Crystal's StorySite


Good-Bye Robert

Debra Lynn Messer


My wife and I had a pretty good thing going. She had known about my desire to dress as Debbie long before we got married. Not only did she not mind she actually helped me develop my look and wardrobe. It all seemed so great. Then after we had been married a year things began to change. Now Robert is gone and Debbie is engaged and lives with Rachel.

It began one afternoon. I had come home early and went inside. I heard several women in the house laughing and enjoying them selves. It sound like they were having sex in a way but I couldn't believe it could be true. So I slowly followed the sounds to the Master Bedroom and cautiously peeked in. There was Rachel and several others all naked and pleasing each other. I quickly slipped back down the hall. I knew Rachel had been involved with other women in the past. I had to admit it was rather kinky and I actually wanted to see more. I fought the urge and went into the kitchen. I intentionally made some noise and soon Rachel came in wearing only her robe.

Robert, when did you get home? How long have you been here? I just smiled and said long enough to know, but not long enough to enjoy. Did you watch? Why didn't you say anything? I reassured Rachel that I had seen and new, but I had slipped away not wanting to freak anyone out. Rachel thanked me and told me to wait. A few minutes later all the women came out and told Rachel they would be back tomorrow. I met them all and said hello before they left. I tried to Rachel I was sorry about them leaving, but she cut me off. Don't worry about it. It is fine and they will be back tomorrow.

Later that evening Rachel told me what the plan was. Tomorrow you will dress in your maid's uniform. You will be dressed as Debbie, but you can't join. This is for us, not you. My only concern was being seen as Debbie. I had gone out a couple time with Rachel, but never seen as a maid all dolled up and everything. Don't worry you always look great. Then I told her I liked the idea. I decided it would be fine and agreed to the plan. Besides it would give me the chance to watch.

The net day Rachel helped me get dressed and ready. I was wearing a black satin maid's outfit. The deep front showed lots of cleavage. I had a frilly petticoat that made the short dress puff out. Rachel had helped me die my shoulder length hair a deep auburn color the night before. Now I had it shaped some to look better.

After I was done I helped Rachel get ready. She was wearing a red lace teddy and robe. I clipped her red seamed stockings to the garter and check to ensure that the seems were strait then got her red 4" stiletto heels and slipped them on her feet. Thank you Debbie, I assume will show my guests the same treatment. With that she went to wait for the others to arrive.

As each came in I stayed in the extra room. I watched them strip naked and hand me their clothes to hang up. I neatly placed their clothes out of the way and helped them dress. It was intense. Her I was fixing their outfits. Touching these women and none of them thought anything of it. I was adjusting their clothes and feeling the bodies. It was like a dream come true. They all kept calling me Debbie and when dressed left the room. I served them and was at their call the rest of the afternoon. I watched these hot women having sex with each other. Then later I helped them change back and showed them out.

You were a dear today Debbie. Did you enjoy yourself? I know my friends were very pleased with you. I told her I did and enjoyed myself.

Rachel smiled and that night I had sex with me still dressed as Debbie. It was incredible. I came as soon as I touched Rachel after watching them all afternoon and Rachel got me to cum 3 times after that. I was so exhausted I just collapsed and fell asleep.

When I woke up in the morning I noticed it was 9:00. I panicked and ran to take a shower. Rachel came in and told me not to rush. She explained she called in sick for me. I finished my shower and was drying off when she met me in our room. I want you to dress for a day out as Debbie. I want to go shopping and have to visit a friend and I would prefer Debbie come along. I agreed to the idea and went and found a nice mid length skirt and blouse to wear. I picked out a sheer white bra and bikini panties and got ready. I checked my breasts to make sure they were good and fixed my hair. By about 10:30 I was ready to leave.

