The hour of departure at hand, it dawned on me that the Tour Pak secured to the sissy bar of my shiny new Sportster was as big as a sail. I admired my companions’ classic Harley cruisers, chrome pipes burbling with authority. “Nice little bike,” said one, adjusting his “Live to Ride, Ride to Live” skullcap, sun flaring off his earring, while the other, Bluetooth firmly inserted, checked our route on his fairing mounted GPS.

“I am privileged to ride with you, gentlemen,” I replied. Snapping shut the visor of my full-face lid, I punched the starter. The polite grumble from my pipes was drowned out by the roar of their Screaming Eagle kits. Whatever conceits I had held about my mount’s quickness and agility were shattered as they rocketed up the expressway.

My hopes of proving that size did not matter on the back roads would be dashed as well. As wind blasts from passing semis pounded my head and chest, shaking the bars and rattling the frame, the romance of naked bikes evaporated. I sang Johnny Cash’s “Folsom Prison Blues” to myself in an effort to find the strength to roll on the throttle and pursue my fellow travelers. I found consolation in the vistas of Lake Okeechobee, the serenity of Florida pine forests and the simplicity of cattle farms—while remaining vigilant for cow pies that might compromise my traction.

Thanks to the Sporty’s peanut tank, gas stops were frequent and merciful pauses. I watched the increasing flow of bikers converging from all points of the compass. Leather-faced chopper pilots mixed with Cordura-clad couples on trailer-hauling Gold Wings. Seven hours later, we pulled up to The Last Resort, just south of Daytona—a congregation of hardcore Harleyites and weekend wannabes. My teeth rattling, I gulped a cool Bud to mitigate the effects of wrestling what had felt like a 500-pound motorized dumbbell. “You’re a trooper, man. Riding that peanut bike all the way here and actually keeping up with us,” observed one of my riding partners. I would be known as “Peanut” for the remainder of the weeklong festival.

It was also decided I needed to trade my “girl’s bike” for a more serious touring machine. For, as I followed gamely along for the rides that took us by the hundreds through Daytona’s most revered riding routes and meeting places, I felt like the schoolboy in high-water pants. I was certain the eyes of the half-million bikers who had come here to worship were distracted by my obvious deception at having a machine I had already outgrown.

Relief came on the last day. A dealer friend offered me a big Japanese tourer for the ride back. At first taken aback by its mass, I soon understood it could actually make me look like a better rider. When my companions’ trophy girlfriends agreed, informing me that “real men ride big bikes,” the testosterone surged through my veins. Erect and unruffled, I guided my steel stallion like a Hapsburg cavalier upon a Lipizzaner. I caressed the grips as the bike carved laser arcs in off camber curves. Straight-aways became launch pads as we zoomed past the century mark. The windscreen became a window to a new world of motorcycle bliss. The motorcycling gods smiled, as the sun set over Daytona.