.
Ben let go of Dylan’s nipple. “Flattery won’t be an excuse if you actually break the rule. Bois have such little self-control. It’s why you need to be locked in chastity and why you need constant reminders of who’s in charge.”
Dylan could hear Ben’s typical commanding voice come through but looking at his face he saw his earnest smile. “Yes Sir. Thank you for keeping me in my place. I appreciate it.” Dylan said submissively, before quipping, “Even if you putting me in my place was exactly what made me forget my place to begin with.”
Ben pinched Dylan’s right nipple again, this time harder. “That tongue of yours is going to get you in a lot of trouble, boi.”
“Maybe you should do something about it, Sir. I wouldn’t want to ruin your plans for the day by making you punish me for something.” Dylan taunted.
Ben didn’t take the bait, “Don’t worry about me, boi. My plans are to play with my new bitch. Whether I please or punish him doesn’t make a difference.”
Dylan blushed at being called Ben’s Bitch. Not just a bitch, or a boi, but Ben’s.
Taking advantage of Dylan’s momentary silence, Ben continued, “It has been a couple weeks, so I think I’m going to give your dick some attention after all, whether you’ve earned it or not. Assuming you still want me to?”
“Yes Sir. Please Sir.” Dylan practically begged.
Ben unlocked and removed the chastity belt, lifting Dylan’s waist surprisingly easily to slide the belt from under him.
Dylan’s dick got hard the moment it was pulled from its metal prison. Ben went to dig through Dylan’s drawers. “Have you cum from electro before, boi?”
“Yes Sir.” Dylan said, a little sad it wouldn’t be Ben’s strong hands jerking him off. Oh well. At this point he really just wanted to cum and would take it any way it happened.
Ben secured one silicone loop around the base of Dylan’s dick and balls and a second half way up his dick. Then he placed two pads along the lines where his crotch met his legs. He turned the pads up first until Dylan was moaning in pleasure. Next Ben turned up loops around Dylan’s dick and balls.
Dylan moaned louder feeling himself build already, something that generally took longer using electro. Ben kept raising the intensity of the dick loops until it hurt. Dylan grunted in pained surprise. “Too far Sir.”
“Shhhhh boi. If you’re talking, you’re not focusing on cumming. If you’re not focusing, I’ll need to increase the intensity to make up for it.” Ben raised the intensity on the dick loops to make his point
Dylan looked into Ben’s smiling face as he whimpered in distress. The mischievous smile told him what he should have known all along, this was not going to be an easy orgasm. His dick hurt past the point of pleasure.
Dylan writhed in his bonds but found no escape. It didn’t take long for the intensity or his leg muscles spasming for him to build up a sweat. He tried to focus on building an orgasm, but anytime he felt he was making any kind of progress, Ben increased intensity in the cock loops.
“Come on boi. I don’t have all day. You said you were horny. You said you could cum from electro. Do you need this thing at max intensity to get off?” Ben complained with mock impatience.
“Please no Sir.” Dylan begged. He felt the electro intensity increase in response to him speaking. Apparently, he wasn’t even allowed to respond.
Dylan moaned as his dick went soft losing any progress he had made. As he grew accustomed to the new intensity, Dylan tried again to just get over the edge so the torment would end. He clenched his muscles trying to build from the stimulation and closed his eyes in focus. Despite the electro still being more uncomfortable rather than pleasurable, Dylan still felt he was able to start building towards orgasm. Although the second he felt achieving one would be possible and not some far off edging goal, the intensity increased jolting his focus. “Fuck” Dylan shouted in frustration.
Ben merely smiled and increased the electro further. Dylan endured round after round thinking if he could just cum the torment would end. He tried faking Ben out by appearing to be further from orgasm than he really was, but nothing worked, and every round ended with his dick in pain and his sex drive frustrated.
Finally, Ben turned off the electro. “Well I think that covers one of the three punishments you earned last night.”
“What?” Dylan whined.
“Did you forget the three punishments you earned already?” Ben smiled cruelly. “I figured we could knock out two birds with one stone today. First, cover the punishments you earned. Second, give you your first reminder that your pleasure comes from your hole, not your pathetic dicklet. Maybe for your birthday or something, you can orgasm. But before you can orgasm again, you need to learn that attention to your dick is much more likely to be painful, so you learn to focus your pleasure from your hole, nipples, and most importantly pleasing me.”
“Yes Sir.” Dylan whimpered at the thought of two more rounds of punishment, though his dick was getting hard again at the same time.
Dylan remained silent as Ben removed the electro rings and pads. Ben returned with a leather blindfold. “I think the punishment will work better if you can’t see it coming. Also, your pathetic puppy dog eyes almost had me and I can’t be going soft on your punishments, or you’ll never take me seriously.”
Dylan was encased in darkness waiting for whatever was to punish him beyond his already painful edging. Dylan heard the strike of a match and before he had time to put it together, he felt a fiery pain in his balls. Then two more spots on his dick burned. Ben was dripping hot wax on his groin. Dylan liked hot wax but hadn’t used it on such sensitive locations before. Rather, his nipples stomach or back. On his dick and balls, the wax felt so much hotter even if it only lasted for a second.
