Separation Anxiety

by Jennifer White

 

Tom felt so happy. Anna was coming back to him. It had all started years ago, when they first married. They had been so happy together, sharing joy and happiness. They did everything together. The future looked so bright, and they were both so happy.

But over time, things got progressively worse. The arguments started. The drinking. The yelling. The nights of sleeping on the couch instead of in the same bed. And then they started spending time apart. When she asked him what he thought about calling it quits, and getting a divorce, he suggested a three month separations. They would go off on their own for a while, then get back together, and see what they might be able to do to give it another try.

Now the long wait was over. They were getting back together. He paced nervously as he waited.

 

When Anna showed up, she looked so pretty that Tom's heart melted. She looked quite different than when she had left. She had cut her long hair into a much shorter style, and had colored it blonde. But she looked thinner, and had an air of confidence about her, instead of the moping and crying she showed when she had left.

Tom wasn't any different in his mind, although he had put a few pounds on, and looked a little scruffier without having Anna there to help him dress better, remember to shave on the weekends, and take care of himself. Anna noticed these things that he failed to notice about himself. Typical.

"Hello Tom" she said.

"Hello Anna. I missed you" he said.

The walked up to each other and hugged. But they didn't kiss. There was still a coolness between them, neither of them yet sure that they were going to get together again, or if they would decide to call it off in the end. The slow dance of getting to know each other again had started.

* * *

 

The first few days together were like walking on eggshells. Tom was afraid to make any little mistake, fearing that if he did, it would end before it got started again. This was his last chance to stay together with the woman he knew he would love for the rest of his life. He knew that much of the blame for their fallout rested on his shoulders, even if he wouldn't always admit it.

Tom had many bad habits which, as he well knew, drove Anna crazy. Like the way that he would eat in the livingroom, and leave crumbs all over everything. Or the way he would just throw his dirty clothes on the floor, instead of putting them in the hamper.

"I'm not going to pick up your clothes for you anymore. You're not a child, and I'm not your mother" was what Anna told him the day they got into their big argument, which had started the whole chain of events leading up to their separation. So Tom was careful to throw his clothes into the hamper. And to eat only in the kitchen, and to wipe up the crumbs.

Anna seemed indifferent to these little gestures on his part, which disappointed him greatly. He was hoping that she would see that he had changed. But she kept her distance, and didn't quite seem to warm to him. And after two days, even though they shared the same bed, they had not yet made love. Tom knew that she wanted to talk about it first. This was another area where he had screwed up big time.

Tom had started to see Louise, his secretary at work, more and more often socially. When Anna was with her friends in their Tuesday golf league, he went out to dinner with Louise. One thing led to another, and he found himself sleeping with her ever Tuesday. And then they'd go to have a 'quickie' at lunchtime sometimes.

With Louise satisfying his needs, he had stopped pressing Anna as often to make love to him. It became so infrequent, that she had started to suspect that something was up. He of course denied it when she confronted him, but a woman has ways of knowing. A hint of perfume on his dress shirt from work. A little pink smudge on his handkerchief in the wash. A sudden disappearance of hundreds of dollars from the checking account (which he had used to buy presents for Louise). Along with his sudden decline of interest in bed, she *knew* something was up. And one other little clue that he didn't even suspect.

And Tom knew that she knew the truth, but he had not admitted it to her. Over their separation, he had broken up with Louise, and rededicated himself to Anna. He knew that if they were to be together again, he was going to have to admit his transgression to her.

It was perhaps the bravest thing he ever did in his life, to sit there on the couch, open up, and really talk to her that night. Talk to her, tell her how he felt, and admit what he had done.

"I love you *so* much" he said. "I would do anything for you. And anything to keep you. So I am going to tell you something. I'm pretty sure you suspected, but I have to let you know the truth. For a while, I was having an affair with my secretary at work. It started innocently, but it just got out of hand. It was wrong, and I feel so terrible that I would betray our vows like that. But it is over. I broke up with her, and had her transferred to a different division, so we wouldn't even see each other at work anymore. I was stupid, I was wrong, and my only hope is that you can find it in your heart to forgive me."

