Previously
Josh publicly takes an Oath of Chastity, surrendering control of his sexual release to his Keyholder, Caine. The ceremony culminates with Caine physically locking Josh into a chastity cage and claiming the key, marking Josh’s submission and their bond. The final stage, the Consecration, publicly seals their pact before the brotherhood in a dramatic sexual ritual that affirms both Josh’s devotion and Caine’s authority.
Three years later we learn that Josh and Caine marry in the wedding of the year, and Caine is committed to making Josh’s wedding night a night he’ll never forget.
The Final Chapter
The wedding was so exhausting that the newlyweds simply collapsed in each other’s arms their wedding night and fell asleep. Whenever Josh was nestled in Caine’s wingspan, he passed out instantly. In this case, Caine crashed just as quickly.
The next morning, they awoke as husbands.
Caine had given a tremendous amount of thought to their wedding night, even though he knew it would be a day late. Josh had sacrificed everything for him and he wanted to convey his gratitude, devotion and love.
In the months following the Ceremony, the permanence of the chastity cage was daunting for Josh, possibly even worse than he’d imagined. It felt like he was dragging a kettlebell between his legs, had to time his bathroom breaks so as not to beg the question why he always sat while he peed, feared the outline of the cage was conspicuously visible in his workout gear and speedo, but most of all, he longed for the most basic male human function: release.
Yet, at the same time, there was a quietly growing sensation that had been captured in the language of his Oath of Chastity: “The ongoing, unfulfilled ache of Chastity”. At the ceremony they were just a set of words he didn’t fully comprehend. But more and more, he experienced actual ache for relief for which there was only one thing that could provide relief, Caine’s erect cock. And that ever present ache made him crave Caine’s relief with relentless intensity. It seemed like the pleasure of ejaculation was gradually being replaced, even exceeded, by the relief Caine provided. And the fullness of Caine’s manhood overshadowed the momentary exultation of even the best ejaculation. It was as if all his sexual nerve endings were shifting from his dick to his hole.
He’d never shared this with Caine because he didn’t know if he was imagining it and was afraid if he talked about it, it would evaporate.
Caine nurtured him through the first few months of his chastity. He couldn’t have known precisely what Josh was experiencing, but, after a while, he could tell he was gradually enjoying sex more as he grew accustomed to being caged. But by their wedding, it had been a long three years since Josh had accepted the cage, and Caine owed it to him to make it right.
The wedding was held at a Waldorf Astoria in their city, and Caine and Josh took the penthouse suite there for a long weekend. They were in the middle of a critical litigation so a real honeymoon would have to wait.
Caine had planned the day after the wedding to precision. Sunday morning Mass (complete with all the erotic undertones), a solid workout with Josh in sexy new workout gear and an afternoon by the pool, again with his-and-his speedos tiny enough to make jaws drop. He wanted their testosterone pulsing through their veins for the evening.
They had dinner at the hotel’s premiere restaurant, sharing ridiculously expensive French Bordeaux and enjoying the finest dinner money could buy. He wanted the night to be perfect.
Well into their second bottle of wine, Caine took Josh’s hand and asked, “Do you have any idea how happy you’ve made me, Little Man?”
“I have a pretty good idea,” he joked.
“Seriously, if anything even happened to you….” he trailed off.
Josh grabbed both hands and pulled him close, “Don’t worry Old Man, I’m not going anywhere”, and he pulled him in for a long kiss.
“Not if I can help it” Caine smiled. “Now let’s get upstairs, I’m going to show you exactly how happy you’ve made me.”
Caine opened the hotel suite door to maximum effect. He let Josh enter first so he could witness what had been done to the room. Lights dim, candelabras of burning candles, and flowers filled the room.
Caine stepped in behind him and removed Josh’s jacket from behind, like a butler. He carefully laid it down then stepped in front of him to untie his tie. When he began to unbutton his shirt, Josh grabbed his wrists and laughed, “Wait a minute. Isn’t this where you order me to ‘strip’”?
“I’m taking care of you tonight, Little Man,” he said and continued to seductively remove his clothes.
Before long, Josh stood in front of him, nude, his cage prominently on display. Caine knelt in front of him, cupped the cage with his hands and gently kissed it. As he stood up, he saw a look of confusion on Josh’s face. “What?” he asked.
“Sir”, Josh asked sheepishly, “aren’t you going to unlock me?”
“No, Little Man”, he smiled. “I’ve got something in mind for you I think you’ll like better,” and scooped him up and laid him on the bed, letting Josh watch him as he stripped in front of him.
Staring straight at Caine’s thickening cock, Josh whispered, “You know, there’s only one thing I want from you”.