After a particularly long round dripping up and down his shaft with precision, Dylan begged, “Please Sir. I’m sorry Sir. I’ll be good.”
“Shhhh. I know you will, boi. Because next time you think of disobeying me, you’ll remember this.” Ben took on his cheering teammate persona again as he encouraged Dylan, “You can do it. Just sit with the pain.”
Eventually Dylan’s entire groin was covered in wax. Ben blew out the candle before setting it down, then began unceremoniously rubbing off all the wax. When Dylan winced from the tugging on his pubic hair Ben merely commented, “Maybe we should unlock you more often. A boi really shouldn’t have this much hair down there. It gives the wrong ideas about his manhood.” Ben emphasized his statement with a moderate tap to the balls, eliciting a whine from Dylan. Once Ben had rubbed off most of the wax, he grabbed the candle again.
Dylan begged, “Please Sir. Isn’t one round enough?”
“One round might be plenty for a normal day. But I think a second round will really make the lesson stick. How’s all this attention to your dicklet, boi?”
“It hurts, Sir.”
“I bet your chastity would be a welcome relief from all this attention, huh.”
“Yes, Sir. Please lock me back in chastity and forget about my dick.”
“Can’t do that yet. You’ve got at least one and a half lessons left. But are you going to be asking for more attention to your dicklet anytime soon, boi?”
“No Sir. I’ll be good and focus on your dick. It’s the only one that matters.”
“Good boi. Someone’s learning.” Ben began dripping more wax across Dylan’s body, making sure to give extra attention to covering the groin a second time.
Dylan winced and tensed at the unpredictability of the drops. When the next drops would fall, where, how much. The stress and tension was almost worse than the pain. A few drops fell on his glans and Dylan screamed. The pain was much worse than the tension. Dylan’s arousal was the only thing making this bearable, but even that was strained.
Dylan heard Ben blow out and set down the candle a second time, once again scraping off the wax around his groin. Dylan was too nervous to ask if there would be a third round, so he just waited in silence. He sighed in relief when he heard Ben grabbing the candle and put it away.
Ben grabbed something else, and Dylan felt mist across his groin then Ben wiping it up. “How does that feel, boi?”
“Uhhh fine, Sir.” Responded a little confused.
“Good. That was saltwater. Wanted to make sure your dicklet was still going to be in good condition for the next round.”
Dylan groaned but heard no response from Ben. Instead he heard Ben pulling things out of presumably his gym bag. He heard a bottle open and then felt Ben caressing his dick and balls. Dylan groaned with pleasure this time as Ben slowly jerked his dick. Ben must have put on surgical gloves or something as Dylan could tell that wasn’t the feeling of skin to skin contact. Then his dick started to feel warm.
“How’s that feel, boi?”
“Uh good, Sir. I think. What is that?”
“I mixed some lube with peppers to make it hot. This is one of the lighter bottles. It’s not too hot then?”
“No Sir. It feels nice.”
“Well, we’ll need to fix that.” Ben quipped, pulling out another bottle. Ben started jerking Dylan off again. It felt nice and warm while he was jerking, but once he stopped the heat felt more intense, uncomfortable. “How’s that boi?”
“It’s definitely more intense, Sir.”
“Would you like to cum from me jerking you off with this? Fair warning, after you cum, the heat will still be there.”
“Yes, Sir. Please make me cum.” Dylan knew the heat would be painful after cumming, but he didn’t know the next time he’d get a chance with how Ben’s been talking. And at least it would be pleasant up through the orgasm.
Dylan felt a harsh tap on his balls, “Wrong answer. And I thought you were learning.” Ben’s amusement was plain in his voice. He pulled out another bottle and began jerking again. This time the heat was uncomfortable while he was stroking, not so bad that Dylan didn’t build to orgasm all the same. But when Ben stopped and all Dylan had to focus on was the heat, he started squirming.
“I think we’re getting closer, boi.” Ben remarked as he pulled out another bottle.
“Please no Sir. This one’s enough.”
Ben somehow managed to pat Dylan’s balls condescendingly, “Silly boi. We don’t stop at enough for punishments. That’s for when you’ve been good and even then, it’s fun to take you to too much sometimes.” Ben began stroking as Dylan whimpered. The heat was so intense. While it didn’t make his dick shrivel and take him entirely out of his horny mindset, the heat definitely removed any thoughts of orgasm from his mind.
Dylan squirmed. He wanted to whine but knew this was lose-lose. Either Ben kept jerking and the time in pain continued, or he stopped, and the pain gets worse until it finally fades. That’s assuming Ben didn’t start again.
“How’s that feel, boi.”
“It hurts, Sir!” Dylan moaned.
“Not bad enough for you to go soft though it seems.” Ben said.
“Barely, Sir.”
Ben stopped stroking and without the distraction of pleasure the heat became overwhelming. Dylan panted through the pain as his dick went flaccid in record time.
“I guess you’re right, boi. I think we found the right level for now.”
