The Right and Wrong Way to Ask Your Girlfriend to try Anal

Emma Lindsay
Nov 8, 2016 · 10 min read

Once, I dated this guy with some severe anger issues. My friends wondered why the hell I dated him (answer: he was very good looking.) We would fight regularly, and he’d get mad at me for things like being too tired to finish up a blow job, or that one time when the condom broke and I took the morning after pill. I dumped him after not too long, but I hold no real long term grudge against the guy. He may have been an asshole, but nothing he did to me was deeply traumatic.

On the other hand, the boyfriend I hold the most trauma from was someone everyone thought was the sweetest guy. No one warned me against him, no one thought he was a “bad” dude — but my relationship with him was very bad for me. He was unemployed, and seemed a little “lazy” perhaps, but he was just so sweet and his parents were giving him the money he needed, so what was the big deal?

Thing is, I understood I had to defend myself against the guy with anger issues. That boyfriend may have been doing things wrong, but I knew he was doing things wrong and I would fight back; I didn’t internalize anything. When he got mad at me for not finishing a blow job, I’d be like “you misogynistic prick!” It didn’t make for a good relationship, but it also didn’t make for a traumatic one. I saw I was getting a raw deal, and got out.

With the “sweet” boyfriend though, things were a lot harder to parse. He always acted kind to me, especially when other people were around. He was very gentle, and sort of funny and silly, but there were a few warning signs.

The first one was that he had no appreciation for the money his parents were giving him. Several of my friends have gone through periods of being supported by their parents in one form or another, but they usually appreciate how lucky they are, or are at least embarrassed by getting money from their parents which motivates them to work toward independence. This guy saw no problem with it, and would make no effort to make himself employable in any way. He’d just play video games all day. He had dropped out of college before declaring a major, so had no specialty he was working toward. I’m not completely sure what he’s up to now, but last I heard he’d never held a job or even an unpaid internship.

After going to MIT, I sort of appreciated his “laid back” nature in contrast to the chronic workaholics I was surrounded by. But, the parent thing was a big red flag because he didn’t value the work they had done to make that money. He didn’t think about what he was costing them, and potentially their retirement, to keep supporting him. He didn’t really see his parents as people; he only cared about them insofar as they provided him with money. Now, I don’t want to shame people taking money from their parents. I had a friend once who lived off the income from his mother’s business while he took care of her when she had cancer, so there are often good reasons. But, this guy was giving nothing back to his family nor working toward his own independence. He just wanted to ride that train until it stopped.

But, thing was, whenever you talked to him, he was so nice. He was very affectionate with me, and never yelled. Sometimes I would yell at him, actually, and so I always felt like I was the “bad” person in the relationship. Yet, I never argued with any of my other partners like that before or since. Something about this guy kept triggering me, and it was damn hard to put a finger on what it was. And, he’d never get mad back, he’d just explain his point of view in a calm, repetitive way. But, he’d never budge. He might claim to compromise, but he’d never change his behavior. When we’d get in an argument about something, he’d often agree to improve something that was upsetting me (say, he’d suggest taking a class to improve his employability) but then would never follow through. So, we’d have the same argument again and again. Now, I don’t even necessarily disagree with his decision to not change, but his way out of difficult conversations was to lie to me by making commitments he’d never keep. That’s the part that was super nasty; if he’d just said “Emma, I’m not going to get a job, take me or leave me” that would have been fair.

He handled his parents in a similar way (who also wanted him to get a fucking job.) He’d always act calm and never argue, tell them whatever they wanted to hear, and never execute on any of his promises. After a while, we all stopped arguing with him. It was impossible to convince him to do anything other than play video games.

My big issue with him, however, came when he pressured me for sex. He had a way of touching my body frequently when I didn’t want him to. I remember saying to him once “you act like you’re entitled to my body,” and he said “I don’t think I’m entitled to your body.” But, despite what he said, would keep touching me anyway. He didn’t care if I didn’t want to be touched, and the only thing that would moderate him was my anger. He understood if he got me too angry, I would cut off his physical access to my body and he didn’t want to argue, so he’d try not to push it too far. But, he was motivated by avoiding my anger not by watching out for my wellbeing.

I keep asking myself why was this guy so traumatic? Why, when I’ve dated other guys who touched me too much? I’ve dated other guys who pressured me to do things I didn’t want to do?

And the answer comes down to, there was never any genuine empathy for me, but there was never any obvious abuse either. He viewed my emotions as obstacles to his desires. He was always wheedling me, and manipulating me to get what he wanted. I had to be perpetually on guard protecting myself against him, because he was willing to hurt me if he could find a way of doing it that didn’t trigger my anger. For instance, he would keep grabbing my breasts if I expressed displeasure or irritation, but would stop when I yelled at him. He only cared about hurting me in so far as it prevented him getting what he wanted. Yet, he never hit me, or raised his voice even, so his behavior was never so obviously problematic that I realized I should dump him. I knew I was unhappy when we were dating, but I was never sure exactly why.

