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Tanya and I have discussed my love of anal sex, and she has agreed to try it with me, but that she is afraid. She has done it only once before and it was quite painful. I have explained to her that her other partner was an inconsiderate jerk, that there should never be any hurt whatsoever and if it should occur, that it was an indication to stop and proceed more slowly. Although at my other letters to her were pure fantasy, not cast in stone and may not happen, or will in a modified form. However, with exception of some foreplay, this will happen exactly as I will describe it.

I have heard her story before, and it really pisses me off. How many women, or men for that matter have had a first time experience of this type and had what to me is an important part of their sex lives totally ruined, when with a little thoughtful consideration, this could be a valuable adjunct to their sex lives. Now, to the letter.

We have spent a quiet day together, lounging at the pool, watching TV, reading, simply reveling in being with each other. Together we prepared our evening meal and now we are cuddled on the couch. We often enjoy watching porn movies and tonight I have selected one that is special. This one has a series of vignettes, all ending with anal fucking. I know of your fear and trepidation, but this is something I need to make our relationship complete. We watch as the performers go through all the normal porn actions, the obligatory blow job, the cunt licking, the vaginal penetration. But during the first scene, I notice a sharp ...

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stories in "anal sex"   |   all stories by "Great Bear"