The Morality of Pretending to Be a Man in Order to Sleep with Women

There seems to be a big difference between the way Hollywood treats cross-dressing in order to fraudulently woo a lover, and the way the courts treat it. In Hollywood, when Dustin Hoffman or Robin Williams tried it and were busted, they ended up being cheerily reconciled with the object of their affections. Chastened perhaps, definitely a bit knackered after all that running between changing rooms, but not, as Wood Green Crown Court mandated last week, jailed for three years and put on the sex offenders' register for life. In Hollywood, that's not how you end a concealed-identities sex farce. In Nuns On the Run, Eric Idle's "punishment" was to avoid being killed by Triads and to gawp at convent girls in the showers. Tony Curtis got to do it with Marilyn Monroe. Even Ken Loach would make his version of Tootsie a bit more bubbly than finishing it by sticking an 18-year-old in the slammer for 36 months. But then again, there aren't many Hollywood directors who would write what seems to be the most common real-life climax in the pattern of these real-world incidents: the scene where the girl disguised as a boy uses a concealed strap-on dildo to penetrate the love of her life. Even Shakespeare balked at that one and he used to show all kinds of crass bullshit. There is no bit in Some Like It Hot where Jack Lemmon, still in a dress, grits his teeth as he is penetrated by a travelling salesman he recently met in a bar, his tackle taped cunningly to his belly. In Wood Green last week, 18-year-old Glasgow native Justine McNally's barrister pleaded with the judge for clemency: “This was happening to an unhappy and distressed female, at a time when any female can go through a confusing and distressing period, whatever their upbringing.” But no clemency was forthcoming and McNally was led away to the cells. McNally's extraordinary story had begun three-and-a-half years earlier, when she and her unnamed female victim were online-gaming partners. The unnamed victim thought she was playing with a boy called "Scott". She and Scott talked. And then they talked some more. For three full years. Inevitably, within this modern reconstruction of the Turing Test, romance bloomed. They got a bit dirty. They started talking about what they'd do to each other if they ever met. Much of the talk revolving, of course, around a penis that never existed.

But Glasgow is a long way from London, so it was only in March 2011, both aged 16, that the pair finally met. Scott came down to stay with a friend. They hung out. They went up Camden Market: being a bit of a goth seems to be an excellent gender-blurring device. The unnamed victim went out and bought condoms in anticipation of super-fun-times and then the super-fun-time came to use them. In 20-20 hindsight, the clues were there. Scott refused oral sex. Something teenage boys are not commonly opposed to on either moral or hygienic grounds. During their trysts, Scott did not remove any clothing. He told her he'd "just prefer to please her". They met again, in May and August, and Scott, with his baggy clothes, again managed to slip past the whole getting-naked bit.

Justine McNally arrives at court.

Inevitably though, things unravelled, and in spectacularly awful fashion. The unnamed victim's parents grew distrustful and, when a friend searched Scott's bag, they found a size-12 River Island top, a bra and the offending strap-on dildo (Prosecution Exhibit A). At first, the victim refused to believe that her one-and-only was in fact a crude construction of sawdust and papier-mâché and lies, but eventually she came round. Then the police came round. As with so much of this case, it's difficult to know whether it was comedy or tragedy that Scott/Justine then offered to continue their relationship after some gender realignment surgery. Last year's Scott, Surrey's Gemma Barker, was in a different league to McNally in terms of the remorselessness of her intent. Yet the beginnings of her case were also more Hollywood. Her boy personas came out of a conversation in which she asked her two pals what their ideal guy would be like. They compiled shopping lists of lush lad archetypes. And she, logically enough, went out and supplied their orders via her own imagination. Perhaps thanks in part to her resemblance to a pre-spliff Bieber, her pals fell for two of the three aliases that Barker conjured up. Incredibly, she kept her alter-egos separate merely by dressing them in different hats which she never took off. Soon enough, the dildo thing was happening but then Barker made the mistake of falling asleep after sex. Which might have been nothing more than pitch-perfect method acting had it not enabled her victim to peel off her hat. Without this foolproof disguise, Barker was rumbled and sent down for two and a half years.

Despite the shock value, it's difficult to piece together a proper moral from these tales of astonishing invention. The judge's moral in each was that the victim's trust had been betrayed and now they were going to have to rebuild their shattered lives. Hollywood's moral would be that if you just love someone enough, you can find a way to win them back. The judges both pointed out that consent wouldn't have been given if the victims hadn't been deceived. But stand-up comedians tell us that if full disclosure were necessary for lovemaking – if everyone had to stop pretending to potential shags that they liked Paolo Coelho or Coldplay or had only slept with five guys – then no one would ever jump in the sack with anyone. Put it another way: If you enjoyed having sex with a girl, but then became revolted when someone revealed you had sex with a girl, in the 21st century, isn't that a kind of reverse-induction homophobia? For all their ratlike cunning, Barker and McNally's subterfuge brings with it something from a very human place: a perversion of their basic need to belong. They wanted to join in with a sexworld that their basic physiology denied them access to. Whatever the morality, they represent the most extraordinary expressions of willpower most of us can imagine. Faced with going all the way from Glasgow to London to live night and day inside a deceit which could be rumbled at any second, even the most conniving horndog fratboy would say "Nah, not interested," and go back to the Xbox and the jazz sites. Yet McNally was prepared to do exactly that. Theirs were attempts to push back against the physical realities of the world in which they found themselves at an almost atomic level. They didn't agree with the definition reality had put on them and were prepared to go to any lengths to prove it wrong. For them, impossible was nothing. It's just that you wouldn't want to put their smiling faces on any motivational poster.

Follow Gavin and Marta on Twitter: @hurtgavinhaynes / @MartaParszeniew

Previously: Drug Etiquette for British People in 2013