A couple of things floated through my head today, one of which was brought on by a conversation about my past history and the other was based upon re-reading some old entries on another blog to refresh my memory in preparation for writing Arc 5 of fs01.
From a sub's perspective, I think it's probably a great disadvantage to have gone through several significant D/s relationships. Each Domme has her own distinct style and preferences for lifestyle dynamics. I know this was very clearly the case in my own relationships. While I had hoped I would only ever need one relationship for the rest of my life, that unfortunately wasn't in the cards for me. It did lead to a variety of experiences that I probably wouldn't have had otherwise.
When a D/s relationship builds around two central parties and the sub has little or no previous experience, I believe the gradual progression and growth by both parties tends to happen in a symbiotic way. I've seen this while following other bloggers as they catalog the progression of their relationship. Sub gets experience, craves more. Domme gets experience, builds confidence, craves more. Over time the dynamic grows more and more intense but always in a way that builds off of the previous experiences. Assuming this relationship lasts at least 2-3 years or longer, it's pretty safe to say that most things "fit" pretty well in the long run.
If you aren't so lucky to have one relationship last, you're faced with a much more difficult task. Each relationship where you reach a state one would call "trained," you have been acclimated to a certain dynamic and set of rules and expectations. Assuming regular play is involved, your kinks are shaped in a way that works for the both of you. If you picture yourself as somewhat of a "blank slate" at the start, if this relationship ends, your slate is now partially filled in with permanent marker. Successive relationships gradually erode the open space and you find the deeper parts of your submissive have some fairly well-defined "triggers" that get you there. If you are like me (using a description I am borrowing from a commenter) and "addicted" to deep levels of subspace, it feels almost as if these marks have been carved into the slate. Changing to reverse those needs seems impossible or at least very difficult.
This creates a very difficult position to be in when it comes to "future relationships." On one level, you are a weathered veteran and no one can doubt that you are serious about this lifestyle. You aren't some wanker playing around in fantasy-land. You're all in. This is a need, not just a sex preference. You are no longer a blank slate.
In some ways I feel like this is the difference between being a virgin or not. Virgins may offer some appeal in that there are special experiences that can be shared with them that can only be had once. They are more likely to be open-minded and allow coaching to do it right. Non-virgins have the advantage of experience and the skills repetition can hone, but they already have an idea of how things should be done, which may or may not be how the other person likes it.
This is not to say that an experienced sub should feel like they are used or damaged goods, but the more sexual conditioning they have experienced, the more likely it is they will have to compromise in a future relationship and/or find someone who desires similar things to what is already clearly defined.
On occasion I have toyed with the idea of it being fun to go back to the days when just bondage was enough to get my head spinning. That's not really realistic in the slightest so it's just an idea to be toyed with... it would be a lie to try to deny it though.
I think looking at how this same thing applies to Dommes is what makes it feel... rough to be a sub. A Domme who has specific needs can basically choose someone who shares similar interests... or find someone who has a much cleaner slate and progress towards those interests with them. Another option that I have seen done is to take on multiple subs to fill all of the roles if it is too difficult to locate a submissive Swiss army knife that is capable of the entire package. It just feels like there's a lot of hope and potential here with the ability to shape someone or composite needs together with multiple bodies.
A veteran sub doesn't have the luxury of serving multiple Dommes in order to cater to their own needs or subspace so in may ways I think it can be a lot scarier.