David to Debbie

by Debra Lynn Messer

  

I am writing this to anyone who has ever wanted to take control of a sissy and create a new woman of him.

I discovered my husband's interest in becoming a woman like others have. He was really good at trying to hide it, but as usual, not quite good enough. It started with me catching him on the net. I was at work and "followed" him to a chat room. From there I was able to get him to act out a very intense scene with what he thought was another guy. This went on for a few weeks. Each time I, or as he thought Steve, would come up with a new idea. I had straight sex, forced sex, and even a gang-bang. It was all disturbing and really got me upset and I decided that if David wanted to be Debbie then he would.

This turned out to be relatively easy since David was about 5' 7" and slight build. His features would never be confused with a "Macho" looking guy. I figured with some make up and the right clothes he could pass easily.

One day while I had him on line I was able to learn that he had a few clothes somewhere in the house. I got a good idea where as we chatted I decided that starting this weekend David was going to be seeing a lot more of Debbie. Actually I made the decision right then that Debbie was going to be full time.

I had called in sick one Friday and after David left for work I went on my search. Just as I had thought I found the private collection of Debbie. There were several pairs of matching bras and panties. A few garter belts and stockings. She had nice taste in clothes, several skirts and blouses and even a couple of suit sets and a few pairs of shoes. I noticed that the skirts on the suits were mid thigh in length, others were shorter and the longer ones were looser. The blouses where all light fabric, a few were sheer and the rest easily showed bras. The panties were all thong and either lace or sheer. I noticed a set of DD-cup breast forms and three wigs.

As I went through everything my sissy husband had I made my decision. I carried everything up and put it away. I began by tossing out David's clothes and replacing them with the Debbie's. I figured if this is what he wanted then he should have them. Next I hung the dresses in the closet and placed the breast forms and wigs on the shelf. Satisfied with what I had done I headed off to the store. I figured Debbie was going to need her own make-up and a few more things to wear. I then stopped off and purchased a couple items to begin her training into womanhood. I purchased a dildo and butt plug to use as training aids.

When David got home I told him to go shower. As he was getting undressed I told him to rub himself with a hair remover, well he thought it was some kind of cream. All I told him was that it was part of a little surprise I had for him. He got in the shower and I picked up his clothes. I tossed out the under shorts and put the rest of his clothes in the wash. Since David did not have a lot of body hair what he had came off easily. He was a little worried when I came into the bathroom.

Checking him out I smiled. Very good, I see it all came off. Don't worry honey it looks great. This seemed to work and he dried off and went to the drawer that now contained his bras and panties. I could sense the terror in him when he opened it. Don't worry Debbie your "friend" Steve helped me. With that I smiled and headed out of the room. Oh, by the way. Make sure you wear a bra when you come out too.

A few minutes later David came out in a pair of shorts and a t-shirt. I figured I had the moment and I took it. Well Debbie I see you look relaxed. Let me put it to you simply. You will wear a bra, panties and stockings each day to work. When you get home you will change. I don't want you to sneak around any more. I tried to sound understanding and caring of this new arrangement. I also expect you to keep the house, cook and do the laundry. Now go back in and get dressed correctly. When he came back he was wearing a skirt and top. He had his breast forms in place and make up on. I had to admit he had spent a fair amount of time perfecting his look and did look very good as a woman.

That night I gave him a treat. We have intense sex all night. Granted it was the last time I let his cock touch any part of me again. The closest he would come to sex would be eating my pussy and me fucking him with my dildo. That is until Debbie was ready for a real man.

The next day I told David he needed to consider a diet. He needed to trim his waist and the hormones would add pounds. Debbie was a little to heavy. I gave him a shake and the first of his "vitamins" (testosterone blocker and female hormone). I told him that he needed to take two more at noon and then two at dinner. With that I kissed him on the cheek and headed off to work.

I planned my next stage of training. Debbie would grow out her hair. I would introduce the plug and dildo soon. Then later Debbie would get to live out all the sexual games she and Steve had played. While I was lost in thought a new guy in our office came over to hit on me once again. He was a dish too. Above 6' with thick dark hair and solid built. He had made a play for me a couple times and I had been nice in my rejection of him. Granted that was before I started to transition my sissy husband.

When I saw him I just gave him an inviting smile. Carol, I was just wondering what you had planned for lunch? I knew what he meant and decided a long lunch with a real man like Andy while my sissy husband was cleaning sounded great. I went to my boss and took the rest of the day off. Andy and I went to his place and I sucked and fucked his huge cock all afternoon.

When I got home Debbie was just getting dinner ready. As I had instructed, she was wearing a long skirt and low cut top. The breasts made very nice cleavage and I had to admit she was rather attractive and even passable. That night I made Debbie move into the guest room. I explained that unless I requested her she stayed in her own room.

