Chapter 1

I look down at the silicone tentacle I’m wearing on my right arm. I look absurd. It feels kind of like I’m a kid wearing a costume. The tentacle is a sort of fuchsia-purple color. Or maybe it’s magenta. There’s kind of a pink hue to it. Hell, I don’t understand color names.

The colors fall in a gradient pattern, with one side lighter than the other. That’s the side that has the little silicone suckers attached to it. The sucker-shaped parts are actual suction cups. It’s my second time wearing the prosthetic, and I feel just as awkward this time as I did the first. But Jessica loves it.

My girlfriend, Jessica, has a huge hentai fetish. It’s the only porn she’ll watch, and she loves to watch it with me. At first it was cool. Who doesn’t want a girlfriend that wants to watch porn with them? Then I found out that tentacle-porn is literally the only thing she watches. She has no interest in anything else, and when I bring up watching something different, she tells me I can watch it by myself. I guess it’s better than her telling me not to watch it.

Still, I’ve never fully understood the hentai fetish, and now that I’m sitting here with the tentacle on my arm, it feels unnatural. Jessica looks excited, though. She spent a lot of money on this tentacle, and I don’t want to disappoint her. She lies on the bed wearing only a loose t-shirt. No panties. No socks. My eyes drift down to her toes, digging into the sheets like a kitten kneading them. It’s cute.

Of course I want to do what makes her feel good. Even if it feels a little silly. I start to touch her thigh with the prosthetic tentacle, the way she likes it. Jessica closes her eyes, but when I lift the tentacle and press it against her skin again, her eyes pop back open.

“The lube,” she says.

Right. I forgot. What’s a silicone tentacle without a bit of mucus-substitute? I lean over, reaching with my non-tentacled arm and straining not to fall over as I grab the bottle of lubricant off the dresser. Then I pop open the bottle with my thumb and generously pour it over the length of the tentacle. Jessica likes it real wet. I say nothing, as she has instructed me.

After I set the bottle back down, I plop the tentacle down on her thigh. It makes a wet smack sound, and Jessica moans. Now that they’re wet, the suckers stick to her skin easily, and as I peel up the silicone tentacle, each of the suckers pops off her skin like moist, smacking lips. I peel them up from the wide end of the tentacle first, starting at my elbow and finishing by removing the suckers at the tip. I have to use my left hand to help with those a little bit. I nervously look at Jessica as I do this. She doesn’t like feeling my hand while she’s in this headspace. Fortunately, her eyes are closed in anticipation, and she’s pulling her t-shirt up higher to get it out of the way. She doesn’t take it all the way off, though, and her tits are still covered by the light, clinging fabric.

After peeling up the suckers, I smack the tentacle against her again, slightly higher on her thigh. This time, the suckers at the tip attach across her hip bone and over her lower belly. I slowly peel them off again, and Jessica squirms in the bed and moans. Her leg and lower abdomen are covered in the lube, and I watch as she lowers her hand to rub around in it. I guess that’s part of the experience.

Okay, she looks ready. I take a breath and aim the tip of the tentacle between her legs. I have to be careful not to touch her with any other part of my body. It ruins the illusion for her. I made that mistake last time. I hold my tentacle arm steady with my left hand and navigate it toward her. The tip of the tentacle is longer than where my fingers end, so I don’t have a lot of control over how it moves, and the silicone is somewhat flexible, so it can wiggle around a bit.

As I reach the tentacle towards her, the end of it flails around, lightly touching her inner thighs and labia, leaving a trail of shiny lubricant. Jessica sucks in a breath at the feeling. I look up and see that she’s biting her lip. Then I look back down and bite my own lip in concentration, trying to hold my wrist steady as I aim the tentacle at the slightly parted opening of her labia. It wriggles its way between them, sliding between her pussy lips and bunching up as it presses against her, not quite finding the opening of her vagina. I press my lips together and push forward, getting the wriggly tentacle to penetrate her though brute force.

Jessica moans loudly as the tentacle pops inside her. She doesn’t seem to mind the lack of finesse. If anything, her moan sounds over the top, but she’s certainly not doing this for me, so I guess the sensation really does feel that good.

Now that the tip is inside her, my role is easier. I lean down on the bed, holding myself up with my non-tentacled hand, and I slide the octopus arm deeper inside Jessica. She opens her legs wider for me—well, for it—and I begin pumping the narrow end of the tentacle in and out of her. I admit, it looks good. I still don’t dig the tentacle thing, but watching anything sliding in and out of Jessica’s pussy turns me on. I feel my dick finally waking up.