I’ve never been able to get my head around the cult of the MAMIL (Middle Aged Men – and women – In Lycra), with their ridiculous outfits, bad sunglasses and clip-cloppy shoes. It’s as if they’ve only just discovered the simple joy of riding a bike, and are yet to figure out you can incorporate it into your life as an unfussy, practical means of transport, without turning it into a pretend version of the Tour de France. But regardless of what I think, their numbers are increasing. As well as the faceless men and women who grimly glide past on my commute each morning, the cult now includes some of my best friends; people who should know better.

It all seems a bit mad, just like riding 300 kilometres and paying for the privilege. So when local boutique cycling tour company Soigneur offered an all-expenses paid ticket for a luxury weekend to South Gippsland, I agreed before I had a chance to reconsider. I wanted to understand.

THEY CALL ME BIG LEVERS – Specialized Bicycles kindly offered to loan me a carbon road bike and “kit” for the weekend, and invited me to attend a two-and-a-half-hour “Body Geometry Fit session” at the company’s Port Melbourne HQ.

After slipping into a padded lycra bib I was taken through a series of tests and measurements by Specialized’s resident fitting guru, Stew art Morton. I stretched in every direction, pedaled a stationary bicycle covered in adjustable dials and sat on a memory foam “arseometer” to measure, you guessed it, the size of my arse. Morton informed me I had “big levers” – something to do with the proportions of my legs, which meant I had a natural predisposition for cycling. After numerous adjustments, the bike I had been sitting on began to feel like an extension of my body. It was jet-black and expensive looking, and was to be my steed for the next 10 days.

After we left Specialized, my also-lycra- ready friend, Scottie, drove me to The Bike Gallery in Hawthorn. I was introduced to Cam, one of the owners, perhaps the most attractive man I have met all year. Cam helped pick out a few bits and pieces – a tyre tube, two pairs of socks, one of those funny little hats with the flip-up brims – for the coming week’s riding. I was as ready as I would ever be.

THE BIKE: A REVELATION – My first ride was like picking up prescription glasses. Everything was suddenly clearer, louder, more pronounced. The bike zipped and whirred while I was sleek and steadfast above it, my feet locked in as if I were piloting a fighter craft in a sci-fi movie. My own bike, so friendly and practical with its bright blue steel frame and lovingly worn Brooks saddle, was instantly rendered bloated and tiresome. I noticed other bike riders had a sort of disdain for me – not that I had much time to notice as I sped by on my futuristic machine. But waiting at the lights, I received none of the good-natured greetings I was used to on my regular commute. I was one of them now – a MAMIL.

HUMILIATION STRIKES – On the way home from a casual few laps of Yarra Boulevard, I happened upon a friend walking along the bike track in Carlton. I debated whether to say hello or remain anonymous – conscious that I looked like an enormous, bright-red penis. Or, you know, a middle-aged man in lycra. I began to wave, but while doing so, slowed to a halt and forgot to clip my foot out from my pedal and began tipping sideways. When my friend finally clocked me I was lying on the ground, still trying to disengage my foot. “Don’t worry, I won’t tell anyone your secret,” she giggled, even after I explained how I wasn’t really a cyclist and that I was going deep undercover for a story, like Matthew McConaughey in True Detective.

THE TRUTH ABOUT SHAVED LEGS– In an attempt to get under the skin of a MAMIL, I shaved my legs. My naked pins looked like a couple of old sweet potatoes; a pockmarked landscape of scars, bruises and varicose veins. They felt weird, and looked weirder. And as far as I could tell, it helped me in absolutely no way while riding. There are theories floating around regarding the merits of the leg shave, but as far as I can tell, the true reason is: the pros shave their legs, so you shave yours. It’s a show of commitment and singles you out as an enthusiast, rather than just a hobbyist. It’s a powerful thing to belong to a tribe. We’ve all shaved our legs in one way or another, literally or otherwise.

THE TEST – Daniel Strauss from Soigneur invited me out on an early morning ride a few days before the trip, starting in Kew. I texted him to see if I should drive there, to which he replied, “Up to you, I’d just ride though?” He added, “No worries if you can’t make it – kinda early!” I saw this for what it was: a test. So I woke at five, pulled on my lycra and rode like Batman through the dark, silent streets of Brunswick, all the way to Kew.

