The Milking Den Ch. 08: Ken

CW: Some spanking, heartbreak

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"I just want to forget."

Ken's eyes have that hazy look from spending too much time in his memories. His hair is a black bird's nest.

I cross my fingers on my lap. I know I say milking is manly therapy, but that's not what I mean literally.

"And why does that bring you here?"

Ken's words are dusty echoes in a big room. "I'm friends with Dan. He told me he comes here when he needs to forget. You help him do that."

I shift a bit. "That's... kind of true. I help him destress by tying him up and jerking him off."

Ken's jaw catches the gentle light, framing him in soft dark swathes, a renaissance painting of grief. Late twenties, skinny lean. He's handsome in a tragic way.

I stir in my seat, not sure how to address Ken. Usually, guys came to me with a frisky urge to lay their sex drives on my altar. Not... this, whatever it was. Not a search for pleasure but a cutting off, even if temporary, of pain.

"I'm sorry, I don't think this will work out."

Ken swings his eyes up at me, bringing his focus out from twilight and down to bear on me with a smoky, wounded weight. Words pour out of him like ink, splattering like a faulty machine gun.

"Dan says that when you edge him, his mind goes blank. There's nothing except him and his cock trying to burst. He doesn't exist until he wakes up the morning after. Nothing - just black and nothing." Ken's shoulders drop, defeated, his body open. "Please. I just want one night not thinking about her."

Tilted away from the light, Ken's eyes are brimming dark pools that arrest my conscience.

Actually, what's the difference? My other boys also come here to forget. The world dissolves around them and all that's real and imminent are the straps on their wrists and the pleasure swelling in their cocks. Work, their bosses, girlfriends, parents, commitments - nothing exists but that sweet throbbing, and they're released from the shackles of responsibility for as long as they're strapped on my table. We've all been there, we've all been in need of healing.

I'm too kind for my own good. And Ken is cute in a vulnerable way.

"Fine. Tell Dan he owes me an extra milking next month."

---

When Dan told me he had a friend who wanted to get milked, I was expecting another handsome stud. Wrestler quality.

But that's not to say Ken isn't easy on the eyes too. He's slighter in figure: delicate, pliant frame. His features are softer but his soul courses under them with a dark, subtle line. His eyes brim with poetry, singing soft secrets.

"I'll go easy on you, alright?" I assure Ken as I walk him down the hall and into my play room.

"No. Go hard on me. I want you to torture me so badly I can't think."

Ken's eyes tell me he means it. I'm shocked, honestly. Five minutes before the beginning of their hell hour, my boys usually tremble with dread and anticipation. Ken, however, wanted to dive right into the mouth of the beast. What went down between him and his ex to drive him to this?

Ken's verbal riff peters off as I open the door, and his eyes land on my stations of pleasure. My milking table, the torture chair, the punishment stand.

"Are you really, really sure you're in?" I ask Ken, making sure he knows he can back out. I only play with guys who enjoy what I'm into. I don't want people to get in for the wrong reasons and end up hurting themselves in the end. And Ken - Ken is hurt bad as is.

And damaged people damage themselves.

"I want you to hurt me. Make me lose my mind, until I can't stop screaming." Ken is mad, But Ken is also getting hard.

Ken is dead set on getting wild and traumatized tonight. His eyes glow with something unexpectedly fierce. Brooding and hot, he begs me to treat him badly.

"You asked for it. Take off your shirt."

Obediently, Ken slips his ruffled head under his collar and pulls off his t-shirt. I'm impressed - he's the kind of guy who's lean but in a way you only see when he's shirtless. Slender, toned. Flat belly. He stands there, his shirt still hooped on his wrist, waiting for me to lead. I take a step towards him. He smells good in a cuddly bedhead way. He is ready to be wounded.

"You're sure you want me to treat you rough?"

Ken nods.

"You want me to abuse you, make you regret you came?"

Ken nods again, his jaw set. His commitment ignites me and now I want to see how far I can make him go. I twist one of his nipples - softly at first, a warm rub that coaxes a breath from him, and then sharpening into a strong pinch that makes Ken grunt. Ken looks at me like a guy spoiling for a fight. He tucks in his breath, bracing himself for more.

"Do your worst."

