Crystal's StorySite


A Whole New Life

Debra Lynn Messer


It all still, in some way, seems odd. It has been quite a while and I still am not used to it. I have to admit the trip was great and I am happier now than ever. My former wife and I have remained great friends even after it all.

It really was her idea. Kim and I had been married a while. I was struggling at the job I had and really was wanting more. It had devastating effects on me. I had gained a great deal of weight, was temperamental and unhappy. Kim had learned of a job that was just right for me. It was doing research work. I worked from home and spent hours on the computer looking and comparing and digging. After some time we set up a room in the house as an office where I could work alone.

After a couple of months I noticed I was more content. It was like the new job had created a release for me. That was when it all started.

Kim had me stop by the doctor's office one day. Dr. Sherri had given me a quick look over and a couple of shots. She explained I was a good candidate for a new procedure and would send the information through. I was a procedure to help weigh loss and control. She promised it was safer and nowhere near as radical as the more current procedure. I agreed blindly. I had been fighting my weight it for a while and was ready to try anything.

That evening Kim came home and asked about my visit. I told her everything and she was behind me 100%. She then explained that Sherri had called in a prescription for some pills. In addition to having to stop in every week I was to take these three times a day. I assumed it was all part of the plan.

A week later I went in for the surgery. It took about an hour and I was told to only drink health shakes for about a week and check in with Sherri. So I did as they instructed. Sherri gave me my usual shots and noted my weight in a book. She said it was a list of ten patients that were also involved in the procedure.

Over the next few weeks I noticed some changes. I was loosing an average of 10 pounds a week. I also noticed I was shaving less and had less hair on my body. What concerned me most though was that I felt as if my hips were wider and that I was developing breast tissue. Actually I had real breasts. Then it began to occur to me I was changing in my groin too, and it was not a change men would want. Sherri told me it was just the effects of the drugs. She made it sound like it was no big deal. I tried to get more out of her but Kim just calmed me down and reassured me it was fine.

I found myself acting differently. I was becoming more sensitive. My skin was getting softer and I was having feelings that were kind of strange to me. I really couldn't figure it out and every time I asked I got the same old line.

Now two months into the process I was really getting concerned. Sex was out of the question. I had nice sized breasts and my waist and hips looked more like Kim than me. Nothing I owned fit anymore so I figured it was time to go shopping. Kim and Sherri said I would loose about another 30 40 pounds so I kept my shopping simple, very simple.

Before long I had lost 16 inches in my waist. I had hips that flared out nicely and my chest was a solid C-cup. I looked at myself in the mirror and noticed what looked like a woman's body in front of me. That is except for my lifeless dick. Since I had been working at home I had grown my hair longer. Not long by any standards, but long enough to cover my dress shirt collar. The longer I stood there the more I came to the conclusion I was being changed. My wife and Sherri were changing me into a woman. I decided to confront them both.

When Kim came home I started with her. She stuck to the story for a while then confessed. I was angry. I was screaming at her for this and wanted to know why. She looked at me and explained. I knew you had dressed in the past. I knew you hadn't in a long while. As time went on you changed. Your attitude got worse, you gained weight, you were constantly unhappy. I figured if you saw yourself as a woman and even lived as one for a while you could decide. You could choose to remain that way or give it up. I wanted to know about it all. Kim explained if I quit now it would slowly go back. In time I would be the way I was. Please give it try for a while though. See if you are okay with the choice. I was at a loss for words. There had been a time I would have done anything for this. I paced around and went into my office to think about it.

A couple hours later Kim came in. Well, did you decide? I said that I would for 90 days. That would be long enough. Kim then led me to the room next to my office.

To make this work you need to go all the way. She had bought several things for me to wear, everything I need to go out dressed as a woman. She even had bought me my own make up. Come on we need to style your hair and get you ready to start tomorrow. This will be your room during this period. This way you can live as a woman without any influence. I agreed and went to the salon.

The next day I showered and got ready. I found a pair of sheer white bikini panties and matching bra. I choose tan stockings that did not need a garter, a mid-thigh length dark blue skirt and cream blouse. I was trying to repeat the process, with little luck, that I was told day before. No matter how I tried my make up looked terrible. Kim stopped in and talked me through it on her way to work. I spent the entire day locked in my room with the curtains drawn.

