Trained By A Proper Mistress

by Cissykay

   

Here I was. Sitting at a restaurant bar, waiting and anticipating this woman that I had met a few weeks ago through a personal ad on the internet. I had never had much success in connecting with dominant females on line. It seems that there are just too many men that have the same wants and desires. I read her ad and since she lived only about one hundred miles from me, I decided to see if I could pique her interest. Much to my delight, she responded. We began to chat on line, and I knew immediately, I had found the woman of my dreams.

Our age difference didn't seem to matter to her. None of the usual barriers that stand between a dominant woman and a submissive man were left standing. We talked for hours on line those first few days, and I found myself telling her things that I had kept inside for my entire life. She got me to open up in ways that I thought I would never do.

I told her that I knew I had a feminine side to my personality. This seemed to be a spark for her, as she said she was interested in finding a submissive to explore many things with. My desire to be feminized by a woman came out, and her desire to take total control of a man was very apparent by her writing. I have never had any desire to be with another man, since I am quite straight, and I was quite worried that this fact may preclude our ever being together because she is bisexual. She quickly assured me that she already had a life partner, but her partner was more of an onlooker than a dominant or submissive.

I had seen photos of this ravishing beauty, but as of yet, she didn't know what I looked like. Being quite average in just about every respect, I was afraid that she would take one look at me, and run away. Much to my delight, she sat next to me and ordered a drink. Her smile was very infectious, and it didn't take long to learn that this was not a woman to be played with.

"Did you follow my instructions?" "Yes Mistress Angela. I am wearing what you ordered." What she had ordered me to wear was a bra, panties, and pantyhose under my male clothing. I was terrified that someone would notice that I had a bra on under my shirt, so I made sure that I wore a sportcoat to eliminate any chance of the shoulder straps being seen. I had also made sure that all the hair was removed from my private area. She had told me she was undecided on whether or not to do it herself, or have me do it. She finally decided thet she would enjoy knowing that the itch caused by the hair removal would be driving me mad. I knew she had no way of knowing if Iwas really wearing the articles that she demanded without groping me at the bar, and I knew she was too much of a lady to do that. She would just have to take my word for it.

The conversation was fabulous. I knew we could talk comfortably, because we did every day on line since we met. I also knew she would be well spoken, because unlike many people one meets on the internet, she was very articulate in her writing. Everything was going along great. I was already looking forward to our next meeting. Although this was a Friday, our arrangement was for a couple of drinks, and if we really liked each other, we would make plans for a future date. I knew I was hooked, but I was getting nervous because although she was quite pleasant and receptive, she gave me no indication that she wanted to see me again.

I soon reached my three beer limit. I have a rule that I never have more than three drinks if I have to drive, and I had a long drive ahead of me. "Mistress Angela, you are everything that I thought you would be, and more. I do hope you found this evening enjoyable enough to want to see me again? At some point, I would love for you to have your way with me." Boy, was that a stupid thing to say. I had been so cool all evening, and now the words just dribbled out of my mouth, and hit the floor with a mighty crash. "I enjoyed myself also this evening, but I am disappointed that it is ending so early. I do understand that you have to find you way, and this is unfamiliar territory to you. But first, I want to make sure that you adhered to my orders exactly." With that she reached into her purse and handed me a plastic bag. "Please go into the restroom and remove your undies, and replace them with everything in the bag. You have five minutes, or I will be gone. You had better get to it honey. And bye the way, I also want you to put your male socks in the bag with what you remove."

I knew this woman was devious by our conversations, but I didn't expect her to actually call me on the underwear issue. It was lucky I was wearing what I had been ordered to. I dashed off to the restroom and opened the bag. Inside was a matching panty and bra set. I was amazed to see that the panties were crotchless. Both were black with lace trim. The bra that she gave me was quite a bit larger than the "B" cup I had on, and I knew that it would be more difficult to hide under my cotton turtleneck shirt. There was also a black garter belt, and a pair of very sheer, seamed black stockings. I hadn't had too much practice fastening nylon stockings to a garter belt, but with some obvious difficulty, I finally got them hooked. By this time, it had to be close to five minutes, so I had to hurry to get my street clothes back on and get back to Mistress Angela. I already knew that this was not a woman to fool with unless you really enjoyed being punished, which I didn't.