Tom actually cried a tear. He looked up at Anna, with a helpless look on his face, waiting to hear what she would say to him.

"I knew. I could tell. Even though you lied to me and told me nothing was going on, I just felt it in my heart."

"I am so sorry!!!" said Tom.

"It drove us apart, you know" said Anna. "It was the wedge that broke us in two. We never would have gone through all of this, if you had just kept your d!@k in your pants."

Tom flushed red. He wasn't used to hearing her talk like this. It was shocking and scary.

"So when we were apart, I did something to get revenge: I went out and found another lover of my own. I figured if *you* could do it, then *I* could get someone to satisfy my needs too."

Now Tom felt a burning anger inside. Some other man had been with his wife! He could just picture a man in bed with her, and it just crushed him inside. He broke down and started to really cry now. His Anna had been with someone else. And it was all his fault.

"Don't cry honey" she said. "Because I did it too, I can forgive you. We are even now. And it was quite an eye-opening experience for me. I tried some new and different things, and it opened me up to a whole new world I never knew was out there. And now I can apply those lessons, when you and I are in bed together."

Tom looked up, hopeful for the first time all day. She still wanted him! She was forgiving him! It had been a very painful thing for him to have this talk, but now they had worked it out, and everything was going to be okay. He hugged Anna, and cried even more tears, but this time for joy.

 

The couple celebrated their renewed closeness with dinner and drinks. Tom felt absolutely giddy from the bubbly champagne. It went right to his head. He never liked the taste of it (too dry for him), and this bottle was no exception. There was this bad sour taste that made him cringe. But Anna was enjoying herself, and kept pouring him one glass after the next. And now, he felt intoxicated.

Maybe it was all the excitement. Maybe it was the emotional rollercoaster of the day, and all the stress that went along with it. But after three glasses, he felt more tipsy than a whole bottle of wine would make him feel. But that didn't matter. He was about to go upstairs with his Anna, and for the first time in months, make love together.

When he finished off his fourth glass, Anna took him by the hand, and led him upstairs to the bedroom. She had to steady him, because he was staggering from side to side. He leaned on her heavily as the made it to the top of the stairs, where he had to gasp for breath.

They entered the bedroom, and Tom was stunned. There were a dozen candles placed around the room, all lit up. There were a dozen roses in a vase on the dresser. And laid out on the bed was a very sexy pair of red lingerie.

"Wow, you're going to wear those?" he said, slurring his words.

"No, you are" said Anna, with a smile on her face.

Tom didn't understand. Nor did he understand why the room was spinning so much. Or why he was having trouble keeping his eyes open.

"Anna..." he said.

"Go to sleep" she cooed. "When you wake up, you will be a beautiful woman, and then we can make love."

Tom slumped down on the bed, his mouth open, drool running out the side. He was out cold. The drugs had fully kicked in. And now it was time for Anna to go to work on him. There was much to do.

* * *

 

When Tom woke up, and his head hurt. His body felt very comfortable in the bed. Anna had put silk sheets on it, along with fluffy soft feather pillows. His body felt nice, but his head hurt. He went to rub his temples, but he was unable to move his arms. He opened his eyes and looked. Around his wrists he had leather straps, attached to a length of nylon rope, attached to the headboard. His arms were above his head, and he could not move them down.

He tried to scoot up towards the head of the bed to get some slack in the arms, but he discovered that his ankles were similarly bound to the footboard of the bed, and he was unable to move either way. All the bindings were under the covers, so he couldn't see them. But they were real, and they held him firmly in place, unable to move. He looked up, with a look of frightened panic on his face. Anna was standing over him, smiling.

"Hello love" she said gently.

"What's going on?" said Tom.

"Do you remember what I told you as you drifted off to sleep?" she said.

"Um..." said Tom, trying to recall. They were going to go to bed, then he sort of passed out. He remembered Anna's red negligee on the bed, and that was about it. What had she said? That he was going to wear it! Now he remembered. Why would she have said that?

"Why did you say that *I* was going to wear your red lingerie?" said Tom.

"Because my love, you *are*."

