Caught and Transformed                by: Patricia Anne Anderson

 

Part One

As I sit her in my nice clothes I reflect on how all this began. I was a normal male in every sense save one. I liked to Cross Dress and my wife of 5 years was going to make sure that I could do it anytime I wanted to. The unfortunate thing for me is she wanted me to be female all the time. So here I sit writing this story at her request, no at her insistence.

It was 4 years ago when my wife walked in the house after work and there I was all dressed up in some of her clothes. She just looked at me and didn’t say a thing. I was then very worried about what she would say. I quickly went in and took off all the clothes and went to the living room where she was. There she started asking me questions.

"When did all this start dear?"

"Well it was a long time ago when I was about 5, I got interested in my mothers and sisters clothes and my sister even dressed me up sometimes."

"Well, I was worried because I thought you had another woman."

"No honey, you know I love you."

"Yes you do don’t you."

We sat and talked for hours on what was to transpire. She told me that from this time on she wanted me dressed only as a woman while at home. I readily agreed and my training began. Little did I know the ramifications that this would cause.

The next morning a Saturday she got me up early and told me to go to the bathroom. There she had several items that she put in a bath. Then she spread a cream all over my body and told me to wait about 15 min. When the 15 min was up she told me to step into the tub and the bubble bath she had run. I got into the tub and a few min after I got in all the hair on my body fell off. She then told me to stand up and she took a razor and shaved my pubic area into a little triangle patch.

When the bath was over she told me to towel off and told me to go to the bedroom and wait. She came in a few min later and sat me at her vanity. She put rollers in my long hair and setting gel. Then she told me to go sit on the bed and wait for her.

I sat there wondering what she had planned. She came back with several items including some surgical tape. She had me lay on the bed with my legs in the air and she expertly pushed my cock and balls up inside my body. Then she took the tape and fashioned a make shift vagina out of the skin from the empty ball sack. I looked and saw what appeared to be a vagina.

Then she took some breast forms and glued them to my chest. I now had two tits and they looked rather good. She smiled at me and said this is only temporary. I did not know what was talking about but I would find out very soon. She continued doing what she was doing and told me to stand up. As I stood up she wrapped a corset around me and told me to lift my arms in the air. When I did that she began to pull the laces of the corset tighter and tighter. It was getting to the point I couldn’t breath but she kept pulling the laces till my waist was at a size 24 inches. I could hardly breath and she smiled at me.

She then picked up a pair of nylons and rolled them up my legs and attached them to the garters on the bottom of the corset. Then she picked up a pair of red silk panties and slid them up into place around my waist. Next came the matching red satin bra trimmed in black lace. She put my arms through the straps and attached it in the back.

It was all coming together and I didn’t know where it was all going. She picked up the blue silk maids dress and had me step into it. It was short and only came down below the tops of my nylons. Then she picked up the red crinoline petticoats and had me step into them. She pulled them up around my waist and smoothed down the dress. The sleeves of the dress were fluffy and had lace boarders. The bodice of the outfit swung low in front and the cleavage that showed was rather stunning. Then she sat me down and had me slip into a pair of high heeled shoes. The heels must have been 7" or so and when she attached the ankle strap and told me to stand up I had a hard time walking at first. She had me sashay around the room to get used to them.

She again took me to her vanity and began to apply foundation and make up. It didn’t take her long when she took my hair down I almost fainted. There was the prettiest woman sitting there. It was surprising because I never expected my wife to be doing this to me.

"Now, that is complete, your training will begin."

"What do you mean, my training?"

"You will see, you are going to be my house maid whenever you aren’t at work you will be dressed in this outfit. You will have to do all the chores including the laundry, cleaning the house and the cooking, and you better do it right."

That sort of scared me but I wasn’t in a position to argue.

"One more thing, you will do as you are told or these will be distributed among your friends and co. workers."

She held up some Polaroid’s that she had taken of me in various stages of transformation. I was caught and trapped into what I did not know. She told me she had some errands to run and that I had better have the house spotless when she got home. I looked at her and didn’t know weather to laugh or cry. She kissed me on the cheek and picked up her purse and left.

I didn’t know where to start so I started in the living room dusting and vacuuming and cleaning. Then I went in the kitchen and did the dishes. I went to the laundry and started to do the laundry which was something I never did. I had to more or less guess how to do it but managed. My wife was gone for several hours and when I was in the middle of folding the clothes she came home.