Our first stop was the mall. I think we hit every store there. I was glad I had chosen a pair of low heels, there was no way my feet could have taken much more. Then we had lunch with a couple of the girls for the day before. They acted as though I was just another girl friend at the table. I had to admit it took me a moment to relax after what I had witnessed. Then finally we stopped at a doctor's office. The doctor was one of the women from the day before also. I was led into a room and Rachel joined me. The doctor came in and introduced herself as Carrie.

She and Rachel had a little small talk and sheet wrote a couple prescriptions out. Rachel took the sheets and put them in her purse while Carrie went and picked up a couple of needles. Carrie then told me the shots were for me. I was a little worried but figured Rachel knew the doctor and there was no way Rachel would want to hurt me. We then stopped off and had the pills filled and went home.

The next morning Rachel told me that we were starting a new diet and exercise plan. I had no trouble with the idea as I thought I could use it anyways. You need to take these pills three times a day as part of it. You also need to see Carrie each week. I just nodded and agreed thinking nothing of the plan. That day at work I sat down with my boss and finished working out the details of my new job. Since I worked mainly on the computer the company was going to start telecommuting. I had been working there for about three and half years and was selected as one of the first to be involved. I had fixed one of the rooms in our house up to serve as a work space and was ready to begin.

Over the next few weeks I noticed some changes in my body. My skin was softer and more sensitive. I had hardly any body hair and I never shaved. My hips were wider. The diet was working wonders. I had lost nearly 25 pounds and a little more than three inches off my waist. Since I worked from home Rachel suggested I dress all the time and grow my hair longer. I had even noticed that I was beginning to develop breast of my own. I also got to be involved in more of Rachel and her friend's games. After six weeks my chest had grown to a C-cup. I was a little concerned but Rachel, as usual made me feel good about it. That was when things got a little wild.

The next time the girls got together I was allowed to join them. I wasn't allowed to touch but I was instructed in how to suck on a dildo. They explained how to get the entire 9" of it down my throat. Then they breached my neither regions with it. Again they were gentle and caring as they fucked me with their toys. My only concern was that I noticed that my shrunken cock and balls never got hard. Again Carrie and Rachel reassured me it was nothing to worry about. After they finished Rachel had me slip in a plug. She said it would help me loose for next time and I should use it every day to loosen up more.

True to her work the plug did work. The next week I was able to enjoy the treatment so much more. Again any erection was out of the question. I was able to take the dildo down my throat and in my love canal easier. I found myself enjoying the experience too. Maybe more than I should have, but I couldn't help myself.

The next morning Rachel woke me up. Debbie, you need to hurry. We have an appointment to get you to. Just shower and get dressed. I had schedule a two-week vacation at Rachel's request. I had no idea what she was talking about and got up and got in the shower. I was brushing out my now long hair and when she came into the bathroom. Here you go Debbie. All you need is something simple to wear and don't worry about make up. I put on my bra and panties and then the sweat pants and top she had brought me. I then put on a very light layer of make up, just enough to look presentable. I came down and got right into the car. I figured Rachel had something planned for breakfast so I didn't ask.

When we got to the clinic I was led into a room and handed a robe. I was told to strip down to my panties and sit on the bed. I did and a few minutes later Rachel and a nurse came in. The nurse had me remove the robe and lie back on the cart. Then she started an IV. I started to ask why I needed that. Rachel chimed in quickly. Don't worry Carrie said you need this today. She will see you soon. Then she will tell you how every thing went. The nurse put a shot into the line and in a few moments I felt very tired. I tried to ask Rachel what she was talking about. Rachel said she would see me later and I fell asleep.

When I woke up I was in another room. I was sore across my chest, face and throat hurt and felt a little fuzzy. A nurse came over and told me I was doing great and Carrie and Rachel would be in just a moment. She gave me a few ice chips and told my to just suck on them. I tried to talk but all I could manage was raspy sound. The nurse told me not to and handed me a note pad. I could see some bandages on my face. I felt them across my nose and chest. It seemed my chest was larger too. I tried to sit up, but was so dizzy I gave up.

