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I was truly learning humiliation. Elaine smiled wickedly down at me as she returned to the drawer; I noticed at this point that the damp patch at the front of her panties was now very prominent. She took a blonde wig and large stilettos from the draw, and two other objects. After placing the wig on the hanger and the shoes beneath it, the women all smiled smugly at each other as Elaine made ready to display the two objects with a very victorious look on her face. With deliberation she placed the two objects on a side table. The first was what looked like a transparent penis in flaccid mode, with a tiny padlock. I gulped visibly and much to the delight of the women as it dawned on me that this was a chastity device. Elaine undid the little padlock with her delicate spikily nailed fingers, as the ladies enjoyed my apparent look of discomfort at the idea.“You’ll be milked nicely this evening and tonight; you will beg me to fit this before midnight, so you enjoy tonight’s. ” And then, with infinite gentleness, he raised his hand higher. This time the knuckle of his thumb nestled in the pleasure center between my thighs. He added some light pressure, opening me up even further. “Yes, I can see the problem now. My thumb was in the way of the ruler and blocked my view. Shall I move it out of the way?” “Yes, yes.” He straightened his thumb and positioned the tip at my dripping entrance. Then slowly, gently, and in one continuous movement he pushed into me. The pleasure was excruciating. Stroking his thumb in and out, he picked up an increasing rhythm and said “Belinda, you realise that Miss Strachan is still in the outer office.” “Yes, Sir,” I was starting to build up to a climax, which I knew had to be silent. “I want you to do something for me.” “Anything,” I whispered. “There are a great many things that you can learn about becoming a woman that even this school does not teach in the syllabus. Even so, I am very well versed and would be pleased to tutor.
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