The Sissy who Wears Panties and His First Experience with a Femdom Mistress

It all started with a post on craigslist. The headline read “Fat Sissy wearing Panties Looking” it was sort of a generic headline and I was not expecting to get any replies but boy was I surprised. I got tons of spam messages but there was one in the middle that stood out, it was not asking me to contact them through some other email address or telling me they were from out of town. This one was simple, the reply simply said,

“I am 33, we live in the same town and you will do as I say. No questions, no second guessing, I am in charge.”

I looked at the message for a few moments and wondered if this was actually for real. I decided to reply with “Yes Mistress, how may I serve you?”

My First Response

Within minutes I was sent instructions on what color bra and panties I was supposed to wear as well as what color pants and shirt I was to wear. I was instructed to meet her in two hours at a local restaurant. I showered and made sure I was smooth and hurried to the designated restaurant.

When I arrived I waited outside as instructed and finally the hostess walked outside and asked me if I was waiting for “Alison”. I was not sure how to answer; I was never given a name and stared blankly as I thought of how to answer.

“She told you to wear red” the hostess said.

My face was flushed when she said this to me, that was the color of my bra and panties and I stuttered as I said yes.

Red Bra & Panties

I was led to a table where a short woman with long auburn hair sat sipping on a glass of wine. The hostess pulled out my chair and I sat down.

“Show me,” Alison said. “ Let me see your bra”

I hesitated but my hand slowly unbuttoned three middle buttons and I quickly flashed my bra for her to see.

“Good, at least you can listen. I already ordered for us. Since this our first meeting I forgot to ask if you had any food allergies. If so please let me know and I will have them take it away and you can watch me eat tonight.”

“No Ma’am, no allergies” I said as I buttoned my shirt back.

My First Dinner in Panties

“Good, If this works out, I will always be ordering when we go out. You will not speak unless spoken to. You will also arrive first from now on, I expect you waiting by the table to pull my chair out for me. Do you understand?”

“Yes Ma’am.” Was all I said.

We spoke for a while, well she did most of the talking and I listened. Occasionally she would ask me to elaborate on certain things. She was interested in my limits and expectations. I explained how I am very submissive and obedient and look at females as the dominant gender. My goal, dream and desire in life is to do what I can to please women and show my true submissive side.

Submissive & Obedient

She nodded with what I was hoping to be approval at my answer. When the food arrived she told the waiter that I was not hungry and would like my meal to go. I watched her as she ate and enjoyed her meal in front of me.

“Sometimes you will be allowed to eat when I eat, but I prefer you be ready for me when I need it, so usually you will eat when I am relaxing or do not have anything for you to do. “

“Yes Ma’am.” I nodded as I answered.

When the bill arrived I paid and pulled out her chair so she can stand up. I carried her items to her car. She opened her door and looked at me, I was nervous and kept my head down.

My Submissive Orders

“I think you will be obedient enough for me. Give me your phone number and I will contact you again. I will also be sending you things to do, what to wear, when to go to bed and what to eat. I also expect replies within 10 minutes, do you understand?”

“Yes Ma’am” I said again as I gave her my phone number.

She got into her car and the door stayed open, I hesitated for a brief moment then quickly but gently closed her door for her. She did not even look at me as she drove off. That night I got a text; it was short but to the point.

“Tomorrow, pink bra and panties, white shirt”

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