He melts away whatever worries I had. Now, I just want to make him pay for his lip. I grab him by his crotch, through his jeans, and tug his bulge hard. Ken hisses through his clenched teeth. His chest rises; his breath quickens. I hear the faintest suggestion of a moan.

"Get naked and climb on the bed."

Eagerly, Ken tugs off his belt and steps out of his jeans. He wriggles out of his baggy blue boxers, revealing his milky white ass, and spreads himself out across my bed, wrists and ankles ready to be tied down.

"I'm not sure if Dan told you the rules. You don't get to cum until I give you permission. Otherwise, you will be punished - and Dan hates it when I punish him."

I realized, at the sight of the enthusiastically receptive bound body on my bed, that he might like that.

"Trust me, you won't like it either. And before we start - in case you need to stop, in case we get too far; the safe word is 'red zone'."

Ken grunts and adjusts himself. Rarely do I encounter a subject so enthusiastic about submitting to his own destruction.

Alright, I guess we begin.

Since Ken told me he wanted to be destroyed, I start strong, not warming up like I usually do. Spreading my hands across his naked body like I'm playing a piano, I talk firmly on his nipples with one hand, alternating between the two until they turn from brown to red, while jerking him off at a healthy pace. Ken grunts as his body is stimulated and tormented. He is learning that what he wants isn't easy - but he's putting up a good fight. He's really digging himself in. And it isn't long before he's on the edge.

"Can I cum?" Ken breathes as he clenches his pelvic muscles, and I continue jerking until I feel the first hot twitches at the base of his shaft. Ken gasps, his abs convulsing. "Fuck!" He almost bursts but I smack his balls until his cum stays put. "Argh, argh, fuck!" Ken yells grittily as I land a series of firm, bracing blows on his sack.

"Is this what you want?" I ask.

Ken roars. "Fuck, yes! Do it again!" His cock and balls throb. His face scrunches up deeply.

"Oh yeah? You like it when I hurt you?" I jerk him for a heartbeat and smack his balls for another, finding a rhythm of pleasure and pain. Ken grunts, his chest heaves, his brain dislocating from this room. His lips are parted like he's trying to touch a lover. Even though I was apprehensive at the start, I felt the heat of the battle. I'm starting to get into it - I want to test the limits of how much Ken can be a slut for pain.

"Get on your knees." I unbuckle Ken and reach for my paddle. When I come back, he's kneeling on my bed obediently, his trunk misted with sweat, his sore cock and balls dangling heavily. His face is a mix of agony and indulgence.

"Hands behind your head." He assumes the position like a prisoner. His armpits are nicely trimmed and they ebb with heat and suffering. He barely twitches, even seems to welcome it when I bind his wrists with black straps. He's so eager to be put through purgatory.

"You've been a bad boy." I whisper into his ear from behind. I twist one of his nipples like I'm turning a spanner and I trace his glutes with my paddle. Shame builds inside Ken like a pressure cooker.

"Yes. I have." Ken's breath is gritty like the soot off a hot tar road.

"Why do you deserve to be punished?"

The finest quiver of emotion turns inside Ken's chest. This is why he sought me out, what he wants release from.

Ken's gaze turns heavy. I almost called this to a stop - is he alright to proceed? I rub his shoulder gently, my touch shifting from firm to soft, hoping he knows he doesn't have to push through if he doesn't want to.

"I've been very bad," Ken says matter-of-factly, his expression stoic. He wants to confront his nightmares with gritted teeth and clenching.

"And that's why you're here. You want to atone for your sins." Like a good slave, Ken accepts the red ball gag that I fit into his mouth. "That can be arranged."

My paddle cracks across his buttocks with a sharp loud smack. Ken jolts and shouts. He's coming into contact with his inner demons, given form in bondage and masochism.

"Think about what a bad boy you've been."

Normally, I torture my boys more through pleasure than pain, but Ken is really getting off on this. As I paint his white boy butt red, his entire body convulses in torment. The thoughts he's been drowning in flood his entire body, taking on physical force, and he struggles against them with each slap I deal him. He groans like a wolf in heat.

After an intense spanking, Ken's face is as red as his ass. A thin stream of drool leaks out from the side of his wet gag and forms a trail down his abs. His eyes are wet but strong.

