how to have anal sex first time
First time bottom tips

First Time Bottom: Anal Tips

By Rico Woods

I can remember as a younger gay man being completely consumed with  being a first time bottom. Specifically, I'm talking about knowing how to do anal. I think part of my fascination with the topic was directly linked to my strong need to please the guys I had sex with.

You see back then, – when I was a first time bottom – we didn’t refer to casual encounters as “hookups” but instead, “tricking”.

But I digress.

Anyway, when I was in my early 20’s, there really wasn’t a lot of information available about getting f*cked. Sure, you could look at videos to see how other people got pounded but deep inside, you always knew they were acting.

Today, there’s plenty of material about gay anal sex out there, including webpages, tutorials and even books. Who would have thought gay acceptance carried such perks?

Still, when you look around, much of what’s on the market has an erotic tone to it. I’m not saying there’s anything wrong with this. There’s not. But if you are old school like me, it’s always nice to get useful advice from someone who has real world experience.

First Time Bottom: Learning from My Mistakes

Can I tell you a secret? When I first started receiving anal, I thought all you had to do was take a dump and wham – you were ready to get plowed.

“Just lay back and let the guy do his thing,” I can remember thinking.

That may sound silly but I’m sharing this to give you an idea of how ignorant I was.

It was only after one of my first boyfriends told me that I “needed to do a better job cleaning” that I realized I had lots more to learn.

After that not so easy to hear bit of advice, I began a radical quest for knowledge on how to properly first time bottom, including what to do for preparation.

I talked to anyone I could about this topic – particularly older men who proudly identified as power bottoms.

I learned a lot from these discussions. Probably the biggest take-away was that you don’t have to like getting topped in order to be a good bottom.

I also learned that versatility helps when trying to please another man.

Related: What’s the definition of a power bottom?

I’m mentioning these points because it seems too many of us feel pressured to pick a role and stick with it when it comes to the whole “top or bottom” thing.

Take it from me – that’s a bunch of bull-sh*t. I’m fairly versatile but lean towards bottom. But I know plenty of guys who identify as exclusive bottoms.

First Time Bottom: 10 Tips

What follows are 10 tips for first time bottom guys interested in anal. All of these suggestions are based on my personal experiences, which you’re going to read about as we continue along the way.

Hopefully, you will walk away from this page feeling more knowledgeable and empowered. Some people bookmark this to their browser for quick reference. Just sharing this as a kind of pre-tip before we dive in.

OK, let’s go through the tips.

10 first time bottom tips
10 First Time Bottom Tips

1. Ask yourself why you want to bottom for the first time

Before reaching for any guides or videos on how to get f*cked, I encourage you to ask yourself: why you want to have anal sex? Is it because you think it’s a must in order to be gay?

One of my first bottoming experiences was painful because I tried to ride a guy that was way too large. The reason I did it was because I thought “that’s what gay men do.” I was totally wrong.

Here are some more thoughts to reflect upon:

  • Some people are born natural tops. Others are versatile and still others, total bottoms.
  • Have you tried topping? Did you like it?
  • Bottom for the right reasons, like being into a guy. Don’t do it because you think it’s a requirement to be gay.

2. Get mentally prepared

The old saying that “sex is all in the mind” really is true, particularly for bottoming. If you are newbie, this means it’s important to prepare yourself mentally before doing anything physically.

Rather than just laying back and letting your man do his thing, I have found it helpful to mentally rehearse the experience before he ever sticks it in.

Doing so allows you to anticipate potential pain and establish a pain threshold.

One way to help acclimate yourself to having anal sex is to simply feel around your anus after cleaning (see tip #3).

Here are some additional thoughts for self-exploration as part of mental rehearsal.