There were moments in the following hour when I wished I was anywhere but on my bike behind Daniel’s flapping high-vis vest. It’s that exercise feeling. The one you get after 15 laps in the pool, when every fibre of your being tells you to give up because this is hurting and you should stop because it feels like shit. Later, as we sat in a cafe, I explained that desperate feeling to Daniel. “That’s when you dig deeper,” he replied. “There’s always something more there.”

NO-ONE LIKES A WHINGER – Scottie and I drove down to Gippsland after work on Friday night, arriving to find most of our group draped across couches in the main communal area of the cottages we were staying in. While Daniel and Jason Blankfield (Daniel’s Soigneur business partner) prepared a huge, nutritious dinner, we compared notes and sussed each other out. We were a mixed bag. The group was, for the most part, made up of affable blokes aged 30 to 50, all of whom were cycling fanatics, but some with far more experience (and less leg hair) than others. My lack of experience released a pressure valve of sorts, and the group bonded, no longer viewing each other as opponents. I was to be the mascot. People kept telling me I was going to be fine, with a strange smile on their face. Later, Scottie told me not to worry and offered a piece of advice to help stay in everyone’s good books: don’t complain. “No-one likes a whinger, Maxi,” he said.

A WHEEZING ASCENDER – Riding in the pack feels lovely, being sucked along in each other’s slipstream while staying as close to the wheel in front as you dare. All I could hear was the whirring and clicking of the bikes. We talked a bit, but always in clipped sentences. As a car passed on an open stretch of road, Dave mentioned how satisfying he found it to drive past an ordered group of cyclists such as us. I told him I’d never thought about it that way. I usually just find it annoying.

The first climb caught me off guard. It was a pleasant, unsealed road, winding through a lovely patch of forest, which I will always remember as a sort of private hell. I lost control of my breath and became a wheezing squeezebox, pedaling madly in my lowest gear and trying not to cry. Eventually I made it to the top of the hill, where the rest of the group were waiting and cheering me on.

“You never stop feeling fucked,” Scottie explained later, “You just get used to feeling fucked. You look forward to it.” I thought of Daniel’s encouraging words from a few mornings earlier. “You’ll be fine, because you didn’t give up,” he had said. “That’s what I was checking for.”

I continued not to give up for the rest of the day. The van, piloted by our stone-faced mechanic, Fergus, along with photographer Andy Rogers, was always rolling nearby, tempting me with its motorised wheels and upholstered seats as we crept up yet another endless hill. I started using yoga breathing from the bottom of my stomach, concentrating on finding a rhythm between my breath and the constant rotation of my legs. Then I gave up on the breathing and began lying to myself. I told myself I would mention the yoga breathing in this article and I kept thinking about what I would write as I crept slowly to the top of the fucking hill.

The descents, while grim prophecies of future climbs, were also times of teeth-gritting tension. I was forever terrified of falling over, particularly on the dirt roads with their gravel patches and corrugations. I forced myself to loosen up a bit and let the bike have its head for some of a particularly winding section. “You’re a confident descender,” said Jason, who had assigned himself to the back of the pack, to keep an eye on me. I swelled with pride.

EAT BEFORE YOU’RE HUNGRY, DRINK BEFORE YOU’RE THIRSTY – Scottie had warned me of The Box, which is where you go when you become exhausted on a ride, and also of the Tin Man, which is who you become when you run completely empty. Scottie had become the Tin Man only the week before. “I was cooked,” he said, when I asked him what it felt like. “I fell off my bike and I couldn’t even think.” Scared of The Box and terrified of the Tin Man, I made sure at every stop to munch through a delicious molasses-brown slice (energy bar replacements made specifically for the trip by Fig and Salt) and pocket a couple of the strange, sweet-salty gels, that, once sucked from their foil, miraculously released much-needed power and positivity. I sucked merrily on the teat of my bidon bottles to wash it all down. And after the ride, we ate like kings – huge steaks with salad, potatoes and red wine. The food was all locally sourced and prepared by Daniel and Jason, as well as through several bakers and Sam Miranda Wines from the King Valley. I have carried this shameless eating regime into my everyday life. I imagine it’s like being pregnant.

