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How To Prepare For Anal Sex Once You Decide You're Ready

One of my earliest bonding experiences with my best friend Jane is when I made her pick me up at my ex-boyfriend's house at 3 a.m. our freshman year of college... after I had anal sex for the first time. I was absolutely freaking out and also in a significant amount of pain. Sex itself is more or less intuitive, not to mention there are tons of movies, magazines, and older, wilder friends who basically tell you how to do it at some point before you actually pop your cherry.

However, no one really sits you down and explains how to prepare for anal sex (and how to have it). This was much to my detriment, because the first time I had it, I didn't use lube and ended up kind of sh*tting on my boyfriend's dick (and needing my best friend pick me up at 3 a.m.) Sorry, internet. I'm just here to report the facts.

My first butt sex experience was clearly not great. But yours deserves to be — and it can, if you prepare correctly. So I asked Dr. Martha Lee, clinical sexologist and author of Love, Sex and Everything In Between and Orgasmic Yoga, about the ins and outs of anal sex, like how to prep for it.

"One of the most pleasurable places in the human body is the anus," Dr. Lee explains. "Our anus is full of nerve endings. Unfortunately, most of us are blocked to some degree from enjoying these delightful tissues because of personal and cultural shame."

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The first step for safe anal sex, according to Dr. Lee, is to adopt a healthy attitude and release any stigmas or fears you might associate with the act (after you've made sure you've gone to the bathroom first).

She says, "Let go of judgment or self-judgment. Anal sex is not bad for health if performed consciously. Anal sex can spread sexually transmitted infections more easily, but if you are in a long-term, monogamous relationship, the risk is how trace amounts of faeces may cause infection."

Additionally, she suggests that before immediately going all the way, you might want to try out some ways to ease yourself into the idea of anal sex. "Anal sex is different from anal play. With anal play, there need not be penetration into the anus — just massage externally and there can be great pleasure. Anal play can be used during foreplay or as part of your all play," she explains.

There are also great sex toys to facilitate anal play, such as butt plugs, anal beads, or even anal vibrators. But if you want to go all the way and actually have anal penetration, what should you do? Here are some tips.

1. Go Slowly

Kayla Snell

Butt sex is not something you can just rush in to. For lack of better phrasing, you need to take your time so you can loosen up a bit.

"Anal sex hurts if you are doing it wrong," says Dr. Lee. "The best way to go about anal play is slowly – obviously after you have had consent to proceed. If your partner is unable to relax sufficiently so that you can penetrate their anus with one then two of your fingers, then obviously, they are not ready for your penis to enter."

So when it comes to anal sex, slow and steady wins the race.

2. Be Aroused

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Arousal, as in regular sex, is integral to anal sex as well. It will get you comfortable and lubricated for penetration.

So how do you make sure you're aroused before going all in? Dr. Lee says that "you can begin stimulating your partner's anus with your finger while performing oral sex on them." Once you get comfortable with your partner's fingers, you can then move on to something more substantial than fingers — like a ginormous penis, for example.

3. Stay Smooth

Mauro Grigollo

No glove, no love with anal sex. But protection doesn't only have to do with STDs. Dr. Lee says, "You may wish to cover your finger with a finger cot, condom, or wear vinyl (not gardening) gloves for added smoothness."

This part is for the initial anal play, although you will definitely also want to wear a condom during penetration. But remember, no gardening gloves, OK!!!

4. Lube Up

Take it from me: Lubricant is incredibly important for anal sex. "Loose and lubed" is what I always say when it comes to a pleasurable butt sex experience!

"Besides applying lots of lubricant, I would advocate the importance of massaging the entrance of the anus until you can feel the external anal sphincter relaxing," says. Dr. Lee.

5. Find The Right Position

Finally, find an anal sex position that works for you. Dr. Lee says, "If you want to move onto penile penetration, the most comfortable position would be the side-by-side position. This prevents deep penetration and allows for more controlled movements."

So to maximize pleasure during anal penetration, try the spooning position. Additionally, your partner can stimulate your clitoris with their hand or a toy during sex, so you get double the pleasure and double the fun.

And don't forget the most important tip: Stay safe and clean. Dr. Lee says, "If you put your penis or fingers in or around the anus of a vagina owner, you cannot simply revert to their vagina afterward."

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