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Sex educator Zachary Zane shares 8 things he wished he knew before having anal sex
#Anal Play Advice#Butt-life

What I Wished I Knew Before My First Time Having Anal Sex

Last Updated: Jan 25, 2022 / By Zachary Zane

The first time I had anal sex was a mess. Not literally, thank God, but emotionally and spiritually, I was in shambles. Now I had topped (been the insertive anal partner) many times before with men, women, and nonbinary babes. The anal bottoms (receptive anal partners) I had sex with were pros. They made it look so damn easy. They were as clean as a whistle that you could eat every last part of their behind. (And guess what? I did!) They didn't tell me to slow down or to use more lube. They just took it, like goddamn champions.

That's why I thought being the bottom would be a walk in the park. I was sorely mistaken (pun intended).

First-time anal sex as a bottom

The first time I had anal sex as the bottom, I was 23. It was with this man I had been dating, and I trusted him. The entire time we were having sex, I kept asking, "Am I pooping on you?" He kept saying "No," until, frustrated, he shouted, "If you poop, you poop! Stop asking!"

When I tell you I did not enjoy the experience, I did not enjoy the experience. I was in pain. I felt bloated. And I didn't feel any of the euphoric pleasure that I thought one was supposed to experience from anal and prostate stimulation. After the experience, I figured that being a bottom wasn't for me. And I was okay with it!

That was until my next partner. She was really into anal play on guys and told me I had gone about it all wrong. With her help and expertise, I tried anal play again, and finally, then, I understood what all the fuss was about. *Cue sexual ecstasy*

Now, I am a seasoned anal queen who loves butt stuff. I put anything and everything up my rear whenever I get the chance (which has, sadly, been few and far between due to Ms. Rona).

8 Things I wish I knew before having anal sex

But it took me a while to reach this point, and I wish someone had sat me down and gave me advice before my first time bottoming. As they say, be the change you want to see in the world, so without further ado, here are eight things I wish I knew about anal sex before having it. These tips are primarily for bottoms, but I also include some tips for first-time tops.

1. It may feel like you're pooping, but you're not.

I briefly touch on this in the intro, but I honestly thought I was pooping the entire time he was penetrating me. It makes sense why I'd think that. Until that point, the only sensation I had experienced in my rectum is the passage of feces.

So I've associated the feelings with defecating. Just know that you are not actively popping while having anal sex! (LOL!) With time, you get used to the feeling and uncouple the pooping sensation from the act of sex.

You may feel like you're pooping or peeing when you have anal sex for the first time, but you're not

2. It may also feel like you're peeing, but you're not!

So many new sensations, am I right? If you have a prostate, it can push up against your bladder when stimulated, making you feel like you have to pee. If you have a penis and prostate, you may also be getting "milked", and ejaculate may ooze from your penis. (This is totally normal and healthy and a sign that the person who's touching your prostate is doing something right!)

Even if you don't have a prostate, it can still feel like you have to pee during sex. Again, this is due to incidental bladder pressure.

3. If you do poop, it isn't the end of the world.

I don't mean to keep focusing on feces, but as a sex writer and educator, I cannot tell you how many poop-related questions I get regarding anal, so I know it's necessary to address. If you poop, it is not the end of the world. Like at all. (FYI, you won't like poop, poop. It'll likely just be a little bit!)

Seeing poop is something you should learn to accept during first time anal play

I've had anal sex as both the top and bottom thousands of times. I have pooped on and been pooped on more times than I can count. It's all part of the experience, baby! You have to expect to get a little dirty when you're rolling around in the mud.

If your partner shames you for not being pristine, they're the asshole here—not your asshole! (And odds are, they've never had anything inside of their anus. Otherwise, they would know "shit happens," and they wouldn't be rude about it!) Seriously though, if a partner shames you for not being clean, break up with them! They suck! (Oh, and for tips on how to anal douche before having sex, check out this anal hygiene guide!)

