The Milking Den Ch. 02: Scott

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Scott hems and haws outside my door. He glances furtively down at his phone, at my door, and back at the elevator. First timers tend to do that. Heck, even repeat visitors too. Standing at your torturer’s door and sending yourself in isn’t something you ever get used to.

I watch from my peephole and grin. Scott fits his self-description perfectly. College jock, final year, wants to get his bisexual cherry popped in a no-strings arrangement before he enters adulthood. He has that awkward charm you see in every guy meeting an online hookup for the first time. From the way his eyes dart about, the way he shifts back and forth on his feet, he’s practically thinking out loud: chicken out while it’s safe or press ahead into the unknown?

“I’m here haha” [7.02pm]

Bitter resolve spreads across his face as he realizes what he’s done to himself. Feels a bit poetic, like Dante staring into the gates of hell.

I swing my door open and Scott looks up with a start.

Abandon all hope, ye who enter.

“Hey, Scott,” I chirp, slinging him a sly grin, leaning against my door frame. “Nice to meet you. Welcome to my milking den.”


“Woah. This looks like it must’ve cost a bomb.”

Scott chuckles nervously. He’s standing in the hallway and looking into my den. That’s where he’ll be spending the next hour or so – a bed with four short posts and ropes already secured to each corner. There’s also a chair rigged up with restraints at every joint, a black leather saddle, and a shelf stacked with lube bottles and toys of every kind. He’s probably wondering which of these I’ll use on him later.

“Yeah, I bought Bitcoin back before it blew up,” I joke as I stroll inside, inviting him to join me. Holding his lips together tightly, Scott steps in, watching himself as his body moves gingerly through the space.

“So… what do we do now?” Chewing on his lower lip, Scott jams his hands into his jean pockets. It looks like he’s trying not to take up too much space. His attention lingers on the ropes attached to my bed. His eyes bounce between the bed, my toys, the door.

I swish my hand in the bed’s direction before turning to my shelf to pick an oil. “Well, you strip, I tie you up, I milk you.” I’m already imagining what he looks like under his clothes, how he’d squirm as I rub him wet and glazed all over.

It takes me a moment to realize I don’t hear movement behind me.

Turning back, I catch a quick look at the guy. Scott is frozen to the spot and curled in on himself. Quickly, I realize what he’s actually saying.

Putting down the oil bottle, I step towards him carefully, like a baker reaches for a hot cookie tray. “Hey, you alright?” I ask, genuinely concerned. I’m annoyed with myself; I should’ve spotted this sooner. How did I miss this? Scott has the nervous energy of a lost puppy in need of a guiding hand; classic first-guy-sex symptom. Having lived his whole life hiding his love for boys, it must be hard to let that side of him see the light. And how sad it must be, that the first time he feels safe to do so is in the house of an internet stranger.

“This is just… a lot.” Scott chuckles nervously. I nod. It’s difficult for sure, and I can see how any lesser guy would run for the door.

But that’s not why he came. Scott’s here because he’s brave. It takes so much courage to come up to a rando’s house for to explore a new side of you; to heal the part of him that’s grown used to the cold. He’s making a choice to be himself, and I’m going to honour that journey. That’s what I do for all my boys, new and old.

I reach for his hands. Scott almost recoils, but softens. He doesn’t dare look me in my eyes.

“You’re doing great, buddy. We’ll take it nice and slow, and you can tell me whenever you feel scared. Safe word’s ‘candy’ – that means you say ‘candy’ when you need to quit for real.” I’m cradling his head right now, my thumb stroking his ear tenderly.

Slowly, and with a new firmness, Scott nods, and I know he’s ready.

“Awesome. istanbul travesti Now, take off your clothes and get on the bed.”

Scott found me through my account on Recon. He’s a college swimmer with the urge to get about with other guys, but that’s not something he can just do on campus. He stands to lose too much if people find him sneaking about other men’s rooms. He’s one of those guys who are trapped in the golden handcuffs of masculinity. Strong, supposedly straight, and nowhere else to go but down if anyone realizes otherwise.

And that’s such a shame, because Scott is such a catch. He oozes sensuality, but his hotness is tempered by soft edges. He came dressed just as I asked – a tight white tank top, short shorts and sneakers, and crowned with a head of thick tousled hair. His shoulders pop gorgeously; white cotton fabric stretches teasingly across his pecs and trunk. He must have felt so exposed – so displayed – on the way here.

But that’s all in the past. Now, his clothes are hung up on the hooks at the end of the room, and Scott is tied down to my bed. Only his hands, though; I’ve bound his wrists snugly above his head but his legs are free to move. He can tell me when he’s ready to put those on.

Also, I’m so glad Scott did me the favour of coming in his swimming trunks.

