5 reasons you’re not ready to have anal sex

Anal sex. I’d be lying if I said I wasn’t a huge fan.

I love butt sex for a multitude of reasons. Even though it’s something more people of all genders and orientations are exploring and enjoying, there’s still an element of it being taboo that turns me on. I also happen to like the sensation of anal sex as the anal sphincter is tighter—generally speaking—than a vagina. 

I like offering partners who have never tried or liked anal sex before a safe space to explore whether it’s something they may want to have in their sexual repertoire.

Now, as you may have read on this blog—or seen in my Sex Hacker Pro video course—I have an average-sized cock. One of the many advantages of having an average-sized cock is that it’s less likely to intimidate an anal debutante. 

In fact, my average size, plus my nerdy dives into anal anatomy and pleasure, and oodles of experience have resulted in my partners having positive first-time anal encounters. I’m particularly honored that partners who have had negative experiences with anal have been game enough to overwrite those less-than-optimal memories with new, positive ones. 

I use this concept called anal trust, which describes the amount of trust that you must have to allow someone to penetrate a delicate part of your body which has the potential to cause you a lot of pain and harm if it’s done without putting your well-being above their need for pleasure. If you get to the “anal trust” level, and people experience pleasure, that trust expands to every aspect of your sex life because you’re proved you can be trusted with their most vulnerable parts.

The point of this blog post is to encourage you to be the kind of partner who creates a similarly safe, fun, no-pressure environment for your partners to explore anal sex for the first time or get back up on the horse if they’ve tried it before. Maybe they’ll love it! But if they don’t, let’s make sure that they’ve found that it’s simply not their cup of tea and not one of these anal sex goofs. 

1. You think that just because she’s had anal before, it’s on the menu for you

Perhaps it came up during a getting-to-know-you conversation. She’s not an absolute anal beginner. She may have even told you that she liked it or that it’s been a regular part of her repertoire with previous partners. Here’s what that juicy tidbit means for you. Nothing. There’s absolutely zero connection between the sex acts she’s engaged in and enjoyed in the past and what she’s interested in doing—or not doing—with you.  

While you might want to think that it’s your intimidating schwanz that’s making her balk at the idea of you being her backdoor man, it’s much more likely to come down to something else. My money is on trust. 

Trust is something you must earn and it takes time. If you want her to even entertain the idea of anal sex with her, your patience trustworthiness, and has to show elsewhere. If, for example, you’re jabbing your fingers into her vagina before she’s sufficiently aroused and lubricated, she’s definitely going to be thinking twice about letting you anywhere near her smaller, non-self-lubricating hole.  

2. You haven’t explored your own ass

To turn the popular witticism on its head: assholes are like opinions… everybody’s got one! By contrast, you are a penis owner; chances are good that you don’t know what having a vagina feels like and vice versa. The anatomy of the anus and rectum, however, is pretty similar regardless of gender because every asshole’s main job is the same—to excrete food waste. 

So what does this mean for you? It means that provided that you have fingers, you have everything you need to start to get a sense of what receptive anal sex feels like. You’ve really got some balls to think that you get to spelunk without having first been spelunked—if only by your own hand. 

In the spirit of “what’s good for the goose is good for the gander,” have a little exploration session the next time you’re in the shower. Step one is to make sure that you’ve had a complete bowel movement and have that just-pooped empty feeling. Then, in a hot shower, explore your anus with one soapy finger. Notice how your sphincter puckers and relaxes when you are knocking at the gate, as it were. Then, slowly insert your finger and begin to get a sense of what it’s like in there. 

If you really want to go the whole hog, try inserting a toy that’s not too dissimilar to your cock in terms of size and shape. Note: ensure that this toy has a flared base! ERs are awash with tales of people inserting things in anuses that need to be fished out with forceps, often at some considerable expense.

Love it or hate it, this round of self-exploration should at least give you some context for what your partner will feel if you’re lucky enough to be invited around back. 

3. You don’t have patience

Don’t believe everything you see in porn. In the real world, monster cocks don’t slip effortlessly into anuses willy-nilly. Diets are manipulated, medications are taken to start and/or stop traffic in the lower GI tract to prevent shit from happening, and outrageous amounts of lube are employed to mitigate discomfort. Most importantly, civilians are far less likely to have spent hours and hours of screen time training their bodies to do what they want on cue. 

In the real world, patience is going to be key, particularly if your partner isn’t a dyed-in-the-wool analista. A good hack that I’ve employed on many occasions is to put your partner in charge and simply stay still. If she’s on top, she can envelop your cock with her ass at her own speed. If you’re in doggie, she can similarly back into you at a pace, depth, angle, and intensity that suits her. Your job? Stand your ground. At least until she’s communicated that you can move. 

For some people, feeling comfortable might take a while. Long enough, in fact, for your penis to soften. In my experience, having a little sildenafil (brand name Viagra) on hand can be really useful in making sure that you’re rock solid when she’s good and ready to back that ass up. Note: You should only take erectile dysfunction medication that’s been prescribed for you by a doctor. 

4. You don’t know about the risks of switching from anal to vaginal penetration

Another thing we see a lot of in porn is penises going from vaginas to anuses and back again. Does it look like fun? Certainly. Does that back and forth increase the likelihood of your partners getting a bacterial infection? Absolutely. 

From a young age, girls are taught to wipe from front to back. That’s because introducing fecal matter to the vagina is, sooner or later, not going to end well. Specifically, it could end with bacterial vaginosis, a yeast infection, or a urinary tract infection (UTI). 

If you are fluid bonded with your partner, meaning that you are not using condoms. It’s important that you thoroughly wash your penis between anal and vaginal sex. This goes for tongues, toys, and fingers too. If you are using condoms, you will also have to wash your penis in addition to putting on a fresh condom. That’s because condoms don’t always cover the entire penis (or dildo), so there’s a risk that some bacteria may still be present. 

5. You can’t deal with a messy situation because shit happens

Pain is one thing people are rightly worried about experiencing when having anal sex. Another is the prospect of shit getting everywhere. Of course, this is perfectly understandable, given that pushing out poop is the anus’s primary job. Again, this is something that we rarely see in porn, though I’d bet that every year plenty of footage featuring this very reality hits the cutting room floor. 

I don’t want to yuck your yum, but I think it’s safe to say that the presence of fecal matter is the last thing most people want during sex…even if the activity they are engaging in is basically inviting that very thing to happen. 

The good news is that if the receptive partner has used the bathroom and had a thorough shower, the chances of your unwittingly letting a massive amount of shit lose are pretty slim. Put simply, poop doesn’t enter the rectum in large quantities until you feel the urge to use the bathroom. What’s more likely is for smaller remnants to be shaken loose via the process of fucking. It doesn’t happen too often, but it certainly happens some of the time. 

So the move here is to expect the best and prepare for the worst. First off, let her know in no uncertain terms that you’ve got her and, should things get messy, you’re not going to make a big deal about it. Shit, you may want to remind her with a wink, happens! 

Have a dark towel or disposable puppy pad under you, and at the point at which shit is likely to get real. In the event that things do get messy, stop what you’re doing, get that towel or puppy pad out of there, scoop her up and jump in the shower together. If the mess is minor, having some baby wipes at hand will enable you to wipe any nastiness away and keep going, if you’re not faint of heart!


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