Jack in the Box

A man is kidnapped by demons and forced to pleasure them. He can either resist and experience pain or give in and enjoy the pleasure… I used my extremely limited art skills and a character generator to enhance this short story with images!

Tags: Feminization, Demon, Tentacles

Jack had quite a rude awakening. He had been sleeping happily when a bright red light suddenly filled his room. Weird red runes glowed in the darkness as they circled his body.

“What the fuck” Jack said, getting out of bed.

Jack tried to run out of his room, but as he moved, phantom red chains shot out of nowhere to grab his arms and legs. The runes began to circle faster, and the red light continued to glow brighter and brighter until it was all he could see. Jack closed his eyes, fearing blindness until it seemed the light had faded. When he opened his eyes, he was in a small room. It was longer than it was wide, maybe 3 feet wide by 8 feet long.

Jack looked around, trying to figure out what had just happened to him. The white tiles made up the floor, while the walls were light pink. It was bright enough to see, but Jack could not see any light sources. The same material as the floors seem to make up the roof. Jack knocked on the wall. Whatever material it was, it was pretty hard, with a smooth, cold texture. On one end was a mirror, which reminded Jack that he was wearing nothing but his boxers.

Further investigation revealed shelves built almost flush into the wall. Jack pulled a drawer out, revealing clothes. Most were girls’ clothes, but Jack found a long-sleeved shirt and a pair of jeans. He put them on, looking back at the mirror. A young college student looked back at him; his short dark brown hair was still slightly messy from sleeping. Jack wasn’t super tall but was skinny enough to make it appear that he was. He continued to search the room but didn’t find anything other than a switch that turned on a shower in one corner, water pooling before flowing down a small drain set in the ground.

However, Jack soon got his answer when a disembodied voice began to speak.

“Welcome, mortal. I hope you like your accommodations.” The voice was deep and had an echoing aspect, sounding to Jack like what one would imagine a demon’s voice sounds.

“Who are you? What do you want? Let me out!” Jack shouted, looking around to see if he could find the source of the voice.

“Oh, you shouldn’t worry about who I am. You will know soon enough. However, I do have an important task for you. You see, morale has been low in my kingdom lately, so I have set up a nice box with you in it so that you can help my underlings.”

“Doing what?” Jack asked. Every time he moved toward what he thought was the source of the voice, it seemed to shift to a different part of the room.

“All my underlings get quite pent up and need to be relieved. Your job is to assist them in any way you see fit.”

“And if I refuse?” Jack asked.

“Then you will experience pain until you comply. Like this.”

Red runes flashed in front of Jack’s face, and he yelped as pain assaulted his body. It was like every muscle in his body had cramped. He struggled to stand. The pain was excruciating but did not last long.

“I am a demon, after all, so don’t expect any mercy if you resist. Anyways good luck, my little pet.”

The voice faded away, leaving Jack alone. Another red rune appeared and began to glow on the wall. Jack moved away from it, not knowing if it would cause more pain or what else to expect. Soon enough, he got his answer as a limp red penis pushed through the wall, hanging there.

“He wants me to get demons off. What the fuck.” Jack realized. Still, the pain was fresh in his mind, and he slowly approached the cock. He reached out, touching the cock, which twitched.

“Well, he did say I can use whatever method I want.” Jack thought and grabbed the demonic penis with his hand. It felt warm, and Jack slid his hand back and forth. The sensation was enough to cause the cock to grow until it was erect, a couple of inches long. It was inhuman, with red flesh and patterns of ridges running down its sides. Touching the demon’s cock felt normal, slightly warm, and smooth skin. Jack continued to rub it for a while before it started twitching.

“Oh, fuck no,” he said, getting out of the way before a large amount of cum sprayed from the penis onto the floor. The cock then began to slide back into the wall through the rune. As soon as it left, a new dick appeared, this one purple and veiny. Jack sighed. It seemed he had a lot of demons to get off. Soon Jack lost count of how many demon dicks he had given hand jobs. At first, there was a new cock appearing as soon as he finished the previous, but after the first dozen or so, it slowed down to one every five to ten minutes. The real problem soon became the demonic cum filling the room, a large puddle forming.

Jack realized he was neither thirsty nor hungry. Nor were his hands sore despite the several hours he had spent milking demons. Some weird magic was afoot. After the latest monster had came, he looked through the clothes drawer and found a towel, which he used to wipe up the sperm off the floor before throwing the towel into the corner. When he did so, he glanced at the mirror and realized with a shock that his hair had grown. Somehow, without his realization, it had grown several inches longer and lighter, now a light brown.

