Page 59 of One More Dare
But that doesn’t mean I can’t encourage him.
“Porter, I’m going crazy right now thinking about you with that dildo stretching your ass, picturing you using it to make yourself come. Do you slam down against it, hard and fast? Or do you draw it out, teasing and slow?”
“Fuck, Will.” He reaches down to adjust his own erection. Holy shit. Seeing the evidence of his arousal turns me on even more, and pride washes over me for eliciting that type of reaction. His pupils are blown wide, and he’s licking his lips as he stares at my dick.
He’s obviously conflicted about the decision. He didn’t say he didn’t want to show me though, he tried to remind me that I’ve claimed to be straight.
I think we both want this, but he needs that final push.
Permission to take what he wants.
“Another dare,” I suggest. “And a promise that this won’t come between us.”
That’s been my biggest concern in telling him I’m attracted to him. So maybe that’s why he’s hesitating now—he doesn’t want it to come between us either. And maybe I’m taking the easy way out by asking to watch him instead of actually hooking up, but this feels safer. If he does agree, we can go from there. But if we’re on the same page, if we both want this, then I don’t see any reason we shouldn’t act on what we both want.
His eyes are big, pleading as he asks, “You mean that?”
“Yes, P. I do.” I give him a moment, and he finally nods.
I let out a relieved sigh. He wants this. Maybe even wants me.
Fuck, this is so hot. I don’t want there to be any confusion over what we’re agreeing to, so I repeat my request. “I dare you to fuck yourself on your dildo in front of me so I can watch.”
“I can’t believe this is happening.” Porter shakes his arms out like he’s trying to physically reset himself, then stands a little taller. A wide smile stretches across his face. “Well, come on then.” He grabs the dildo and turns to leave the bathroom.
All the cold from the lake is completely forgotten as I follow him into the bedroom. My heart is racing a mile a minute in anticipation. My dick feels like it’s going to rip right through my briefs with how hard I am. This is really happening. I’m about to watch Porter fuck himself, and the knowledge of that makes me feel like I could come right now.
“I’ve never done this in front of anyone before,” he admits. “You’re sure about this, Will?”
“Yes,” I answer confidently. A chair is in the corner of the room, so I drag it closer to the bed where I’ll have a clear view. I settle in, spreading my thighs, but leaving my underwear on. For now. It should be clear I’m not going anywhere, though. “Show me.”
A slow smile spreads across his face as he reaches into his bag and pulls out a bottle of lube. I bite my lip to hide my smirk.He seemed to put the lube away just fine.He strips out of his underwear before crawling onto the bed, and my mouth goes dry.
He’s putting on a show, arching his back and swaying his hips as he does. He’s such a tease as he positions himself so he’s sprawled out with his legs spread open, his hips angled up so he’s completely bare for me. It’s the sexiest thing I’ve ever seen.
Porter looks up to meet my gaze, eyes shining with far too many emotions for me to decipher as he mutters, “Fuck it. There’s no going back now.” He coats his fingers in lube and rubs them over his hole. It looks so small, so tight. I’ve been watching enough porn to understand what he’s doing, that he’s prepping himself. A part of me wishes I could be the one doing that for him, but watching him like this, knowing he’s putting on this show for me, and that he’s never done it for anyone else, fuck. The lust that’s coursing through me right now is overwhelming. This whole situation is turning me on in a way I didn’t realize was even possible.
“Fuck,” I breathe out, unable to stop myself. “You look so good like that.”
The hesitance he seemed to have before is nowhere to be seen now. There’s a wicked glint in his eye as he responds. “Like what?”
“The way you’re on display, arching your back like that, getting all open and ready for me… Shit, I mean, for the toy.” A wave of heat washes over me, and I’m sure I’m blushing, but I’m too turned on to care about the slipup. I do wish it was my cock anyway. I didn’t exactly hide that. Would he want that too?
He chuckles low in his throat as he slides a finger inside himself and groans. My knuckles are white from how hard I’m gripping the arms of this chair to stop myself from fisting my dick, but I don’t want to do anything that could distract me from him. I’m mesmerized by his fingers pumping in and out of himself, wet with lube as he adds another. The grunts and whimpers he’s making are driving me wild. Making me wonder what he’d sound like if it was me touching him. If I’m lucky enough to ever get the opportunity.
“Ready for the real show?” he asks, and I nod, not trusting my voice.
Porter grabs the dildo, holding the base as he squeezes more lube onto it. He takes a spare pillow with his other hand and adds it under his hips before bringing the toy to his hole. On a breathy exhale, he slowly pushes the toy in, and his ass swallows it inch by inch until just the suction base he’s holding is still visible.
“Oh god,” I groan, finally giving in and palming myself through my boxers. “You’re so fucking hot. This is incredible, holy shit.”
Porter makes another breathy noise and starts to move, shifting his hips to meet the toy as he thrusts it slowly in and out of himself in a steady rhythm that has me squirming in the chair. Each time the toy sinks fully inside of him, a soft moan escapes his lips, and the muscles in his thighs tense. Sitting here without being able to touch him feels like torture.
But this is what we agreed to. I shouldn’t push my luck. I should be grateful he agreed to this part so quickly.
“Do you like watching me?” he taunts, the confidence I’m used to from him returning in full force as he gives into his pleasure. “Do you like seeing me take this cock?”
“Absolutely.”
