She is so gentle and understanding that I thought she would be the best person to try exploring anal play with, and she wouldn’t be upset if I didn’t want to continue. We usually get together every couple of weeks anyway, so she started slowly introducing me to anal play. After a couple session of her just using her fingers on the outside, I asked if we could go further next time. Our next few sessions she used her tongue and started probing inside. I loved it and on our fourth session of that, I finally asked her to finger my ass. I have been trying to work up the courage to take the next step, and when I heard we would be alone tonight I knew it was my chance.”She looked back up into my eyes and asked, “Master, will you please take my anal virginity tonight? I know it will be painful at first, but if my reaction the Katherine’s fingers are any indication then I will love it. I’m just sorry I waited so long, especially after what you did for me tonight. I feel like I have been. She has grown up in the four years since we first met. Then she was a skinny twelve year old with braces, now a beautiful young adult. Four years ago I was homeless, sleeping on park benches and begging for handouts. Unless you have been homeless yourself you have no idea how demoralizing it is. Dirty and hungry all the time, people either ignore you or are openly hostile. You become a non-entity, at the time when you are most in need of a friend you are the most alone. She was one of the few people who had shown me kindness during that awful year I lived on the streets, a twelve year old girl had shown more compassion and had more empathy for a disheveled, grimy homeless dude than almost anyone else. And for that I love her. She would speak to me kindly and share her lunch with me, I know her parents disproved but she did it anyway. I have red hair, did you know there was such a thing as kick a ginger day? When the other kids were cruel to me she would defend me. So now that I have.
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