**18+ Content Below**
For context, my party was exploring a cave and spotted a mindflayer working in a side cavern. Cue me attempting to seduce the mindflayer to add a conquest to my character’s bingo card! One successful roll later…
The hardest thing about fucking monsters is keeping your wits about you. Particularly when facing down a creature as awe-inspiring as this mind flayer.
They were a few inches taller than me, their skin a shiney mauve, and dressed in long dark robes obscuring their body. Their four facial tentacles shift thoughtfully, stroking one another, as a dwarven man might stroke his beard.
I suppose, for science, intercourse could be, their voice feels like honey in my brain, viscous and sticky, enlightening.
A shiver runs down my spine and I feel the blood rushing from my brain, directly to my cock. My mind is blank except for an overwhelming need to have those tentacles touch me, wrap around my cock, slip inside my ass. I feel myself growing hard just at the possibilities, the novelty.
Vaguely, I am aware of quiet scuffles. My fellow travelers were moving back into the previous cave, away from the monsters. Oh well, one man’s adventure is another’s perversion.
Or, I could just kill you, now that you’ve been abandoned by your friends, they flow through my mind. Your death would be excruciatingly painful. The viscous pull of their words helps me regain my wits and shove the question of how many tentacles could I suck at once to the back of my mind.
“Most of my life has been excruciatingly painful,” I say aloud, the right side of my mouth lifting into a smirk. “I wouldn’t expect my death to be anything less. That’s why I worship pleasures. Pleasure is what makes the rest of life worth it.”
Worship pleasure? they scoff. Knowledge is the ultimate power and yet, I do not worship it. I keep it and control it, wield it in ways your insignificant mind cannot understand.
“Yes,” I agree easily, loosening the ties of my shirt. “And now you have a chance to know how to pleasure someone. Or you have the chance to have a meal, an experience I’m sure you’ve had many times over. One you already know.” I pause, pulling my shirt off in an easy motion.
“Care to learn something new?”
White pupiless eyes slowly blink at me. I step forward slowly, unlacing my pants. I leave them precariously perched on my hips for the moment and reach out to caress the side of their face, trailing my fingers down one tentacle. Their skin is slick with their personal oils and firm with muscle underneath the odd rubbery texture. I reach the end of the tentacle and it curls around my hand, exploring my skin in return.
I shift forward to reach for their shoulders and their tentacles swiftly move to grab at my face, one wrapping around my neck while two others explore my stubbled cheeks. The fourth tentacle ruffles through my hair. I have no doubt that my life is literally being held in the balance and my cock throbs painfully at the thrill of it.
You are afraid and yet you enjoy it? They seem confused but I hum my agreement with their assessment. No words slither through my consciousness but I’m struck with a sensation of puzzlement and hesitant curiosity. Their feelings, not mine. There is nothing hesitant about the hardness of my cock, straining to be free.
I turn my head and catch the tentacle exploring my cheek with my mouth, kissing and then licking the prehensile tip. They taste of garlic and vanilla. Odd but not overwhelming. They gently squeeze my tongue and I start to suck, hollowing out my cheeks. A jolt of apprehension shudders through me from their mind along with the image of the similar suction they use to pull a brain into their mouths. I relax my jaw and think very firmly about the blow job I gave to a dwarf guard back at Safe Harbor, about how he’d come with a gruff cry and grinned down at me through his beard. The mind flayer gets the picture. His pupiless eyes give a slow blink and he allows me to continue sucking at his tentacle.
I open his robes, slowly moving them down his shoulders while maintaining eye contact. When they are in a puddle at his feet, I shove at my pants, allowing my hard cock to bob up against my stomach. Lightly gripping a tentacle in each hand, I take a step back towards the lab table, pulling them with me away from our clothes.
I would like to try what you did with the dwarf, they demand, pulling the tentacle from my mouth, gripping my wrists with the tentacles I’d been using to guide us to the table, and wrapping the fourth tentacle securely around my neck. I sighed in pleasure at being so confined and smiled at the creature.