“Amazing. Sir.” Dylan whined sarcastically through the pain.
“I’ll give you a choice now. It’s a trap, but the trap is obvious in the choice. I can either torment you more with this lube and not let you cum today, or you can wait for this lube to wear off, I’ll give you an orgasm however you want it but afterwards I’ll immediately apply the next lube spicier than this one and line your chastity cage with it so you’ll be feeling the heat for a while.”
“I don’t think I could handle that, Sir. Not after cumming.”
“Then beg me to torture you with this lube, boi. Tell me how you don’t want to cum. Tell me how you want your dicklet to only feel pain today as a reminder that it is not an organ for pleasure. Beg me to lock you back in chastity after this to protect your sad pathetic dicklet from the attention it deserves.”
Even through the intense heat and lack of stimulation, Dylan’s dick went rock hard hearing Ben’s command. “Yes Sir. Please torture me.”
“That’s not enough boi. I want to hear it all back. In your own words.”
“Sir. Please torture my dicklet with your lube. Please teach me that the only attention my dicklet will get is pain and that the chastity cage is a gift from you to protect my dick from the attention it deserves. Please show me that only your dick matters. Please Sir. Torture my dick and when you think I’ve learned my lesson, lock me back in chastity.”
“Good boi.” Ben praised, clearly satisfied, as he started stroking again. The renewed spicy lube felt like it was burning Dylan’s sensitive dick, but the only complaints that left his lips were the occasional whimpers. “How long do you want to stay in your chastity belt boi?”
“Until you decide otherwise, Sir. I want to please you.”
“Then answer the question that was asked. How long do you want to be locked in Chastity?”
Dylan wracked his brain for the right answer. He figured a week would make Ben punish him worse, but obviously a year would be overkill. Hopefully a year would be overkill. “Sir, we’ve only known each other for about a month. While I may deserve and want to stay in chastity longer when the time comes, I think after another month would be the right time to check in.”
“I don’t know that this lube is spicy enough, if you’re able to give that clear of an answer.” Ben quipped with mock annoyance, “I was hoping through the pain you’d say something dumb like 10 years.”
“Sorry Sir. I don’t think I could commit to 10 years with someone I’ve known for a month.”
Ben slapped Dylan’s balls and continued stroking. “I wasn’t going to hold you to 10 years, boi. I was just hoping you’d be desperate enough to offer it.” After a pause, Ben offered, “Let’s do this. We check in in a month, but if you give me 10 orgasms before that, maybe you get let out early, maybe you get a different reward. If you don’t give me 10 orgasms by the time we check in, we’ll need to give you another lesson like this one on how to be a better hole.”
Ben’s offer didn’t sound like there was much option for refusal, so Dylan merely acknowledged, “Yes, Sir.” Giving 10 orgasms would be difficult if they continued to only meet a day or two a week, maybe they’d start seeing each other more.
“Good boi. Now remember, it’s the responsibility of a good boi to get his Sir in the mood, not just to please him when he is. If I don’t feel like cumming for the next month, that’s still on you.”
“Yes Sir.” Dylan acknowledged. At this point, Dylan was wriggling more in his bonds covered in a layer of sweat. As the stroking drew on, he became more aware of the pain and less aware of the stimulation of the stroking. He wanted it to end but figured any complaint would only encourage Ben to go longer. A while longer, despite the stroking, Dylan’s dick started to go flaccid again as the pain overshadowed the pleasure. At that point, Ben gave a few last good tugs and let go.
“Good job boi. I’ll leave you alone to think about what you’ve learned today. When I come back we’ll get you locked back in your chastity cage.”
“Thank you, Sir.” Dylan said as he heard Ben walk out of the room and the lock click behind him. Like before the heat seemed to build after the stimulation died down. Dylan panted through the intensity and tried pinching himself to distract himself from the sensation. Other than the occasional flexing to focus on something else, Dylan didn’t struggle anymore. He was drained from the long session and weariness was starting to creep in.
Once the pain finally faded, Dylan heard Ben return. He felt a cold damp cloth tenderly clean off his pubic area. He then felt Ben untie his legs from the table and lift his hips to place the chastity belt under them. Dylan was a ragdoll at this point, but Ben seemed to handle him easily. Once the cage was locked back on, Ben untied the rope connecting the chest harness to the table and picked Dylan up in his arms carrying him to the bedroom.
Ben placed Dylan gently on the sheets and laid on the bed behind him, holding him firmly. “You were very strong today. You went through a lot. How are you feeling?”
“Tired Sir.” Dylan offered.
“Did anything go too far?”
“Maybe too intense for regular play, but not too far for a punishment I basically asked for.”
“Are you sure? I’m sure I could find less intense punishments that you would also want to avoid.”
Dylan wiggled into Ben. “I’m sure Sir. It may be a while before I try to earn a punishment again, but I like the idea that there’s unpleasant consequences behind disobeying you intentionally, and this wasn’t too far for that.”
“You’ll let me know if that changes, right boi?” Ben asked commandingly.
“Yes Sir.” Dylan wiggled in again and they both fell asleep, Ben still holding onto Dylan.