THE PROM – I’d never felt as tired as I did after that first day’s ride. I had gone through several pain barriers and emerged, perhaps not stronger, but certainly more aware of how much I could bear. It seemed comical to even consider doing the same thing the next day, but come morning, I was feeling positive. “Why not?” I thought. After all, there were to be nowhere near as many climbs this time around. After a hearty breakfast, we set off on our shining steeds, which had been expertly washed and serviced by Fergus. The dirt track leading out from the property was quite severely corrugated in parts, particularly through a section we had named The Pit. Through The Pit, Daniel observed, your optical nerves could become slightly disconnected from your brain. It was highly unpleasant. The sealed road ahead felt like a blessing and as we made for Wilson’s Promontory, we settled into the two-abreast pack we had practiced the day before. I was able to appreciate the sights and smells of the landscape, seeing as I was now an old hand at this riding caper. We rode past a host of dead wombats, snakes and kangaroos, as well as pair of living emus. When we came to the first big hill, I was prepared. I found the right gear and settled into a rhythm with my breathing while the others rode ahead. It took ages to get to the top, but I was okay when I got there. Then we rode down the other side of the hill, revealing a glorious view of the ocean. I noticed I could appreciate the reward of the view this time, as opposed to the day before.

We stopped for morning coffee by a little stream. I was feeling very much at peace with the world and comfortable in my lycra skin. It was idyllic. But when we started riding again I realised something was off. My body had decided enough was enough. I frantically started eating my pocketed stash of muesli bars and gels to get me back on track–but it was as if my tank had sprung a leak.

IN THE BOX – The following hour or two were pretty full on. I was in The Box and the Tin Man was not far off. Everything felt helpless and much harder than it should have. It seemed the road was always running slightly uphill, even on the downhill sections. Gusts of wind threw me sideways, and when I stood up off my saddle to gain speed, my legs felt as though they were made of spaghetti. I began cursing Daniel and Jason for mapping the course so cruelly. I cursed Scottie for being so fit. I cursed Broadsheet for allowing me to do this assignment and I cursed myself for thinking it would make for an interesting story. I cursed a car by the side of the road, because it was red. I cursed the road and the stupid lines painted upon it.

Daniel and Jason took turns riding beside me and telling me encouraging things. “There’s just one more climb and then we’re home,” they told me. After what felt like years, I spotted a road sign with a picture of a hill on it. It does not bode well when you need a road sign to tell you about a hill. Right, I thought. Here comes the Tin Man. I tried standing up off the saddle again to get some speed. To my surprise, I could do it for a few seconds, and then I sat down again and prepared myself for the barrage of steepness. It came upon me, and I fell into the same rhythm I had found earlier. I breathed and I pedaled, breathed and pedaled. I had built it up too much – it was no different to any other hill. After I made it to the top, all I had to deal with was the stupid pit. I rode through it screaming, no longer scared that my eyeballs might fall out.

I could hardly believe it when we rolled into the property. I hadn’t become the Tin Man and I hadn’t got in the van. I had made it and I hadn’t whinged – if you didn’t count the last 50 kilometres in The Box. After a massive, sleepy lunch, we said our goodbyes and hit the road.

A SILLY IDEA – I was right – riding 300 kilometres over two days (not to mention the two kilometres of vertical climbing) was a silly idea. However, I’m extremely glad I did it. Although I had to return my beautiful steed, I ride my own bike differently these days. I stand up off the pedals to gain speed and I keep my gear low so my legs spin quickly. I even wear my lycra for my commute, and enjoy being laughed at when I clip-clop into work, padded genitals on display. The hair on my legs is growing back.

I knew this experience would be difficult, but I didn’t expect it to be one of the most rewarding of my life so far. It gave me a new appreciation for the men and women in lycra, and even inspired me to join their growing cult. “People say cycling is the new golf, and I hate that,” says Daniel, “but I can see how people think it’s silly, because the adventure is squeezed out of it.

Soigneur’s objective is ultimately, according to Daniel, “to share what the road bike can give you.” Which is what, exactly? Quiet resilience? Well, yes. That, and eating a tonne of food along the way. I get it.

Many thanks to Daniel and Jason at Soigneur for putting me up for the weekend, and Dave and Stewart at Specialized for the sweet ride. Head to soigneur.cc to book your trip.