A New Adventure!

Here's my news...

I have entered back into the world of Vanilla Dating. On an online website.


I was there once before. Pre-website, pre-Ruby, pre-exploring my kinky side.

In my travels within the kinky community I have encountered mostly men who are up for playing but were not exactly...stable. Whether that stability was lacking circumstantially or emotionally it matters not. They just weren't partner material. Not who I could picture coming home to and snuggling up with every night for the rest of my life. I could picture playing with them (and occasionally did) but the attraction stopped there.

That has been my experience. I don't believe that kinkiness and good partner material are mutually exclusive. I know too many happy kinky couples to think that. But it's just not working for me right now.


So off into the land of the vanilla I go. Here's my theory. A lot of men have kinky underpinnings that they rarely give air time to simply because the women they are with are too sexually conservative (silly women). So these men watch porn, fantasize, masturbate and are reasonably okay with not living those fantasies out. Some of them end up single again - as many of us do.

Imagine they then come across a woman (that would be me) who appeals to them on many levels...and they discover that she's actually kinky to boot? Jackpot. Assuming that the kind of kink I'm into is the kind they have been fantasizing about...which is a big if, admittedly.

I mean, the reveal would have to come early, given this blog and my writings and who I am and all.


So what do I do? Just hand him one of my cards with my website as we part ways after the initial coffee? I have been known to say, "well it's not exactly something you bring up on the 5th date, you know." But I'm not so sure about that anymore. Perhaps it is.

Perhaps the idea of pegging can't really get traction in the mind of newbies without the physical and emotional intimacy that provides a secure container for the required trust and vulnerability inherent in the act. If I just throw it right out there that I love pegging - wouldn't it scare away those men who might easily be persuaded within the context of an established relationship?

Then there's the time question. How long must one "establish " the relationship before forging ahead, as it were?

Dan Savage seems to think it's okay to "take them for a spin sexually" before revealing a kink...but he is a guy, after all. As such he is more prone to prefer fucking someone and then getting to know them than getting to know someone and then fucking them. I see his point but I A) prefer getting to know someone and then fucking them, and B) have been historically bad at keeping secrets. To hide all that for a number of weeks/months would be...a challenge for me. Not impossible, by any means. But a challenge.

I'll keep you updated!



9 Responses

  1. I guess these will all depend on the person and the connection.

    Personally, I’ve never seen the point in some arbitrary delay. You can choose whether to bed someone after a couple of dates (heck, it might be BEFORE you date), but I’d suggest seeing how things go Vanilla-wise before hinting at something else. You may be pleasantly surprised by how receptive people can be during post-coital pillow-talk.

    Have fun out there, Ruby. Hope you and some lucky guy both find what you’re looking for.

  2. You might end up having to broach the subject most of the time, as most guys I know would be too shy to talk about their fantasies.

    Kinda funny how we’re supposed to be so tough and straight forward, but we can’t always say what we want in bed eh?

  3. my current wife introduced me to pegging.
    my former wife was a lot like you described above.
    it was vanilla and I didn’t feel comfortable with her discussing sex. So, accepted what it was.

    my current wife and I talk about sex very well.
    she didn’t throw the strapon on the bed on the second date.
    A bit of finger touching between the scrotum and shaft will tell you where his mind is. For me, I never even thought of ass sex for men. When her finger touched my butt-button, my ass wiggled like I was like a cat in heat. I instantly knew I wanted her finger to penetrate me. When she approached the topic of a strapon and dildo, I stepped back a bit…but trusted her. The next thing you know, I am surfing the net for strapons and information about ass sex for men Thats how I found you Ruby.

  4. Generally speaking, the lustful rush from a woman where an attraction already exists is a most welcome surprise. A woman of kink, who introduces it appropriately, drips confidence and comfort without oozing arrogance. I hope you go in with little expectations, an open mind, and a half cocked smile. Good luck!

    Ps, connection first is importance as acceptance and compatibility is half the thrill

    1. This describes me rather well, I’d say. I’m pretty comfortable with who I am. And I’ve scared off a few but that was bound to happen. I can be a tad intimidating for those unprepared for my honesty and forthcoming attitude. The ones that stick around are quite interesting if only for their willingness to engage with a woman who is indeed a challenge. The rewards are…intense.

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