Andy's Training

by Cissykay

 

Chapter 6

 

When we were through eating, Aunty Betty and Cissy sat back and each lit a cigarette. "Well Andrea, are you as happy as we are that your secret is now out in the open? To be honest with you, we've known about it for quite some time. We were just waiting for the right opportunity to show you. I'm really quite surprised that you never figured out that since I am a professional photographer, I would have several video cameras in my studio. In fact, I have them set up in every room in the house. Everything you have done since you moved in is on tape. I've taken the liberty of having my attorney draw up some papers for you to sign. Basically the first gives me the right to edit and use all the film I have taken to date. The next one gives me power of attorney to act on Andy's behalf on all financial matters. This includes, but is not limited to, dispersing the sizable fortune you will soon have on your twenty first birthday. Now you don't have to sign, and we can just stop now. In that case, you'll be forced to leave as soon as the police get here to arrest you for theft of all the lingerie I can document is missing, and that I have the film of you trying on." "But Aunt Betty, I've never stolen anything from your studio." "I know that, but try to convince the police of that when I show them an edited tape. Not to mention the fact that they will find you dressed as you are now. I just wonder how much fun you'll have when you are put in a cell dressed like this with other criminals." I knew I had no choice. I signed the papers and handed them to Betty.

"Very good Andrea. Now I want to set the scene for you for tonight. As soon as we get to the studio, Cissy will release you from your bondage. Please, don't get any ideas because it will only be temporary. You will spend the next six months in complete bondage. This will be your training. When the time is through, you will want nothing more than to spend the rest of your life dressed as a woman. You will become the willing bondage slut and maid to the woman that you marry. Until then, you will only have orgasm when I permit it. We will save the sperm for use as I see fit later. Although Cissy is the same age as you, she is now and always will be your superior. You will address her as you do me. You will be punished when you screw up. You will be punished when you don't screw up. Hell, you're going to be punished constantly. I digress here, Cissy will take you to the studio now, and we will start our first pictorial of my new bondage model." Cissy then gave a yank on my chain, and I was off to the studio. When we arrived, Cissy reinforced what would happen if I tried to escape. She removed my bonds and for the first time in a day, I was able to move freely. The first thing I noticed as soon as we walked in was that there were some things in the studio that were not there before. There were two racks filled with sexy lingerie and women's leatherwear. There was a new chair placed right in the middle of the two racks, and a long wooden box under the rack on the right. I had no idea what that contained. " If you be a good girl this evening, I have a surprise for you tonight. I'm going to let you make me come for hours and hours. You'd like that, wouldn't you Andrea?" I wanted to tell her what was on my mind, but I knew I would regret it later. "Well, would you like that sissy?" "Yes Mistress Cissy, I'd love to pleasure you for as long as you'd like." "I thought that would make you happy, you little dear."

When Mistress Betty entered the studio, she immediately adjusted the lighting, and placed the cameras for maximum effect. "This is a very important shoot for me Andrea. I want you to do everything exactly as I tell you to. Do you understand?" "Yes Mistress Betty, I'll try to be the best model you've ever photographed." "How sweet Andrea. If you keep up with that attitude, you may enjoy your training. If not, then it will be the worst six months of your life." She then brushed my hair for me. It looked wonderful when she was through. "Okay Andrea, just sit there until I am ready." She made a few more adjustments to the cameras, and all was ready. "I've turned off the microphones for the filming tonight, so I will be giving you instructions as we go along. She turned on the cameras and I could hear the faint hum of the five of them. She then took out two more cameras for the still shots, along with several CD's, and loaded both of them. "We're ready now Andrea. The first thing I want you to do is to take the lip gloss on the table, and apply a wet coat to your lipstick. Don't forget to smile. Remember, you're a transvestite that loves to look pretty." I picked up the gloss and started to carefully apply a coat to my lips. Aunt Betty started to take pictures of me smiling in the mirror. Mistress Betty than gave me a key and told me to remove my chastity belt. "Nancy owns the key to the back of your belt, which only means that you will be wearing a butt plug until she removes it. It doesn't mean however, that you can't remove the belt." I unlocked the waist belt, and then the lock on my penis tube, and with quite a bit of wiggling, and some discomfort, the belt finally came off. My penis immediately began to swell until I had the biggest boner of my life.