She reached over him, and pulled back the soft down comforter and the silk sheet. Tom's head was on a pillow, so he could see himself once the covers were removed. He *was* wearing Anna's red silky nightie. And on his chest, two unfamiliar mounds rose underneath it. He could feel their weight. They were perfectly shaped, with a protruding nipple on the tip, which showed clearly through the soft red silky fabric. This set his eyes wide with panic.

As his head spun with an overwhelming feeling of a loss of control, he was able to absorb more details, like how his toenails were painted a hot pink color. Or how his fingernails looked long now, shaped into ovals, and painted the same hot pink. Or how his legs were smooth and hairless.

And speaking of hair, he was noticing the long hair covering the side of his face. He cold feel it on his shoulders. Long hair, which smelled of hairspray. He also could smell other familiar scents. Perfume. The smell of makeup powders, the smell of lipstick. All at close range. He realized they were all on *him*. She was too far away to give off these odors. And they must all have been freshly applied to still smell. She had just put makeup on his face. He blinked, and noticed the long dark eyelashes for the first time. He was wearing mascara.

"What have you done to me!" he demanded.

"I am turning you into Jessica" said Anna.

"I don't want to be a woman! Why are you doing this to me!!" said Tom, really upset now.

"When we were apart, I decided that I had to understand your need to have a relationship outside of our marriage. I was going to find a new lover for myself, but I was just so disgusted with all men in general, that I could not bring myself to take one as a lover. I could easily seduce almost any man, but none interested me."

She walked around the bed slowly as she continued to speak, strutting suggestively.

"I was talking to a girlfriend of mine about my dilemma. She suggested a friend of hers who might be able to help me. So I went to see her. She was a wonderful, strong woman. Very strong. In fact, she seduced *me*, and made me into her lover. Oh the heights of pleasure that we found together! The very fulfillment of my soul. I had a partner who not only loved me, cared about me and my feelings, and knew what I needed it bed, but I also finally had a partner who *thought* as I did. One who was a perfect companion. A friend, a sister, a lover."

"You had an affair with a woman!?" said Tom, stunned. He never thought of Anna as being that adventurous.

"More than an affair" she replied. "She drew me into her. She *made* me fall in love with her. She changed me, to my very soul. She showed me what was possible. How a woman could actually control her lover, and change them into what she wanted them to be. And just as she changed me, I am now going to change *you*. You are going to become my perfect female lover."

Tom knew that Anna had changed. This was *way* out of the norm for her behavior. But there was no way he was going to do this. He was not going to become her lesbian lover! He was a man, and he was going to assert himself.

"That's it. This is all over. I want a divorce. Now get out of my house" he said sternly.

"*My* house" said Anna calmly. "And I'm not going anywhere. Neither are you, until you become my very willing and loving wife."

"I'm not going to become a woman!" said Tom.

"Yes you are dear. In fact, your transformation has already started. You are well on your way, whether you'll admit it or not."

"Just because you dressed me up in drag, and tied me to the bed, that doesn't make me female."

"That is true" she said. "But what about the female hormones in your bloodstream?"

"What?" he said.

"Oh yes. While you were sleeping, you took several injections. Your system is now awash in estrogen, and other female sex hormones. You won't need fake boobs for too long. Soon, you own real ones will start to grow."

"No!" said Tom.

"And on your back, where you can't reach, you are wearing several patches. Birth control patches, which release more female hormones into your blood stream, a little at a time. Bit by bit, cell by cell, you are slowly being feminized, even as we speak."

Tom let out what sounded like a whimper.

"But there is much more than that, as you will learn soon enough Jessica. First however, you need to start your lessons. You need to understand your new role in life, as my slave. Today, we are going to establish the new order in this family. From today forward, *I* wear the pants. And you will be in skirts. *I* am in control, and you are but a slave, existing merely to fulfill my wishes."

"No!" said Tom, struggling against the restraints.

"Tsk, tsk" said Anna. "Poor little Jessica is a disobedient girl. She needs to learn her place."

Tom continued to thrash about.

"Rule number one. You will obey me in all things, at all times. Do you understand?"

"No!!!" said Tom, trying to spit on her, but missing by a foot.

"I'm glad you're so stubborn" said Anna.