Finally, out of breath, I returned to the bar to find that Mistress Angela had moved to a seat at the end of the bar. It was more or less a horseshoe shaped bar, so we were seated in the corner. "Very good. I'm glad to see you know how to follow directions. It just might save you much discomfort in the future, although, I doubt it. Please order us another drink while I see what other surprises I have for my new sissy." I did as I was told. I could always sit in the car for a little while if I started to get any more tipsy. As I started to drink my beer, I knew it was starting to affect me, because the underwear I was wearing started to fell even silkier and sexier than usual. I just smiled at Mistress Angela. I hoped that she was going to let me wear what I was wearing for the rest of the evening. I wanted to wear it until I got home. "You see dear, if I have a few drinks, I open up to my desires more redily. I always have the desire to dominate and humiliate, but it becomes more open." I knew I was in trouble.

We talked for a a few more minutes, when Mistress surprised me again. "I want you to put your legs on my lap sissy, so I can feel the stockings. I love the feel of the nylon on a man." Since we were in the corner, I knew that I wouldn't be seen by anyone with the possible exception of the bartender, so I arranged my chair, and put my nylon clad legs on her lap. For several minutes she rubbed my smooth feeling legs. I was getting so hot that I was about to scream. She just smiled at my prediciment. "You like it when I tease you, don't you sissy?" "Yes Mistress, it's driving me crazy." "You'd like me to do something about your desires, wouldn't you?" "Yes Mistress. I would love some relief."

She then reached into her bag again and took out something I couldn't see. "Close your eyes sissy, and I'll see if I can find something to relax your desires. You can't open them again until I tell you too. " I closed my eyes as ordered, when I felt something being placed around my left ankle. I heard a click. The process was repeated on my right ankle. "Now you may open your eyes slut." I opened my eyes and saw that Mistress Angela had fastened a metal cuff on each ankle. These were different than any I had ever seen since they did not have a normal lock on them. They had the type that could only be opened with a key. Each cuff had a small metal ring on it.

"Now, that should ensure that you won't be removing your undies until I tell you to. You may try. But if you put a run in your new nylons, the penalty will be to wear the cuffs for thirty days." I could see that there was no possible way to remove these things without the key. "But Mistress." "Not another word sissy. I don't want to hear you whining now." There will be plenty of time for that later on." Later on? What did she mean by that? "Well, it's time for me to be on my way. It's been an extreme pleasure meeting you, and I'm sure we'll see much more of each other in the near future. I am going to very much enjoy turning you into a slut, and keeping you that way for as long as I choose." "You caan't leave these on me and just walk away." " First of all, I can do anyting I damn well please. Second, what part of not another word didn't you understand?" I just sat there in silence. I had no idea how I was going to get these ankle cuffs off.

Mistress Angela then handed me a piece of paper. Read this after I leave sissy, and not before." With that she stood up and walked out the door. The note was very explicit. I was to sit at the bar for one more hour, and then I could leave. I was to have at least two more drinks to loosen me up a little more. I was then told to drive to an address on the note, and if I was unable to do it comfortably, I was to take a taxi. I sat there for the better part of two hours, and ordered several more drinks while I pondered what to do next. I could go back home and attack the problem of the cuffs in the morning, but it was the weekend, and I wouldn't even know who to call. I had definately gotten in over my head with this woman. Somewhere in the back of my mind I was sure that our internet meeting was just two people that wanted to share fantacies, and nothing more. I now knew that Mistress Angela was indeed a true dominant. I just couldn't take the chance of going to the address and subject myself to any further problems.

