Over the years I've had my fair share of good luck when it comes to successfully courting Dommes and I've given out quite a bit of advice to subs looking to court Dommes. I consider myself to be average to below average when it comes to my looks and physical attractiveness, job quality, etc. so I must have done something right in making a good impression.
Now that I have a blog I figured I would post my advice in full. I covered several of these a little over a week ago but I figure they could easily have their own post.
1. Be courteous, respectful, and have good manners.
This should probably go without saying but one of the biggest turn-offs many Dommes have are subs who fail to meet these basic requirements. This is the most important thing in making a good first impression. If you are contacting them through an adult dating site, make sure you read her entire profile first and adhere to any requirements she might have. Write out a well-thought message (complete with spell check) that indicates what you find interesting about her (aside from her looks and your fantasy) and what you have to offer. Do not send a picture of your penis unless she specifically requests it. It doesn't take a lot of effort to be a perfect gentleman.
Most Dommes on adult dating sites receive 20-300 messages per day from potential subs, 90% of which are disrespectful, thoughtless, or downright crude. If you are approaching a Domme in public (at a munch, play party etc.) you have to be twice as well-behaved since there is only a limited chance that she is actually looking for a sub. If she says no, be courteous and get out of her face. If you don't, you can basically assume you will be blacklisted within that community.
2. Be a real person.
No one is "just a sub" all the time. No Domme is "just a Domme" all the time. Even if both of you are seeking a 24-7 lifestyle relationship, you have to come off as more than just a live in servant (unless that is specifically what she is looking for). Have interests. Have feelings. Have dreams. Have goals. Have a personality. Have a sense of humor. Just like in vanilla relationships, all of these things will be important if you want to be an appealing life partner.
If you are as interesting as a box of hair, expect to be discarded as easily as a box of hair. She won't want to be burdened by having to keep you occupied and entertained all day every day. That is higher maintenance than being needy.
What are your favorite movies? Books? Music? Hobbies? Sports?
If you can pique her interest as a person, you are much more likely to succeed in winning her over. If you are smart, funny, and caring it will go a long ways.
3. Have a philosophy and a good grasp of yourself.
It's easy to think about the sub you want to be. Hell, most subs have probably fantasized about Femdom situations for years before they act upon them. If you haven't thought about it, think about it. If you have thought about it, refine it a little more.
Step One: Define your idealized form of submission.
If she is the right match for you, your ideal and her ideal will likely coincide. This is not about what kind of play you enjoy or what kind of kinky fantasies you wish to have. Dommes an advantage since they can have rather meticulous expectations for a sub. Think about what types of characteristics and responsibilities those entail. Should a sub perform all of the household chores and domestic duties? Should a sub have any expectations of rewards or pleasures? Should a sub expect to be treated as a lover?
There is no right or wrong (although some of them should be obvious), but more a matter of preference. If your view of being a sub involves few responsibilities, you will probably be looking for a less strict Domme or a switch. If your view of being a sub involves extensive micro-management, that will be targeted towards a particular type of Domme. Some Dommes want a sub that is their lover, others may want a strict code of Mistress/servant formality. D/s relationships that work out generally will have idealized ideas of submission that share similar traits.
Step Two: Realistically evaluate yourself in regards to your ideal.
Unless you want to be accused of a bait & switch, you should probably have an honest evaluation of how close you are to your own ideal. If you believe you should be doing all the housework but don't know how to clean an oven, you should probably note that (e.g. "I will need training before I can perform at an acceptable level"). If where you stand now is light years away from your ideal, I would recommend doing a lot of self-improvement work to get closer because unless you're just an amazing guy with incredible magnetism, being too far removed will hurt your chances.
To be continued...