"Now Andrea, walk between the two racks, and remove your bra." All of the cameras were humming away, and before long I was standing in front of the chair totally naked, and my artificial breasts were large and heaving from the gasping breathes I was taking. "Take the leather bra from the front of the rack, and put it on for the cameras. Remember, you are enjoying yourself immensely." I was sure that she wasn't aware that I was beginning to really enjoy this. If this was what her client wanted, I hoped she sold them all of the photos and they asked for more. I put the bra on backwards, and fastened the hooks. Then I spun it around so the cups were in the front. "I see you've had alot of practice doing this Andrea." I just gave the camera a big smile. Mistress Betty was taking picture after picture from every conceivable angle. When I got the bra over my new tits, I looked at myself in the mirror. The bra had a hole in each cup so my nipples stuck out. I was in heaven. "Now take the matching leather skirt from the other rack, and put that on."

I did that and was standing there dressed in the sexiest black leather outfit I'd ever seen. As the night went on, we went through all kinds of outfits, from outerweaar, to the most sexy lingerie on the planet. The only pause in the action came when Mistress Betty needed more film for the cameras. I was told to walk, prance, and dip like a girl would do. "Oh Andrea, you're the best model I've ever had. These pictures will be a smash. After we're through tonight, and all the magazines are in circulation, you will be the hottest transvestite model ever. When the film is edited and made into a movie, I'll be a very rich woman." I was smiling inside, but I tried not to show the girls how much I was enjoying myself.

"It's time for the best part of the evening. I want you to go over to the box under the clothes rack, and follow my instructions to the letter. Open the box now." When I looked inside, I saw a wide array of cuffs, gags, and many other bondage articles. "Please remove the set of wrist cuffs and put them on. Then take two locks and put them on the cuffs." I did that with little trouble. I was then told to hold up my wrists for the camera. Mistress Betty took several stills of me doing this. "Do the same with the ankle cuffs." I was then ordered to take another one of those double penis gags out and lock that in place. I was getting myself ready for bondage in front of the cameras. "Now comes the most important part of this entire shoot. It better go off without a hitch. I want you to take the dildo with the flat base out of the box, and bring it up to your eyes as if your examining it." I did as I was told. Now walk over to the chair and slide the dildo into the two braces on the seat. Be sure that it is tipped toward me." All at once my heart skipped a couple of beats. I knew I was going to do this one way or another, and I didn't want to make Mistress Betty mad now. I slid the dildo into the two slots. "Next, go back to the box and take out the tube of lubricant, and put a liberal amount on the dildo. Then take some in you hand, and lubricate your butthole." Oh my God. I was going to be forced to take this thing up my ass in front of the camera. When I was through, I was told to stand in front of the chair and fasten an ankle to each leg. I did, and my feet were now locked to the chair.

" Now comes the important part. Very gently sit on the chair until you have taken the entire dildo in you ass." I was shaking like a leaf. I was sure that the cameras would see this, and I would have to do it again. I slowly started to sit down. The dildo started to penetrate my ass, and I was wincing from the pain. "Take your time Andrea. Your muscles will loosen in a minute, as soon as you begin to accept it." After what seemed like an eternity, my sphincter relaxed, and the whole dildo was inside me, and I was sitting in the chair. I felt as if I had to go to the bathroom very badly, but that feeling died down after a few minutes. As soon as I was seated completely, Mistress Cissy came over to me wearing a cat type mask, and locked my wrists to the chair. I was now totally helpless. "Perfect Andrea. You are just wonderful." Sitting in that chair with a dick up my ass, another one sticking out of my mouth, and my own prick as large as the other two, I didn't feel all that wonderful. Mistress Betty took some more snapshots and the turned all the cameras off.