A few minutes later Carrie and Rachel came in. Carrie touched my sore face and chest lightly and began to explain. Debbie everything went great. You will be very happy with what I did. It will take a few days for the swelling to go down. The bruising will last a couple of weeks also. Afterwards you will look lovely.

I scribble that my throat hurt and wanted to know why. Carrie smiled Your throat will hurt for a few days. I need to warn you. No solid food for a week and no talking for two weeks. Next week you can eat jello or pudding or oatmeal. You know anything like that. That didn't answer my question. I was still too tired to argue and decided to let it go. About an hour later Rachel helped me to my feet and back home into bed. I felt different as if I had more upper body weight. I figured it was just the effect of being knocked out and drifted off in my own bed.

The next morning I went to shower. I went into the bathroom and noticed my chest was tightly wrapped and looked larger. My face had bandages across it and I was sporting two black eyes. My throat was scratchy and sore. Rachel was down stairs in the kitchen so I went down to get some answers. She was reading the paper when I walked in. Good morning Sweetie. You look a bit more alive than yesterday. How do you feel? I tried to talk and remembered what Carrie told me. I saw a pen and paper and wrote my questions.

What happen? What is wrong with my voice? Why do I look like I have bigger boobs? What is this with my face? I handed the pad to Carrie. She looked it over and thought for a moment before answering. Well you had surgery. You now have the breast you wanted. Granted I wasn't sure I liked the idea of you having DD's and me only D's. I figured it was your decision so I stuck with it. I am sure you remember telling me that. I thought for a bit then nodded. I had said that the first time I realized I was developing breasts. As to your nose, Carrie and I agreed you needed one a little more fitting a woman. You also will soon have a nice female voice. I just stood there. Look Debbie in just the few months you have become a very attractive woman. You have joined the ranks of the fairer sex. I just improved your look. Give it some time when the bandages are off your will see.

A couple weeks later the bruising and swelling were gone. Rachel and Carrie were right. I was very attractive. I had to admit I was impressed at the work that Carrie did. I also noticed that even more men were paying attention to me. Rachel said that her friends would be over and would be bringing others.

That afternoon the girls started to come over. As usual I helped then all get ready. I noticed a few men go down to the room in the basement where we watched TV and movies. I was dressed in a short skin-tight skirt that barely covered my ass. I had on red crotch less panties and a red bra that had holes for my nipples. My white top was so tight and low cut my tits nearly burst out of it. I had a red garter and seemed stockings with black 6" heels that buckled around the ankle. My makeup was thick bright red lips and dark eyes. I had blue eye shadow and long false eyelashes. I looked every bit a slut. Rachel had even lubed my ass before everyone arrived. After I got them all ready I came out to the Living Room. They all had robes on covering them so no one could see what they were wearing and how much those outfits showed. Rachel took my hand and led me downstairs. I noticed everyone else follow us down to the other room.

When I entered the room I noticed about eight guys in there. All rather good looking and well built. Rachel led me to the middle of the room. Gentlemen allow me to introduce you to Debbie. As you know Debbie is in transition. She recently had some surgery and has made a full recovery. I couldn't believe what I was hearing. Her was Rachel, my wife who had planned all the things I had been through now telling a group of strange men my story. Debbie has learned the finer arts of being a woman. As much as I, and these ladies can do there are things we can't. That is why Debbie needs your assistance. Debbie needs to know what it is like to be fulfilled as a woman. To have a man show her how to respond to his needs. Debbie needs to learn how to give herself to a man. She needs to know what it feels like to bring pleasure to a man. The kind only a woman can give. She needs to taste what a man has to offer, to feel the warmth as he fills her with his seed. Rachel was expecting me to be these guys sex toy. I was shocked that my wife was going to do this. Just then they led me into the hall. Debbie, you will please them. Every woman has done this. It is what women do. If you want to join use again you will do it. There is no way you can experience the joy we share without this. Now do what every woman does naturally. With that she pushed back into the room.

