Photo by Caroline Brady

Dear Roe, I’m having a bit of an issue with my boyfriend, which has also led to a debate with a friend. I’m 24 and have been with my boyfriend for nearly four months. I was with my last boyfriend for two and a half years and we had a really good sex life. One thing my ex really enjoyed was me putting a finger in his ass (sorry that’s gross to write) while I was giving him oral sex. I’ve heard most men enjoy this too, but my new boyfriend won’t let me at all and thinks it’s weird and “a bit gay”.

I’ve been trying to convince him to let me do it once, because I think he’ll enjoy it, and I really want sex and oral to feel as good as possible for him, but he still refuses. It’s frustrating for me because I love making my partner feel amazing and like feeling like I’m amazing at giving oral! But when I was telling my friend about this and asking her advice on how to get my boyfriend to let me do this for him, she said I was pressuring him and it wasn’t fair.

I don’t feel like I’m being mean or pressuring him in a bad way, I just want our sex to be good! But now I’m worried that she’s right and maybe I am being horrible trying to make him do something he’s not interested in. Should I stop asking him to try this? If a partner say no once is that the end of the discussion?

Dear Letter Writer, the party line first: yes, it is a general life rule that you shouldn’t pressure anyone into doing something they’re not comfortable with. It’s their body, they get to decide what happens to it and when and with whom, and of course no means no. (Do you hear that, psychopaths who will try twist the following into an excuse to ignore consent? NO MEANS NO.)

In reality, however, people pressure people all the time to try things sexually, and (as ever) the important thing to remember here is context and degrees.

There is a huge difference between someone maliciously pressuring someone to perform a sexual act they’re not comfortable with, and a respectful partner gently pushing you to open your mind and broaden your sexual horizons.

The former is abusive, intimidating and bullying bullshit; the latter is really more begging or nagging than pressuring, and is often a necessary opening step in the process of exploration and negotiation that will determine what sexual acts you and your partner explore.

Bearing in mind that there are very obvious exceptions – physical pain, emotional trauma, serious aversion, etc – the reason there is leeway when it comes to nagging your partner (to an extent) to try certain acts is that healthy sexually active relationships come with a certain degree of presumption regarding sexual acquiescence and exploration.

You want a healthy and fulfilling sex life with your partner, and sometimes you’ll have different ideas of exactly what that means or how you’ll get there.

You may have tried something your partner hasn’t, or be interested in something they’re not. And just like most people will have turned down various offers or opportunities for sex with their partner only to have sex with that same person down the line when they felt more comfortable, sometimes people will balk at the idea of a sex act or not feel ready for it, only to change or open their minds down the line.

People need to be introduced to new ideas somehow, and the more they hear how normal or enjoyable acts are, the more likely they’ll be to try them.

This is how people with kinks often have to approach their partners: initially hinting at their desires, asking for them outright, explaining why it’s important to their sexual satisfaction to have them indulged, addressing any questions or concerns their partner may have, proving themselves to be respectful partners committed to fulfilling their partners sexual needs – and then asking again, hoping that this time their partner will be willing to try it.

So the nature of this “pressure” lies in the intent. It’s sharing, not shaming, exploratory, not intimidating. It’s not disrespecting someone’s refusal to engage in a sexual act, it’s acknowledging (and hoping for) the very real and common possibility that their refusal might not be indefinite.

Yes, no means no – but it doesn’t always mean never.

Will this repeated request approach always work? No. First of all, if you’re a dick about asking for it and make the jump from respectfully bringing up the subject to obnoxiously demanding it, your partner may (and should) rightfully shut you down forever.

Also, everyone has their personal limit to what they’ll try. If you’ve tried the gently nagging approach and they still won’t budge, there will come a time where you’ll have to accept that you can either do without that sexual act, or do without them.

When or how you make that call may well depend on the reasons your partner gives for refusing to try a sexual act, and how you address their concerns, which should include taking them seriously, giving them information and showing them the potential for pleasure – and then backing off if they still aren’t into it.

Which brings me around to your boy, his aversion to anal play, and whether you should keep pestering him. I’d say nag for a bit longer, but nag a bit smarter. Your boy’s insistence that a man enjoying anal play is “weird” and “a bit gay” (sigh) is a very common fear, stemming from a clichéd straight-guy fear of being emasculated. And this fear can be assuaged.

First of all, tell your boy that people have sexual orientations – but sexual acts don’t. Acts don’t indicate a particular sexuality; the desire behind them does. So there’s nothing “gay” about you fingering his ass. (Well, as long as he’s not picturing Clive Owen as you do, in which case you may need to be having a very different chat.)

Second, fill him in on the biological reason he’ll probably enjoy it, because unless you’re Sarah Palin, it’s hard to argue with science. The prostate is a walnut-sized gland that is situated under the bladder, behind and just above the base of the penis. It’s extremely sensitive to stimulation and can increase the intensity of orgasm and amount of seminal fluid ejaculated. It can be stimulated by massaging and placing pressure on the perineum (the skin between the balls and ass), but it’s much easier to massage the prostate by inserting a finger or dildo into the anus.

Third, prove to him it’s completely normal by showing him the hundreds of millions of articles on the internet (especially from typically “macho” lads’ sites) that have guys talking about how great it feels.

Fourth, tell him it’s referred to as the male G-spot and refusing to let you stimulate it is about as stupid as telling him he’s not allowed touch your clit.

