Chapter 5: Insertion
The next week began with a familiar ritual. A soft thud outside his bedroom door signaled the arrival of another plain cardboard box. Billy’s heart leapt, a Pavlovian response to the promise of connection and discovery. He retrieved it, his hands trembling slightly as he carried it back to the safety of his bed.
Inside, nestled in biodegradable packing peanuts, was a treasure trove. The same model of prostate massager he’d seen James use on screen, its sleek silicone curve both intimidating and alluring. A new, larger bottle of their favorite thick, clear goon lube. A simple douche bulb with detailed instructions. And a flat packet containing a rainbow assortment of eight silicone cock rings.
He immediately grabbed his phone. BRO, WHY ARE YOU THE BEST, THOUGH, BRO?
The reply was almost instantaneous. BECAUSE I KNOW WHAT A BRO NEEDS TO BE ABLE TO MEET HIS NEEDS. I GOT YOU, BRO.
A few minutes later, after fumbling with the packaging, Billy had all eight rings stacked haphazardly around his shaft, a tight, colourful tower constricting his flesh. He snapped a picture, his dick looking comically bound, and sent it. AM I DOING IT RIGHT, BRO? 😂
James’s response was the same crying-laughter emoji, followed by: HAHA. I'LL GIVE YOU A DEMO LATER, BRO.
As the hour for their session neared, Billy’s anxiety began to coil in his gut, centered entirely on the prostate massager. The douche, however, seemed like a manageable first step. He took the bulb into his private bathroom, locking the door. He read the instructions three times, his brow furrowed in concentration. The process was clinical, strange, but surprisingly straightforward and cleaner than he'd expected. When he was done, he felt an unprecedented sense of internal cleanliness, a blank canvas that was both weird and empowering.
He logged on at exactly 9:00 PM. James was already in the lobby, his camera feed showing him leaning back in his office chair, a knowing smile on his face.
“Hey, bro,” James’s voice was a warm rumble through the headset.
“Hey, bro,” Billy replied, his voice a little tight.
“You ready for your demo? Let’s see those rings, bro.”
They undressed quickly, the familiar ritual settling Billy’s nerves. James held up his own set of rings. “Okay, bro, pay attention. This isn’t just about the shaft.” He deftly slid a thick black ring around the base of his cock and balls, pulling his sac through the loop. The effect was immediate; his balls looked heavier, his cock somehow thicker and more veiny. “You can do just the balls, bro, to make them swing low and full. Or you can do behind the junk, right at the taint, to really make everything pop.” He added another ring just to his shaft, and a third behind his balls. “Or you can combine that shit, bro. Get the whole package locked and loaded.”
Billy followed his lead, his hands clumsy but eager. He put one around his balls, the gentle pressure a strange new pleasure. He added another to his shaft, and the blood began to pound, his cock hardening to an almost painful degree.
“Fuck, bro, look at you,” James groaned, his hand already working his own ringed erection. “Your dong looks so huge, bro. So red and thick, bro. Now bate, bro. Let’s see what it does.”
Billy’s hand, slick with lube, wrapped around his constrained flesh. The sensation was incredible. Every stroke was intensified, the tightness forcing the blood to stay, making every nerve ending scream for release. The pressure built faster and harder than ever before. He was panting, his eyes glazed over, watching James do the same on the screen.
“Oh, fuck, bro! BRO!” James shouted, his body tensing.
The word was a trigger. “BRO! FUCK, BRO!” Billy yelled back, his own orgasm erupting from him in a violent, blinding wave. Thick ropes of cum shot across his stomach, his body convulsing with the force of it. They came almost in unison, a symphony of guttural shouts and the word “bro” repeated like a sacred mantra.
They collapsed, laughing and breathless, the rings still in place. After cleaning up and a brief, distracted round of their game, Billy’s curiosity overcame his fear.
“James?” he ventured, his voice small. “The… the other thing. The massager. I’m… I’m nervous, bro.”
James’s expression softened into one of gentle authority. “I know, bro. It’s a big step. But you did the prep, right? You’re clean?”
“Yeah. I did. I’m clean.”
“Good. That’s the most important part, bro. Now, we go slow. Forget the toy for now. Just lube up your finger. Your middle finger. Nice and slick. Now, just… stroke around it. Don’t even think about going in. Just tease the outside. Get it used to the feeling.”
