Pitching and Catching: Asking For Anal

Q. Hi. I’m a guy, age 24, studying physics and math, who has a strong love of anal sex. I do my best to research stuff about it because the hottest thing for me is a girl who loves anal sex, and I’ll be damned if I screw that up for anyone by pushing too hard to do it, or by doing it wrong and hurting someone. I consider safety and her pleasure the highest priorities. I’ve tried to do things on the receiving end of ass play, but I haven’t figured out how to make it work for me, yet. I only know that I love being played with there as well.

But that’s all fluff and background. My issue is this. Throughout my youth, my parents and my friends have, whenever any evidence was found of my fascination with buttsecks, given me no end of torment. I now find it extremely difficult to talk about anal sex with anyone. Don’t get me wrong; I have accomplished this feat several times in the past, and sometimes with a respectable amount of success, but it is never easy. I am tired of being afraid of my own desires. How can I do this? More specifically, how can I ask for anal sex and not seem weird/stereotypical/gross/etc.? How can I become comfortable just talking about it with others? 

A. I’m sorry that you have been given so much lip about your interest in anal sex. I imagine that people who have an easy time by riding others for their sexual desires are most likely the same people who have either: 1. not figured out their own, or 2. know better than to tell anyone. Which is not to say you have done anything wrong – if I’m suggesting anything, it is that making fun of people for their sexual desires, the ones that are usually pretty innate in our sexual egos, is a bit of a low blow. Also, are they like fifteen? Who does that?

Photo of Shannen Doherty and Ben Affleck from the movie Mallrats.
Don’t ever be this guy. Especially if you are old enough to know who this guy is.

Now, that being said, I can understand the generalization of creepy gentleman looking to do nothing but stick their dicks into a lady’s rear end. Do you remember Ben Affleck’s character in Mallrats? The Nice Guyâ„¢ who just happened to swoop in at every vulnerable moment in the life of the ladies around him. He cooed and coddled, but ultimately just wanted a chance to stick his dick up their asses. Not for pleasure, not because it turned him on, but because it made him feel powerful. It made him feel “like a man.” While your dilemma doesn’t even come close to the creepitude that Ben Affleck was walking around with, or hell, even the potential creepitude of this gentleman who asked a similar question not so very long ago, it will at least give you the idea of the anal sex hoops that we ladies have to jump through sometimes. It’s not the idea that anal sex isn’t something we are interested in – far from it. It’s the idea that many who go into it, go into it as a weird power play fantasy they’ve absorbed through the osmosis of  watching mainstream hetero dude porn, thus, giving said gentleman a few misconceptions about the actualities of anal sex.

Like, no you can’t just stick it in there willy nilly. No, you cannot pound away at someone’s ass like a rodeo horse. No, women do not (always) cum from anal sex. No, it does not always feel awesome. No, you absolutely cannot not use lube.

I don’t get that feeling from you. You state that not only do you want to not be a creeper, but you also want to receive anal play, which unfortunately is a huge game changer. Want to know how I know? Because once upon a time when I was a young gal, I happened to be conversing with a guy who I had been dating for a very hot second. Over dinner, we started discussing anal sex and how he thought it should be standard in a relationship. While standard may have not been the word I would have used, I asked, “Have you ever had anal sex? Like been pegged or used a butt plug or been penetrated anally?” His face recoiled with instant disgust and he said, “Ew, no, that’s gay.”

Welcome to the inherent dilemma of anal sex.

Not only did that dating scenario end very quickly after that conversation, but my own apprehensions of having anal sex became  a bit more crystal clear. I had realized that anal sex was – or had been, at some point – feminized. Anal sex and anal play were something that a woman did – or a gay man. Nothing in between. It was a perceived act of submission, one that was standard in the sexual buffet of many young men I knew, not because of the enjoyment, not because of the sexiness of the act, and certainly not because they themselves wanted to receive anal play, but because women were kinda supposed to. Sure, this might be reading into it a bit too much, but you can maybe see why many ladies have a dilemma with anal play. Now, I use the word many, but certainly not all. I think at the age of 24, you might be meeting more of these ladies who do have apprehensions about anal play, solely because the exposure to anal sex they may have had has been, well, somewhere along the lines of uncomfortable, to disappointing, to unpleasant. By no means is this your fault, but, it is something that you seem to be aware of. I do want to give you hope for the future though. As we grow and change, and thus, begin to understand ourselves and our desires better, we take a little more autonomy into our hands and sometimes become more open to a sexual act as itself, not as the baggage that comes along with it.

