A Sheath To Remember

This is an example of what you could get with a story commission! This guy had some specific requests, which I was all-too-happy to provide. Hope you all enjoy!

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Miles was honestly surprised that things were going as well as they were. He’d expected to have coffee and maybe a quick handy in the bathroom, but instead, Shawyn had asked him back to his apartment and even suggested a threesome with his boyfriend. It wasn’t that Miles was opposed to the idea; it was just that he’d come to the assumption that this was all happening on the down low, so to speak. He didn’t even know Shawyn was partnered until the day before yesterday.

But Shawyn was incredibly hot, and Miles wasn’t one to let an opportunity pass him by. So when a work trip finally put him in the same city as those dark eyes, washboard abs, and devilish smile, he just had to accept whatever conditions Miles proposed. And really, a threesome? Why would he say no? Odds are his husband was as hot as he was. 

The two met for coffee and then immediately went back to Shawyn’s apartment. As soon as Miles had crossed the threshold, Shawyn’s lips were on his, arms wrapped around the shorter man’s stocky, soft exterior, desperately unbuttoning and unzipping whatever he could get his hands on. 

For his part, Miles met Shawyn with equal enthusiasm. Why wouldn’t he? It wasn’t every day he got the opportunity to make out with someone who looked like a Greek god. It was enough for him to forget entirely how much their bodies contrasted—Shawyn like a medical textbook of lithe musculature, Miles an overweight ex-jock that barely came up to Shawyn's collarbone—but there was no denying a sexual chemistry between the two, and Miles had long ago forsworn questioning life's little gifts. He was a “go with the flow” kind of guy, especially when that flow was so appealing. 

The two soon shed their clothes and began to grind into each other in the middle of Shawyn’s living room, their mouths rarely parting for more than a blink. At some point, Miles looked down to see a shaft nearly twice as long as his own squishing into the soft bulk of his belly, and he gulped. He’d seen it in pictures the two had shared online, but seeing it in person was a different thing entirely. 

Perhaps sensing the shorter man’s brief disquiet, Shawyn dropped slowly to his knees, his tongue running down Miles’ chest, then stomach and groin, and finally to the tip of his cock before he took him to the root in a single quick motion. Feeling himself suddenly engulfed in Shawyn’s warm, wet embrace elicited an excited moan from the stocky man that became an extended groan as Shawyn’s head began to bob rapidly. 

Miles felt his excitement get the better of him. He tried to reach down and steady Shawyn, but he seemed too determined to take the not-so-subtle hint. Miles went rigid as he cried out and filled Shawyn’s mouth with seed, hands now steadying himself on Shawyn’s back and shoulders as he pumped several shots down his enthusiastic new friend’s throat. 

After a few moments, Shawyn stood with a white-smeared smile. “People tend to get pretty excited around me, so I like to get the first one out of the way,” he explained, grinning wider at Miles’ post-orgasmic look of confused contentment.

“Sure,” he managed, then stumbled over and collapsed on a nearby couch. Shawyn followed, his massive cock bobbing like the wagging tail of a playful dog. 

“So,” Shawyn began, arm wrapped casually over Miles’ shoulder as the squat man caught his breath. “My boyfriend should be back from work in 15 minutes or so, and I wanted to ask you something.” 

“What’s that?” Miles asked, first looking over at Shawyn’s smiling face before his gaze was drawn to the towering organ that occupied the bottom part of his peripheral vision. 

“Well, you might have noticed I’m sort of big, and my boyfriend… What can I say? He’s a power bottom. He’s definitely going to want you to fuck him, and I fear he’s a bit demanding.” 

Miles raised a quizzical eyebrow before realization dawned on him. He reached down to grasp Shawyn and was astounded by how he could barely get his hand around its girth. If this is what his boyfriend was used to, then Miles worried if there would be any friction for either of them.

Another thought occurred to him as he stared into Shawyn’s cobblestone abs. “Is he even going to… You know, like me?” 

“Oh, for sure!” Shawyn exclaimed. “Neither of us is really hung up on bodies. It’s all about attitude, y’know? And you’re great! He just—” Shawyn bobbed his head “—needs a big cock.” 

Miles looked down glumly at his modest erection, partially obscured by his stomach and still dripping cum from earlier. “I guess I could use a toy, if you have one.” 

“Actually,” Shawyn lept from the couch and wandered into another room, then returned with what appeared to be a dildo equal in size to the man’s own impressive organ. “You can use this.” 

What first appeared to be a dildo was actually a sheath, Miles realized. The core of the base and shaft was hollow, while a silicone band wrapped around the end so it could be anchored by the user’s balls.

“Why don’t you slip it on? Try it on for size?” Shawyn asked, tossing the stocky man a small bottle of lube. 