I know I say I’m not in it for just the sex, but a young swimmer in his prime… oh man. Luscious lean muscles, every fibre cleanly visible under his liquid bronze skin; hairless like a porn star to boot. And that plump bulge underneath that stretchy black fabric – does Scott even know how beautiful he is?

“When you’re on the bed, you’ll address me as Sir,” I instruct as I drizzle oil down his chest, watching it pool in the valley between his pecs and trickle down into his navel. Now that we’re in play mode, my voice is soft but commanding. “All you have to do is make sure you don’t cum unless I tell you to.”

“I’ll try.” Scott was cute from the start, but he looks so adorably vulnerable in this position. He’s so new to all of this and eager to do his best. I almost feel too bad for him to abuse him. I just want to give him a hug.

“Sir,” I remind him, giving his left nipple a pinch. Scott yelps in response. “And don’t try, boy. Do.” My dominant side rushes back into my head and into my arms. I make my first move downwards; I empty the bottle onto his bulge, soaking him all the way through until the fabric clings to his junk like a glove. He hardens as he bites his lip, afraid to make a sound.

“You like that?” I ask, and Scott nods measuredly. Trying to squeeze out a more expressive answer, I start groping him through the slick fabric as my other hand moves down to his perineum.

“Let go, Scott. You’re safe.” Softness creeps back into my voice as I coax him out of his stiffness. He lets out a dry moan as I knead him good. It’s the sound of a dusty engine roaring to life again, moving from shallow croak into a deep and full bodied moan as I press my knuckles deep into his taint. Melting into my hands, his body embraces itself again as pleasure unrolls in his loins.

“Oh my god. Oh my god.” Scott bites his lip and squeezes his eyes shut. How cute – he’s holding onto the ropes for support. But that doesn’t mean I’ll go easy. In fact, that means I’m going to get really, really mean.

I laugh as my hands slide up to explore the rest of his torso.


Scott is so wonderfully new. He responds to me like ripples on water, gasping and straining each time I move my hands.

Like other guys who’ve only been with women, Scott is used to pleasuring his partners. That’s why we’ve spent the last twenty minutes just exploring the ins and outs of his body, mapping out the parts that make his eyes water. How much does he actually know about his own body? Scott gasps as I glide across his obliques, as my thumbs trace his neck. His toes hiss and curl when I introduce his nipples to my tongue. Slowly pleasured, enjoyed like lips over ripe istanbul travestileri fruit, Scott is close to bursting at his seams.

We haven’t even removed his trunks yet.

“How’re you doing?” I ask as my fingers fan across his jawline. His face is sharp but delicate like a thin steel dagger.

Scott tries squeezing his words in between his gasps. “It’s awesome. Sir,” he adds just in time, ending with a chuckle so sheepish it almost sounds like a giggle.

I’m so glad he’s enjoying himself. He was so worried on Recon about what we’d do, whether we’d record this and upload it onto Twitter. (Anyway, the answer is no. No footage… unless they get off on it.) Now, he’s so much more relaxed than the ball of nerves he rolled in as. He sighs – and not a shallow sigh, but one deep in his lungs – as I clasp his hard cock.

“Do you wanna go further?” I ask, looking down at him carefully. He’s so new and so afraid of being used. This is his journey and it’s his call to make. His eyebrows tighten as he takes a long deep breath. I want him to say yes, of course – but he has to want it too.

He nods. But I need more.

“I need you to say it.”

Shaken from his thoughts, Scott looks up at me, not sure what I mean.

“I need you to say that this is what you want.”

Scott’s jaw tightens. My gaze is gentle, kind, but this is something I need to push him to do. If Scott is going to accept himself for who he is, he can’t just let his first bisexual experience wash over him. This has to be something that he chooses.

After a long second, Scott’s lips finally move.


“Yes what?”

It’s not about breaking the boy’s will. You have to stretch the muscle to release the tension.

“I want this.” Scott looks back on himself with his mouth agape, his eyes wide, not believing those words just came from his mouth. “I-I want you to milk me.” He looks right into my eyes – is that shame I see, clinging on like wax but melting away in new fire?

Breaking character for a bit, I lean down to him and whisper in his ear. “You’re doing so well.” And I mean it. He’s learned more about his body in the past minutes than in all the sexual encounters he’s had so far.

“Thank you, sir,” Scott mutters in response, his voice rushed but sincere. There, our brief respite ends, and we’re back in our roles as milker and boy.

I slide Scott’s trunks off. His cock springs up to life with a gasp from his parched mouth.

“You ready for this?” I ask as I stroke his ankles. Scott nods and whimpers as I fasten his ankles down to the bed. He tries testing them, seeing if they’ll yield – and he lets out a nervous laugh when he realizes he’s locked in for good. Smiling like a cat playing with its prey, I spread my hands over his pecs, fanning over his beautiful bronze skin like an explorer and a map. And then, following his treasure trail – one that trembles and shakes in response to my barely-there fingers – I move down to his desperate cock.

