As far as huge events go, probably Leather and Leis on the big island & one or more of the east coast Dark Odyssey events. Other than those I stick to private parties that my friends or myself put on.
I am curious and interested in exploring my BDSM side. Are these events often open to guys like me? Do you have any suggestions? Or is it best that I first start by finding a provider and letting her know I am new and curious?
I took a submissive to Dark Odyssey Fusion a couple of years ago. And have heard good things about their Summer Camp and Winter Fire events. If you're taking a slave, I'd recommend Winter Fire (coming up mid-February) because it's based in a hotel rather than a campground with multi-person cabins, so you have more control over who your slave interacts with.
I recently found, on Fetlife, a swingers club in NYC that allows single men to attend.
I went a few times, and will return. I have a few women friends who are interested in going, so I will be returning with a date at times, and alone at times.
Though, if I have a date available, we may check out one of the couples-only places. Checkmate most likely
I've attended DomCon L.A. every year for the last few years and intend to do so again this year. Between the public play parties Friday and Saturday evenings held at a spacious local dungeon, the panels and demonstrations, and the private play sessions I've occasionally had the pleasure of participating in, it's become my must-attend "BDSM event." It's usually well-attended by Doms, subs, switches and is a good way for newbies to get their feet wet.
I found this pretty nifty calendar of BDSM events that others might enjoy. In terms of an "OMG - There is so much kink in one place!" experience, Thunder in the Mountains in Denver in July has the largest play space (I believe) of any event, and some fantastic guest speakers. (Love me some Midori.) Imagine a very large convention center space filled with tons of dungeon furniture and all types of play and everyone is doing their scenes at the same time. It's insane.
The event you attend might depend a little bit on how heterosexual or pansexual you want it to be, how much play versus vendor versus classes at that event, and other factors. TES Fest and The Floating World are supposedly off-the-hook, but I can't personally vouch for those. Folsom Street in San Francisco in September has to be seen to be believed. If you just want to see attractive people in hot outfits, something like FetishCon in Tampa, FL or Montreal Fetish Weekend might be more your speed.
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