I Took a 12-Inch Tentacle Dildo on Our First Date. A Year Later, We’re Still Going Strong.

Happy anniversary, and thanks for dealing with my bullshit!

Whenever I’m amidst a completely insane sexual encounter, I inevitably think to myself: How did I get here? How are two of the biggest bisexual porn stars in the world spit-roasting me? How am I being pegged by Pennywise? How am I getting my dick sucked by multiple queers in front of Diplo?  

This night, I couldn’t help but wonder: How has Raksha stuck a 12-inch tentacle dildo up my ass…and on our first date, no less?

Photo by Atlantic Melon.

The night was supposed to be “chill” (el-oh-el). Now I am not particularly known for being someone who is chill, but we were heading to a swanky apartment in the Village for a dinner party. Raksha’s friend was housesitting for a well-to-do couple, and we were going to roleplay as fancy, rich people. More specifically, I planned to drink all of their good Scotch. 

Well, I did exactly what I had set out to do, but then, something happened. See, when you roleplay being rich, powerful people—and drink a ton of nice Scotch—you begin to think you are a rich and powerful person. And when you are a rich and powerful person, you think you can do absolutely anything, like take one of Bad Dragon’s monstrous (pun intended) toys a foot inside of you without any preparation.

So by the time Raksha and I were in the Uber back to my place, we felt like gods—invincible horny gods. We quickly stripped naked, and Raksha began blowing me. I realized, Shit, I had way too much Scotch to get hard. 

Raksha knew. She is a mind reader. Or at least with me, she is a mind reader. We are always on the same page without having to say words.

Instead of trying to get me hard, which is just an uncomfortable experience for all parties involved, she told me to flip over. 

Okay, bitch! Now we’re talking, I thought to myself. Or who the fuck knows? I likely said that out loud. She then spread my wooly cheeks and delved in. Flat tongue on the hole, licking it like an ice cream cone. Then she poked her tongue in and out, getting up in there.

That was when I first realized Raksha was a gay man because no woman has ever—ever—eaten my ass like that.

And this gay man did not stop. She ate my ass for days—years. Meanwhile, my face was smushed against the carpet, and I was drooling everywhere. 

“Do you have any toys?” Raksha eventually asked. 

Do I have sex toys? DO I HAVE SEX TOYS? I don’t just have sex toys. I’ve lost so many sex toys inside of me that my body is thirty percent sex toys. I’ve lost so many sex toys inside of me that there is a special room at the Mount Sinai Emergency Department they leave vacant just for me. I don’t just have sex toys. I am a motherfucking sex toy. 

But this occasion didn’t call for any sex toy. Sure, I could have whipped out some of my favorite dildos or butt plugs—but this night required something special. It required something kinky because rich and powerful people don’t just have regular sex—they have weird fucked-up sex. 

So I whipped out my tentacle dildo. I had never used this dildo before. It was less for use and more of a statement piece that brought my living room together. (I moonlight as an interior designer.)

But tonight seemed like the night to whip out Octavius. 

Raksha started by first fingering my hole, warming me up for penetration, but I was impatient. I forcefully grabbed the lube bottle, drowned Octavius, and said go for it. 

The first couple of inches went in without a hitch, but as you can see, Octavius rapidly expands—getting girthy quickly.

I let out a deep breath. “I need poppers,” I said, shooting up. I ran to my bedroom; they weren’t there. I checked the fridge. Nothing. I checked under the bed. There are always poppers under the bed. They fall during sex, and you forget about them, but you can, in a moment of crisis, rely on finding them there. THERE WERE NO POPPERS UNDER THE BED. 

I began to panic. I needed that tentacle inside me. I had now made it my mission to take all of it. Besides, I am a sex professional and a black hole. I have to live up to the hype! What would my mother think if she knew I wasn't living by the words I preached? She’d be utterly disappointed! 

So I called up Jimmy. Jimmy works the night shift at the front desk, and he is bored out of his fucking mind. He’s also one of the kindest people on the planet. When I come home drunk and don’t want to go to bed, I head upstairs, grab a bottle of whiskey and some shot glasses, head back down, and we talk and drink until sunrise. That man is my therapist, in addition to my actual therapist, though he may be more helpful.

“Jimmy, it’s Zach,” I said.

“Hey, Zach! What’s going on?” 

“So I am about to take a huge tentacle dildo up my ass and don’t have any poppers. Do you mind running across the street and grabbing me some?” 

“Zach, you know I would, but it’s closed!”

“Wait, really?” 

“Yeah, it’s not a 24-hour bodega. I’m looking at it now across the street! Lights are off. It’s closed!’ 

“Shit,” I respond. 

“It’s okay, Zach. You go this. Take it slow, take deep breaths, and use a ton of lube. I have faith in you.”

Jimmy’s faith was more potent than an entire bottle of Jungle Juice. So when I got back on all fours, and Raksha inserted Octavius inside of me, I took him. Still, I was having trouble when he hit my back wall, where the rectum turns into the sigmoid colon. But because Octavius is so thin and malleable at the top, he eventually slithered his way in, and I…I took that entire fucking tentacle up my ass. I could feel him in my goddamn gut. And he felt good—rich and powerful person good. 

Raksha then took all of Octavius out and put him all the way back in. She kept at it, and each time he came out, I felt my body combust. Then she’d shove him back in, and I also felt my body combust. At every point, whether full or empty, my body was combusting. There was one final quick pull-out that triggered an orgasm, and I shot my load all over the carpet.

What was wild is that I didn’t even realize I was cumming while I was cumming. If I hadn’t seen myself shoot, I wouldn’t have known. It didn’t feel any different from the actual penetration because that was already so intense. 

I lay down on the carpet next to Raksha with her snuggled in my arm. I couldn’t formulate a word. I think I managed to say “Thank you,” which, honestly, I find to be a bizarre comment after one orgasms, but I said it anyway. We then zonked out. 

If one year ago, you had asked me if Raksha and I would become official partners after that night, I honestly don’t know what I would have said. I wasn’t thinking that far ahead. But here we are, one year later, in a meaningful and fulfilling relationship like that interspecies couple in My Octopus Teacher.  

Cheers to them. Cheers to us. Happy Anniversary, honey. I love you.