Anonymouse is nervous about their first time

Dear Charlton,

I’m on the fence about going to an event where I can meet various kinky people in a nearby area. But I don’t know what to expect or even if I’ll like going. How will I know when or if I’m ready to go?

Many thanks, Anonymouse

Dear Anonymouse,

Opening the door to a new experience is certainly one of the scariest things for us to do. First, let me tell you that your fears are justified. Going to an event like this, especially for the first time, can be as scary as bungee jumping or skydiving for the first time. But the reward can also be just as good. Whether or not you’ll like it is all a matter of preparation, and building up the guts to just go for it.

To be properly prepared, you should first research this event, though I’m sure you’ve already done this. It’s important to know things like: who will be there, does this event happen regularly, and are there any negative reviews about it? It also helps to remember that you’re under no obligation to participate at an event such as this. It’s often recommended for people who visit for the first time to simply observe. Spend your first time watching what goes on, and learn what it’s like. Don’t worry about getting involved, and don’t be afraid to say ‘no, thank you’ if someone asks you to join in. They won’t be insulted, or at least shouldn’t. Hopefully, keeping this in mind will make it just a little less scary.

Building up the guts is a bit trickier to do, as there’s not much I can say to help you do this. Knowing if you should go comes down to how much you would like to. Does the event excite you as much as it scares you? Do you think it would be easier to do this in the future, or just as difficult? Will you have many more opportunities to try again, or would it be harder to even have the option in the future? Some of us can wait so long, the opportunity to do something like this is gone completely. When you’ll be ready is still ultimately up to you, but if it the thought of it excites you and scares you, it’s probably worth doing.

If you do go, I hope your experience is a good one. You deserve to enjoy everything you want to enjoy.


If you have a question about sex, sexuality, or the erotica genre you’d like submitted to Dear Charlton, you can send it to me through my Contact page. I promise to get to it as quickly as I can.

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