She asked if I wanted to sleep over in the literal sense of the word. That was an amazing confidence builder.
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He then proceeds to vomit on her. He said that he had a friend at school that allowed him to slide his cock into his anus using a lube, and it was a great sensation and that I should try it some time. We were going at it, pretty hardcore. She said wait, I came, pulled out, felt embarrassed, and left her hotel room. We chat briefly and she leaves. I told her I could see her nipple. The third time was with my current wife. She asked if I wanted to sleep over in the literal sense of the word. Let us know in the comments. On the second night I was there, she came into my room to say goodnight to me.
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I high-fived her. It was so embarrassing she denied it ever happening for three years.