Krissa seemed, for the moment, content on watching me tremble whilst the machine slowly worked me to another orgasm I could do without. My balls felt like they were burning, my shaft numb and sore and my cockhead about to explode in more ways than one. It was amazing to me how my body still had the capacity to feel what radiated from my cock, and why I didn’t faint from the intensity of everything. Then again, my capturer wasn’t human, and her methods probably weren’t either.

“Please...” I whimpered, shivering where I lay at the mercy of the demoness. “I... I c-can’t c-cum ag-gain...” I stammered, sweat seemingly pouring down my face.

Krissa flashed an amused smile, and then looked at my manhood imbedded in the milking device. “You can’t?” she turned back to face me, still smiling. “I think you can. After all, you’re still hard.” She brought her face down, and planted another kiss on my lips.

I had to assume that the only reason my cock was still erect after all this time was only because of whatever Krissa injected into me with each kiss. If not I could only hope it had the common decency to go limp and spare us both these feelings. “P-please...” I stammered, feeling perilously close to my next orgasm. “I... I... I c-can’t...”

Raising her eyebrow as if to say “you so sure about that”, the demoness snuggled against me, one leg wrapped over my stomach as she watched the device go up and down my cock. “Let’s see if you can’t...”

I tried to plead further, but the slower setting of the ever-churning machine knocked me off my senses when another orgasm ravaged me. Though the lesser pace of the inside sleeve made the orgasms less intense, it was still mind-numbing. My hips thrust by their own, and my fingers and toes crunched as hard as they could. I let out a long, ragged moan, my body spasming while the milking-machine slowly worked me over. A short moment later, two trickles of cum dripped into the waiting glass jar.

“See?” the demon asked with pleasure. “You can cum more!” she raised her head to look at me, those fearful red eyes regarding me with hunger and lust. “And you’ll keep cumming until that container is full!”

“N-no... p-plea-s-se...” I looked back into her eyes entreatingly. “It’s too much, I... I can-nnnn’t...” My hyper-receptive manhood played violently with my sweating body. “Please...”

Stroking my chin with her hand, as if reassuringly, Krissa said “You can, and you will.” She looked at the glass. It was still just a couple tablespoons over one fourth filled with my spunk. “In fact, my apprentice should be by any minute now.” She looked back at me, smiling knowingly. “I had planned for her to play with Lina, but now I think she’d learn more from helping you produce more cum whilst the machine milks you.”

“No-o...” I shook my head. Though many questions filled my mind, like who the apprentice was, why she would “learn more” by “helping me produce cum”, and if that even was possible. However, all I could utter was my desire to shut the never tiring machine off and get it as far away from my tenderized cock as possible.

“I think that is a good idea.” Krissa said giggling, more to herself than to me. “Then I can keep working on Lina, and prepare her for what’s to come later...”

***

Krissa re-gagged me when she had heard enough of my stuttering complaints, amused by it as she was, and continued to watch my cock with glee and fascination as I came twice more, maybe relinquishing two drops of sperm combined on both orgasms.

Then a door, previously hidden in the shadows, opened, and in the light from beyond the room stood a silhouette of a female figure. She entered, the door closing behind her to remove both the light and the door. Struggling to see as she came into view, I saw it was a stunningly beautiful girl, about in her early twenties by human time-measuring. She was naked, displaying a very impressive set of curves, breasts almost as large as Krissa’s with a ring pierced in each nipple, pale fair skin and shoulder-length brown hair. Her eyes were purple, and when she smiled at Krissa I saw that, like the other demonesses present, her corner teeth were noticeably longer than the other. But unlike Krissa and Lina, this one had a long tail sprouting forth from her lower back that ended in a pointed arrow, making her look more “stereotypically demonic”.

“Welcome Arielle.” Krissa smiled benevolently as the slightly shorter demoness climbed into bed on the other side of me.

“Hi mistress!” she responded merrily, and then looked at me, giving me a better view of her figure and those alluring purple eyes. “What a handsome human you have!” she grinned. “Is he the one you told me about?”

“He is.” Krissa said, almost proudly.

“I know I promised you would get to play with Lina today,” Krissa gestured towards the bound demoness, who were still enjoying her breather without any form of stimulation. “But I have another task for you that may prove more pedagogic.”

“What’s that, mistress?” Arielle asked, cocking her head to one side, sounding slightly disappointed.

At that moment the machine slowly made me cum again, making my exhausted body shift as much as it managed while I whimpered into my gag. No new drops of cum appeared in the suspended glass.

“As you can see, my sweet little human here have some trouble filling that.” She gestured with her head to the hanging container with my jizz. “And that only after a couple hours of milking.”