“How long have I been in here?” Jack wondered. However, while he was checking himself in the mirror, a new customer arrived, this time with a bumpy green appendage. Jack sighed and got back to it. Still, there was a feeling of wrongness that lingered inside of him. Jack wasn’t even tired, and he was sure it had been at least a dozen hours since he had arrived.

Eventually, a lull arrived. Jack did not know what caused it, but he welcomed the break. His emotions were a mess. After all, a demon had kidnapped him to jerk other monsters off. Jack decided to take a shower to try and relax. He took off his clothes and realized that all his body hair seemed to have disappeared—another change.

Jack turned on the shower, enjoying the warm water on his body. Wherever the hell he was, or rather wherever in Hell he was, at least they had warm shower water. Jack stood there for a while, enjoying the water hitting his head and back. He closed his eyes as he did his best to relax. Maybe this was all a dream, and soon Jack would wake up in bed and swear never to tell another soul about it. Sadly, he was still in his box when he opened his eyes.

Jack sighed and turned off the shower. He opened the clothes drawer to grab his pants and shirt again, only to find them missing. Hadn’t he put the jeans back in the top drawer?

“This fucking demon is messing with me, isn’t he?” Jack swore. And it must have been because a new demon penis had appeared. Jack swore again and then went over. He didn’t even care if the demon felt pleasure, roughly grabbing and rubbing the dick. However, this was a miscalculation on Jack’s part, as the devil suddenly came without warning.

“Shit!” Jack was too slow and got demon cum all over his chest, warm liquid splattered across his still-naked body. The demonic cock began to recede, and Jack glared at it. He contemplated smacking it before deciding he rather not antagonize the head demon. It was stealing his clothes, even with his compliance. Who knew what it would do if he made it mad? He got up and used the demon cum towel to clean himself off before looking for a new pair of clothes.

Jack was sure there was more than one pair of pants, but now all he found were skirts and dresses. The worst was that the only underwear available was panties. Was it better to go commando or to wear those? Jack ultimately decided not to risk it and put the panties on. Surprisingly, they felt nice to wear; the fabric was all silky and smooth, the tautness feeling good on his butt. Why weren’t boxers made with this material? He then put on a yellow blouse and a light blue skirt. He looked at the mirror, and his reflection shocked him again.

Jack’s hair was even longer, almost to his shoulders and now was a strawberry blonde color. He got close to the mirror and peered into his eyes which had red irises and pupils like a cat’s. His ears had changed as well, now pointed at the ends. Jack knew that the box he was in was doing something to him. He needed to escape as soon as possible.

Demons continued to present their cocks, and Jack fulfilled his duty. However, as soon as Jack finished, he continued to try to find a way out. While the demon magic meant his body was slowly changing, it also meant Jack was immune to getting tired or his body getting hurt. Jack’s hands never hurt, no matter how hard he pounded on the wall. However, it was also true that no matter how hard he hit on the wall, the wall was unaffected. Pulling on the drain, showerhead, and shelf drawers also went nowhere.

Jack felt himself get more and more frustrated. And the more frustrated he got, the more he made mistakes, with more demons releasing cum on him. It reached a boiling point when Jack had just changed into another skirt and blouse when a monster with a curved penis released a massive load onto his shirt. Jack screamed in annoyance, standing up and pounding on the wall in frustration while he yelled various swear words. It took him a while to calm down. Luckily, another lull had appeared, and Jack’s tantrum slowly tapered off.

He turned to the mirror and glared at his reflection. His ears are now sticking out quite a bit, with pointed tips. His hair was still a strawberry blonde but was lighter and now reached down his back. His face was changing too, more feminine looking than before. He was kind of cute looking. No wonder the demons were cumming. Jack would, too, if someone looking like that got him off.

Jack began to feel warmth throughout his body as his frustration moved to arousal. Jack lifted his skirt, exposing his panties, a distinctive bulge visible. Jack couldn’t help himself as he reached down and began to feel his cock for once. He watched himself in the mirror, and seeing this girl in the reflection get him off only made him more aroused.

And, of course, as soon he had started to pleasure himself, that was when another demon just had to show up. He still hadn’t cum yet, and the desire to do so weighed deep in Jack’s mind. Jack was about to drop his skirt and go back to work when an idea came to his mind, a way to get revenge on these demons. He walked over to the demon dick, this one red and big. It was the perfect height, and he began grinding against it, his groin resting on the demon’s penis.

“Aha, now you demons are getting off from touching my dick!” Jack was proud of himself and was a bit too horny to realize he was also getting himself off from touching a demon’s dick. He was pent up, and the sensation of rubbing the silky panties between his dick and the monsters was so fucking good. He was getting close when the demon’s cock came, cum spilling onto Jack’s shirt.

