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Reorientation

by Jennifer White

  

I felt so trapped! I was married to Jim, and we had been happy at first. But he soon stopped treating me like he did when we first got married. And he was so manipulative! He didn't put the money in 'our' account; he had it where only he had control of it. And I suspected that he had a lot more money hidden somewhere, perhaps in overseas accounts I couldn't touch.

I couldn't leave him; I had devoted my life to him, but had nothing. I'd be starting again as a 45 year old woman, with no money, no degree, no skills, other than those of a housewife. I would end up working all my life, being poor, and being past the prime of my looks, little hope of finding someone again. And how could I trust another man after all I had been through with Jim?

No, I was stuck with him. But life was so empty for me! For example, we never had sex more than once a week, and even then he seemed almost disinterested in me. He must have been getting some one the side, perhaps when he went on those business trips. And he would never do what *I* wanted in bed. He'd never go down on me. No, only me on my back was what he would do. The missionary position again. Boring! But he was nonadventurous.

I rued signing that prenuptial agreement now. I hated my life, and I had no idea what to do. I wanted to leave him, but couldn't. And he didn't care about me. And I wasn't the type to cheat on him. Even as much as I hated everything, I couldn't do that.

It was only after reading a steamy romance novel (with a shocking twist), that a seed of an idea sprouted in my head. In this book, a woman much like myself was trapped in a bad relationship. To get out of it, she did something shocking: she turned her husband into a woman. I wondered if such a thing was possible in real life!

I couldn't get it out of my mind. Finally, I decided that I would give it a try. It took months of detailed planning. I read information on the internet! I read books! I bought supplies, carefully not spending more than a few dollars at a time, so he wouldn't get suspicious. Finally, after three months, my plan was ready, and I was set to begin. It was time to turn Jim into a woman.

* * *

 

The first step was very simple, really. He took vitamins every day. And he took pills at night. So I tricked him into taking an estrogen pill every day. I got a supply of them, and compared their shape and size to the dozen or so pills that he took. I of course did all the shopping for him, so it was easy to put a 'new' bottle of 'vitamins' on the shelf, with the vitamin B pills in the trash, replaced by estrogen pills. He never even noticed.

Then I started cooking with Soy milk, used soy protein, and other plants containing isoflavones, which are supposed to mimic estrogens. It wasn't definite that they had an effect, but every little bit helped, and I wanted to make sure. And soy is good for a woman's diet, so at least I would be benefiting from it.

I even replaced his Once Daily multivitamins with Once Daily for Women. It was symbolic mostly, but hey, the thought that he was taking women's pills was exciting for me. Soon, I would add birth control pills on the list of substances that he received. But not yet. It had to be gradual and slow, so that he didn't notice.

* * *

 

And for the first few weeks, there was no apparent effects or changes, at all. Nothing in terms of his behavior, or nothing physical. I had read that it would take time for the hormones to build up in his body, and only after they reached a certain level, would there be any effect.

So it was actually a matter of months before I thought I could see something. Perhaps just a little bit of a swelling in his chest? Perhaps around the areolas, his boobs were starting to bud. It was then that I replaced another pill for him. The male body has a trace amount of a chemical that converts testosterone to estrogen. That is why men have a trace of estrogen within them, even though they don't have ovaries like we do. By adding it to what he was ingesting, it would naturally increase his estrogen level, while decreasing his testosterone at the same time! Again, he didn't even notice that I had changed pills on him. All was going according to plan.

* * *

 

About a month after my latest addition to his diet, while we had sex, I reached up and started to pinch his nipples. It really turned him on, and he said that it was one of the best orgasms that he ever had. So the next time he wanted sex (a full week later), I did it again. And harder too. That plus the start of the swelling he was having, made him complain to me "My nipples really hurt. They're sore!"

"Oh poor baby" I said, sympathetically. "Let me get some cream to soothe them."

