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Make The Best Of It

by Jennifer White

 

"When you run into a difficult situation, all you can do is to make the best of it, and keep going" -Anonymous

* * *

 

Hunter looked at himself in the mirror, and smiled. His makeup had come out just perfect this time, much better than his last few attempts. With his wife being gone on business more as of late, it gave him greater opportunities to dress up in her things.

Today he had on her white skirt, which had drove him crazy, ever since they had gone shopping together, and she picked it out. Right then he *knew* he had to wear it. And today, that came true. It went well with her light greet top, which looked so nice with the full cups of her bra he wore beneath it. He had thought of buying a good pair of breast forms, but he didn't know where he could hide them, that she couldn't find. So he settled for using towels to stuff them. They didn't jiggle, but they made him look stacked.

He had on a pair of her pantyhose, which felt wonderful on his legs. He admired his legs in the mirror, then twirled around to feel the skirt fly out, then rub oh so gently against the sheer material. He loved that sensation, and how it made him feel.

"I'm a woman" he whispered to himself. When he was dressed up, his name was Taylor, and he was a glamorous actress. Now 'Taylor' moved over to the jewelry box on the dresser. There were all sorts of goodies inside, although it pained him that the rings were so small that they would only fit on his pinkie finger. Also, his wife had pierced ears, so he couldn't put her ear rings on. But he had a good pair of clip-ons which he kept hidden in his desk, and he already was wearing those.

The strand of pearls seemed like a good choice, so he put that around his neck, being careful not to smudge his makeup. He wished he had a place to hide a wig, so he could have a more feminine hair style. He couldn't manage all that much with his, and Sophia wouldn't like it if he grew it any longer. As it was already, she kept nagging him that he needed to get his hair cut shorter, so he would look more professional at work. But he resisted as best he could.

Now Hunter decided to put some perfume on. He chose a bottle, and sprayed a little on his wrist. It smelled lovely, reminding him of the cosmetic department, and all of the times since he was a young boy, that he would walk through it, admiring the beauticians, and wishing he was like *them*. They were the keepers of the secrets of beauty, young women who not only looked pretty, but knew how to help others who wanted to be pretty. He wished he was one of them, again, now. A young woman working behind the counter, selling mascara and blush.

He considered painting his nails next, but that took so much time, if he was to do it right. It felt like a waste, to have so much time flash by, when he could be doing other things. So the nails would have to wait until Sophia was gone for a full week, or at least a 3-day trip.

Hunter had carefully observed what shoes his wife wore, and had picked out a pair of her high heels which just sat in the closet, unused. They had an open toe, and straps that went around the back. Although his foot was too large for them, really, he was just able to get the leather to stretch out enough to get the straps closed. He put them on, and now he was in heels. They made a pleasant clicking noise on the tiles of the bathroom floor, as he checked his makeup yet again, and admired how feminine he looked.

Hunter picked up one of Sophia's spare purses, which he had taken from the closet. He slung it over his shoulder, and admired himself in the mirror again. He decided that he would go put on one of her hats. Perhaps the white one with the red band tied around it. That would hide his hair, and make him look even more feminine. Then perhaps a scarf to tie around his neck. Yes, that would be a great touch to his outfit.

He got them from the large walk-in closet, and put them on. There, now he was complete. He was no longer Hunter, he was Taylor. A beautiful woman.

 

He practiced his curtsey, then started taking small tight steps in the shoes. He was rather good at walking in heels by now, even though they were too small for him. They made his feet sore right away, but it was worth it, to see himself in them. He considered taking a picture of himself as Taylor again, but he was so afraid of being found out, and decided against it.

He would go downstairs, make himself some tea, sit on the chair with his legs crossed like a girl, and sip it from the cup. That was something girls did when they were at home, so it seemed like a good idea. He could read his wife's copy of Cosmo as he sipped his tea. Yes, he would be just like a woman.

He admired himself in the mirror yet again, and was about to turn around to go downstairs, when he noticed something in the mirror. Sophia.

 

She was standing there with her arms crossed, glaring at him.

"What in the h*ll do you think you're doing?" she said.

Hunter froze. His greatest fear was of being caught. And now, she had him.

"You know, I suspected you of this" she said, walking around him, to inspect how he was dressed. "Little things were starting to add up. You were sloppy."

"What...how..." he tried to say.

"Be quiet. You will not talk, unless *I* tell you to. Do you understand me?"

"Yes" he said, bowing his head.

