Chapter Text
It all started when Jensen went to the third annual Halloween party held at the old house in the woods. The family had lots of money, a huge house surrounded by creepy woods, and had thrown the best parties according to his friend that invited him.
The theme this year was Gender Bend.
That is how Jensen ended up at a party in the woods wearing a short skirt, high heels, a belly shirt, and heavy eye makeup. To complete the look, he had donned a pair of lacy black panties with pink ruffles, a matching bra, and garters with stockings. In his defense, all of his buddies were wearing similar, and in some cases, more extreme versions of the same outfit.
The dare was, run out into the woods and bring back a brick from the old abandoned well that was a ways into the trees. It was rumored to be haunted and therefore a popular choice for truth or day games.
So Jensen, slightly intoxicated, had run out into the woods. No one had followed from the house to make sure he did it, which was weird. But Jensen was determined to follow through.
The woods were dark and a chill was settling over the night air. It was past midnight, and the sounds of the forest were loud and unknown as the nocturnal creatures made their way out of hiding to find mates and feed. The thrumming of the music from the house was barely audible as he went deeper and deeper into the woods. He felt his buzz receding as he realized he wasn't quite sure where he was anymore, having lost his bearings as the drunk are prone to do. The sounds of nature suddenly seemed to die off, leaving him alone in the silence that was broken only by the beating of the bass.
Jensen turned, a cold feeling that had nothing to do with the temperature seeping into his skin. But right there was the old well, bricks crumbling and the hole yawning deep into the earth. Jensen sighed in relief. At least he knew where he was now. He approached the well with and reached out to take a brick. It broke off easily, sending a few small bits to fall down into the well. Jensen didn't hear them hit the bottom.
He turned to leave, brick clutched tightly in his hand. He didn't see the inky blackness bubbling up and over the sides of the well, and he didn't hear the tendrils snaking over the ground towards him.
But he felt them.
A tendril snaked around his ankle, climbing up to his knee before Jensen had even realized what was happening.
"The fuck..?" Jensen tried to shake of the tentacle. It was slender but gripped him with surprising force. Jensen started backing away, finally noticing the thickening ropes coming out of the well, seemingly with no end. They were black, but seemed to be glowing slightly, enough to be distinct amid the darkness of night. Jensen stumbled back, tripping in his heels. He fell hard onto his back, and the tentacles took their chance. The swarmed him all at once, grasping his wrists and his ankles, wrapping around his arms and legs and torso, completely immobilizing him. Jensen stayed perfectly still.
This couldn't be happening.
One wrapped around his mouth like duct tape, silencing any cries for help. The one that had originally twined around his ankle now made its way leisurely up the side of Jensen's leg, pausing once in a while to rub against the skin. It reached the hem of his skirt and played with it briefly, lifting it up and pushing it out of the way. Jensen shuddered as it rubbed at the length of his cock through the thin fabric, toying with the pink ruffles that adorned them.
Now Jensen was struggling. He had watch enough cartoon porn to know what was happening to him right now. He didn't know how it was possible or why it was happening to him, but there was no way he was going let this happen to him.
The tentacles had other ideas though. They lifted him gently off the ground, still immobilized. The tentacle investigating his panties was joined by another which pushed them to the side, freeing his half-hard cock. In Jensen's defense, the fabric of the panties had something to do with it as well as the tentacles' rubbing.
Suddenly, his skirt was forcibly ripped from his body, split and discarded somewhere out of sight. His shirt suffered the same fate, fluttering to the ground five feet below. Jensen struggled harder, left in only his lingerie, which was being thoroughly investigated by several tentacles. Two were under the bra, massaging and sucking on his nipples, bringing them to peak hardness while another toyed with the fastenings holding up his stockings. The tentacle in his groin resumed its exploration of his cock, trailing lower and lower towards his hole.
These were all the least of his concern however. The tentacle that had been acting as a gag receded and formed itself into a much more phallic shape. It tapped against Jensen's clenched lips, seeking entrance. Jensen shook his head furiously, keeping his lips shut. Seemingly annoyed by his response, the tentacle that had been moving towards his ass brushed lightly against his hole, smearing something cold and tingly against the sensitive spot. Lube. Jensen gasped involuntarily, allowing the tentacle at his mouth to thrust in all the way to the back of his throat in one movement.