  • Squat down in the shower and with a soapy finger, gently explore the lining of your asshole.
  • Lay down on the floor and touch the lining of your anus. If you want to use a little lube, that’s ok (see point#4). Over the course of time, push your finger inside and feel around. Become aware of the different sensations and pleasure points.
  • Consider getting a high quality anal trainer kit  with a good silicone based lube as a run up to your first time experience. The good thing about the kit is that you can start off super small and graduate to larger sizes. I did this earlier in life and it helped. Many beginner bottoms swear by this!
  • Fantasize about the guy you want inside of you as you masturbate. The trick is to allow yourself to feel him in your mind.

3. Use the anal cleansing tools (Douche)

Once you are mentally ready, you need to get physically prepared. This means taking the time to properly clean yourself out.

I want to spend a few moments on this particular issue because it is of vital importance.

Part I: Diet and Having Anal Sex

  • First, if you are eating a high fiber diet that is conducive to anal sex, the cleaning process will be much easier. I encourage you to read this article on anal sex and your digestive system.
  • Second, if you have gastrointestinal issues, preparation becomes even more important. Read this post on constipation and anal.
  • Allow enough time for food to digest before bottoming. In other words, don’t invite somebody over to top you if you’ve just got done eating. The reason is your entire digestive system is processing food, which, when receiving anal, can cause bloating, discomfort and gas. Wait at least 4 hours after a meal before allowing anyone inside of you.

Part II: Cleaning Your Ass and Anal Sex

      • Consider investing some money in a high quality anal cleanser (aka douche). One of the best ones you can buy is the 4 in 1 shower cleaning system. You don’t need a lot of water pressure with this device. Just a little warm, soapy H20 and you’ll be amazed how well it removes all of the nasty stuff inside of your butt. I personally use this one and it has never let me down – not once.
      • If you prefer not to use a shower system, you can get a high quality enema (douche) from Amazon that ships discretely to your home in a non-revealing package. Again, warm, soapy water is all that is needed for cleaning yourself out.
      • Always make sure that you wash your anal cleanser out and disinfect it after each use.
      • Do not buy saline based enemas unless you have a medical reason for doing so. They burn the hell out of the lining of your anus and can cause discomfort when you are being penetrated. Trust me – I know – I’ve experienced the painful effects and I wish someone had told me this.
      • Skip the oil based enemas too. They are messy and can cause stains on your sheets and on you.
      • Never use devices that aren’t specifically designed for anal cleansing. This means empty plastic bottles of soda or “turkey basters”. I’ve tried both and I’m here to tell you they don’t work and can lead to serious injury.

      anal douche for gay men

4. Use a high quality silicone based lubricant 

This bit of advice may seem like common sense but I’m mentioning it all the same. If you are going to have anal sex, use a silicone based lubricant. This is particularly true if you are fairly new to anal and your hole has never been stretched out.

      • Great brands to purchase at your local drug store or supermarket include Gun Oil or Wet’s Platinum (silicone) product.
      • If you are worried about pain (we’ll get to that in a bit) you can also combine a touch of Clean Streams desensitizing lube. This one contains 2% lidocaine, which acts as a numbing agent. You only need a few drops of this to mix into your silicone lube. Great for anyone adverse to pain.
      • If you are completely new to anal or not very experienced with bottoming for big men, it may help to get a lube launcher. You can learn more about the benefits of these types of helpers by reading a guide on playing with giants!

gun oil lube
Excellent Lube for First Time Bottoms


5. Consider using a condom

There are a number of reasons you might want to use a condom, particularly if it will be your first time. This may seem counterintuitive but let me explain why.

Condoms are enormously helpful for beginners who are still mastering the art of cleaning themselves out. It takes time and practice to do a good job and so a rubber helps to avoid poop from getting on your man’s c*ck.

A rubber also helps to prevent the spread of STD’s. You may want to get f*cked right away but taking a few extra moments to have him slip one on can avoids the drama of health problems down the road.

If you do decide to use a condom, one of the best ones you can get for anal is Lifestyle’s Sensitive Pre-Lubricated brand. Not only do these feel very natural for your man, they also have a little bit of lube on them to help with insertion.