"Good. You realize that I've got grounds for divorce right here and now. I can dump you, and you'll be left with nothing. None of my money, and just the little bit of nothing that you brought into our marriage. If you don't want to end up on the street tonight, dressed up like you are now, then you will do *exactly* as I say. Do you understand me?"

"Yes Sophia" he said.

"Now wait a moment. You don't deserve to call me by my name. You will call me Ms. Primont."

When they had married, Sophia had kept her last name. Now she was telling him to call her by it!

"Yes Ms. Primont" he said, ashamed of being caught as he was.

"Speaking of names, I suppose you have a name picked out, that you use when you are a woman?"

"Yes. Taylor."

"Yes what?" she said in a leading voice.

"Yes, Ms. Primont."

"That's better Taylor. You had best not forget your place again, or you will be severely punished. You have just rewritten the rules of our relationship. You are no longer my equal. You are no longer my partner. From this moment on, *I* am completely in charge of *everything*, and you are nothing. You are mine, and you will do my bidding. Do you understand me, Taylor?"

"Yes. Yes, Ms. Primont." said Hunter, correcting himself before she scolded him again. He felt weak now. Oh so weak. He was caught, and there was nothing he could do but to agree to what she dictated to him.

"Now as I was saying, you got sloppy as of late. Do you think I didn't notice how some of my things weren't in the right place? Or how my top got stretched out? How several pairs of panties have gone missing? Or how some of my makeup is running low, when I don't use those shades very often? You think you were being careful, but I pretty much knew you were doing this."

Hunter was about to speak, but she cut him off before he could get a word out.

"I cut my trip short, and came home early, just to see if I could catch you in the act. It looks like I have. I had you anyway, but I wanted to see for myself in person. Oh, you don't get it do you? Take a look here in the chandelier. Do you see this little white box that doesn't belong here? This is actually a camera, with an RF transmitter. I've been taking dozens and dozens of pictures of you today, dressing up and strutting around. I've got them all on my computer, and a backup on the server at work, in case you try anything. You can't destroy them all. And know one thing *Taylor*, I will not hesitate to use them if I feel threatened by you. Don't make me ruin your life."

Hunter knew that he was really in a fix now. If she made those pictures public, he'd be branded a pervert, and he'd lose his job, he'd lose his friends, he would lose everything. He was already on thin ice with Sophia as it was, and she seemed to be on the verge of throwing him out. And what woman would want him, if they knew what he liked to do in their clothes? His life would be a miserable mess.

His only hope was to make her happy, and to have her keep him. She was exerting her domination over him, so perhaps if he showed submission to her, she would show some kindness back to him. He got down on his knees.

"Ms. Primont, I am so sorry for what I did to you. I am yours, and I will do whatever you tell me to. Please allow me to serve you."

There. That sounded like something a domme would want to hear, if that was where she was going with this.

"I'm glad you feel that way, Taylor' she said. "I think we can work something out."

It was wonderful and terrible to hear her call him by his female name.

"Oh thank you Ms. Primont. Let me change out of your clothes, then perhaps we can talk."

"No Taylor. Those are *your* clothes now. After you've been in them, I have no interest in ever wearing them again. I'll give you a few other of my old outfits I don't wear anymore, and that will tide you over until we go out shopping, and build up your wardrobe."

"So you don't want me to change back?"

"No my dear Taylor. In fact, you are *never* going to change back. You are mine, and I command you to always go around dressed up as the woman that you are."

Again, it was terrifying and exciting for Hunter. It was a fantasy come true, but a punishment as well.

 

After their initial confrontation, Sophia lightened up quite a bit. She became almost friendly and helpful. She started by teaching him how to do his hair, how to do his makeup, and how to put together an outfit. She even did his nails.

It was quite frightening at first when she took him to the mall, but soon he was having the time of his life, living out his fantasy. He bought himself a whole new wardrobe. Skirts, dresses, pants, shirts, shoes, the works. He got his ears pierced. He went to the cosmetics department, and got a full makeover, after buying tons of stuff for himself. Before venturing out, Sophia had presented him with a wig, 'until your hair gets long enough to make it really pretty'. He looked more like a real woman than he ever had before.

Sophia supplied him with a good pair of breast forms, along with padded panties, girdles, and a tight corset to give him a more womanly shape. And of course, he was able to shave his legs now, along with his chest and underarms. Sophia helped him trim and pluck his eyebrows too. It was like they were sisters, and she was not only being kind to him, but paying for everything.