“I know but tonight I’m going to try to give you something you’ve never experienced before”
What Josh didn’t know is that Caine had spent time with the other Keyholders talking about their Charges. He learned that, although caged, they could experience something as good as, if not better, than ejaculation—an anal, full body, orgasm. Caine went to work to learn how to get Josh there as he made it his goal to give that to Josh as a wedding gift.
Caine gently pushed Josh down flat on his back and, not unexpectedly, restrained his wrists and ankles to the bedposts. He stood up to retrieve something but stopped to admire Josh, who laid there in all his athletic splendor. “You’re so fucking beautiful”, Caine whispered. “How did I get so lucky? I could just sit here and stare at you all night long.”
Josh, nude and vulnerable, loved the attention and seductively writhed in response, wordlessly begging Caine to take him.
Caine retrieved the expensive body oil he had purchased for tonight and began to gently massage Josh starting with his feet. “But I’m not just going to just stare you” Caine whispered, “I’m going to drive out of your fucking mind…”
He started with his toes, going one-by-one, kneading, pulling, spreading, then massaging the ball of his foot, the arch, the heel, and then the top. It felt like he spent an eternity just on each foot. Then he moved up to Josh’s ankles, doing the same. Then his left calf, massaging it to putty, then the right.
He slid his fingers, warmed by the oil, to Josh’s thighs and hamstrings, paying particular attention to his inner thigh. Each stroke landed closer to his taint and balls than the one before, but always just shy. As his hands moved in that direction, Josh would try to push his hips down to meet them, but the restraints prevented him.
At long last, Caine’s fingertips grazed the bottom of Josh’s balls, which were uncaged and bloated. Josh yelped, “Oh my god”, the anticipation had been so great. Caine continued, stroking up his legs, each time just barely caressing his balls. “Oh, please Sir, please…” Josh begged. “In good time, Little Man, in good time.”
Caine hovered over Josh’s mid-section, then bent over his caged cock, and, with his hand, gently massaged his balls and taint. In a full sweat now, Josh squirmed desperately trying to push himself into Caine’s fingertips as he continued. Caine knew that Josh’s taint, which was positioned right over his prostate, was particularly sensitive, so he focused there. With his cock leaking volumes of pre-cum, he yanked helplessly at the restraints as he bucked his hips in the air, begging for more. ‘This is going exactly as planned’ Caine thought.
Caine, now nude himself, climbed up to straddle Josh at the hips to massage his face and scalp. The scalp massage, while not erotic per se, was unbelievably relaxing and when Caine moved down to his face, Josh groaned in pleasure. He was experiencing love and affection along with sexual stimulation. All the while, Caine made sure his thickening cock grazed Josh’s stomach and torso to taunt him with what was coming.
After the face massage, Caine climbed off Josh and knelt by his side, intentionally positioning himself so his hardening cock landed in Josh’s open palm. Josh gratefully squeezed it, stroked it, massaged it, but when he got too aggressive, Caine pulled away, “Slow down Little Man, you have a long night ahead of you.”
Caine bent over him and gently placed the palm of his hand back on Josh’s taint and slowly moved his middle finger into his hole. Josh groaned and whispered, “Yeah, Daddy, yeah…” and ground his hips into Caine’s finger. Caine’s finger was on a search mission, and they both knew for what. Caine intentionally avoided Josh’s p-spot at first with the intention of making Josh beg for it. He didn’t have to wait long, as Josh torqued his hips until his p-spot found Caine’s finger.
“Oooohhhhh….” Josh groaned.
“Ahhh, there it is. You’re a clever little boy” Caine responded, as he pressed directly into it.
“Oh, FUCK!” Josh cried, as he bucked his hips into the finger.
“Slow down, Little Man”, Caine reassured him. “There’s soooo much more to come…”
Josh found himself reflecting on what was happening. His sex life with Caine had been nothing short of explosive, but this was something else altogether. Caine was so attentive, so focused on Josh’s pleasure that he was at a loss for how to respond. His cage was drenched in pre-cum, so much so that he wondered if he’d cum and just didn’t know it. But the way his painfully hard cock strained at the cage answered that question. Usually he was being used, which he loved, so this was a very different experience, making the unknown of how this would end even more tantalizing.
With his middle finger, Caine began to slowly massage around Josh’s hard prostate. Josh responded so aggressively he quickly added a second finger. Concentrating exclusively on his prostate from the inside with two fingers and massaging his taint with his thumb.
“Oh…my…god….” Josh wailed. “Fuck Daddy, FUCK!” he cried.
Without stopping the action, Caine leaned over to kiss his boy and Josh almost swallowed him whole. “Please Daddy…” he gasped, not knowing exactly what he was asking for.