I wanted to cry out my discontent and desperation, but the post-orgasm saw my mouth doing something less constructive as I shuddered, the wet parts of the bed sheets that were drenched with my sweat clinging to my body.

“I want you to help him fill that glass in one hour. Can you do that for me?”

Again I wanted to protest. Fill the rest of the container in an hour? It was beyond impossible!

“Yes mistress!” Arielle giggled with delight, her tail swaying happily behind her.

“Good.” Krissa said pleased, and pointed to the shadow-covered corner where she found all her equipment. “You’ll find what you need there, and while you help our friend here I’ll tenderize Lina for the later sessions.”

“Yes mistress!” Arielle said eagerly, skittering over me, heading towards the corner.

Krissa left the bed too, looking back at me and said “I’ve taught her well. You two will have so much fun together.” Grinning, she too made her way to the corner, making sure to whisper something to Lina as she passed that made the bound demoness swallow hard.

***

“Pleased to meet you!” the tailed demoness said happily as she climbed back into bed and settled on her knees beside my head. She had brought a handful of items back with her from the apparent stockpile in that corner, and she put everything behind the pillow where my head rested, so I couldn’t see what it was.

I could only groan to respond, the lubricated sleeve of the milking-machine changing what it did to slowly take me to another dry orgasm.

Had I not been so painfully sensitive and aware of myself, I had probably stopped to admire Arielle’s body some more. Her breasts looked really soft and tasty, the silver rings in her nipples seemed to gently tug on her areolas. Her pussy was clean shaven like the other two demonesses, which made me wonder if this was merely the style, or if demons had no hair-growth down there at all. Her skin was pale like Lina’s and Krissa’s, yet looking invitingly fair. Her hair was draping her beautiful face gracefully, and behind her, her tail was dancing gently from side to side.

“Looks like you have some trouble performing, huh?” the way in which she spoke, and the playful glances she gave me confirmed that she was indeed younger than both Krissa and Lina. “But we’ve ways around that that you humans probably don’t have!” she said excitedly, and taking some of the items with her, moved to settle on her knees between my legs.

She regarded the machine enveloping my cock with interest, her luminous eyes darting hither and dither on my crotch area. She looked especially at my balls, firmly tucked as far into my body as they could be as they did their best to feed my orgasms with additional cum, but it went without saying that the supply did not accommodate the demand.

“First things first...” she said and swept her hair behind her ears. Ears that were pointed in the way an elf’s ear was pointed, a feat she did not share with the other demonesses present, like her tail. Leaning down, she gently started suckling and tugging my worn balls with her mouth, one after the other and then back again, sending ticklish sensations that were less intense than those coming from my cock into my body. After a little while I somehow felt what she was accomplishing with this, as my balls slowly came back out of my body. The machine was still working me, very slowly, but my next orgasm weren’t many minutes away.

“There!” she said pleased when my balls were dragged out sufficiently, and grabbed them gently, cupping them in her palm. Humming softly, she proceeded to attach something around my balls where the scrotum connected with my crotch, and though I couldn’t see behind the tube around my cock, it was quite evident that it was a band of sorts. Moving on, I felt another band divide my balls, and a sensation of something clicking together. She had fastened a restraint on my scrotum, a thin leather band keeping my balls pulled away from my crotch, and another slim band that was attached to the first had been run betwixt my balls to separate them as well, before being fastened into the part that surrounded the upper part of my ballsack just beneath the cock to make a complete harness, that ensured my separated balls would be unable to retreat into my body again.

“Much better.” Arielle stated, and ran her fingers over my nuts, which I noticed had already begun to swell and become more achingly sensitive under the constricting leather. Continuing, she took a curved, small item in her hand. It looked like a hooked silicone toy, and I had a good idea as to what it was for.

“You’ll love this.” Arielle said, and sucked passionately on the curved end. She took it out of her mouth, a layer of saliva covering half of it, and showed it to me. The bent end was about six inches in length, and ended in the other end that was horizontal and about three inches long. “When I start it, this end will vibrate against your prostate,” she indicated the crooked part. “And this end will simultaneously stimulate your perineum.” She smiled, and seeing my unconvinced, nervous expression, she gently pushed the tip of the curved end against my butthole.

I flinched, the muscles in my ass tightening to stop the intrusion, but the demoness’ natural lubrication saw the end easily slipping into my butt, and the tip stopped to lean against my prostate. The level part of the toy that was outside of my butt, rested over my perineum under my bound balls. The sensation was strange, like when Krissa had been probing against my prostate with her finger, and like that time it didn’t necessarily feel uncomfortable.

