Bridesmaid
By Jackie Lynn
"Jackie please come and help me". I quickly started to go upstairs stopping for a moment to check my appearance. In the hallway full-length mirror a pretty maid looked back at me. From the perfectly made up face down to the sexy black maids uniform with the very short skirt, black seamed stockings and 4 inch heels everything looked in place except for one thing, I am or should say was a man!
"Jackie what is taking you so long to come"! I quickly made my way into mistress's bedroom. " Yes mistress "I said. "Jackie you do need to be a little quicker when I call you". " Sorry mistress it will not happen again". Looking at my mistress was enough to take my breath away. She was dressed in a white wedding gown that was absolutely gorgeous! As I think about how good the dress looks it occurs to me that I am thinking as a woman would when shown a pretty dress, not like a man would. I don't remember thinking so much about how any type of dress looked when I was a man but now I regularly used words like gorgeous and darling in describing things. Another thing that is out of place in looking at my mistress and admiring her dress is that my mistress is or I should say was my wife! How did I get this way? Let me tell you the story.
John! Can you please help me? My wife of 5 years was calling me again. All I want to do is watch this football game. I slowly make my way into the kitchen and Debbie is standing in the middle of the room hands on her hips looking very angry. " John you don't help around the house at all and I am tired of your attitude"! "What attitude"? This sent her into orbit. "John I can't go on like this, we have to go to a counselor". At this point I was going to do anything to calm her down. Debbie I will do anything you want. "Good, I have a friend from college who is a counselor and can help us out. "Ok when do we start"? "I will call her tonight"
That night Debbie called her friend Stacy and made an appointment for the next day. Dr. Stacy Brenin's office was very fancy with a very pretty secretary at a desk in the waiting room. I could not get over the dress she had on, very short and tight with very high heels. I could not help my self and took a long look at this ultra feminine creature. On her desk was a sign with the name Christine. Christine saw me staring and smiled back with her perfectly made up lips and sexy eyes. " John! It is time to go in". Debbie was getting up and walking toward the open door to Stacey's office. Stacy was a very attractive woman about my wife's age with dressed like successful businesswomen. "How are you doing John"? She held out her hand to me, which I shook. "Very well Stacy" I said. "Please sit down" Stacy indicated we should both sit down. "What seems to be the problem?" Stacy asked? " John does not seem to want to help me around the house" Debbie said. I started to talk and Stacy interrupted. " John this is common and I think we can help you be more sensitive to your wife's needs" Stacy said. I could not get over how this so-called counselor was handling this session. Every time I tried to tell me side of the story I was quickly interrupted. So the session went on like this with a couple of outcomes. I was to try to be more sensitive to my wife's feelings by trying to see things from her point of view. I also was to come to the next meeting alone. Meetings where to be held once a week. At the end of the meeting I noticed a silver chain on Stacey's neck which for some reason I could not take my eyes off of. The next thing I knew the meeting was over and we left the office. I can't explain what happened at the end of meeting but I did feel very calm.
The next week went as normal but I found my self helping my wife much more often. The day before the next session with Stacy I was getting dressed and found that I had no underwear left. Stacy told me to wear a pair of her panties, which I did without protest. I thought it was strange that I did not mind wearing the panties but for some reason I did and also liked the feel of them. I could not stop thinking about how good they felt all day. The next day I put on panties without question. My session with Stacy seemed short to me but from the time I went in until the time I came out took an hour. Again I looked at the chain and lost track of time.
The next 3 weeks went about the same except now I put on panties even though my underwear drawer was full. Stacy questioned this and I told her I liked the panties. She smiled and said we should go out and get some for me, which we did. At first I picked out plain panties buy progressively they got more and more feminine and sexy. I can't explain why but it just occurred to me that I needed them. At the end of this three weeks I was wearing sexy lacy panties without question. I even had a pair of thongs, which were very uncomfortable, but I still liked the feel. All this time Debbie did not seem to mind and in fact commented on how much she like the panties on me. Each session during these three weeks went as the first one did. The last one however I was given a shot by Stacy and some pills. For some reason I did not question the shot or pills and began taking the pills every day.
