In her mouth

"Son..." she shakes her head, seemingly admonishing you for the crass choice of words. But then, surprisingly and probably due to you having introduced the word in an either-or-question, she responds in kind: "I wouldn't even know how to milk you with my... with my asshole. No, it will have to be my mouth. I will have to milk you everyday in the morning with my mouth."

"Hm." you nod as if this was a perfectly neutral exchange in which you are together trying to solve a problem she's having. "That's an interesting idea you've had. You could just blow me in the morning till I cum in your mouth - I think for it to be considered milking I will have to stay inside while cumming - and then you can go on with your day. Only issue is..."

"What?" she asks with a little desparation. She's beet red in the face as within her, the embarrassment of a prude mother fights with a deep relief that her artificial but absolute desire is going to find an outlet. That relief is now endangered by your hesitation, causing her immidiate stress.

"Well only issue is," you continue, "that this may take a while. In the morning I'm usually pretty hard, but that doesn't mean I can cum that quickly. I may have to skip some days to get to school in time."

"You can't!" she exclaimes, clearly desparate. "We agreed I could milk you with my mouth! We said there would be daily milking, and it has to be on you because my breasts are going to be filling up without release for most of the week! You can't just go before having been milked by my mouth! Never ever." she adds, intent to impress the importance of the situation on you.

"Well if that is so..." you begin, "then I think you have two options. One would be - and I'm asking you which one you'd rather have - that I'll really try to cum as well as I can in the morning, really focus on maximizing my pleasure as much as at all possible. That way I can be pretty sure that I'll cum early enough to get to school, or for you to get to work." you see her face light up as you mention that, making your dick twitch, but you continue in a more severe tone: "That would mean using your mouth as a fleshlight though. It would mean I'd have to be able to absolutely fuck your throat with no regard for how well you can take it. It could well be that I'd so pound your throat some days that that glass of whole milk you drink every morning will come up again - a small milking of your own" you throw in a joke, but she doesn't react to your comedy. "That'd where I'd have to cum then, in the back of your throat, because as we agreed before, it's only properly milking if the results actually pass through the milking machine."

She shudders. "And what is the second option?"

"Well" you say "in the second option we'd also have to do some deepthroating, but it'd be much more controlled. You see, while I can't control well when I cum, we could change the fluid that you ought to extract from me, daily, and with your mouth."

"That sounds interesting" she admits. "What did you have in mind?"

"I was thinking of my pee," you say with some played trepadation. "That could feasibly work as a substitute. Only problem is, you can't just passively receive it, or it's not milking, is it. And you have to use your mouth as we have already said. So I think in order for it to work, I'd have to get hard enough to really fill out your throat, stick my dick in there and then have the tightness of your throat massage out my piss into your stomach."

You look her in her deep blue eyes and say with as much earnesty as you can: "else it wouldn't be milking."