Sat. Oct 23rd, 2021

I’m a 25-year-old sex and wellness writer with a hearty (nay, adventurous) collection of sex toys, and yet I’ve never been able to make myself orgasm. I’ve masturbated with my hand, the cult-favorite Magic Wand, a crystal dildo, the clit-stimulating Satisfyer Pro Plus Vibration, a G-spot vibrator (or four), and while watching porn and reading erotica. But while I’m able to make myself feel good, I’ve never been able to take myself to the O-zone.

You’re probably wondering if I’ve ever orgasmed with a partner. I have. My first orgasm ever happened a few months ago during vaginal penetration with my partner of 18 months. And it happened a handful of times after that initial, um, release.

But now that I’m single again, I’m about as O-free as, well, a Disney movie. Honestly, I assumed that after orgasming with my partner, I’d be able to get there again on my own, but still nope.

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My lifelong, not-a-medical-professional hypothesis for why I have a hard time coming is that in high school before I was sexually active I was on anti-anxiety medication for few months—meds that have a rep for messing with libido and sexual function. So when Alicia Sinclair, sex educator and CEO of b-Vibe, told me, “Women often report that their ability to enjoy anal sex and climax through anal stimulation is less affected by medication,” I decided to bring a second hole into my solo-time.

Without getting into too much detail, I’d played with my partner's butt (shoutout to Lelo’s Hugo prostate massager), but beyond a lick and flick here and there, my butt never attended the party. Sinclair convinced me to get the party started.

While I have dildos in every shape and color (including rainbow!), Sinclair informed me that when it comes to butt play, you want to find something with a flared base. “Unlike your vagina, which stops at your cervix, your anus keeps going all the way into your digestive system, which is why you want a structure that keeps the plug from getting lost inside you.” Yikes.

Also, at risk of sounding like a size queen, all of my dildos are longer than five inches, which TBH intimidated the eff out of my peach.

I decided now wasn’t a time to be stingy. While I usually prefer sex toys made of glass or steel because I like the heft, Sinclair says silicone products are better for newbies, so I bought an “anal training kit” complete with three silicone butt plugs at increasing sizes (three, four, and five inches) and also a vibrating butt plug made of silicone (because I’m an overachiever).

Then, I stocked up on more of my favorite silicone-based lube. Why lube and why silicone-based? Not to over-hype it, but in my experience lube can take your sex life from a Charlotte to a Samantha in 10 seconds flat—or however long it takes to dig through your night table and flip open the top of the bottle.

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Plus, your butt simply doesn't self-lubricate. “It’s imperative that you have some lube on hand to facilitate a smooth experience," says clinical sexologist Megan Stubbs. "I would recommend applying lubricant to both the toy and to your anus."

I decided a silicone-based lube would be best because Sinclair suggested that the first time I use the butt plug I do it in the shower, and I know from ~experience~ that water-based lube washes off in the shower, while a silicone-based lube has more staying power.

While Sinclair said I didn’t need to worry about making a mess (because I had to ask if poop was going to be an issue) and could play in my bed, she says showers are best for beginners: “It’s warm, which will help you relax, and there’s more flexibility for positions.”

Fast forward to a lovely January morning at the ripe hour of 10 a.m. when I knew my roommate would be gone for at least two hours—and also when I needed a shower (#multitasking). I (unironically) lit my favorite Boy Smell Candle, moved my speakers into the bathroom, and set up shop on the counter. I arranged my butt plugs from smallest to largest and tested the settings of my vibrating toy to get a sense of how it would feel (on my hand, it felt the same as any other low-powered vibe). Then, I stripped down and stepped in the shower, tube of lube in hand.

RELATED: 5 Tips That’ll Make the Shower Your New Favorite Place to Have Sex

I closed my eyes and hummed along to The Weeknd, my self-pleasure soundtrack of choice. After sudsing up my hands, I ran them along my body (because, Team Foreplay) and remembered to breathe, thanks to Sinclair's advice. When I was thoroughly immersed in my go-to James Dean fantasy, I lubed up and got down to business.

Honestly, it wasn’t super intuitive. First, I tried standing with my feet shoulder-width apart, bending forward and trying to insert the three-incher almost as if I was inserting a tampon. But getting the plug at a 45-degree angle toward my belly button as Sinclair had instructed wasn’t working.

I tried again, this time with my hand behind my back. Success! Once the tip of the plug made contact with my anus, I made small circles, almost rocking it side to side against the hole. It took about two minutes of wiggling to get the plug all the way in.

How’d it feel? OK. Not painful. The best way I can describe it is that I felt full. And “stuffed” was the only sensation I felt—until I started touching my clit, that is. As I touched myself with the butt plug in place, it felt like the ring of nerves around my anus and the nerves in my clit were having a full-blown, sexy conversation. It was as if my clit was more sensitive because of the plug. I think how taboo the whole setup felt turned me on too. Here I was, a woman taking responsibility for her pleasure, and with a butt plug, nonetheless.

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I wish I could tell you the butt plug brought me oodles of orgasms. It didn’t. After about 15 minutes, I added a dollop of lube to my finger, which I teased around the lip of the plug, and wriggled it out. Because I know you're probably wondering: There was no fecal residue on the plug, and my anus returned to its normal shape roughly five seconds after. (“The anal sphincter will always return to its normal size,” Sinclair says.)

So, no I didn’t come with a butt plug either. But overall, I’d call the whole experiment a success. While I can’t promise I’ll take my butt plug to the bathroom every time my roommate bops out for an errand, it is something I can see myself experimenting with again—especially because I haven’t tried the vibrating plug yet. And I'd certainly be open to finding a new partner who will want to give me some oral while I use that plug. Because that, my friends, is ultimate #bootygoals.

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