Caine kept that up until Josh was nearly out of his mind, then went into the next phase. He leaned over and retrieved a vibrator plug he had waiting and slid it in. “Open up Little Man, Daddy is turning up the heat”, he chided as he slid the well lubed toy up Josh’s hole.
“Fuck Sir! What is that????” Josh gasped.
“You like this, Little Man?”
“Fuck Daddy… FUCK!” was all he could get out of his mouth.
Caine took that as a ‘yes’.
Once the vibrating plug was securely in his ass, Caine climbed up to straddle his face, Bluetooth remote in his hand, grazing his balls across Josh’s face. “You want these, don’t you Little Man,” Caine asked, referring, of course, to his balls.
Josh lifted his head and tried to reach them with his tongue, but Caine pulled up and away. “Too slow little man. Here’s your punishment” and he turned on the vibrator to its lowest setting.
“Fuuuucccckkkk….” Josh moaned and gyrated his hips. “Please Daddy, please…” he begged, although he had no idea what he was asking for.
“Lay your head back down”, Caine ordered. Josh did and Caine slowly and lovingly caressed Josh’s face with his cock and balls. “There’s my boy,” Caine purred.
Josh had enough sense to simply lay back savor the moment. His prostate under assault, his cock oozing pre-cum, and his face being massaged by his lover’s warm, hard cock.
Caine let that play out, periodically increasing the intensity of the vibrator. Josh was soon beyond thrashing. He laid there, slowly gyrating his hips as if in a trance with pre-cum gushing out, dripping down his thighs. Exactly what Caine had planned, and time to move to the final phase.
As Caine climbed off Josh he programmed the vibrator to slowly reduce its speed. As the vibrator’s velocity diminished, Caine went to each corner of the bed and removed each of the restraints, each time carefully massaging Josh’s ankle or wrist.
Josh, approaching a state of euphoria, instinctively wrapped his arms around himself once he was freed. “Keep those eyes closed, Little Man”, he said as he turned to retrieve the final toy. Out of drawer he pulled a small box, inside of which was a metal barbell head ring that with a remote for it to vibrate. The ring fit snugly around Caine’s mushroom head, and was positioned so that the barbell collars, or metal balls, would press into Josh’s prostate when vibrating. Once he wrapped it around his cock-head snugly, he gave the remote a quick test. Everything was on schedule.
Caine turned back to Josh who laid there in a daze with his eyes closed and said, “I know it’s my cock you want, isn’t it Little Man?” As he said that, he climbed on top of Josh, torso-to-torso, cock-to-cock and leaned down and kissed him passionately. Josh was in such a state he nearly inhaled him. He spread his legs and crossed them around Caine’s back and pushed his cage into Caine’s warm manhood. But because he was caged, he couldn’t detect the surprise Caine had waiting for him on his cock. “Oh Daddy….” he sighed.
Josh had never experienced sex quite like this. Even with the cage, sex with Caine had been 100% fulfilling, but tonight he felt almost paralyzed with pleasure. His cock was under lock and key, but his prostate was sending shivers up and down his body.
Caine held Josh’s arms above his head and ravaged his face, mouth, ears and nipples with kisses. As he slid down his body, he adjusted the placement of his cock so it now was lodged at the entry point of Josh’s hole.
Josh knew what this meant and cried, “Yes, Daddy. YES!”
“My boy wants his Daddy’s cock, doesn’t he?” Caine taunted him.
Josh was beyond taunting. All he had the energy for was to groan…”Yesss…” he hissed.
Caine slowly push into him stretching his hole, centimeter by centimeter. Josh was nearly incapacitated, “Yes Daddy….Please Daddy…” he begged, for anything Caine would give him.
Caine took his time stroking in and out, slowly and deliberately, deeper with every stroke. Although the vibrator wasn’t turned on yet, when the barbell reached Josh’s prostate, he screamed as if he were being stabbed, “FUCK!!!!! WTF is that????” he yelped. Without knowing it, he bucked his hips into Caine to get the full effect of whatever it was that had him seeing stars.
“My boy likes that?” Caine sneered mischievously.
Now in a full sweat and barely able to speak, Josh gasped “I…I….I …”
“Well then, tell me how you like this…” and pressed the button to the lowest vibration level and felt Josh’s body immediately seize up.
For Josh, it began quietly—an odd pressure deep inside him, not unpleasant, just there, as if some long-silent nerve had woken. He almost pulled away from it, instinctively wary, but then the sensation spread. Not outward—inward. Down and up at once. A warmth unfurling low in his body, coiling through his pelvis like a held breath finally released.
