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"Jill, try to relax your sphincter muscle as much as you can. It's really pretty hard to do but it's necessary to keep from being hurt. But are you sure you want to try?"Jill just rolled over on the bed. She rested her golden head on her arms while she brought her knees up under her body to get her ass high in the air. She asked if her position was right and Jan replied that it was perfect. Jan took the K-Y and smeared it around her asshole and used her finger to put it inside as far as she could. She was amazed to find that Jill was doing exactly what she had said by relaxing her sphincter.Bob had put a condom over his cock and Jan spread more K-Y over it. He went up behind her and put his cock in position. As gently as he could he tried to ease in. Suddenly there was a pop and he was inside her. He heard a gasp from Jill as she felt him penetrate her anus. He eased back and then moved forward again. It was as if his cock was in an extraordinarily tight prison. Jill asked him please. When we were at home she dressed in a very conservative manner seeming uptight all the time. The only exception was when we went on holidays when she would loosen up and wear bikinis and somewhat revealing clothes – not much mind you but certainly more than she did at home.We had discussed going to Key West for Fantasy Fest a number of times and looked at the information on the web. Karen was interested in the pictures of the men and women walking around in broad daylight with very little else on other than body paint, but said there was no way she would do that. Personally I thought she would be a hit, she has a slender figure, not overly endowed on the top but certainly enough to enjoy – a full B cup. Her legs and ass were her best assets and could easily have belonged to a top lingerie model.We finally booked the trip and left to see what it was all about. Our hotel was a couple of blocks off Duval Street where we knew the action was. We arrived there about 6:00 in the afternoon.
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