She called to me and I went into the living room. She had a friend with her and I immediately started to blush. Her friends name was Kathy and she was one beautiful woman which I had met before. She took one look at me and smiled.

"Hmmmmmm, Very Pretty, what is her name?"

"Oh, I haven’t figured that out yet, what do you think Kathy?"

"Well, Samantha seems like a pretty name for her."

"Then Samantha it is," she smiled.

My wife was now thoroughly into this whole thing and I was relay scared. I didn’t know just how far she was going to take this. I would find out that night as she an Kathy had planned a party and I was to be the maid. I was told that I would serve the guests any way they wanted and that I would wear the French Maids uniform I had on.

"Now run along Samantha, I need you to get prepared for tonight."

Both woman laughed as I went into the kitchen to prepare for the party they were hosting. Dissipate all that was going on she worked with a smile on her face and she whistled as she worked preparing all sorts of snacks and party favors. This was all so new to her but she was prepared for just about any thing. Samantha would find out that this party would be the beginning of the end of her male personality.

 

Part Two (The Party)

It was getting late and Samantha had set out all the things she needed for the party including stocking the bar. She was in the middle of setting up the snacks and things when Diane and Kathy returned. She finished what she was doing and greeted them as they came in.

"Hello madam would you’d you like me to take your coat for you?"

"Why of course dear," Said Kathy with a smile.

"You can take mine also Samantha, you know where to put it."

"Would you like a drink ladies?" she asked.

"Certainly, you know what I like Samantha." Said Diane.

"Make mine a vodka gimlet please." said Kathy.

I curtsied and went to the bar to fix the drinks. When I gave them their drinks there was a knock on the door. I went to answer it and there were two couples there. The men were very handsome and very tall about 6’4" tall and very muscular. They towered over me as if I were a dwarf. But then I was only 5’6" tall anyway. My wife Diane was as tall as me if not a bit taller. The woman with these men were very beautiful and very tall as well. They looked like models or something. I took their coats and things and went to hang them up. The men both had a funny smile as I took their coats from them. One of the men even patted me on the behind as I walked away. The woman just giggled as they went over to where Diane and Kathy were sitting.

"Where is your date for tonight Kathy?"asked one of the woman.

"Oh he will be here a little later Melinda," said Kathy.

"And what about you Diane?" asked her friend Andrea.

"Oh he will be here soon." said Diane with a smile.

My heart sank as I heard her say this. I couldn’t imagine my wife out with another man and I wanted to cry. I fixed the two woman and their dates some drinks and went back to serving the snacks. Of course when I bent over to serve them my skirt was so short that my pettipanties would show and the men would pinch me on the rear. They were all having conversations between themselves and pointing at me. About half hour later there was a knock on the door and I went to answer it. There were two very handsome men standing there and I guessed they were Diane and Kathy’s dates. They both smiled at me knowingly as I took their coats. Both Diane and Kathy came to them and gave each one a big hug and very affectionate kiss. My heart started to break when I saw this and the tears started. I composed myself as I went to the kitchen.

They were all having the time of their lives and I was getting sadder and sadder I wanted to run and hide. What was my wife doing to me and why was she doing this to me now of all times with our anniversary a week away. I was sashaying around in my maids uniform doing what any maid would do. Then one of the men came over to me and took me in his arms and kissed me hard on the mouth. I tried to pull back but remembered what my wife had said that I had to do what ever they wanted. I let him kiss me and for some reason I started to respond.

"So, you are Diane’s sissy husband are you, we are going to have some fun with you tonight my dear. By the way you are very pretty and if I didn’t know you were a male I would swear you were a real female."

I blushed and thanked him dissipate myself and he patted me on the rear. It was about fifteen minutes later when I was taken by the hand to the center of the room and my wife said very loud.

"Ladies and gentlemen, it is showtime, Samantha please come here."

I didn’t know what was happening but I heard four zippers coming down at the same time. I was blindfolded and when it was taken off there were all four men with their cocks in their hands standing right in front of me. God I had never seen cocks that big in my life my own tool was small in comparison. The first man, his name was wayne stepped up and pressed his cock to my lips. I didn’t want to open them and my wife looked at me sternly and I did as I was told. I opened my mouth and he pushed that monster in and right to the back of my throat.