Who was I kidding. My heart was racing, and I was more excited than I had ever been in my life. There wasn't any way I would not go to her, and we both knew it. I finally paid my bill, gave the bartender a generous tip, and asked if he knew where the street was that Mistress Angela wrote in the note. As it turned out, it was only a very short distance from the restaurant, so the question of a taxi was answered. I only had to drive a couple of blocks. When I arrived, I was greeted by Mistress Angela, who had changed from her very sexy leather skirt that she wore to meet me. She was now dressed in underwear very similar to what she had ordered me to wear at the restaurant. The main difference that I saw right off was that she could remove hers. I knew I could slide my stockings down my legs if I want to chance hooking them on something and putting a run in them. I also knew that it would get me in deep trouble with Mistress Angela.

"I see you made it here sissy. How resourceful of you." Yes Mistress, I asked directions from the bartender." "Well, don't just stand there, come in." I walked in and was nicely surprised to see that everything was very neat. This woman was not a slob by any means. "Take off your clothes sissy. I want to see how you look in my gift." I removed my outer clothes, and stood there wearing nothing but my balck lingerie and tose damn ankle cuffs. "Oooh sissy, you look could enough to torment in that outfit. Maybe I will do just that. I do have a few more gifts for you tonight though." She then directed me to the sofa and ordered me to sit. "Since my plans for right now do not include anything on your arms, I might as well give you these." She told me to hold my arms straight out, which I did. Mistress then locked an identical cuff to the ones on my ankles to each wrist. "There, now you have a matching set. What do you say?" "Thank you Mistress." "Your welcome my dear little slut. Let's see what other tricks I have in my den for you tonight."

She then reached to one of the boxes next to the sofa and revealed a lifelike pair of breastforms. They are a 38C she informed me. "They will fit your new bra perfectly." In another box was a pair of 5" stiletto heels with locking straps. Thet fit me to a tee. It was only then I remembered that she had asked me for all my sizes during one of our online conversations. "Tonight, we are just going to have a little fun at your expense. I hope you enjoy what I have planned. I know I will." I was now sitting in front of her wearing everything that she wanted me in. My clean shaven scrotum was in plain sight because of the crotchless panties I was forced to wear.

After I was ordered to model for her for several minutes. she decidied it was time for my next torment. "Follow me slave. I have something I wish to try on you." I was led into a room with an obvious feminine touch. It was difficult to walk in the new high heels since I hadn't had much practice. The most outstanding feature of the room was the four poster bed with the very stout rails. Mistress Angela then went into the dresser drawer and took out yet another smaller box. "I appologize sissy for being so unthoughtful. It isn't proper to give you bracelets for your wists and ankles, without giving you a pretty new necklace too. Where are my manners?" With that she produced a matching metal posture collar that had to be at least five inches high in the front. It secured the same way as the others, and could only be removed with a key. When she locked it around my neck, I could not bend my neck enough to see my feet.

"How does that feel sweety?" "It's much too restrictive Mistress. I can't move my head up or down, or side to side." "Well, I don't see why you would have to. Just a little while longer sissy, and I'll be done playing. You can last a little longer, can't you?" I was dying to tell her to remove these metal traps, but I did so want to make her happy, so I agreed to go along for a little while longer.

When Mistress Angela produced a metal spreader bar and locked it between the metal ankle cuffs, I was forced to stand at the side of the bed with my legs spread too far apart to even be considered comfortable. Mistress Angela then gave me a slight push backward. Between the spreader bar and the high heels, she knew I couldn't maintain my balance. I fell backward onto the bed. she then took hold of the spreader and spun me in the bed so I was now in the middle of the bed. I tried to get some leverage with my hands, but I was told to lay down and stop squirming. Mistress Angela then produced several lengths of chain and several locks. She locked a chain to each ankle cuff, and then wrapped each chain to the bottom of the footboard, and secured the locks. I was now effectively her prisoner. Not that I had much choice before she did this last procedure. I was ordered to lay flat, and she secured a chain to each wrist, and then locked them to the bottom of the headboard. By using the bottom of the posts on the bed, she totally immobilized me, I couldn't lift either arm or leg off the bed, and I was stretched too tightly to get comfortable.

