A few years ago, I tried anal sex for the first time. It was with my (now) ex-boyfriend who was a self-proclaimed “anal daddy” (let’s agree from here on out to not talk about my horrible taste in men).
We grabbed Taco Bell, headed to his place, drank some beers, and then banged. Now, I know what you’re thinking: Taco Bell? And anal?! Yup, and yup. (PSA: If you know anything about the digestive system, don’t try anal sex right after you’ve housed a chicken and cheese burrito.)
We started with vaginal penetration, then he slipped a finger in my butt. Now, I thought that anyone who named themselves “anal daddy” would, you know, have an idea of how to properly engage in anal sex. But despite knowing my hesitation, he went way too hard—like, as if we were shooting a porn scene. I actually felt like I was dying, so I told him to stop. He did and, hooray, no brown sightings.
But then, he did the unthinkable: He double dipped, AKA went right back into my vag without cleaning himself off. I was so hyper-focused from the shock and pain from him going too hard, and he immediately went right back into the V with no hesitation, that I unfortunately wasn’t in the right headspace/didn’t have time to stop him. Near fatal mistake.
A few days later, I contracted a UTI, which turned into a severe kidney infection, and I had to pass kidney stones that took nearly four months to heal. So, yeah, you could say that was a horrible first-time anal experience for me.
Unfortunately, my emotional healing is still in progress—but this article isn’t about me. It’s about horrible anal experiences in general: The poop stories, the accidental ‘wrong hole’ tales, painful tears, crossed boundaries, etc. The list unfortunately goes on and on.
If any of this sounds familiar, first off, I’m sorry. But I’m here to tell you that recovering from a first-time-anal-experience-gone-wrong is possible (for you and me both). Here’s seven tips from the pros who will help us get through it:
1. Forgive yourself and/or your partner.
First off, “acknowledge your experience, give yourself permission to heal, and don’t blame yourself for not knowing something, doing something incorrectly, or trying something that didn’t end well,” says Alicia Sinclair, certified sex educator and founder of b-Vibe.
Unfortunately, the reason why you may not know what to expect is because, hi, our sex-ed experience is pure trash and didn’t exactly teach us how to properly engage in butt-play.
2. Educate yourself on the “how-to” behind safe, healthy, FUN, anal play.
Anal sex should *always* feel pleasurable before, during, and after the experience for both the giver AND the receiver. “It might seem boring, but re-education about how to prepare and properly treat our bodies during anal play will highly empower your experience,” says Sinclair. “Plus, you’ll probably learn a few enjoyable, new tricks you didn’t even know about.” (Here are 11 easy tips to prep yourself for anal play).
For one, use condoms. They’ll help protect you from things like STIs and HIV. Secondly, stock up on the lube. It truly just makes everything better. Lastly, learn from my mistake: If you’re going to be double-dipping, it’s okay to go from the vag to anus—but never, and I cannot stress this enough, go from anal to vaginal intercourse.
3. Reflect on your negative experience(s).
Was the issue an accident? If so, “discuss what happened with your partner. Share your fears and how you want them to respond if things don’t turn out the way you’re hoping next time,” says Erica Zajac, LCSW, sex positive therapist with Brooklyn Minds.
Did your partner intentionally disregard boundaries, harm you, or lie to you? Major red flag vibes. Consider not having sex with them anymore, or dumping their ass completely. I broke up with my ex after he didn’t GAF that I was in an urgent care office to treat my third infection flare-up. You should too.
4. Experiment and play by yourself first.
NO RUSH, but when you’re down to re-intro yourself to anal play again, start by playing with yourself. Try different toys and plugs of varying girth and size with lots and lots of lube to understand your comfort levels. Trust: It’s much easier to tell your partner what you like, don’t like, and are comfortable doing if you test out the waters first.
5. Communicate consent and boundaries.
When you’re 100 percent ready for partner play again, discuss safe words and make limits clear. Don’t forget that you can always renegotiate and establish new boundaries, reminds Sinclair. And most importantly, the key to any safe, healthy, sexual experience is consent. “If it’s not an enthusiastic ‘FUCK YES,’ then it’s a ‘FUCK NO,'” says Zajac.
6. Don’t try to do too much too soon.
Whatever you do, slowwwlyyy re-introduce anal play with lots of check-ins along the way. Have realistic expectations—meaning, even if the next time isn’t as bad, you may discover you simply don’t like anal sex. And that’s totes fine. Luckily for you, there are a billion other things to do in the bedroom.
7. Consider therapy.
For those struggling with an experience, therapy is always an option—especially if what happened was highly traumatic. “It’s really helpful to process those emotions, especially if you do want anal play to be a part of your sexual diet,” says Sinclair. “Even though humans are resilient and strong, we still need support and self-care to overcome trauma and to have pleasurable sex lives beyond negative sexual experiences.”
Regardless of what happened that turned you off from anal play, rest assured that you can recover from negative first-time experiences—and maybe even enjoy it someday. Just do yourself a solid and never engage with someone who calls themselves “anal daddy.”
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