The pressure of work everyday to day took its toll on me. I ran a large production facility of a top name company. I was know for getting things done on time to meet deadlines. I would go home after putting ten and some times twelve hour days. I would relax in the privacy of my home which was located in a rural area with no close neighbors. One day I decided to take a trip to the casino and spend some money and relax some. After loosing a few hundred dollars I bumped into this chick spilling some of her drink on her hand and arm. Once I finished apologizing and wiping off the drink I looked up only to see this beautiful burnet bomb shell. She looked at me and told me it was alright and I asked if I could get her a replacement drink for spilling hers. She accepted and after a couple of hours talking and getting to know each other she invited me back to her place.
We talked for hours about my friends, where I worked and where I lived and her likes and dislikes and that she was finically secure. Before long it was two in the morning when I checked the time. I told her I had to get going and she asked what my hurry was? Today is Sunday she said, do you have something going on? I told her no and said I could stay longer if she liked. Well one thing led to another and I ended up in bed with her. We didn’t get out of bed until around ten that day. When I left that evening she asked if she would be seeing me again. “Now on a scale of 1 to 10 she was a 10 plus in my eyes”. I told her I would be over the next weekend, then got in my car and as I drove off could hardly wait to come back to her.
When the weekends came around I could hardly wait to get over to her place to spent the whole time with her. Then after about six months later when I was leaving to go back home she asked if I was into any kinky things. I told her that I had not done anything kinky that I could think of. She asked if I wanted to next weekend? Not thinking much of what she had just said I answered sure, as I planted a big kiss on her lips. When the weekend came I rushed over to her place with anticipation on what she had in mind. Once their we had some drinks and she asked if I had given any thought on what she had said before I left last time. I told her that I didn’t think much about it with work and all. She had something in mind for me and asked if I could be open minded? I told her that I was very open minded and would go along with any thing she had in mind. As she left the room I was told to wait for her. When she came back into the room she was wearing a dominatrix outfit. This surprised me as she walked into the room smacking her hand with a riding crop looking hot. I couldn’t take my eyes of her, she was stunning and erotic. She asked if I was ready for some real fun? I told her sure what ever you want. Then follow me she said as we went to the basement.
Entering the basement I saw a dungeon that had all the dominatrix items that you could think of. Every item had a place and was very neat in appearance. I was very concerned to what she was into and what was in store for me. She had never said any thing about this in the six months of seeing each other. Then she ordered me to strip naked as she smacked my ass with the riding crop. Once naked she told me to put the clothed in the bin as I would not be needing them this weekend. Standing naked with an erection she told me to go open the second drawer and take out everything in it and put it on the binding bed. I did as I was told and there was a bunch of women’s lingerie. Then she ordered me to put on the panties, garter belt with nylons and matching bra. I looked at her in disbelief, as I stood their she told me to put the lingerie on and smacked my ass again only harder with the crop. I didn’t hesitate after that, I put on everything as she instructed me to. I told her that I really felt uncomfortable dressed like I was. Feeling a little vulnerable she asked as she pointed out my stiff erection, then told me to stand in the middle of the room. She picked out a pare of three inch high heels and told me to put them on. They where a perfect fit which made me wonder what the chances of all these items fitting me so well.
Then came her instructions. First off you need to listen closely to what I am going to say and you will obey every thing your told to do. You will refer to me as Mistress. DO YOU UNDER STAND? Yes Mistress. You are only allowed to nod yes or no, and you will only speak when asked to do so is that understood? I nodded my head yes as she circled me smacking my ass with her crop as she walked behind me. I let out a yelp and she hissed at me “be quiet you worthless little bitch”! I was at a loss for words, this was nothing that I ever thought she would be like. She told me to stand straight and eyes straight forward. When she stopped in front of me, she reached out and cupped my balls as she looked into my eyes saying. These are not yours any more they are mine to do with as I see fit, DO YOU UNDERSTAND? Nodding my head yes and realizing my cock was as hard as ever as she ran her finger nails up and down my cock shaft.
It was almost like I was in a trance as she walked over and took something out of the dresser drawer. Next thing I knew she was snapping pictures of me standing their in lingerie. Then she pulled down the panties and snapped some of me with my erection. Pulling the panties back up and setting the camera down she looked into my eyes and just inches from my face as she said, your my little bitch now. If you don’t do what I say your pictures will be posted and mailed out to every one you know and to the company you work for. My heart sank and a sudden thought of what I had gotten myself into rushed over me. She continued to tell me that she was going to brake me and how I had to obey her every command if I did not want to suffer any consequences. Then she picked up an anal plug as she held it in front of me saying. You will learn faster once this is in you and then I will tell you more. I was instructed to bend over a table face down as she cuffed my wrists. Then spread my legs wide and fasting a spreader bar between them. Lubing my hole up and the plug she eased it into me as I squealed in pain. Stopping only to put a gag into my mouth she continued until it was in place.
I was told as she pulled on my cock milking it which felt sooo good that her hobby was running her dominatrix dungeon and she had many male customers that paid her well for her services. She informed me that I was going to be her personal assistant when she had a, helping her as required. I will be dressed mostly in lingerie only. I climaxed as she said that and she pointed out that by climaxing on those words only confirmed my excitement and acknowledged my new position beside her. She stated how happy she was that I had accepted the my new roll. I thought about the arrangement and decided since I was single and had no one in my life I would go along with it. I ended up selling my place and moving in with her as she took over my life. I became accustom to her verbal humiliation and ordering me around. From then on I always wore lingerie around the house. Over the next few months I quit my job which I was only too happy to do. I was trained in anal intercourse, dildo training. I was taught the art of applying makeup. By this time she had me trained and doing what she ordered me to do. I was at her mercy 24/7 and had become accustomed to being her sissy with my cock in chastity and having my ass plugged most of the time. While assisting her in the dungeon when she had a client visiting she would remove my chastity cage so she could see my erection as we worked with him. She would point my erection out to the client saying how sexually aroused I was over seeing the client naked. Some times she had the client suck my cock to completion. When no clients where visiting she would putting me through different paces of domination. Some times I was dressed as a maid and cleaned her house and did her laundry.
She pointed out how she had taken my close sizes and shoe size when I was sleeping during my first visits. I figured that she had this all planned from the start and I fell for it. I was only allowed to have sexual release by masturbating as she watched and that was seldom. I really became used to the situation and when I am allowed to ejaculate she will catch it in a wine glass and I have to drink it when I am done. I am not allowed to have intercourse with her but I do have to stimulate her with my tong almost nightly witch can take hours until she has an orgasm. Basically I am her house maid and her toy to play with. She tells me that I transformed nicely and was very easy to manipulate into my new status in life. I have been given a new name which is Jenney. I have broken all contacts with friends and only live to serve her needs.
“SM” Sissy Maker