About four weeks into it I was getting dressed and saw a waist cincher with garters on the bed. I picked it up and started to put it on. As I did this Debbie entered the bedroom. " What are you doing John"? " I'm sorry Debbie". I started to put it down and Debbie said" If you want to try it on it is ok with me, but first we need to shave your legs to make it look right". I then went to the bathroom and shaved the hair off my whole body except for my head and around my genitals. I don't know why I did this. I came into the bedroom and Debbie helped me into the waist chincher. She made it very tight. She also had me put on seamed black stockings and attached them to the garters. Once this was all done I put on my panties and went to work. Each day from then on I wore some kind of corset. My waist was getting smaller and smaller and I wore a jacket all the time so people would not see the outline of my corset.
Debbie also asked me not to cut my hair or cut my nails at this time. She like the way my hair was beginning to look and said I had to stop biting my nails. My hair all of a sudden needed to be put into a ponytail for work and my nails under Debbie's constant attention soon became as long as some women I see. Debbie even began to paint my nails with clear polish. At the next meeting with Stacy I told her about all the things going on with me and she said I was just seeing things from Debbie's point of view and was very proud of my progress. This made me feel very good and after the usual loss of time at the end of the appointment I was on my way home. I had to stop a the mall for a few things and for some reason I was at a earring stand in the middle of the mall getting first one ear and then both ears pierced. I came home with little studs in both ears to Debbie's delight.
After about six months I was constantly wearing a corset, stockings and panties under my clothes during the day. My hair was shoulder length and when not in a ponytail it was very feminine looking. Debbie even had me go to her hairdresser to trim my hair. After this was done I noticed that my hair looked much more feminine then it used to. My nails where about an inch long and perfectly kept. I also started to wear camisoles under my shirts to hide the straps of my corset. I noticed the cups of the corset starting to hold some of my chest. I asked Debbie about this and she said not to worry it was the corset pushing the excess flab up to the cups and was not a problem. This is funny because Debbie had me on diet, which I could tell was working on my waist, which was done to 25 inches. My ass and hips seemed to be getting bigger though. At night at this point Debbie had me wearing nightgowns which I grew to love.
Debbie seemed to be more and more in charge. If she told me to do something I did it now without question. Debbie wanted oral sex from me more and more. Regular sex between us was starting to become less frequent and for some reason I was having trouble performing anyway. Debbie would tell me to get on my knees and service her giving me tips on how to please her. I became very good at this but my release was not as regular as hers. When I asked Debbie about this she would tell me it was time I saw it from her point of view. Once she said that I never asked the question again. One night Debbie gave me permission to have regular sex with her and I could not achieve an erection. I started to worry but Debbie started to play with my nipples and soon I orgasmed without getting hard just from Debbie playing with my breasts. This seemed strange but I did not question it at all. The sessions went on and on with each week I would become more and more feminine. At it bothered me but soon I started to like the idea of looking girlish.
Then one day Debbie asked me if I would do her a big favor. I told her I would do anything for her. Debbie said Stacy was having a big party and needed serving maids for this event. She had one drop out and needed help. I told her I would be happy to help. Debbie said I needed not only to help but also dress and act as a maid. At first I told her I could never do that but Debbie kept talking about it with me and finally I said yes.
About a week before the party I had my usual appointment with Stacy and she told me how happy she was to have me help out. She also said Christine would be helping too. I thought about this and could not wait to see Christine in a maid's outfit. When I got home that night Debbie said I should start to practice being a maid. On the bed was a maid uniform. Debbie helped me put it on, fixed my hair into a feminine style, and make up my face. I put on some 4-inch heels and walked over to the mirror. I could not believe it I looked like a girl! This bothered me for a minute but then I became intrigued by it. Debbie also had me sit down again and painted my long nails red. She also plucked my eyebrows to thin lines. I started to protest but it was too late. How was I going to go to work tomorrow?
I started to come home every nightdress as a maid and under the constant supervision of my wife soon became very good at walking, moving and talking like women. Debbie was very pleased which me feel good. At work all this became a problem. I could not stop walking and acting feminine. With my long hair and my mannerisms I soon was being talked about at the office all the time. For some reason it did not bother me. I also at this time began to wear women's pants and blouses. Men's stuff just did not feel right. This made for lots of odd looks from my coworkers.