If you decide against condoms, have some baby wipes nearby to act as a “just in case” for cleaning purposes.

6. Relax your anal muscles

One of the main reasons many guys shy away from anal sex is because they can’t get past the sensation of feeling like they are going to poop.

If you have cleaned yourself out right, that simply isn’t going to happen. But I’m here to tell you that those first few times, it does feel that way.

The way to move past this sensation is to do the following. Bear in mind, this one takes some practice:

      • Take a deep breath as he’s inserting his stick inside of you.
      • Relax your pubococcygeus (PC) muscles and resist the temptation of tightening them up. That’s why it’s important to explore your hole from tip #2. Knowing the different muscles of your anus helps a lot when it comes to getting f*ked.

7. Getting the head in

The most difficult part of getting f*cked is getting past the head. That’s because for most guys, the tip of the shaft is going to have a “mushroom” shape.

In my experience, there are two approaches to help you move past this challenge and on to major pleasure.

Option #1:

Start out on all fours and let him get behind you. Tell him to slowly and gently push it in. You can even guide him with a free hand. Make sure he’s super lubed up. And it really helps if you can slip on a cock ring so that he remains completely firm during the process.

Option #2:

Lay him down on the bed or the floor. Take a good sized portion of lube and apply to his entire stick with an emphasis on the head. Then, slowly squat on top of his rod until you are past the head.

I don’t recommend getting on your back first because you won’t feel like you have any control.

If I haven’t mentioned this before, I will it now. Sex, (particularly anal), is all in the mind. This means you need to be part of the process and not play a passive role.

8. Don’t freak out if you feel like you’re pooping

At some point while he’s topping you, there’s a strong possibility that you will feel like you’re going to poop. THIS IS NORMAL. If you have taken then necessary steps to clean your anus, you have nothing to worry about.

To get past this issue, simply allow the thought to be present in your mind, but don’t act on it. In time, your fear will fade away. Remember, the more you freak out about it, the more powerful your anxiety will become. Make sense?

9. Stroke your stick

Once you get past the head and “sh*tting fears”, you’re now ready to experience true pleasure. The stimulation you’ll feel as he inserts his manhood into you can be overwhelming.

That’s because while he’s stretching out your anal walls, he’s also stimulating your prostate gland; a walnut sized erogenous center just below your bladder.

Here are some thoughts:

      • It’s OK to touch yourself and even release, particularly the first couple of times riding a guy.
      • He may want to stroke you but don’t let him just yet. Well, that is until you gain more experience. Otherwise, you may shoot sooner than the both of you want.
      • Don’t worry if you aren’t hard when he’s inside of you. It takes time to get used to a man thrusting in and out. Anxiety, coupled with fear of the unknown, can cause your peen to shrink.

10. If you decide it’s not for you, that’s OK

Many guys try to make themselves become bottoms when in fact, they’re just not wired that way. This is why I personally believe it’s never a good idea to try and screw a true top.

One of my first relationships ended because I tried to convert my boyfriend from top to bottom. Don’t ask me why I wanted to do this – I just did. Because of my ignorance, I kept trying to make him “enjoy” something he wasn’t capable of.

I’m not suggesting that you shouldn’t try to see if you are versatile. You should. But at the end of the day, after giving it a whirl a few times, you may decide getting f*cked isn’t for you.

That’s OK – really! There’s nothing wrong with this. I don’t mean to belabor this point but as I’ve mentioned before, we have too many people in our community who think that in order to be gay, you have to know (and like) how to bottom.

Complete BS and don’t let anyone tell you otherwise.

Having Anal Sex Resource

If you want to learn more about how to have anal sex, there’s a very good book that I’d like to recommend called: How to Bottom Without Pains or Stains by Mike Miller.

As I mentioned earlier, sex, in all of its forms, is in the mind. By properly preparing yourself in advance (mentally and physically) you’ll place yourself in the best position for enjoyment.


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