Ask Dirty Lola: Advice From An Award-Winning Sexpert

My girlfriend and I are planning on buying a strap-on for the first time. We’re stuck on what we really need to buy and what kind we should get. Any tips for a first timer?

Hey, friend! I have just what you need.

Think of me as your Fairy Sex Toy Godmother. Baby’s first strap-on is a big deal, and it’s totally normal to feel overwhelmed. A quick Google search will drop you into a sea of options with zero guidance—but don’t worry, I’ve got you. A strap-on consists of three parts: a harness, an O-ring, and a dildo. (Unless you’re going strapless, but that’s a black belt move we’ll save for another time.)

If you can, shop in person—preferably at a boutique with testers and knowledgeable staff. I love Shag in Williamsburg and Please in South Slope. It’s way easier (and way more fun) than shopping online. Make it a date night and get hands-on! If you prefer shopping online, New York Toy Collective is queer-owned magic, AND they sell a strap-on Starter Kit!

Starting with the harness. There are two basic types: brief-style and jock-style. Brief-style harnesses look, feel, and are sized like underwear. They are also machine washable, and can be worn under clothes. They’re comfy but can be spendy and usually come with a fixed O-ring, which limits what size dildos you can use.

Jock-style harnesses come in various materials, are more adjustable (GREAT for sharing!), and often come with interchangeable O-rings—perfect for accommodating dildos of all sizes (size queens, rejoice!).

Once you’ve picked your harness, choosing a dildo is a piece of cake. There are tons of body safe options out there that come in various sizes, colors, shapes, and um…..species. Hey, if you want to play alien impregnation, I’m happy to make your dreams come true. Pro tip: the person being penetrated should make the final
pick. If it fits, they’ll sit.

Welcome to the wonderful world of strap-ons!

Dirty Lola is an award-winning sexpert, edutainer, and longtime voice in the sex positive community. With over 11 years of experience working in sex shops, she’s helped thousands navigate toys, turn-ons, and the beautifully messy world of pleasure. She’s hosted live Q&A shows, appeared on podcasts, Netflix, and HBO series, and been featured in New York Magazine, Vice, and Allure. Find her at dirtylola.co and @dirtylola.

This column is not a consultation with a licensed mental health professional and should in no way be construed as such or as a substitute for such consultation. Anyone with issues or concerns should personally seek the advice of a licensed therapist or counselor.