Blackmail, or A Moral Dilemma

I have been quite titillated by a number of the ads that I see online. Sometimes I can go quite far down the rabbit hole and spend entire days immersed in the fantasy evoked by an ad.

One category of ads that I have avoided entirely reposting here is that of married men (or women) looking for someone to address the needs not being addressed by their partner. Some of them are quite brave in what they reveal. And there's no way, of course, for anyone but the author to know whether it's real or a fantasy or a private joke. So, I just don't go there.

But someone else has:

An invitation to a difficult choice... - m4w - 30

I am sure this missive comes as a surprise. You have no doubt felt secure in the secrecy of your indiscretion. However, I’m afraid you have been a bit careless in your efforts to cover up the situation. I am in possession of the letters and certain photographs that unambiguously depict your role in this sordid business. A little sleuthing has positioned me to reveal these to everyone – your significant other, your family, and your workplace. I am willing and able to do so at any time. I am well aware of the depths to which this would reduce you.

By now, you are desperately trying to guess my identity. A fruitless exercise, I fear, as we’ve never met before, and I stumbled upon all of this quite by chance. Fortunately for you, my silence in this matter can be bought. I don’t mean with money, of course – I have my own ample means and no need whatsoever for yours. I have an alternate sort of compensation in mind.

Before you leap to the conclusion that I’m demanding a few awkward, one-sided couplings in dull motel rooms, understand that I have as little interest in that as you. Which is not to say that my intentions are strictly chaste, mind you. My interests just happen to lie outside the bedroom. I am curious to see how a woman like you countenances shame and humiliation. You will cater to my whim in this regard, acting in the capacity commonly termed that of the submissive.

What will this entail? Honestly, I am loathe to spoil the surprise, but I suppose a taste of what’s to come is needed for you to make an informed decision. When we take dinner at Aqua, say, I might ask you to retire to the restroom to remove your undergarments, and render them to me, for the duration of the evening. Perhaps in lieu of lunch one afternoon, I’ll request that you take a stroll with me along Baker Beach – the nude portion, that is. Or maybe I’ll register a room at the W for the day just so you can “inadvertently” welcome room service in the buff. If you are in any minor way disobedient or snarky, perhaps I will make you wear nipple clamps while we walk through the MOMA. These examples are purely illustrative, of course, and over time my interests, and your boundaries, may expand. Provided that you are compliant and courageous in the face of an occasional adventure along these lines, I will preserve your secret. From what I know of your inner life, I even harbor an inkling that this might appeal to you, on some level.

I say “occasional” because I am a busy man, and as entertaining as this situation might be for me, I can hardly make a vocation of it. I imagine that my schedule couldn’t accommodate more than one such session every couple weeks, if that. I do however expect you to make yourself available upon request. That much said, we can endeavor to avoid any disruptions in your lifestyle – I have no desire to draw attention to our antics by coming between yourself and your work or relationships. This will merely be our little secret on the side. You are used to keeping secrets, I believe.

When you’ve had some time to think it over, contact at me at the given address and let me know your intentions. If I do not hear from you within a week, then I will begin taking steps to air your dirty laundry. Should you choose to accept my offer, I will suggest a neutral place and time, such as an afternoon at a café, where we might inaugurate our agreement.

You shall know me only as, Mr. W

[[You are female, in your 20s or 30s. You are educated, cultured (you wouldn’t ordinarily feel uncomfortable in any place I mention above, with the possible exception of Baker Beach), financially secure, yet drawn to the prospect of role-playing a submissive. An interest in exhibitionism and moderate BDSM is preferred. You would rather keep our face-to-face encounters as “in-character” as possible. You are intrigued by the psychological aspect of this more so than any physical interaction. You are above all game for some safe, legal, and hygienically uncomplicated fun. Detailed out-of-character discussion of boundaries and directions is encouraged.

I am male, in my 30s, probably overeducated, a little wry and mischievous, tall and quite thin, supercilious, versed in food, travel, and the arts. I am in a long-term and open relationship, and this would be a good match for someone in a comparable situation. In case this somehow failed to be conveyed above, I am not out looking for sex.

For the benefit of any psychotic or deeply troubled readers, this scenario is pure fiction, and any resemblance to your personal delusions/problems is entirely coincidental.]]