Both of my new Mistresses then took a break to get a snack and smoke a cigarette. "Andrea, please raise yourself off of the chair about six inches. Be sure not to let the dildo come all the way out." I raised myself as far as I could off of the chair as she ordered. "Very good, now sit down again." I did as I was told. "Good, now keep doing that until I tell you to stop. Now Cissy, doesn't she add a new meaning to the phrase, "go fuck yourself"?" Both of them were in stitches. I had to admit that even I thought it was kind of funny. I kept up the up and down motion on this dildo for the next fifteen minutes. "Okay Andrea, you may stop now. I believe you have loosened yourself up enough for what I have in mind for later tonight. I told you that you had to be punished for being naughty. I had hoped to let you relax in your new bedroom that I have decorated so nicely for you in the basement, but now that will have to wait until tomorrow, if you're a good girl and do exactly as you're told until then." All at once I knew what the other room in the basement that I had never seen was. It was my new bedroom.

"Cissy, I want you to release Andrea from the chair now, and take her into the house. Go to the basement bathroom and give Andrea her enema. Better give her two. I want to make sure that she is totally washed out for my game later. I'm going to package up all the film and CD's and get them ready to bring to the studio tomorrow. I'll be down as soon as I'm through here." Cissy then came over to unlock me from the dildo chair. I heard her whisper in my ear. "Well I guess I'm not going to get any of your tongue tonight, but that's o.k. It'll just make me want to cum more times tomorrow sweetie." She unlocked my ankles and then hobbled them, and then unlocked my wrists. "Can I please put Andrea's chastity belt back on her Mom?" "No honey, it will interfere with her punishment." I was led away and into the basement of the house. Cissy brought me into the bathroom and had me bend at the waist. She clipped off the top of the first fleet enema, and inserted all the fluid in my now very sore ass. "I want you to hold that for five minutes, and then you may sit." I held it until Cissy said I could now expel the fluid. After I was through, she repeated the process. "Let's see if you can hold it for ten minutes this time." After a short time I was beginning to double over from the cramps, but I held out until she told me to sit. When Cissy was satisfied that I was all cleaned out, she led me back to where this whole torment started. In a matter of minutes, Mistress Betty walked in. She was carrying an armful of boxes.

Mistress Betty immediately started explaining to me that punishment was no good unless it served to make the sissy want to do better in order to avoid it in the future. "I think I have just what is called for in this situation. It is something I thought of myself, and I must say it is quite good. Mistress Cissy, will you please bind Andrea's wrists to the spreader bar as we did before." Cissy quickly attached my wrists and took great pleasure in locking them into the cuffs. Betty then opened the first box. "This is your diaper. You will need to wear it to prevent any accidents from spilling onto the floor. Mistress Cissy, if you would please put this on Andrea, and be sure that her penis and balls are pulled through the hole in the front. Cissy put the diaper on me and fastened it with the sticky tabs on each side. "Now for your rubber pants." Those were quickly put on in the same manner. My penis had now swollen to full erection due to the thrill of looking at myself in the rubber pants. "Cissy, please get rid of that pole sticking out of Andrea's pants." Cissy went and got another vial and began to stroke me until I couldn't hold back any longer. I soon exploded into the vial with a muffled groan from my gagged mouth. Cissy then took the vial upstairs.

The next box contained a pair of rubber stockings. Cissy put those on my legs, and the feeling was fantastic. Next came a pair of ankle boots with six inch heels. When they were laced in place, my feet had an arch that I knew would become uncomfortable very quickly. "Let's see here. Plastic diaper, rubber pants, rubber stockings and leather boots. That just about covers the clothing. Now for the fun part. My gag was taken out only to be replaced with a black padded one with a hole through it. This let me breathe through the gag. I was really quite relaxed at this point.

Mistress Betty opened another box and I saw a catheter tube with a very large bag at the end. Betty then inserted the tube into the head of my penis, and I began to feel pain until she had it completely in. She then attached the bag to a pole that Cissy had wheeled over. "Now my precious, you can relieve yourself from the front without worry. The diaper and rubber pants should hold any discharge from the rear, but since you're clean as a whistle down there, it shouldn't be much." From there things got really strange. Mistress Betty then inserted what had to be described as a very long straw into the gag. "Now feel for the end with you tongue Andrea. Do you feel it?" I nodded a yes, and she was pleased. The then removed the strangest thing I'd ever seen. As she walked up in front of me and knelt down, She placed a metal ring at the top of my scrotum. This had four small chains hanging down from it with a small plastic cup about two inches high suspended from it. It also had a small hole on each side about half way up. Another series of chains were attached to a twenty ounce cup that hung below the first one. It almost looked like a reverse parachute. The bottom cup had no holes in it though. I heard a click and knew that this contraption was now suspended from my balls. It was very lightweight though, and I was in no discomfort.