"And why is that?" replied Tom.

"Because, now I get to do this to you."

She pushed a button on a remote she was holding in her hand, and Tom's body started to jerk about, thrashing in what looked like convulsions, as he was overwhelmed with pain. After a second, it stopped, but he trembled for almost a minute after, his muscles not quite responding to the commands from his brain.

"That was level one. It goes to ten. For your sake, I hope I never need to go above level five. After that, the damage can be permanent."

"What is that?" said Tom in a raspy voice, as he struggled to maintain composure.

"It is like an electric collar used to train dogs, only modified to handle much larger voltages. You are wearing a leather collar around your neck, as a symbol of the fact that you are mine. The electronics are underneath. I should also warn you: the collar is wired so that if you take it off, you will be hit with level 10. As you can see, it only takes a few milliseconds to overwhelm you. I don't think you want to remove that collar. Unless you like pain."

Tom looked up at her. It was dawning on him that he was in no position to argue with her anymore. He was realizing that he was fully in her power. As long as she had that device, he couldn't do anything but to obey her. It filled him with rage and anger inside.

"You stupid b!#$*!!!" he said.

Anna smiled, and calmly pressed the button. As Tom lay there convulsing, she put her head down near his. "Rule number two, you will always address my politely. My Lady. Ma'am. Or whatever I tell you to call me. You may only call me by name, if I specifically give you permission. Like when we go out with another couple. I might allow you to dress up as a man, even though you will be wearing panties and a bra underneath. And I may allow you to call me 'Anna' on those occasions. But you always need to mind your place, as my slave. Do I make myself clear?"

She raised her hand with the remote. Tom nodded slowly. He had to do anything to keep her from pressing that button again.

"Rule number three, you are a woman now. Your name is Jessica. Tom is no more. In your mind, you must accept that you are now a female. It will take some time for the hormones to do their work, but eventually they *will* transform you. You must walk, talk, sit, eat, dress, think, act and *feel* like a woman at all times. After my experience, I could only take another woman as my lover. And that woman, is you. Do you understand?"

"I'm not a woman" rasped Tom, with whatever strength he had left.

"Tsk, tsk" said Anna. "You are a slow learner. Perhaps moving to level two will help."

She pressed the button, and Tom thought he was going to die. Level one had been excruciating, but level two made it look like nothing, by comparison.

"Tell me you are a woman" she said.

"No" replied Tom.

Zap!!!

 

"Tell me you are a woman" said Anna.

Tom was mute and silent. Sweat covered his face and body, and he looked like he was going to cry.

Zap!!!!

 

"Tell me you..."

"I'm a woman!!!!" said Tom. "My name is Jessica!!! Please, don't do that to me again!"

"I'm glad we had this breakthrough Jessica" said Anna proudly. "You need some sleep now, poor dear. Tomorrow, we will reinforce your training, until it is fully ingrained in your mind."

She injected something into Tom's arm, and everything when blank and numb. It was downright blissful. he fell asleep, muttering that he was a girl now...

* * *

 

Once she got past that first hurdle, the rest of Tom's training was fairly easy for Anna to accomplish. He was told to do awful humiliating things. If he didn't do them, pain was inflicted. When he obeyed and did something to prove that he was a woman now, he was given great pleasure.

Pain, pleasure, and random acts of kindness. Just when she seemed to be evil and mean, Anna would suddenly do something nice, like touch him on the cheek, and tell him that she loved him. His heart would melt for her. And as a result, when the training was done he was a changed man. He was completely obedient. He was deeply in love with Anna, with all his heart. And he was feminine.

Tom walked through the house, his high heels clicking on the hardwood floor. But he didn't think anything of that; it seemed normal to him. He was a woman, and those were the type of shoes that girls wore. He was in a dress. He had on a bra, and now he would have felt naked without one on.

Anna had been teaching him how to put on his own makeup, and he was getting rather good at it by now. And he was now used to responding to the name 'Jessica'. That was him now. That was who he was. He pushed all the pain and humiliation out of his mind, and only thought about the pleasure of being a woman.

 

As an example, during his training, Anna had made him masturbate into a paper cup.

