Chapter 8: Breaking the Boy In
Robert led Eddie into the study, his robe hanging open, Eddie naked and clutching his discarded clothes. Their mutual arousal was blatant, twin erections standing thick and eager between them, a silent testament to the unspoken energy thrumming in the room. The heavy mahogany desk, the leather armchairs, the rows of books—all of it felt like a sanctum now, a place for a different kind of instruction.
“I have the exercise clothes ready,” Robert said, his voice a low rumble. He gestured to two neat piles on one of the armchairs. “Not the green today. A rich blue.”
Eddie glanced at the items: a thin thong, tight stretchy cotton shorts, and an oversized vest for each of them. His own hard cock twitched, and he saw Robert’s do the same. The fabric looked impossibly thin. “Should we…?” Eddie asked tentatively, his eyes flicking from the clothes to Robert’s formidable arousal.
Robert smiled, a knowing curl of his lips. “There is a term,” he began, moving closer, the space between them charged. “That I sometimes hear, but not many speak of it. It’s called ‘skimming the cream.’ Do you know it?”
Eddie frowned, thinking. “I know what it means when it comes to actual milk.”
“Well, it’s similar,” Robert said, the grin returning. “It’s possible to ejaculate just a little, just to take the edge off, but not fully unload, if that makes sense.”
The concept intrigued Eddie, a puzzle for his body to solve. “How?”
“Instead of telling you,” Robert murmured, turning to the side table and pulling open the drawer to reveal a familiar bottle of clear lubricant, “why don’t I show you?”
He beckoned Eddie over to the space between the two armchairs, before the cold, unlit fireplace. The grandfather clock’s steady tick was the only sound apart from their breathing. Robert poured a generous amount of slick, cool lube into his palm, then reached for Eddie first. His large, soft hand closed around Eddie’s shaft, stroking slowly, coating him. Eddie gasped, his head falling back. Then Robert lubed his own, even thicker cock, the sight making Eddie’s mouth water.
“Come here,” Robert instructed, and Eddie stepped close, their bodies almost touching. Robert took both their cocks in his hands, wrapping his fingers around them, pressing them together. They were a hot, slippery column of flesh in his grip. “Now kiss me.”
Eddie didn’t hesitate. He leaned in, capturing Robert’s lips, the kiss deep and searching. As their tongues met, Robert began a slow, rhythmic stroking motion, his hands working in unison. The pressure was incredible—the friction of his own cock sliding against Robert’s, the heat, the firm grip.
“Feel it,” Robert breathed against his mouth, breaking the kiss for a moment. “Don’t chase it. Let it build slowly. It’s like edging, but you let the wave crest just a little. Just let a little spill over.”
Eddie nodded, lost in the sensation. He focused on the tight, coiling pleasure low in his belly. Robert’s hands were masters, adjusting speed and pressure, milking them both towards a precipice. The kiss resumed, wet and open-mouthed, a messy tangle of need. Eddie could feel his balls tightening, the familiar urgent pressure building, but Robert’s rhythm was a promise, not a demand.
After a few minutes of this, both men were shuddering. Eddie’s thighs trembled. Robert’s breath grew ragged. They were on the very edge.
“There,” Robert growled, his voice thick. “Just let it… happen.”
He slowed the movements, his strokes becoming tender, almost teasing. The peak shifted. It wasn’t a violent eruption, but a gentle, inevitable overflow. Eddie felt a warm, pulsing release, not the full, convulsive burst he was used to, but a soft, continuous seep of pleasure. He heard Robert grunt, felt the older man’s cock jump in his hand, and saw streaks of white mingle with his own across their joined flesh. Robert kept stroking, gently now, mixing their spend, painting their slick, heated skin with it.
The relief was profound, a sweet diminishment of tension that left his body humming, not drained.
Robert rested his forehead against Eddie’s, both of them panting. “How was that?” he asked, his own voice slightly dazed.
Eddie smiled, a lazy, sated thing. “Fucking perfect.”
“Don’t clean up,” Robert said, pulling back to look at the glistening mess on their cocks and his hands. A dark, possessive gleam was in his eye. “I want to taste that mixed with your sweat later.”
Eddie chuckled, the sound shaky. “Sounds hot as fuck.”
“Let’s get to exercising then,” Robert said, his tone shifting to brisk practicality. They dressed in the blue garments. The thong felt obscene, a mere scrap of fabric cupping his softened, spend-slicked cock and balls. The shorts were tighter than yesterday’s, leaving nothing to the imagination, and the vest gaped at the neck, exposing his hairy chest. Robert looked similarly, powerfully on display.
