My evening pretending to be a woman

I have a friend who describes me as an ‘“uptight boring old straight heterosexual” — simply because I don’t use porn or prostitutes, don’t swing both ways and have no interest in orgies and dogging, or any desire to be tied up and flogged by some fat dominatrix in a “torture den” in Pimlico.

He is always on the lookout for a new kink or a fresh fetish to try, and one of his latest passions is autogynephilia — that is, experiencing sexual arousal at the thought or image of oneself as a woman. This means he can find a woman sexually attractive only when he thinks not of her but of himself as that woman. He used to call himself a transvestite; now he calls himself an autogynephile.

Autogynephilia (or AGP for short) is a medical term coined by the psychologist Ray Blanchard in 1989. But it has recently become both a fashionable practice and politically controversial. I think its current appeal — at least for my friend, who loves to provoke — is that you can shock heterosexual males and offend the trans-activist community at the same time. The latter believe that the very idea of autogynephilia is intrinsically transphobic.

I confess that it’s hard for us straight males to understand the appeal of AGP. One self-confessed autogynephile has said on YouTube that he couldn’t have sex with a woman “unless I imagined myself as that woman.” This sounds like a form of erotic narcissism to me.

Of course I’ve often thought about what it must be like to think, act and experience the world as a woman. Most men, I suspect, have. But getting aroused by thinking of oneself as a woman? I don’t get it.

I said to my friend: “Where’s the thrill in that?”

“Well, why don’t you try it?” he replied.

My first reaction was “No way,” but then I thought “Why not?” I’ll show him that we uptight straights can try new things. As Sir Thomas Beecham allegedly said, you should try everything once except incest and folk dancing.

My friend offered to be my guide to the joys of AGP for one evening. We began with getting in a feminine mood. This involved pink champagne, two episodes of Sex and the City and watching him parade around his living room in a variety of — supposedly — sexy lingerie.

He suggested I slip into something more comfortable, and offered me a silken kimono, lacy underwear, a red bra and a pair of high heels. Like any good heterosexual, I began to perspire with fear — but like any good liberal-minded man I was determined to show no fear, so I got with the program.

“Now, don’t those clothes feel so sensual against your body?” he asked.

Yes, they felt soft and nice.

He then told me to shut my eyes as he caressed my face with a scented silk scarf.

“How’s that?” he said.

I had to admit that was something more than nice. A tiny spark of something had been lit. Was it just the power of suggestion or was I — gulp — becoming an autogynephile?

But the spell was broken when he said: “Now very slowly, I want you to caress your breasts as if they were a woman’s breasts.”

I awkwardly fumbled my chest area and he asked: “Do you feel anything?”

“Yeah, I feel a right tit.”

He didn’t laugh. But then people with a serious sexual fetish never have a sense of humor about it.

He carried on trying to get me to feel my body as the body of a beautiful sexy woman. I will spare readers the details of his masterclass in “getting to know and love your nipples” and saying “hello” to my imaginary vagina.

Next he sat me down in front of his make-up mirror: “Now, what sort of woman would you like to imagine becoming?”

“Penny Mordaunt please!” I replied.

On reflection, though, I decided she was too young and chose the more age-appropriate Helen Mirren.

“Right, let’s get to work,” he said. “Relax and shut your eyes.”

First I could feel a wig being placed over my head and then his make-up brushes doing their magic. Sitting there undergoing my transformation, I felt like a contestant in that old TV show Stars in Their Eyes, where some ordinary person said, “Tonight Matthew I’m going to be Cher” or some other famous singer — before vanishing into cloud of dry ice to reappear transformed into their favorite star.

Eventually my friend said I could open my eyes. I was meant to see myself as Dame Helen Mirren and be thrust into a state of arousal. Alas, I looked more like Dame Edna Everage and was thrust into a mild depression.

But you know how you don’t want to hurt the feelings of the person cutting your hair when you’re horrified by the results and you fake a smile and compliment them on their work? So I said, “Amazing. I feel so… so…”

“Aroused?”

“Yeah, I’m getting there!”

“What you need, my friend, is another drink and a spot of porn.”

Of course, my friend was into retro porn — the stuff from the 1970s and 80s. As we watched he kept telling me to imagine that I was the woman on the screen getting serviced by the plumber or the washing-machine man.

He was clearly turned on and I was clearly turned off. Why? Here we were on Saturday night, two old blokes dressed up as women, seeking sexual thrills by pretending we were women. What a strange world, and what a sad life some of us lead. Still, I’m glad I gave it a go and can add autogynephilia to my list of things that are not my cup of tea.

This article was originally published in The Spectator’s UK magazine. Subscribe to the World edition here.