Finally the night of the party came. I quickly dressed and put on my makeup, which I could now do pretty well. My corset was pulled very tight getting my waist down to 20 inches. I put on my shoes and Debbie put in large hoop earrings in my ears. I was ready to go. As we arrived I saw Christine. She was wearing the same dress I had on and looked fantastic! I went over to her we started to talk. She complimented me on my dress and said I was making good progress. Not knowing what she meant by that we started to serve drinks and food at the party. Debbie and Stacy where at the same table with two guys Jim and Bob from Debbie's work. At first this bothered me but became used to it as the night went on. I saw Debbie dancing with Jim to a slow dance and then kissing for a long time. This really started to upset me and I went over to Christine to talk to her. Christine said I should not let it bother me. Christine pointed over to Stacy who was dancing and kissing Bob and said that did not bother her. I told her I was married to Debbie and it was different but then Stacy said to me she was married to Stacy! I looked at her with a puzzled look and Christine went on to tell me she is really a man and is married to Stacy! I told her I did not believe her. With that she took me to a backroom and pulled down her panties. Under her panties was a very small penus with a ring through the tip attached to the scrotum. This made Christine have to sit and pee like a women. Also I notice she had a chain going to a plug in her ass! I asked about it all and she then said mistress Stacy like her this way and she is now used to it. I could not believe what I was seeing. I asked about Christine's breasts and she said they were all hers. At this point I had a million questions but we could hear Stacy calling for us. We then went on to serve at the party. At one point I lost track of Debbie. The party was over and Christine and I cleaned up. Still no Debbie. Stacy and Christine gave me a ride home (Debbie took the car).
When I got home Debbie was not home. I went to bed. In the early morning hours Debbie came home. She looked tired with her clothes all wrinkled. I was very angry and confronted Debbie. She said she was out with Jim and enjoying her self. I told her she was married to me and it was not right. " Look at yourself John or should I say Jackie, you are dressed in a night gown and cant even be a man in bed". This hurt but she was right. Debbie then went into detail about how she and Jim made love and how good it felt. I started to cry and Debbie told me to get on my knees in front of her. She then told me to clean her up which I did between the tears.
I continued to go my appointments with Stacy and came to accept my wife's behavior. I was told to see it from her point of view. I was not really much of a man anymore and how could I deny my wife of a real man. At this point I looked more like a women then man and had to go to great lengths to get ready for work. I had to pad my waist to hide the curves, use a sports bra to compress my breasts (which now filled a B cup), take my nail polish off (I painted them every night), put my hair into a pony tail, take off my earrings and make sure to take off my makeup. Even with all these efforts one day my boss called me into his office and told me it was my last day. I knew the reason and did not even ask. I came home and told Debbie. She was in the process of getting ready for date with Jim. "Well Jackie (she called me this all the time now) I guess you need a new job, you will be my maid now". She went on to tell me that I was to move to the guestroom and wear my maids outfit all the time. She said we would buy more uniforms soon. Also I was to address her as mistress. I complied without question. That night she brought home Jim and I could hear their love making into the night.
I then adopted a new life style. I now wore a maid's uniform most of the time with a very tight corset; my waist was now down to 18". I was used to doing all my duties in 4-inch heels. I had my hair cut and styled into a female style with bangs. I wore makeup all the time and had my ears pierced in three places in each ear. With all of Debbie's direction I now walked and talked just like a women. Anytime I would do something un-ladylike like I was punished. At first Debbie would spank me but soon she was using whip on me or worse. I did not cross her much. Debbie also loved to talk about me to Jim, telling him how useless I was as a man and at least now I did a valid function in her life. I had not had real sex with my wife for an entire year, which was not a problem, since I could not achieve an erection anyway. I did service my wife orally usually after she had sex with Jim.
I now went to my appointments with Stacy dressed as women. Under the direction of Debbie I would usually wear a mini skirt, a tight blouse and high heels. I looked as much woman as Christine did now. Stacy would always compliment me and I became more and more subservient to Debbie. One day Debbie told me to get dressed in some loose clothes. We went to a piercing shop and I had my penus pierced like the Christine's and attached to a butt plug. Over the next couple of weeks Debbie would introduce larger and larger plugs until she was satisfied I would hold the largest available. With the plug in me now Debbie had control over my bodily functions so I had to ask her to go to the bathroom. I also found out after a time that I needed the plug at all time.
One day Debbie told me I was going to school to learn how to be a maid. I did not understand this and thought I was doing a good job but Debbie insisted. The next thing I knew I was in the Maid Training Academy. The first thing that happened is I was put under and woke up with size D breasts, my voice changed, a nose job, lip implants, the bottom ribs removed, implants in my hips and some facial surgery to soften my features even more. While I was recovering from all this I had electrolysis all over my body. Once I was fully recovered I at first could not recognize myself. I had a playboy centerfold figure with a face to match! I was then put into training as to how to serve as a maid. I went to classes on how to think like a women, talk like a women, stand and move like a women. These classes over a period of time taught me to do all these things like second nature. I was taught to put on makeup not only on my self but also on other people. I learned to style hair as well. I now knew how to wear any kind of women's clothes and match colors perfectly. The last part of the course was the hardest; I had to learn how to be around men, how to flirt with them, talk to them and finally how to please them. It began with courses on eye contact and speech, then dancing and finally touching. I learned how to give a blowjob and receive a man analy . At first I protested but as time went by I accepted all this without question. I became very good in all departments.