It started as a pressure—deep, insistent, impossible to ignore. Not pain. Not exactly pleasure either. Just… presence. Something happening inside him that he had no language for. His first instinct was to tense, to pull away, embarrassed by how exposed he suddenly felt.
“FUCCCKKKKKK!” he whispered over and over, in slow motion bucking his hips up into Caine’s cock to get more. He was nearly speechless with passion.
As Josh slowed slightly, Caine turned up the volume, again causing Josh to stiffen. “You ok there, Little Man?” Caine asked.
The pleasure accelerated but didn’t spike the way he was used to. There was no sharp edge, no urgent point demanding attention. Instead, it rolled, slow and heavy, gathering itself in waves that seemed to move through muscle and bone alike. His abdomen tightened. His thighs trembled. Somewhere behind his ribs, something loosened.
Josh, beyond yelling now, could only answer and a barely audible voice, “Please, more Sir…”
“Here you go”, Caine said and went to the next setting. Caine held Josh as his body went into near contortions.
The pressure shifted, sharpened—not into something harsh, but into something startlingly intimate. It was as if a switch had been thrown somewhere deep in his pelvis, lighting up nerves he hadn’t known existed. His breath hitched. His stomach clenched. He felt heat bloom low in his body, spreading outward in slow, undeniable waves.
“This isn’t—” Josh thought, panicked. This isn’t what this is supposed to feel like.
But his body didn’t care what he thought.
Josh screamed like he was on fire. Caine began to pump aggressively, grazing over and over Josh’s p-spot. He could feel the barbell ring vibrating on the tip of his cock and had to concentrate not to cum. But this was for the boy. Knowing Josh was close, he turned it up to the final setting.
“Tell me if this is too much” he whispered after it went.
When the peak arrived, it surprised Josh not with intensity alone, but with depth. The sensation bloomed inside him, radiating outward in a way that felt almost as if pleasure had discovered a hidden room and filled it completely. His body responded before his thoughts could catch up.
The pressure shifted, sharpened, not into something harsh, but into something startlingly intimate. It was as if a switch had been thrown somewhere deep in his pelvis, lighting up nerves he hadn’t known existed. His breath hitched. His stomach clenched. He felt heat bloom low in his body, spreading outward in slow, undeniable waves.
The sensation grew fuller, heavier, almost overwhelming in its depth. It wasn’t focused where he expected pleasure to live. It came from somewhere internal and vulnerable, radiating through his hips, his lower back, his thighs. His muscles began to contract on their own, small involuntary movements that made him acutely aware of how little control he had in that moment.
For some reason he envisioned a volcano erupting but the molten lava was exploding inside him. He seemed to feel Caine convulsing on top of him, jerking, screaming as if he were reacting violently to the furious explosion. But how could that be, he thought to himself. What he was feeling nothing but glorious warmth flowing through his body.
That loss of control scared him.
And then—without warning—it tipped.
Finally, the pleasure surged, not in a sharp spike, but in a deep, rolling release that seemed to come from inside his core and expand outward. His body tightened and pulsed in slow, rhythmic waves, each one pulling a quiet, broken sound from his throat before he could stop it. He felt open in a way that made his chest ache, like something private had been unlocked without his permission.
For a split second, shame flared, no one should be allowed these sensations.
But the thoughts dissolved under the sheer intensity of what he was feeling. Pleasure washed through him again and again, leaving him trembling, breathless, completely undone. There was no clear edge where it ended. It faded gradually, like a tide pulling back, leaving his body humming and hypersensitive.
Caine slowly pulled out and held him in his arms, almost like the Virgin Mary held her son after the crucifixion. “Are you there, baby boy?” Caine asked, stroking his sweat soaked hair.
“Daddy…” he whispered peering into Caine’s eyes.
His heart was racing. He pressed his hand to his chest, as if to reassure himself that he was still himself—that nothing essential had changed.
What unsettled him most wasn’t the pleasure itself—it was how real it had been. How natural. How his body had responded without hesitation, without permission.
And how part of him—quiet, honest, and impossible to ignore—wanted to understand it again.
He gazed up into Caine’s eyes and responded to his earlier question, “I…I…guess so.”
The laid there for several minutes, Josh curled into Caine’s warm embrace, Caine gently stroking his boy’s face and hair.
Finally, Josh broke the silence, “Daddy, what happened?”
“I wanted to give you something you’ve never had before,” Caine smiled.
“….But what was that?” Josh asked again.
“It was intended to be an anal orgasm. I think I succeeded.”
Josh was still too exhausted to ask for details; he just laid in Caine’s arms and let himself be caressed and fondled.