All the men were naked their cocks at the ready. The first guy had me kneel down and take his 9" cock in my mouth. I wrapped my lips around it a started to go down on him. The time I had spent sucking on the dildo had helped. I easily took his entire length and began to slowly bob my face on his tool. I found the smell of his crotch inviting. I was feeling an ache in me as I sucked his cock and balls. I realized that this was easier than I thought. I soon noticed I was cooing as I sucked the shaft in my mouth. As he slowly sawed it in and out of my mouth I ran my tongue along the sensitive underside. The more he did it the more into it I got. Then with a deep thrust into my mouth he let loose his load. I could feel his cock shoot the warm thick cream into my mouth. Wave after wave came out. He pulled back so that I could swallow his thick cream. It was salty yet sweet, much nicer than I ever thought. I eagerly down the fluid and sucked him clean.

When he was done the next guy bent me over so that I was now on my hands and knees. The short skirt was easy to move and give access to my crotch less panties. I could feel his pole at the opening of my love tunnel. With a quick push he was in. Then he proceeded to push until I could feel his balls against me. He held it there for a moment then pulled back so that only the head of his cock was still in me. Then he began to fuck me. Slowly at first, but he soon began to do it harder. The more he plowed his tool in me the more I moaned and begged for more. Harder and deeper he rammed me like a jackhammer. He was holding my hips as he buried his cock into me. I was meeting each thrust with one of my own. I was rocking in motion to his drives. Then with a couple deep drives he came. I could feel his cum filling me, the warmth of it shooting deep inside me. I squeezed to hold his rod in me. I shuddered and when he with drew another replaced his cock in me and one in my mouth.

It was incredible. I now knew what Rachel meant. I was enjoying the fucking and sucking. After they had all had me I was told to strip. I took off my top and skirt. Then one of them helped me with my bra. I was left with panties, garter, stockings and heels. I went to get them drinks and soon was given the chance to service their cocks again. I was there for several hours. As time went on I nearly begged to suck then and have them fuck me.

After they left I went to clean up. I was covered in cum and smelled of sex. I was overcome with the new joy I felt at being used by them. Rachel met me in the kitchen. She was wearing a bra and panties and waved good-bye to them as they left. As we headed up Rachel directed me to the front room. After the girls and I got done we moved your stuff in here. We figured after today you would need your own room.

My room was as large as the Master bedroom. It had its own bath and was next to the room I used to work from. I didn't mind too much and went to clean up. As I showered I went over all that I had just experienced. Rachel was right, I learned so much from today. After I showered I dressed and came back down Rachel was sitting in the chair.

Well, how did it go? Did you enjoy yourself? What did you do? How did it feel? I told her everything. I was a little uneasy telling my wife about what had happened. I tried not to tell her just how much I enjoyed it and how complete I felt as I was taking these guys cocks in me. Rachel smiled and we hugged. I am so glad for you. I knew you would be happy. I have to be going, don't wait up. She kissed me and left.

I watched her drive away and went back to my new room and feel asleep dreaming about the new joy I had found.

The next morning I woke to the sound of Rachel moaning and the bed moving in the other room. I walked slowly down the room and noticed that Rachel had a man in bed with her. I couldn't believe it. My wife was screwing a guy in our bed. Rachel looked at me and whispered into her lover's ear. I quickly darted back to my room. Rachel came in a moment later. What are you doing Debbie? I looked at her and wanted to know what she was doing. Who was that and what was going on? Rachel looked at me and pulled open my robe. You at you, you are a woman now. You found out what a woman wants, what a woman needs. You can't give it to me. You are worthless as a man. I know you not only enjoyed yesterday, you wanted even more. I could tell by talking to you that you would have spent the night with at least one of them too. I need a good fuck. I like to suck cock, fuck and take cum just as much as you do. With that she went do to her room. She was right. I had made the turn. I was a woman. I had found the joy of men and she wanted the same thing. I heard them again and imagined myself with a man. It wasn't long before I heard Rachel calling me. I went down to her room.

