How to Make Bottoming Less Painful?

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How can I make bottoming hurt less? How do I get ready to bottom? Is Mucilin good for bottoming?

By Dr.Love, Last medically reviewed by Dr.Deyn on May 7, 2021. Updated 25 February 2024

How to Make Bottoming Less Hurt And Safer

I am writing this because once @iamgiselerafael asked me "Doctor Deyn, How to make bottoming less painful?", which, I thought was cute of her (because I thought everyone knew how to bottom.) But when I talked to her more about it I reallized that bottoming is problematic and worrisome for a lot of people. Also, according to my experiences, I have met and helped many guys bottom successfully, even though somebody has a tight hole, with the right way of doing it, bottoming is pleasurable and enjoyable. Also recently (because of COVID?), many of my boys are not having sex so they started to learn to give themselves pleasure besides jerking off and one of my friends is asking to know more about bottoming just because people are asking to top him and he always said "NO" but it made him feels bad because he wants his sex partner to be happy/satisfied.

Bottoming is to get fucked in the ass, yes. But it is much more than that! When you are young you may just shove it in or you may not prepare much. But to be a GOOD bottom, bottoming is more work than fun but that's the work we have to do to have our kind of fun (plus pleasure and satisfaction.)

How Do I Get Ready To Bottom?

Bottoming can happen anywhere, at any time. But if you suspect the opportunity might present itself ahead of time, you can improve the experience with a little preparation, both emotionally and physically.
One of the best ways to relieve whatever stress or performance anxiety you might have is to know your HIV status ahead of time. You can get tested at a free clinic in most major cities or take a mail-in self-test (which is often offered free, too — check out the CDC’s guide to self-testing here). Communicate openly about your status, and if your partner doesn’t know their own, let them know that you’re looking forward to playing once they do. Part of your conversation should include your plans for condom use. Consider starting PrEP as well, a daily or event-based medication that can prevent new HIV infections in those who are HIV-negative.
The communication doesn’t stop there. If you’ve bottomed before, you know that it can be a delicate process, and you’ll want to make sure you talk a bit ahead of time about what you like or what you want to try. Make sure your partner understands your boundaries and is OK with stopping if either of you needs to take a break.
Talking about your hard limits will prevent any unpleasant surprises. And talking about your fantasies can be a fun way to get in the mood! Don’t be afraid to go into detail about what you think would be fun to try, from positions to accessories to role-play.
If possible, you’ll want to practice a little extra hygiene as well. Anal sex can present the possibility of a show-stopping mess, and many people prefer to clean themselves out with a douche (which cleans the immediate area inside your butt) or an enema (which goes deeper).
Just don’t make a frequent habit of this — once a week is probably about right — because you can irritate your tissues if you’re constantly washing yourself out. If you’re doing frequent deep-cleans and you’re feeling more pain or internal friction than you like, it’s possible you’ve gone a little too tidy.

Where can I get more knowledge to prepare to bottom?

I have written a clear guide about bottoming.

What Should I Eat Before Bottoming?

You shouldn't be eating!! I AM KIDDING! LOL Too much douching can be harmful, but fortunately, you can tweak your diet so that you can be more prepared for action!

In general, fiber, raw vegetables, fruit, and whole wheat foods are best for maintaining tidy bottoms. Avoid greasy foods, red meat, and dairy, which can cause problems for the lactose-intolerant; alcohol, which can dehydrate you; and sugary snacks.

Bottom-friendly snacks include popcorn, raw nuts, berries, and lots and lots of water. Brown rice is helpful for many people, as are lentils and chickpeas. (But avoid legumes that can cause gassiness, unless that’s what you want.) Yogurt can help maintain proper gut biology.

If you’re having trouble getting enough fiber in your diet, a fiber supplement, like Metamucil, can be a good way to firm up your stool and make preparation easier. Some products, like Pure For Men, market themselves as fiber specifically for gay men or for bottoming — but they’re the same thing as psyllium husk capsules or other kinds of fiber supplements, just more expensive.

Everyone’s body is different, so you should pay attention to what you eat and the effect that it has on you. Remember, there’s always a chance of a little mess. That’s just a fact of life. Try not to worry about it too much; the more you relax, the more you’ll enjoy yourself.

What Kind of Lube is Best for Bottoming?

When it comes to supplies, be sure there are lube and condoms available. It doesn’t hurt to have some towels handy to clean up any mess. You should also try different kinds of lube to see what you and your partner like best. Consider a water-based lubricant if you’re planning to use toys made of various materials (bonus: less risk of staining). Silicone-based lube shouldn’t be combined with silicone toys, but many people find that it lasts longer. You can also get lubricants that are oil-based if you’re a fan of coconut oil — but remember that oil-based lube shouldn’t be used with condoms.

