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10 Things All New Bottoms Should Know

how to bottom without pain

I was pretty young when I started out bottoming and I remember being absolutely terrified the first time I actually took the plunge...

You name the insecurity and I had it, let me tell you. All sorts of negative bullshit was swirling in my head.

"What if it hurts too much and I can't do it?", "Am I clean down there?", "What if I'm a bad fuck?", and all sorts of other weird insecurities about my masculinity and power dynamics.

I was a mess, plain and simple.

As I grew up a bit,  got a few more lays under my belt, and learned to listen to my more experienced partners and friends, I learned that confusion and insecurity are pretty much par for the course when it comes to first time anal. I also learned that many of my insecurities were actually well-founded and that there are ways to work around these little problems so I wouldn't have to worry anymore.

For instance, looking back, I probably was a bad fuck, it actually did turn out to be too painful for me to go through with anal the first time, I certainly wasn't clean enough down there,  and I absolutely disappointed my partner.

I've come a long way since then and I've learned a lot but I can't help but feel that if I knew then what I know now, things would have been a lot easier for me early on in my bottoming adventure.

Which brings us to the purpose of this article and how I hope that by writing this piece, others won't have to fall into the same traps that I did.

So, if you're are an anal first-timer or just a guy who's looking to up their game by learning from the mistakes of a guy who learned the hard way, this list is for you!

Here are the 10 things I wish I would have known when I was just a newbie bottom starting out.

10. Clean = Confident

clean = confident

It's a simple fact that you fuck like a champ if you feel like one. If you go into a bottoming situation with all sorts of concerns about how you smell, whether you are clean enough downtown, or whether your pubes are trimmed and on point, you're going to be tense and distracted. This means you'll probably be in for a rough ride and a disappointed partner.

If you're all stressed, you're muscles have a tendency to tense up. This is exactly what you don't  want. A tense hole is going to make penetration much more unpleasant than it needs to be. So, what's to be done?

First things first, you're going to want to make sure your nails are nice and trim and, preferably, filed down. They're going to get up to all sorts of naughty business poking around in sensitive areas and nobody wants a scratched asshole.

You're also going to want to make sure that your pubes are well-groomed. Do whatever makes you feel sexiest.  If you're the kind of guy who doesn't really give a damn about how your pubes look, a good rule of thumb is to groom you crotch the way you'd like to see your partner's groomed.

Lastly, we should address the biggest hygiene question of all: poop. Though it's not exactly dinner table conversation, it is an unfortunate reality of anal sex and it needs to be discussed. 

The most important thing for newbie bottoms to know, is that it's bound to happen eventually and you shouldn't take it too hard.No matter how careful you are, no matter how much you try to mitigate it, eventually there's going to be poop. Luckily, there are steps that can be taken to nearly eliminate the issue.

clean your ass before anal

First thing is how and what you eat. If you're planning on bottoming a lot or you just want to make your anal cleanliness regimen a whole lot easier, eat lots of fiber or take a supplement. Personally, I just eat a lot of healthy cereal with lots of fiber because I love cereal and that works for me. I have some friends who swear by supplements. However you do it, get some fiber in you, it'll really make things easier.

You're also going to want to be careful about what and when you eat if you are expecting a little anal play. Don't go out to the Chinese buffet or taco Tuesday and pig out if you think you're going to have a knock at your back door. Also, try not to eat for at least a few hours before that knock comes.

anal douche

Ergoflo Anal Douche

Finally, you're going to want to get yourself a nice anal douche kit. It's really the only way to get in there and make sure you're nice and clean. I recommend one that has a mechanism for preventing backflow. I use an Ergoflo Perfect Fit Extra because it's comfortable and clean.

9. Self-Exploration

self-exploration - anal

It's a good idea to poke around under the hood yourself before you let someone else do it. This is a safe way to explore and expand your limits without any of the pressure a partner can bring to the equation.

First of all, you're going to want to have some decent lube on hand. When it comes to anal play, less is never more where lube is concerned, seriously.

Pour lube

Pjur Analyse Me!

To get yourself started off, just lube up your hole and a finger and start to tease around your hole to loosen it up a bit. Actively try to relax your sphincter and experiment with ways to accomplish this. One good trick is to tense your hole up as tightly as possible just before you go in with your finger. This causes the sphincter to reflexively relax for a brief moment.

Since you read the first tip, I'm going to assume you're all nice and clean down there, so don't be afraid to bear down as if you were going to the bathroom to help open yourself up a bit. In short, do what you need to do to get relaxed. After you're comfortable with a single finger, try to work your way up to two or three. This is a good exercise to get your feet wet.



Once your comfortable with fingers, you might want to consider getting a dildo. Don't let your eyes be bigger than your appetite when it comes to choosing the size of your dildo. If you are the kind of guy who has a real tight hole, you might want to go for a slimmer, smaller model.

If you're confident enough that your going to be taking the show on the road anytime soon, you might consider a toy sized more like an average cock so you can prepare properly for the real deal.

