October

I can't sleep. According to my clock, it's almost midnight. Almost October, that wonderful time of year when basic bitches indulge in their pumpkin spice lattes, and advanced bitches like me indulge in entirely different spicy pumpkin activities. The whole thing started as a joke, acting out the memes about trans girls fucking pumpkins, making my cute little pet watch me do it while her cute little cock is locked up in her cute little chastity cage. It was my girlfriend's idea to make her hold the pumpkin, so it's really her fault, because I didn't realize how hot it would be until I'd tried it. Something about my pet kneeling on the floor, looking up at me with that pathetic, needy expression on her face, her arms trembling as she worked my hyperclit with that big orange gourd until I'd filled it with my cum, it was like a switch flipped in my head. And then draining it into her mouth after, making sure she drank every last drop of me...

My hand drifts between my legs, finding my clit. I trace my fingers along the hardening shaft.

I did it again the next year, of course. I managed to grow a pumpkin with a little dick sticking out of it, just as tiny and cute as my pet's, and I was going to end Locktober by frotting her with it. But my girlfriend had another idea, to bring in one of my other subs, the cute t-boy, and it was even hotter watching him pounding that pumpkin while she held it. By the time they'd both finished, my clit was leaking like a faucet, which just gave the two of them plenty to lick up while they took turns sucking me off.

My fingers are making tight little circles around that wonderful sensitive spot on the underside of my clit, just below the head. Remembering the last couple years lit a fire in me and I need to cum now. I start thinking of my plans for this year. I'm gonna have my girlfriend join in, get my pet to service both of us with a pumpkin. If she does a good enough job, I might even let my pet fuck it too. I imagine the subby bottom, topping a pumpkin that my girlfriend and I have already filled up, and it's just too much. I clench my teeth and groan loudly, my hips jerking in short little thrusts as my orgasm crashes through me and I paint my hand in cum.

I sigh and start to clean myself up. Maybe now I'll be able to get some sleep...

My eyes snap open as a touch on my ankle wakes me. Something smooth and firm is wrapping around one-- no, both of my legs, pulling them apart. I try to roll off my belly, but whatever's holding me isn't having it. I crane my neck to look back over my shoulder, and in the pale moonlight I could swear I see vines. The bed shifts as something moves between my spread legs. I can make out a round silhouette, but whoever it is, they're not saying a word. I flail for the lamp on my bedside table, slapping the switch and flooding the room with light.

Those are vines around my legs, bright green with sparse leaves, and on the bed between them is a massive pumpkin, big and round and orange, looking like a picture perfect stereotype of the traditional autumn gourd, with the exception that there's a phallic bulge pointing directly at me.

Sure. Pumpkin with a penis. Why not?

It's sliding across the bed, getting closer, and as that cock-shaped protrusion starts to press against my asshole, I stop caring how, or why, or that I'm not a bottom, I'm still too worked up from earlier. It enters me roughly, my hole stretching painfully to accommodate that fat orange cock, and my head crashes back down, the pillow muffling a long moan. It slides all the way into me, pauses for a moment, then pulls back and starts to fuck my ass, settling into a steady rhythm. Each thrust presses exquisitely against my prostate, again and again, and it isn't long before I'm crying out as I start to c--

It suddenly stops. I groan in frustration, trying to buck my ass back into it, but it's useless, those vines are still pinning my legs in place. An eternity later, it resumes its movements, slowly this time, gradually picking up speed. I'm climbing toward my peak again, my clit drooling into my bedsheets, closer, closer, almost there, but then the pumpkin slows down again, pulling back before I can find release. I'm trembling, panting, needy, but it can somehow sense the line and refuses to let me cross it. It speeds up once I'm no longer in danger of cumming, slows down when I get close, bringing me to the edge again and again. Each time, the pause to let me cool down is shorter, my climax closer, and before long it's pounding me at a leisurely pace that keeps me right on the edge continuously.

I feel another vine sliding up my back, along my neck, and suddenly my ponytail is being yanked back. The thrusts slow down, anticipating just how much it turns me on to have my hair pulled, and the vine hauls my head up, further and further, my neck and back bending painfully until I'm staring at the ceiling. It hurts so good that the pumpkin has gone completely still inside me. The vine pulls harder, hard nipples dragging deliciously across the sheet as my chest lifts off the bed, then my hips, and finally I can feel my clit standing out proudly, bobbing with every tremor of my body. I'm on fire, so desperately close, wishing this thing would just let me come already. The cock in my ass starts to swell, growing even thicker and longer somehow, stretching me open even further. There's no way I can hold back now, and as I pass the point of no return it starts pounding into me, hard and fast. I scream as my body spasms, cum erupting from my clit again and again. My ass clamps down hard, but the turgid shaft invading me doesn't slow down, furiously fucking me through a second orgasm l, even more cum gushing onto my bed. Distantly, I'm aware that the cock is still getting bigger inside me, each thrust stretching me a little wider, and before the last echoes of my climax finish rolling through me, I'm cumming again.

I've never taken anything this big, but it's still sliding in and out easily, picking up speed, and I'm no longer able to tell if I'm having several orgasms, or one long one that's stretching out for what feels like an hour. Suddenly the pumpkin surges forward, roughly burying its cock deep in my abused ass, and I feel something shoot into me, not a liquid, but thick and semi-solid, bursting out in fits and starts, like it's all part of one connected mass, with the occasional firmer nub rubbing against my most sensitive spots. My belly is starting to bulge slightly, but it's still going. Just as I feel like I'm about to burst open, the torrent slows to a stop and the pumpkin's cock starts to finally withdraw. As it pops free, I feel something stringy flopping out, a tapered seed dangling from it, and I realize what it's shot inside me.

Before I can think too hard about that, there's pressure against my ass again, something round and wide preventing any more from coming out of my gaping hole, pressing firmly and insistently. I crane my neck around to look behind me, my scalp burning as I tug against the vine holding me, and I see a pumpkin, much smaller than the one that's been fucking me, but still way too big to fit into the hole it's being forced into. I watch in horror as my ass somehow stretches to accommodate it, the pain too intense to enjoy, and I scream as it suddenly pops inside me, my hole closing around it, still stretched wide open but now plugged tight, the curved surface of the gourd clearly visible, a short green stem sticking out of me like a tail.

The vines suddenly release me. I fall forward, my face slapping wetly into a pillow that's absolutely drenched in my cum. The sudden weight on my distended belly is excruciating, and my vision blurs as I pass out.

I jolt awake with a start, running my hands over my belly, finding nothing out of the ordinary. My bedsheets and pillow don't feel wet at all. It must have been a dream. I relax, thinking of all the ideas that it inspired me to try on my pet this month, and as my eyes close, I see the tip of a leafy green vine slipping out of my open window.