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We were both quite excited to say the least and I had a permanently hard cock, thinking about what lay ahead. We talked about what we were going to do with her and both got more and more aroused. Things got a little more daring as the conversation went on. 45 mins later and there is no sign of her and we were both getting anxious.... A phone call later confirmed that she got lost, gave up and went home!I was absolutely gutted. I had fantasized for years about this moment, but it was not meant to be! Simon and I shared our disappointment, but the subject stayed firmly on sex. We continued to share fantasies. "Have you ever thought about fooling around with another guy?" I could not believe that those words came out of my mouth. I did stammer a little when I was asking the question. "Yeah, sometimes think about it...." I did not know how to handle what was said. So I went a little further. "My fantasy is to be submissive to another guy.... what about yours...?" I. I firmly grasped the base of the plug in my right hand and told her to relax and grip the dresser firmly. She did as instructed, relaxing as best she could. I took the tube of lubricant and using my fingers worked some in and around her tight asshole. Then I actually squirted some up her rectum. Lastly I lathered the plug with it until it was literally dripping. This was going to be an effort to insert and I wanted it to go as smoothly as possible.I marveled at the size of the thing, but it wasn't as big as me and I knew she could handle it.I waited for her to really relax."Take a couple of deep breaths and relax as much as you can, I'll be a gentle as possible, honest."She did exactly that, and I did as promised. I exerted a steady firm pressure on the base of the thing, but pushed it in very slowly. It was pretty erotic watching the black cone stretch her sphincter muscle wider and wider. By the time it was about 3/4 of the way in she was grunting and gasping, still doing her best.
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