“No, I am so close!” Jack shouted. He ground against the penis as it returned to the wall, but it didn’t slow down. Still, Jack wanted to cum so badly. He started to hump against the wall, light grunts as he sought a climax. Eventually, it came, and a surprisingly loud moan escaped Jack’s lips as he came into the panties. He enjoyed the sensation of relief, head focused on the feeling of the orgasm before coming back to reality.

“What did I just do.” Jack should have felt disappointed, but instead, he wanted not to stop masturbating, to get more pleasure. Were these more changes from the box? He changed clothes again, having found spandex-like bottoms and a crop top. Hopefully, the material would make it harder for cum to stick to it. Jack looked over the mirror and couldn’t help but touch the top of his head, feeling a sharp tip from the small black horns sticking up. His hair was now pink and still longer. He moved his tongue and realized his teeth were now all pointed. 

Jack began to weigh the options in his head. It appeared he had no way to escape by himself. That gave him two options. First, he could resist as much as possible, fight the demon, and refuse to touch any more demon’s cocks. It would likely end in his death or extreme pain as the demon tortured him repeatedly. Second, he could comply, meaning his body would probably continue changing. As he changed, it seemed he would experience a desire to please himself and the demons more and more. So which path did he choose?

Jack glanced one more time at the mirror before deciding. It was better not to experience pain; if his body were to change, he would at least enjoy himself. At this point, it was evident that something supernatural had occurred to him, and it was unlikely that anyone would save him. In that case, then, what was the point of resisting? He gave a slight grin and watched his mirrored version follow. Man, he was hot looking now. A new demon pushed its penis through, and Jack’s grin grew more expansive, and he began to approach, ready to experiment.

Jack began to experience all sorts of pleasure. Just as his hands didn’t seem to get sore, his dick seemed to have the same properties, and he was capable of orgasming repeatedly. His body seemed to sweat, though, and sweat drenched Jack as he began to try all sorts of positions. First, he tried rubbing his butt against one demon’s cock. It felt alright, but the demon must have enjoyed it because it came super-fast. His favorite position was probably the next one, where he put his butt on the wall above the cock and then used his thighs to clamp down on it while swinging his hips back and forth. The feeling of his balls rubbing against the hard dick below was so good that he came that time before the demon did.

Jack used this position a couple of times more before switching to laying his back and using his feet to massage the demon cocks while he used his hands to get himself off. It was a great position, except one had to be careful; otherwise, they would get cum in their face. Jack realized that after one demon got most of its load on his face.

“Eww, gross.” Jack paused after speaking.

“What happened to my voice,” he said slowly. His voice had gotten higher pitched.

“I sound like a girl now….” Yet Jack didn’t feel too anxious. He absentmindedly wiped the cum off his face, rubbing it onto his clothes while he thought. Was he a girl now? Jack didn’t feel like one, even though he had gotten off a whole bunch of demons and himself while doing so. Did that make him gay? Though he looked like a girl now, so did that still apply?

“Whatever. What I need is a shower.” No new demon cock appeared, granting his wish. Perhaps the demon in charge was listening. Jack peeled off his clothes, a mixture of body fluids soaking into them, and began to shower. This time he couldn’t help but touch himself as the water cascaded down. His nipples had started pushing out slightly, and they were pretty sensitive as Jack used one hand to grope at them while the other felt at his dick. A girly moan escaped his lips as he came.

Jack got a new set of gym clothes. His hair still was growing, and now was a reddish color. His tongue was growing longer, with it going down to his chin when Jack stuck it out. A new green demon penis appeared, and Jack approached it before hesitating. There was a position he hadn’t tried yet, something that would use one of his latest changes.

Jack approached the cock, and then slowly opened his mouth, licking the demonic penis. It didn’t taste that bad, especially considering it belonged to a demon. Jack began to lick more and more, his hands reaching down to feel his own cock. Jack was about to start taking the cock into his mouth when the demon came, cum splashing on Jack’s face and into his open mouth. An intense desire to swallow replaced any thoughts Jack had to spit it out. It might have been a side effect of the changes, but the demon’s cum tasted better than anything Jack had ever tasted.

He hungrily licked the cum off his face, using his hands to scoop what he couldn’t reach with his tongue, sucking cum off his fingers. When the next dick appeared, Jack pounced on it, not even hesitating as he stuck it deep down his throat. He choked and realized he couldn’t take something that deep yet and began to push the cock as deep as he could without gagging. He used one of his hands to massage the demon’s balls to get that tasty cum faster. It was successful; soon, fluids were filling Jack’s mouth. He moaned as the sweet flavor filled his mouth.

