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The Art of Suffering for Pleasure
As a Dominate, Top and now a Master for a long length of time in practicing BDSM, I have been known to give sound advice to those that need to know the things that will help them be successful.
I strongly resist the "you can't train someone to be a Dom" language, because while there are real truths in it, it's misinterpreted and weaponized far more often than it's understood.
It's like saying that you can't train someone to be an artist. Hogwash. There are some things that seem to be innate or untrainable, that no amount of training is going to be a substitute for, but at the same time, without practice, experience, training, technique, and a lot of hands-on putting it all into practice, someone can be as artistic as you can imagine, but they'll never be an artist. For that, someone has to do enough art that their internal experience is of channelling and training that internal artistic drive into art, and developing a bone-deep understanding that yes, they really can do it when they decide to.
And there's a really pernicious myth that the community, unfortunately, doesn't do a lot to dispel. If you listen carefully, a lot of the language that is used implies that dominance is something a Dom does to a sub, that the Dom is doing it unilaterally, and the measure of dominance is how much the Dom can impose their own will on a sub without interference from the sub. That myth is expressed the other way, too, that a "real" sub doesn't have opinions, desires, preferences, the right to feedback, or participate in any way other than lying back and taking what is dished out (or leaping up and obeying without question.)
Whether or not that's a worthwhile or achievable end goal (and I would say that even if it is, its largely a matter of taste, because lots of people don't do it that way and wouldn't want to), whatever else is true, it almost never works that way for novices, and, for all sorts of reasons, probably shouldn't.
The way you avoid that is to remember at all times that your partners and playmates are real people. The single biggest and best resource any Dom has for success is the sub they are dominating. The feedback about what's working and how well, what can be tweaked - and the experience of learning to adapt and grow, the praise and enthusiastic participation of someone who's thoroughly enjoying what you're doing, or thoroughly satisfied with serving, are the best tools for having success, and having success develops confidence. (Often, it's a good idea to agree to hold some of that input for after things are done and you're both back on the same planet, rather than trying to do it all in the moment, but that's a separate matter.)
Confidence is a matter of expecting to succeed, and knowing that you can deal with any glitches or issues along the way to rescue a success out of a potential failure. To develop that confidence, you have to have successes that you know are successes, and you have to know (usually through experience) that you can identify and head off problems and turn them around, or worst case, that you can have a failure of some kind, survive it, and learn from it for next time. Confidence is "nothing is likely to go wrong that I can't handle, so I'm free to engage in what it is I plan to do."
So, yes, start small. Separate out your skill level for safety from your skill level for technique, and always stay well within your "comfort zone" for safety - never do anything you aren't confident you can do safely - while letting yourself take risks with things that you might not be able to do smoothly.
Be honest with yourself and your partners, and choose partners who are willing to let you be awkward and get better. Don't ever set perfection as a minimum standard, but hold onto it as an inspirational target. From there, if you must judge, judge yourself on whether you've gotten better, had fun, been safe, and both had and been a good time.
Most subs don't demand perfection, either, unless for some reason their playmate has announced that they are perfect and sets that as an expectation. Most Doms overlook that many, if not most, subs, take joy in being supportive, being allowed to praise, and being able to participate in someone's growth. It's a temptation for those of us who pride ourselves in our skills (or who want to develop skills to be proud of) to make the skill itself the goal, and to lose sight of the fact that it's really about the experience rather than technical merit, and if everyone has a good time, technical skill isn't the issue. And if everyone has a crappy time, it's usually not technical skills that are at fault.
It's hard to let go of the past. If something in your past is enough of an impediment, drag it out on the table and take it seriously. "I want to be really good at flogging, but I had some bad experiences where someone shredded me for not being perfect. I'd like to work with you on flogging, but I need to take it slow and I need a lot of extra feedback and positive reinforcement. Are you up for trying that with me?"
If it's less of an actual impediment than a set of bad memories, then build new memories by building new successes. Back up, start slow, and build on the new successes.
We forget how many failures we had when we were learning to walk, or to tie our shoes, or to get food into our mouths with a spoon when we were new at those things. We got good at them because we just kept doing them until we forgot there ever was a time when we couldn't.