There in bed was this incredible man. Debbie, come and eat me out. Let's us give Derek a real show. I climbed between her legs and began to suck on her pussy. Debbie, eat my pussy. Taste the cum of this stud and my juices. She was moaning and squirming as I made her orgasm. Then she pulled me up. Debbie that was great. I think Derek liked what he saw. I noticed that his 10" cock was hard and ready. Go ahead suck that incredible cock. Without a second thought I wrapped my mouth around his pole. It was huge. I had a hard time getting my mouth down his cock. I sucked his cock and he soon filled my mouth with juices. I downed the sweet juice, not letting a drop go. He lay back and Rachel and I left the room. Derek went to shower and we went down the hall.

You know he has a brother. He said his brother's cock is even bigger. Debbie I know you are woman. You sucked his cock like it was a treasure. I smiled at Rachel and started to talk. No, please let me finish. I still love you, but you are not Robert anymore. You have become Debbie. There is no way you could go back if you wanted. She was right. No matter what I wanted to be Debbie. I wanted to have my own pussy for a stud like Derek to fuck. Rachel and I changed into just a thong and went back into the room. Derek was just getting out of the shower and his cock sprang to life as soon as he saw us.

Derek, Debbie and I want you to have a little fun. Take us both. I want Debbie to enjoy you too. Derek just smiled and took my hand. I lay on the bed and he pulled down my panties. He paused a moment when he saw the last remnants of Robert. Debbie has a great ass. She is a terrific fuck, so I have heard. Rachel said in his ear. With that he lifted my legs and entered me canal. Rachel lowered her pussy on my face and he began to suck her tits as he fucked me. Rachel had several orgasms while she rode my face. When Derek let loose his load I nearly fainted. I could feel he cock swell then he pumped what seemed like gallons of cum into me. I wrapped my legs around his waist and shuddered as he filled me with the juices.

Afterwards I went to shower and dress. I was washing off the cum dripping down my thighs. All I could think about was how wonderful it would be to have a pussy like Rachel. She was right I wasn't a man I was a woman and I wanted to finish what she had started. I wanted to have my own pussy. After I got dressed I called Carrie and arranged for an appointment.

Carrie told me what was involved in doing an SRS. She said she could and would but it would require bed rest and no sex for a while. I accepted the terms. I figured a little time in exchange for a complete body was worth it. I wanted, no needed to do this. I needed to become Debbie completely.

When I got home Rachel was gone. I figured she was with Derek and his incredible cock. She left a note and told me to be dressed for a date. She wrote he would be by at about 7:30. I went up stairs to my room to look for something to wear.

After a long soak in a bubble bath I wrapped a towel around my head. I admired myself in the mirror and dreamed of the day that I would soon have a pussy between my legs instead of the limp meat there now. I picked out a sheer white thong and matching bra. It was my favorite. When ever I wore a loose top the light material of the bra supported my tits but allowed them to move. I could see the looks in guy's eyes as they saw my tits bounce around. I then found nude stocking that did not need a garter to hold them up. I chose a short dark blue skirt and a yellow top that was just sheer enough to show the outline of my bra. Then a pair of 5" navy blue heels finished the look. I was just touching up my make up when the doorbell rang.

I opened it and met Derek's brother Brian. He was over 6 feet tall, dark blond hair and blue eyes. He was dressed in slacks and a shirt the barely covered his enormous body. I showed him in and nearly jumped him right there. I collected my things and went out with him.

The date was nice. It was simple and comfortable. I felt totally at ease with Brian. When we got home I asked him in.

