Thinking about rules (#1)

Because reasons, I’ve been trying to negotiate some rules of engagement for an upcoming tryst. We have roles in this negotiation: she must establish some important (to her) boundaries. I have a more complicated job: I must both a) respect – and protect – those boundaries, particularly in the moments we’re together and b) push up against them. Hard. This post represents my first report on the rules-negotiation process.

As you can see, I relish this delicious, excruciating task.

Initially, she wrote:

1. No sex (oral, vaginal, or otherwise).
2. We will mutually agree upon the amount of prep time available before dates. (Time will be scarce for me…. I want to make sure we are both clear about expectations.)
3. Any bruises will be agreed upon in advance.
4. No photos except while on dates.

There may be others, but this is what I can think of for now. Please edit, add, ask for clarifications as you see fit.

I replied, asking for a little clarification. May I finger her, for example? And would she be willing to discuss the photos restriction, as I really, really value photos from her. Both because photos provide a dopamine rush of information about her compliance, and because her body. I also wrote, “A general point: point #1 seems like a very strict, and very challenging, rule. I’m anxious about it. Anxious about my ability to uphold it; anxious about yours. I’m not sure what to do about that, but it seems worth saying. I feel fairly confident that we might fail. That’s not to say ‘no.’ It’s to say precisely what I said: I’m anxious.”

We chatted some more. She said more about her feelings/concerns. I did the same. I asked more questions. I wrote:

Licking? Tasting? Swallowing?
For each yes, please have an orgasm before you respond to this. For each no, please edge.
Then, please tell me how many times you came, how many times you edged, and in what order.
Also, tell me what you were wearing, in what position you were, and the time and location. Of each endeavor.
Thank you.

She responded. One day later. With this:

*I was wearing blue and white striped cotton briefs and a navy cotton T-shirt when I had an orgasm this morning, right when I woke up. I was laying on my back under the covers and my hands were touching my clit outside my panties.

Yes. (Yours and mine.)
*Same as above.

Licking? Tasting? Swallowing?
Perhaps… What is the line between licking, tasting, swallowing and oral sex exactly? (This prompts a fantasy in which you allow me, say three seconds of tasting your cock at a time in between which you remove it from my mouth and stroke it in front of my face and remind me of the rules I set as I writhe in sweet agony.)
*Same as above except I edged for about 30 minutes as per your rules before the two aforementioned orgasms.

This, of course, begged all sorts of questions. (She excels at begging.) I wrote, “I would say you’ll need to tell me those lines. For example, if you kneel in front of me and I stroke my cock and come in your mouth? Or if you have your mouth open and I put my cock in it and you avoid allowing your lips or tongue to touch it? If I blow on your clit while my fingers are deep inside your cunt?”

To which she replied, charmingly, “Fuckity fuck fuck.” And then, five hours later, somewhat confoundingly, confusingly, and excitingly: “How about mouths are okay as long as they don’t directly result in the orgasm? All your examples sound okay to me.”

I’m not sure what to do with that “… don’t directly result….” I mean, she could suck my cock for three hours, and I could take my cock out of her mouth, have her open it, and stroke my cock for five (or fifteen) seconds (or minutes) before filling her mouth with my cum. Would that work? (I mean, I know it would work, but would it comply with the new proposed rule?)

Here’s what I think makes sense: I think she wants to use a rule to resolve a conflict. On the one hand, she wants (needs) my cock in her mouth. On the other hand, she wants to avoid crossing a somewhat arbitrary and mysterious line, a line at which the relationship between her mouth and my cock becomes somehow substantial, as opposed to more… incidental. I think we can use a combination of rules and a timer to accomplish this.

I want to start by describing the form of the rules I’m contemplating, to ascertain if I understand her concerns correctly, and if I’m responding helpfully to them:

1) Her mouth may not touch my cock at the moment I come.
2) In fact, her mouth may not touch my cock within [x] seconds/minutes/hours of any orgasm I might have.
3) There should be a maximum period of consecutive time my cock spends in her mouth, with a minimum break between any instances of my cock being in her mouth. So, for example, she might be permitted (required) to have my cock in her mouth for [x] [seconds/minutes], before and after which, she might be required not to have my cock in her mouth for [y] [seconds/minutes].
4) We might, or might not, establish an overall maximum period of cock-in-mouth time. We could measure this time in seconds, minutes, or hours.
5) I might, or might not, permit (require) her to swallow some, or all, of my cum. Which I might, or might not, deliver into her mouth by my cock, or by some other conveyance.

One part of our rules discussion….

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