Miles shrugged, said “Fuck it,” and then squirted a generous dollop of lube on his still-hard cock. Then, he slipped the sheath over his dick, where it easily slid to the base. He finished by slipping his balls through the band, which had the added benefit of pulling them forward, making them appear even larger than they already were. 

The sheath was remarkably lifelike, Miles noted. If he couldn’t see where the material ended, he could almost be fooled into thinking this was his own towering erection curving over the circumference of his stomach to settle just below his chest. It almost felt like it was his own dickhead ruffling the hair of his torso. 

“Pretty hot, right?” Shawyn said, then reached over to squeeze the sheath. It felt like he’d just reached over to wrap his hand around Miles’ own shaft, and the shorter man gasped. A fog began to seep into his mind, slowing his thoughts and dulling the alarm he felt at these strange new sensations coming from his dick. It felt very good—maybe even better than his own, unsheathed cock.

“Wanna take it for a ride?”

Miles blinked, unsure for a moment who asked the question, before realizing it was the incredible figure smiling down at him and tugging at his cock—his massive, unbelievable cock. Almost as big as the one beside him. But hadn’t he been much smaller? He couldn’t remember. His recollection slipped away like trying to grasp at smoke. All Miles could think about was how good it felt to be touched, rubbed, and pulled. 

Shawyn started to pump the sheath in earnest as Miles' eyes lost focus and his tongue lolled out of his open mouth as he breathed heavily with growing arousal. By now, Shawyn could tell that the sheath had enraptured his mind in ever-increasing bliss, Miles now oblivious to everything but the magically-enhanced sensations that had so totally captured him. 

As a line of saliva began to fall from Miles’ rounded face, he didn’t even notice as the base of the sheath began to meld itself to his pelvis, or how the band surrounding his scrotum disappeared as its mass was added to his slowly descending orbs, both of which grew larger by the second. Once there was no distinction between what was once a sheath and Miles’ actual organ, a pearl of precum began to form at the tip before descending the enormous shaft, mirroring the fluid descending from his open mouth and helpfully lubricating Shawyn’s hand. 

“Liking it so far?” Shawyn asked, even though he knew Miles was well beyond responding. He merely sat and drooled as the sheath completely replaced his manhood with a far superior one. And then it transformed it further as a crease of skin formed just below the head, which soon turned into a wrinkle that bunched up and then spread over the glistening head. Soon, Shawyn’s hand slid easily as a foreskin mechanically aided the lubrication Miles’ new tool was naturally producing.

“That’s new,” Shawyn noted, but the sheath was never entirely predictable. The magical trap was designed to charm the victim while bestowing an unnaturally potent tool upon them, but all magic had inherent variance. Perhaps he’d accidentally made this charm a touch too potent? 

Shawyn got his answer moments later as the cock in his hands began to grow, stretching further up Miles' stomach until the head bobbed eagerly just below his chin. For just a moment, lucidity returned to Miles as he stared into the massive, seeping cockslit, but then he felt an incredible rush as his now enormous cock flooded his mind with sensation. His eyes once again went cloudy, and then his head fell back with a deep groan. 

A groan which deepened as it was met with an ominous creak from the sofa. Shawyn’s eyes went wide as he realized Miles’ growth wasn’t limited to his oversized genitals. The formerly short, stocky man was expanding outward before his very eyes, rapidly gaining both mass and volume. Long-dormant muscles bulged outward as his shoulders broadened and his chest inflated before both were obscured by a thickening mat of hair. His stomach, which was once a doughy roll that rested on his lap, rounded outward and solidified with brute strength. Thighs and calves rippled as they expanded into massive trunks that looked like they could lift mountains, a trait soon shared with every extremity the now elephantine man possessed. 

Shawyn was forced to evacuate the couch as Miles expanded to occupy its entirety. He stood and beheld the ogreish man, panting with pent-up desire and obviously in need of release. Miles’ cock still towered up his stomach, but seemed somewhat more appropriate to his overall size. 

But only somewhat. The thick hair, bulging musculature, and thickset frame gave Miles a brutish appearance, accentuated by a more blockish face and deepened brow. It was a far cry from his formerly boyish good looks. Shawyn shrugged. Miles was still granted the most important aspect, at least, for his partner, although Shawyn wondered if it might even be too big…

Without warning, Miles clutched the arms of the couch and began to huff like a locomotive. Shawyn realized he was bringing himself to orgasm even without his help, but he couldn’t let the brute spoil his first post-transformed orgasm. Shawyn dove onto the cock with his lips and mouth, rubbing it with his arms and body. It stretched nearly his entire torso, the broad head spewing gobs of precum into his face.

