17. My Ruin
My day at work turns out busier than most, and I end up having to text Oliver that I’ll be late to pick him up. I hate to keep him waiting, but it can’t be helped.
As midday turns to afternoon, my mind keeps replaying last night’s phone call.
I didn’t mean to take it that far; I didn’t mean to have phone sex with him in the middle of the night.
But he needed me in that moment, and as always, I have a hard time denying him when he needs me.
The urge to take care of him and make him feel good is constantly on my mind, and now, that urge is even stronger than before.
Finally, I finish up work and drive to his apartment building, my stomach clenching as I weave through traffic. I don’t know why I’m so nervous. Well, I do know; what’s about to happen tonight is one step closer than I ever thought I’d allow myself to go.
Oral and handjobs are one thing, and those were a first for him, too, but this feels like a whole new step that I’m not sure I’m ready for. I’m not sure my conscience can take it.
If he weren’t so inexperienced, maybe I wouldn’t feel so guilty. It shouldn’t matter—not really. Having sex with him at all is bad enough, but taking his virginity… God, I can’t think about it too deeply; otherwise, I might back out of the whole thing, and I can’t let him down.
He trusts me to guide him through this new experience. He chose me. He begged me to do it. The responsibility is so vast, so heavy on my shoulders, that I can barely breathe if I think about it too much.
I try to tell myself it’s better if it’s me than some stranger. I know I won’t hurt him; I don’t know that about other men. If I refuse him, he might go to someone else. Someone else who’s older—someone who wouldn’t care about him the way I do.
Maybe this is just me trying to justify it to myself, to the universe, but so be it. It’s too late to back out now. He needs me.
When I pick him up, he throws himself over the center console and gives me a hug. I can’t help but smile, some of my guilt eclipsed by the excitement in his eyes.
“Did you get them?” he asks as I start driving.
“Yeah.” I went to a sex shop yesterday and bought him the toys: a butt plug and two dildos, along with a bottle of lube. “But don’t you want to eat first?”
He shakes his head, bouncing in his seat. “Not hungry.”
I can’t help but smile at his eagerness. He’s a little too eager, to be fair; I doubt we’ll be able to go all the way tonight. I won’t let him be in pain.
“Don’t you remember what Daddy told you?” I ask.
“Um…”
“About patience.”
“Oh! Yeah. Sorry.” He squirms, legs opening and closing. Christ, is he hard already? I shake my head and chuckle as I drive us home, and he practically runs to the elevator and slams the button to my floor.
When we get inside, he dashes into the bedroom. “Where are they?”
Before I left for work, I washed the toys and laid them out in a row on the bed, going from the smallest butt plug I could find to a dildo almost as thick as my cock.
“Are these things really needed?” Oliver asks.
“Yes. I want to do this right by you, Ollie. I don’t want you to be in pain in any way.”
“Won’t this hurt?” He picks up the butt plug.
“Not if I can help it.”
He turns to face me, and our bodies drift toward each other like magnets. I put a hand on the back of his neck, and he stands on his tippy toes and gives me a kiss.
“Are you nervous?” I murmur against his lips.
“A little. Are you?”
I nod, gritting my teeth. I’m nervous, alright. I want his first time to be perfect. If I can’t give him a good experience, there’ll be no doubt in my mind that he should’ve chosen someone else.
He reaches up to caress my cheek. “Hey. You’ll take care of me, right, Daddy?”
I turn my face and kiss his palm. “Yeah, sweetheart. Daddy will take care of you.”
He whimpers at the term of endearment. I bet he’s more nervous than he lets on. His unending trust is the greatest gift of my life; I don’t have words to tell him how much it means to me. All I can do is kiss him again and lead him gently toward the bed.
I lay him down on the mattress, and he lets me undress him.
I’d planned to stay clothed for a little while, just to prove I’m doing this primarily for him, not for me, but he reaches for my shirt and tugs it over my head, and then unbuttons my pants.
Soon, we’re naked, me lying on top of him, our kiss turning heated in no time.
I break the kiss to look him in the eye. “I need you to understand something.”
“Mm…” Oliver rocks his hips, his dick leaking precum against my thigh. He already looks completely lost, eyes half-lidded and a flush creeping up his neck.
“Oliver.” I sharpen my voice, and he stills, looking up at me with renewed focus.
“Yeah?”
“You need to talk to me, okay? That’s the only way this is going to work. If you’re hurting, I want you to tell me. If you want to stop, I want you to tell me.”
“I promise.” He drags his erection against my belly, moaning. “And if I feel good?”