“We’re soon ready.” She said cheerfully, taking a moment to watch the subtle strokes of the device on my cock, hearing it whirr and stir inside against my hypersensitive manhood that was closing in on another orgasm. “Great machine isn’t it?” she giggled, relishing the pained look on my face. “We’ll have to get your sperm production back to full, and though the ball-strap and the little vibrator here will do their part, the main thing we need is...” she purred, putting a finger on the milking-machine. “...is full juice.”

She dragged the finger down and off the silvery surface, and the device returned to the relentlessly overwhelming state in which it had milked me before. The warm and slick inner sleeve began sucking and rotating with renewed purpose, churning and pumping my too-sensitive cock and making it race towards my next orgasm painfully quick. Then the demon dragged her finger over the silicone-y vibrator in my ass, and it began vibrating mightily, the tip inside me shaking and poking against my prostate whilst the part of the toy outside of my ass began stimulating every inch between my anus and scrotum.

Deprived of strength, I still was somehow able to tug on my bonds and groan loud into the cloth covering my mouth. The burningly intense sensations in my cock was thrown far out of bounds by the stimulations in my prostate and perineum, sending shockwaves of forceful feelings up my shaft and into my erupting cockhead. My balls wanted to drag into my body, but the leather straps held them in place, which would prolong my unbearable climax with several seconds.

I came, even harder than I had before. I spasmed and yelped, my mind flashing white as my cock exploded with a blend of notions that no man was meant to endure at the same time. It felt as though three ounces of cum was shooting out of me, but it was only Arielle that noted how it was no more than three drops that dribbled into the glass.

“We’re on our way!” she smiled with relish, than looked at me thrashing weakly on the bed. “But we need to give it more time, and I’ll help you further...”

As I still whipped limply against the mattress, the tailed demon came crawling over my thigh, then straddled my hips, her butt pushing gently against the milking-machine and her breasts pooling on my chest. It made further gestures impossible for me, and though my manhood was ablaze with a combo of pleasure and hurting, I tried to communicate my pain to the sensual, pointy-eared demon.

She removed the cloth around my head and mouth nimbly as she softly hummed soothing tones, a look of serenity painted across her face.

“Puh... puh... p-pleaaaashhhhsse!!” I groaned when the gag was removed, the device still mercilessly chafing every inch of my cock.

Arielle held my face with her hands, and despite her nimble looks, she succeeded in holding my head steady. Leaning down, I smelled her scent, and it confused me with notions I had no words for.

“Krissa has undoubtedly told you that we demonesses have, shall we call it ‘special’ kisses.” She whispered, and I heard it despite my own moans. “And though I haven’t learned to release my pheromones like Krissa can, I can do something else...” she closed the short gap between our faces, and caught my mouth with surprisingly forceful strength, prying my lips open with hers, kissing me passionately despite my groans of painful bliss.

Letting my lips go, she looked directly in my eyes with her own purple, seemingly illuminating orbs, and whispered “My kisses will help you give the machine more of your delicious juices.” She kissed me again, and then the device forced me to come again.

Though the device in my ass and the kisses of the brunette had not been working long, I heard that the trickling from the tubing into the glass had increased, and Arielle could happily announce that six long drips of cum was the fruits of my latest orgasm.

“Let’s just cuddle like this for the next hour...” she hummed, and drew closer to kiss me again, her tongue invading my mouth whilst I clenched my eyes shut and tried to survive the current climax.

***

The hour crept painfully slow by, an orgasm being dragged out of me about once a minute. Arielle never moved from her position atop me, and kept kissing me whilst her hands sometimes moved over my chest and arms. Every time I came, the sensations heightened painfully high by the prostate-stimulator and the fact that my balls were unable to go into my body as they should, the amount of cum increased. It shouldn’t have been possible, but whatever demon magic was working together with Arielle’s toys and Krissa’s influences made my worn-out body produce more semen at an unfeasible rate, and the never satisfied machine took it all. And about thirty minutes later the container was three quarters full, something that would have taken me a week without Arielle’s help.

“We’re gonna have so much fun together...” Arielle took a break from frenching me, and rested her head on my shoulder as I spasmed from cumming almost thirty times in as many minutes, amazed that I had not passed out and was somehow still feeling. “I hope Krissa’ll allow me to fuck you later. After all, you’re really cute.” She giggled, and my stomach turned from the idea of my spent manhood having to endure more stimulation even after – indeed if – I was ever freed from the machine.

“H-howh longggg a-arrr you going to keep m-me here?” I gasped, already feeling the several extreme gestures of the machine working me against my next lavish orgasm.

“Hasn’t Krissa told you?” she looked at me quizzically.

I shook my head, fresh tears poking out of the corners of my eyes.

“Then I probably shouldn’t either.” She placed her head back on my shoulder.

“But I can tell you that orgasm-wise, we haven’t finished warming up yet...” she added with a menacing giggle, her slim tail gently swaying in the air.