Well, my little captive sissy, you look just good enough to eat, all bound up and quite helpless. It gives me the feeling of total power over you. You do want to give me total power over your life, don't you?" I was always a smart man, and I knew it would be smart to tell her what she wanted to hear now. "Yes Mistress, I do want to give you control over my life and body." "That's good sissy, because I do have total control of your body right now. I can do anything I like to you, and I don't believe you are in any position to stop me." She was right. "How ould my new little sissy like a little bright red lipstick to wear so you can look more like the slut that you are?" It was a rhetorical question since she had already produced the liner and was applying it very carefully. When she finished with the liner, she made up my lips with the wet look, bright red, whore lipstick. "This is non smudge sissy. It will stay on for hours."

"My last fun thing to do before this night is over is to see just a little tear in those pretty green eyes, so ou will know that I am your Mistress." She went to the bedside nightstand and came back with no less that six steel alligator clips with very sharp looking teeth. She slowly attached each one to my balls, while I spasmed with the pain of each torture. After what seemed like hours, she had all of them clipped on my ballsack.

"I don't want it ever said that I'm not a fair Mistress, so I am now going to offer you a choice. Would you like me to put a nice ball gag in your mouth to complete the look?" I immediately squealed a resounding "NO." "Not even for a little while." "Well then, I won't use a gag on you tonight. Besides, it wouldn't go with you steel collar, and cuffs. And most of all, I don't want to smear that wonderful lipstick. I'd rather kiss it. Mistress Angela then excused herself so she could go to the bathroom. It seemed as if she was gone for hours, when in reality, it was but about five minutes. Out of the corner of my eye, I could see that she was holding something. She then reached over to the nightstand table a produced a set of keys. "I bet you're happy to see these sissy." I was. It was already becoming quite uncomfortable for me, and the clips had me wincing.

"I know I've said it before this evening, but just one more thing to make your Mistress happy. Will you be a good submissive, and say yes?" She knew all to well I had no choice. I was in her control, and I wanted to be freed. "Yes Mistress Angela. I want to please you. What do you require?" "Just open your mouth nice and wide for me." I did as I was told, and Mistress Angela began to insert a jaw spreader in my mouth. I had seen them before in my dentist's office. They are used to force a patient's mouth to stay wide open while he works on your mouth. I also had seen them in several bondage sites for sale. She proceded to insert the spreader, and she adjusted the screw until my mouth was wide open. "There you go. You were right sissy. This is much better. I can see your painted lips, and the lipstick won't wear off. Well, it looks like I'm just about done with everything I wanted to try on you tonight. How do you feel?" All I could do was make a gurgling sound. You see, a mouth spreader has the same effect as a gag, in sofar as the person wearing it can't speak. I was trying to tell her that the clamps were pinching me, the chains were very, very restrictive, the collar was viscious, and the beer had made me need to pee.

As if Mistress read my mind, she held a hospital type urinal under me, and I was able to relieve myself somewhat. "Well sissy, that was fun. Do you want to play some more tonight?" I was in a panic. I managed to rock my head back and forth enough to show her that I had had enough playing. "Oh, you don't want to play anymore. O.K. sweety. Either do I. It's now time to get serious. As I watched her take all the keys and place them in her bra, she got off the bed and said, "just think about all the feminization you're going to have to endure tomorrow. Sleep tight lover." with that she turned off the light, and left me.

  

  

  

*********************************************
© 2003 by Cissykay. All Rights Reserved. These documents (including, without limitation, all articles, text, images, logos, and compilation design) may be printed for personal use only. No portion of these documents may be stored electronically, distributed electronically, or otherwise made available without the express written consent of StorySite and the copyright holder.