Pay attention to the lube’s thickness as well. Some folks like a watery, runny consistency, while others prefer something more thick and spreadable. Try out different varieties to see what works best. As you’re zeroing in on your preferred ingredients, check to see if there are any infusions, like jojoba, that are good for your skin.

Some kinds of lube have a numbing agent, but that’s generally not a great idea to use — you should be able to feel pain so you know if something’s wrong. Not to mention, you might experience even more pain once the numbing agent wears off.

You might also consider using a “shooter,” or a device that injects lube into your body without making a mess on your hands and sheets. That can speed clean up afterwards, and also ensure that you’ve got enough slipperiness inside.

How Can I Practice Bottoming?

If you want to impress your partner, you might want to rehearse when you’re apart so that you can bottom like a pro next time. The more you practice, the easier bottoming gets. (Also it can just be fun to go solo!)

For that, you’ll want some lube and some private time. You can use your fingers or a toy that’s made for insertion, but fingers will give you the flexibility to get to know your body. You have two sphincters in your butt — external, which you can control, and internal, which you can’t — and they both need to be relaxed before you go to town.

It’s best not to grab random objects and practice with those because they could cause irritation or injury. Instead, opt for toys that have graduated sizes so you can find the best fit for you.

Start by grabbing some lube — silicone-based will be long-lasting and slick, but should not be used with silicone toys — and lubricate whatever you plan to practice with. Then just press that object (or your fingers) against whatever opening you plan to play with. It may be helpful to start with the flat of your palm to get used to the feeling of pressure. As you grow accustomed to the feeling and the temperature (it may need a minute to warm up!) you should find penetration easier to accomplish, along with plenty of pleasure.

Like measuring a room for new furniture, now’s the part where you pay attention to the depth and width of your preferred insertion. Once you know just how much you can accommodate, you can guide your partner to the optimal level of insertion.

DO - THINGS TO CONSIDER BEFORE ANAL STRETCHING

Be sure to use the bathroom before you begin
If you're a little poopoophobic, you might want to consider an anal douche 3-4 hours before you start.
Stop without hesitation the moment you encounter any blood or experience strong pain. The point is to push yourself to the point of slight discomfort, not to tear your ass up. If it hurts you need to stop. If it is just uncomfortable, you're doing it right!
Start with a smaller, smooth butt plug. Make sure it has a taper. Wouldn't want to lose it!
Use a lot of lube. Seriously, you can't use enough lube! This is especially true for complete beginners.
Use a lot of lube. No, that wasn't a mistake, I didn't double up on this one by accident. You seriously are going to need a lot of lube. Do yourself a favor and follow this advice. Don't get the cheap shit either! You'll be doing yourself a favor.
Don't use anal numbing lube for anal training. You must be able to feel to know when to move on to a larger-sized plug or if you've gone too far too fast. Again, pain is an important indicator.

DON'T - THINGS TO AVOID WHEN ANAL TRAINING

Don't force it if it hurts.
Don't get ahead of yourself. Be sure to exercise a little patience. There's no need to go thrusting about now, that's what you're working up to.
Train every day. It's a good idea to let your body adjust and rest after a good stretch session. I found a good 2-3 days to be sufficient, but you know your own body better than anyone and will find what works for you. Just be sure to give it a rest from time to time to avoid any injury.
Start with a plug larger than 4.5 inches in circumference. Remember, the idea is to start small and work up.

WHAT POSITIONS WORK BEST FOR THIS?

If you’re doing it yourself, you’ll want to lie on your side and use your dominant hand, which is the one you write with.

Lie on the side with your knees bent so you’re comfortable.
Reach your hand around your anus to insert your finger or toy.

If you’re with a partner, you have a couple of positions to choose from. You can:

Lie facedown.
Have your partner sit or kneel next to you.
Get on all fours.
Have your partner kneel behind you

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What’s the Best Position for Bottoming?

Finding a good position is going to be entirely personal — it depends on the shape of the people playing and what they enjoy. But if you want to spice things up or make it easier to get in, there are a few good places to start your exploration. Switching up positions will add variety to the experience, and you’ll find new ways to enjoy yourself.

One of the least fussy positions is the “cowboy” pose, with the top lying on the back and the bottom kneeling on top, facing forward. That lets the bottom control the speed of penetration, which is key to everyone enjoying themselves. In the “reverse cowboy” pose, the bottom turns to face the top’s feet, which may be more comfortable for some folks.

You might also try the missionary position, which requires a bit more flexibility. In that pose, the bottom is on their back with the legs elevated, with the top lying above and thrusting down. This pose may require some pillows or rolled-up towels to get everyone in the right position.

The doggy-style pose places the bottom on all fours, with the top kneeling behind to penetrate. It’s an easier one to achieve, but it’s harder to look each other in the face if that’s something you enjoy.