All was well and good, except for one small detail: ever since he 'became' Taylor, she had told him to sleep in the guest room.

"I don't bed women" she said. "I only sleep with men. You are no longer a man, so I have no interest sleeping with you in the same bed."

Not only did she no longer share a bed with him, but their close physical contact was gone too. No more hugging, kissing, or making love. He yearned for her, missing that part of their relationship.

 

In the mean time, Sophia was making him dress up as a maid during the day, and take care of all the housework. It was exciting at first to wear the little maid's uniform, with the frilly edging and the white lacy apron. But the dull drudgery of cooking and cleaning soon took all the fun away from him. He kept ruining his nails, and they needed constant touch-ups.

At night, he could dress as he pleased. He might watch television with her, but not sitting on the same couch. It went without saying that she got to pick the show. As it happened, that night she had on a romance movie. When it go to a scene where the couple went into the bedroom, and started making love, Hunter felt that he had to say something to her.

"Ms. Primont?" he said, using the name she was still insisting on.

"Yes Taylor, what is it?"

She hadn't called him by his real name for almost a month now.

"I see that couple on TV, and....and I want that to be us. I want to..."

"No Taylor! You're sick! I have no attraction to women! Don't ever suggest such a thing again to me!"

"I'm sorry Ms. Primont, but I feel so lonely, and it has been so long..."

"Yes Taylor, it has been a long time for me as well. But I've got good news for you. You see, on Saturday, I'm going out on a date. I found a really cute guy who is single, smart, nice, and..oh what the heck. He's a real hunk. We've been undressing each other with our eyes since we met. I'm going out with him on Saturday, then I'm bringing him back here, and we're going to make love all night long. I hear he's a real stud."

"But what about me?" said Hunter, upset and shocked.

"Don't worry Taylor, I have my plans for you. I still have the camera in the chandelier. I am going to film us, so that you get to watch!"

"No!" he said. "I can't watch that!"

"You can and you will. You see, you aren't a man anymore. Not a real one anyway. I want for you to see what a real man looks like, and you are going to watch him make love to me. You're going to watch me spread my legs wide open for him, and let him inside of me. And all the while, you will just watch us."

"Please don't do this..." he whined.

"I'm sorry Taylor, but it is all set up. I need to get laid, and I can't wait any longer. You're not a man anymore, so I can't do it with you. So I've found myself a man. A *real* man."

"But that means we'll get divorced" he said. "If you're having an affair..."

"Taylor, don't even go there girlfriend. You have no choice in this matter now. You left the bed for good when you got into my panties. Don't think you're ever going back. In fact, I want you to make me a promise right now. I want you to get on your knees, and vow to me, that you are never going to masturbate again. From now on, you will only get an orgasm when *I* say you can. Now do it!"

Hunter had no choice. Plus, his heart was breaking. Sophia didn't want him any more. Ever.

"You're not a man to me anymore. Now get on your knees, and vow to me that you won't make yourself come, ever again."

"I promise I'll never make myself come again. I promise, Ms. Primont."

"Very good Taylor. Good girl."

 

And now Hunter was cut off. No more sex of any kind, not even with his right hand. And now he had to think about how horrible it would be, for him to have to see her making love with another man. He got very little sleep, especially the night before Sophia's date.

 

That evening, Sophia brought him into her office. She typed her password into her computer, and clicked on a few icons. Moments later, the screen was filled with an image of the bed they used to share together. He looked at her, then back at the screen. He just didn't want to watch this at all.

"Go to the potty, then come back here. Do it now" she said coldly.

He wondered why she would want him to go, but he obeyed her, as he always had for the past five weeks. It was much easier to do what she said, even when it didn't make sense, than to argue with her. Her punishments could be quite severe, and he had learned not to question her.

He returned to her office, and she motioned for him to sit down on her black chair.

"Put your hands behind your back" she said, and he did. A moment later, he felt the cold steel of handcuffs going around his wrists. They were surprisingly heavy feeling, and he knew he wouldn't be able to get out of them.

Next, she tied his felt together, around the stem of the chair. Then she put a rope around his chest. He was trapped in the chair. The screen remained on in front of him.

 

"When I am done with my young lover, I am going to come down here and quiz you. You had better know what color his boxers were, what his tattoo on his chest says, and other little questions I'm going to quiz you with. You had better pay attention to what he does, and how he does it. If you don't pay attention, there will be very dire consequences. Do you understand me young lady?"