"That's what a man does" she had said. "He gets hard, and he comes."

When Tom had climaxed, Anna explained more to him.

"Women on the other hand, we receive. We don't penetrate, we are penetrated."

She made Tom lay face down on the bed. She attached a lubricated strap-on to herself, and went at it with him as he laid there helpless.

"Now you're having sex as a female" she said.

As she rocked back and forth on him, she told him to take a sip from the paper cup. Afraid of getting zapped again, Tom obeyed her.

"Very good Jessica. Now you are a woman."

With that, Tom felt a pinprick on his neck, followed by overwhelming pleasure. All he could do was to bask in the glow of it as Anna kept repeating the words: "You are a woman."

 

By now, such individual incidents weren't something that Tom could think of. All he could remember was the core lesson: Being a man means pain and humiliation. Being a woman means love and pleasure. And so he walked through the house now in his female grab, moving like a woman, humming to himself, and in his very mind, thinking the words Anna had implanted so firmly in his personality: I am a woman.

* * *

 

Anna allowed Tom to put his man clothes on, so he could go to work. But as she had promised, he had to wear female undergarments. Today, it was panties and a bra. Tomorrow, she said he would wear red silk lingerie underneath his business suit.

His wig was gone, but she assured him that she would help him to grow out his hair into a style that could pass for a man, but could also look pretty, when he was a woman.

"I want to have long hair" he said. "So I can be pretty."

"Lots of men have long hair, and wear it back in a ponytail at work" she said.

"Then that is what I want to do."

"I love you" she said.

"And I love you" he replied.

He had never been so happy in all his life, as he got into the car and drove off to work. Anna had put a necklace of colored beads around the rear view mirror, to remind him that he was a girl now. In his suit pocket was a tampon, and in his jacket pocket he carried lipstick and mascara.

"Put them on while you're driving home" she said, and he was eager to obey. He always obeyed her. She was everything to him.

* * *

 

One day, when Tom came home from work, it seemed to him that Anna looked nervous. She never looked nervous! What was going on, he wondered?

Anna was dressed up in her nicest outfit. She kept looking into her compact mirror, and touching up her face. She was genuinely nervous, but she hadn't yet told Tom what was going on. After he cooked dinner for them, cleaned off the dishes, and wiped up the kitchen counter, Anna finally revealed the plan to him.

"Jessica, I have someone coming over tonight to meet you."

"That's nice" he replied.

"I want you to go upstairs, and get dressed up. Take off that maid's outfit, and put on something fine and elegant. Make yourself look pretty."

"Yes Ma'am" he said. "Who is coming over?"

"Do you remember how I told you that I met a woman, a strong woman, who made me fall in love with her?"

"Yes" said Tom.

"She is coming over tonight. She wants to meet you, so she can assess your progress. She will be judging me, based on how well you are doing. Now go! Hurry, there isn't much time to lose."

Tom scooted upstairs, took off his sexy maid's uniform that Anna liked him to wear when he cooked and cleaned. He replaced it with a nice outfit. After considering several choices, he decided to go with dark nylons, a straight-fit leather black skirt that came down to just above his knees. It went well with his pointed toe leather boots, with a four inch stiletto heel. Up top, he wore a white lace tee, with a V-neck. And on top of that, he wore a tight gray blazer, that had a single button which closed in front, right over his boobs. This drew attention to them, which made him feel more feminine and attractive.

He put on his makeup, touched up his nails, and walked back downstairs. He was surprised to see that Anna was seated, and very quiet. With her were *two* people: a tall thin blonde woman, who was wearing a sharp looking black leather miniskirt, and a tight fitting leopard skin cami, covered by an almost transparent chiffon top. She wore dangerous looking six inch heels. She was beautiful. And she exerted raw *power*. Even his Anna, as strong as she was, acted meek around her.

The second person was a man! He was seated on the floor, at the woman's feet. Although Anna and the women were talking, he was silent, just staring down, averting his gaze. It was clear even to Tom, that he was completely submissive to this powerful stranger.

 

"Jessica, this is Mistress Renee. You will treat her, as you treat me."

Tom curtsied, just as Anna had taught him.