Billy obeyed, his heart hammering. He coated his finger and slowly, tentatively, brought it to his hole. He circled the tight ring of muscle. A jolt, unlike anything he’d ever felt, shot up his spine. It wasn’t just pleasure; it was a deep, neurological unlocking.
“Oh, wow,” he breathed.
“Good, right, bro?” James was watching, his hand idly stroking his own cock. “Now, bring that finger to your nose. Smell it. Check it.”
Billy, mesmerized, did as he was told. He inhaled. It smelled clean, like soap and lube, but underneath it was something else, a deep, earthy, profoundly masculine scent. “It’s… clean. But it smells… earthy. Nice.”
“That’s your ass musk, bro,” James said, his voice reverent. “That’s precious. Like pit musk. That’s the real you. Now, when you’re ready, just press a little. One finger. Let it in.”
The initial resistance was startling, but Billy relaxed, exhaling, and the tip of his finger slipped inside. The feeling of being filled, even just that little bit, was overwhelming. His cock, which had been soft, sprang back to life, leaking precum onto his stomach.
“Fuck, bro, can I add another?” Billy gasped, already trying to work a second finger in alongside the first. "Easy, bro," James said quickly, "Gotta be kind to your bussy, bro. First, go in a bit further with that finger. That's it. Then, bro, you want to circle inside your hole. Like pulling the ring outwards as you circle, bro. That's it bro. How does that feel?" Billy's groan was enough to confirm. "OK, bro. Now add the second." The stretch was intense, a burning fullness that translated directly into pure, undiluted pleasure. He was panting, his hips starting to move on their own, fucking himself on his own fingers.
“Now the toy, bro. Get the toy. Lube it up real good.”
Billy fumbled for the massager, coating it liberally. He positioned the curved tip at his entrance, now loose and eager. He pushed, and it slid in smoothly. The first thing he noticed was that he felt full. It wasn't unpleasant. The pressure and stretch were very new, so Billy knew he might not enjoy it right away. "Now, get the remote and turn it on." Billy did and the designed curve began vibrating and pulsing instantly against a spot deep inside him that made his vision whiten.
“OH MY GOD!” he screamed. His body seized. His hand flew off his cock, but it didn’t matter. Waves of pleasure were crashing through him, originating from that internal point of contact. His cock jerked violently, untouched, and began to spurt. Thick, helpless pulses of cum shot out of him, coating his chest and stomach as his legs trembled and his back arched off the bed. He was gooning, spasming, completely out of control, a raw vessel of sensation. When the last tremor passed, he collapsed into a heap, a breathless, uncontrollable giggle bubbling out of him. He was utterly spent.
On the screen, James was groaning, his own release painting his hand and stomach as he watched Billy’s transcendent breakdown. “Fuck, bro… that was the hottest thing I’ve ever seen.”
The week settled into a new rhythm. The next night, James was firm. “We’re giving your butt a rest tonight, bro. It’s a sensitive area. You gotta let the tissue recover or it can get irritated and sore. Not fun, bro.” They used just the rings again, their orgasms fierce and satisfying in their own right.
The following night, they returned to the massager, Billy now eager and confident, his body humming with the memory of that hands-free peak. After another shuddering, mind-blanking climax, James looked seriously into the camera.
“You gotta listen to your body, bro. Any change in how it feels back there, any pain, you tell me immediately. This is about feeling good, bro. Always. I got you, bro.”
“You got me, bro,” Billy whispered, the words meaning more than just their literal sense. He was floating, safe in the confines of his room and the boundless territory James was helping him explore.
The floating sensation lasted through Thursday, a buoyant haze of lube-slick fingers and the deep, internal thrum of the massager. But by Friday evening, a familiar dread began to seep back under his door, coiling in the pit of his stomach. James’s tone during their final session was different, softer, more deliberate.
“Sarah and I have that wedding this weekend, bro. Up in the Lakes. No signal where we’re staying, so no contact until Sunday night. No gaming. No gooning together.”
Billy’s breath hitched. Two days. A void. The safe walls of his room suddenly felt thinner, the world outside pressing in. “Okay,” he managed, the word tight.
“Listen to me, bro,” James’s voice was a firm anchor through the headset. “This is good. This, here with you, is what I always want to be doing. But also living my life with Sarah is important. And this is what you need to be doing for yourself. Owning your needs. I’m not abandoning you. I am empowering you, bro. You hear me?”
“I hear you, bro.”