I almost gagged and wanted to throw up. Damn could this really be happening to me I was lost. I licked the shaft as best I could and Wayne held my head as he sawed in and out of my mouth. It was as if a gigantic log was being forced down my throat. I did my best as he continued to fuck my mouth. It wasn’t long and he stiffened in my mouth, I could feel the cum racing up his shaft and soon I had my first taste of male cum. It splashed against the back of my mouth and down my throat. It tasted salty but was sweet at the same time. It was silky and slimy as it went down my throat. Dissipate my efforts to swallow it all some of it escaped and trickled out the corner of my mouth. He seemed to go on forever as blast after blast of his cum went down my throat. Finally he was done and as he went limp I cleaned him off and he gave me a peck in the cheek.

"Thank you babe, that was the best Blow job I have ever had."

It wasn’t over and before long I was spread-eagle over the coffee table with my wrists secured to the legs. My panties were taken down around my knees and some one was spreading something very wet on my asshole. I had to figure out what was going on and wanted to run but couldn’t. Then this man started to push his cock into my small asshole and it hurt really bad. I screamed as he forced his way in past my spincer muscle and deep inside me.

"Don’t worry babe, you will be able to take all my 10 inches and it will feel good soon."

As he said I did take all of it right down to his balls. As he began to fuck me slowly his heavy balls were slapping up against my ass cheeks. He got more leverage as he grabbed my waist and pulled me back at him as he fucked me for the first time.

"Oh yes, that is soooooo good you little sissy, take all my cock, feel it deep inside you, oh yes, you are so tight."

Dissipate my self as he fucked me I started to get a feeling down in my gut and my own small cock was trying to grow. But pushed up inside me like it was it was impossible but for some reason I started to shake and as I did I felt myself cuming. Was I having an orgasm, is this what a woman felt like. Waves of passion swept over me as I felt myself cuming.

"Ah yes, I am going to cum, take it all sissy." screamed the man.

I wanted to pull away but his cock was filling me to capacity and he held me tight as he fucked my virgin asshole.

"Yess, here it comes baby, I am going to cum."

The man pushed in really hard and I felt him grow bigger and stiffer and then I felt his cum spiriting deep in my bowls. It was as if I were getting an enema there was so much of it and when he was done and he pulled out the cum started running down my legs. The tears were cascading down my cheeks and I wanted to run away. The woman cheered as he pulled out of my ass. The men applauded his efforts and I was crying. This wasn’t all of my humiliation though. The next thing I knew I had a cock in my mouth and another cock up my ass.

This seemed to go on forever as I was fucked and I sucked cocks for what seemed like hours. When they released me I was sore and upset. Diane offered for any one of the men to take me to bed that night. Wayne was the first to reply.

"I will take her to bed tonight," he said with a smile.

I was crying and upset so Diane and Kathy said they would clean up as Wayne took my hand and led me off to the guest room. When we got there he told me that this had all been planned.

"You are a very pretty woman Samantha and I for one am sorry you had to go through this tonight."

He took me in his arms as he started to undress me. He was gentle dissipate his size and I found myself accepting him as any woman would. But what of my wife? What did she have in store for me? what was my future. I let Wayne fuck me one more time and I fell asleep with his hard cock buried inside me.

 

Part Three (The Journey Begins)

Time seemed to be caught in a bottle as every day when I came home from work I had to be dressed as a maid and I had to do the house work and the cooking. I was always dressed in my maids uniform. My wife Diane had started to give me some special vitamins as she call them. I had to take two in the morning two at lunch and two at dinner. In about 3 months I noticed that my nipples were getting tender and they seemed to be getting bigger. There were visible mounds now growing on my chest and they were also very tender.

One day when I was home alone there was a knock on the door. I went to answer it and there was Wayne. I let him in because I knew him and I knew he would not hurt me in any way.

"Hello babe, how are you today?" he asked. "

"I am just fine hon." I said as I blushed.

No one had ever called me babe before and I blushed as he took my hand. He handed me something and said it was something special. He took my hand and placed a small ring on it. This surprised me and I almost fell over.

"That is a friendship ring I just gave you Babe, do you like it?"

"Why of course Wayne, thank you."

"Diane said I was to come and keep you company because she will be out for a while, do you have all your work done?"

"Why yes I do, why do you ask?"

"Well because Diane said I could take you out to dinner if I wanted to."

"I would like that Wayne, thank you."

