My New Mistress by Missy (1999)

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My New Mistress by Missy (1999)

We met at work. She was so confident and “take charge”. I have always been somewhat shy and uncomfortable around people. She was attracted to that I think and began to court me. I just fell into the more submissive role, which only made sense, since I was a closet transvestite. Of course she didn’t know that at the time. It really wasn’t long before we began to date. I felt so comfortable with her and I wanted so badly to have some one that I could share my secret life with. Some one that would understand me and accept me for what I was. I began to drop hints and say little things that might be interpreted as to my real nature. She seemed to understand my feminine nature and it encouraged me to keep revealing my secret self and desires. One day it all finally came out. I told her about how I was a submissive transvestite and had been dressing up since I was very little. How I longed for a woman that would understand. She comforted me with kind words of understanding and empathy for how badly I must feel, secretly pretending to be the man I wasn’t. Sitting on the couch next to her I was so overcome with relief that she had accepted me that I slid onto the floor and just hugged her stocking clad legs. She stroked and patted my head while asking me about how I began cross dressing and all the turmoil I had gone through as a child and a teen.

How I had dressed in my Mother’s and sister’s clothes and had even stolen female clothing to wear in secret. How I had purged many times, trying to quit dressing up but always coming back to it again and again. I spent the rest of the day happily sitting at her feet explaining my crossdressing to her. She asked if I had any women’s clothes now. I explained that I didn’t as I was living with a roommate and didn’t want him to find out by accident. “We’ll have to change that, won’t we.” she stated with a smile.

Part 2

We spent more time getting to know each other and to feel out what our roles were to be. We also spent time exploring fantasies and desires. The idea of a submissive transvestite that wanted to serve her appealed to her. The idea of a woman to dominate me and control my life totally was a dream come true. I bought her loads books and magazines and stories about TV's, Female Domination, sissy maids, sissy babies and the like in an effort to bring her up to speed on the subject. Also it was a way for me to show her the things that I liked without actuallly having to admit to it. I was somewhat embarrassed to tell her about all the things I found exciting. It seems humiliating to like these things let alone confess about it.

