Page 44 of Ruined

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.