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Sissy Training

This is a true story, looking back it is hard to believe it actually happened, but it did.

I was working for the government in DC and living in Maryland and my fiancé was up near Cape Cod. Just about every weekend she’d fly down or I’d fly up to spend the weekend together. We’d been doing this for about a year since I took the job in DC. Our sex life was fantastic. We’d role play, put each other in light bondage… all sorts of fun things. I knew she was bi and we occasionally would invite another woman to join us. She also knew I liked to dress up. We’d often go to the local thrift stores and buy sexy things for both of us. We even went to a shop in Georgetown and bought a pink satin maids outfit that she’d have me wear and serve her! Most of our fantasy talk in bed was either about me being dressed up or her being taken by a BBC or another woman.

One night we were relaxing having a glass of wine and watching a movie. Sue mentioned that she had seen an ad online for a place in downtown DC where a woman by the name of Lady Ann trained guys to be sissy maids. We talked about it for a bit and she could tell I was getting excited by the thoughts… we made love right there and it was fantastic! Sue didn’t mention it again and I pretty much forgot about it.
A few months later my birthday was coming up. Sue told me she had an awesome weekend planned for me. She told me she was taking the day off and flying down early Friday and was hoping I could at least take the afternoon off. I picked her up at the airport at noon and we went back to my apartment. We had lunch and the subject turned to the weekend plans. Sue pulled a piece of paper from her pocketbook and handed it to me. She told me that she had two possible plans… one if I agreed and signed the paper and another if I didn’t. The paper said that I agreed to do as she ordered me to do and if I did not follow her instructions I gave her permission to send photos of me to whoever she wanted. I asked her what it was she had in mind but she said I’d find out IF I signed the paper. So, I asked what the other plan was and she said a trip to the museums in DC. So I signed the paper….

“Good, I was hoping you would” she said. “Now let’s get you ready”. The rest of the afternoon was spent getting me dressed up in my pink satin maids outfit, complete with petticoat! I had all the hair on my body removed, toenails painted hot pink, makeup completely done, a tight new white lace corset, a new wig I hadn’t seen before and my 5” black heels with the padlock to make sure I kept them on. I felt so sexy and just knew we were going to have a fun evening. I was told to go sit in the bathroom and wait. I heard the Sue rummaging around a bit and then heard the door open and close, then a short time later open and close again. I wondered who could be here but when Sue opened the door and told me to come out were still alone. Sue then surprised me when she said “Ok, let’s go!” “Go where?” I replied. “You’ll find out, no more questions, do as you are told” Sue shot back. “Yes, ma’am” I quickly responded. “That’s better” Sue said.
I was nervous and excited as I left the apartment. I had been out dressed before but always in something that sort of fit in… never dressed as a frilly maid. Soon we were headed down the highway towards DC. We drove to a section of DC I had not been to, all older stately townhomes that looked almost Victorian. Sue pulled over to the curb and parked. We sat there for a minute with me looking around wondering what we were doing. Sue pulled a note from her pocketbook and handed it to me. It said:

You are to get out of the car, go to the trunk and get your suitcase then go to #327, knock on the door and when the door is answered say “My mistress Sue sends her regards”. From there you will do as you are told. I will be back later to pick you up.

I already knew I had to do as I was told so I took the note and got out, went to the trunk where I found a pink suitcase, the kind you would expect a little girl to have. I took it and turned around looking at house numbers. As I did Sue drove off and left me standing there. I looked up to find I was at #312. Not only was #327 several houses down but across the street. But, what choice did I have. So, off I went. I figured the only way to do it was to look like I knew what I was doing so I tried to confidently walk to my destination. All dressed up in a pink satin maids outfit with a pink suitcase. Surprisingly people going by didn’t seem to pay much attention. I found the house and knocked. A striking woman dressed like she just came from church answered the door… I was afraid I was at the wrong house but I said what I was told to and she simply replied “Yes, come in I have been expecting you”. She told me I was to call her Lady Ann in the presence of others and Mistress at all other times.

I was shown to my room where I put my suitcase and then brought downstairs where Lady Ann began my training. For the rest of the evening and most of the following morning I was schooled in the finer art of being a sissy maid. Domestic duties, housekeeping, washing delicates for mistress, how to curtsy, how to answer the door and greet guests and more. Every half hour or so I was quizzed on my lessons so far and took a crop to my bottom if I got any wrong. I only took the crop a few times and was proud of myself and looking forward to showing Sue what I had learned. I was expecting that Sue would pick me up in the early afternoon, but that didn’t happen.
Lady Ann took me into her office and presented me with a “Sissy Maid” certificate. A nice pink fancy one that she told me would look good on my wall at home. She then told me that my “advanced training” would start in 30 minutes. I figured I was in for more domestic duties, perhaps cooking or waiting on the table.