Then, Miles howled, and like a long-dormant caldera, he erupted in a sudden and violent explosion. The first blast struck Shawyn with enough force that his head snapped back like he’d been punched in the jaw. He fell back and wiped cum from his eyes as he watched Miles fiercely spasm, each jerk firing a stream of jizz several feet into the air to splatter loudly on the couch, floor, and Miles’ titanic body. His convulsions continued for nearly a minute, leaving a puddle of cum that looked like someone had upended a bucket of white paint. Then, with a final, grumbling huff, the torrent slowed to a mere burble that streamed steadily down Miles’ shaft, and the enormous man grew silent.

“Fuck,” Shawyn exhaled. He had no idea how he could clean this up before his boyfriend returned home.  

Thankfully, he needn’t have bothered. Not a few minutes after Miles’ eruption did Shawyn hear the front door open, followed by the rumbling footsteps of his partner, Teddy. He lumbered into the living room, took in the lewd diorama, and smiled broadly.

“Oh, hey! It worked!” 

Shawyn dropped his sopping towel and just stared at Teddy in naked disbelief. “You did this?” 

“Yeah. Hope you weren’t too surprised,” he winked, then lumbered over to the apparently dozing brute while casually disrobing, his work-appropriate attire leaving a trail from the door to the couch until he was as naked as every other occupant. 

The contrast between the three of them couldn’t have been starker. Although almost as large as Miles’ brutish form, Teddy’s rounded shape was the result of hedonistic excess. His stomach, which preceded him by nearly a foot, was a doughy, wobbling mass only matched by a titanic rear that nearly filled the doorway. His face, round and jowly, never seemed to cease smiling thanks to overfilled cheeks pushing up the corners of his mouth. He was the epitome of jovial obesity. 

He was also an unapologetic size queen. Teddy whistled appreciatively as he leaned over the slumbering beast far enough for his belly to rest against the sleeping man’s colossal cock. The friction was enough to startle Miles awake, who stared upward at Teddy’s grin with dim, almost animalistic eyes. 

“Wakey wakey, big boy,” Teddy chided, before reaching down to grasp the half-hard cock which was still the size of a baseball bat. “You like having this big fuckstick, don’t ya?” 

Miles nodded and grunted enthusiastically. 

“Ya wanna fuck somebody with it, don’t ya?” 

Again, Miles nodded, this time grunting with even more enthusiasm. Teddy chuckled, the vibrations of his belly playing deliciously over the rapidly stifening pole beneath him.

“Well, why don’t you follow me to the bedroom then?” With that, Teddy stood and turned, revealing cakes that could have fed all of 16th-century France. Teddy stepped on the balls of his feet so his globes danced enticingly with every step. By the time he was stepping through the doorway to the bedroom, both Miles and Shawyn were stiff as boards.

Shawyn looked over at Miles, who gazed back with dumb excitement, seeking permission to proceed as Teddy had suggested. The now-smallest man in the room nodded, and Miles stood to his full height of almost seven feet, his chest and shoulders so broad that his ham-sized fists hung knuckles-forward like an ape. His dick, almost as large as Shawyn’s arm, curved upwards, impossibly overcoming its own mass. Shawyn reached out and grabbed it, using it like a leash to lead Miles to the bedroom. 

“Do you think you might have overdone it a bit?” Shawyn asked as he entered. Teddy was already on the bed, on all fours, reaching with effort over his mass to lubricate his asshole, which winked invitingly. 

Teddy chuckled again. “Won’t know until I try,” he replied over his shoulder. “His pictures didn’t exactly fill me with confidence, so I erred on the side of not being able to sit right for a week. Now get that monster in here. It’s been a long day, and I’ve been looking forward to this.” 

With that, the light from the hallway dimmed as Miles entered the bedroom. Or at least tried to. He was now so wide that his arms blocked entry, and he had to shuffle sideways, sucking in his stomach and pulling his dick up so it was vertical. Once inside, he immediately became mesmerized by the humongous ass being shaken in his direction. The beast lumbered up to the bed, placed his meaty hands on Teddy’s equally meaty hips, and dove in face-first, his outstretched tongue punching through Teddy’s ring in a single thrust.

“Oh fuck!” Teddy cried out in surprise, not expecting to receive a tongue-lashing as his initial penetration, but quickly warming up to the idea. He moaned, face going slack as he relaxed into the bed, and he felt his hole open up similarly. Miles wasted no time diving in even deeper, his slobbery saliva mixing with the lubrication to make each globe as slick as a well-oiled machine.

Shawyn observed the scene for a moment before he came to the head of the bed and sat in front of Teddy, his more conventionally impressive dick slapping him gently on the cheek. “He’s really into it, huh?” 

“Mmmmm,” came Teddy’s muddled reply. 

“Hah, so are you, it seems.” Shawyn tapped his cock against the side of Teddy’s head again, then guided it to his mouth. “Now, open wide. Miles? I think he’s ready.”

The brute grunted in acknowledgement, still apparently lucid enough to remember his own name, although he didn’t immediately rise from his oral task. When he did, however, it was with the foreboding slowness of watching a tidal wave creeping up to shore. Shawyn stared transfixed at the enormous man’s breadth—just as wide as Teddy but of a very different character—as he lifted his club of a cock and pressed it against Teddy’s entrance. 