"Yes Ms. Primont."

"Good. I also want for you to pay attention to what a wonderful man he is. I want you to see what a real man is, and how he does. You'll also see that what he's got between his legs makes yours look puny in comparison. Yours is hardly worth even looking at, it's so small. You are nothing, but he is a *man*. I hope you enjoy the show."

 

With that, she was off. And Hunter could not move. He was forced to stay in the chair. Not only that, but he was going to have to pay attention, so that he could answer her questions! It was terrible. He was about to watch another man make love to his wife, and there was nothing he could do about it.

Time dragged by slowly, and it was torturous for him to just sit there and watch the empty screen. But hours later when Sophia returned with her young stud in tow, it was even worse, as he had to watch the screen. He watched as the young man took Sophia's clothes off, and kissed her all over. She was touching him in a loving way, grabbing at him, pulling him close to her. A couple of times, she looked right into the hidden camera, and winked at Hunter. She pointed to the small of her lover's back, at a birthmark there. he knew she would quiz him on that point later.

Now the man was naked, and he pulled off Sophia's panties. Hunter could only watch helplessly as the man started to suckle on her breasts, and play with her clit with his fingers. Now he plunged three fingers down deep into her, pulling them in and out. Sophia's face made Taylor know she was having orgasm after orgasm. He was surprised that he could hear their voices through the speakers on the computer. Her moaning and crying out with pleasure, and him telling her what he was going to do to her.

But now was the worst, as he mounted her, and started pumping, thrusting, in and out. In and out. Sophia's face was full of delight, and she grabbed her lover, pulling him closer and closer to her. It went on for a full twenty minutes, before her stud finally stopped pumping her.

By now, Hunter was in tears. He watched with blurry eyes as the two snuggled in bed. He couldn't reach up to dry his eyes and wipe away the tears. He looked down again, and Sophia was getting up. She smiled and kissed the man on the chest. The man thought he was the king of the world, laying in Hunter's bed!

"I'm going to get some water. I'll be back shortly" she said.

"Don't be too long babe. I want to go another round" he replied.

"Don't you worry about that, my darling!" she said, giggling, then turning to leave.

 

A minute later, as Hunter watched the man wearing *his* pajamas, watching *his* wide screen TV in the bedroom, he heard footsteps. Into the room walked Sophia. She was teetering a little, giddy from her session of lovemaking.

"He has a mole on the small of his back, his boxers are black, and his tattoo says something about his army unit."

"Very good" said Sophia. "So my little sissy girl *did* pay attention to the big man. How did you like the show? Oh look, the sissy girl has been crying. She's so sad. Perhaps it is because the big man got to come, while all the sissy girl got to do was watch?"

Hunter was in tears again now. He didn't even know what to say. Sophia smiled, and clicked a few things on her computer. A few moments later, the screen changed from a live view, to a replay mode. She moved the film to the right spot, where her young lover was sucking her nipples, and fingering her. She had it on pause.

"How long has it been since you've had an orgasm?" she asked.

"I don't know. Ten days?"

"And you really want one now, don't you?"

"Yes" he said.

"Well, I'm going to give you one now."

She reached down, and pulled up his skirt. Then she pulled his panties down to his knees. Just her touch got him all hard. She slipped a condom onto his erect member.

"Remember how I told you that you were only going to be allowed to come when *I* said it was okay?"

"Yes" said Hunter.

"Good. Well, now is one of those times. I'm going to release your hands, and you are going to make yourself come, as you watch the replay."

She pressed a key, and the computers screen showed her making love again.

"Go my little sissy girl. Come Taylor. Make yourself climax, as you watch a real man make love to me. I know you're jealous. Look how big he is! It almost hurt to let all of that inside of me. You're so puny, I could barely feel you. But he is a real man. Go harder now. Make yourself come."

It had been so long, that even with the terrible images he was seeing, and the awful things she was saying, Hunter couldn't help it. Bang! He came.

"Very good! Look at all of that! You really came hard, didn't you Taylor? Now I tell you what. If you promise to be a good girl, I'll leave your hands free, so you can do that to yourself again, as I go upstairs and have him make love to me again. In fact, that is the rule now: the only time you are allowed to make yourself come, is when you're watching me get laid. Now my lover is waiting for me. I hope you enjoy it the second time around."

 

Hunter cried as she left the room again, closing the door behind her. Soon she was back in the bed, and she started her second go-round.