I was surprised that I said that and that I really wanted to go out with a man but at this point my thoughts were becoming more and more female. What was my wife doing to me?, why did I feel this way? I went to my room and took off my maid outfit and but on my best dress. It was a red dress that Diane had gotten me so we could go shopping.

I was getting a rather extensive wardrobe now of female clothing including panties and bras and shoes. I was getting rather good at putting on my make up but I still didn’t have pierced ears. That is something that would change in the not to distant future.

When I was all ready I went to the living room and there was Wayne with a big smile on his face. He whistled at me as he took my hand. We left the house and by now I was getting used to being out dressed as a female. As a matter of fact I looked and acted more female than male. I would find out much later that the vitamins I was taking were in fact female hormones. They were beginning to change me in more ways than one. My feelings were becoming more and more that of a woman and I must say I rather liked it.

As we left the house Wayne kissed me hard on the lips and I opened my mouth and let him slip his tongue in. I could tell that he was getting turned on by the way he was kissing me. We got in the car and he being the gentleman opened the door for me. I was flattered because no one had ever paid this much attention to me as a man. What my wife was doing was making me feel better about myself.

We drove to a little restaurant where Diane and I had gone on many occasions. I was beginning to like this attention. Dinner was very good and the waiter asked if I had ever been there before because I looked familiar. I of course told him no, I knew this waiter because Diane and I had been here many times especially on our anniversary.

All during dinner Wayne was putting his hand on my leg and smiling. I knew he was getting very excited because I noticed the bulge in his pants. He reached over and took my hand and asked me to dance. I of course accepted and while on the dance floor he held me really close and had his hand on my rear. I knew what he was after as Diane and I had done this same thing many times. I would have to admit that I liked what he was doing. What was wrong with me, why was I having these feelings?

The next two or three hours were the most exciting I had had in a long time even with Diane. I can’t remember when I had been more happy. After dinner Wayne took me to a place that most of the teenagers went to neck. I must admit I was excited and when he started to caress me I was putty in his hands. Why was I feeling this way?

 "Wayne, you know who and what I am, why are you treating me this way?"

"Well quite frankly Samantha, Diane has found herself another man and you are so much like a woman. I love being with you and dispite the fact that you were born a male doesn’t mean that deep inside you aren’t female, that is the way I feel anyway."

Wayne had a point, I was begining to feel more like a woman every day. I was even looking more and more feminine. By now I had my own set of twin mounds on my chest that would rival any woman’s. Wayne started to unbutton my blouse and I just let him have his way with me. The next thing i knew I was reaching for his fly and I took out his huge cock and started to jerk him off. The more I massaged it the more he kissed and sucked on my nipples. It felt so good and I wanted him to do it. I lowered my head and started to kiss the tip of his member and I could taste the precum that was there. I kissed and licked the entire length of it from the base to the tip. I concentrated on the very sensitive underside and it was getting harder in my hand. Then I opened my mouth and took in the tip of it. I loveingly caresed and sucked the tip and Wayne was going crazy.

I started to take the rest of his 10 inch member in my mouth and it felt so natural as if I was meant to be doing this. Wayne’s head went back and he moaned as i continued to suck on his cock. He put his hands on my head and pushed gently and the tip of his cock went into my throat. He was now gently fucking my mouth and I was doing my best to take it all.

"Yessssssss, baby, that is soooooooo good, suck my cock."

I continued to suck his cock and before I knew it he got stiffer and I could feel the cum shoot into the back of my mouth. I held just the head of his cock in my mouth as he ejaculated spilling a huge amount of his seed onto my tongue.

"Yes, sweet baby, that is it, I am cumming, take it all, make me feel good."

I continued to suck him til he started to go soft in my mouth. The taste of his cum on my tounge was sweet. I loved the taste and the feel of it. When he was done I tenterly cleaned him off making sure I got every last drop. He took me in his arms and kissed me and I melted like putty.

"You are so beutiful sweetheart and I love you."

"I love you too Wayne."

I couldn’t believe I just said what I did, but I did. Who am I was the question in my mind? What next, how far would I go? Where was I going to anyway. The visions that flashed in my mind were very tremendous. Was I in love with this handsome man?

How could I be, after all I was still technicaly a male. I had been raised to believe that what I was doing was wrong. What had Diane and Kathy done to me? Am I not a male? Or am I? On the way back home Wayne held my hand and he would every now and then look at me and smile. When we got home the lights were still out in the house and Wayne asked if he could come in.