“Then tell me that, too.” I kiss him some more, and I can tell he’s close to coming already—good. I’ll let him come as many times as he wants; it’ll relax him.
He moans into my mouth, and when I break our kiss, he whines. Maybe it was a mistake to get naked with him before I’ve told him everything I need to say.
“Now… don’t be upset if we can’t do it on the first try. You’re so tight, sweetheart.”
He pouts at that, looking displeased.
I stroke his cheek. “Talk to me. You promised, remember?”
“Sometimes, you make me feel like… like I’m the only one who wants this.” He parts his legs wider, tilting his hips until my cock slides between his ass cheeks. “Don’t you want my hole, Daddy?”
I growl under my breath. “I do. Fuck, Oliver, I do.” He has no idea how much I want it, how much self-control I’m employing to avoid doing something rash.
“Then take it. Be my first. Please, Daddy.”
My dick throbs with aching arousal. One sharp inhale, and Oliver yelps as I flip him onto his stomach.
Like last time, I’m left staring at the pale expanse of his back and his plump little ass.
God, everything about him is calling to me.
His tiny pink hole nestled between his perky ass cheeks, his arched back, and his soft gasps of anticipation…
Get a hold of yourself. His pleasure is my only priority tonight—not my own.
“Did you like it when Daddy kissed you here?” I bring my thumb between his legs, rubbing his dry hole.
“Yeah, loved it, but…” He bites his lip, looking back at me with flushed cheeks. “I might come if you do that.”
“Then come. You can come as many times as you want.”
“But…”
“But, what, sweetheart?”
“What about the toys? I want to be ready for you, Daddy.”
“Don’t think about that now. All you need to do is relax, okay?”
He squirms. “I’m not good at relaxing.”
“Try your best for Daddy.”
A shuddering sigh, and the muscles in his back lose some of their tension. “For Daddy.”
I dip down, and as soon as I lave my tongue over his hole, he tenses up again, grasping the sheets.
“Oh, God… Yes.”
I part his cheeks with both hands, making my tongue sharp and pointy as I press it to his rim. Last time, I managed to wiggle my tongue inside him, but this time, he feels tighter somehow. Probably the nerves.
I take my time eating him out, worshipping his hole with my tongue.
After a while, I trail down his taint and lick his supple balls.
Tugging his cock out from under his body, I lick him there, too, tasting the precum at his tip.
That drives him crazier than anything; he’s moaning so loudly I’m pretty sure the neighbors can hear us.
“Please! Wanna come, Daddy. So close.”
I travel back to his hole and hold my tongue there while I jerk his cock.
One stroke, two strokes, and that’s all it takes.
His thighs tremble as he cries out and comes, his hole fluttering against my tongue.
Fuck. Giving him pleasure is quickly becoming my greatest weakness.
Granted, everything about him makes me weak.
I lie down beside him. Moving us away from the wet spot he left on the sheets, I pull him into my arms and hold his sweaty, trembling body.
“Felt so good,” he whispers, an edge of disbelief to his voice. “Everything you do feels so good. What about you, Daddy?” he continues, sounding a little overwhelmed or maybe just impatient. “Want to make Daddy feel good, too.”
“Shh. We have time. You don’t need to worry about anything when you’re with Daddy.” I kiss the whimpers from his mouth, holding him close. Then, feeling like he needs more reassurance, I add, “Daddy loves making you feel good, sweet boy, so don’t worry about Daddy’s pleasure.”
I give him more indulgent kisses, and he lets out a sigh of relief into my mouth. Arching toward me, he strokes his palm over my furry chest, over my biceps. Sooner than I expected, his kisses grow more heated, more desperate.
“Want Daddy’s finger.” He takes my wrist and leads it behind himself. “Want it here.”
I reach for the lube by the bedside and squirt some into my hand. Oliver lifts his leg over my hip, giving me better access to his ass, and I kiss him as I stroke my wet finger down his crease.
“Mm…” He moans into my mouth, hiking his leg up even higher.
Making sure to get plenty of lube around his rim, I caress him softly for a while without trying to press inside. When I feel he’s sufficiently relaxed, I apply more pressure, and he gives a gasp, his hard cock rubbing against me and leaving a trail of precum on my lower stomach.
He’s so wet, so wanting. Everything about him is thrumming with anticipation and need.
“Remember what I said last night?” I ask. He’s so lost in his pleasure that he only manages to shake his head and make a whining noise that I suppose means no. “Your breathing,” I remind him. “Take a deep breath, and when you exhale…”
He inhales obediently, his chest filling with air, and when he breathes out, I press my finger past his quivering ring of muscle. Inside. I’m finally inside.