When Josh was finally able to comprehend, Caine shared his feelings. “Little Man, I kissed your cage earlier and told you how brave you were. I meant that. You surrendered your manhood to me; you sacrificed nearly everything when you became my Charge. You’ve made me the happiest man in the world and I wanted to find a way to show you. I talked to the other Keyholders and did some research and found that if I could find a way to give you an anal orgasm—yes, that’s what that was—it could replace, or even exceed what you gave up for me.”
Josh sighed contentedly trying find the energy to engage. Finally, he sighed, “Sir, I gave up nothing!” First of all, I’m not keeping score, but if I were, even before tonight I’ve gotten everything and more back from you. I couldn’t be happier.”
He continued, “But tonight….damn, that was hot. Sign me up for that anytime but only do it because you’re getting as much out of it as I do.”
Then, flashing back to the volcano and feeling the warmth inside him, did Josh realize that Caine had experienced his own orgasm. He tapped Caine’s spent, sticky cock with his hand and added, “See? You had plenty of fun yourself.”
Still cradled in Caine’s arms, Josh added, “I have one request”.
“Name it”, Caine replied.
Josh scooted on his side on the bed and said, “I want to fall asleep now, in your arms, and wake up knowing I’m Mr. Caine Barrows”.
“Done!” Caine replied and slid down next to him embracing Josh with his 6’7” wingspan, leaving not a centimeter of space between the two of them.
Sinking into sleep, Josh felt the keychain Caine wore 24/7 drop from his neck onto Josh’s clavicle. Josh reached up, felt for the key that had physically and spiritually bound him to Caine three years ago, and gave it a tug.
Caine felt the tug, and smilingly asked, “What?”
“You know,” Josh replied.
Caine pulled him in even closer and exhaled with the words, “Good boy.”
-The End-
Authors Note: Meet the “Real” Josh
At the beginning of this story, I shared that it was inspired by a reader who contacted me a few years ago telling me my stories touched him deeply. We talked online and that conversation became the genesis of the story The Singlet.
He reached out again late last year and asked if, together, we could dig deeper into his past to yield another story. I agreed and we exchanged over 100 emails and those conversations became the basis for The Keyholders Club.
Much of the narrative (The Club, The Chapel, the law firm, etc.) came from my imagination as a way to drive the narrative. But the sexual themes came from him and, with his permission, what follow are quotes from those emails illustrating how much he drove the underlying ideas of the story.
For the record, and again with his permission, Josh is the character’s real-life name, and like Josh in the story, he is Asian. He’s now in his late 30s and lives in the UK, but I set the story in the US when he was much younger. Here are some of the storylines with quotes from his emails:
Dom/Sub relationship with an older Daddy
“I totally do want to have a dom/sub relationship with an older daddy type; someone who controls me but also cares for me and someone who I worship, respect, put on a pedestal. Someone I trust with blind faith simply because.”
What it felt like the first time you submitted to a man
"I think for a lot of us when we discover sub dom we feel like we are our true authentic self for the first time. In that (safe) space we can be truly ourselves without shame, guilt. We can be our true (sub or dom) self; and also express our desires, fantasies, past experiences, make sense of them in that space or heal“.
On Caine being a swimmer
“I think if I dig deep I like a tall swimmer built dom to look after me. The broad lean shoulders chest and the height. I am shorter, in real life 5 6. And probably like to see myself as that size.”
On giving your partner pleasure
“I can’t explain it but my purpose in life is to give pleasure and to please. In real life, I do also have a tendency to try to please. But I did not realise it is such my core. My true inner self. The dom’s pleasure is my sole purpose when I am in such a situation but I thrive on the validation, on the emotion, on the affection of being the sub. Of being treasured. Maybe something I did not get as much of as a youth, especially from a dad figure.”
On pain
“Pain, yes it is painful of course. But I enjoy pain when there is context. I am still working out my relationship with pain. I think pain works for me mostly when there is context.”
On Christian imagery
“ I found it arousing that he [Christ on the cross] was almost naked but that he was also suffering. I guess I do like the pain element to some extent as well. I also find it arousing that something religious could be a turn on, at least for me.”
On religious rituals
Yes, typically they are older men of authority. I came from a protestant christian background, although sometimes love to think of imagery from the catholic church in such situations. I like the formality of the language and also how it can be linked in with perve and sub/dom. I suppose I approach them with awe, worship. There is also blind faith. They would make me feel special.“
A big shout-out to Josh for his courage and candor in sharing his story. It was my honor to bring it to life for him. I hope you enjoyed reading this as much as Josh and I did creating it.
Pete
To get in touch with the author, send them an email.
