The Triple Milker
#1 of Milking Stories
As usual, some no-preamble, straight-into-it tentacle fun, though this time with a fun group twist. Let me know what you think in the comments, or if you have any suggestions for stuff you'd like to see (I have an alternate version of this same story with sounding and watersports that I need to finish)
Gil yawned as he started to wake up. It had been a long night last night, out partying until the wee hours of the morning, and the otter had collapsed into bed last night as he got home, still wearing his clothes. That probably explained why he felt unusually warm, then. Yawning again, he tried to stretch out and pull the covers back... but weirdly, he couldn't move. Something was on his arm!
He slowly opened his eyes, but rather than seeing the bedroom he expected, he was somewhere very different indeed. The light was quite dim, but he seemed to be in some kind of large circular room - at least a few metres across - that looked like it had a weird fleshy texture; everything was glistening like it was covered in slime.
In the centre of the room was an odd, stumpy cylinder, rising to about shoulder height, that seemed to be pulsing slightly as it glistened in the dim light. He couldn't make out a lot of detail, but the outside looked like it was covered in bumps and ridges.
Then, however, he noticed the two others in the room with him. On the left side of the room was a dragon, with white and blue scales, and on the right hand side a red-furred fox - both completely naked. Even worse, they seemed to be pinned to the wall by a mass of slimy green tentacles wrapped around every limb; then, Gil realised why he couldn't move, and looked down to see himself in the same predicament.
He tried to call out to them, but as he moved his mouth he realised one of the tentacles was jammed inside it, and all he could do was let out a stifled "MmmmMMMMh!". This got the attention of the fox, though, who looked over at Gil with slight panic in his eyes. Gil looked around for a way out, but instead he found himself sneaking a peek at his two companions instead, their cocks dangling in full view.
It got the attention of the tentacles too, though - he felt them shifting around him, tightening their grip on his arms and legs, and a few more came out and wrapped around his torso. They avoided his groin, leaving his flaccid cock dangling there for the others to see - the idea did turn him on a bit, now he thought about it.
Just as he was trying not to get hard in front of the other two, a tentacle wove its way in front of his face, capped with some sort of bulb on the end. Before he could react, the bulb opened and sprayed him with some kind of gas; he couldn't help but breathe some in, its sickly sweet smell sticking at the back of his throat.
Suddenly, he felt an overwhelming urge in his groin, and he watched, helplessly, as his cock quickly hardened, his mind suddenly overcome with lust. He watched, gleefully, as the same tentacle sprayed the fox and the dragon, who was now awake and watching everything with a puzzled expression while clearly straining to try and escape the tentacles holding him down. Their eyes widened as they were overcome by the effects of the gas too, their cocks quickly growing to full size and standing proud out into the murky air of the room.
Gil had never felt anything like it - he was filled with an immediate need to fuck, but all he could do was struggle against the tentacles holding him to the wall as his cock pulsed with need. The dragon was struggling even harder, while looking over at Gil with obvious need, his eyes drawn to the otter's cock, while his own started dripping precum onto the already-moist floor.
Suddenly, the tentacles around all three of them starting moving, and Gil found himself being moved into the air towards the center of the room, his cock still dangling in front of him. They seemed to be taking them towards the cylinder in the center, but he wasn't sure what for.
As they got closer, though, he saw that there was a hole in the side of the cylinder, slime dripping out of it as it gently expanded and contracted. The tentacles lined him up for it, and just as he was ready to finally have something around his cock, they stopped, leaving the very tip of his penis just brushing the hole, making Gil moan in frustration.
He looked over and saw the other two were in the same predicament, clearly being held just out of reach as they squirmed with need; their groins were out of sight now behind the cylinder, but he was sure they were as hard and desperate has he was.
Suddenly, the dragon's tentacles plunged him forwards into the cylinder, his eyes closing and his face turning to an expression of pure ecstasy as he let out a long moan. The fox was next, the tentacles slowly easing him in this time as he let out a series of little groans as his cock plunged into the cylinder, and then a high-pitched yelp as the tentacles slammed him home.
Finally, Gil felt the ones around him shift, and they pushed him forwards, burying his cock inside the gaping hole. It felt warm and slimy, his cock brushing past ridges inside until he felt his body pushed up against the cylinder's warm, pulsating exterior, a low, uncontrollable moan coming from him as his cock was fully buried in the warm, slick hole of the cylinder.
He inhaled sharply as he felt the hole contract, squeezing his penis further along and rubbing it against some of the ridges, and then quickly started a series of small moans as it relaxed and contracted, rubbing his slime-coated cock along the ridged insides like it was trying to milk him.
He was already getting close to cumming, and as he looked over he saw the others were in similar situations. The dragon was breathing heavily and letting out grunts every few seconds, while the fox was almost shaking and letting out a soft whine as the tentacles held him firmly in place.
The dragon's grunts got louder and louder, and as Gil looked over, he tensed up, his eyes closing as his whole body clenched and he let out a loud grunt as he reached orgasm, his hips trying to thrust into the cylinder but the tentacles holding him firmly in place.
