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Fuck. I needed to get my head in the game. Thinking about Henry during a live stream only worked if I was feeling amorous. When I was angst-ridden and indecisive, my dick would not stay hard.

Back to business.

“Okay, everyone! What number am I thinking of? Choose between zero and fifty, and the closest guess wins.”

I eyed the chat as a slew of numbers came in. Once the messages started to die down—and after a downright theatrical pause for effect—I announced the winner, xxx_dtf_xxx. “My number was thirty-four, which triple x DTF triple x guessed exactly! So because you won, DTF, you get to choose not only what I use and how but also for how long.”

Emojis and friendly ribbing exploded in the chat, and I smiled. I loved the community here, unconventional though it might be. Everyone was generally nice and congratulatory until we got down to business, and then the tone turned more . . . well, I guess amorous worked. Horny was probably most appropriate.

DTF had responded, and I widened my eyes as I read the message aloud. Dramatic effect and all that. “Whoa, guys! DTF’s coming in with the great ideas today. Looks like I’m fucking myself with the dildo for a full two minutes.”

A flurry flew through the chat, and I chuckled.

“Okay, let’s get started! This is gonna be a fun one.”

Since I’d already prepped myself before the live, I simply reached for the lube, drenched one of my thickest and best-suited dildos—smaller than Behemoth but not by a lot—then suctioned it to the hardwood floor. Hooking my fingers into my waistband, I slid my joggers off slowly, teasing the reveal of my dick before turning around to bend over as I peeled them off, flashing my perfect ass—and likely my hole—at the camera. After a quick turn and slow jerk of my cock to get the viewers salivating, I turned back around so the camera would have the perfect view of my hole, spread my cheeks wide to get that glory shot, lined myself up with the dildo, and worked it inside.

“Fuck,” I cursed as I struggled to fit the head in, breathing out to help me relax. Maybe I’d been a little overambitious taking a cock as large as this one without more prep, but I wanted that stretch, that burn.

Truth be told, I wanted to be reminded of Henry’s dick.

“Shit!” I screamed as the head popped past my rim, then I spread my cheeks wider, almost to the point of pain, as I sunk down on the silicone dildo. Within seconds, it was buried to the hilt.

Since I was not new at this, I’d placed my phone on the bed in front of me so I could monitor the chat as I fucked myself on this massive dick.

“Okay, guys, who’s gonna track my time?”

DTF jumped in right away, volunteering.

“Okay, DTF, that’s fair. Ready?”

An affirmative emoji later, I raised up on the length until only the tip was inside then sunk back down in a whoosh, letting the cock pound my prostate. My eyes rolled back in my head as I lifted then slammed back down again, bypassing any buildup. I needed this thing to split me in two.

I got into a fast rhythm, working up the audience as my breath grew shorter, my cries grew louder, and my ass stretched almost as much as when Henry’s massive cock had wrecked me.

But only almost. Nothing compared to his dick filling me oh so well, so completely until I couldn’t breathe, couldn’t think, couldn’t exist without craving more of him. This paled in comparison, but just thinking of Henry this way was getting me all worked up, and I thought I might be able to come hands free just from this.

“DTF,” I cried out between gasps, “time?”

Twenty seconds came the reply, and I shouted.

“Fuck, I’m gonna come!”

I didn’t have time to turn around and face the camera, so my viewers would miss the glory shot, but I could give them the next best thing—me shooting a load of cum on the floor with that dildo stretching my red, puffy asshole in the foreground. Thanks to quick thinking I chocked up to a plethora of experience, I aimed my cock at the floor with just one finger at the base so I didn’t stimulate the velvet length. I didn’t need it.

I screamed as I came, barely having to exaggerate for the viewers. I hadn’t really planned to come so soon, but I knew from experience that I could draw this out and go again before too long. Hopefully most of my viewers would stick around to see if I could come a second time.

I would, of course.

Once I got my bearings, I lifted gingerly off the dildo, flipped around, and sat on the floor as I looked straight into the camera. “Whew, thanks for a fun time, DTF! That was a good one.” I winked, watching as the chat filled with tips and congratulatory comments. It wouldn’t be my best haul, but I sensed I would bring in a respectable amount.

When the chat started to die down, I jumped in with my next game, selecting the winner, who wanted me to wear the nipple clamps as I jacked myself with the cock sleeve. I was only half hard thanks to the recent orgasm, but I’d committed to this, so overstimulation was on the docket today.

I winced as I got to work, first pinching my nipples until they were large enough to hold the clamps. Once those were on, the tight buds growing more sensitive with every passing second, I slipped the cock sleeve over my tender dick.

“Goddammit!” I didn’t have to play that up, either. The sleeve on my already sensitive tip hurt like hell, but I didn’t mind a little pain. Though it would’ve been infinitely better if I had a Daddy here to command me to take it for him.

As I paid cumdump125 his winnings with my suffering, I let my mind drift to Henry. I wanted him here commanding me. I wanted him to order me to suffer, to take the pain for him so he could be proud of me. So he’d call me his good boy.