When she awoke it would be ass time. I put a small dildo on the machine and gave it good lubrication. When she awoke I started the machine. She had never had anything in her ass before and pleaded not to do it. I told her that was part of the sexualness that she had to learn. We will use larger and larger dildos both for her ass and pussy until finally she will be able to take any size. She said it hurt. It will for a little bit but it will stop when you are big enough. While that was happening I whipped her back 10 times so that she would start getting used to the pain. I left her for about an hour and found her have orgasms from the ass. She was loving it. I let her relax for a while. Then I turned her over and put tight clips on her nipples and paddled her pussy. She was crying as it hurt. I told her at the beginning of every training everything hurt. But sooner or later she would love me to do that.I then put rings through her nipples and on her clit. I put. I was astonished to see that she is far more attractive in person than in her pictures. I got to thinking when I saw her that had not been with a man since her divorce. We drank, conversed, and ate for a couple hours and headed out. I received several indications that she is into me but I'm hesitant in making any moves since this is essentially a feeling each other out date. We gave each other a hug and she said she wanted to see me again. Our second date We saw a movie and ate dinner at a nice restaurant. I never tried kissing her or putting an arm around her all night because I didn't want to ruin the evening. At the end of the night as I put her in her cab she leaned in for a kiss that I wasn't expecting at all. 15 minutes later she called and said, " That she wanted to spend the night with me. We were both pretty buzzed after cocktails and she is coming on pretty strong. At one point she asked how big I was. Most guys LOVE to fucking lie about their dick size. I'm not one of.
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