We had agreed via email that neither one of us was one for small talk, and he wasted no time. He pulled out a gimp mask from his holdall and put it on me, then reached in once again and pulled out a cock cage. I liked the idea of this as i had never used one before, he put it on me and told me to remove my dress and go and lie on the bed, I was beginning to realise i was in for a fun night. He then told me to put my arms up above my head and keep them there. I did so while he undressed at the end of the bed while i watched. he laid next to me and grabbed my balls and squeezed incredibly hard, i pulled my arms down to grab his hand but he grabbed me by the neck and to me to put them back up or he would squeeze much harder, so i did. He then said, if i move, if i make any noise this would just be the beginning of my punishment. I nodded and he released my balls and began stroking inside my thigh with his right hand and with his left began softly playing with my nipples. This was a HUGE. It was a Friday, and I would be traveling home to Connecticut the following day on the train. We left at four o’clock and hit a small intimate bar called the Ivanhoe. It had a dark interior and was relatively quiet on a late-summer Friday. We had drinks and talked girl-talk and exchanged promises to keep in touch. By seven, only Claire and I were left. I had nowhere I needed to be, and no man whom I wanted to say goodbye to or ever see again. I was feeling pretty down on men after a summer of brazen uncaring studs. They had been fun, but truly worthless.Claire was drinking a little too heavily. She became morose and began telling me about her two failed marriages, and the children she never had. By eight, she was crying into a martini glass and explaining how lonely life inevitably was unless you were willing to play second fiddle to some man. I saw the other side of Claire’s life. I had been looking up to her all summer, and now I was feeling sorry for her. At nine, I poured her.
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