My training began with Lady Ann asking me if I had ever had a cock in my mouth. I told her that although I had thought about it I had not. She had me sit in a chair, my arms were bound behind me and for the next hour I was schooled in the art of cocksucking with her using dildos of various sizes. I was taught how to lick and suck a cock and balls. She started with a small 6” dildo and worked her way up. The biggest was a really double dildo that had to be 24 inches long and I could barely open wide enough for! She kept pushing more in and telling me to relax. The more I relaxed and kept from gagging the more she pushed in. Finally I had taken about 10” and couldn’t take anymore. She told me I had done well and untied me and told me to take a break and come back in 15 minutes.
When I came back the chair was gone and a bench in it’s place. Again I was tied down and Lady Ann asked if I ever had a cock in my ass. I told her that I had been taken by dildos a few times but never a cock. I knew what was coming… starting with the small dildo she used each on me ending up with that monster 24” double dildo which I think I took about half of it in me. “Mistress Sue will be so proud of you, you have finished the training she ordered, hopefully you will do as well in your practical exam” Lady Ann said when she finished. My head reeled as I realized that Sue had set up all the training and that I wasn’t done… what could the “practical exam” be?

I was told to return to my room and rest and that someone would be up in an hour or so to get me ready for my practical exam. I did as I was told and without being told to I changed from my maids outfit to a frilly pink nightie and laid down on the bed. I must have dozed off because I was awakened by a large woman with red hair. She was dressed in jeans and a sweat shirt. For a moment I thought it all had been a dream and this was reality but I was shocked back when the woman ordered me to strip and get in the shower in a very stern voice. I did as I was told and when I came out she had what looked like a big toolbox on the bed and told me to sit in the chair she had placed at the center of the room. No sooner had I sat but she went to work doing my makeup. I wasn’t allowed to see at all and she took almost an hour just doing the makeup.

She took a blond curly wig and using some sort of wig cap which she glued to my head she was able to do my hair in some sort of updo which I still couldn’t see. She did all my nails in a hot pink. Then she took out what I recognized as fake breasts but very real looking. There was a small wire with a noose on the middle of the back side, the noose was put around my nipple and the breast glued into place. They felt heavy and actually jiggled when I moved. She reached up to the left breast and squeezed the fake nipple on the end, I felt a small electric current hit my nipple underneath, the longer and harder she squeezed the more intense the shock. I moaned and she smiled and tested the other one. She finished by blending my fake rack to my chest with some sort of latex makeup so well that if I wasn’t wearing them I couldn’t tell where real and fake began and ended.

There was a knock at the door and Lady Ann came in carrying a garment bag which she hung on the closet door. She smiled and told the large woman that she had outdone herself. She then opened the garment back and took out a gorgeous pink knee length gown. Almost like a wedding gown but knee length and pink. The two woman proceeded to dress me, first in a white lace corset that pushed my fake breasts up and out. Then a pair of backseam stockings, and white and pink frilly sissy panties. The dress was next and it fit perfectly. A pair of matching 5” heels, a set of rhinestone earrings, necklace and rings and the two stepped back and admired their work. They complimented each other and told me to follow them. I followed them downstairs and as I got to the bottom of the stairs I faced a full length mirror on the wall. I was floored to see the gorgeous woman looking back at me. I had often seen makeover pictures of crossdressers and fantasized about doing that someday but this was different more like a real girl than I could have imagined. So that’s what Sue was up to. Lady Ann interrupted my thoughts and called me into the other room where she had a camera and started taking pictures. She took several in various poses and I began to enjoy it. I couldn’t wait to show Sue. But then I wondered what my “practical exam” was and why were my nipples wired in?

The doorbell rang and I stood there motionless. Neither of the two women moved to answer the door and I wondered who would move first when I realized they were staring at me and it was MY job to answer the door. I hurried over and opened the door to find a tall, handsome black man who asked if Lady Ann was available. Recalling my training I showed him into the living room where Lady Ann was waiting. She seemed to know him well and they took a seat and began to chat. As trained I remained standing and asked if I could get them a drink and Lady Ann told me to get her a glass of wine and George would like a beer. I brought the drinks and Lady Ann motioned for me to take a seat on the opposite side of the room.

Lady Ann and George whispered to each other and would occasionally look over at me. This went on for about thirty minutes. George looked at his watch, set down his beer and announced that it was time to go. I stood to see our guest out and as I arrived at the door Lady Ann told me that it was cold and I should really have a coat. Puzzled I turned to find her holding a white fur jacket and a handbag that matched my dress. I put on the jacket and took the bag and I was still trying to comprehend what was going on when I felt a sharp pain in my rear, like a needle and Lady Ann leaned over and whispered “Something to help you relax my dear”. With that George took my hand and led me out the door to a car with a driver waiting at the curb.

What happened next was like one of those fairytales and I can hardly believe it happened even looking back on it. George was a perfect gentleman as we headed off in the car. I felt a bit lightheaded but warm and tingly at the same time. We headed towards Bethesda arrived at some large building I had not been to before. When we stopped the driver came around and opened my door and George helped me out. He took my hand and we headed in. I suppose I should have been afraid that someone would recognize me but I didn’t recognize myself. I was turning heads of some of the men and I noticed a few get scolded by their wives for looking. The performance was the Washington Philharmonic Orchestra. As we sat George said hi to another black man sitting beside me and to a woman sitting in front of us. I really felt like a woman out on a date and got the feeling that George came often and probably had season tickets if there was such a thing for the orchestra.

