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HomeCharterSailing with Charlie: Randy O’Leary and The Gentle Art of Seduction

Sailing with Charlie: Randy O’Leary and The Gentle Art of Seduction

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Graphics by Anouk Sylvestre
Graphics by Anouk Sylvestre

Randy O’Leary was a likely lad of Irish descent and a single-handed sailor. Slim of waist and broad of chest, with a sing-song lilt to his voice and a shock of blonde hair, he had little trouble attracting the opposite sex. On the occasion of our story Randy found himself standing at the bar of the Mermaid Tavern talking to Commander Fownbottom of the U.S. Hydrographic Office. 

O’Leary and Fownbottom drank their way into a friendly argument on how fast each other’s yachts were and by closing time a race had been organized. O’Leary complained that he was a single-hander and thus would be at a disadvantage, but Fownbottom said he knew of a young lady who was dying to crew on a sailboat and Randy smiled and nodded with approval. All was arranged for the morrow and he was to meet the lady on the dock at 9am.

In the morning our likely lad, dressed in raggedy cutoffs and a bandanna, rowed to the dock in his pram dinghy, feeling somewhat hungover. He grabbed a couple of six packs of Heineken from the store and waited for his crew whom he had been told would be waiting for him. There was a nun out for an early morning stroll but no one else was in sight. They crossed paths several times as they wandered back and forth along the jetty until finally she struck up enough courage to ask if perhaps he had seen a yachtsman thereabouts who was looking for someone. O’Leary didn’t look anything like a yachtsman in her mind’s eye so she was quite taken aback when O’Leary, equally taken aback, said that he was that person. She had been expecting a smart young man dressed in whites with possibly gold epaulettes. He had been hoping for a well-endowed and tanned blue-eyed blonde.

Although Sister Mary was wearing a long white robe and a little white, folded three-cornered hat, she was certainly not ugly. Randy was not about to be put off by religious zeal and gestured Sister Mary towards his dinghy. She, though, was rather more cautious and it took quite a bit of persuasion and several mentions of Commander Fownbottom before she hitched up her habit and stepped precariously into O’Leary’s leaky dinghy. There was quite a stir in the anchorage from neighboring yachts. It wasn’t uncommon for O’Leary to be seen rowing young floozies ashore early in the morning, but a nun being rowed out at 9.30 in the morning was cause for much speculation, pointing, and passing of binoculars.   

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Soon the unlikely couple were sailing out of the anchorage. O’Leary’s boat, S/V Foreplay, was just ahead of Fownbottom’s Victory. Their course was to take them through a narrow channel and into a large sound before returning on a downwind leg. Mary (Randy had dropped the prefix Sister) explained that sailing had been a secret dream and that getting close to nature, the wind, waves and salt spray, was a way of increasing her devotion to God’s creation. Randy nodded enthusiastically and explained that nature was indeed wonderful, especially the procreative aspect. But as soon as sex was mentioned, Mary changed the subject. Randy managed to persuade our heroine to doff her protective habit and was surprised to see a curvaceous body, albeit modestly covered in a non too revealing black swimsuit. There was no question that Mary was devout, pure, virginal and dedicated – a life without sensual pleasure was the path she had chosen, a righteous path that would lead to eternal peace. O’Leary had a completely different philosophy and wanted all the sensual pleasure he could get … now. He had stripped down to the briefest of Speedo type swimwear. He grabbed yet another Heineken, sat close to his innocent crew, intending to seduce her with stirring sea stories. 

After a short time, something else began stirring and as Sister Mary turned she noticed a bulge in Randy’s swimsuit. She turned red as a beetroot, gave a scream and jumped off the boat. O’Leary, unthinking, tossed his beer over the side and jumped to the rail. He was midway through the narrow channel that marked the entrance to the sound. He desperately reached for the VHF radio when suddenly Fownbottom came on, “Where’s the channel?” he called frantically.

It took O’ Leary just a second to gather his thoughts, “Just leave the green can to port and the red nun to starb’d,” replied the Irishman … (And to this very day that rule applies in international waters when entering a channel from seaward.) 

Mary was picked up by Fownbottom. Her normal temperate nature succumbed to temporary weakness when she finally got aboard the Victory and in a moment of temper slapped the commander roundly on the cheek for his insensitivity at ever suggesting she go with the randy Irishman. During the ensuing fracas the commander veered out of the channel and ran aground.

O’Leary won the race. Commander Fownbottom lost a few more chunks from the bottom of his keel but all was soon forgotten and ‘splice the main brace’ was ordered by the illustrious captain of the defeated Victory.

Sister Mary returned to her convent and proceeded to write the ‘Rules of the Road’ for those girls choosing a life of abstention. No.1: Never, under any circumstances, go aboard a boat with a single-handed sailor. 

Secretly, though, she had never had quite so much fun in her whole life.


Julian Putley is the author of The Drinking Man’s Guide to the BVI, Sunfun Calypso, and Sunfun Gospel.   

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Julian Putley is the author of ‘The Drinking Man’s Guide to the BVI’, ‘Sunfun Calypso’, and ‘Sunfun Gospel’.

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