Somebody posed this question on an anonymous smut-related mailing list: “anyone know of a site explaining what would be a good strap-on dildo to buy, and tips and tricks on how to use it?” and other members on the list directed them to me! I love being a local answer gal for things like this. I thought I’d share the advice I gave here, too, but it is sex-related so I’ll hide it. Don’t click to read it unless you really want to hear - it’s not raunchy, but it is explicit.

The responses you’ve already gotten - Blowfish and Good Vibrations - are excellent suggestions. Another favorite of mine is Toys in Babeland. It’s important to remember that you’re not buying “a strap-on dildo” as such, you’re actually buying a dildo and a harness to put it in. They’re generally two separate products.

The harness I recommend the most is the Texas 2-Strap and the Terra Firma is a close second. These are often hard to manipulate if the wearer is pretty large, though, so I usually mention the Crown Harness as well because it’s designed for bigger bodies. All of these have straps that go around each leg, which I prefer because they’re more secure. If you want one that’s just got one strap (thong-style) go with the Thriller G. By the way, I don’t like synthetic (nylon) fabrics for harnesses. Backpack straps are also made out of nylon, and that’s what these sound like…the one time I used a synthetic harness, I couldn’t stop laughing because it sounded like a backpack bouncing along.

Dildos are hard to recommend because everybody wants something different…and so there are hundreds (if not thousands) of styles. Look through babeland.com, goodvibes.com, and blowfish.com for something you like. If you want a double dildo, I can’t recommend the Nexus (and its smaller cousin, Nexus Jr.) enough: they are designed to feel good for the person wearing the harness, too (most boomerang-style doubles just feel like they’re going to fall out). Just make sure that if you get a double, you get a harness that has the hole all the way through. I also recommend silicone over other materials: it’s safer, easier to clean, lasts longer, holds heat…there are a lot of reasons to use silicone dildos! (Price, unfortunately, is not one of them, but they’re worth the extra expense.)
So take a look around and pick out something you like. If all else fails, get a “kit” - the Bend Over Beginner set comes with everything you need.

Hope that helps!

I then realized that I hadn’t answered the question completely, so I posted a follow-up right away.

Whoops, sorry, you asked for tips and tricks on how to use it, too! Karlyn Lotney (Fairy Butch) has an excellent book called The Ultimate Guide to Strap-On Sex that I totally recommend getting. As for websites…well, that depends on what you want to do. TiB has a guide to sucking a strap-on but I don’t know of many sites that describe what else you can do. It’s basically an in-out thing, you know?

Oh, and for more tips on choosing a harness, check out TiB’s Harness Coach which answers more questions.

Update, December 2007: The new Share by Fun Factory might be a good alternative to the Nexus. It looks pretty similar from what I can tell, and it gets good reviews, though I haven’t tried it myself.