For this story I will call her Jill. We have gone out on a few dates, and on my last date, Jill said she wanted our relationship to become more serious. I agreed with her, because she has many of the same opinions and values that I have. As far as our sex life goes, we have cuddled and kissed a lot, felt each other through our clothes, but haven’t gone any further than that. Jill is about three years older than I am, and is also as tall as me. So when she wears her high heel shoes on dates, I actually have to look up at her. So I was surprised at the end of our last date when she said, “When you show up at my house for our next date, I want you to have your pubic hair shaved. If we are going to get more intimate, I like my men well shaven down there.” I have wanted to get more intimate with Jill since our first date and I want to please her, so I said, “If that is what you want, I guess I can shave down there for you.” Then I was surprised when she added, “Be sure and do a good job,. I slowly got down on my arms and knees and got into the doggy position. He began to put lube on my asshole and slowly work it in with his fingers. It hurt at first but I had such a hard throbbing cock and the idea that my dad was about to fuck me had me near ecstasy. He slowly worked 2 fingers into my tight virgin asshole. That’s when I turned around and shoved his dick back into my mouth and spit on his dick and told him to stick his fat cock in my asshole. He looked at me and smiled, and flipped me over on my back. He then slowly began to stick the head in my asshole, and I started to whimper. The pain of his dick entering my asshole was unbearable. He asked me if he should use a condom a few seconds later and I looked at him and told him, hell no. I wanted to be raw dogged by my dad and I wanted to feel every inch of his dick. He still had the head of his dick in my ass and even though it was painful I had never been turned on more. He slowly inched in and out with his dick till.
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