Despite his size, Miles was surprisingly gentle at first. Shawyn watched him tense, then slowly drive his pelvis forward until his head passed Teddy’s ring. Then he stopped, eyes staring intensely at Teddy’s rounded globes. It was as though Miles was concentrating with all his remaining focus just to avoid injuring the man he was slowly violating—a sure sign of Miles’ true character shining through even in his almost-monstrous form.

But then Shawyn watched as that focus began to crumble in the face of pure, bestial pleasure. As inch after inch disappeared into Teddy’s capacious backside, Miles’ eyes blinked, then grew cloudy. When his long tongue lolled out of a goofy smile, Shawyn knew whatever lucidity the man had reclaimed was gone. A step forward, and the brute’s pelvis met cushiony cheeks, and Teddy wailed in both pleasure and pain, only to be silenced as Shawyn shoved his cock in his partner’s open mouth. 

Miles didn’t wait long before he began to fuck Teddy in earnest, slowly pistoning in and out in long, full strokes, his lengthy dong requiring him to nearly take a full step backward and forward with each thrust. Neither did he restrain himself from hammering away at Teddy’s well-padded hole. The bedroom was filled with the sounds of meat slapping against meat and animalistic grunts and snorts. 

As he was harshly violated, Teddy messily sucked at Shawyn’s cock, his head bobbing in time to the brute slamming into him from behind. It was hardly the finest blowjob he’d ever received, but the sight of the massive beast plundering his partner was more than enough to make up the difference, and Shawyn felt himself rapidly approaching his peak. 

There was no sign that Miles was close to finishing, but the moans around Shawyn’s cock began to take on a desperate pitch. Then, Teddy let out a muffled squeal as he came, his corpulent body shuddering as he continued to be mercilessly pummeled. Shawyn heard a few splats as Teddy’s load emptied onto the mattress. Miles continued his pistoning, heedless of anything but his own base enjoyment. 

Shawyn came soon after, filling Teddy’s mouth to the point where he sputtered momentarily before he managed to swallow it down with a gasp. He slipped himself from Teddy’s mouth to watch his third, fourth, and fifth shots splatter against his boyfriend’s wide face, wincing in either pleasure or pain—it was impossible to know the difference. 

Finally, Miles' eyes widened, and then the brute howled as his enormous body spasmed. Teddy offered his own quieter note as he, too, shuddered in time with the beast’s convulsions, and Shawyn thought he heard another splat of cum empty out of his boyfriend, buried somewhere in his bulk. 

A gentleness seemed to return to Miles as his balls spewed their contents. His pistoning went to half-depth and speed as he used Teddy like a sleeve, holding him around his expansive waist with hands as big as dinner plates. And then, after what seemed like minutes, he grew still as he panted and drooled. Eventually, he took a step back and extracted himself with a lewd slurp, ejaculate following his club-sized organ to trail down Teddy’s thick legs and form a puddle on the bed. 

Teddy collapsed forward into Shawyn. “Holy fuck,” he gasped. “I don’t… I don’t think I can do that again.” 

“That’s fine,” Shawyn said, reaching down to stroke Teddy’s cheek. “It seems our special guest has run out of steam, too.” He gestured at the massive man, who’d fallen onto his back on the floor, eyes closed, tongue still hanging from his mouth. 

Teddy panted for a few moments, then settled and asked, “So, um, when does the sleeve come off?” 

“I don’t think it does,” Shawyn said. “But he should shrink back down to normal in a few hours or so.”

He did, although not truly back to normal. Miles slept as his body shrank slowly, but not to what it was. Although back to his former height, he retained an almost oversized breadth, his previous softness now barely obscuring a powerlifter’s musculature. And while his cock could no longer be described as a deadly instrument, it still rivalled Shawyn’s length and girth. He’d also retained his thick and wrinkly foreskin, which drooled cum even after an hour, thanks to similarly oversized testicles.

When Miles awoke, it was as though from a dream—a very horny dream. He remembered the blowjob, then sitting on the couch, and then Shawyn placing a sheath on him, and then it was as though he were trying to see through smoke. All he could recall was momentary flashes of a truly enormous man plundering an equally large ass, all grunts and moans and meaty thwacks and wet shlorps. And then he awoke on the floor, a changed man.

Yet he couldn’t remember what had changed. It was odd for his clothes to barely fit (one button had even popped off his shirt), but then again, most clothes barely fit him. He apologized for apparently dozing off, but Shawyn assured him that he’d performed more than adequately. Shawyn kissed him on the cheek as he left, promising to call him later. It was enough for Miles to blush, and for blood to rush to his groin. Miles heard his zipper strain, then burst with his excitement.