That evening when Kim came home she insisted we go out. I tried to argue, but was reminded of the agreement. There is no way you can be sure if you don't live fully out in public. I tried to explain I was 6 feet tall. There was no way I wouldn't be read. Kim came into the room with a pair of low heels. There are lots of tall woman here wear these. I knew I had lost and followed her to the car.

Dinner went fine. No one even locked twice. Granted Kim had to correct me a couple times on being more "lady like". I was very concerned about how I appeared in front of people. Later we went to the mall and shopped some. I was becoming aware that I was getting better at this. By the time I got home I was comfortable with being dressed and around others. The next day I went to the store alone and found it was easy and comfortable. I had no trouble being seen as Debbie and nearly skipped out to the car. With each passing day I felt better about being me. Maybe Kim was right.

Then came a test I was not ready for. One day Kim told me she had planned a double date. Don't worry, it is a simple date and nothing will come of it. I did worry though. Here I was looking, acting and living as Debbie. What did she have in mind? What did she want out of this? She kept telling me it would be okay and not to worry.

Kim helped me get ready for the date. I wore a short tan skirt. My top had a deep neckline that showed a fair amount of cleavage. I had on a lace thong and matching bra and low tan heels. I was just finishing up when I heard two cars pull up. Kim introduced her date as Bill and mine was Dan. They were both very tall. Standing next to them I felt fine. We went out and Dan opened the door for me as I slipped into the car and swung my legs up and in.

Dinner was great. Kim and I were both having a good time. Later as the guys ordered dessert Kim and I slipped off to the ladies. See, no problem. Like I said this is just a date, a chance for Debbie to go out with a guy. I smiled and nodded my head. We finished up and joined them at the table. After dinner we left. I noticed that Dan turned and was headed a different way then Bill. Dan was driving towards the hill overlooking the town. Here I was in his car and he was headed to a make out spot. As he drove he took my hand and placed it on his thigh. I don't know what came over me but I became to caress his leg. Moving further towards his package each time. When he pulled up to a spot he turned off the car and looked at me. I stopped stroking his leg.

Why did you stop? I said I wasn't sure. Dan leaned over and kissed me. My head was spinning. What was happening? Why was I not pushing him away? All I could do was respond to his kiss. As we kissed I could feel him pulling up my top. I let him take it off me and helped him take off my bra. Dan was sucking and biting my tits. I was moaning softly as he did. I was confused. Here I was making out with a guy and I was enjoying it. Then I reached out and touched his rock hard cock. I began to stroke it and then freed it from his pants. Without thinking I went down and wrapped my lips around his member. I had to try a couple times to get it all into my mouth I ran my tongue along the underside of his rod. I could tell he was enjoying it as he ran his fingers through my hair. I kept sucking and sucking his shaft. My face was fucking his pole and I was really getting into it. I could feel him getting rigid as he was about to cum. I help his cock and sucked as it began to pulse. I could feel it shoot into my mouth. His thick cum filled my mouth. I swallowed as quickly as I could to keep up with his load. Afterwards we headed back home. Kim was still up when he dropped me off.

So where do you two go? I had Bill drop me off so you could come in right away. I told her he jut drove me around. He had wanted to do something but I kept it simple. You should have gone with it. How else are you going to know what it is like? Kim kissed me on the cheek and went to bed. All night long I lay in my bed wondering what I had done. I kept replaying it in my mind. The most shocking part to me was that I did it willingly. I wanted to do what I did, actually enjoyed it.

A couple days later Dan stopped by. It was about 10:00 in the morning. I knew Kim worked in the city and would not be home until nearly 6:00 that evening. I showed Dan in and asked why he stopped by. I just wanted to see you again. I led him to my office and sat down across form him. I tried to get comfortable, but all I could think was how much I had enjoyed his cock and that I wanted it again. I guess he sensed it because he came over and gave me a deep passionate kiss. I eagerly responded to it too. He then got me to my feet. Before I even knew what I was doing I had his pants around his ankles and his cock in my mouth. I was sucking it for all I could when he came. Again I eagerly downed his sweet juices.

Gawd, that was even better than last time. You really know how to suck dick. I didn't know how to tell him I was new at it. Kim said you needed to experience everything a woman experiences. I was shocked. He was here to seduce me at Kim's request. With that he produced a letter. I read it and it said that I needed to do this. It was important for me to do it so I could make my decision. I folded it up and kissed Dan again.