I got out a tube of cream, and rubbed it all over his breasts. Of course, it wasn't a soothing cream at all; it was 'breast cream', which was supposed to be guaranteed to make your boobs grow at least one extra size. Again, I had no idea if it would really work or not, but it couldn't hurt to try.

I also read an interesting article online: it turns out that some types of plastic can leech out a substance into food, which is very similar chemically to estrogen. If food is cooked in plastic, it can accelerate the leeching process. So of course: I started to cook our food in plastic whenever possible. I ended up melting a couple of Tupperware containers until I figured out when to stop the heating. But again, I figured that every little bit helped.

And in time, I was rewarded. Besides the small budding of the breasts I had noticed, his skin seemed to be softer to the touch. He didn't notice, but I did. He complained that some of his pants didn't fit him, because he was gaining weight in the thighs, although I thought his hips and butt looked just a little rounder. He was having trouble losing the weight too, because he felt weaker, and couldn't exercises as long as he used to before.

And speaking of rounder, in time I definitely saw his face starting to look rounder. It gave it a slightly different look. If this kept up, it would start to look more like a woman's face! The hormones were working their magic on him.

Not to mention that fact that by now, he had all but stopped having *any* interest in sex. The best thing for me, was that the woman on the side had to have dumped him, because he was staying at home a *lot* more now, and we seemed to have more money in the checking account too.

He stopped playing basketball with his buddies, since he couldn't keep up with them physically anymore. That made him stay at home even more. And without the excuse to hang out with them, he stopped going to the bar, and stopped seeing them in general.

I didn't know it was the fact that he had been dumped, an effect of the hormones, or the fact that he couldn't 'get it up' anymore, but he seemed depressed at times, and had become very passive. But that was perfect for me, it exactly fit my plans. Everything was ready to move into the next stage.

* * *

 

With Jim being passive now, he would respond to me so much better when I asked him to do something. I tested his limits a few times, and found that he was much more willing to do things than he ever had been before. When he did what I asked him to, I made sure to dote on him, treat him well, rub his shoulders, and all that. When he didn't, I gave him the cold shoulder.

I was the only friend he had now, and I think for the first time since we were married, he was actually concerned about *me*, and not wanting to lose me. I was so happy (other than the fact that we never made love anymore). But I had prepared for this tough stage of my plan, using a vibrator on myself almost every day to make myself come. It was wonderful, but not the same as you get from physical contact.

I waited until one Friday when he came home from work. I dressed in my most seductive clothes, had candles burning, flowers set in vases, dim lights, an open bottle of wine, and everything ready to put on a show for him. But he wasn't very interested, as I had expected.

"Jim, you don't love me anymore. You never make love to me. You act like you're not even interested in sex anymore!"

"Ruby, please, I'm going through a tough time."

"Why? What's wrong?"

"It...its that I can't get an erection anymore. I even bought some viagra, but it didn't help. Something is wrong with me."

"Its all in your mind. You just don't love me" I said, pretending to start to cry.

"No! I do love you! But something is wrong with me!" he pleaded.

I had him right where I wanted him.

"I've tried for years to get you to try something you call 'kinky' in bed, but you've always refused. I think that if you do really owe me a chance to try this, if you love me like you say you do."

"I do love you Ruby."

"Then prove it. Lets go upstairs, and show me that you do love me."

We went up the bedroom, where I had set up the bed with the silk sheets which we hadn't used since the first week back from our honeymoon. I had lacy shams on the pillows, and all sorts of little details (which I'm sure he missed), making it a really romantic setting.

I held my body close to him, so that he could feel my boobs poking him. I used to feel him get hard and push back into me, but not anymore. I had him slowly undress me, and I did it back to him. Soon, we were naked together on the bed.

"Such my nipple" I said, and he did it! For the first time, he actually did it! It felt lovely, and I was starting to get all wet inside. I massaged his little budding nipples gently and sensually, and I could tell that he was getting all stirred up inside, even if there was nothing happening between his legs.