She talked to me about the stories. If I really wanted to be like the people in them.To be her sissy slave, her french maid, her little girl, etc. I confessed that I did. "Before we start all this, you are going to have to swear your obediance to me." she said. "A real show of your subserviance to me. What should we have you do...?" I watched her face poised in thought; my heart soared with delight. She's going to let me be her TV slave!! my brain shouted. I was afraid she would change her mind and stop seeing me. I shouldn't have worried about that. "I think that you should go to a Tatoo Parlor and get something to prove your sincerity." she announced while looking at me sternly. "You...you want me to get a tattoo?" I asked. "Yes! I want you to get a tattoo to prove that you are sincere in your desire to be my little sissy bitch! Or were you just blowing smoke?" "I...I...I..." "Look! if you don't want to do it then you can just leave and stop wasting my time." By the look on her face I could tell that she meant every word. She told me what she wanted me to get and not to come back or call her until I was ready to show the tattoo to her. It took me a week and a half to work up the nerve to find the right place and get the tattoo done. It was most embarrassing. The day after getting the tattoo I was in her living room with my pants and shorts down around my knees bent over so that she could see it. On my right buttock was a greenvine with red roses and the words: PROPERTY OF MISTRESS KATHRYN. "That's very nice." she said admiring the roses circling the words. "Now that I see you are sincere we can begin. Of course the first thing is that you need to be punished for taking so long to carry out an order. I expect you to perform much faster than that from now on. Why don't you stay in that position. Perhaps you should grab your ankles. Now don't move or go anywhere, i'll be right back."

~~~~~~~~~~~~~~~

Part 3

 I had fantasized about getting spanked many times before but I found out it wasn't nearly as much fun as I thought it was going to be. She beat me accross my buttocks and a few times on the back of the thighs with my own belt. "What do you have to say?" she questioned. " Trying to think fast I said, "I'm sorry I didn't listen faster...?" CRACK came the belt again. "That's not much of an answer is it? I know it embarrasses you to talk about these things out loud in a clear voice and that's precisely why I want you to answer any of my questions in a loud clear voice. Now answer me! What do you have to say?" "I'm sorry Mistress. I should have listened and got the tattoo right away." CRACK again. "That's slightly better, but... I expect you to give full and complete answers all the time from now on. Liike a proper slave." "Yes Ma'am. I will answer you properly from now on." CRACK again on my thighs. "Don't you have something to say about the spanking?" "Ummm....it hurt." I said lamely.

She sighed tiredely before giving me two more. "I am taking the time to train you to be a good little slave. Do you appreciate the effort I am making?" "Yes Ma'am I do appreciate it." Two more came and I was about ready to cry. It was really stinging across my thighs. "Then don't you think you should thank me!!" I hurriedly spit out the proper response. "Yes Ma'am, thank you so much for taking the time to help train me. I'm sorry I didn't obey you better. Please don't spank me anymore. I'll be good." I think I may have even whined a bit at the end. Crack! "Don't you tell me when to stop you little s**t. I'll beat your ass all day long if I want to!! Crack. "Yes Ma'am! I'm sorry ma'am!" "Stand up straight." she instructed. She walked around me while I stood there, pants at my knees. Stopping in front of me she began to touch and rub my flaccid pen-is. "What's the matter? Didn't you like your spanking?"

"No Ma'am, not really." Her light touch turned into a tight twisting grip. "No ma'am what...?" "Oooouuuccch! No ma'am I didn't like my spanking." She relaxed her tight grip. "You don't learn too fast. Or perhaps your not being truthful...it doesn't matter, either way I can see we're going to be having quite a few punishment sessions." she informed me while gently stroking me to excitment. "Look at you standing there in big boys underwear. Are you a big boy?" My pen-is went straight up and my head went down as I answered shyly, "No Ma'am, i'm not a big boy." "No...of course your not. Only real men wear those. What should you be wearing?" "Panties" I whispered under my breath. "What did you say? Answer me properly or you can have some more belt." "I should be wearing panties Mistress." I said with a little voice.

"Panties!? Do you mean you want to wear panties like a girl?" "Yes ma'am, panties like a girl." "Well then...don't you think you ask nicely? You don't have much in the way of manners do you? I can see we are going to have to do alot of work on you. Now ask nicely." "Yes ma'am. May I please wear panties like a girl instead of big man underwear?" She went on to make me beg to be allowed to wear panties before having me remove my boxers and throw them in the trash. "Yes I will allow you to wear panties. You should only wear panties from now on. In fact I think we'll go to the store and get you some right now."

Part 4

I was allowed to put my pants back on and fix myself up a bit before going to the store with her. We went to a Kmart across town and began to browse around the women's section. I think that men feel like they are being watched by everyone when they are in the ladies deptartment. As if looking at anything for too long would let people know that you are too interested and wanting it for yourself. And heaven forbid that you start touching things or holding them up. I felt very self concious. Secretly wanting all the pretty things for myself yet some how feeling that people knew we were shopping for me. She teased a liitle bit about wearing skirts when no one was around but we didn't linger too long in the clothing section. We ended up in the lingerie department and began looking at panties. There were only one or two other women there but I felt sooo uncomfortable yet excited.

        "Well...what shall we get for you." "shhhh" I whispered, embarrassed. Quickly I checked around to see if anyone had heard her comments but no one was in ear shot. She smiled at my discomfort. "Something sexy? she said, holding up a blue lace thong. Perhaps something more girlish? this time holding up cotton briefs with a pink flower pattern on them. My mouth went dry at the thought of having those panties just for me. Don't you like them? I just nodded my head. Now I thought we understood each other. she said in a disappointed voice. When I ask you something your to answer better than that." In a quiet voice while furtively checking to make sure no one overheard, "I'm sorry Mistress. I like the those panties alot."

She handed them to me and kept looking. I tried to hide them and act like nothing was wrong while closely following her every step. "Oh!! that's it. That's exactly what you should wear." I cringed at the words but followed her over to the next rack. "All the time people tell us "bigger" girls that we should wear girdles and control tops. You want to wear clothes like a girl? Now you can see what it's really like." She picked up a pair of white control panty briefs. "Let's see..." she said looking at the size tag. "Your about a medium or size 5 according to this. My head was going around on a swivel to make sure no one was close. Another shopper was fairly close. She looked at me and although I don't think she heard anything I am sure that my guilty looks must have made her suspect something. I just couldn't get myself to calm down.

                "I think a size small will be better. You can start dieting as part of your training. Watching you have to diet just to fit into your girdle comfortably should be amusing." With that statement she began to look for smalls for me. What could I say? I was rock hard at the thought of "having" to wear tight panties for her.