"Impressive" said Renee. "I am here to test you Jessica. I intend to find out just what kind of girl you are, and just how obedient you have become. Do not speak to me, unless ordered to do so. Do not look at me, unless I give you permission. Do you understand?"

"Yes Mistress Renee" said Tom, looking down to the floor, as the man was doing. He bowed his head, and kneeled down, as Anna had taught him to do, as a sign of obedience.

"Very good. Come with me Jessica. And you too, Bryan."

Tom shot a helpless glance back to Anna, as he went into the spare bedroom, following Renee and Bryan. He couldn't let her down. He couldn't make Renee thing that she hadn't been good at training him. Anna gave a quick smile, and Tom's heart just melted. He loved her so much! Whatever they were going to make him do in there, he would gladly do it. For Anna.

* * *

 

It was two hours later when the three emerged from the bedroom. Anna was watching TV, nervously sipping her herbal tea.

"Anna, you have done a marvelous job" said Renee.

"Thank you, Mistress" she replied. This was high praise from her Mistress!

"Jessica is all woman now. She made Bryan very happy. Nothing I ordered them to do was too much. You have trained her well. So well in fact, that I might use her a few more times, as I break down Bryan into my total slave. I think they might both be well served by going out on a few dates together."

As Renee said all this, both Tom and Bryan stood mute, their heads down, looking at the floor. The women could talk as if they were not in the room.

"And just how did your Bryan perform?" asked Anna.

"Well, he was a little shy at first, because he always told me he wasn't interested in men. But after today, that is beginning to change. And Jessica liked what she did so much, that you might have to be careful, that you don't lose her to some man. He really went at it in there! It was quite fun to watch."

"Jessica, did you have fun?" asked Anna.

"Yes My Lady" he replied.

"Good. As a reward, go get your hormones, and show us how well you take them."

Tom went off to the kitchen, and returned with his pills. He gulped them down with a glass of water, then returned to the kitchen to put the glass into the dishwasher. A moment later, he returned.

"You know" said Renee, "in a few weeks, those hormones will fully kick in, and you will never be able to have another erection. You'll never be able to do what we did in there today. Does that bother you?"

"No Mistress" said Tom. "I hope they do kick in soon. I hate it when I get hard. It makes me feel male, and I hate that. I want to feel feminine. I am a woman."

Tears started to form in the corner of his eyes.

"There, there" said Anna. "You *are* a woman. And to me, you are pretty and feminine."

Tom looked up at her and smiled.

"I will leave you two alone. I can see just how devoted she is to you Anna. You have trained her well."

She? Her? Mistress Renee had called him 'she'? Tom felt flush with pride. Even this Mistress, this woman so strong that she could make his beloved Anna become tame and submissive, she was calling him by the feminine pronoun. Even in Renee's eyes, he was female. He never felt so proud in all his life.

"Come Bryan" said Renee. "Go get my purse. You will carry it as we walk to the car. Do you like how feminine and girly Jessica is?"

"Yes Mistress" he said.

No matter what the question was, the reply would have been the same.

"I'm glad you do" she replied. "Because *that* is your future. When we get home, we will start your conversion. After seeing how wonderful and female Jessica has become, I have decided that I will turn *you* into a woman too. Isn't that just delicious?"

"Yes Mistress" he said, but with a tremor of fear in his voice. Renee might have taken away his pride, and might have broken him, but inside he was still a man. Not for long though. She had plans for him now.

 

"You did wonderfully tonight my sweet" said Anna, after they had left.

"Thank you, My Lady" said Tom.

"You will be rewarded for this" she said.

"How?"

"Tomorrow, we will go to the mall, and shop for some new outfits for you. We'll get you new shoes, a dress, some skirts, a couple of tops, and maybe some jewelry."

"Oh thank you! Thank you!" said Tom, overjoyed a the prospect.

"Come now Jessica. While that male equipment on your dear sweet female body is still working, I want to make love to you. Soon, it will be inoperable, so we had better make good use of what time you have left. It is time for you to give me pleasure."

"Thank you My Lady" said Tom, grateful that she was allowing him to perform so important of a task. "Thank you."

  

  

  

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