So, what is a guy like you supposed to do? It honestly sounds like you are on the right track now: you seem open and honest about your desires, and especially communicative. I would suggest the old saying of, “Remember, it’s not what you say, but how you say it.”  How you present your desires, I think, is the hugest issue. If you present your interest in anal play like an infectious disease or a shameful burden, you might invite those perceptions in. Your desire isn’t shameful. Or perverted (well, it may be perverted, but in the good way) or weird, or even stereotypical. If your desire were stereotypical, you would be arm wringing the ladies you sleep with into giving you anal sex because you think you are entitled to it. You don’t feel entitled – you desire it. There is an ocean’s worth of difference in the two and while we are all entitled to our sexual desires, what makes us or breaks us, is how we take our desires into our own hands. Do we do it respectfully, or do we try and cajole? Entitlement to your desires is one thing, entitlement to everyone bowing down to those desires is a whole other.

Now, unfortunately, you might have to take a few swings, and a few misses. Not every woman you end up sleeping with is going to be into anal play. Your limitations have to be understanding that and not cajoling, but finding someone who is open enough to try or even enjoys anal play. The world is not naught for them. These women exist. Seriously. Tristan Taormino did not just pop out of a vaccuum. These toys do not exist for the visual aesthetics’ sake (hell, they might help you out as far as finding something that is more pleasurable for you in the receiving end). The catch is, you just might have to look for a while. If you want, I would suggest trying Adult Friend Finder as a starting point. It might cut out a lot of the guesswork and you can go straight to the sexual activity that you are hoping for, whether it is pitching or catching. The presumption is also that you will find someone who is not only open enough about their sexuality to be on a site like AFF, but be open enough to hear out your desires, and potentially be just as receptive and excited as you are. It is not a given. AFF is not the holy grail, but, it will feasibly help you out in finding some compatibility as far as someone who shares your sexual interests.

Lastly, I would say, try to relax a bit, my love. Now, that’s a loaded phrase and it can be dismissive when people tell you to relax because it doesn’t address the actual source of anxiety. But so much of your anxiety is coming from a place of good intention and honesty: you don’t want to be a creeper. You don’t want to stave off your desires. You do want to be respectful. You will listen to your partner. Keep that alive and afloat because that is what makes you a good partner and that is the most valuable asset in creating a healthy sexual relationship. If you do end up in the sack with someone who doesn’t want to try anal play, consider it a favor. If anal play is what you need in your sexual diet to keep you happy, there isn’t much sense in being with someone who isn’t about it. So while the rejection may sting a little, consider it part of the all inclusive package. You wouldn’t necessarily be with someone who said, “Well, I hate tattoos” when your own body is covered with tattoos. The rejection isn’t even coming from a place of really knowing you – it’s only knowing a facet of you. Try to not take it personally,and realize that that person just wasn’t the person you needed to be with. This doesn’t mean that you shouldn’t leave room for negotiation – just that finding someone who is sexually compatible with you will save you and that person some frustration in the long run.

So attempt to let go of some of that anxiety. See a therapist, talk about the anxiety with your partner, do whatever you can to quell the nervous energy and transform it into a willingness to communicate what you want. My suspicion is, that once you are talking about your desires in a way that’s less about encroaching, but more about what you honestly want, the anxiety will fade. In the meantime, experiment with your own realm of anal play. While you may be partnerless at the moment, get some toys and start figuring out what works for you, as far as anal play for yourself. When the time comes to present your interest in anal play to a partner, and they hear that you are equally excited about catching as you are pitching, it won’t come off as an entitlement, but a fully explored desire that you want to share – and there is nothing more sexy than that.


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4 replies on “Pitching and Catching: Asking For Anal”

This is a wonderful reply. My sexy times partner and I started explorin anally. He had questions about how I would react to his desire to play with my ass but I was very receptive to it. While I don't love it as much as vaginal, vulva play, I love that he loves it so much so it makes it pleasureable for me. A lot of it has to do it how you approach a partner. Be honest and sincere when you ask them. It's great that you are willing to both catch and pitch! Good luck!

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