The first half of the routine was a familiar echo of Sunday. Deep squats, lunges, stretches that pulled at every muscle. Robert was just as tactile, his hands always finding Eddie’s body—guiding his hip lower in a lunge, pressing firmly on his back during a hamstring stretch, kneeling behind him during a butterfly stretch, Robert’s own powerful thighs bracketing Eddie’s, his front pressed to Eddie’s back. Each touch was a brand, a reminder of what they’d just done and what simmered beneath the surface.
After a particularly deep series of plié squats, Robert called for a rest. They were both gleaming with a fine sheen of sweat. Eddie’s cock, stirred by the constant contact and the memory of Robert’s hands, was half-hard again, tenting the tight blue shorts.
“Take them off,” Robert said, nodding at the shorts.
Eddie did so eagerly, pushing the shorts down his legs and stepping out of them. He stood before Robert in just the blue thong and the vest, his renewed erection obvious. He was willing, eager for whatever came next.
Without a word, Robert stepped forward, his hands sliding under Eddie’s thighs. He lifted him as if he weighed nothing. Instinctively, Eddie wrapped his legs around Robert’s thick waist, his arms circling Robert’s neck. Their faces were inches apart.
Then Robert kissed him. It was not like the frantic, shared-peak kiss from before. This was slower, deeper, a claiming exploration. Eddie melted into it, his body supported entirely by Robert’s strength. He could feel the hard line of Robert’s cock, still damp from their earlier release, pressing against his own through the thin layers of fabric.
Robert’s large hands gripped the swell of Eddie’s ass, kneading the firm flesh. Then they began to move. He stroked the full curves, his thumbs tracing the lower crease where cheek met thigh. Then, slowly, one hand drifted inward, into the cleft.
Eddie gasped into the kiss. Robert’s finger ran along the seam of his body, a slow, deliberate caress over the thong’s fabric. The pressure was exquisite, teasing. Robert’s other hand held him secure, a fortress of muscle.
The finger found its goal. Through the damp blue fabric, Robert rubbed slow, firm circles over Eddie’s hole. There was no attempt to penetrate, just the relentless, gentle pressure of the pad of his finger against that most intimate nerve.
A deep, shuddering moan was torn from Eddie’s throat. He broke the kiss, panting, his forehead falling against Robert’s shoulder. His own cock, trapped between their bodies, leaked precum in a steady, helpless trickle. He thrust against Robert’s stomach, seeking friction, lost in the dual sensations—the secure, dominant hold and the exquisite teasing at his entrance.
“Robert,” he choked out, a plea and a prayer.
Robert’s breath was hot against his ear. “You like that, don’t you? Feeling this clean, tight little hole being touched.”
Eddie could only nod, his body arching, pushing back against that magical pressure. He was utterly exposed, utterly pliant. Robert was teaching him a new kind of readiness, a new depth of surrender, and Eddie was learning fast, his whole being focused on the promise in that circling finger. The world narrowed to the strength holding him aloft and the relentless, gentle promise of what was to come.
Robert's finger pressed a final, firm circle, and then the contact was gone. He lowered Eddie with a controlled, gentle grace, setting him down on the thick rug. Eddie’s legs wobbled, the muscles liquid. Robert steadied him, a large hand on his bicep.
"Apologies if I sprung that on you, son," Robert said, his voice a low hum in the quiet room. "I got pulled into an instinctual flow and–"
"Please don't apologise," Eddie interrupted, panting slightly. A slow, dazed smile spread across his face. "That was another grade A experience. A plus, in fact."
Their eyes met. Robert’s gaze, usually so knowing, held a flicker of something searching. The silence between them was dense, filled with the scent of their shared sweat and the drying, salty musk of their earlier release. It was more intimate than the physical act itself.
"So," Robert finally said, clearing his throat slightly. "You're comfortable with the direction this is going?"
A short, breathy laugh escaped Eddie. He looked down at the prominent bulge in Robert’s blue shorts, then back up at his face. "That you’re going to squeeze that massive hog into my tight hole? I wouldn't say comfortable." He grew serious, the smile fading into something more earnest. "But yes. I want that. I want that with you, because I know you won’t push me too far or hurt me."
"Never," Robert said, the word absolute. He pulled Eddie into his arms, a rough, encompassing hug. Eddie sank into the solid warmth, his cheek against Robert’s hairy chest. "Although I am not saying it won't be intense and uncomfortable at times. But that is a bump in the road to the palace of pleasure, shall we say."