Average Joe Dildo

Average Joe Dildo

If you really want a good way to work your way up, you might also try an anal stretching kit. These are really just a set of increasingly large sized butt plugs that are sold as a kit to help you increase your tolerance for size.

anal stretching
Whatever you decide, just be sure to work at your own pace and listen to your body. There is a difference between discomfort and pain- if it actually hurts, stop it.

8. When It's Time To Get Down With A Partner, Be Yourself.

Be yourself while bottoming

I realize how trite it might sound to offer the advice of being yourself, but sometimes things are cliche for a reason. If you go into a sexual encounter trying to be something you're not, you won't be in the right head-space to ensure both you and your partner are fully connected sexually.

Don't go into your encounters with a top with the idea that you're going to channel some porn star persona, or try to live up to the perceived expectations of others. If you do, you're going to end up being distracted and tense. You're partner will definitely feel this.

7. Communicating Your Needs Is A Major Turn-On

communication during anal sex

In my experience, good tops are extremely invested in how their bottoms feel and are turned on the most by turning on their partners. If you just let go and do what comes naturally you're top is going to really like it. Don't be afraid to be bossy. If you tell your top what you like they will have a better time knowing you are getting what you need too. What may seem like selfishness at first is actually a major turn on for tops. Tell them what you actually want and you'll both be happier for it!

don't be afraid to be bossy during anal

6. Ease Into It

ease into anal play to avoid pain

If you're new to anal, or your hole hasn't seen action for awhile, chances are you're going to be a little tight down there. Be sure to incorporate some light anal play into your foreplay before you dive into the main event.

As always, use lots of lube and start off slow. For me, a rimjob is an excellent way to get my hole ready for penetration, but not all guys are willing to do that. If your guy isn't into rimjobs, try a little finger play or break out a slimmer toy. I find having a guy work my hole over with a slim, vibrating toy is an almost foolproof way to loosen up.

5. Get Savage!

get savage during anal play

If a picture is worth a thousand words, a genuine moan is worth a thousand pictures. Which is to say, yelling "Fuck me, daddy!", or something along those lines might be hot but a really primal moan of pure pleasure scratches an instinctive itch for your top that words could never even reach.

A lot of the pleasure of topping comes from the boost your ego gets when you are the one responsible for bringing your bottom to such a primal, ecstatic state. A top never feels better about a sexual encounter than when the bottom is left panting and exhausted with pleasure.

get savage during anal

Letting yourself go and descending into an animal frenzy of biting, scratching, and moaning will send a very clear message to your top that he is like a god of sex. It's also an incredibly cathartic experience to let go of yourself and just be a wild animal doing what wild animals do, even if it's only for a little bit.

4. Really Get In The Game

get in the game - bottom without pain

A common misconception about bottoming is that it is a passive activity. This is only true if you want to be a bad lay. Along the same line as the last tip, using non-verbal cues is a great way to send a message to your top that you like what they are doing. Push back into his thrust, reach back and pull him in, jerk your dick while he pounds you, whatever comes natural, but whatever you do, don't just lie there like a Real Doll. Let him know, under no uncertain terms, that you're really digging what he's up to and your guy will definitely be coming back for more.

3. Keep In Fighting Shape

anal training - bottom without pain

Sadly, we all experience a sexual drought from time to time. An unfortunate fact of anal sex is that your hole will tighten up again if it's not regularly penetrated. This can lead to performance issues when we finally do get back into the saddle.


So, when you're experiencing a drought, try to keep up on your anal game during your solo sessions. Break out that dildo, toss in a plug from time to time, whatever.

anal exploration kit

Anal Fantasy Collection Anal Adventure Kit

Just make sure your hole doesn't tighten back up or you'll practically be back to square one when you jump back in the sack. You won't be able to fuck like a champ unless you train like a champ!


anal stretching and dildos to keep in shape

2. Know Your Limits And Be Safe

play it safe your anal bottoming

Anal sex isn't completely risk free. Your anal cavity and intestinal walls are extremely sensitive and easily injured. That's why it's incredibly important to listen to your body and pay attention to the warning signs that something is not right. Never push your limits to the breaking point, things will end very poorly. If you are experiencing pain or bleeding, no matter how minor, stop what you are doing immediately and figure out another way to get each other off.

1. You Have The Final Say Over Your Body

You are in control when bottoming

Being a better bottom isn't just about making your partner happy, you have to consider yourself as well. Never feel pressured into doing anything you find distasteful, uncomfortable, or dangerous just to please some dude. You are the sole and final arbiter of what happens to your body and if you feel like you are approaching a line you don't want to cross, you should always reserve the right to call the whole thing off.

If your partner is put off by that, they were probably a shitty partner to begin with. If they can't respect your agency, they don't respect you. Who wants to fuck a guy who doesn't respect them?


In the end, we all have to go through the trials of sexual self-discovery. No amount of advice will save you from learning a few things the hard way but it is my sincere hope that this little article will help you navigate the whole messy adventure a little more safely and sanely. When things go bad, like they sometimes do, just keep a level head, learn from your mistakes, and never repeat them. When things go good, enjoy it. Ultimately, that's the only advice that's worth a damn.

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