Anal Sex Guide for First Time Bottoms




Imagine this — you’re in the club, looking for your next trick (that’s a hookup for all you Gen Z-ers). You spot a dude hotter than the sun, approach him, and make your move. You guys dance ‘till you can dance no more, and then you drag him out of the club and down the street to an Uber that will serve as your personal stairway to heaven. All the while, you’re kissing and letting your hands wander all over his body.

You fall on your bed, lips meeting, hips grinding up and down. You’re giggling because the guy’s perfect, sweet, and, did we mention hot? His kisses leave goosebumps on your skin, and the Gods graced him with lips made for sucking your cock. And so he does. He sucks it like a champ, and then he pops up and says: “I’m a top.”

Which would be fine, except you never bottomed. So, now what?

An Alpha Top or a Power Bottom?

OK, so this might be a far-fetched scenario straight out of a Queer as Folk episode. Ideally, you’d have a lengthy talk with a potential partner about boundaries, preferred roles in bed, anal play, sex toys, etc. And, ideally, men shouldn’t feel the pressure to limit themselves with labels like “top” and “bottom.

But, also ideally, you should broaden your horizons (and enrich your sex life) by trying both. Anal intercourse can be both wonderful and exhilarating, no matter who’s the receptive partner. If you’re bottoming for the first time, you’re probably intimidated.

Sure, you know what feels good (sort off), and you experimented with butt plugs, prostate toys, or maybe even dildos. After all, gay men are no strangers to anal stimulation (even if they are baby queers). We all tried to catch that magical unicorn of a prostate orgasm as soon as we found out about it. But does that mean you’ll instantly know how to bottom like a pro?

To be honest, probably not. Bottoming includes a lot of prep (like a lot).

A Fresh Start — Cleaning Is Crucial

Power bottoms will be the first ones to tell you that bottoming is a way of life. Fresh-faced boys with virginal asses might think that bottoming takes a lot of experience to master. However, it only takes good prep. And what’s the first step of prep? Cleaning.

There’s more to gay sex than dragging your underwear to your ankles and letting a top pound their little heart out plowing your ass. In fact, we don’t recommend that at all.

Gay sex starts long before a dick goes anywhere near your ass. Now, most will immediately think about rectal douching here. And while it’s true that the bottoms bear the responsibility to keep themselves sparkling clean down there, using a rectal douche still isn’t first on our list. The first step to a clean ass is the diet.

A light, high-fiber diet will make the cleaning process go smoothly. What’s more, you have to plan your sexual activities around your meals (or the other way around). Bottoming after meals isn’t comfortable, so wait at least 3–4 hours before you give it your best shot.

Anal Douches Are a Godsend

Next comes the cleaning. Cleanliness is vital both for health and for your peace of mind. You don’t want to bottom thinking you’re dirty down there.

If you use a device for cleaning (i.e., a douche), make sure it isn’t oil- or saline-based. Regular old soap and water will do just fine. Oil is too messy, and saline solutions will burn your rectum so severely that you won’t be able to think about sex, let alone bottoming. 

Anal cleansers that you can use in the shower will clean you out effectively and quickly. If you aren’t a fan of this, get an enema douche and go to town. 

A Little Training Goes a Long Way

If you’ve never tried shoving a finger (or a toy) up your butt, now’s a perfect time. Trust us — you do NOT want the first thing to penetrate you to be the dick of your insertive partner. 

Squatt in the shower and take advantage of your soapy fingers to feel around your rim, and maybe slip a finger inside. See how it feels!

Since most of you have already done that, there’s no need to get down to the dirty details of fingering yourself. However, to truly prepare yourself for bottoming, consider using anal training kits. 

Anal Training Kits

These will help ease you into the world of blissful anal pleasure — one inch at a time.

Anal training kits usually have several anal toys in them. As a bonus, some kits also come with douches. That’s a handy way to knock two birds with one stone.

So, invest in an anal kit that will train your pucker and get it used to the delicious burn of a proper stretch. Of course, it’s always advisable you start small. If you’ve never dabbled in the glorious anal play of any kind, get a kit that has a tiny, slim plug as a starter toy and work your way up.

Pay attention to the flexibility of the toys in the kit as well. You might think that the more flexibility a toy has, the better, but if you’re prepping for the gay sex Olympics (aka bottoming), a toy that’s too flexible won’t be of much help. Something more rigid will go a long way in training your anal muscle control, endurance, and strength.

(Vibrating) Prostate Massagers 

If you want to step up your game and discover ALL the tempting benefits of anal play, try masturbating with a prostate massager. Massagers that can reach your prostate are excellent preparation for actually bottoming because they are longer than plugs. 

You can work your way up to a massager after you bottom your way through your anal training kit. These toys are excellent, and they WILL get you hooked up to bottoming. Their smart curve makes reaching your prostate an easy task. You’ll go from fishing in the dark to hitting what feels like the core of your soul in no time.

Lube UP!

You can never apply too much lube. Lubricant is the most vital part of anal play. A high-quality product will make the slide easier and diminish the chances of tearing and other injuries. Remember, dry bottoms are sad bottoms.

Those who shy away from bottoming because they are scared it will hurt should know that the brilliant sex toy industry has the solution for them. Numbing lubes are now a thing, and they have revolutionized anal sex. You don’t need a lot, so you can buy a desensitizing lube and mix it in with your regular lube. It will take away that initial sting of pain.

Another handy product to have is a lube launcher or a lube shooter. It will make sure you’re properly prepped everywhere. It comes in handy if your partner is particularly endowed (you lucky bottom, you!)

A Few Parting Words

Bottoming is not rocket science, but it’s also not an easy task. So, if you decide to try it, make sure to prep properly. Just remember to relax and stop clenching (you’ll do it because you’ll think you’re pooping, but don’t worry, you aren’t, the sensation is just similar.). 

If, in the end, you decide bottoming isn’t for you, that’s perfectly fine. Not all of us are born to be greedy bottoms. Perhaps you can try out cock cages instead. They are intimidating I know but, Cock cages can increase pleasure if used correctly. 

No matter which position you choose, make sure always to protect yourself and your partner. No glove, no love — especially with new partners.