Bareass Bet Loser
Dylan was an incorrigible betting man. He never had any money, but he could usually count on his good looks and charm getting him what he wanted. They worked especially well on the owner of the betting shop who seemed to have a soft spot for him and gave him extended credit time after time. When the debt got too big, he joked about putting the boys on him in the black room, but Dylan had a knack of picking big winners when he needed them most.
Inevitably, Dylan hit a losing streak eventually, and it coincided with a lot of other things going wrong in his life so he was already feeling pretty down when the bookmaker decided he had finally had enough and called in the debt. He escorted Dylan into his office and there, for the first time, Dylan met 'the boys'. Two, very ugly customers.
Dylan was terrified, he wasn't a tough or a street fighter by any means. His charm went into overdrive in a desperate effort to buy time. The bookmaker was patient, enjoying Dylan's performance and squirming, which always made him feel warm. Finally, he said, "I'll tell you what I'll do, Dylan. If you haven't got the money, I know two men who'll pay the debt for you".
"Wow!" Dylan squeaked, "Who?"
His jaw dropped as the Bookmaker gestured in the direction of the boys, who, with exquisite timing, theatrically produced wads of banknotes from their pockets.
"Now Dylan," the Bookmaker went on, "If you'll just accompany the boys into the black room, they'll tell you what you have to do".
The boys stepped forward, handed over their money and taking hold of Dylan's trembling arms, propelled him out of the office, along a corridor towards the back of the building, then down some steps into a basement room which was painted completely black. There they locked the door, seated themselves in comfortable armchairs and started to give him instructions to take off his clothes, starting with his shoes and working their way up.
Dylan hated undressing in front of other men, the only sport he enjoyed involved horses. But he sensed that if he cooperated, they were not going to beat him up. Fighting his nerves, his charm went into overdrive. Shucking off his jeans sensually and delicately peeling down his white underpants, he had their rapt attention. He was betting that stripping for them would be enough to pay off his debt. He'd give them what they wanted.
He was about to take off his hoodie, when they stopped him and came forward. "Very good Dylan" one said, touching his thigh, lightly, "you're certainly earning what we're going to give you". Another hand touched his bottom. "Now, see that padded couch over there? Just go and bend over it will you?"
Dylan had a sinking feeling, his losing streak wasn't over.
~
Go to Bareass No 93 (link pending)
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