Page 47 of Ruined

“Now it just feels good, though. Please, Daddy. I can handle it.” He licks his lips, swallowing hard. “More. I can handle more.”

Mouth dry, I pull the plug halfway out of him, and he moans when I push it back in. “Are you sure?”

“Yeah. Feels so good being stretched by you, Daddy.”

I groan, my cock so hard it hurts. At this rate, I’ll shoot before I get inside him.

“I’m ready for the next one,” he says.

“Okay.” I slide the plug out of him and grab the first dildo. It’s in a see-through purple color, thin and long, with a flared base. In terms of girth, it’s not even close to my cock, but we’re getting there.

I roll Oliver gently onto his back, and he lifts his knees to his chest. Our eyes meet as I dribble lube over the dildo and work it all over the shaft. When I bring it between his legs, he knows the drill: he inhales deeply, and on his exhale, I press the tip to his hole.

“That’s it. Relax for me, sweetheart. Let Daddy open up your hole.” With those words, the dildo sinks inside, and Oliver gives a soft whimper. I hold still, letting him adjust. “Okay?”

“Y-yeah,” he says, though his voice wavers a bit.

I pause to apply more lube, and when I push the dildo back inside him, he moans in relief.

“Better?” I ask.

“Yeah. Feels good.”

“You’re being such a good, patient boy, letting Daddy stretch your hole.”

He tilts his head back, cheeks flushing, and when I look down, his cock twitches and spills a drop of precum onto his stomach. I bend down and lick it up, tongue lapping over his smooth skin, over his belly button, and the little happy trail down to his groin. Then I wrap my free hand around his base and give his cock a pump.

He gasps urgently. “I’ll come if you do that.”

“Then come. I told you; come as many times as you want.”

He licks the sweat off his upper lip. “But… I want to come on Daddy’s cock.”

Christ. He spreads his legs wider, and I put a pillow under his hips. At this angle, I can see his hole perfectly—his pink rim pulsing and clutching the dildo as I slowly pump it in and out of him.

“I’m ready,” he gasps. “I’m ready. Please.”

“There’s one more toy.”

“I don’t need it. Need you, Daddy. Need your cock.”

Shit. Even if I manage to work myself inside him, I’m about ready to explode, and I wanted his first time to be different. When I look into his pleading eyes, though, then down to his leaking dick, it’s too hard to resist. Pulling the dildo out of him and setting it aside, I reach for the condoms by my nightstand.

Oliver shakes his head. “You’ve gotten tested, right? Please, Daddy. Want you to come inside. No condom.”

I did get tested after my last sexual encounter, and besides that, I’m on PrEP. Still… this feels like one step too far. I don’t know how I’d live with myself if anyone found out. God, his mother… What would Kim have to say if she found out I took Ollie’s virginity—and not only that, but that I fucked him raw? It’s none of her business; it’s nobody’s business, but still… This feels so wrong. Like betrayal.

And yet, Oliver looks at me with a level gaze, seeming fully aware of what he’s agreeing to—what he’s begging for.

“Daddy.” He grabs my wrist. “Please. I need you.”

And God, how can I say no?

I put the condoms down. Grab the lube bottle. Squeezing a hefty amount into my hand, I cover my cock with it. I still don’t know if it’ll be enough, so in case I need more, I leave the bottle by my side.

Oliver parts his legs wide, inviting me between them. I kiss his sweet lips, caress his smooth thighs, and he surprises me by grabbing my cock and guiding it to his hole. With one push of my hips, I’m inside… or at least, I thought I would be. There’s resistance—more than I expected. Oliver’s mouth hangs open, his warm breath fanning my throat.

“Relax for me, sweetheart.”