Scott is so well oiled that it’s almost hard to get a firm grip on him. I attack his cock with my signature move: two fists spinning in opposite directions, moving up and down his head and entire shaft. Scott’s body twists and gleams like polished marble. The oil casts his lats, triceps, nipples into sharp relief – so much better to lick and nuzzle them this way. This is pleasure tuned so sharply it’s painful. It doesn’t take much longer before he’s trembling on a knife’s edge.

“Oh fuck… oh God… I’m so close.” Scott’s pelvis is buckling against the bed, hungry for more friction against my hands. His red face is choked with hot unmet need.

Twenty minutes of being worshipped. Fifty minutes holding back his cum. Amazing show for a first timer… But I want more.

I make a show out of thinking, furrowing my brows and twitching my lips. “Hmm. Okay. I’ll let you cum.”

“Oh, thank you Sir!” Relieved, Scott eases backwards and buckles up for the ride. He’s so far gone, so drunk on pleasure, travesti istanbul that the thought of unloading makes him giggle. But I have a better plan for him.

“On one condition.” My hands grind down to a near stop and Scott swears in frustration.

“What is it?” He’s hot and bothered and totally broken. His cock twitches with a mind of its own. He’s watching me, apprehension crawling across his face. What more? Hasn’t he endured enough?

“I want you to say you love being milked by a man.”

Scott screams and throws his head back into his pillow. I keep up my slow strokes to keep the fire going as he wrestles with himself inside his mind. He keens and cries as he writhes about in his own indecision – kept on the edge of his sanity by a slow pulsing in my fist. Scott’s final barrier is not me, not that load of hot cum waiting to be shot, but the boy in his mind waiting to be let out into the light.

My hands close in on his cock. They begin a slow endless tunnel that engulfs his entire penis in a neverending stroke. Scott’s mind is ready to burst, stretched so thin with lust and wanting, until push comes to shove and he breaks that final frontier.

Scott throws his head back. “I love it! I love being milked by a man!” Scott’s eyes speak of surrender, but in that destruction is freedom. As he says it, his eyes grow brighter, his soul lighter.


One hand pumps, one hand kneads deeply at his taint, and I crash this racecar right into the finish line. Scott’s body arcs so strongly he almost lifts the bed. Shot after shot of semen burst from his tortured cock, splattering all over his body and my forearms. He roars like a dark lion tearing through the sun. I keep going, draining every drop, until he’s shaking in the aching echoes of his orgasm, his cock totally spent.

Free of his self-loathing, Scott lets out a deep laugh that rumbles across his chest. “Oh my fucking God. That was the hardest cum of my life.”

Except I’m not done yet.

I double down hard, using his own cum as lube to polish his head with a vengeance. Shocked, horrified and almost angry, Scott whiplashes against his restraints as real torture spreads across his cock head.

“You were late by two minutes. That means two minutes of punishment.”

Scott seizes up and roars. His abs clench and clench again like a panicking heart. He pulls so tightly the veins in his arms might pop, but my bonds are strong and my fingers stronger. I cup his head with my palm and rub it like it owes me money as my other hand pumps him till he sobs.

“Urgh – fuck – I’m sorry!!!”

“Take it, boy! Be strong!”

Only fifteen seconds. Are there tears in his eyes already?

Oh, does he regret letting me strap his legs down now.

Scott’s muscular thighs stop thrusting backwards as he breaks, giving in to his punishment. His suffering and the sound of slamming muscle fade out into the night.


“Thanks so much, man. This was so fucking wild.” Scott’s back in his tight tank and shorts, ready to head back out. He looks like he just sprinted a mile.

“Anytime. And I do mean anytime.” I squeeze his shoulder once more, both to comfort him and to enjoy that firm delt before he goes. I’m sad that he’s heading back to his campus closet. Hopefully, if he doesn’t find a way to come out there, he’ll always feel at home here.

“Yeah… Maybe after finals.” He blushes, embarrassed at what he just asked for, but also with guilty glee.

“Sure. Make sure you come on time.”

Scott laughs as he winces. That post-orgasm punishment still feels like it gouged out his insides.

“Well… this is it, I guess. See ya later.” Scott nods and turns around.

But stop! – something jumps inside me. I remember the way he avoided my gaze in the beginning; I don’t want him to remain that way, so afraid and ashamed, forever.


Scott looks back, his strong eyebrows slightly raised. My hands are in my pockets; I search for what I want to say.

“You’re a good man, Scott. No matter what people think of you.”

Scott pauses, blinks, and smiles. His face is tinged with regret, but his eyes aren’t completely dim yet.

“Thanks. I’ll see you next time.”

Scott disappears behind the elevator doors.

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