When pressuring me for sex, often he’d be cute about it. Or, maybe when I told him to leave me alone, he’d appear to act on it, but then try again in a different way, then give me puppydog eyes afterward to stop me from getting annoyed. Or, if I was getting irritated, he’d try to make me laugh to distract me. The thing is, even though these actions were couched in a sort of “adorableness,” they slowly wore me down. They did harm to me, as he figured out what my weak spots were and what manipulative tactics he could use to convince me to do things that I didn’t want to do.

I was making out with some guy a few weeks ago, and the way he pushed his erection into me was painful so I said “that hurts a little.” He immediately, wordlessly, adjusted it and I remember being surprised. He genuinely seemed to not want to hurt me, and when he realized he was hurting me, took immediate action to fix it. This guy was very sweet; he was always looking out for ways he might be hurting me and trying to avoid them. I’ve been conditioned to expect that men will be indifferent to my pain, and if I am not always on guard they’re will hurt me through their indifference as they manipulate me to get what they want. But, I wouldn’t need to be so on guard with someone with genuine empathy. They might occasionally hurt me by accident, but they’re going to hurt me a lot less than someone who is aggressively trying to bend me toward his sexual will, no matter how ‘non-violent” that manipulation looks.

The trauma comes from this internalized hyper-sensitivity that makes it hard for me to connect with other people now. It’s hard for me to date men, because I’m always suspicious. Always on guard, always looking out for how their friendly actions might lead to my suffering. The fact that this ex boyfriend appeared so nice, the fact that no one warned me about him, makes what happened all the more difficult to process. I think there is a plague of fake niceness toward women in America, where men pretend to be nice, but are just trying to manipulate the women to do what they want.

And, this matters. It’s really bad for the women on the receiving end of it.

That’s not to say you can’t be up front about your sexual desires and request things (perhaps several times) from the people you’re dating. With my terrible “nice” boyfriend, when he wanted to have sex with me and I said no, he might say “Come on. Please? Pleeeeeease?” but that’s super toxic. He’s basically asking me to suck up my own discomfort for his pleasure, which is another way of telling me I am not as important as him. He’s telling me he doesn’t love me, he loves how he feels when he’s with me.

These are very different things.

What you should actually say, when trying to convince someone to do a sexual act, is “why not?”

Let’s say you’re trying to talk your girlfriend into anal sex, and she says no. And you say “why not?”

She may say “I’m worried it’s going to hurt.”

Then, maybe you can say “Yeah, I can see that. Would it make a difference if we used a lot of lube? Or if we researched ways to make it less painful on the internet?”

Maybe she says yes, maybe she says no but if you address her concerns and her reasons, that’s very different from just asking her to give in. That’s showing that you care about her lived experience. Thing is though, you have to actually care. You have to actually want her to have a good time.

If you knew your girlfriend was going to have a miserable experience during anal sex, would you still want to have it? (Notice I didn’t say “painful” — some people can have good and painful experiences.) However, if you know your girlfriend is going to come away emotionally damaged, scarred and hurting from doing something with you, would you still want to do it? (If you say yes, I hate you.)

Most people would say no, but many people would also be in denial about the pain they caused someone. All the guys saying “please, baby, please can we do anal” — they don’t understand the harm they’ll cause their girlfriend if she actually gives in. They don’t understand they’re dehumanizing her and objectifying her, and they also don’t understand they‘d probably be more successful if they didn’t dehumanize and objectify her. Ultimately, people will fight back against what hurts them. If you’re girlfriend keeps not wanting to have sex with you, it probably means she doesn’t enjoy having sex with you. You have to solve that problem before you can solve anything else.

Men aren’t really conditioned to see things from the woman’s point of view, and a lot of woman will obfuscate the truth around their desire — sometimes because they married someone they didn’t really desire for material security. Which is actually really terrible, and something I highly sympathize with straight men about (as someone who also sometimes dates women.) However, that’s not the focus of this piece.

The focus of this piece is to highlight how behaviors that seem externally similar can land very differently. Pressuring, begging, or manipulating a woman (or anyone) to have sex — with excessive persistence, threats, alcohol, anger, or any other means that ignores her emotional reality is likely to be traumatizing for her. The reason for this, is that you are pressuring her to do something she doesn’t enjoy so she can avoid some other negative repercussion. Or, to rephrase it, you are forcing her to choose between two unpleasant options: bad sex, or emotional blackmail/anger/annoying pestering/etc. Ultimately something that could be pleasurable (sex, romance, connection) turns into something that is associated with pain and discomfort. Eventually, it becomes unpleasurable. And, when previously pleasurable things become chronically unpleasurable, we have entered the zone of trauma.

Asking someone to have sex, and if they are reluctant, trying to understand why they are reluctant seems superficially similar. You are, in essence, trying to convince someone to do something you want them to do that they don’t initially want to do. But, it is unlikely to be traumatizing because you will either find a condition where both parties find the activity enjoyable, or if this isn’t possible, you won’t do the activity. Pressuring someone to do something they don’t want to do is abusive, finding the conditions that will help someone enjoy an activity you want to do with them is connection.

I wish I had understood this 20 years ago.


Note: some of these accounts have been slightly fictionalized to obscure identifying details about the people I was writing about.

Facebook: https://www.facebook.com/protectingthecrushed/ — Twitter: https://twitter.com/SassyDotLove

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