"Please my love" I said, "just this once, go down on me. You know I've always wanted it. Do it! Now!"

I was amazed that he actually crawled to the edge of the bed, got on his knees, and went down on me! He used his tongue, and started to press it up near the top of my slit, where my special place was. Oh how wonderful it was! I had so many orgasms so quick, you would not believe it! And then I had a couple of really big ones.

I was shaking all over, trembling. I hadn't felt this wonderful in bed, *ever*. I finally got too tender, and had to push his head up to make him stop.

"Oh my god!" I said. "That was incredible!"

He just grinned at me.

"Now I'll do you" I said.

We traded spots, and I went down on him. But try as I might, there was no reaction from his genitals. No amount of stimulation would get him hard now. The female hormones were overrunning his system, and his male equipment no longer got the hormones it needed to function. He was no longer truly male. He was on his way to becoming a woman.

I went at him harder, and started to play with his nipples. His gasps told me that he was feeling *something*, but he still didn't get hard. After a while, he said he was too sore, and asked me to stop. I put some more of the 'soothing cream' on his nipples.

"What's the matter my love?" I said. "You were so wonderful to me in bed, but you just didn't respond to my touch like you used to."

"I tell you, there is something wrong with me!" he said.

"Perhaps its those tight pants you always wear" I said. "Here, wear this around the house tonight."

"A nightie? I can't wear that?"

"Why? Nobody will see you inside here. You'll find it very comfortable. Its very silky, and feels good against your skin. You say your chest is sore to the touch. This will help. And without being so tight on your crotch, perhaps that will help down there too."

Reluctantly, he agreed. He was now wearing his first piece or women's clothes. Soon, it would be the dominant selection in his wardrobe, if everything else kept going according to plan. I was afraid that he might go get a physical, and they would find the elevated levels of female hormones. But I knew him well. He was too proud, like many men are, to go and see a doctor. I had counted on it, and so far, he hadn't shown that he would act otherwise.

* * *

 

Now I upped Jim's dosages, and added the birth control pills. Well actually, not the pill. I had been bugging him for years to quit smoking. I brought him 'the patch', but it was the one for female birth control, not the one with nicotine in it! With his new passiveness, he was more accepting to try and quit. So he wore the patch! He thought it was making him stop smoke, but it was really there to slowly release female hormones into his bloodstream, and help turn him into a woman.

I would trick him from time to time into wearing my nightie. After a few times, he was used to it, and it didn't seem to bother him anymore. I made sure that when he wore the nightie, I treated him *so* well. When he didn't, I treated him less good than normal. He might not have noticed the difference consciously, but at least it had to do something to his subconscious. So that's when I tried the next trick I had up my sleeve.

He was in the bedroom with me, wearing the nightie. I was playing with some clothes on hangers.

"Oh Jim, would you be a dear?"

"What is it Ruby?" he asked. I was so nice to him when he was in the nightie, that he seemed more eager to please than when he wore his own clothes.

"I'm rehemming my skirt, and I need some help" I said. "Do you know how to measure it and pin it?"

"No..." he said.

"Then be a dear and put this on so I can hem it up" I said.

He put it on, and I started to pin it up. I took a step back.

"Oh dear, I can't tell how high I need it, unless I see it with the top too. Here, put this on."

I handed him the top, which he put on too. I took my time pinning up the hem, redoing it a couple of times.

"Turn around. Good. Now let me see you in profile. Yes. That looks very pretty."

Now he was wearing a pretty top, and a skirt.

"Look in the mirror" I said to him. He turned and looked in the full length mirror.

"I love the way yours skirt makes your legs look. And your top has some padding in the chest area, but it almost looks like you're starting to grow little breasts. I think that this isn't an accident. I think that this is what you wanted all along, isn't it?"

"What do you mean?" he asked.