“You've got your tablet with plenty of distractions," James purred, making Billy grin wildly. "And I’ve got one more thing coming for you tomorrow. A tool. Use it. Think of me. But own it. This is your time, bro.”
Saturday morning, the parcel arrived with the same soft thud. His phone buzzed simultaneously with a text from his mum. "JAMES IS BEING SO GENEROUS WITH YOU, HONEY. I HOPE YOU'RE SHOWING HIM HOW GRATEFUL YOU ARE, HONEY, X"
Billy’s cheeks flushed with a complex heat—guilt, possessiveness, a thrill of their shared secret. "I AM MUM, PROMISE, X" he typed back. He wasn't lying.
Inside the box, nestled in plain packing paper, was a clear, silicone, six-inch dildo with a strong suction cup at the base. A simple note was tucked beside it. "EVERY BRO HOLE NEEDS ATTENTION, BRO X"
Billy’s eyes lit up. The object was both clinical and profoundly intimate. Desperate to fade into a deep goon haze, but knowing he would enjoy it more if he got himself sorted out first. So, after a quiet breakfast where he forced down two pieces of toast, he returned to his sanctuary and began to tidy. He gathered the month’s worth of soiled socks, the crusted towels into the laundry basket; the empty lube bottles and used tissues into the bin. The anticipation was a physical ache, a slow burn he wanted to savour.
He decided to take the washing down himself with his full bin liner. The hallway seemed longer, the stairs steeper, but he focused on the task. His mother looked up from her book, a surprised look gracing her face. “Oh, Billy! What are you...? Oh. Oh! Well, ok, that's wonderful. Here, let me just show you how the machine works, honey.”
He listened, nodding, as she explained the dials and detergent compartments. The domestic normalcy was a bizarre counterpoint to the filth awaiting him upstairs. He filled the machine, started the cycle, took the trash out and fled back to his room, the receding hum of the washer a promise of cleanliness that only heightened the depravity to come.
In his bathroom, he used the douche bulb with practiced efficiency now, the water running clear until he felt utterly empty, a clean slate. He spent the next hour scrolling through gaming forums on his new tablet, one hand idly stroking his hole with a lightly lubed finger, remembering James’s instructions about patience, about teasing the nerve endings.
Finally, he could wait no longer. He suctioned the dildo firmly to the underside of a dinner plate and laid it on a box on the floor, high enough so he could reach it. He slid the automatic masturbator onto his penis, setting it to a low, persistent throb. Then he lay on his front, his knees tucked under him, his ass in the air, his head over the side of the bed. He guided the clear silicone tip of the prostate massager inside himself, setting it also to a low vibration. The dual sensations, internal and external, were immediately enveloping.
He lowered his head down towards the new toy, the mattress keeping the masturbator in place, his lips meeting the cool, slick tip of the dildo. He licked it, a tentative flick of the tongue, then took the head into his mouth, imagining the weight and taste of James’s cock. He began to suck it in earnest, bobbing his head, mimicking the scenes he'd seen in porn and the rhythms of his hands that he loved. He started to drool over it, remembering how much he loves a slick cock himself, gathering and reapplying the fluids as he sucked. He imagined James’s rough hands on his head, guiding him, and he deep-throated the toy until his eyes watered, gagging around the unyielding silicone, not quite able to reach the moulded balls.
The room filled with the wet sounds of his fellatio and the twin electric hums of the machines working his other holes. He lost all track of time, lost in a feedback loop of sensation. His body was no longer his own; it was a instrument being played by memory and need.
His first penile orgasm ripped through him unexpectedly, his cock pulsing violently into the stroking sleeve as he sucked hard on the dildo. The second came slower, a grinding, milking release as he relieved himself of mouthfuls of thick, viscous saliva, coating the dildo, leaving a pool of fluid swimming over the plate. In between, his prostate massager found its mark, and his body was seized by two mind-shaking, full-body orgasms that left him screaming into the toy, his voice hoarse, his limbs trembling uncontrollably.
He finally collapsed onto his side, spent, the devices still whirring against his oversensitive flesh. He missed James with a sharp, physical pang, a hollowed-out feeling in his chest. He took out his phone, took a serious of evidential photos of the last few hours and sent them to James. He wouldn't get them now, but they'd be waiting for him. "Nothing replaces my bro, but this was fucking magic. Love you bro." And as he lay there panting in the mess he’d made, a profound gratitude washed over him. This was a perfect distraction, a temporary salvation. He was alone, but he was not abandoned. He was learning.