A Tale Of Two Strap-Ons: How I Finally Found The Perfect Strap-On After Years Of Mishaps

Strap-ons are kind of like the Goldilocks story.

3d Illustration. XXX neon sign.Photo by istock

I knew I wanted to have strap-on sex from the second I saw Shane f*ck Cherie Jaffe poolside in The L Word. That scene, along with the Jenny/Niki strap-on scene, changed my life. It gave visibility to the kind of sex I wanted to have!

Only I was 16 at the time and too much of a baby to go into a sex shop. I know, thinking about 16-year-olds having sex is gross but this is my essay and I’m allowed to be gross.

You know how every high school has that one kid that everyone asks for “bad” shit from?– alcohol, drugs, etc. Yeah, well in my hometown, that was this guy named Tre.* And in my case the “etc.” was a strap-on. Tre* didn’t talk much, always wore a hoodie, and was friends with every clique because of his connections.

I don’t know how he got the strap-on, but he delivered. He left it in my girlfriend’s locker after science class. I was shaking with excitement while we rode the bus home, just thinking of that pink dildo in her Jansport backpack. When we got into her room, I ripped open the box like a kid on Christmas. It was MASSIVE, and it intimidated the hell out of me. The wearer got a cute little butterfly-shaped vibrator in the harness. A bunch of utterly confusing straps hung from it. My girlfriend tried to put it on and I went hysterical. I laugh when I’m anxious—it’s a bad habit—but to see her fiddling with all the complicated straps, all while trying to keep a 9-inch pink sparkly dildo up was too much for me. Get yourself together, I urged myself. In the name of Shane and Cherie, stop laughing. We tried, but we were way too awkward and inexperienced to use it properly.

Super glad I’m not a baby dyke anymore.

A few years later, in college, I couldn’t rely on the town drug dealer to get me a strap-on, so I ventured out. I wasn’t even anxious to enter the sketchy Long Island sex shop because I was completely obsessed with my girlfriend and would do anything to please her. I didn’t know about queer-friendly sex shops so all I had was a creepy, windowless building next to my local mall. It was called “Cupid.”

I forced my super-shy, super-straight, super-supportive best friend to come with me. She cowered in a lingerie-filled corner while I worked up the guts to ask the man behind the counter to show me his finest strap on.

“Is this for use with a man or a woman?” he asked, raising an eyebrow.

“Woman,” I squeaked. Oh no, I thought. Now he’s gonna gay bash me.

“Well, in that case, you’ll want a semi-flexible one, so it doesn’t bump her cervix.”

Wait, what? Was this strange balding man in a Harley Davidson shirt an undercover feminist? He helped me pick a black 6.5-inch dildo that came with a heart shaped harness. Cute and affordable! (Pro tip: NEVER buy the harness and dildo combo. It may seem cheaper and easier but is always shitty quality.) Then he told me to make sure I “take care of my woman,” which was sort of weird but preferable to how badly the exchange could’ve turned out. I practically skipped out of there, almost forgetting my best friend, who was inconspicuously browsing for Kim K’s sex tape.

The first night my girlfriend and I used the strap-on was much better than my laughable high school experience. It was hot. We took turns. It was so sexy to me that we could switch roles so seamlessly. We took a break to order a pizza (it was true love) then went right back to the strap-on. In the dark, I reached for the lube. Like I said, it was hot. Like really hot. Like,”why is this burning so bad?” hot.

The next thing I knew my vagina was on FIRE. What the hell was going on? I grabbed the lube I had just put all over the dildo and read out loud: “TOY CLEANSER?!” I spent the rest of the night spreading my legs apart in the shower.

F*cking with the strap-on was successful (minus the toy cleanser incident) but getting the damn thing on was annoying AF. I felt like a baked ham when I’d pull the straps tight enough so that it wouldn’t slide off. It would loosen during sex, and eventually, the dildo would completely bend one way or another.  It took too long to put on, and only stayed perfect for a few minutes, then we’d have to break to readjust. (Told you the strap-on/harness combo packs suck.)

As the years and my strap-on experience wore on, sometimes the top, sometimes the bottom, this problem always remained: The goddam straps. This has been written about by lots of lesbians– it might be our number one struggle next to homophobia. It is awkward AF to be stepping into what looks like a torture device while your girl is just awkwardly sitting there. It’s overwhelming to have to meticulously strap yourself in when you’re so excited to get back in bed. The more you rush, the more you screw it up.

That’s when I did a little investigation. Lovehoney.com is lit, you guys. And their return policy is similar to Sephora’s aka how TF are they letting me return this? (But I’m happy about it). Their customer service is legit amazing.

I called them, told them my tale of strap-on woe, and they hooked me up with a few different choices. They were super informative, kind and patient. I ordered a RodeoH Open Back Crotchless Strap On Lace Harness Panty in purple and it is SO CUTE. Not only is it cute, it’s comfortable and NO BAKED HAM STRAPS. It slips on just like sexy underwear!

The hole for the dildo (may I recommend this one?) isn’t complicated. You just stick it in you’re ready to go. I’ve read so many pieces on ~connecting~ with your strap-on and I’ve always been like, really? But after this one, I get it. It feels super natural on my body because it is extra and lacey and sexy and girly like me. I feel comfortable physically so I  am mentally comfortable and in turn, down for whatever. It just feels right.

In conclusion, my dear queers, is that strap-ons are kinda like the Goldilocks story. You gotta try ones that are too big, too small, too tight, cheap, to find one that’s juuuuust right.

As someone who literally gives up on anything I’m not immediately good at, I can understand why strap-ons for beginners can be intimidating. But I’m telling you, after a few times, you’ll get it. And it’ll be super hot. Just be sure to separate your lube from your toy cleanser.