"Fancy," Eddie mumbled into his skin, his voice muffled. He pulled back, grinning. "I'm up for a road trip to that palace for sure."
Both men chuckled, the tension dissolving into something lighter. Robert gave him a firm pat on the back."Right. Enough dawdling. It's time to get back to exercises."
The second part of the regime was a revelation. Kettlebell swings, planks, resistance band work—it all flowed with a new rhythm. Eddie found his focus had shifted. It barely felt like exercise. The burn in his muscles was secondary to the pleasure of proximity. Watching the powerful shift of Robert’s shoulders, the flex of his thick thighs under the blue fabric, the concentration on his face. Being close to Robert, catching his approving nod after a perfect set, was its own reward.
At the end of the final set of kettlebell swings, Robert took the weight from Eddie’s trembling hand. Both men were sheened in a fresh layer of sweat, their vests clinging. Robert’s eyes crinkled with a genuine warmth.
"You did brilliantly. Consistent form. Excellent stamina." He placed the kettlebell aside. "Which means you now get a treat."
"Please say it’s your throat," Eddie blurted, the words out before he could think or stop himself.
Robert’s eyebrows rose, then a slow, delighted beam transformed his face. "Well, I was going to suggest that as an option," he said, his tone playfully formal. "And it is the thing I would like to do most of all. But if you want to hear other possibilities–"
"No," Eddie interrupted again, shaking his head, a helpless laugh bubbling up."Sorry. But not only do I want to experience that again, I want to learn how to do it. I've been… obsessed with the toys you gave me. Thank you for that, by the way." His gaze, bold and wanting, dropped pointedly to Robert’s crotch. "And I've been very eager to try the real thing again."
Robert beamed, a look of pure, unadulterated satisfaction. "Then we have ourselves a plan. But first," he said, gesturing to the armchairs, "can we talk about next steps? Or do you need to get on with the treat first?"
Eddie wiped his forehead with the back of his arm. "I still have a little brain power to spare."
They sank into the familiar leather armchairs, the cool material a shock against their heated skin. Bottles of cold water waited on the side table, condensation beading on the plastic. They drank deeply, the quiet domesticity of the moment a strange counterpoint to everything else.
Robert spoke first, his tone shifting to that of a thoughtful mentor. "You've definitely earned the right to go further with Mary-Jane. She’s keen, I know that. Given your progress, I could step back. Let you get on with it."
Eddie listened, his heart thumping a strange, dual rhythm. The thought of Mary-Jane was a distant flare, one he knew he should feel more strongly about.
"But," Robert continued, watching him carefully, "I'd like to keep things slow. If you're in agreement."
"I want all of this to last as long as possible," Eddie said, the honesty flowing easily. "I’m in no rush. Not with the education and… relief… you're giving me."
Robert nodded, a subtle relaxation in his shoulders. "Good. I’m pleased you agree." He took another sip of water. "I feel some over-the-sweater breast action is the next logical step with her. Just feeling the shape, the weight. Acclimatizing. Putting your incredible talent with nipple play to work."
Eddie nodded. "That sounds… manageable. Thanks, Robert."
"Next," Robert said, and his voice took on that administrator’s focus, the one that both thrilled and unnerved Eddie. "Moving on from oral pleasure." He saw Eddie’s alarmed look and held up a hand. "Or, should I say, adding to oral pleasure. As I would very much like that to continue."
He leaned forward, his elbows on his knees, his expression intent. "I would like to add anal play to our expected schedule."
The words hung in the air. They weren’t a surprise, not after what had just happened in Robert's arms. But hearing it stated so plainly, as a scheduled item, sent a jolt straight to Eddie’s groin. His cock, which had softened during their talk, began to thicken again against the damp blue thong.
"You understand the importance of cleanliness. A point of pride for you as you have already told me. But we would need to instate a more thorough regimen when we are due time together."
"Just tell me what I need to do," Eddie said, wanting to do his part properly.
He was earnest in his reply, his voice stripped of its usual playful lilt. This wasn’t a sex game anymore; it was an apprenticeship in a vital craft.
Robert rose and went to a low cupboard near his bookcase. He retrieved a blue bulb syringe, sealed in its plastic packaging, and a small bottle of glycerine water-based lubricant. He placed them carefully on the desk. "Here is your own," he said. "To use at home. Or, obviously, you can use one here if time or circumstance don't allow."
"Okay."
