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Chapter 3 by ymous42 ymous42

Do you jerk off?

No, go get dressed

You think better of it. From what you've seen so far this school has never skimped anything where discipline is concerned. You head back to your bed, covering yourself with a towel. Boys at Mistress Alessandra's are required to wear a small amount of makeup, though you've notice the older (and more submissive) boys tend to wear much more. You apply a little bit of lip gloss, blush and mascara. You comb your hair, you were instructed to let it grow out. Most boy's hair is a couple inches long or as people sometimes say, long enough to grab.

As with pajamas, you are always given something to wear. Class uniforms are short(ish) heels, knee high socks, a plaid skirt (which goes less than halfway down your thigh), a pink g-string, and a tight light pink polo. Your cock is relatively small, but even for you the outfit is awkward. A bell rings and you and the rest of the boys in your dorm hall hurry to the end of their beds. You can see Matron Andrews is checking your row this morning. All of the matrons are slightly older and for the most part very mean. Matron Andrews is no exception. She is wearing something akin to a nurse, which highlights her wide hips and hugs her small breasts tightly. She reaches your bed and you try to keep you posture as straight as possible, hands outstretched for her to examine. She looks the front of you over, noticing your makeup with a look of mild distaste "Turn." You turn, putting your hands on the bed, this was very jarring the first time it happened. Matron Andrews sticks her finger in your mouth, getting it wet. Then with the other hand she flips up your skirt and pulls the g-string to the side. A cold finger slides into your ass, the first time you cried out and received a spanking. She slides it out of you and you exhale softly. She then pull your socks down to make sure your legs are smooth and hairless. It is the students job to go to the school salon for waxing. She stands up leaving you disheveled your hands still on the bed.

Is she satisfied with your cleanliness?

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