First Time Bottoming? How to Prepare For Anal in 11 Steps

Are you planning on being a bottom for the first time but worried about being getting fucked? From douching to diet, these 11 butt-bangin' tips from Alex Hopkins will show you how to prepare for anal sex. Lube at the ready!

 

Anal sex is a rite of passage for gay men. But getting your precious passage primed if you're a first-time bottom can be anxiety-inducing. Not least of all because many of us are still not taught about anal sex in school.

Consequently, we often have to learn about how to have  anal sex and bottoming in roundabout ways. Through what we hear. Or porn. And, many times, on the job itself. 

 

First time bottom: the rookie mistakes

Impassioned but ill-prepared, when it comes to first-time bottoming, newbies naturally make mistakes. If we are feeling mega horny, we may try and take a cock too quickly. With too little lube. And perhaps too little attention to cleaning our nether regions.

Indeed, bottoming for the first time can be messy. And painful (who doesn’t recall that hideous, jabbing pain?) Sadly, these factors can put us off one of the most exquisite joys of gay life. But needlessly so. For these missteps are easily avoided by preparing for anal properly. Here’s our 11-step guide to first-time booty blasting. 

 

How to prepare for anal: 11 top tips

If you're offering up your ass for the first time, it's only normal to be both excited and apprehensive. But follow our 11 tips on how to prepare for anal sex – both mentally and physically – and you'll feel hopefully feel more confident about getting your peach pounded.

 

1. Mind over matter

Sex is largely about your filthiest fantasies. And how you explore and unleash them. The first step in preparing for anal is to mentally rehearse the act of fucking itself. Alone. What can you imagine happening? What boundaries will you set? Conjure up the sauciest scenes in pornographic detail. Then close your eyes, reach for your baton and whack off to your wildest imaginings. 

 

2. Essential anal exploration

Delve into your depths. In bed or the shower. Start with some fingering, one or two digits to begin. After a while, when you have gotten used to your own fingers, consider upping the ante with sex toys. For example, anal beads allow you to take a little more each time.

 

Are you privy to the delicious dimensions of the schlong that’s going to pop your cherry? If so, select a dildo that reflects his length and girth. In preparing for anal, your hole’s goal is to sample every sensation. Take note of each angle that brings both discomfort and pleasure. 

 

3. Watch your diet

When it comes to diet and how to prepare for anal, fibre is your friend! That's because it helps stop constipation and promotes healthy pooping. It can take up to 72 hours for your body to fully process food and, however impractical to plan, ideally you don't want to serve up your delectable derrière until eight hours after your last full meal.

If you're planning on bottoming for the first time then a pre-fuck coffee is a definite no-no. Caffeine is a powerful diuretic, so don't be tempted to stop off for a flat white pick-me-up en-route to a steamy session or things could get icky. Likewise, avoid fatty, spicy or greasy foods, as these can cause diarrhea. And unless your partner is into scat, that's something a first-time bottom will want to avoid. 

First-time bottoms should focus on lots of foreplay shutterstock/rawpixel

 

4. Discover how to douche

Accidents happen. But you can significantly reduce the chances of them by anal douching for first time bottoming. Bulb douches are cheap and easy to use. Insert a nozzle into the squeezable bulb. Then add warm water to the bulb. Insert the devilish device into your rear. And squeeze away. 

A Shower Douche can be permanently added to your bathroom. It offers a consistent flow of water for deep cleaning. But watch water pressure. And then there’s the Water Bag Douche. Here, the nozzle is attached to a bag, which can be hooked up in a shower. But also folded up, making it an indispensable travel companion for all you gay circuit queens out there. Douching before anal isn't always necessary and it's not something you want to be doing regualalry change the microbiom in the anus. 

 

“Even an accomplished power bottom requires lube – despite what he may claim. And for first-time bottoming, you’ll need lashings of the slippery stuff.”

As a first-time bottom you may feel devastated if you spot a bit of shit on the condom or his dick, but you don't need to feel ashamed and apologize – the vast majority of tops would have seen it all before and understand that it's part of the deal with anal sex. Our bodies need to release waste. As the saying goes, shit happens. 

 

5. Communicate constantly

So, as a first-time bottom you’ve probed both your fantasies and your butt hole. You're douched, feeling empty inside and ready to get try having his cock inside you. The next crucial stage in preparing for anal is to actually talk to your partner before you get down to it. Yep, talk.