Then Mistress Betty took a huge enema bag that was filled to the top with liquid. She hung the bag from the ceiling and clipped the tube onto the end of the top cup. Lastly, she bent the long straw that was hanging from my gag, and put it inside the top cup also. "There, I'm through. What do you think Mistress Cissy?" "Mother, this is the most wonderful punishment that I can ever imagine." What the hell were these two nuts talking about. "Oh, poor Andrea must think I've lost my mind. Let me explain how this works. First, in that enema bag is five quarts of citrate of lemon. That is used in hospitals to make patients go to the bathroom before a medical procedure. It is quite effective. When I release the clamp on the tube, it will drip at about twenty drops per minute. That will fill the top cup until it reaches the overflow holes on the sides. The more the cup fills the heavier it will become on your balls stretching them painfully downward. Now I know that you are thinking that the weight of the liquid in the top cup will never cause you any great discomfort, and you're right. But the fun begins when the liquid starts to drip into the bottom container. You have no way of getting it out with the straw. So the dilemma here is do you wait until the weight of the bottom cup becomes so heavy that it starts to rip the balls out of their sack before you start drinking, or do you start drink right away. I'm sure you've figured it out on your own, but I'll just mention it anyway. When you drink the citrate of lemon, you of course begin to cramp violently, and you will begin to try to shit, but since there is nothing there to come out thanks to Mistress Cissy, all will do is begin to burn terribly. You will have the worst case of the "dry shits" in the history of mankind. Not to mention that five quarts of liquid is quite a bit to swallow, so your stomach will agonize from that also. By the time I come back after breakfast to release you, I'd imagine you'll be begging me to let you do everything I command. I was thinking about sitting with you for awhile to see the beginning of your torture, but since I will have it on film anyway, I can just fast forward through the boring parts as I watch. Have a wonderful and restful night Andrea." With that, the lights went out and I was alone in my soon to be nightmare.

It took about thirty minutes before I started to feel the weight of the liquid on my balls. It wasn't painful enough at that point to cause me any great discomfort. Shortly after that, the top container became full, and the mixture began to drip into the bottom container. At that point I sipped about half of the contents of the top one, and the pressure on my sack was relieved. When it filled for the second time, I let a little more drip into the bottom container before I was forced to drink more to lessen the pressure. I could only guess, but I thought I had gotten through the first hour without any problem. I let the process repeat itself, and more liquid dripped into the bottom container. At that point the discomfort became more evident, and I knew I had to empty the top cup again. I hadn't felt any pain in my stomach, so I was now convinced that Mistress Betty had made a mistake in thinking that this foul device would cause me to be in agony. As the top cup filled once more, I drank all of it so the weight of the liquid wouldn't stretch my balls any more.

Suddenly I began to feel a strong discomfort in my stomach. I just attributed that to the fact that I had drank so much of the fluid. As the pain became stronger, it started to take my mind from the fact that the liquid kept flowing. The cup filled once more, and more flowed into the bottom container, increasing the discomfort on my scrotum. At that point I knew I was the one who misjudged the effects, and realized I was in trouble. I drank the top cup dry again, and the pain in my stomach became quite unbearable. Suddenly I felt that I had to get to the bathroom because my bowels were starting to react to the citrate. I had to shit in the worst way. As I tried to squeeze my rectum to make sure I didn't shit on the floor, the cramps now brought tears to my eyes. The top cup was now completely full, and the liquid was filling the bottom container. I was now in total agony. I tried to relieve at least one of the problems by letting my muscles relax, but as expected nothing came out. It took about one minute before I had to do it again, and before long I felt as if my ass was on fire. I felt an uncontrollable urge to double over from the cramps in my stomach, but since I was spread eagled in a standing position, that was impossible. The bottom cup was now full enough that my balls felt like they were being ripped off. I was now crying a river.