I helped him take off my clothes. He was caress and sucking on my tits. I was going wild at his touch. Again I began to stroke his growing cock. This time though he lifted my legs and placed his rod at the opening of my fuck hole. Dan took some lube and slicked up his cock and my ass. Then he slowly began to push it in. I was in pain as he did. He would push and then stop so I could relax. Then when I did he would begin again. I noticed that once he was well in me the pain stopped and I had a warm feeling throughout me. Dan kept pushing until he had his entire unit in me. I could feel his heavy ball sack against me. After I relaxed he began to slowly slide it in and out. He would pull it out until only his swollen head was left in, and then push it all that way in. I began to moan as he did. As he began to fuck me harder I began cries of joy. I wanted his cock. I wanted to feel the joy and pleasure a man gives a woman. He continued to drill me as I wrapped my legs around him. I wanted to feel him deep in me. I was panting and short of breath when Dan rammed his cock deep in me and let loose his load of hot cum. I pulled him close to feel it shooting deeper in me, the warm cream coating my insides.

We had sex one more time before Kim came home. I was just getting dinner ready when she walked in. So I assume Dan stopped by? Did you have sex with him? I didn't know what to say. I wasn't sure I could tell my wife that a guy had come over and fucked me silly, twice. I know you did him. Dan told me how much he licked it. So, did you? Did you find the joy of a well-hung stud filling your pussy with his meat? The sensation of his come as it flows inside of you? I tried to tell her as little as possible. I let her decide how much I liked it, or didn't like it.

That night it was all I could think about. I wondered if I had told the truth what would have happened. Would I be given the chance to become Debbie? Would I get a real pussy so that men could eat me out and fuck me? Would it really bother me so much if I were able to leave my male body forever and become a complete woman? All these questions kept filling my mind.

The next day I had to drop stuff off at the office. I didn't see a problem with that. Since no one really knew who I was I just said I was Debbie and had to drop off some notes. While I was there I met a guy. He was tall and really handsome. He told me his name was John and asked me out for a drink. I suggested his place. When we got there I wasted no time going after him. I had his cocking my mouth and was sucking him hard. I downed his cum and began to get him hard right away. I wanted more. I needed to get drilled by this guy. He did it too. This time I swear the entire building heard me getting screwed. He was amazing. I was shaking when he came. After I got dressed and left I felt I was walking in air. I couldn't believe how great he was.

I had just gotten home when Kim called and said she had to go out of town on a trip. Our firm got the contract and I need to go there. Don't worry it will just be me and here is my number. With that she hung up the phone. I went and showered. Here I was now having fucked two different guys and I was married to a woman. Not only a woman but also an incredibly hot woman. Kim was tall, about 5'10" and had a 38d-26-36 body. Her long blonde hair and green eyes were to die for. She was incredibly sexy and an animal in bed. No matter how I tried to rationalize it I was torn. Not about what I had done, but how I could tell Kim I enjoyed it and wanted more.

About an hour after she called I heard a knock at the door. It was John for the office. I nearly went weak. He was all I could think about and I wanted more of him. I let him in and asked him what brought him by. Kim said you would be home alone tonight so I decided to stop by. I asked him what he meant. Kim had me meet you earlier today just to see what you would do. I told her you were nice and polite. I lied, so she wanted to see if it would be better if I came here. I smiled and led him to my room. There I was again on my back with his incredible cock buried deep in me. John fucked me so hard I could barely move. I just lay there as he got up. My whole body tingled from the sex we had just had. At about 10:00 I called Kim.

I asked how everything was going. I am fine. Did John stop by? He promised he would. Debbie you need to learn what women know. Every guy is different and sex is wonderful. I envy you right now. Here you are, hopefully, getting laid by every guy you can. I tried to get a word in. She just kept talking about her meeting and the new contract. Then how I needed to experience live as a woman. That I was doing so well so far. She went on how wonderful sex is with all men. That each knows how to please a woman. She talked for nearly two hours. Finally she said she had to get some sleep and would be in the office at 8:00 in the morning. By the time she got off the phone I needed more cock. I climbed back into bed and proceeded to stroke John hard again. I sucked on his half hard cock and felt it grow in my mouth. John was moaning as I continued to suck him wanting to taste his cum. John decided that he had other plans. Just before he came I rolled me over and filled my back passage again. It was even better than before. I fell asleep with his cock deep in me. The next morning I gave him a final blowjob, as he got ready to leave. I was really enjoying the feel of a hard cock in and the taste of warm cum. I went and showered and dressed for the day.