"Lukewarm water," Robert began, his tone that of a trusted foreman. "Not hot, never cold. Don’t overfill yourself. Your goal is to clean only the rectum, no deeper. You are washing a passage, not an organ. Always use lube on the tip." He tapped the bottle. "Gentleness is everything. If the water isn’t clear by the fifth flush, it isn't the day for it. No amount of rationalizing will change it. You pack up your desires and you try again another time. It keeps everyone safe, respectful."
Eddie absorbed this, nodding slowly. The logic was clinical, simple, and utterly sensible.
"Now, the why," Robert said, leaning back against the desk, his powerful arms crossed over his chest. "The deeper purpose, in the context of your lessons. To know what it is like to be penetrated—to truly feel it, in your gut, your mind, your spirit—makes a person a much, much better penetrator. Whether with fingers," he held up his thick, blunt digits, "the tongue, a toy, or the cock itself. The knowledge of how to please someone’s receptacle—a vagina or an anus—it comes only in truth from having it done to your own person. It creates empathy. It turns a selfish act into a shared destination."
He paused, letting the words settle in the quiet room. The clock ticked. "This all make sense to you?"
"Yes," Eddie said, without hesitation.
"And then there is the prostate. An organ that can initiate it's own orgasm, separate from the penile orgasms you are familiar with, or sometimes in tandem. This will unmake you in the best possible way, but can sometimes take time to truly activate and appreciate. But it truly has to be experienced to be understood. So, to be clear, you are happy to move forward with this aspect? You understand we are moving beyond mouth and hands?"
"I want to," Eddie said, and the force of his own conviction surprised him. It wasn’t just lust. It was a sudden, profound curiosity about a world where Robert was his guide. "I trust you. I’m placing my confidence in you."
Robert looked at him for a long moment. His stern features softened, his eyes shining with a light Eddie hadn't seen before. "Thank you," he said, and the words were low, stripped of any artifice, completely heartfelt.
He cleared his throat, the emotion receding behind a warm smile."Right. It is time for your treat."
He retrieved the now-familiar blanket from under the armchair. He placed it, folded into a thick pad, at Eddie’s bare feet. Robert lowered himself onto it, kneeling before Eddie.
And for a full minute, he just looked. His eyes travelled up the muscled calves dusted with dark hair, the powerful thighs, the swelling hardness under blue cotton, the flat stomach, the broad chest. His hands followed his gaze, but slowly, so slowly.
He didn’t pull at Eddie’s clothes. He touched the exposed skin. His calloused fingertips traced the indentations of Eddie's knee, the sinewy lines along his shin. He placed a broad palm flat on Eddie’s thigh, the heat seeping through the shorts. He ghosted his thumb along the sensitive inner crease of Eddie’s hip, where the leg met the torso, just inches from his trapped cock.
Every nerve in Eddie’s body felt alive, singing. Each touch was a spark.
Robert’s fingers found his hips, hooking them, and then, finally, he pulled the soaked blue shorts and thong down in one smooth motion. Eddie, caught in the spell, shucked the damp vest over his head.
He was now utterly naked in the middle of Robert’s study, his cock already rigid, straining upwards to tap his belly.
Robert sat back on his heels, appreciating the view. "Your legs," he said, his voice a husky scrape. "These thick, perfect columns. A painter's dream." His gaze drifted upwards. "The trail of hair from your navel… God, it’s magnificent. It frames it all." His eyes finally locked onto Eddie’s cock, a thick, heavy vein running along its underside, the head swollen and slick."And this. This is a piece of art, Eddie. Honestly."
He spat delicately into his own palm, once, twice. Then he reached for the water bottle, poured a small amount over his wet hand, and mixed it with the drying, slick residue on Eddie’s cock from their earlier release. The friction created a perfect, reactivated slip.
Robert didn't lean in to swallow him. Not yet. He was in no hurry. He placed his wet hands on Eddie’s hips again, stroking the jut of bone. He dragged his thumbs inward, tracing the lines of Eddie’s groin. He bent forward and took one of Eddie’s nipples into his mouth, sucking gently, his tongue flicking the hard bead. A shudder ripped through Eddie.
Still on his knees, Robert leaned further, pressing his bearded face into the soft skin of Eddie's belly. He kissed him there, then nuzzled higher, his thick, hairy abdomen brushing directly over the swollen head of Eddie’s cock. The prickle of hair, the heat of his skin, the maddening, feather-light contact was exquisite torture.
Eddie groaned, a long, ragged sound. "Robert… please…"
"Please what?" Robert murmured, his breath hot on Eddie’s lower stomach.
"Your mouth."