It can be easy to get twisted up about "just overcome it" or "be okay with failures along the way, because they can be great learning experiences" in terms of finding a practical approach to actually doing so.
Actually, that's fair enough. So dig into it for yourself. What is it that you are expecting to have happen that you aren’t prepared to deal with? What went wrong in the past (or didn't go quite right), that might be changed in the future?
Barring nuclear explosions, asteroid strikes, and violent political uprisings, the most likely thing to go wrong in a scene are generally relatively straightforward to predict and plan for.
Clear communication, reasonable negotiation, and an emphasis on either safewords or the equivalent commitment to communicate if something starts going wrong head off the majority of “What if I do something unexpected or take things too far” sorts of issues. Not all of them, but certainly many of them. And having something go wrong isn't the same as letting it continue to go wrong.
Further, just because you thought something went wrong, it's important to find out whether your partner felt that way. Sometimes Doms are our own worst enemy, and sometimes we make the mistake of evaluating the success of something based purely on how well it matched our plan, ignoring whether or not everyone involved enjoyed however it actually played out.
Making sure you have enough practice with implements before you take it on the road, combined with starting slow and working up to gain experience and control (the traditional “using the bullwhip on the pillow in the garage for six months” sort of thing, if necessary) goes a long way to head off most of the “what if I don’t know what I’m doing” sorts of issues.
The awareness, and if necessary, explicit statement, that you are human and imperfect and that even when everyone means well, occasionally egos get bumped, feelings get hurt, things you weren’t expecting to say come out of your mouth, and that even well-intentioned and fully consensual things can unexpectedly push buttons or trigger things - and that a sincere apology goes a long way when it’s needed.
Some basic first aid training and supplies cover the majority of the physical oopses - bandages, ice packs (or frozen peas), and things like EMT shears if you are doing bondage.
Then do what you do, and if something goes wrong, hang in there and handle it as best you can. You can’t make it “didn’t happen” but you can usually keep it from getting worse. And again, trust your sub - often, depending on what happened, they feel worse about it than you do, and you owe it to them to shut your own guilt down until their emotional needs are dealt with, if that’s what it takes.
All that, plus time and experience, is what builds the confidence that you can handle what comes up.
Another useful skill to develop is to learn to roll with what actually happens. It's inevitable that unexpected things will happen. It's damn near inevitable that sooner or later, you'll make some minor mistake such as ordering someone to get the flogger when you meant to order them to get the paddle, or that at some point during elaborate ropework, you'll end up with trailing ends that are too short to tie where you planned to tie them, or that you'll realize partway through that the next toy you need is across the room.
You can react by calling yourself stupid, visibly losing your cool, or muttering out loud something like "See, I knew I couldn't do this right." And if you do, hey, you're human. You can say things like "Oh, I'm so sorry, I didn't mean the flogger. I meant the paddle. Sorry, sorry. I'm an idiot. Go get the paddle."
Or you can say "Thank you. Well done. Now put the flogger back and bring me the paddle." You can say, "Hold this and don't move" and go get the other toy. You can say "Now, close your eyes and count to 20 out loud" while you step back and figure out what the heck to do next. You can sensuously untie the bondage enough to back it off and then tie the ropes a different way that lets you tie them off.
Always remember, your partner usually doesn't know specifically what you had planned, and as long as you're not violating consent or hurting them, you're not wrong if you act as though it's what you planned all along. Of course, if something went wrong that needs to be dealt with, don't pretend it didn't. But don't freak out just because Plan A didn't go perfectly. You may get a reputation for being deliciously unpredictable.
And even if your playmate is crystal clear that it wasn't what you planned, it's usually a positive good that they experience that you can be trusted to keep things going and get things back on track without losing the mood. (Or at least, their mood), and that if something unexpected happens, you're up to dealing with it. It often takes a lot of pressure off them to "do everything perfectly" if they realize it doesn't bother you if you don't do everything perfectly.
Remember, you're doing this for fun, for hotness, for mutual satisfaction. There's not a team of Olympic judges watching your every move and scoring you for difficulty and execution. Unless, of course, that's what you've arranged, which could be an interesting scene in its own right.