Kim called early in the afternoon. Change into something hot, we have dates. I went and got ready. I decided on a black lace thong and matching bra and garter. I slipped on a pair of seemed sheer stockings and clipped them to my garter. I then chose a very short leather mini and red top that barely covered my bra. After I got all made up I found a pair of 3 inch black satin pumps. No sooner was I ready than Kim raced into the house. She quickly changed and looked nearly as hot as I felt. You are going to love these guys. They are tall, built and from what Fran said your date is hung like a horse. She was touching up when the bell rang.

Gawd, was she right. Ted and Tony were hot. Tony and I left in his care and Ted and Kim followed behind us. We went to several clubs that night. Finally Tony decided to take me home. Kim wanted to stay out longer and Ted said he would too. As soon as we got inside Tony took me in his arms. I am glad they decided to stay. I hate audiences. I knew what he wanted and was ready and willing to give it to him. I led him to my room and began to undo his pants as we kissed. I pulled them down and freed his cock. I gasped when I saw it. He was easily 10" and so thick I could hardly wrap my fingers around it. I thought to myself if I could handle it all. I kissed the purple head and stretched my lips around it.

It took some effort but I got it all in me. I had his rod in my throat. It was so huge it was hard to breath. I had to hold my breath as I sucked his cock, every now and then pulling out for air. Tony held my head as I sucked his monster. He had incredible control too. I was getting sore form sucking his cock when he came. Wave after wave he shot into my mouth. I swallowed every last drop of his juices. Sucking all I could. When I finally released his softening shaft from my mouth.

Tony then stripped my clothes off me and went to work on my tits. His strong hands nearly covered them. He pinched my nipples and had them hard and erect in no time. He was sucking on them and driving me wild as I reached for his cock again. Tony got me on the bed and I lubed my love hole and his massive member. With a little effort Tony glided it deep in me. I shuddered and screamed in joy as he buried his cock in me. Drive after drive of his massive pole sent me further over the edge. I shook as he pushed it all the way in and help it there. He fucked me for what seemed like forever I reached levels I never thought possible. When he came I shook, I actually shook. It was like nothing I had ever even dreamed about. I went to the kitchen to get some water and met Kim in there.

She was naked and held a finger to her mouth. I hear Tony gave you a major balling. Is he huge? I just nodded and smiled. Well Ted is far from small. I hope he gets me as hot as you were. I had actually heard my wife say she was about to fuck a man. The surprising part was it didn't bother me. I just wanted a glass of water and another screwing like I had just gotten. Tony did me again that night and again the next morning. I sucked him off one last time in shower and kissed him at the door. I could hardly move from his cock and fucking he gave me.

A little late Kim came down to my room. Well, I guess I don't need to ask. So are you ready to become Debbie? I thought about it and looked at her. Come on, you have never been happier then over the past few months. I heard you last night. You were in total ecstasy as Tony fucked you. Never at my best could I have driven you as wild. You actually enjoy a man's cock as much as I do. At least that was what John and Dan told me.

I smiled and admitted I was happy. Sex with them had been great. I even admitted I was ready to try more. Kim laughed and hugged me. So now what? I can't be married to a woman can I? I want men as much as you do. The decision was made. Two weeks later I went into the hospital. When I came out I had DD-cup breasts, a higher voice, surgery on my nose, cheeks and chin and my very own pussy. After having to wait through the recovery time I went wild. Over the next several weeks I fucked every guy I could. I downed there cum and had them fill my pussy and ass. I had grown to like my backdoor rammed and even after the SRS allowed men to screw it.

We got a simple quiet divorce and I moved across town. We still see each other often and even go out and date. Since I have become Debbie I haven't been able to stop. So many years of denying myself the joys of womanhood have left me wanting all I can get.




2003 by Debra Lynn Messer. All Rights Reserved. These documents (including, without limitation, all articles, text, images, logos, and compilation design) may be printed for personal use only. No portion of these documents may be stored electronically, distributed electronically, or otherwise made available without the express written consent of StorySite and the copyright holder.