"May I come in sweetheart?" he asked with a smile.

"Of course you may hon." I said.

As we sat on the couch hugging and kissing Diane came in and she was with a another man. I sort of expected this because for the last 3 months her and I had not touched each other. I guess this was a signal that things were changing. She smiled as she walked up to us and smiled at me.

"Well hello Samantha, I would like you to meet Charles, he is a man that I work with at the office."

"Hello Charles, I have met you haven’t I?

"Yes you have Sammie, remember, I was the guy who was in the work station behind you."

He smiled as he said that and flashed me a knowing smile. He and I were friends and he always had an eye for Diane. He was at least a foot taller than me and very muscular. I started to cry as I remembered and I got up and went to my room. Wayne was close behind me.

"What is the matter babe?" he asked as he came in my room.

"Nothing hon.’ I said wiping the tears from my eyes.

I always knew that something like this would happen but I never expected it to happen in this way. Wayne took me in his arms and wiped the tears and held me close to him. Then he slowly started to undress me. I let him have his way because I could hear Charles and Diane in the other room making love. Wayne looked into my green eyes and smiled. It looked like he had a tear in his eye also.

"Look baby, I know who you are, I know what you are and it makes no difference to me. I love you and I think I have since the first night of that party."

I couldn’t believe what I was hearing. This man so handsome and in love with a Transvestite, me. I let Wayne have his way as he took off my panties and bra and slowly undressed himself. The bulge in his shorts told me what he wanted and I laid back on the bed and put my arms out to him. He came to me and I stripped off his shorts and took his cock in my mouth. He needed no encouragement as he took his time letting me do to him what came natural for any woman. When he was hard enough he rolled me over on my stomach and lifted my behind where he could enter me. He did so slowly and I swooned as he pushed all the way in. He was not in a hurry and he took his time slowly fucking me. When his cock rubbed my prostrate I got a feeling deep inside and I was actually experiencing an orgasm. But it was internal not the kind that a male would have.

We went at it for nearly an hour and I had several orgasms just like a woman would have. What was happening to me? Who am I? what have I become? I was feeling so good and all at the hands of another male. But then I guess I was now more female than male anyway. Had the hormones done this to me? Where was all this leading?

I let him fuck me as deep as he could and I was enjoying it. At that very instant Samuel Jester had disappeared. He would no longer be the male he was. Wayne started to push in faster and faster and I could feel him grow inside me and I knew what was coming. I heard him moan and then push in as far as he could and I felt his manly fluid going deep inside me and at the same time I had another mind bending orgasm. He held himself in me for a long time and when he finally pulled his limp cock from the confines of my ass pussy he rolled me over and took me in his arms and kissed me.

"Samantha, will you marry me? He asked.

I didn’t know what to say, I was lost in ecstasy,. Does every woman feel this way? how could I refuse him, I was in love.

"Yes Wayne, I will marry you."

His eyes lit up like candles as he kissed me once again. We fell asleep in each others arms. The next morning when we woke up I put on my robe and went to the kitchen where Diane and Charles were already having coffee. I went to start breakfast and Diane told me no, it would be her treat. Wayne came in shortly afterwards and was smiling.

"What are you grinning like a Cheshire Cat for?" asked Diane.

"Well, I asked Samantha to marry me." he said

"And her reply?" asked Diane and Charles together.

"Well she said yes."

"Oh my God!" said Diane.

"Congratulations Wayne!" said Charles.

I looked over at Diane and she looked stunned. I smiled at her and she just stared at me. I was smiling and Charles winked at me.

"Well what a revelation, Samantha are you sure you want this.?"

"Yes Diane, I love you but as you can see I am no longer the man you married thanks to you and Kathy."

There was allot of talking after that and allot was discussed. There would be allot of changes in the year that would follow. Diane and Samuel Jester got a very quiet divorce and Samuel changed his name permanently to Samantha Jester. The divorce didn’t even split up the estate as both Samantha and Diane lived together as sisters. They were planning a double wedding. Diane and Charles were getting married as well. Samantha had gone to a clinic in Mexico and had breast augmentation done which gave her natural 38C breasts. She was permanently on female hormones and was filling out nicely as her body changed from that of a demure small man to a ravishing female. Her surgery was scheduled for the following summer after her and Wayne were to be married. She was never happier in her life.

The Beginning not the end.

 

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