"I mean that you seem to like wearing your nightie. You look pretty in a dress. Your boobs are starting to bud out. It looks like you're developing curves. You're not interested in sex with women anymore. I think that you *want* to be a woman yourself."

"No!" he said.

"Really? I ask you to put on a dress to help me out. A year ago, you would have run away. Now you did it, and I think you like it."

He looked down at the floor.

"Jim, look at me. This is important. Tell me what you're *feeling*. I need to know."

He just looked up to me with puppy dog eyes.

"Its okay dear. I won't be mad at you. I just want to help you."

I had read that high levels of female hormones could effect how a man felt inside. That it could even make their sexual attractions change. I was pleased with his answer.

"I feel mixed up" he said. "I don't know what I want. I don't know why I feel the way I do. Something in me has changed, but I don't know why."

"I love you" I said. "And I will support you, no matter what happens. Do you understand that?"

He nodded.

"Good. Now listen to me. Let's explore today. Let me make you a woman, just for today, and see if this is what you really want. I'll dress you up, I'll make you pretty. You can be a girl today, and nobody will care. We'll find out if this is what is really happening inside you. All right?"

"I love you so much" he said, tears filling his eyes. "I have these strange feelings now, and you're being so supportive. I can't even make love to you anymore, and you're treating me so kindly! I don't deserve someone like you."

"Dry your eyes. Lets try something new. Lets release the woman inside you. It might be fun even."

He looked up at me, with a smile on his face. I could not believe that this was actually working. I smiled back. I really had him now.

* * *

 

Over the next few weeks, I trained Jim with a pattern of behavior. If he was dressed as a woman, he was like the best friend I ever had. I would do anything for him. But when he was dressed as a man, I was indifferent.

Over time, it started to sink in that he got treated better when he was a girl. He liked it. And I think he was starting to like 'being' a girl. So I started making put on nail polish and makeup. I bought heels in his size (hard to find!).

We decided to let his hair start to grow out. Except that now he was shaving his legs, armpits, and had his eyebrows plucked. Just a few hairs each time, so it was a gradual change. Just like his budding boobs, which now were definitely larger than they had been before. I could see them slowly puffing up. I remembered back when I had been a teenage girl, and had gone through the same process. I taught him the exercises I used to do with my best friend, when we were in our bedrooms. They were supposed to help make your chest grow. I didn't know if they worked or not, but hey, it was worth a try.

 

After a while, I decided to give Jim a female name when he wore women's clothes. Calling him 'Jim' didn't seem to fit very well when he was in a dress. We decided on Margo, since that was the name of favorite movie star of his.

"Margo, you're so pretty today!" I would say when I saw him in the morning.

"Why thank you Ruby. You are very pretty too."

 

Eventually, he started to spend less and less time as Jim, and more and more as Margo. I hoped that soon it would become full time, and Jim would be something forgotten all together. Now was the time to move on to the next phase of my plan.

As I said before, I needed sex, but he wasn't a willing partner, even before I pumped him full of estrogen. I needed someone for myself. But that would be too much of a shock for him to take. So I started him on the right path by tricking him a bit.

"What do you think of a trio?" I asked.

"A jazz trio?"

"No silly! I mean in bed. Let's get another woman in bed with us, and do a three-way."

"I don't know..." he said.

"Come on! It will be fun! You can see how she does me, so you get some ideas on how a woman pleases another woman. You could do it as Jim, or as Margo. Whatever turns you on."

It took a few times, but finally, he caved in and agreed to do it (as Margo of course). I knew a friend of a friend who as into kinky things, so I set it all up. All I can say is that after having a real woman go down on me, one who knew exactly what a woman wants and needs, I was tempted to become a full time lesbian! I decided to keep that option open, in case my experiment with Jim didn't work out in the end.

But he seemed to enjoy it, and he tried to apply some of the techniques he had witnessed when he did me the next time. But it wasn't the same. He wasn't as sensitive. He didn't know when to back down, where to touch me, and although it was wonderful, it wasn't as good.