4. Use more lube.

I'm imagining the famous SNL sketch starring Christopher Walken where he says "more cowbell," but instead, he's saying, "more lube." Use as much lube as goddamn possible. It should be everywhere by the time you're done. Your apartment should turn into a slip-n-slide.

There is no such thing as too much lube when it comes to anal sex

It's also not a bad idea to get a lube applicator (AKA lube shooter), so the lube can get up inside your rectum. If you don't a lube applicator, put lube on your finger, and then insert your finger into your anus. Then apply more lube directly on the toy or penis.

If you're having sex with a silicone toy, you need to use a water-based lube as not to destroy the toy. Then you really need to reapply frequently because water-based lube dries out quickly. (Remember, the anus isn't self-lubricating!).

If you're using a penis, then definitely go ahead and use a more viscous silicone-based lube because it'll last longer and feel better! So tops, now you know to have silicone lube for anal sex, and you know to apply it abundantly.

5. Work your way up to bigger and better things.

Do not start by trying to insert a girthy 8-inch dildo inside your rear end. That is far too aggressive. Start with your pinky. Then work your way up to your middle finger, then two fingers, then toys, etc. You can, of course, practice by yourself before you ever try with a partner. It can also be nice to have a partner help you (with their fingers) your first time too! Here's everything you need to know on how to give an anal massage or how to get started with anal fingering.

Using an anal training kit can help you accommodate bigger toys or your partner's penis

You can also explore the use of an anal training kit if, say, you're working your way up to your partner's penis, and they're on the bigger side.

6. You're in no rush.

There have been times when it takes five solid minutes (which is a long-ass time during sex) before I can take the penis/dildo. I put in the tip and then have my partner pull out. We apply more lube. I breathe. I go ahead and try with their fingers this time. Then back to their penis. Take it out. Breathe. Repeat.

The most important tip when it comes to first time anal is to take it slow, whether you are the giver or receiver

Note that some folks—specifically men who've never had anything inside of them before—can be a little aggressive. Tell them to hold their damn horses! So this is now a note to tops— do not stick it in! Go slow. Be gentle. Check-in with your partner. Wait until your partner tells you they're ready for more before you fully insert yourself.

7. Careful with poppers.

Poppers, AKA alkyl nitrites, are often marketed at VHS cleaner yet can be found at your local sex shop and many bodegas. Poppers are commonly used during anal sex, especially in the gay male community. You ingest poppers by inhaling them, and they work by relaxing the smooth muscles in your body (including your anus). You also get a little head rush (for about 60 seconds), which some folks find very pleasurable during sex.

Avoid using poppers and numbing agents during anal sex

Many folks take poppers to take larger toys and penises. This is bad! If you can't take it without the poppers, then you shouldn't take it! The reason why? You man end up with more anal tears (fissures). It's also why you shouldn't take poppers with any anal numbing agents. You won't realize if you're in pain or are getting anal tissue tears until after the numbing agent has worn off.

Oh, and if you take Viagra (or another erectile dysfunction medication), you cannot, under any circumstances, use poppers during sex. There's a high risk of fainting, heart attack, and stroke (especially for older men) if you use Viagra and poppers simultaneously.

8. Anal sex feels incredible!

Hopefully, what I said didn't intimidate you or make you not want to have anal sex. Anal sex feels incredible regardless of your gender or sexual orientation. The physical sensations are divine and can lead to stronger orgasms, not to mention there's something intimate about having someone (or something) inside you.

Anal sex is for everybody and feels absolutely incredible

So go out there and put some things up your butt! If you have a partner, surprised them with some Valentine's Day anal. It's the best surprise gift to your partner!


Found this article on first time anal useful? Check out our most popular guides on analingus techniques, anal sex positions, and anal training. Not a fan of reading? Be sure to watch our Butt Stuff Basics Video Series for the best tips on booty play.

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