Then there’s the spooning position, with both participants lying on their sides. The top comes toward the bottom from behind. This pose allows both parties to control the speed and depth, but again it’s hard to maintain eye contact. There’s also a standing-up version of this pose called The Bodyguard.

These are just a small sampling of the infinite number of poses available to you. Start here, but don’t be afraid to adjust positions or get creative based on what’s comfortable.

How do I Reduce the Pain of Bottoming?

A little pain is normal and even pleasurable for some people, but if you don’t want it to hurt, it doesn’t have to. If you’re experiencing too much, you can take steps to reduce it.

The key to avoiding pain is to go slowly, use plenty of lube, and communicate with your partner about what feels good and what doesn’t. Gradual stretching is key to avoiding pain or injury. If something feels wrong, let your partner know right away: “That hurts,” “Back up a little,” or “Let’s try something else.” Don’t be afraid to slow down or say “Let’s not try that again.”

What if your partner’s just too big for you? You still have options. Spend more time relaxing, cuddling, and stretching with fingers before full insertion. Maybe you just need more time to work up to it. Consider using more lube, or starting with a smaller toy. And as the bottom, make sure you’re in full control of how deep the penetration goes, so you can listen to what your body likes and what it doesn’t.

What should you do if it hurts?

Minor discomfort while you get used to the sensation of being penetrated is to be expected. Adjusting the depth or motion, or even just taking a deep breath, should help.

If you’re feeling actual pain — like a severe, sharp, or throbbing pain — then slowly pull out. You can try again in a couple of days with a smaller toy or after being sufficiently relaxed. If the pain returns, it’s a good idea to see a doctor to find the cause.

What should you do if there’s blood?

A little bit of blood that resolves quickly — think light spotting — probably isn’t a big deal.
See a doctor if there’s a lot of blood, bleeding continues for more than a couple of minutes or is accompanied by pain.

A little bit of blood is not abnormal, and it’s not necessarily a cause for concern. If bleeding happens, it should go away in a day or two. If there’s a lot of blood, if there’s disruptive pain, or if bleeding lasts for more than two days, you should go to a doctor or a clinic. They’ll know what to do.

But don’t be worried too much about pain or injury. With just a little preparation, you can mitigate the risks, and with plenty of communication, you can change course if something starts to go wrong. Remember, the whole point is to have fun and feel pleasure with someone you like.

TECHNIQUE

Now that we have the basic do's and don'ts out of the way, let's move on to technique...

STEP 1 - GETTING WARMED UP, GET READY AND OPEN YOUR MIND

First, you are going to want to find a position that's right for you. Then, relax and begin with your fingers. Don't just go jammin' them in there willy-nilly.

Just lube up your fingers and work them around your hole a little bit while trying to relax your anus. Using circular motions feel it out and massage it a bit. When you think you're ready, start to slowly insert them into your anus. Keep up that slight circular movement.

OPEN YOUR MIND (THE MORE YOUR MIND IS OPEN, THE MORE YOUR HOLE IS OPEN TOO)

Once you are comfortable with the presence of one or more of your fingers in there, try to give a little stretch with your fingers and see how it feels. If you are comfortable with this, move on to step two.

STEP 2 - TAKE IT LIKE YOU WANT IT

You have to want it to have it in. If you don't want it, your autonomic nervous system will automatically squeeze your hole because of the "fight or flight" system in everyone's body. Once you want it, your mind will be brave and the hole will open up nicely. You can practice squeezing and open and squeeze and open (your hotel) and you'll see that if you open it or push it out, your hole becomes bigger and more open.

How do you insert?

Take a deep breath and increase the pressure, slowly pushing your finger or toy inside.
Try to insert the toy an inch or so over about 3 or 4 minutes.
If met with some resistance — which is normal — gently remove it, apply lube again, and try again. Once you reach the point of discomfort, leave it there for a few seconds and retract it.
Then, slide back in there. Try to go a little further this time. If you can only reach the same point as before, no worries. Just keep repeating this process until you've managed to take the whole of your smallest-sized plug.
Once inside, use a gentle circular or thrusting motion.
Be sure to reapply lube every time you take it out and start again.

STEP 3 - BECOMING A MASTER THROUGH PRACTICE

It gets pretty simple from here on out. You repeat the same process only with the next largest plug. Follow all of the same steps as the previous size. Remember, there's no need to rush. Did I mention you should use lots of lube?!

You'll want to keep this up until you reach master the largest plug you have. That's pretty much it! Just be sure you give yourself time to recover after each session and be sure to not attempt moving up to the next size plug too quickly, and you should be all right!

THE BOTTOM LINE

Anal training can help you master anal play and take it to another level. When done right, you can work your way up to easy and pleasurable anal sex, or take it even further with gaping or fisting, if that’s your bag. Now go get busy bottoming!