19. Feel It #2
“You did. You were perfect.” I turn him gently onto his back, and he gazes up at me with rosy cheeks, looking completely lost. “Did you feel any pain?”
He shakes his head. “Not really. The second dildo felt big, but it felt good. Like, so good.”
I smile at the way he stresses that last part. “Good.”
He reaches for my dick, and I lean over him to let him grasp it. His hand closes around my shaft, pumping it slowly. “Can I… Can I get Daddy’s cock now?”
“Is that what you want?” I rock my hips into his hand, unable to suppress a groan.
“Yes,” he whispers. “Want Daddy to be my first.”
It seems important to him—the virginity aspect.
I understand why it excites him. For me, however, it’s merely another source of guilt and hesitation.
I try to tell myself again that it’s better it’s me than a stranger.
That if I stop now, he’ll be beyond disappointed.
That he wants me, that he chooses me and no one else, and to trust him in that decision.
Still, it’s fucking hard. Even now, I can’t tell if I’m making a mistake.
He opens his legs, tilting his hips up, and I slide my dick along his crease, rubbing it over his hole. He’s ready now—I can tell. Even though I’m not trying to push into him, his hole opens for me when I stroke my dick over it, almost sucking me in.
I pull back to coat myself in lube, and when I get into position between his legs, he inhales a sharp breath, eyes widening.
“Relax, baby boy,” I mumble, kissing his plush lips. “That’s all you need to do now. One breath in, one breath out. Can you do that for me?”
He nods frantically, lips parting as he breathes in, then out, and in the moment I deem right, I thrust my hips forward, pushing inside. My jaw is tight when I breach him, making new space for myself where no one’s ever been.
“Holy shit,” he gasps. “Daddy. Daddy, you’re inside me.”
I grunt and nod, face slick with sweat as I pause to let him adjust. “Are you okay?”
“I’m okay. I’m good. Oh, shit…” He squeezes his eyes shut, brows upturned.
“Ready for more?” I’m not even halfway inside him.
“Y-yeah. You can move now, I think. I’m not in pain.”
I thrust forward again, then a little more, and a little more, stretching him wider, gently working my cock into his hole.
“You’re so deep. Ohh… Oh my God.”
I have to pause—not for him, but for me. The tight heat of his hole clutches my cock, bringing me dangerously close to orgasm.
“Do I feel good?” he asks. He must have noticed my strained expression.
I nod, bracing my arms on either side of him. “You feel so good, Ollie. You have no idea. Fuck, your hole…”
“Do you like it, Daddy?”
“Yes,” I say, voice rough. “I love it. Love your hole.”
“It’s all for you. No one else. Daddy’s hole.”
Holy fuck. I force myself to move, wanting to give him more of me, but at the same time, I’m holding back for us both.
“Harder, please,” he moans. “I’m not going to break. I want to feel it—what it’s like to be fucked by Daddy.”
It’s a miracle that I manage to stave off my orgasm when he wraps his legs around my waist and forces me deeper. God, I should’ve known he’d be this needy. I give him a few shallow thrusts before pulling out of him. I flip him onto his stomach, and he cries out when I slide back inside.
I go still, heart pounding. “You okay?”
“I’m good,” he breathes. “Shit, you’re so deep.”
“Too deep?”
He shakes his head, and I move again, angling my hips to try to hit his prostate. This position is usually good for it, although I think his hips need to be—
He cries out, his hole spasming around me. “What was that?”
“Your prostate, sweetheart.”
“Oh. D-do it again. Please.”
He doesn’t need to tell me twice. Pushing him into the mattress, I grind my hips against his ass, hitting his sweet spot with every stroke.
“Ohh my God,” he gasps. “That feels so freaking good.”
I snap my hips forward in a hard thrust. “Do you feel it now?”
He only moans in reply, so I grip him by the neck, murmuring into his ear.
“Do you feel now what it’s like to be fucked by Daddy?”
“Yeah,” he gasps, his voice punctured by each thrust of my hips. “I—feel—it. Gonna—come.”
“Go on. Come on Daddy’s cock.”
A series of incoherent words pours from his mouth as his ass clenches around me, stretched to capacity and milking my dick with all that it’s got. I let go with him—coming with a groan, pumping my cum deep into his warm insides. My vision whites out as pleasure shoots in waves all through my body.
As I catch my breath, I take care not to crush him with my weight.
Fuck, I can’t remember the last time I came that hard.
My skin is still buzzing. Pulling out of him, I lie on his side and turn him around.
Then, I wrap him in my arms until we lie entangled in a sweaty mess.
He mumbles something, too low for me to hear.
“Yes, sweetheart?” I ask.
He nuzzles into my chest, nose burrowing into the hair there, but he doesn’t speak. I stroke his head, tilting his face up.
“Everything okay?”
“Yeah,” he mumbles sleepily. “Everything’s amazing. Came so hard.”
I smile and kiss his forehead. “Me too, sweet Ollie.” I hold him close, breathing in his scent while he drifts off to sleep.
I did it. I fucked him. I took his virginity, and I still don’t know if I made the right choice. Still don’t know if his first time really should have been with me.
I think about the waiter at the restaurant earlier this evening—the way he automatically assumed Oliver was my son.
Maybe it really is wrong to be with him like this.
Should I have never crossed this line? I can’t be sure, and the questions keep me awake while Oliver sleeps soundly in my arms, unaware of my ever-tormented mind.