It's 5pm on warm winter afternoon during Sydney's Vivid Festival and I am about to do it for the first time.
Well, everybody else I know has done it. Even kids as young as ten have beaten me to it, albeit with their parents on hand to witness the event.
I meanwhile, have been resisting for sixteen years, many of which I've spent here in the Emerald City, staring opportunity in the face.
It's become my personal giant grey elephant in the room.
"What, still not?" it insinuates every time I picture it, shaming my otherwise urbane character.
But now I'm ready. I've got my wingman Mike and a young bearded bloke called Graham has promised to show me the way.
First, I change out of my dowdy work clothes into something more comfortable. The blue and grey boiler suit and oversized jock strap aren't my idea of sexy but it's what everybody wears, apparently.
It takes a military-style operation and a small platoon to get me over the line. There are ten of us in all, including an Irishman, an Israeli engineer and two Sydneysiders celebrating birthdays, dutifully lined up behind leader Graham.
Then, like Jane Fonda and her Orgasmatron in the 1968 film Barbarella, we are shackled to the machine - a length of steel stretching into the distance - by our figure-scrunching jock straps.
It's the beginning of one of the rides of my life.
Shuffling up behind Graham, I begin mimicking his every move. When he goes up, I go up. When he pauses, I pause.
Soon we are outside. Darkness has fallen. There is a smell of barbecuing steak wafting up between cold, steel girders, an ominous thunder overhead, like we are mice trapped beneath a busy freeway.
In the dark we move stealthily, squeezing up between two commuter trains heading in opposite directions.
I quell the urge to yell out, look down at the churning wash of Sydney Harbour, 60 metres below.
"You can turn the lights on now," instructs Graham.
Suddenly, the bulbs on our fluorescent waistcoats are pulsing like a light show at a rave.
"Is it legal to flash on the Harbour Bridge?" quips the Irishman.
From on high at night, Sydney is a Koyaanisqatsi-esque blur of neon, arrowing skyscrapers split by twinkling rivers of traffic, beetling ferries and one remarkable harbourside confection of intersecting sails.
Tonight, for my first time, the Opera House is putting on a Vivid show. One minute its roof is a rainforest, the next a reef. One moment a large shark glides across it, the next it is a dissolving brick wall.
Now I feel high. The earth is moving beneath my feet but I feel safe, enveloped in darkness and the Orgasmatron's willing slave.
I've reached the pinnacle of my ambition and I'm beaming from ear to ear.
When we can get no higher, we slip our little fingers into the machine to monitor our heartbeats. Mine is going off like a stampede in a cowshed.
Tonight, following in the wake of more than 3.2 million others since 1998, including Oprah Winfrey, Prince Harry and 100-year-old Mrs Chris Muller, I've popped my cherry on the Sydney Harbour Bridge.
It's taken 3½ hours, 1332 steps and 16 years of prevarication but I've finally made the climb of my life, communing with a 1932-vintage coathanger, comprising 52,800 tonnes of steel and 6 million rivets.
And is it Sydney's number one must-do attraction?
The writer travelled as a guest of Destination NSW.
- FFX Aus