He kept grunting and thrusting, tensing every time, going longer than Gil had thought possible. After his third or fourth grunt, Gil felt a warm liquid around his cock, more rushing in with each grunt the dragon made.
It started filling up the hole and dripping out around his cock, the contracting and expanding of the hole squirting it out with each thrust. He looked down, and saw the dragon's cum dripping out of the hole onto the floor, as more and more hot cum flooded past his cock, dripping onto his balls and all over his legs.
The cum was making the inside of the hole even more slippery, and even once the dragon finally stopped cumming and slumped into the tentacles holding him, visibly exhausted, the milking action of the hole around his cock kept the dragon's cum pumping over his cock, making slurping sounds as more and more of it dripped out of the hole onto him, a puddle forming on the floor.
The idea of his cock being milked surrounded by the cum of the now-quiet dragon was too much, and as his body tensed up, the hole must have sensed it as it sped up its contractions. Gil's entire body shook as he shot his load into the hole, and load moans came out of his mouth as the hole milked his cock, squeezing it after every spurt.
Normally, he only came a small amount, but as the hole kept squeezing him he kept cumming, his entire body tensing up as he shot load after load into the hole. He felt it pooling up and leaking out, mixing with the dragon's cum, and based on the gentle moans of the other two, it was dripping onto them too; the fox looked over at him, blushing hard as he continued to whimper and shake, the tentacles holding him completely still.
Finally, Gil stopped cumming, and the hole stopped its contractions, leaving his softening cock buried in its warm, cum-coated insides. The fox was still whimpering, and as Gil looked up from his post-orgasm haze, he started shaking more and let out a load moan as he, too, came hard, his entire body tensing up with each spurt.
Gil felt the fox's hot load flow into the hole and around his half-flaccid cock, running out onto his balls and dripping onto the floor, as the fox came again and again, his moans getting weaker each time as he came twenty or thirty times.
Eventually, he too stopped cumming, and the three of them looked at each other, satisfied grins on their faces. The tentacles pulled them slowly away from the cylinder, and with a slurp, Gil's cock came free from the hole, dripping with cum and still semi-hard.
He looked over at the other two, and like him, they were covered in cum from the waist down, their combined loads soaking both them and covering the floor. Just as Gil relaxed, though, the tentacles stopped moving him backwards and instead started moving him to the left - to where the dragon was.
In fact, all three of them moved to the left, and as they brought him to a stop where the dragon had been, Gil realised he was lined up with another hole - this one looked different, though, as it seemed to be wriggling, cum dripping out of it as it jiggled around.
Then, slowly, Gil found himself being pushed towards the hole. He let out a worried moan - there was no way he could cum again. Still, the tentacles kept pushing him in, and as he got closer to the hole a small tentacle lifted up his cock so he slid straight in, his cum-covered cock making a slurping noise as it slid into the dripping hole.
As his cock slid inside, though, he realised why the dragon had cum first - this hole was full of tiny, wriggling tentacles, surrounding his penis. As he pushed further in, they wriggled and rubbed every part of his cock, slick and already covered in the cum loads from before, quickly making him hard again.
The feeling of the warm, tentacle-filled hole had Gil moaning almost immediately, and as he watched, the dragon and fox were plunged into their new holes, the fox letting out a series of moans as he entered the one Gil had been at before - he recognised the pattern of contracting he'd been subject to only minutes before.
The dragon's eyes widened as he was thrust into the fox's old hole, staying completely quiet until he was fully inside, when suddenly he emitted a surprised grunt, as his expression turned into one of fear. Gil started to wonder what was going on, but the tentacles around his cock started moving faster and rubbing his cock in every direction, and he had to close his eyes as he succumbed to the sensation.
He felt something moving, and gasped as a long, tongue-like tentacle started sliding out from the hole along the bottom of his cock, covered in slime and cum. It slowly moved down and along his balls, curving around and up to his ass. Gil tensed up as it pushed inside, unable to keep it out as he was still so focused on the tentacles rubbing his cock.
The tentacles on his cock started running up and down it in patterns, reminding him of the milking hole from before, when suddenly the tentacle in his rear pressed up against his prostate, making him moan loudly and tense up. It let off pressure, but then it slammed back down, and started fucking him in time with the tentacles in the hole, quickly taking him closer to cumming.
Meanwhile, the dragon was shaking and letting out a series of low, soft moans, looking over at the other two with a mixture of envy and lust. He was trying to move his hips to thrust in and out but the tentacles were holding him completely still, and all Gil could do was look into his desperate eyes as the tentacle in his ass kept pumping against his prostate.
Gil felt himself coming close to orgasm, and as he tensed up, the tentacle in his ass slammed into his prostate one more time, sending him over the edge as the tentacles in the hole massaged up and down his cock. His entire body felt like it was cumming as he shot load after load into the hole, the tentacle in his ass pounding away and squeezing out squirt after squirt.
His cum quickly started pooling inside the hole and leaking out around his cock, dripping onto the floor with a slurping sound as the tiny tentacles inside continued to stroke his cock as he covered them in cum.