As the next few weeks went by I took Debbie to the salon to have her hair done. Still not very long I had it styled to a more feminine look. I figured it would be easier to begin to start now. Then I began Debbie's training. That night I had her come to bed dressed in a lacy baby-doll. We were kissing and I had her go down on me. Debbie ate me to several organisms. Then I slipped on the dildo and got her in position. With her lubed ass up in the air I placed my latex love tool at the opening to her fuck hole. Time to learn what getting fucked is like. Then with a solid thrust I pushed it into her. She winced and I drove in further. Relax, and this will be so much more enjoyable for you. I kept ramming the latex cock in and out of her fuck hole. Before long Debbie actually relaxed and began to get into the rhythm of the fucking. When I figured she had had enough I removed the cock and slipped in the plug. You will sleep with that to help keep you loosened up.

The next morning I had Debbie suck on the dong and fucked her again before I went to work. This went on for several more weeks. I would use my toys on Debbie. Training her for her new role in life. I would get my fill of Andy cock nearly everyday. The pills had made Debbie's little cock and balls tiny and limp. Her natural breasts were now a nice size and I made plans for having them enlarged to the DD she liked. Debbie was a full time woman. Her old clothes were long gone. She now went out dressed and everyone knew her as the woman she was becoming.

By now Debbie was under my control. Because of her new body she took a job at a strip bar serving drinks. I liked to come in with a few of the guys I was fucking at work and have her serve us. A couple of times I even got up on stage and stripped just to rub it in. I knew it was killing her but I didn't care.

Then one day I took her to the clinic. The doctor said that she was ready for her boob job. When the doctor left the room my pathetic sissy husband tried to object. Oh, get real; you are more woman now than man. You wanted big tits and now you are getting them. Shut up and just be happy that I will let you have bigger ones than me. The next week Debbie had her surgery and even her nose and voice changed to better fit her new look.

After her boob job I decided that it was time. That day I bought here a pair of red crotch less panties and a matching bra that exposed her nipples. I had her wear a black skin-tight mini skirt that barely covered her ass, a tight white top that her new tits nearly fell out of and a pair of fishnet stockings with 6" black heels that strapped around the ankle. She was walking sex and by the next morning would be covered in it.

Debbie we will be having several guests over tonight. You will do what ever they want. I had told her it was for a game that was on TV and decided to leave out the part that they were all horny men.

As each came in Debbie met them at the door. It was great. They would look her up and down like the piece of ass she was. They would cop a quick feel as they came in too. I could tell she was a little concerned about all the men there. Don't worry Debbie dear. There should be about 7 total coming tonight. I guess they couldn't find a date. I just gave her a little smile. Andy brought the last guy in and I gave him a very passionate kiss in full view of my sissy husband. I could tell he looked hurt, not that I cared.

As everyone got settled I decided to introduce Debbie them to and let her know what was expected of her. Guys, let me introduce you all to Debbie. Debbie is my sissy husband who is becoming a woman. Tonight you get to bring her into the world of pleasure. Debbie is here for you to enjoy. I looked and saw the terror in her eyes. I smiled and went on. Who would like to be first? Mike jumped up and dropped his pants freeing his 9" cock. Debbie, suck that cock the way you were taught. I don't want to see one drop of cum when you are finished either.

I had my sissy husband on her knees while Mike rammed his pole in her mouth. I could tell she was working hard to get the cock down her throat and she was holding on to his ass as Mike held her head and sawed his cock in and out of her mouth. Debbie, you need to relax. A woman can handle a cock that size. You must not fight it. When he was about to cum and he forced his cock all the way in and told her to suck it all down. With a couple trust of his hips I saw Debbie's cheeks fill as Mike shot his cum. Again I told Debbie not to lose even one drop. She did a great job downing his juice and licked his cock clean afterwards.

Then Bill got up and pulled up the tight skirt. I had lubed my sissy husband up for just this purpose. He bent her over so that her ass was exposed and with a quick push buried his rod into her fuck hole. I bet you are glad I loosened up your ass. I could see she was hurt at my comment. Bill just kept ramming his cock into the tight hole. He grabbed her hips for better leverage. It did not take long for Bill to fill her with his cum. When he pulled out the sticky fluid dripped down her thigh.

Debbie you are doing so well. I am sure everyone will be very happy tonight. This will be good for you. You need to get used to sex. All women like to suck cock and have their pussy fucked. Little did my sissy husband know that soon sex with men would be as common as the sun rising for him. All night long they took turns fucking her ass and face. It was like a constant train of cock filling the little whore. I could tell she was beginning to just take each cock as they came. What ever he wanted she gave him. It was getting me so hot I took Andy up to my room and had wild sex with him.

The next morning Andy fucked me and I called Debbie into my room. With my naked stud in bed at the same time I made Debbie eat my pussy. Do like my stud's cum and my pussy juices all mixed together. Lick my pussy clean and taste the cum of the cock that now fucks me regularly. I knew it was cruel but I wanted to make sure Debbie knew the new order. While Debbie was licking up the juices of my cunt I could see Andy getting hard again. When he was fully erect I went into action. Debbie, suck his cock. Suck this pole that has given me so much pleasure. Suck his rod and taste what I have in me now. Debbie wrapped her lips around his tool and began to suck him off. Andy was sucking my tits and biting my nipples while my sissy husband was face fucking his pole. I smiled at what I had done to him. He was now ready for the best part. When Andy came again Debbie, without, prompting downed his load and licked him clean. Very good Debbie, now you know with Andy living here you will have to give us our privacy. I am sure you understand that women need a good fuck and … well … you can't give it.

