17. My Ruin #2
“Oh,” he gasps, his cock jumping against my stomach.
“Good?”
“Yeah. Feels… big.”
I smile a tight smile. If he thinks my finger feels big, my cock will feel impossible.
I hold still for a while, letting him get used to the sensation. When he starts moving his hips, I press a little deeper, to the second knuckle. His hole clenches around my finger, and his insides are soft and impossibly warm.
“Are you ready for more?” I pull the finger out and squeeze my untouched cock to relieve some of the pressure in my balls.
Eyes closed, he nods, and I grab the steel butt plug. Its tapered tip is barely thicker than my finger, but anything that will get him used to having something in his ass is good as far as I’m concerned.
Applying lube to the plug, I bring it to Oliver’s crease and rub it over his hole.
“It’s cold,” he hisses.
“Sorry.” Damn, I should’ve warmed it up first. I kiss him while I hold the plug in my hand, waiting until it’s reached body temperature before I try again.
More lube, then I nudge the tip against his hole once more, carefully watching his expression.
Slowly, slowly, I start pressing. At the widest part, his hole offers some resistance, but after a careful push, the plug pops inside all the way.
“Oh,” Oliver gasps, wiggling his hips.
“How does that feel?” I stroke a finger over the base of the plug, my breaths coming out fast and my cock throbbing with need.
“Feels—good,” he moans, eyebrows upturned.
“No pain? Remember to be honest. Talk to me.”
“Um, there was… at first. At the widest part.”
My heart sinks. “It’s good that you told me.”
“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.”
“I’m—I’m trying.” He’s breathing too fast. Hyperventilating.
“Shh, slow down. Breathe slowly. Big breath in, remember? Deeper.”
He struggles to do as I say, but eventually, he succeeds, and on his exhale, I push again. My cock strains against his opening, but it won’t let me inside—not easily, at any rate, and I refuse to push harder than I already am.
“I’m sorry,” Oliver gasps. “Just… just do it. Fuck me.”
“I don’t want to hurt you, sweetheart.”
“You’re not. Please…” His voice turns into a whimper of pain when I try again, and the smallest “ow” falls from his lips.
You’re hurting him.
My stomach drops, and I try not to show the distress and guilt on my face as I pull back.
“No, it’s okay.” Oliver grabs my arm. “Try again, please.”
During all this, my cock has softened, and in the wake of his pain—even the slightest hint of it—I can’t bring myself to continue.
I should have insisted on the second dildo. I should have spent more time preparing him, used more lube. No… I shouldn’t have done this in the first place.
He’s not yours to take.
“Please,” he says again, and I shake my head.
It’s hard to even look at him through the guilt tightening my chest. I rise to my knees and get off the bed. “Bathroom,” I mutter, my heart twisting with regret and my mind overrun with thoughts of wrong, wrong, wrong.
In the bathroom, I try to gather myself enough to return to him. I know he’s all alone on the bed, devastated, thinking this was his fault when the fault is all mine. I stare at myself in the mirror, hands clenched on the sink, and think again of all the reasons why I’m wrong for being with him.
And yet, all those reasons aside, I know I can’t resist him. I can’t turn him down when he’s begging me like that; I can’t leave him alone to cry on the bed.
Oliver… My sweet Ollie… He’ll be my ruin.