Crystal's StorySite


Becoming Debbie

Debra Lynn Messer


I am writing this at the direction of my former partner.

My name was once Brian. I am 5'7" and measure 38DD-24-36. I was born male, but some time ago I began the journey to Debbie. I was transformed into Debbie, a live in maid and servant to a woman that was once my wife. I am now a soon to be bride and wife.

It started when she learned about my online personality. I had been hitting chat rooms as Debbie. I described myself as having long dark hair and eyes and DD-cup breasts. I had started a relationship with a guy named Steve. I acted out all sorts of sexual fantasies with him. In each I was totally submissive and dominated by him.

One day Carol talked me into trying something. I was open to the idea and did as she asked. I was given a tube of cream and told to rub it on myself. After about 15 minutes I showered and noticed all the hair on my body coming off. I was really worried about it too. Carol was pleased at how clean I looked. She then shaved around my cock and balls to "shape the area up". When she was done I went to the dresser to get a pair of under shorts. I was shocked to see the panties and bras I had stashed away. I looked at Carol and was at a loss for words.

She just smiled. Your friend "Steve" told me where I could find those. Why don't you get dressed and meet me in the kitchen. Please make sure you wear a bra, woman do no matter how much they may hate them. With that she left the room.

I was not sure what to do and chose a pair of panties and matching bra and went to finish getting dressed. I opened the next drawer to see all my shorts and t-shirts gone. So I picked a pair of woman's shorts and a top and went to meet her.

She was sitting at the table when I came in. What no boobs or wig? Look I know all about it. I can accept it. Here it is for you right now. You have a home wardrobe and a small work one. You will always wear panties, bra and stockings. At home you will finish the look in something feminine. I expect you to always look and dress as Debbie here.

I tried to argue with her. There was no way out though. She knew it all. I went back to the room and finished getting ready. When I came back she was cooking.

Look, she said, I just don't want to have you sneaking around. This way you can be Debbie all the time. At least at home. She corrected herself quickly. You will take care of the house and do the shopping and what ever else I tell you.

I agreed to the plan and figured it was better than the alternative. I was a little surprised at how calm she was. I tried to think that there was more to this, but she insisted there wasn't. I guess that was why I didn't see the rest coming.

About a week later Carol came home with a friend. She introduced her as Dr. Carrie. She then introduced me as her husband Debbie. I was horrified. I was dressed and now meeting people as some freak. Carrier was cool an acted as though nothing was going on. I was left with her while Carol went to change. After some time Carrie produced a couple of veils and bottles of pills. I took the shots and Carrier gave the veils to Carol.

Carrier then explained that the pills needed to be taken three times a day. I went into the kitchen to check on dinner and heard them mumble something about breast implants and minor surgery in about six weeks.

That night Carol told me that while I was talking to Carrie she had moved my things into the other room. You will need your own room now. You will keep mine clean and come in only when asked.

Now I was worried. That night Carol and I had incredible sex. It was the best I had ever had with her. No sooner did I cum than she went to work getting me hard again. It was also the last time I ever used my dick that way.

It only took about four weeks for me to have to quit my job. The shots and pills were testosterone blocker and female hormones. Because of the changes in my body I could no longer go out in male clothes. One day while out Carol destroyed the last of my clothes. I figured since your C-cup breasts keep you from dressing as a male you didn't need them any more.

Carol had changed. She came and went as she pleased. She treated my more and more like her servant. Two weeks later I went with her to the hospital. When I go home my C-cup breasts were now DD and my face had softer features and my voice was higher.

Now Debbie you will be my maid. I have bought new clothes for you. You will be in uniform each day. You will have one day and one evening off. You will stay in your room in the back unless you are working or requested. I expect breakfast to be ready by 7:00 and dinner by 6:00 unless I call. You have a phone in your room to use and an intercom so I can reach you.

With that she left me to my new space. I checked out the closet. I had several basic outfits. Most of my other things were gone. I had some very short tight skirts and low cut tops. My nicer outfits were gone. All but 1 pair of my shoes were at least 5". I had uniforms to wear while working. Most were simple dresses and dark flats for the everyday duties. The others were the frilly type for evening and cocktail parties. Carol had said she would be out for the evening and not to bother with dinner before she left. Since I was not at all hungry I settled in for the evening.

The next morning I fixed Carol her breakfast and began to tend to my duties. It was odd having such large breasts. I had to relearn a few things. I managed to work through the day and was pretty pleased with myself. Carol had called and told me that she would be having guests over that evening for cocktails. I was to wear my black outfit and 5" heels.

That evening I was all dolled up when the guests arrived. Before long there were about eight men in the house. They all settled in when Carol called me into the room. Gentlemen, as you know this is Debbie. Debbie is my housekeeper. Debbie is also a man in transition. I almost died. Why had she said that? What would have made her say such a thing? You have been invited to help Debbie in her next step. Debbie knows how to look, act and present herself as a woman. What she needs is to discover what it is to be a woman, to have a man take her. Would any one like to help?