That was all it took.
Robert pulled back, the hunger now matching Eddie’s own in his dark eyes. He shifted his weight, adjusted his posture, angled his head just so. He opened his mouth wide.
He swallowed Eddie in one smooth, devastating motion.
Eight solid inches vanished into that hot, wet cavern. There was no slow taking, no incremental slide. It was instant, total conquest. The blunt head pushed past Robert’s soft palate and into his throat, and then his nose was nestled in Eddie’s thick pubic hair.
Eddie’s hands flew to Robert’s head, his fingers tangling in the gray-streaked mane. The sensation was world-ending. It was the same shocking, impossible depth he had felt before, but now, with the recent memory of what it took to do this to another man, to Robert himself, it was nothing short of a miracle. The practice with the dildos made the scale, the stretch, the surrender all real to him. His mind fractured in a kaleidoscope of understanding and raw, visceral pleasure.
Robert barely moved his head. He hummed, a deep, vibrating buzz that Eddie felt in his very bones. That was the true mastery. The action was internal: the rhythmic, powerful squeezing of Robert’s throat muscles, a peristaltic suckling that massaged Eddie’s entire length from the inside. It was a polished skill, a talent turned art form, a welcoming, tight heat designed to pull the seed directly from its source.
He didn’t need to move. He swallowed. He swallowed again. His throat worked Eddie’s cock.
The coil in Eddie’s belly snapped in a matter of minutes. His orgasm was ripped from him, a harsh shout echoing in the book-lined room. He bucked forward, hips stuttering, emptying his load in deep, pulsing ropes directly down Robert’s gullet. Robert kept him there, swallowing easily, humming his pleasure as Eddie spasmed against his face.
When the last shudder faded, Robert did not let him slip free. He kept Eddie’s softening cock in the warm grip of his throat, his nose still pressed close, as if breathing him in. He stayed like that for two full minutes, a living, breathing cocksheath, while Eddie trembled from the aftershocks and the sheer, possessive intimacy of it.
Then, slowly, Robert began again. With Eddie still partially buried in his throat, he started to move—just a little. Tiny, precise bobs of his head, his lips sealed tight around the base. Eddie’s cock, sensitive and spent, responded reluctantly, then eagerly, as blood surged back. Robert’s mouth was a resurrection. He used more tongue now, swiping along the frenulum, swirling over the sensitive crown. His hands came up to cradle Eddie’s heavy balls, rolling them in his palm, a gentle, distracting pressure.
“Oh, God… again…?” Eddie whispered, disbelieving.
Robert hummed an affirmative around his mouthful. The vibration was the answer. He wasn’t just giving; he was taking, feeding from the hardness in his mouth, drinking from Eddie’s youth and need. He switched to a sucking technique, creating a vacuum that seemed to pull Eddie’s soul out through his cock. He’d stop sucking, just hold, then suckle again, shallow and quick.
It was a different kind of skill. It felt like being milked. Eddie’s second climax was a softer, deeper welling, more fluid than explosive, a yielding release that Robert drank down with quiet, pleased sighs.
A three-minute rest. Robert kept the tip of Eddie’s cock resting on his tongue, licking it like a precious lollipop, his eyes closed in meditative pleasure. Eddie was a wreck, legs shaky, head swimming. He couldn't believe Robert was taking him here again, as much as he'd hoped he would.
The third time, Robert fused both previous techniques into something unbearable. Deep throat swallows combined with that expert, hollow-cheeked sucking. His hands gripped Eddie’s ass now, fingers digging into the firm muscle, pulling him subtly but insistently deeper with each tiny thrust. He was active, hungry, a man possessed by the act itself. The sounds were obscene—wet gags that Robert expertly controlled, slurps, the quiet, choked grunts of a man savouring a meal. Eddie knew Robert was rock-hard himself, precum soaking the front of his own shorts, but that seemed irrelevant to his singular focus on Eddie’s cock.
Eddie cried out, a broken sound, as he came a third time. It was more a trickle than a flood, a weak, exquisite surrender. It was all of him, given. Robert swallowed it, and finally, finally, let Eddie’s spent, softened cock slip from his lips with an audible, wet pop.
He stayed kneeling, resting his forehead against Eddie’s damp thigh. They breathed together in the hushed room, the only sound the ticking clock and the ragged saw of their lungs. Robert turned his head, pressed a soft kiss to Eddie’s inner thigh.
"It’s magnificent," he whispered, his voice utterly wrecked. "You’re magnificent."
And Eddie, hollowed out and remade, believed him.