That day Debbie found out she was going to start dancing. The owner of the club told Debbie that those tits needed to be on stage. I figured a little help from a drug would loosen her up for the first time. Debbie got on stage and did a great job. She did her set and the owner and I took our cut of the money she made. Not bad for your first time. Now you can do some private dances. I expect you to get them into the VIP Room. I smiled at the thought of her dancing for men. I will bring in some friends tonight. Oh yes, find a guy because Andy and I want to fuck alone tonight. I never tired of rubbing my fucking Andy in my sissy husbands face.

As I promised I came back with several guys. Debbie did her sets on stage. Guys would grab a feel every chance they got. The rest of the time she entertained my group. They enjoyed her too. I sat on Andy's lap and he played with my tits and fingered my pussy all night. I told her we were leaving and reminded her the deal. Ted gladly volunteered and I knew as horny as he was Debbie was going to get a good balling.

When Debbie came home she still had the cum stuck to her thighs. Well I see you have done well. I expect you can do as well again. I would like you to meet Ben. Ben makes movies. He has seen you and wants you to star in his next film. I already worked out the details. You go and get cleaned up. You have to get going to start filming.

Ben made porn films of pre-ops like my sissy husband. I decided to go and watch as she got fucked by a bunch of studs on camera. We drove to a huge house that was well concealed. The filming was done in several different rooms. Each room was a different set and outside there was a pool and spa too.

In the first scene Debbie was dressed in a tiny bikini. It was little more than three triangles with string. She was sunning herself when in came her cock. They did a little foreplay and soon Debbie's huge boobs were free and she had her lips around his cock. It was the biggest cock I had ever seen at least 10 thick inches of man meat. I was envious of her getting to suck on such a massive pole. As the scene went on he removed the bottom of her bikini and began to plow that monster into her fuck hole on the lounge next to the pool. Debbie was beginning to really get into the fucking she was getting and he had his entire unit buried in her. This went on for several minutes. Debbie was moaning and grabbing at him as he rammed that giant into her over and over. Then when he was ready he pulled it out and stroked it a few times. His cum shot out over her mounds and into her face, her mouth open trying to catch the jetting cream. He shot cum on her face and tits and rubbed his cock on her when he was done. Afterwards she went off to clean up and change for her next scene.

This time she was a secretary and her boss was putting the squeeze on her. There she was, having to suck off and fuck her boss. He had her bent over the desk and was plowing his cock up her backdoor. He came all over her back and slapped her ass when he was done.

At the end of the day we went back to the club. Debbie today went so well you will be doing several more movies. The guys all liked you and the director liked your body. Please try to find time and do him as a thank you for your stardom that is coming.

After several months of movies and dancing I decided it was time to let her become a complete woman. I sat down with Debbie when I got home. Debbie, next week I have arranged to have you get your pussy. You will be out for several weeks in recovery. Debbie just thanked me. It was easy to see that my once male husband was now totally broken. He was nothing more than a sex tool for any man who wanted him. I was pleased at how easy it had all been. Now Debbie was real and soon to be all woman and I had gotten a new man, one that didn't want to be a girl a real man with a real cock that knew how to drive me wild.

As soon as the doctor said it was okay I had Andy break in Debbie's new pussy. I figured it was best. What do you think? Doesn't he have an incredible cock? It is a least twice the size yours was. Yea, I never tired of that. I had her stripping again too. This club was a nude club so she could show off her pussy. She also came to work at my company. I got her a job as a personal assistant to a manager who was always on the make. I told her that she needed to make sure he was taken care of and just do what he asked.

About three weeks into her new job Jerry offered her to have lunch with him. He took Debbie to a hotel and at lunch made his intent clear. Since all the women had told Debbie to not argue Jerry had no trouble getting her into a room and into bed. As the weeks went on I would see Debbie come out of his office wiping her mouth or fixing her skirt. There was no doubt that Debbie had become just what I had planned, a sex slave to men. Little did I know how good she really was.

Jerry had her move into an apartment close to the office. It was fine with me since I had started seeing a couple other guys and having a roommate was making to tough to just have naked guys waking around. I had figured it was so he could go and drill her on lunch everyday. What I discovered was that she was doing his clients too. They would come in town and stay at her place and she would make sure they were happy and comfortable. Debbie was not only his assistant, but also his personal whore. It was to good to be true.

At the holiday party I confronted her with the news. Debbie said it was all my doing. Ever since I had begun the process she was trained for sex. Now that I am a real woman I use sex as a tool. Debbie makes twice what I make and has an assistant doing the work. All she has to do is keep Jerry and a long list of others happy. She smiled and told me she had to leave because the CEO was taking her home tonight.

  

  

  

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