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She went back to the wardrobe, and this time I heard the familiar clank of a chain. When she returned to me, she held a short length of heavy chain with a snap-link at either end. She clipped one end to my collar and yanked me to my feet. She led me to the table, where I saw to my horror that she had scattered a whole boxful of drawing pins. A ring protruded from the wall at the back of the table. ‘Oh, Mistress, oh, no!’ I yelled, but it was to no avail, and she dragged my torso down onto the surface of the table, where the myriad little pins bit and stung into my tender flesh – pain from which there was no escape, as she clipped the other end of the chain to the eye in the wall. The pain was so awful I was scarcely aware when my Mistress came up behind me with a thin, supple cane, but I heard the ominous swish as it displaced the air, then felt the terrible searing sting as it ripped across the fleshiest part of my buttocks. ‘Oh, oh, oh, Mistress, please!’ I cried, and knew it was. And as a gift to myself, I decided to go on vacation! To San Juan Puerto Rico at that. Needless to say, my shopping trips leading up to the vacation were rather fun and expensive, but who cares! This is a once in a lifetime chance, and I wasn’t going to let it pass me by. Besides the obvious thrill of being able to dress when I want, go out when I want…. I also wanted a man for my vacation. At least one. So, a few weeks before going, I placed an ad on Craigslist to see if there were any businessmen there for a week. The subject line read “Your escort for the week”. Well, I got a ton of the usual “hey baby, come on down and suck my dick” or “let me pee on you” types with hairy beer guts and small cocks. After a few days I almost gave up checking. But luckily for me I gave it one more chance. An email popped into my inbox from a man named James. He was from Sarasota Florida and was staying at the luxurious La Concha hotel in San Juan on the same dates I was. Right down the street from.
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