Chapter 4

I’m pretty sure my mouth hangs open for a moment as I stare at the tentacle, now buttoned to my girlfriend’s ass hole by a lone suction cup. I feel laughter welling up inside me, but I stuff it back down. I absolutely cannot laugh at this right now. Jessica’s butt hole keeps contracting and loosening, feeling at the unusual shape that has invaded it.

I think quick. The sucker is pretty close to the tip of the tentacle. I press more on the tentacle behind the sucker. Jessica groans a bit. I’m not sure if it’s a happy sound or not. Everything is so slippery, the tentacle is just wiggling around against her butt. I press harder, with two fingers, and the tip bends in half just above the suction cup. The bent over part starts to open her dark little portal. Yes! Success.

I let off a little bit, not wanting to ram too much tentacle into her ass at once. It’s a lot smaller looking than the opening to her vagina. I start pressing and releasing the tentacle, letting the bend above the sucker enter her just a little bit, getting her hole lubricated with the slippery liquid on the tentacle.

Jessica starts moaning. A lot. She seems to really like this. I pick up a rhythmic pace, pumping the tiniest length of bent tentacle into her ass hole. It’s really turning me on, and I start to increase the pace, plunging the bit of silicone into her opening faster. And then it happens. I’m paying more attention to the sight of her little sea star sucking on tentacle than I am to how vigorous I’m thrusting, and on the next thrust, the bent-over bit of tentacle plunges deeper into her, allowing the narrow tip to slide inside with it. The tentacle has actually entered her ass now. I stop thrusting, afraid that it will pop back out. I think this is what she wanted—actually having the tentacle inside her—and I don’t want to screw it up.

Instead of pulling back for another thrust, I grab the tentacle behind her and move it in a circular motion, massaging it around inside her butt hole. My dick throbs. Shhh.

Only the tiniest bit of the tentacle is inside her. I press my hand forward inside the prosthetic, trying to create more pressure and taking up the slack in the curvy silicone. Keeping my fingers just behind her opening as guides to keep the narrow end of the tentacle in place, I start thrusting forward only, in small movements. The lubricant does its job, and the tentacle slithers deeper inside Jessica.

She lets out a big, sighing moan and says, “Yesssss.”

Once the tip is in, the tentacle actually enters her fairly easy. Once it’s in a few inches, I feel safe to start thrusting again, fucking her with my tentacle, confident that it won’t pop out. I start slow, but as soon as I see how into it she is, I fuck her faster. The suction cups really do seem to be a nuisance, catching on the tight opening of her ass when I thrust in and out of her, but she doesn’t seem to mind, so I don’t. I’m mesmerized by the sight of it. The suckers thrum against her ass hole, catching small pools of lubricant and spilling it down her skin so that the area around the little sea star shines in the candle light.

To my surprise, the hard fucking isn’t deterred by her tiny-looking hole. In fact, as I fuck her harder, the tentacle sinks deeper and deeper inside of Jessica. Her ass offers me no resistance at all. Maybe she’s done this before?

The thought of how deep the tentacle can go inside her really turns me on. The caress of the currents is driving my dick into a frenzy, teasing it with no hope of real stimulation. I want to see how far this tentacle goes inside of Jessica. As I thrust, I start to move it forward, giving more to the in-thrust than the pullback. My fingertips and then my hand inside the prosthetic are now inside Jessica’s ass. I stare in awe at how widely stretched her opening is. This is about as far as the tentacle has ever been in her vagina, and yet she has not complained that her ass is stretched too far. I press on, fucking her up to my wrist, wondering what the other end of that tentacle is doing inside of her. What does it feel like?