First meeting of a sissy with her Mistress

"Strip. Get off all those ugly man clothes. Now."

I looked around, saw the bathroom and started toward it and heard her stomp her feet. I looked back and saw her grimly shaking her head and pointing to the floor near her left foot.

I stood in the designated spot and the look on her face was grimmer yet. She moved her hand slightly, indicating DOWN. I kneeled. The smile on her face lit up my core and I knew that serving this woman would not be easy, but that it would certainly have its rewards – that smile in itself was enough reward to keep me going for days.

I took off my shirt and she frowned. I looked down and again realized how much I hated this body. I'm not a bear as far as hair goes, but there's more there than any woman outside a circus. I'd avoided looking at my chest for years, especially because I knew that it COULD be shaved. But shaving ... well, the questions from the woman who bore our children would be something that I simply couldn't answer. I'd shaved a bit in high school, as a swimmer it didn't cause any comment whatsoever, but there wouldn't be that excuse now.

My head hung as I continued stripping for her. I saw a tiny glimpse of a smile as I folded my clothes neatly. I stuffed my underwear under the folded trousers and saw her frown again. Sheepishly, I pulled them from underneath and folded them, too. Probably the first time they'd been folded since coming from the package.

I knelt before her, pressing my head to the floor and waited for her to acknowledge my compliance.

"Look at me. The hair. Chest. Legs. Back. Why?"

I explained my fears and she nodded, showing neither pleasure nor displeasure. "That may change. For now it is ... acceptable. Tell me, little one, what you wish out of our time together. Remember – what you tell me will not compel me to make sure it happens. I'm looking for your input, but all decisions ... are mine. You, indeed, are MINE. Your thoughts are no more than thoughts in my own mind, to accept or discard, to act or not as I wish."

"Mistress, I wish to be your sissy. I want to learn how to please you, I want to learn how to make myself worthy of being called YOUR sissy. I hope that I can learn enough from you to be pleasing to your friends if they come to call, that I not be an embarrassment to you. I want to serve; I NEED to submit."

I put my head down again, looking at her feet and hoped that she would accept my answer.


I stood, turning slightly away from a sense of modesty.

"NO. Face me squarely." As I turned I saw the crop in her hand. "That's not exactly what I meant by my question, sissy. Usually sissies start telling me about their fantasies as if I cared about pleasing them, as if my role was serving THEM. I'm pleased by your response, but I also need to know what ... inducements ... I might offer you if you especially please me in the future."

The crop flicked out between my legs and tickled my scrotum. "What is that?"

"What? I responded.

The crop flicked up and the pain in my balls was intense, but sweet. In very clear, clipped words, she repeated. "What. Is. That. The thing. I. hit."

"It's my scrotum, Mistress, my balls."

Flick. Thwack. "NO. It's your labia, your lips, slut. It's yours but it's MINE, too. Remember that. What is yours is MINE." The crop flicked up, catching the tip of my cock and she repeated "What is that?"

"Ah, my clit, Mistress?"

The hint of a smile made me glow and the attention she was giving me made me begin to respond physically as well. The crop flicked ... and flicked again. "Stop that. Focus on my questions."

I focused, deflating a little. Only a little.

"Now. You will listen to my questions carefully. I want you to close your eyes and mentally picture what I am asking. For example, Can you imagine yourself bent over the couch, maybe my lap, being spanked, sissy?"

I responded physically again at the mental picture I was building and I began to say "Yes ..." when the crop flicked down on my cock, harder than before. I shrank at the pain but only temporarily. I rose to half mast again almost as quickly as the crop had flicked down. "Don't say a word. Your body answered that question. Your body will answer every question, and your mouth will stay shut, slut."

"Are your nipples sensitive, slut?" My body answered, and again the crop flicked, with the same sequence of events. Up. Flick. Down then up halfway.

Her questions seemed endless and my answers were probably truer than any I'd ever given in any interview in my life. Clothespins. Anal sensitivity. Humiliating situations. Maid service. Using a vibrator on a woman. Using one on a man. A man using a vibrator on me. Teasing. Orgasm denial. And so much more.

My cock was on fire from every "yes" answer it had given. Yet there was a greater inner glow as I realized that, naked and vulnerable as I was, unable to hide my reaction to her questions, I was also sharing thoughts and desires ... needs .. with her that I'd never given myself the freedom to share before in my life.

"I'll have more questions next..." Flick ... as my body responded once again to the prospect of further secret sharing ... "week. Maybe every week. We'll see."

"We need to work on your wardrobe, but first things first. Today's lesson is going to center on your deportment. You need to learn how to walk, sit, and bend as a woman. Before you are granted the permission to wear the clothes of a woman, you need to know how to move like one. We're also going to go over my expectations of you. Maybe ... just maybe ... I'll use a tiny bit of your responses as the base for rewarding you. Only, of course, if you are worthy of reward based on this lesson."

(next ... the lesson ...)
17701 days ago, 4082 reads
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