With that a guy got up and stepped forward. I was told to get on my knees. I undid his pants and lowered them to the floor. There in front of me was a rock hard cock. It was easily twice the size of mine. Carol instructed me to suck his pole. I began to kiss the head. Again I was ordered to stick it in. I opened my mouth. I gagged on the size of his tool as he pushed all the way into my mouth. Relax Debbie. A woman just has to relax and then she can easily take a cock that size. It took a couple tries but I finally was able to get in all in. Then he held my head as he began to saw in and out of my mouth. He was slipping it all the way in and I could feel his balls slapping against my chin with each drive. His cock swelled and he shoved it all the way in. With a couple short thrusts he shot his hot juice into my mouth. It was creamy and smooth, not at all like I thought it would be. I actually kind of liked the taste as it jetted out of the head filling my mouth. Don't let any out. I would hate to see a mess on the floor. I just sucked until I was sure he was finished.

Then the next guy came over and pulled down my panties. Carol took some lube and slicked it all over his hard pole. I got in position as I felt him line his cock to my virgin fuck hole. Now please try and relax. Sex is a wonderful thing. A big cock is a joy. He began to push his rod into me. I cried out in pain as he did.

This went on for hours, each of them having there way with me. I couldn't believe she was just watching me be treated in this manner. When they were done I went to my room to clean up and change. In there I just cried. How could she have done this to me? Just then I noticed Carol in the doorway. What is taking so long? You need to clean up and come back. I just stared at her. Look Debbie you are a woman and women give themselves to men. You are also just a maid. Look at yourself. Your cock and balls are worthless now. You have developed a great body and men want it. Beside Lenny will be staying tonight with you, so hurry along. With that she left the room. I showered and scrubbed the cum off me. I dressed in another uniform and returned to the front room.

Lenny was alone. He got up and came to me. I led him back to me room and at his request stripped naked. I them stripped him down and began to suck on his cock again. It did not take long for Lenny to cum. Afterwards he laid me on the bed and softly caressed my body. He was gentle sweet and before long we were having sex. This time I gave in and it was nice. We feel asleep with his cock still in me.

The next morning Lenny and I woke early. I had sex with him again before getting dressed. I saw him to the door and went to start coffee for Carol. I could hear movement in her room but did not know what it was at first. As I was getting things out in the kitchen she called. Please come to my room. I stopped at the door to Carol's room. It was open some and I could see the back of a guy in the bed with her. I nearly cried. There I was seeing my wife with her legs wrapped around this guy as he screwed her. I remembered what she had said. The drugs had made my tiny dick useless. The surgeries had changed me into a woman. I waited in the hall until I heard them stop moaning and yelling then lightly knocked on the door. Ah, just in time. Debbie come and eat my pussy. I climbed on the bed and went down on her. As I started to lick and suck on her box she lay back. MMM, you do that do well. Lick me clean. Taste my pussy and the cum of this sexy man. Suck he seed down. She kept this up and orgasm twice before she let me stop. When I got up I noticed her lover's cock was hard. Debbie I think you need to service his cock now. Again I went down on his cock. Isn't that a wonderful cock? It is so much larger than your was. Take it all in, suck the cock that services my pussy. Suck the cock of a real man, a man that wants to fuck women. Drink his cum. Taste the cum of a real man, not some sissy bitch. I finished his cock and while they were in the shower replaced the cum covered sheets.

I returned to the kitchen to get their breakfast ready. I served then and saw them both off at the door. The rest of the day I tried to block the experience form my mind. Here I was and it was my fault. I was a maid to my wife and a sex tool to her and her new men. I stopped and looked at myself in the mirror. She was right. I was 5'7" and had huge tits. My waist was small and hips wider. My shoulder length hair was styled and all made up no one could ever tell I was a male. I slowly resigned myself to the fact and tried to accept that I was now Debbie and Carol was a woman who wanted sex.

That night I stayed away from Carol. I did not want any contact with her. I was angry at her for what she did and angry at myself for letting her. That night as I lay in my bed I thought about what had happened over the past couple months. I remembered how much I looked forward to chatting and feeling like I was living the life on line. I remembered how much I had always wanted breasts like these and a body like I now had when I was younger. I guess I was upset at the thought of loosing Carol. The group sex was humiliating but in bed with Lenny was something I had always wanted. I decided that no matter how upset I was I was getting what I always wanted.

A couple weeks later Carol had me go shopping with for a new dress. I need you to come with me on a date. I wasn't sure I liked the idea at first. It is a double date and you need a fine dress for the date. We went to several stores until we found and red sequent dress that was about mid thigh length. The dress had one shoulder and cut at an angle across my chest and back. It showed a nice amount of cleavage and leg. Then we found a pair of 6" red stiletto heels that strapped around my ankle. When we got home I went to get ready for dinner. After I showered and dried my hair I picked a sheer red thong. I did my hair up and off my shoulders and neck. I stepped into the dress and zipped up the back. Looking in the mirror I was impressed. A quick check of my make up and then I rolled on a pair of black seemed stocking and strapped on my shoes. I grabbed my black clutch and stood in front of the mirror. I had to admit I did look incredible. I met Carol and my date in the front room.

