Oh, she had tried. Big vibrators, small vibrators, dildos, her fingers, her hands, Chinese love balls, a carrot, a cucumber, a toothbrush.
Her problem? The mistaken belief that a man would one day give her one, like a gift he'd bestow upon her for allowing him to deflower her. Not to mention her tragically misplaced conviction that she would not know an orgasm until she had experienced it during intercourse. You can imagine my reaction.
I looked at her with a steady eye laced somewhat with incredulity, drew my chair closer and said the only thing I could summon from the depths of my experience.
You see, at that point I thought she was an oddity in a world of sexual beings. I thought the majority of women were like me. Little did I realise that many women still don't:
a) have a sense of their own bodies, and
b) know how to please themselves.
Which makes sense really.
Because while guys grow up comparing willy size and wacking off around each other (not homoerotic at all of course), girls are born – and often remain – strangers to the happy bits that are tucked away between their legs.
I've come to understand that the closest a lot of women get to an intimate knowledge of their vagina is how they wax the pubes around it or whether it stretches after a baby pops out. And while many women might enjoy sex (with or without the orgasm) few actually know how to pleasure themselves.
This is a pity really, because there's nothing quite as lovely as a good, solitary wank.
There might not be any cuddling after, but let's face it, pillow talk is over-rated. Maybe it's just me, but after a toe-curling orgasm, the only conversation to be made should be about how to obtain tea, champagne, chocolate or sushi. That not forthcoming all I really want is a little re-energising snooze.
But I digress, and the pillow brings me back to my friend.
"First off," I said, "you need to throw out all the Cosmo drivel about sexuality that makes a competition out of pleasure. That harder than hardcore, practically macho, I-fuck-like-a-porn-star-and-can-get-myself-off-with-a-paperclip-if-I-have-to idea of sexuality. This isn't boot camp."
"Second, get rid of the toys. And forget your hands for now. Wedge the corner of a table or (lying on your tummy) a pillow between your legs, and let your hips and imagination do the work. I had my first orgasm in much the same way when I was 10. But that's a story for another day.
The point is, there's a lot that a little friction and your fertile mind can accomplish without the bother of stumbling over dildo or finger technique. After all, no-one uses a skipping rope to get to the finish line. Once orgasming becomes second nature and you're over that 'hurdle' you can start introducing the props."
"And then third," I told her, "become better acquainted with your vagina. Get a mirror, lie on your back and really appreciate what a beautiful body part it is. Explore the wonders of ice."
Now I realise that many of you, as the divine sexual beasts that you are, will be pooh-poohing my sermonising as irrelevant and outdated.
But think of it as a public service announcement for those who've never embraced the 'down there'. After all, it's not as if it's a conversation broached often or honestly over dinner tables.
Then again, maybe it's a just a chocochino thing.
Follow me on my blog here or on Twitter here.
Or what do you think? Do you have a relationship with your bits 'down-under'? Let us know in the box below.