The day finally came for me to go home. I was dressed in a short sundress that showed off my curves and breasts. I felt totally comfortable walking in my 5 inch heals with my hips swinging. I was driven home in a cab. The cab driver kept looking back at me so I used my training to see how he would react, I started to put lipstick on and lick my lips in my compact. I thought he would drive off the road. Finally I pulled up to the front of my house. Getting out of the cab allowed me to arouse the cab driver again. I walked up the stairs with my hips swinging. I tried my key in the door and the lock was changed. I rang the doorbell. Debbie appeared and asked my I help you? I told her it was I Jackie! She could not believe her eyes. I had been away for 8 months at this point and I did not even know how drastic a change it was. Debbie looked me over and called for Jim who was now living with Debbie. Jim looked at me with lust in his eyes. Once inside Debbie told me to dress in my uniform. I did and found it did not fit anymore, it was too tight in the chest and too loose in the waist. Debbie had another uniform in her hands. This one was low cut and tight around my 16 inch corseted waist. It also had petticoats under it to make the dress very short and stick out. I was now ready for work.
My life then became pleasing Debbie and Jim. I dressed Debbie, put on her makeup fixed her hair and did everything she asked me to do. If Jim wanted a blowjob he got one. If Jim wanted to use my ass he did. I learned to please Jim very well. I soon found ways to enjoy it too. My penus at this point was very small and did not produce much these days. My breasts and ass provided most of my pleasure. Debbie would ask me service her almost every day. I was not allowed to kiss her or touch her in any way other then as directed. This became hard to do when dressing her. I would find my self longing to touch her breasts when I put her bra on. A lot of the times I would stand by and watch Jim touch Debbie in ways I wanted to. Debbie would tease me with this all the time.
One day Debbie came to me and said it was time to get a divorce. I asked why and she laughed. " I can't be married to a women," she said. With that the papers where signed and Debbie was no longer my wife and went back to her maiden name. I also had my legal name changed to Jackie and got all my identification to indicate I was a female. I now was just a maid for Debbie and Jim. One day Debbie told me she and Jim were getting married and I was to serve as a maid at the wedding. Again I did not resist. Debbie also told me how I came to be in the situation I was in. She told me about the procedure used by Stacy to turn me into what I was today. I couldn't do anything about it now.
So here I am fixing my ex-wife's makeup for her wedding day. I was sitting on the wooden stool with my legs crossed like Debbie had me do so I would crush my little penus even more and do her makeup. At first this position would hurt real bad but after months of doing it I don't even notice it. I can sit like a girl for hours without a problem. Debbie's makeup was almost complete when her maid of honor stormed into the room with the news that one of the Brides Maids was sick and not going to make it. Debbie was crushed what could she do? Then she looked at me and told me to go get the dress that was supposed to be worn by the sick bridesmaid. I brought it to Debbie and she had me get out of my uniform and put it on. I could not believe it but was a little big in the waist but everything else fit perfectly. The dress was a long evening gown, strapless, low cut and backless. I had to put on a different waist cincher because of the back. With some pinning the dress fit. I put on the shoes (they did not fit as well as the dress) put up my hair, fixed my makeup and was ready to go. I could not believe the situation I was in. I was a bridesmaid at my ex wife's wedding. The wedding went perfectly, my wife made a beautiful bride. I had to dance with my partner. I noticed Christine also dancing at this wedding; she looked happy in the arms of a man. I went over to her during a break. She looked fantastic in a very reveling dress. Christine told me she was happy in her role and wanted to complete the process but that Stacy would not let her. I thought about this for a long time afterward. Would I want to go through a complete change? I was more woman then man but I still could not do it for now. After the wedding was over we all saw Debbie and Jim off to their honeymoon. I went back to the house and resumed my work as a maid.
One day as I was mincing about the house on my 5 inch heels I looked at the mirror for a long time. I was Jackie now and I was beautiful. I guess this is what I am supposed to be.