The dragon moaned slightly as Gil's cum reached him, and the fox looked over with a desperate expression as Gil pumped the last few spurts into the hole before the tentacles inside stopped moving, and the one in his ass pulled out with a wet "plop". He was covered in even more of his own cum, and the entire side of the cylinder was dripping as more leaked out of the hole.
He heard the fox's moans increase in intensity and looked over to see him tense up as he came, his eyes closed in pure bliss as he emptied another huge load into the hole. Gil felt warm cum rush around his semi-hard cock and out of the hole as the fox continued to cum, the hole milking him dry after another good thirty or forty spurts - Gil swore they both came more than before, even though he didn't think he had anything left after the first time.
The dragon let out a frantic moan as the cum presumably reached him, still shaking and unable to really keep his eyes open, still straining against the tentacles holding him in place. As Gil and the fox both watched in post-orgasm bliss, the pitch of the dragon's moans increased more and more, until finally, several minutes later, he let out a loud grunt as he tensed up, his warm load flowing past Gil's now flaccid penis and onto his balls and legs, the pool of cum on the floor from all three of them getting even bigger.
Gil's cock slopped out of the hole as the tentacled pulled him away, and he hoped that was it - after all, there was no way he could cum again. Just as he thought he was fine, however, the tentacles starting moving him to the left again, and he let out a desperate moan as the tentacles lined him up in front of the last hole.
This one looked different, too - a cross-shaped slit, oozing fresh cum from the dragon's recent load. As the tentacles brought them in closer again, the small tentacle returned to help push their now-flaccid cocks into the holes, Gil's slipping in easily to the dripping slit.
As the tentacles pushed him inside, though, his penis pushed into a loose, smooth tube; no ridges, no smaller tentacles; in fact, nothing to stimulate him at all. The other two were already moaning away; the fox as the tiny tentacles caressed his cock, and the dragon grunting as his hole pulsed around his cock.
Gil looked at the other two, and they both looked at him with an expression that made it seem like they were sorry, when he felt something brush past his flaccid cock and let out a surprised moan.
Before he could even react, he felt it again, brushing past the end of his cock. Then, suddenly, he felt something wrap itself round his cock head, and as the tentacles tightened their grip on him, it started to slowly rub his cock head.
Gil was quickly getting hard, and as his cock grew into the hole, the thing rubbing him retreated backwards, so it was only ever touching his glans. He tried to thrust forwards to get some stimulation on the rest of his cock, but the tentacles just tightened their grip even more, pinning him in place and leaving the rest of his cock in the smooth, stimulation-free hole.
The fox and dragon were already grunting hard as they were sucked and pounded by their holes, and all Gil could do was struggle as the thing in the hole continued to rub against his cock head, the tiny ridges and bumps in it making him super sensitive and desperate for his whole cock to get attention.
It started rubbing his glans in circular motions, focusing on his urethra, and he found himself starting to shake from the pleasure - the rest of his cock begging for stimulation but getting none.
Suddenly, he heard loud grunting, and looked up from his torture to see the dragon cumming hard, his expression one of pure bliss as he came into the hole. Gil felt the dragon's hot cum flow past his cock head and moaned at the sensation, the slick cum making the rubbing even more intense and making him even hornier.
The dragon kept cumming and cumming, the cum flowing out of the loose hole easily and splashing all over Gil and the floor, bathing his whole cock in warm gooeyness while his cockhead was relentlessly rubbed and massaged. He started moaning every time the thing on his cock circled around his glans, getting more tense and shaking more as it made him even hornier but seemingly getting no closer to cumming.
As the dragon's cum flow subsided, Gil heard the fox start grunting too, and felt a fresh load of cum around his cock, flowing out of the hole as the fox grunted and moaned on the other side of the cylinder.
The thing on his cock head changed from circling to rubbing back and forth, and all Gil could do was moan and grunt as it edged him closer and closer to orgasm, his whole body shaking from the pleasure. As it rubbed back and forth, he felt his orgasm slowly building in a way he never had before, his cock head feeling so sensitive as it was rubbed and edged.
He looked up to see the other two slumped into the tentacles holding them, looking at him as he let out uncontrollable moans and grunts. He felt himself getting closer and closer to orgasm, and whatever had been rubbing him encircled his entire cockhead and started pumping up and down in small motions, going almost far enough down to reach the shaft but not quite.
It was enough to take Gil over the edge, and as his moans got higher and higher in pitch, he finally came into the hole, the thing inside continuing to rub his sensitive head as he came in spurt after spurt, causing him to shake as he came again and again, the rubbing seemingly never letting up, his cum erupting out of the hole and onto the floor, covering him in the process. Finally, his orgasm subsided, and the rubbing stopped, leaving his spent cock throbbing in the smooth, featureless hole, and Gil panting as he finally got to relax after the ordeal he'd just been through.
The tentacles pulled them away again, and this time pulled them all the way back to the wall, where they'd been at the start of all this. Gil couldn't think straight - his cock was still occasionally pulsing with the orgasm he'd just had - and as another tentacle sprayed them with gas, he had just enough time to wonder what it was for before he fell asleep again, his cock still dripping cum.