“Okay, big guy. Giving or receiving?” This close, I could see the gaping mouth normally hidden by the tentacles. Rings of wicked teeth lining the surface. Goddess help me if they wanted to try blowing me. I could probably heal myself enough to compensate for the damage long enough to get off. Probably. My cock throbbed at the promise of commingled pleasure and pain. The Sacred Sting would not fail me and leave me so maimed as I could not worship her. I knew that with a certainty I felt in my bones. That did not mean it wouldn’t be a challenge.
The mind flayer uses his grip on my wrists and neck to turn us so he can lean back against the lab table, ignoring the partially vivisected frogman on the table’s surface, and starts pushing me to my knees. Giving it is.
As I kneel, my hands are pulled above my head, still wrapped in tentacles, but the one around my neck loosens when I don’t fight back against this idea. I don’t think they would take kindly to brat behavior.
Their cock is a shorter, darker tentacle with a more bulbous head framed with delicate frills that remind me of a merman I’d spent a night with. Their cock is flexible, more pliant than mine is currently. I start by licking the head and nibble gently on the frills, gauging their reaction. Their chest starts rising more quickly and their eyes close when I swallow down their length. The tentacles around my wrists loosen as I bob my head up and down, creating gentle vibrations by humming. The moisture that coats the rest of their skin is more plentiful here and the taste of garlic is stronger, overwhelming the vanilla notes.
When my hands are free, I begin exploring with my fingers, using one hand to wrap the base of their cock and reaching underneath with the other hand. A slick warm slit greets me instead of balls. I slip one finger inside, cautious of any possible rings of teeth, but only feel a wet canal of elastic muscle that shivers around my intrusion.
I lose myself in the act of worshiping this creature and the pleasure I’m creating for them. Alternating my hands and mouth between their cock and pussy until their breathing grows harsh and I feel their climax swelling. Pleasure floods my mind through our connection until the walls of their inner channel start spasming around my fingers and the mind connection goes blank.
Slowly, I stand and begin to shift their body so that they are at the right angle against the table. They are quivering and do not seem fully aware of my actions until the blunt head of my cock presses against their pussy. I push in, hooking a foot onto the stool for a better angle, and they clench their inner walls around my length.
You are much firmer than I am when I procreate. I take it as a compliment as I start thrusting.
“If you’re flexible enough, you could take me as well,” I say, picturing how the merman filled my ass.
The bulbous tentacle head immediately wraps around, past my balls, searching for the tight ring of muscle. Their natural lubrication allows them to push in, the pressure of being filled making me groan aloud. It’s the dual action of a threesome without a third partner. And this mental communication is very handy.
We find our rhythm. I’m soon pounding into him as he thrust into me and, dear Goddess, it feels amazing! The sounds of our bodies coming together echo through the cavern. The table we’re using is sturdy enough but the constant thrusting sends tremors through its surface, shifting the dead frog man until the body flops onto the stone floor.
Tentacles fill my mouth, stroke my hair, my neck, my back. Lovers should always have additional appendages, I decide.
Their breathing becomes ragged and their hips start to stutter so I know they are close to the edge. I suck hard on a tentacle and thrust deeper into their pussing in a coordinated effort and am rewarded by a flood of warmth filling me as they spill their seed in my ass. Receiving aftershocks of pleasure through our connection, I allow myself to finally come, filling them as well. They slump against me, tentacles still for the first time since I entered the room. I hold them for a few moments before slipping free.
I’m thoroughly coated in their skin’s moisture and I’m sure everything will taste of garlic and vanilla for the next week, but a heavy feeling of complete relaxation and pleasure drowns my mind through the link.
As I start to clean up, using a few items I find in the lab, they speak once more. That was indeed enlightening.
I give them a smirk, “Pleasure always is.” May the Goddess be pleased with my preaching.
DnD Sex Edition 