Putting my paddle aside, I lift his chin up to look me in my eyes. "Wanna stop yet?" I ask genuinely. That was much more corporal punishment than I've dealt in a long time. But Ken shakes his head, even as his wheezes. His eyes say it all. He doesn't deserve any mercy.

"Well, in that case... I've busted your balls and spanked your ass, and you still want more. You think you're so strong, eh? A big strong man? I want to show you what a little boy you are. I think it's time for you to get fucked."

No matter what a glutton for punishment you are, any straight guy gets nervous when it's time to get fucked in the ass. As I tie him onto my torture chair, fitting my thrusting dildo right at the tip of his fuzzy hole, Ken starts to tremble. The shakes start slow. The thrashing of a prisoner against his cage.

"You like this, huh? Tied up, spanked and fucked like a little slut?" Ken braces himself and gasps as the tip of my dildo pushes up into his butt. It starts thrusting at slow speed, and then works up to a good regular ploughing. Something breaks in Ken's eyes. A deep rumble starts in his chest as his breath plunges. His straightness is tested, broken, gone. But his mind is still bleak and dark - his demons remain strong and potent. But while his mind is strong, his body sings a different song. He sweats and grunts in pure animal instinct. As the dildo plunges into his straight boy butt, stretching him wide and open, it rams against the innermost seat of male pleasure. He's melting in heat, and the heat is going to his brain.

As my dildo attacks from his rear, I attack from the front. I slap his balls tight and hard, and Ken crunches down in front, his abs pulling him inwards in shock. Spit leaks out from around his ball gag. Two rhythms beat against Ken, stretching him tight like a mad drum. Right now, Ken is surrounded by a horde of devils torturing his mind and soul. As his flesh drowns in pain and ecstasy, the walls surrounding his heart melt away. He stretches against his restraints, his abs and eyes clenching onto the final strands of his dignity. Tighter, tighter...

And then he snaps.

"Red light, red light!"

Ken chokes, heaves, and cries. Sorrow pours from his wet red eyes.

I'm stunned by how this has played out. I become awkwardly aware that I still have his hard cock in one hand and his balls in my other. The dildo's still churning him inside out but I can't hear it over his sobbing. His grief has broken through his dam, and it's all just pouring out.

"It's okay, Ken. You're alright."

***

"Do you wanna talk?"

Ken is sitting in a fluffy clean bathrobe and holding a mug of warm tea. There's a lavender essential oil diffuser on the table. He seems calmer, even though sadness still tinges his eyes. He's leaning back into me as I massage his shoulders softly.

"I broke up with my girlfriend. Ex-girlfriend, I guess." He takes a bracing breath. "She said she knew I was there, but she couldn't feel me there. She's not wrong. I just always thought she'd be there the next day."

Ken rubs the side of his mug. "Until she wasn't."

I wrap my arms around him gently and he rests his head on my sleeve. "And how do you feel about what?"

Ken trembles. "I don't know man. I was just focusing on my career and thinking about our life ahead. But she said she also needed me to think about her now."

So many men I know are like this. We are so focused on providing, being practical, and we forget to tend to the heart.

"So that's why I came here. I wanted to atone for my sins - to feel how she felt. I deserved to be punished." That was the most sincere way I've ever heard anyone say that, and not in a kinky way.

My arms bring Ken's head close to me with a soft cuddle. "You did your best, Ken. It sounds like things aren't entirely unsalvageable. I think you both might still stand a chance."

Ken lifts his head off my chest and angles backwards to look at me. "Really?" He's cautious. He doesn't want to end up hoping too hard and crashing to the ground again.

"Yeah. If you work on being more caring and in the moment, I think it'll work out. I can see you love her a lot. You're a strong man, but you don't always need to be strong, especially around her. It's not weak to enjoy what you have now."

A kind, soft warmth kindles in his eyes, spreading into a smile. It's sunshine again in his soul, and I realize now that he actually looks quite attractive when he's happy.

"Thanks man. This wasn't what I expected when I came here. I don't even know how I can repay you."

I bring him into a hug, holding him in front of me by his chest.

"Well, you could let me give you what you came here for."

Ken chuckles brightly. "Yeah. I think I'm kind of in the mood for that now."

