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We only slept together that first night before catching the tide north. Apart from brief spells, one of us had to be at the wheel at all times and when Tranquillity was steering herself, someone had to be alert for any problems. But there was no doubt that the kiss before she left made me wonder.All that aside, I had plenty to do; not just exploring the town and entertaining myself, but restocking supplies and checking over the condition of my boat. By Sunday morning, though, I was ready to move on. High water ... eleven-thirty. I was up and about by seven, fed and coffee’d satisfactorily, and trotted along to get a shower. On the way back, I passed a girl, maybe late teens, ear-buds in and an audible tinny beat perceptible. I paused and listened – not to her Ipod, but to the raucous cries of the gulls, a robin, not visible but not too far away, the wind in the trees and the sound of the sea against the outer walls of the harbour. I shook my head and carried on. Before anything else. Maddie must have interpreted it as ‘more,’ since her next word was, “Fifteen... Wow. I think we’ll stop here for a bit, my sexy little anal whore!” Her pet name made me smile and blush at the same time. She put the squeeze bulb on my abdomen reached down to fondle my scrotum. My squirming continued as even subtle movement of the huge plug in my ass was enjoyable. “Sweetie, I’m going to leave you here for a moment while I go to the bathroom. You might start to feel a bit uncomfortable with the plug inflated that large, but it won’t injure you. It’s getting you ready for what’s coming next.” She gave my scrotum one last tug and then went to her suitcase. She pulled out something red, black, and lacy and disappeared into the bathroom. The next five minutes started off as glorious. The new discovery of anal pleasure coupled with being bedded by the woman of my dreams. Glorious quickly became a feeling of fullness, which degraded to pressure, which then became induced cramping. “Ugh.” I.
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