My poor, distraught Carolina. I hold her in my arms and let her cry on me, wishing I could do more to help. I wish I could kill the bastard who left her just because they couldn’t get pregnant. What a complete asshole.

I look down at her pretty face and smooth the hair out of her tear-filled eyes. She grasps onto me in a way that’s primal, sexual. Despite my best intentions, I feel ready to go again. My cock rises up, hard and at attention.

“Oh, my God,” she says, reaching down to grab a hold of it. “You are definitely hard again.”

“I’ve wanted you for so long,” I admit, leaning down to kiss her head. “And you didn’t even get to finish coming. Let me back in you. Please.”

She looks up at me, a bit hesitant, and it makes me want her all the more.

I take off my tie and bind her wrists to my chair. She’s laying ass up on my desk, and she isn’t protesting.

“The damage has already been done,” I tell her, meaning the broken condom. “But just in case it hasn’t, there are other ways we could…”

“Really?” she asks, craning her neck to look back at me. “I’ve never…”

“You’ve never had anal sex before?” I ask her.

She shakes her head.

I suppose she wouldn’t have had a need to, since she was trying to procreate. And now, the opposite plan is our goal.

“Let me take your asshole for your very first time,” I tell her.

Now it’s my turn to beg.

I place my hands on her ass checks and stretch them out so that I can see her pulsating asshole. She doesn’t say yes or no, but she’s not really in a position to say anything, tied up on my desk, at my mercy, like she is.

I put a finger into her ass hole and she jumps a bit, but I grab a hold of her ass cheek once again.

“Spread your legs further,” I command her, and she does, my compliant assistant. I love seeing her entire naked body, pussy and ass, spread out before me. I smack her pussy with one hand while fingering her asshole with the other.

When she tries to jerk away, I smack one of her ass checks, and then another, until she’s moaning underneath my touch.

“Are you trying to disobey your boss?” I ask her.

“No, I’m not,” she says, as I bring my cock close to her perfect ass hole.

I spit on it for lubrication and I rub her clit while the head of my cock is up against her ass hole. She’s dripping wet for me, so I take some of her juices and rub them all over my cock.

Then I push my cock into her ass hole, and both of us moan together.

“That feels so good,” I tell her, as I slide it into her ass. “I’m taking your anal virginity.”

“Take it, Boss,” she says, rubbing up against me, giving into me now and letting me do what I want with her.

I push in and out of her asshole as I rub her clit. She puts her head down on the desk, in the throes of ecstasy. I’m glad she’s able to come now, fully.

“I’m coming. Garrett, I’m coming,” she calls out, as I thrust in and out of her ass hole while plunging my fingers deep into her pussy.

And suddenly I’m coming too, filling up her ass hole with my load. When both of us are finished, I pull my cock out of her and watch the pocket of cum I left there drip out of her. It’s a perfect creampie, and I put it in her.

Both of us are sweaty and messy, breathing heavy now. I take a deep breath, realizing what I’ve just done, and she appears to be realizing the same thing.

I’ve fucked my secretary. In her pussy and in her ass. With a broken condom, and then no condom at all.

Holy fuck.

I pick up her clothes from the floor and hand them to her, and we both get dressed.

I can’t stop thinking about the risk of her getting pregnant. I know she meant every word she said, but that doesn’t change the fact that she could get pregnant. She isn’t necessarily infertile. I try not to let my concern show, but I have a feeling that I fail. And I also have a feeling that she’s having the very same concerns.

I decide the best policy is openness. As she’s getting dressed, I lean into her.

“You know, Carolina, I am in hot water with the partners already. Truly, I can’t afford to get into any more trouble. We just… I just took such a giant risk. But there is something about you. I don’t know. You make me feel like I would take that kind of risk. I would leap first. For you, it was worth it. I shouldn’t have done it and put you at risk too, but it’s going to be okay.”

“Are you he saying this is it?” she asks.

“God, no. Whatever gave you that idea?”

We are clearly on two different pages, as that wasn’t at all what I had mean.

“I don’t know, that’s just the impression I got from what you just said,” she replies.

She’s fully dressed now. She smiles and hugs me and goes to walk out of my office.

I feel like she might be walking out of my life for good. I clearly said something wrong. I’m not used to feeling so powerless. I don’t know what to say.

As the door swings shut, I sit alone in my office. I’m thrilled to have found someone like Carolina, and I don’t know why I didn’t just tell her that. The words caught in my throat. I was afraid to be too vulnerable, and now it’s too late. I have a bad feeling she thinks that we had made a mistake, or at least she thinks I think that, when in fact I’m thinking quite the opposite.