I’m going to teach you how to be playful and seductive with your skirt–teach you how to be a sexy sissy girl.

    “Skirts are very different from wearing pants,” I explain.  “You are more exposed and vulnerable in a skirt.  If you trip or fall down, your skirt could come up and show your panties. That would be very embarrassing.  Of someone could come up to you and pull up your skirt and feel your bottom.”  “Really?,” Monika asks, eyes wide with fear.   “Yes, someone could do that, but mostly I’m going to teach you how to be playful and seductive with your skirt–teach you how to be a sexy sissy girl. Doesn’t that sound like fun?”  “Yes!” she agrees, relieved at the idea of choosing to be sexy, rather than being abused by someone else.  
    Monika excitedly starts playing, swishing her skirts, twirling around, sticking her butt out and pulling up her skirt and petticoat, showing her ruffled panties.  I egg her on, fondling her ass, when she shows it to me, playfully pulling her panties down in back and spanking her ripe little sissy butt cheeks.  She giggles delightedly, her cheeks flushed . It warms my heart to see my new sissy girl having so much fun with her femininity.

The first thing that comes to mind is the “naughtiness factor.”  It is such a forbidden thing for a boy or a man to wear women’s clothing.  A man who chooses to dress in women’s clothing is violating a strong social/cultural prohibition.  No such prohibition exists for women choosing to dress in boy’s or men’s clothing.  Yes, there are those “drag kings,” women who dress up to “pass” as men, often for entertainment purposes, or to compete in contests.  and some are quite convincing, and I find this hot, as well.  But this kind of “play” that women may do is much more acceptable, even admirable in the culture.      Another social/entertainment outlet for male cross-dressing is in the realm of “drag shows” or “dressing in drag.”  These are activities that have evolved mostly in the gay male community with cross-over and overlap with the transexual communities–particularly MTF transexuals.  For the male-identified gay man, dressing in drag is seen as a fun way to “camp it up” and have a good time, perhaps exploring femininity in a form that is accepted in gay male culture. These men consider themselves male, and for the most part the drag is a social/public event, not a private, secret practice.

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I can feel her hard cock as she moves her body side to side.  She begins to breathe faster, holding me tighter, and pushes a little harder against me.  I realize that I am perhaps moving a little too fast

    “Touching can be a two-way experience. I want you to touch me a little. I will guide you,” I say as I stand in front of Monika, my back to her.  “Touch my satin blouse. Feel the delicious texture.”  She reaches up tentatively, touching my shoulders and back.  “You can touch my breasts, lightly,” I add, guiding her timid hands.  “Rub your crotch against me,” I add, as I push my ass against her. She puts her arms around my waist.  I can feel her hard cock as she moves her body side to side.  She begins to breathe faster, holding me tighter, and pushes a little harder against me.  I realize that I am perhaps moving a little too fast.  She isn’t really ready for this yet, although her cock has other ideas. I have to admit that I am getting turned on and a bit carried away.  I need to restrain myself and not take advantage of my young sissy student.     I stop moving and turn to face Monika.  “Have you had any sexual experience with another person,” I ask gently.  She shakes her head. “Well, you’re in good hands. I will guide you when you are ready.”