At first the newness and the strangeness of being asked (and thencommanded) to become more and more feminine had only stirred me assomeone who was sharing a sexual (albeit somewhat unorthodox) game withsomeone I loved. But as the months passed, I found myself intrigued as towhat new adventure in girlishness Annie could concoct for me. I foundmyself even looking forward to those times when Annie would deliberatelycause me humiliation and shame. Humiliation and shame experienced as aman, the same situations growing more and more thrilling to me as apseudo-woman.So Annie's answer was very important to me."Jim, do you remember in 'Tootsie' how Dustin Hoffman became obsessivewith portraying himself as the best and prettiest woman he could be? Ifound that part of the movie fascinating. But I also found that part ofthe movie to be somewhat unfulfilling to me, personally. As I watchedHoffman become the woman HE wanted to be, I realized quite quickly thatwhat was missing for me was a woman. " I hand it toyou, and you're not sure what to make of the slightly lubricatedcardboard tube with the cotton insert. "Pull down your panties,Sissy, and I'll help you put in your first tampon." You obey,and bend over, and I insert the tampon slowly into your virginass. You are all tight at the unaccustomed invasion, but I waitfor you to relax a bit until it slides in easily. "How does yourtampon feel, Sissy?" I ask. I smile at your answer, "Its so big,Mistress!" Before this weekend is over, you'll reflect back onhow tiny it really is, compared to what will be stretching yourlittle rosebud! "Don't worry, Sissy, you'll get used to it soon,(and a lot more, I think to myself) - besides, women have to putup with it every month for years and years."I walk you toward the bed, then pretend to notice the mess theroom is in for the first time. "Sissy," I say in a loud voicethat startles you, "your room is disgraceful - more like apigsty than a young lady's room. I'll bring you in some.
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