Make sure to tell him what you want and express any concerns you have. Ensure he listens and understands. We tend to talk about anal sex as a casual act, but you’re actually offering him something sacred and wholly intimate. If he doesn’t respect that, you can change your mind. And continue to communicate throughout the horizontal shuffle. Tell him when it’s great. And definitely tell him when it’s not or you're in pain. If you're bottoming for the first time these are things that are bound to come up. 

How to prepare for anal sex? Communication is key

 

6. Focus on foreplay

Taking time to enjoy foreplay is an essential step in how to prepare for anal sex, especially if you've never bottomed before. When you're aroused, you body relaxes, meaning your ass will be more receptive to penetration – you really don't want him to just shove it in after a quick fumble. So, make plenty of time to enjoy each other's bodies before moving on to the full fucking.

 

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Warm yourselves up with lots of passionate kissing and oral sex, maybe throwing in a bit of dirty talk about how you're gagging for him to pound you deep. He may also want to go to town on rimming you to really relax your hole. Being eaten out anally adds as a great precursor to the next step...

 

7. Lather on the lube

Even the most accomplished power bottom requires lube – despite what he may claim. And for first-time bottoming, you’ll need lashings of the slippery stuff. The inside of your butt is astonishingly absorbent. Because of that, water-based lubes won’t work for very long – and constantly topping up is a passion killer. 

 

“Even the most accomplished power bottom requires lube – despite what he may claim. And for first-time bottoming, you’ll need lashings of the slippery stuff.”

 

Oil-based lubes work be better but can be messy (and can make the latex of condoms porous). So your safest bet is silicone lube. It has a thicker consistency and lasts longer. So you can thrust away with abandon and peace of mind. Apply it liberally to your ass and also to his cock. 

 

8. Consider condoms

Advances in HIV treatment mean barebacking is thankfully no longer a dirty word. However, when considering how to prepare for anal sex, a frank conversation about HIV status and your sexual health remains important. If you're bottoming for the first time, contracting an infection may be any extra worry you have aside from the worries of physical pain, so talking is essential.

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PrEP is increasingly a great option. However, it doesn’t help prevent the transmission of other STIs. Condoms do. Additionally, they can help avoid an unseemly mess. 

Condom-discussion is essential preparation for anal sex shutterstock/Diego Cervo

 

9. Heads hurt – at first

Sex, like the mystery of life itself, is a mixture of pain and pleasure. And sadly you can’t enjoy the latter without enduring a little bit of the former. So, you need to think ahead.. well, in the head. The head of the penis that is. 

When preparing for anal sex, accept that taking the tip of a todger can sometimes be hurt. But happily, not for long. You can ease discomfort by getting on all fours and going doggy. Or instruct your top to lie flat on the bed before slowly lowering yourself onto him.

 

10. Relax and relish the ride

Hurrah! So, you’ve taken the first frightening yet fabulous inch. Your mission now is to enjoy the rest of the ride. But slowly. Relax your anal sphincter with deep breaths. It may feel as if something nasty’s going to pop out, but this sensation is common. And the unthinkable is unlikely to occur if you’ve douched.

 

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Need extra help loosening up? Consider poppering up. Poppers (amyl nitrate) relax sphincter muscles in the anus by increasing blood flow to the region making it easier take cock (and they can also make you feel incredibly horny, bonus). However, don't overdo them, especially if you're a first-time bottom, as you may get dizzy (overuse can also leave you with a limp dick). 

 

11. Banish pressure

Talking about limp dicks, if that happens, don’t beat yourself up. Look, losing your hard-on is normal, especially if you're bottoming for the first time and experiencing a variety of feelings. It happens when you’re anxious. But as you move through those sublime, surprising sensations, you’ll probably return to full mast. And If not, so what?

Similarly, don’t get hung up on your prostate. This wicked, walnut-sized gland is the male G-spot. And it can give you mind-blowing orgasms. But stimulating it takes practice. Which gives you the perfect excuse to experiment with multiple gay sexual positions. 

 

The bottom line: preparing for anal sex

Bottoming for the first time is a monumental moment in your sexual odyssey. Apprehension is normal. But this is alleviated by a calm, measured approach in preparing for anal. And central to this is communication – with yourself and your partner. 

Will you morph from newbie to a piggy bottom? There are no guarantees. You may decide you prefer to give rather then receive. Or maybe being versatile and getting the best of both worlds suits you best. But you’ll undoubtedly have a rollicking time trying. •
Main image: shutterstock/UfaBiPhoto

What worked for you you bottomed for the first time? Share your salacious stories by commenting below...