If he still won’t budge, it’s going to be your call on whether you can do without this anal play – which, by the way, you really can. If you can deal with that, fine. If you can’t, consider if you need to be with someone whose sexual ideals lie closer to your own.

But if he does agree to give it a go, result! Have a look at my column on safely navigating anal play (spoiler alert: there’s a lot of talk about lube), and enjoy the fruits of your nagging labour.

Dear Roe, twenty-five-year-old Galway girl here. I know you’ve written a little about open relationships before so I wanted to share this with you. It’s become a bit of a clusterfuck for me, and hopefully my story could serve as a bit of warning to non-monogamous people who believe their usually monogamous partner when they say they’re fine with trying non-monogamy.

I started going out with one of my best friends, who knew that my last two relationships were open. He said he wasn’t particularly comfortable with it, but that he was so crazy about me that he would try to adjust. Stupidly, I took him at his word, and after we were together about three weeks, I went out with my friends for a girls’ night out and ended up going home with a guy I met.

When my boyfriend found out, he was so angry and shaming, asking what was “wrong” with me and saying I was a horrible person. We broke up, him furious with me but also me furious with him for claiming he could deal with it and then shaming me when I was always upfront. Just shows you the importance of not pretending to be comfortable with something you’re not.

Dear Letter Writer, there actually isn’t a question in here, which is how this whole column thing generally works, but hey, you don’t like playing by the rules, ya big maverick. So let me answer the unasked question, which is what do I think of this situation.

I think you acted like an asshole.

And it’s the kind of assholish behaviour that particularly pisses me off, because when it comes to stigmatised groups like non-monogamous people or kinksters, shit like this just feeds into other people’s prejudices against them.

Basically, you and your bullshit moves are the very reason people are wary of open relationships and think all non-monogamous people are selfish and disrespectful and untrustworthy – all labels that, while most definitely not applicable to the actions of all non-monogamous people, are wholly applicable to you in this situation. You, my dear, are ruining for it for all of us, and need to cop on – immediately if not sooner.

Your letter is sketchy on details. For example, how did your boyfriend “find out” that you had sex with someone else? Did you tell him, or did someone else? When? It’s all so very dodgy.

From what I understand, though, your boyfriend was clear that he wasn’t comfortable with non-monogamy, but was willing to work on it. He was willing to try something new – and something major, at that.

Monogamy is such an ingrained part of our culture that there’s a huge amount of emotional baggage tied into it. We’re taught to believe that love is meant to be given to one person, that we’re all destined to find The One, and that they’ll fall head over heels for us, and monogamy will just come naturally. And so, implicitly, we are sadly taught to equate the success of our monogamous relationships with our value of ourselves.

So for your boyfriend to recognise that in himself, to acknowledge that he isn’t the type of person who can immediately say “Go forth my love, and fuck other men, and it will be all good!”, to know that non-monogamy would probably – at least at the start – cause him all kinds of insecurity, jealousy, doubt and hurt, but to still offer to try navigate that messy riverbed of emotional baggage just for you?

That is a huge deal, and one of the biggest prices of admission a person can pay to enter a relationship.

And you, my dear, frankly shat all over it.

There was no meeting him halfway, no conversations about what he was comfortable with, how you could both ease into this arrangement, what you both needed. I can tell by the fact that he was hurt and you were surprised.

You say that he knew you were non-monogamous and so he should have been prepared for you. But you knew he was monogamous, and refused to even acknowledge the need to be prepared for him.

You weren’t willing to contemplate the fact that he would need to be eased into this slowly. You didn’t put in the necessary special effort to show him that you were a trustworthy and respectful partner who would do her best to make him feel comfortable and safe before playing around.

You knew he wasn’t comfortable, but you refused to do anything to get him there. It was your way or the highway, and that’s just bullshit.

Also to debunk any defences of high sex drives and the need to be fulfilled before you start angrily writing in – three weeks is not enough time to justify any claims of being sex-deprived enough that you needed to have sex someone else. So no sex-based defences, other than you just wanted to have sex with someone else and didn’t care if it hurt your boy.

Which it did. Because of course it did. Because you weren’t in an open relationship. You were in a relationship with a guy who expressed an interest in exploring non-monogamy down the line, and you cheated on him.

I’m being harsh for three reasons.

One: because you acted like a knob and you deserve it.

Two: because I want you to learn from this. I want you to find a great relationship, monogamous or not – and to not mess it up this time. So next time, be considerate and respectful of your partner and maintain a constant dialogue about exactly what the other wants, what you both consider to be acceptable.

Three: I repeat, there’s a lot of stigma out there. And this shit isn’t helping. Monogamous people get to mess up and act selfishly all the time and not have their actions act as a reflection of monogamous people as a whole. Non-monogamous people aren’t there yet. It’s a minority group, and one facing a lot of prejudice and misunderstanding, and you bet your ass that people will pounce on any example of shitty, hurtful behaviour to condemn every adventurous kinkster or group player as morally corrupt, unethical deviants. So for the sake of the reputation of non-monogamous people everywhere, don’t be a group player until you can be a gold-star group player.

Now go profusely apologise to your boy, and if you both get back to even a friendship, be sure to respect it this time.

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Roe McDermott is a journalist, arts critic, Fulbright awardee and sex columnist from Dublin. She lives in San Francisco, where she's completing an MA in Sexuality Studies.

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