You mention: "I'm sure there are many men who would be much more comfortable in this type of relationship but are unable to express themselves because of societal norms." I agree with you. I also believe that there are a great many women out there who would be much happier and fulfilled if they were to embrace dominance. Unfortunately, societal norms work against us all in this regard. In your view, as a dominant woman, how should a man seeking a relationship in which he would be the submissive partner present that to the woman he is interested in? Is there, in your view, a best way for a submissive man to approach a dominant woman? Likewise, in your view, is there a best way for a submissive man to communicate his need for submission to a vanilla woman, or a woman who has not yet discovered her desire for dominance?
I most certainly agree that societal norms work against all of us in this regard. It's sad that most of us grow up trying so hard to be who other people think we should be as opposed to finding our true selves. I often gravitate towards sports analogies to make a point. My dad was a coach and his entire working life was in one way or another related to athletics. I also played sports as a child, in high school and in college. Successful coaches have a knack for putting people in the right places or situations so they can be successful. The same can be said of good managers. Players who are miscast or put in the wrong positions, situations, etc. won't enjoy the same level of success, and will most likely fail. Getting back to relationships, how many of us are miscast in our roles?
The genetically submissively-wired male who is cast as a head of household will struggle with the role and likely remain unhappy. The same is true of Dominant Women who try to fit into that "submissive wife" type role. While many try to make it work and plod their way through the relationship, many fail and others fail to achieve real happiness.
For a submissive man, I suspect the challenge of finding the right partner and communicating his true feelings to her is often daunting to say the least. In addition to the societal norms I mentioned earlier, there are many other issues that must go through their mind. I'm certainly not an expert in this area, not that anyone really is, as my own experience has been rather limited. I can only share my own feelings and thoughts on how I think submissive males would be most successful. I also think there would be a stark difference between a situation in which the male was merely looking for a play partner and one where he was seeking a committed relationship. For the sake of this discussion, I'll focus on the latter.
Above all else, a committed relationship has to be based upon more than a couple's sexual fantasies, fetishes, etc. Simply put, they have to "like" one another. Life's realities surround us every day; Work, family, illness, death, financial decisions, children, the list goes on and on. These are all major issues and incredibly important parts of our lives. If you are going to be happy, you and your partner have to be able to get through these things together.
I'm not minimizing the importance of sexual compatibility but rather, pointing out that your potential life partner has to be attractive to you in other ways. The quality of communication you have with a potential partner along with honesty are perhaps the two most important factors in my opinion. Keep in mind however, that communication involves more than just talking openly with one another. "Listening" is communication's most important aspect.
A man who has interest in a woman should first and foremost be a good listener. Listen for certain "cues" in what she says that could open the door to the conversation you have been looking to have for so long. If you've already been intimate with her, then you may already have an inclination as to what she enjoys. Is there anything you've done or she's said that would lead you to believe she might be interested in the lifestyle relationship you seek. If so, then you need to bring it up at the right time and be honest with her. Ask her what she would find important in a relationship. That often could lead to other questions.
She may ask you the same question. Be honest in your answer. Tell her it would be important to you to find an assertive woman, one who is comfortable being in charge. Let the conversation flow. Listen, listen, and listen some more! Don't push it. If you feel she is not amenable to what you suggested, you have a decision to make. My dad use to tell me not to expect someone to change for the better once you married them.
During your dating phase, you are likely seeing people on the best behavior. How right he was! I have my first (and very brief) marriage to prove it.
To a great extent, the male also has to get over the fear of rejection, ridicule, etc. I may be making it sound easier than it is, but if it happens, it is not nearly as disastrous as you think it is. If you get to know someone well enough and develop a certain level of trust, the discussion might be easier than you believe.
A submissive man, or any man for that matter, should always approach a woman with respect. If a submissive man already knows that a woman is Dominant, they should never be so forward as to assume that the Domme has interest in them simply because they are submissive. Different situations (i.e. play party, scene, vanilla gathering) would seem to call for different approaches. I would be incredibly annoyed if a submissive man approached me, dropped to his knees, began calling me Mistress, etc. as part of his introduction. That might suit some Dominas but in my case, it would make me uncomfortable and turn me off immediately. I would much prefer a simple and respectful approach. Just introduce yourself with a "hello, my name is.... and..."
Think about what you are going to say, and make it appropriate and in context to the current situation. While this can be difficult if you've never met before, the fact that you are in the same place or social setting will likely provide some conversational topics. Seeing a Dominant woman in a cafe or other public setting and wanting to reach out to her can be easier than you think. Usually, a simple compliment works.
I recall one situation where sissy and I were out shopping for some lingerie for her. After the purchase, a gentleman approached me, excused himself and complimented me on how "expertly and professionally" I handled my purchase. I wasn't aware of it, but he had seen the whole thing. He was polite, brief and very complimentary. We exchanged smiles, I said thanks, and we continued on our way.
I recently had a discussion with a close lady friend who is fully aware of our lifestyle about people who are "vanilla." Her contention is that there are probably few, if any, truly vanilla people in the world. Those who are vanilla, according to her, simply haven't been made aware about the various lifestyle "options." Her belief is that, on a linear scale of 0-10, with totally vanilla people falling exactly in the middle or "5"(for the sake of this discussion vanilla people will be defined as those who are neither submissive or dominant), there would no "5's." She believes that everyone has some leaning one way or the other. She's probably correct. If so, to answer the last part of your question, the first step would be to identify your possible partner's leanings and then broach the subject in ways I described above. Start off slowly, yet don't be too careful so as to avoid the essence of what you want to talk about altogether.
Personally, I think the best of relationships are the result of an evolutionary process, one where deeper submission or for a Domme, dominance, are achieved through incremental steps. That journey is a learning process for both partners. It's what sissy and I have experienced.
With the right partner, the journey can branch off into many different directions. All that being said, my recommendation for a "best way" would be to adopt an incremental approach and be astute and sensitive to your partner's reactions. A whole other area of a discussion on this topic involves the use of the ever-growing number of online dating sites, from vanilla to kinky and everything else in between. With a carefully worded and prepared online introduction/ad, a submissive man can spark the interest of a Dominant woman even on a totally vanilla dating site. Take the time to write a good introduction.
Again, whether on line or in person, be respectful when approaching any Domme. If you aren't, any interest they show in you is not very likely to be sincere.