Dinner was wonderful. Dan was my date and he was a dream. All through the meal I was in a trance. He was tall, a little more than 6', dark wavy hair, and built real well. Carol had introduced me as her roommate. I could only have wished so much. We danced several times and I was really getting turned on by him. After dinner I saw Carol and her date head towards home and Dan asked if I wanted to see his place. I agreed and we drove to a place overlooking the city.

His home was beautiful. The view of the city at night was like gems on a velvet cloth. I was standing on the balcony when he came out with a glass of white wine. I never get tired of this view. He wrapped his arm around my waist. I turned to face him and wrapped my arms around his neck. We began to kiss. My parted lips invited his tongue in. As Dan pulled me close to him I could feel his cock getting hard against my thigh. He led me back inside and to his bed room. As Dan stood behind me I heard the zipper coming down on my dress. I let it fall to the floor and stepped out of it. Then he pulled the pins letting my hair fall around my neck. I turned around and began to take off his tie and shirt while his strong hands cupped and caressed my breasts. When we were both naked we slipped to bed and I went down on him. His cock was huge. Easily 10" and so thick I could hardly wrap my hand around it. His balls were heavy and large. I found it easy this time to down his cock. I sucked and licked his cock and balls. As my mouth fucked his rod his breath was becoming short and quick. I downed his cock and sucked hard as he got closer and closer. Then when he couldn't hold back any longer his cock erupted with the warm salty man juice. There was so much I had a hard time downing it all. I worked as best I could to keep up with the fluid pulsing out into my throat. I sucked every last drop and licked him clean. Later Dan had me on my back with my legs wrapped around him as he fucked me. I fell blissfully asleep in his arms, filled with his seed. The next morning we had sex again before he took me home.

When I got home I was greeted at the door by a woman dressed as a maid. I was puzzled by it but happy it wasn't me. She seemed to know who I was and led me to the large bedroom in the front of the house. I noticed that all my clothes were now in there. More importantly, the uniforms were gone. I turned to thank the woman who introduced herself as Dawn. My room was smaller than the Master bedroom, but it still had a private bath. I checked the drawers and noticed a small overnight bag sitting on the bed. As I looked around Carol came in.

I see you had a good night. So do you like the new room? I had it redone a few days ago. I figured since we have a new maid your room should be nicer. I did like the look. By the way I have a surprise or two for you. The first is that in a few weeks you will be working for my firm as a Personal Assistant to Dave Muller. I know he is rotten, but I figured you could handle him. I looked at Carol and waited for the next bit of news. Oh, we will be going to the hospital today. Seems you are ready to have that "thing" down there removed. You should get ready. If you need anything…well you know how to reach Dawn. With that she left the room. I had to sit a moment. It was a little shocking. I had given into the fact I was a woman. Now I was about to leave and become one completely. I took it all in. I was a little surprised at how well I felt about it, then again why not. I was no longer Brian and Carol and I really were nothing more than roommates now. I came to the conclusion that I should feel good about it. I grabbed the bag and opened it up. Inside it was some clothes, personal items and two folded sets of papers.

After I showered and got dressed I set on my couch and opened the papers. The first was for Carol and Brian's divorce. I was a little upset and had to take a few deep breaths. It was simple; basically she was buying me out. She kept everything and I got a pile of cash. Granted it was not a huge pile but a fair amount. I would receive it 1 month after returning to work should I go back. The second was for surgery. It outlined what was going to happen and the usual legal stuff. I signed it right away and then stared at the other one. It took me some time to rationalize that it was the only thing to do. I was Debbie now. Carol needed a man. I found out last night that I wanted one too. I was ready to move on also. As I thought about what had happened and where I was going from here Carol came in. Are you ready to go? We really need to leave soon. I smiled and grabbed the pen. I wrote my name on the line and folded up the paper. I then set it on the dresser as I picked up my bag.

While I was in the hospital and then at home Dan came over to visit me. We had begun to develop a relationship. Then came the day I had waited for. The doctor said I was fine and could do what I wanted, and what I wanted was to give myself to Dan as a complete woman. I left the office and went home. I grabbed a few things and told Dawn I was planning on being gone a couple of days. I then met Dan at work and broke the news to him. His face lit up and I knew what was on his mind. That night I gave in to him and he fucked my new pussy. The next morning as I stood naked in the bathroom I admired the woman I now was. I knew I had to thank Carol some day for leading me here.

I moved into Dan's place and we are planning a wedding soon. I don't work and have decided being Dan's wife and partner is more important. Carol is still single and I really think she enjoys the sexual freedom it gives her. I look back and the only regret is that I wish I had become Debbie sooner.




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