Move over Richard Branson

Richard Branson’s got nothing on me when it comes to losing bets. The Virgin Group founder recently lost a wager to Tony Fernandes, CEO of Air Asia. Branson’s penalty was to don red lipstick and a skirt and serve drinks to passengers on a flight from Perth, Australia to Kuala Lumpur.

When I was married to my last wife, Kathy, we would embark on an annual winter sailing vacation somewhere in the Caribbean with our friends Rob and Yolanda. For the trip I'm writing about, we chose the British Virgin Island of Tortola as our starting point.

A couple of weeks prior to our departure, Rob and I were playing pool. He was normally a far better player than me but on this particular evening I managed to get the better of him. As I was closing in on my third straight win, Rob said, “I feel my luck changing. Why don’t we put twenty dollars on the game?”

Flushed with my success I ignored the danger signals and upped the ante, “Let’s make it more interesting," says I confidently. "How about the loser has to order a round of drinks stark naked at the Pusser’s Landing bar* during happy hour?”

Kathy, Me, Rob, Yolanda

Rob furrowed his brow in thought before agreeing with apparent reluctance. The bastard then proceeded to turn the tables and thrash me.

Two weeks later our boat is moored in Soper’s Hole and we're seated on the deck at Pusser's Landing. It’s happy hour and the place is packed. “’Bout time you got us a round of drinks,” says Rob with a wicked smirk.

My plan was to get close to the bar, whip my swim togs off, order the round and have my shorts back on before anyone spied my naked butt. But I hadn’t counted on Rob.

As soon as I got my gear off he stands up from our table and points at me. “Hey, that guy’s got no clothes on,” he yells. I hadn't even finished giving my order.

“I lost a bet,” I explained lamely to the bemused barmaid. By this time, all eyes were upon me. I finished giving my order then went to put my swimsuit back on. But in my haste, I managed to get a foot tangled in the fabric and had to dance around on one leg with the dangly bits flopping about while the crowd roared with laughter.

The only positive note was that the girls at the bar thought the floor-show warranted a free round of drinks.

*A wonderful waterfront watering hole in West End, Tortola.

Edited by Davina Chapman