I knew it couldn't be more than a couple of hours since the women had left me like this, and my mind began to wander. I thought of Mistress Betty and Mistress Cissy asleep in their comfortable beds. Just then the door opened, and both of them walked in. "How is my little sissy feeling tonight? Are you ready to be a good girl for us?" I nodded as much as my position would let me. "Very good darling. I know you won't want to see what other nice things I have thought of to insure your obedience." Mistress Cissy removed my gag, and I pleaded with Aunt Betty to let me get some relief. "Where's the smart mouthed little girl I left here earlier? Are you sure that you don't want to defy me with your mouth?" "No Mistress. I promise to do everything you command without question in the future." "Very well. I believe you are being sincere." I tried to stop crying, but the tears just kept flowing. "Mistress Cissy, please take Andrea down, and remove my toys gently. Her little clit must be quite sore by now." Cissy removed the cups that were hanging from my now swollen and painful scrotum, but she couldn't resist a couple of tugs on the ring to hear me squeel. She released my arms and my ankles, and I was allowed to run to the bathroom to finally expel the liquid that had now built up inside my body. When I was through, I half walked and half crawled back to my two Mistresses.

"You will probably find this very uncomfortable, but Mistress Cissy is now going to replace your chastity belt. I don't want you to be rubbing yourself and getting all excited. But before she does that, she will milk you one more time." Cissy then began to play with my penis, and as much pain as I was in, I still found myself getting a raging hardon as soon as she started. It wasn't long before I was dumping another huge load into a container. Cissy then replaced my chastity belt, and it did hurt more than I was willing to admit. She then put the infamous body harness back on me, and my arms were again pinned to my body and I was helpless. "Take Andrea to her new bedroom so she can get some rest. We have another busy day planned for her." I was then led to the one room I hadn't seen yet. As she unlocked the door I saw my new home until I was trained to be their slave. It was a very girlish room, all done in pink with another poster bed. It had a makeup table, bathroom, and a large dresser. It also had one other feature that insured that I would be there when the ladies returned. Just inside the door, from one wall to the other were cell bars. They had a door in the middle. The room was a pink decorated prison cell.

I was ordered to kneel on the side of the bed, and Mistress Cissy sat on the bed facing me. "It's a good thing that Aunt Betty didn't hurt that wonderful tongue of yours. Now get to work sissy." She spread her legs so I could see that she wasn't wearing any panties. I knew that I had to please her or I would be punished again. It licked her for all I was worth. She had three orgasms before she was satisfied. "If you ever say a word to Aunt Betty about being my little pussy slave, you will find out that tonight's punishment was a picnic." With that, she went to the dresser and removed another penis gag and forced it into my mouth. As she locked the cage door, she told me to get some sleep. She would be back in a few hours. I immediately laid on the bed and started to drift off to sleep. Just then I heard the lock on my prison being opened, and it was Aunt Betty. "I see that Mistress Cissy has put another gag in your mouth. Would you like me to remove it for you my darling?" I nodded a yes and Mistress Betty took the gag from my mouth. "I've heard from Nancy that you may be the best pussy slave that she has ever had, so I had to see for myself. Go to it honey." Mistress Betty then straddled my head while I was lying on the bed. She damn near smothered me. I started to lick her and stick my tongue as far as I could inside her. In a matter of minutes she was writhing and almost screaming out in delight. I lost count, but I was sure she came at least four times before she finally fell forward on top of me and laid there to catch her breath. "You are fantastic Andrea. All of my friends will have such a wonderful time with you. I want to keep this as our little secret, so you will not say one word to Mistress Cissy. Do you understand me.?" "Yes Mistress Betty. I will tell no one." "Good girl. I believe that you will make the best sissy model and slave in the world before I am through. You go to sleep now, and I will tell Mistress Cissy not to wake you until you are rested." Mistress Betty then left my cage and started to lock the door. "But Mistress Betty, won't Cissy know something is wrong if she returns to free me and I'm not wearing my gag?" What am I, a total asshole? I was now asking this deviate to gag me so the other pervert wouldn't know that I just serviced her. "Oh Andrea, you are so sweet to be thinking of me at you own expense. I am sure you'll do very well as our slave." She then replaced the penis gag in my mouth and left. Was I starting to like this situation? I knew that I was in for more discomfort before it was through, but I just giggled to myself, and drifted off to sleep.

 

 

 

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