“I need more,” he said, voice filled with lust. Two demon dicks appeared, fulfilling his desires once again. Jack began to work both, taking turns sucking on one while he rubbed the other. Eventually, he worked one up enough to cum and shoved it into his mouth, sucking the dick dry. He then focused on the other while a new one emerged from the wall. Jack sucked on cocks for some time, switching back and forth between two penises. Despite his best efforts, he missed some orgasms, and soon cum was covering his body.

However, all good things eventually must end, and it seemed he had exhausted the supply of demon cocks. Once again, a lull appeared, and no new demons came to replace the previous.

“No, come back, demons!” Jack whined. He looked around, hoping the demons had emerged from somewhere but found nothing. He looked down, where his bulge stood out. He pulled off his pants and lay on the ground. He twisted his head forward, reaching for his cock. Luckily it seemed his tongue had grown out further. He used that length to caress his cock, tasting his penis. It was not long before he came, cum spilling onto his body, face, and into his mouth.

“Aww, it is not as tasty.” Jack was disappointed. He got up, deciding to change clothes into something more freeing. Jack found a bikini set that seemed to work well, though his penis and balls stook out a bit. He looked in the mirror, sticking out his tongue to see how long it had gotten. It was now at least six inches long. His hair was even longer, reaching down to his butt, and bright red. His horns had fully grown, black points twisting back.

While Jack waited for more demons to appear, his thoughts began to drift. Was he okay with changing into a monster? He assumed the changes had affected his mind, but he still felt like the same person. Sure, it had felt super good sucking cock, and the taste of cum gave him a feeling of ecstasy. But he could still name all his favorite movies and remembered what ice cream was. He should feel panicked that he was turning into a demon, but he didn’t. If the demon offered him a chance to leave at this point, would he take it? If he went back, how would he satisfy his urges? The pleasure he had felt before couldn’t compare to the sensations he was experiencing now.

While Jack pondered, a new demonic penis appeared, interrupting his thoughts. Jack decided to enjoy this one. He pushed his butt against it, only the thin bikini bottom separating his butt from direct contact. Jack moved his butt up and down while feeling his own body. He noticed when the changes began for once, as he could feel his butt expanding. It was also obvious he was forming claws, and he had to be careful not to scratch himself. And was it just him, or was his skin color changing, becoming redder?

Most important, though, was the expansion of his chest. Jack’s dick was rock hard as he massaged his expanding breasts. He moaned as he felt at his nipples, barely remembering to move his hips for the demon behind him. It was only when it finally came across his back did Jack remember what he was supposed to be doing. When the next demon dick arrived, it had enough length for Jack to enact the next position he had planned.

He got on his knees and then manipulated the penis under his bikini top, between his breasts. He began to lick at the top of the dick while he rubbed his breasts against it. Jack’s new position worked, and the demon came in record time, cumming into Jack’s awaiting mouth. Jack began to give all the monsters a boob job, enjoying the pleasure as his breasts expanded. It felt so good to feel the hard warm dicks rub against his chest. The movement also rubbed his nipples against his bikini top, generating more pleasure.

Still, Jack wanted more. And he had begun to ponder using his butt as the next source of pleasure. Surely, he would feel good from it, right? Still, he was worried that it would also hurt, especially considering how big the demon’s penises were. But imagine how much pleasure he could feel as well. Jack looked at the latest penis, one of the largest yet. It was black and had an equestrian shape. He had been licking at it, so it dripped with his spit, making it well lubricated.

“Well, might as well see how it feels,” Jack said, getting up and turning around. He pulled his bikini bottom to the side and slowly backed into the cock, guiding it to his anus. There was some pressure, so he pushed against the opposite wall to help push the cock further. He groaned a bit; there was some pain, as expected, but nothing too wrong. The more he pushed it in, the less pain he felt. The cock began to fill Jack with pleasure as he felt his body fill up with the demon’s cock.

He began moving back and forth on the cock, letting his anus push the cock out before leveraging the opposite wall with his hands to make it go back in. Jack picked up a rhythm and began to moan as the desire to feel more intense sensations took over his brain. Soon he was thrusting fast, his dick smacking against his belly. Jack was panting hard, tongue sticking out of his mouth as he focused on the beautiful feeling of the massive demon dick filling him.

“Oh fuck, I am cumming!” Jack shouted, his dick spurting cum. He pushed himself as far onto the dick as he could, squealing in pleasure as he did so. The sensation was too much for the demon, and massive loads of cum began to fill inside Jack. The dick started to remove into the wall, and Jack enjoyed a new feeling as cum slowly poured out of his butt. Jack realized he had grown something new and looked behind him to see a black tail had appeared. He experimented with it and realized he already had great control over it.

