Very important question!
To kick things off, you should talk online before any physical meeting. Make it clear that you are nervous and want to be sure they’re worth your time. Be explicit! If they yell at you or tell you that you have to push your boundaries because you’re just a cunt or whatever, stop talking to them. I have talked to too many women who heeded the warning signs too late. Any guy who is unable to distinguish the fantasy part of your relationship from the empathetic part is NOT SOMEONE YOU NEED TO BE TALKING TO.
After you’ve talked for a while online, maybe graduate to texting or phone calls or Skype. It’s only after it becomes clear that you have both some sexual chemistry and some emotional chemistry, that should you meet.
The first time you meet DO NOT HAVE SEX. At all. No sex. Make it clear beforehand that sex of any kind is 100% off the table. It’s an opportunity to get to know each other, to see if it will work. And if ANYTHING feels weird or off, do not escalate things. I can’t stress this enough. Even if you can’t articulate what is making you uneasy, trust your intuitions. Don’t do the girl thing, where you feel obliged to make people happy, to sacrifice for them. You are not under any obligation to let them fuck you. You don’t owe them anything. Just try again with someone new. Or, at the very least, ask to meet again in a sex-completely-off-the-table environment.
Once you’ve screened your way to an actual sexual encounter, lay out some clear ground rules. Establish a safe word. Anyone who says they don’t do safe words is a piece of shit and you should toss them to the curb. Lay out a set of things you are willing to do the first time – and keep them well below your thresholds. Make them prove that they can honor those restrictions before you expand the menu. Even if you think you want to expand beyond what you put on the menu, wait until your next time. Over time, as you get to know yourself better, you’ll develop a good sense of where you can be pushed in a hot and fun way, versus when being pushed will end up being traumatic. But when you’re just getting started the guidelines are important to prevent yourself from hurting yourself, too.
If at all possible, arrange to play in a situation of your choosing. Maybe at an event where other people will be. Or you can arrange a hotel room or something. If you have friends that you can trust to tell what’s up, inform them where you’ll be and tell them that you’ll call when things are done to let them know you’re okay. Ideally, you should give that friend the info about your play partner – and let them know that you’ve done so. I know it’s a little embarrassing, but it’s really important.
I know I’m stressing a bunch of the negatives about this stuff, and I don’t mean to be a downer. This stuff is a blast! You will have a great time. But I just want to reiterate that you are 100% in charge and need to make it clear that this is the case. Even if what you want is to be treated like an object, you need to remain in control of the start and end to that fantasy. Anyone who objects isn’t worth your time.