We were nearing the end of the performance and I had settled in and was feeling very comfortable, probably thanks to the shot that Lady Ann gave me before I left. It was dark as the orchestra played and I snuggled close to George when all of a sudden I felt a jolt in my right nipple and realized George was squeezing my fake nipple hard. I looked up and he had a faint smile but did not look at me at all as he continued to cause the nipple to be shocked. Then my left nipple but this time it was Georges friend that was pinching and sending the shocks. I could feel my cock getting hard under my dress and panties but was not in any position to do much about it. The orchestra finished and as the lights came up my tormenters ceased. We got up and made our way out with the crowd. I was still a bit dazed by the shocks I had gotten and clung to George as we waited for the car to be brought around. The man that had sat next to us approached told George that he was having a small gathering at his house and would like us to stop by if we could. George told him we’d try to at least stop by.

The car arrived and George helped me in and slid in beside me. “What did you think of the performance” George asked me as we drove off. “Very nice” I replied, “I’ve never been to the orchestra”. “I especially liked the ending” George stated with a smile and put his arm around me. His fingers found my right breast and he squeezed the nipple harder than before. The shocks to my real nipple were more intense than ever as he pulled me closer. His other hand grabbed mine and he pulled it to his crotch where I felt a huge bulge forming. “Lady Ann says you know what to do” he said as he pulled me towards him more. I fumbled for his belt and zipper and soon freed the huge cock he was hiding. I knew exactly what to do and soon had him deep in my mouth. He held me down and started to fuck my face, gently at first and then deeper and harder. I was expecting him to cum soon but heard the car slow and the driver announce that we were at our destination. It was a nice home in a well-to-do section of the city. The large circular drive was full of cars and I felt a little nervous about being in a group of people dressed as I was.

George put his arm around me and told me to relax as he walked me to the house. Once inside we were greeted by a maid in a simple black maids dress who took my coat and brought us to the main room. I excused myself and went to freshen up. I fixed my lipstick as I had been taught and returned to find George with a group of men and women. He smiled as I approached and introduced me to the group as “Michelle, a student of Lady Ann”. The group seemed to know what that meant and looked at me with smiles. Looking around I realized the room had a small low table in the center surrounded by sofas and chairs on both sides. Others had started to take a seat as if getting ready for something but George continued to stand at one end of the room. As my eyes adjusted to the dim light I realized that Lady Ann was sitting near the center talking to the man that had invited us.

As I looked across the room I was shocked to see Ann sitting on a sofa. She had on a red PVC club dress that I had bought for her. I had cutouts down the side and pretty much kept her from wearing any underwear. She had never been willing to wear it out in public but here she was. A tall blond in a short leather skirt and white top sat down next to her and handed her a drink. I almost fell over when she leaned over and passionately kissed Sue, her hand sliding over and feeling her breast while she did. I was turned on by what I saw and knew I’d have to keep an eye on her the rest of the evening. I thought I’d walk over and say hi and see if she recognized me but as I tried to move I felt George tighten his grip and whisper “Stay right here, slut”. I froze, not sure if I heard him right. I didn’t wonder long as George led me to the table in the center and told me to kneel on it. I hesitated for a second and didn’t even hear the crop before it landed on the back of my thigh.

I climbed onto the table. Out of the corner of my eye I noticed Lady Ann rise and she spoke to the group “Friends, thank you for coming tonite. Mistress Sue and I wanted you to witness the final examination for one of my latest students, relax, join if you wish, and enjoy”. My head was spinning. Was she talking about me? I looked up and found a big black cock staring at me. I opened my mouth and took it in just as the flash from a camera went off. I felt hands pull my sissy panties down and another cock poking at my rear. Just then I heard George say “Here you go baby gurl” just as he slid deep inside me. I cried a bit in pain as he tried to push his huge cock in.

I simply was too big. I felt a sharp sting in my arm and knew I had just been given another injection of something but couldn’t see who gave it to me. My boy pussy was still being stretched but George was too big! The cock in my mouth filled it completely and for the first time I was grateful for the lessons I had received. I started to feel a bit strange from the shot just as I felt someone hold one side of my nose closed and hold something under the other. “Here babe, take some poppers” I heard someone whisper in my ear. I breathed in deep and it was repeated on the other side. A camera flash went off as I took the cock in my mouth deep. I could feel the poppers staring to make me feel… well, slutty and wanting… I looked over and remember seeing Sue on her knees in front of the woman in the leather miniskirt. Her face was buried in her pussy and she was going at it like it was the end of the world. The combination of the poppers and the shot were really starting to hit me and I remember thinking that I needed to get up and maybe take a break.

Just then George thrust again and this time his cock slid deep inside me. I wasn’t going anywhere. I looked up as the cock in my mouth thrust deep again and saw guys lined up on both sides. Two of them reached down and squeezed my fake nipples causing the shocks and making me moan. I felt the cock in my mouth pulse and then erupt shooting cum deep in my throat. I swallowed and swallowed again. He pulled out and I gasp for breath but it was soon replaced by another. I wanted it and more. I knew I had been trained to take my place and serve.



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