Photo by Caroline Brady

Dear Roe,

I’m a 26-year-old woman and have never really been able to orgasm through intercourse. I’m not worried about that as I can get off in other ways, like getting oral or being fingered etc. My problem is that I’ve recently started seeing a new guy, and he’s all about having simultaneous orgasms, and has told me that hearing a woman orgasm really turns him on. Now during sex he’s constantly asking me if I’m about to come, and telling me he won’t unless I do – it’s exhausting! I hate the idea of faking orgasms but should I just do it?

Dear Reader,

Excuse me one moment while I address the men reading.

Dear Men,

Seventy-five percent of women will never orgasm through penetrative sex alone. NEVER. EVER. DO OTHER STUFF.

Dear Reader,

Back to you. I’m glad you’re reluctant to fake orgasms.

Far too many women do, and it reinforces the all-too-common belief that most women get off from penetrative sex alone, which then causes this horrible cycle of men believing that they don’t need to do anything else, and that women who are honest about not being able to orgasm through sex alone are somehow weird or damaged.

Also, pressuring someone to have an orgasm is incredibly counter-productive, and your boyfriend needs to be aware of that.

So, I think you need to be honest with your boyfriend, and tell him that pressuring you is annoying, and that if he really wants you to orgasm, he’s going to need to manually stimulate you at the same time – or let you play with yourself and/or use a sex toy while you’re having sex so that your orgasm is real. And if ye can’t quite get the timing right, he’s going to have to get you off before having full-on penetrative sex, and just get over his need for you to come when he does.

However, I’m also going to throw him a bone (pardon the pun). Many men do find the sound of women having an orgasm to be a huge turn-on, and sadly, thanks to society’s messed-up ideals of masculinity and sexual performance, hearing a woman orgasm lets many men feel like they’ve “done their job”, and allows them to finally relax and orgasm themselves.

This isn’t an easy mindset to get out of, and so if your boyfriend really needs to hear you orgasm to do so himself, how about occasionally (only occasionally), you compromise?

Your boyfriend needs to finger you, go down on you, use sex toys with you until you have an orgasm (or five.) Then have penetrative sex on the understanding that you’re going to throw in some moans and writhing and “oh my Gods” when he’s about to come – to fulfill his fantasy of simultaneous orgasms.

You will remain very clear with him about what actually gets you off and when you’re deliberately indulging his ego, so he’s under no illusions about what makes you orgasm.

However, in the moment, he gets to live out his fantasy and enjoy the fairy tale that his magical penis has sent you into ecstatic waves of pixie-dust pleasure but can never honestly say “My girlfriend LOVES this” and perpetuate that myth, because you’ve been clear about the truth.


Dear Roe,

I’ve been finding phrasing this question tricky, because I don’t want to sound like I’m condoning what I’m about to address. I know Milo Yiannopoulus is a horrible bigot and his comments about older men and younger boys were disgusting. But I also know a lot of gay men who did have relationships with much older men when they were still teenagers and don’t seem to regret it or feel damaged by it. I think age of consent laws are really important but was Milo tapping into something that does actually happen a lot?

Dear Reader,

I understand your wariness around asking this question – any statement that seems to align you with Milo Yiannopoulus should rightly be approached with extreme caution.

For those unaware of Yiannopoulus’ comments, the controversial figure seemed to condone paedophilia, saying boys as young as 13 can consent to sexual relationships with older men; that sexual attraction to “sexually mature” 13-year-olds is not pedophilia; and that sexual relationships between young boys and older men can be “hugely positive”.

In Ireland, these statements probably seem familiar, as Senator David Norris made a similar argument – albeit in a historical context – in an interview with Magill magazine in 2002.

Now, let me be absolutely clear: I do not, under any circumstance, condone any sexual activity between adults and minors, and I think Yiannapoulous’ comments were irresponsible, disgusting, and deeply damaging to the LGBTQ community, who still face discrimination due to stereotypes regarding predatory behaviour.

As I’ve written before in my column on transphobia, these arguments are the driving force behind the trans bathroom debates.

But I do think there is something worth discussing in the issue you have raised, dear reader, in that I too know a few gay men whose first sexual relationship was with a much older man.

One of my friends was very clear that he knew intellectually the relationship was wrong, and looking back feels deeply critical of the older man who approached him. However, he still says the relationship was important to his own personal and sexual development.

This phenomenon, to me, isn’t indicating that a) these relationships are right, or b) that a disproportionate number of older gay men are predatory – there are many, many more wonderful, ethical gay men in the world, and besides, talk to any woman (including me) and you’ll get an abundance of stories about older men creeping on them when they were teens.

Creepy older guys sadly just exist; their sexual orientation has nothing to do with it.

What these relationships are indicating is the lack of community and options for sexual expression for gay teenagers. Many young, gay teens face a barrage of homophobia at home, in school, in their community, in their church if they have one, and from society at large.

This can prevent them from being out, so sometimes gay teens aren’t aware of each other, and can be left feeling isolated, alone, and unsafe – and unable to experience all the romantic and sexual exploration that many of their straight peers can.

Gay teens also don’t have a wealth of real-life older role models to choose from, which can prevent them from benefiting from the example and wisdom and reassuring presence of older people like them, that straight kids just enjoy personally and through osmosis.

Facing this isolation, the community, safety, reassurance and sexual experience that seems to be on offer by some older gay men could very understandably seem appealing.

This doesn’t mean, of course, that these relationships should just be allowed; the power dynamics are completely off and could be deeply damaging.

But by examining why gay teens could be attracted to these relationships, we can realise what absences in their lives they’re responding to, and learn from that, offering them more support.

We can acknowledge the damage and isolation that homophobia and heteronormativity induces in gay (and lesbian, bi, asexual, trans) teens, and work to ensure that they feel safe and supported.

We can help them find communities that understand what they’re going through, and offer them spaces to not only connect with peers, but mentors and role models with whom they can form respectful, appropriate relationships.

And we can acknowledge how homophobia prevents some gay adults – particularly those in certain professions or industries – from being out, and how harmful that is to them, the LGBTQ community at large, and young gay people who are losing out because their community is not being represented.

Milo Yiannopoulus is a thoughtless, irresponsible, bigoted fool. And like many of his statements, his flippant apparent condoning of statutory rape is to be condemned.

However, like many thoughtless, irresponsible, bigoted fools, he also offers us the chance to examine not what he’s pointing at, but the complexities he’s choosing to ignore, and to transform something ugly and damaging into a pathway that allows us to support those who have been left feeling marginalised, ignored and unsafe for far too long.

Do you have a question for Roe? Submit it anonymously at

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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