There we were in the front room kissing. I had my arms around his neck and I could feel him rubbing my ass. His cock was getting hard and I decided I needed to see if it was true about him being bigger than his brother. I led him to my room and began to undress him. I was down to just my thong when I knelt down and pulled down his shorts. It was true. His cock was massive. I knew that there was no way I could take in all in me. If he fucked me I knew I would split right open. I did my best to suck his cock. I got nearly all of it in. No matter how I tried I just couldn't take it all. As my face fucked his pole he held my head. He swelled then let loose his load. His thick seed pulsed out and I did all I could to get it down. Brian pulled back leaving only the head of his monster in my mouth so I could finish him off.

When I licked him clean he looked at me Debbie that was incredible. No woman was ever able to take as much as you did. I thought I was going to pass out when I came. Derek was right you are the best. We climbed into bed and Brian took off my panties and soon we were at it again. Brian had me on my back as he pushed his massive cock into my fuck hole. I could feel it stretching more than ever as he slid it in. Soon he had it all the way in. He held it there and was breathing in short quick breaths. After only a few short strokes he filled my passage with cum. He drilled me once more before we fell asleep. The next morning Brian's cock was hard and ready. I climbed on top and lowered myself on his stiff pole and rode him till he filled me again. I lay in bed just feeling the warmth of his body for a while. When I heard Brian step into the shower I decided to join him.

I took the soap and washed his body. I felt every ripple of his firm muscles and stroked his cock until it was hard again. I then went down on him. I was sucking his tool as the warm water fell on us. He came again filling me with his seed. We got out and I helped him dress. I slipped on a robe and kissed him god-bye at the door. Went back up and showered after he left and was just picking out things to wear when Rachel walked in.

Carrie called while you were in the shower and said something about your date being in three weeks. I took the note and stuck it in my date book so I could write it down later. I then went back to get a bra and panties. What date? I pulled on my panties and slipped the straps of my bra up before I answered. I told Rachel I was going to finish the process. I told her like she told me. I was Debbie. I was a woman and not a man. I told her that I might as well get the body I had. I was ready and wanted a pussy.

Rachel smiled and hugged me. My sister, how wonderful. We decided that we needed to make a few changes. That day we drew up our divorce. It was simple; when I left I got a set sum of money in exchange for everything. We now had separate accounts and one for the house. I had my paper work done to read Debra Lynn Messer female.

Brian and I dated and I arranged for a leave of absence from work. I needed some time to recover from my surgery. Brian and Rachel were with me when I went in for the SRS. Brian kissed me as the put me under and promised to be there when I woke up.

I slowly came to in another room. I was aware of a dull pain in my crotch. Brain came over and took my hand. They said it went perfect. In a few days you can go home. I smiled as Brian kissed me softly. I was pretty foggy at the moment and didn't say much. I really just wanted to get back to sleep. A nurse came to check on me. She said I would be really sore and had pain medication in my IV and all I needed to do was push the button if it really hurt. I must have fallen asleep because when I opened my eyes again Carrie was next to me.

Everything went wonderfully Debbie. Soon you will have your dream. It took a little work, but I wanted to get it perfect. She explained everything I needed to do and what to expect. She explained the healing process and the time line. As much as I wanted to take note of what she said I was still too fuzzy to process it all. I could hardly remember what her last sentence was much less the detail stuff.

When the day came that I was cleared to do what I wanted I was thrilled. Brian had been wonderful. He had helped me out and looked after me the whole time. So after I left the office I bought a bottle of champagne and attached a note card. I then stopped by his office to give it to him. After he saw the note his eyes lit up. You mean…I mean… I finally just said yes. That weekend Brian and I slipped away and I treated him to my new pussy. Or maybe I should say my new pussy was treated to his incredible cock. Either way it was wonderful.

We are now engaged and I am planning on moving out soon. Brian and I are looking for a place. Soon I will enter the next stage of my life. I will become Brian's wife. I always wanted to use that term about myself. I can't wait till I get introduced as a wife, a woman devoted to a man.




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