A new demon penis had emerged. This one was different, poking upwards from the ground, and was massive. Jack removed the bikini set; it would get in the way. He slowly lowered himself onto the dick. Soon Jack was bouncing up and down on it. He used his hands to feel at his breasts, his tail wrapping around his dick, jerking himself off. Jack was ecstatic until the demon disappointed him as it came inside him. Jack had just been getting started. Good thing there were plenty more demons for him to use.

Sometime later, Jack was working three demons at once, with two dicks on opposite sides of the narrow part of the wall. Jack spit roasted between them. The third was above, and Jack’s tail continuously teased it, the tip slowly stroking the demon’s cock. It was the first to give in, cum spraying onto Jack’s newly grown wings. The two other demons followed shortly after, and Jack came from the dual pleasure of being filled with cum on both ends.

As the cocks slid back into the wall, Jack stood up and gave himself a long look in the mirror. He was a demon now, with reddish skin, horns, wings, and a tail. Jack also wasn’t truly a man anymore, even though he still felt that way internally, with large breasts and a feminine face and voice. He squeezed his breasts, enjoying the soft squishy flesh; he never got tired of feeling those. Jack felt thankful for the demon capturing him. If he had known it would feel good, he never would have resisted in the first place.

“You have done well, my little pet; my army is in quite high spirits.” The demon in charge was speaking to him once again.

“Of course, master, please send more my way; I am still not satisfied,” Jack said, using his long tongue to lick at his breasts as his fondling continued. The demon laughed.

“Ha, you are a greedy one, aren’t you? Don’t worry, I have a reward for your services, which will give you true pleasure.”

Another rune appeared, and then another, and another, until the runes filled the room. However, instead of demon cocks appearing, red tendrils poured out instead. They began to move towards Jack, who stretched his arms out, welcoming them. He enjoyed the feeling as the slightly gooey tendrils wrapped around his arms and legs, constricting their movement. The tendrils pulled his arms backward, while a tendril wrapped around his neck, pulling his back forward. He felt a massive tendril enter his butt and gasped with pleasure. Another large tendril took that chance to enter his mouth, and Jack welcomed it.

The tendrils began to pump in and out of his body. The tendrils around his arms also pulled backward, yanking him deeper onto the tendril. Muffled moans came from Jack, saliva dripping down his chin. The tendril in his mouth pushed deep down his throat. He had to wait to breathe in bursts when the tendril pulled upwards. Jack glanced at the mirror and saw two distinctive bulges, one in his throat and the other in his stomach, as the tentacles fucked him. He also noticed that his feet had changed to hooves, and dark fur was growing in his shins.

Jack felt so good. It was so hot having the tentacles use him for something to forcefully fuck him. The tendrils continued in this position for some time before deciding to change it. The tendrils withdrew from his mouth and anus. A large amount of saliva involuntarily poured from Jack’s mouth, stringing between the tentacle and his mouth. His anus gaped, still wanting more. The tendrils let go of his neck while the ones holding his arms pulled his arms upwards. The ones holding his legs followed, twisting his legs upwards towards his head.

Jack was now hanging in the air by his arms and legs, back facing toward the ground. The large tendril returned, and Jack moaned as it re-entered his butt. Other tendrils began to feel at various parts of his body, some massaging his legs while others squeezed his breasts. Two small ones were playing with his nipples. It was too much for Jack, and he began to cum repeatedly. This orgasm set him off on a cycle, where he would cum, his body would convulse with pleasure, and the convulsions would rub his body against the tendrils more, causing him to cum again.

It did not take long before Jack’s mind broke from the pleasure. He wasn’t even thinking anymore, simply feeling joy repeatedly. His eyes had rolled back, and his tongue hung out of his mouth, spit dripping down. Cum slowly dribbled out of his penis onto his belly. The tendrils were merciless, though and continued to feel at his body. Jack shuddered with pleasure as a tendril began to wrap around his dick and balls, the tip of the tentacle teasing the end of his penis. Small girly moans were the only sounds he could make any more as he lost himself in the bliss.

Jack had lost track of time in his box a long time ago, so he did not know how long he experienced paradise. Eventually, the tentacles began to rescind, carefully dumping Jack on the ground. He didn’t even notice, his mind still blank. He lay on the ground, butt in the air while he drooled on the floor, cock still twitching. He didn’t even hear the demon’s voice as it spoke again.

“Well, it looks like you enjoyed my gift. Rest for a bit, my little succubus, for soon you will have plenty of work to do.”

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