Jensen choked and made a retching sound as the gelatinous substance filled every crevice of his mouth. It tasted like unflavored jello and was surprisingly warm. A sweet substance trickled down the back of his throat, causing Jensen to cough around the tentacle. He tried to cough it up, but there was nowhere for it to go and more of the stuff continued to pour down his throat. Jensen felt a warmth in the pit of his stomach as if he had just drank a strong liquor. It spread up his throat and out towards his extremities, one in particular. His cock, only half-hard until now, was suddenly painfully hard as if he had just taken a shitload of Viagra. So it was an aphrodisiac, Jensen realized with dread. He was horrified and repulsed even as he arched upwards to the tentacles sucking on his nipples, overcome by sensation.
Moans escaped around the thick tentacle in his mouth, which it seemed to like because it began pulsing, retracting and then pushing in again to his mouth. Jensen fought the urge to let his head fall back and allow the tentacle deeper.
He felt a pressure on his hole, one thin tentacle pushing gently at the ring of muscle. Jensen clenched. He was half naked and had a tentacle in his mouth but there was no way he was allowing this to happen. The tentacle seemed to have different ideas, pushing in anyways. It must have secreted more lube because Jensen felt cold liquid being pumped into him as the tentacle made its way into him. It dripped out of him when the tentacle starting pumping in and out, the burning pain receding and being replaced by an exquisite sensitivity. Jensen's nerve endings felt like they were on fire, even as his brain short-circuited on fear.
The tentacle in his mouth slipped further into his mouth and down his throat, increasing its pace until it was brutally fucking his throat and cutting off his air with every other thrust. Tears formed in Jensen's eyes, running down his face and smearing his makeup. His bra was ripped off, stinging the skin with the force at which it was removed. The tentacles sucking his nipples smeared pre-cum over the sensitive skin, reddened and puckered from their administrations.
Another tentacle joined the one fucking his ass, larger than the first, about the size of two fingers. Jensen felt himself push back on it with shame, his body's arousal overcoming his mind's revulsion. The two tentacles thrust in tandem, both moving together at the same pace. Jensen felt his legs lifted up and separated, his knees pushed back until they almost touched his ears. He groaned in pain as his muscles protested the stretching pain. He didn't bend like this! His was going to be injured!
His panicked thoughts were interrupted when both tentacles in his ass suddenly pulled out, splashing their release all over him. Jensen shuddered, sticky and shaking with his own arousal. His mind was too far gone with the need to cum as more of the sweet fluid poured down his throat and into his stomach. Jensen eagerly sucked on the tentacle, whining when the tentacle receded. Jensen didn't care anymore, he just needed to come. The sensations were overwhelming, his nipples still being played with, and his hole open and gaping with cum dripping off his body. Jensen was vaguely aware of being pulled towards the well when a new tentacle, thick and blue and pulsing with light slithered its way out of the well and towards him. It was huge, the thickness of his arm at least, and Jensen felt a thrill of gross excitement run straight to his cock.
When this tentacle breached him, it hurt.
A lot.
But more lube was pumped into him, and the pain retracted. This tentacle was different. It vibrated inside Jensen as it pushed inside, not thrusting but instead pushing in and in and in, tapering and thinning as it went further inside. Suddenly, his situation seemed far less unappealing, as if his mind was being made up for him. His skin felt like a thousand tiny sparks were dancing over it. Jensen moaned and bucked his hips, searching for release, begging around the tentacle in his mouth for whatever this monster was to just fuck him, go deeper inside. To let him come. He hoped no one found him like this, stuffed with a glowing tentacle, moaning and bucking like a cheap whore. Another tentacle pushed itself inside Jensen's mouth, stretching his lips around both as they fucked his mouth. Jensen tipped his head back to allow them better access, and tried to pull his legs back further in an invitation even as self-loathing bubbled in the recesses of his mind. A thin tentacle took him up on the offer, poking at his stretched rim and working its way inside until it found his prostate. It started suckingon it, and Jensen screamed as his vision went white and his legs went numb. He vaguely felt the tentacle in his mouth pull out and spill hot cum all over his mouth, face, and stomach.
When Jensen woke, he was lying on the cold ground in complete darkness. He was sticky with his own release and that of the monster that had violated him, his muscles sore and lethargic. He didn't want to move. It was silent save for the dripping of water. He was underground. He wondered what time it was, if anyone was looking for him after he didn't come back from his dare. He was wearing only his panties, the rest of his clothes lost. It didn't particularly matter
And there was still a tentacle in his mouth, so deep down his throat he swore he could feel it in his stomach. The weird thing was, he didn't feel suffocated like he should. He had the strangest feeling of belonging, like he was where he was supposed to be, like he was supposed to spend eternity as a fucktoy with a tentacle down his mouth. Part of him felt horrified at the thought of "belonging" with a tentacle down his throat in a cave. But the rest of him had accepted it.
In the darkness, he saw a light coming towards him, a blue light.