Gently, I guide his hands to put his mug on the side table, and undo the knot holding his robe together. I open him up, spreading his creamy naked flesh in front of me, and feel my way down his chest to his hips. He sighs, his voice tingling as my fingers trail down his body to clasp tenderly around his cock.

"Usually, I tell my boys that they're here because they've been bad. But you are different. You're here because you're such a good boy, and I want to reward you."

"Oh yeah?" Ken purrs, leaning in against my body like I'm an armchair. I squirt lube over his hardening cock (I have bottles stashed all over my house) and work my way up to a slow jerk. Ken moans with released satisfaction, his voice unknotting inside his chest. I stimulate him at a good steady pace, teasing him with some good pinches and spanks just as he likes them.

"Oh, I'm close."

"Ah, ah, ah. Not yet." Now that I know he has a pain kink, I give his balls a little squeeze to hold his orgasm back. Ken grunts in enjoyment.

"I want you to enjoy your orgasm. You deserve it. But that means I have to edge you longer. Work up to a big, strong, wet load. Can you do that for me?"

"Yes sir." Ken sighs. His eyes are closed in ecstasy. "I want to be good for you sir."

"Thank you, but don't just do it for me. Do it for yourself. You deserve to feel good too."

Ken rests in my grip with trust. We are working together towards a goal, and he is wrestling with himself in that sweet aching spot just for me. I love when my boys soak in the currents of that sweet, warm pleasure, letting it flow through them without bursting. I can see the frustration in the back of his head, some thrusts getting a bit too intense, but I soothe his chest and slow my strokes down and we work together to stoke the glowing embers in his loins.

Ken and I journey through a rapturous course of highs, lows, and spending a lot of time coasting along the waves. It's so different now that he's not looking to punish himself and is opening himself up to pleasure - his body is free, relaxed, and he's letting himself be pampered. He does a fantastic job of holding it in, and he's losing himself in the warm waves of pleasure that rock inside his loins. His eyes are closed in bliss.

"You're doing such a good job. I'm so proud of you." I lick the back of his ear and fondle his nipples to the music of his strained moaning. I think he's suffered enough. He wants to be edged, and he's practically hypnotized with pleasure, but suffering is still suffering even when it's an exquisite pain.

"I'm ready to let you cum, but I want you to promise me something."

"Yes, sir." Ken is lost in a fevered haze. His cock is just five good strokes away from shooting. His nipples are sore and smoldering.

"I want you to reach out to your girl. Promise to love her well. And when you're back together, come back and we'll celebrate. Let me reward you. I will milk and hurt you good."

"Oh... yes, sir." I can hear the heat, the courage in his voice. He's come out cleansed and redeemed, with strength to slay his demons. I pick up the pace, giving him hearty full strokes and bringing him right to the point of no return.

"You can cum now. You deserve it, big boy. Enjoy."

And as his orgasm breaks through, I pepper his balls with short stinging slaps, and he lets out a deep guttural moan as he shoots a hot white sticky load all over his abs and thighs. I make sure to pump it all out, rubbing him from base to tip, wringing out every inch of pleasure from his orgasm. He writhes against me in absolute enjoyment until his thrusts die out and he sinks into warm velvet silence.

Ken sighs. "Thank you."

"Thank you, Ken. I'm glad you got what you came here for and more."

Ken is just like all my other boys. They come here to find support and release in a way that would be difficult in a society that expects them to always have it together. And, even though things started really unusually, I'm glad that I managed to help him in some way. In fact, Ken texted me just yesterday to tell me that his girlfriend and him have been back together for a month. They're going on dates regularly and spending more time together.

"I'm so glad to hear that for you, Ken!" I reply. "But remember what you promised ;)"

"Of course. I'm a good boy ;)"

"Come by next Tuesday - I need to collect my payment. Welcome to the milking den."

--

Thank you so much for all your support, it makes me so happy to know that so many of you feel seen, heard and touched by my stories. I hope that for every Ken out there, you know that you deserve to be loved.

Finally, I'm doing this all as a hobby, and it's really interacting with my readers in the form of comments, emails and tweets that make this all worthwhile for me. So please, let me know what you think! I love reading about your thoughts on my stories - what you enjoyed, what you want to see more, and what you think could use work. I can't wait to interact with you all, my boys! Until next time!