I let it go though, and kept things as they were for a while. Then I made a very daring suggestion to him.

"I want to do a trio again" I said.

"Me too. That was fun."

"But I want to be fair. Last time, I had a woman here for me. This time, I think that the third person should be a man."

"A man!"

"Yes. That would be fun, wouldn't it? Us two girls in bed with a man?"

"I don't know..." he said.

Again, with persistence and time, I got him to agree to it. But when it was getting close to the time when the young stud who I picked up at the bar was going to arrive, he started to chicken out.

"I don't know if I can be in bed with a man."

"Hmmm" I said. "Wait, I have an idea. How about you hide in the closet, and peek through the door. You can watch what happens, and learn."

"Really? You'd let me do that?" he said.

"Certainly Margo. Anything for you."

And so it was that I was in bed with a hot stud, making love, while my husband was in the closet, dressed as a woman, watching! I could not believe that it was possible. It was almost too good to be true!

* * *

 

For the next three months, I had Sergio come over three or four times a week, and made love on the bed, with Jim watching from the closet. It was only after all this time that he actually decided that he wanted to participate. His breasts were starting to fill out now, and his hair was getting long enough that it needed to be styled.

I set up everything with Sergio, telling him that there would be two women that night. He had no idea that Margo was really a man. 'She' never fully undressed, but she did bare her breasts and get them sucked by each of us. I felt so strange sucking a female breast, on the chest of my husband!

I did have to admit that I felt somewhat jealous when Margo was kissing Sergio instead of me, or when he paid too much attention to 'her'. But I got over it.

 

Almost every day Sergio came over. Sometimes, just we two did it. Sometimes, we had our three-way. Sometimes Margo would do me in the afternoon, then Sergio at night. We didn't even speak the name 'Jim' anymore. Even Margo thought of herself as a woman now. I was in heaven. I had everything! But there was one thing I hadn't counted on: I had done too good of a job.

One day I came home from the grocery store, and found Margo crying on the couch.

"What's wrong honey?" I asked.

"I was watching this show on TV. This mother had two children. I'll never get to be a mommy."

"We could always adopt. Or I could get pregnant" I said. (Hopefully from Sergio I thought!).

"But that's not all. I don't feel right. Between my legs. This is wrong. I want to be like you! I want to be a real woman."

I should have seen it coming. Margo had been so much more in touch with her emotions lately, and was starting to really act and think like a woman. So it was only natural that she would want to have a gender reassignment surgery eventually. I hadn't thought of that possibility.

She had gone to a doctor, and got a prescription for estrogen. I stopped changing her pills, because I read that too much of it could be harmful. But she was awash in it, and it had worked its magic, reshaping her mind, feminizing her thoughts.

So we began the process of finding a doctor, going through psychological screenings, and all of the work you need to do before they consider surgery.

* * *

 

It was a year since Margo felt the need to become a real woman. She had undergone the series of surgeries, and now finally seemed happy. Sergio made love to us, alternating which one he would penetrate each time. He moved in with us, and he was happy as a lark. Two women to screw, who wanted him all of the time.

So in the end, we were all very happy. I had love from Margo and Sergio, lots of sex, and I got to keep my house and everything. I was even really in love with Margo. I guess I did end up in a lesbian relationship after all!

Sergio was on cloud nine. He didn't have to work, so he was able to spend all of his time working out, swimming, working on his tan or his body. And he had all the sex that a nineteen year old male could ever want. We were more than he could keep up with.

But the happiest was Margo. She went from a dull, drab existence as an unhappy man, to one of love, warmth, closeness, and femininity.

We had all found ourselves, and our proper place in the world. I hoped that Sergio would never change. It wouldn't be nearly as much fun if I had to turn him into a woman too some day....

  

  

  

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2003 by Jennifer White. 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.