* * *

 

From that day on, Sophia had different men over to the house on a regular basis. Some of them she had go down on her and suck her pussy. Some she got on top of. Some she laid down, and spread her legs for. It was only during those times that she allowed Hunter to have an orgasm, and get the release he so desperately wanted.

She no longer had to tie him down. She just put him in the room and told him that there better be a full condom when she returned. And it had better be warm, to prove it was fresh. She would have sex with her lover, then go into the room to check on him. Every time she checked, he had done as she asked.

He didn't realize it, but she was actually training him. She wanted him to get aroused from just the sight of her with another man. And by the end of the month, that was pretty much the case. Even her *talking* about being with another man, and he would get hard, because his body and mind had become used to *that* as the things which meant he would have an orgasm. He never felt so low in his life, when he realized that seeing another man make love to his wife had become a turn-on for him.

 

 

Another month passed, and Hunter was absolutely sick of it. He couldn't stand dressing up as a woman anymore. His hair was long enough now, that Sophia had him go to the salon, and get it styled in a pretty, feminine manner. But he didn't want any of it anymore. He wanted things to go back to how the used to be.

He was desperate, watching her bed one man after the next. He couldn't take it anymore. Life meant nothing to him anymore, and there was no hope. He became very depressed, and spoke very little. Finally, out of his last gasp of desperation, he confronted Sophia.

"Sophia, we need to talk" he said flatly.

"That's Ms. Primont to you Taylor."

"I can't do this anymore" he said. "I just want to die. If I see one more man in our bedroom, I'm going to kill myself. I can't stand seeing you with other men."

"Other than what?" she said.

"Me!"

"You?" snorted Sophia. "You're not a man. Other men? That would imply that you're a man. I haven't thought of you as a man for months. You're a woman to me now, a girlfriend. You ceased being a man long ago. And as I've told you, you're never going back to being one. End of discussion."

"No" said Hunter. "I've learned my lesson. I'll never even *think* of doing anything feminine again. I'm going to shower, take off these clothes, and dress up as myself again. Then I'm going to get my hair cut, and I'm going to come home and make love to my wife."

 

Sophia just smiled, as if amused.

"That's very funny. It almost sounds like a man talking. But there are a few problems with your plan my dear. First of all, how are you going to dress up in man clothes, when I've gotten rid of them all? Didn't I tell you? I gave them to the poor. You have nothing to wear but dresses and skirts I'm afraid. And how are you going to drive the car, when I've hidden your license? I'll report my car stolen, you'll be caught driving without a license, and go to jail. I'm sure those nice prisoners will love a sissy like you, all dressed up as a girl."

Hunter started crying. Yet again.

"And so you see Taylor, you can't leave. You can't leave me. You've chosen your life for yourself, and now you need to live it."

"No" cried Hunter. "I want to die then. There is nothing in life for me now."

"I'm so sorry that you feel that way" said Sophia. "Because next week, I had a big surprised planned out for your birthday."

"What's that?" said Hunter, through his tears.

"Well, since you're no longer a man, and since you make such a wonderful woman, I had an appointment made for you. I was going to give your breast implants, and start you on estrogen. You were going to sign papers getting your legal name changed to Taylor, and you were going to go on the waiting list for a gender reassignment surgery. You were going to become a real woman."

"What?" said Hunter.

"Oh yes. I was tired of seeing you suffer, so I was going to ease your pain. You're not a man anymore, at least not to me. So I was going to let you really become a woman. You could still stay here, employed as my maid, or you could leave, and do whatever you wanted. I have no problem with doing what I did to you. But as soon as you are a woman, legally, well that would be different. I couldn't hold a *woman* against her will. You'd be free my darling girl, and you could do whatever you wanted."

She was offering him a choice! Let him kill himself, or live, as a real woman. It was everything he had ever dreamed of, being female. He just never had the guts to go through with it. Now he had a chance, for real! He could become a woman all the way, and leave this terrible place. Sophia could do whatever she wanted, and he would be a free woman.

"I'll do it" he said, smiling for the first time in weeks.

"I knew you would, my dear sweet girl. I tell you what: you've been so good, that I won't do anything mean anymore. No more men coming over, until you leave. We'll be like sisters, and have a good time. What do you say?"

"Yes!!!" he said, crying. This time, they were tears of joy.

* * *

 

The next week was fun again. Sophia took him to get a makeover, to get his hair done, his legs waxed, manicure, pedicure, the whole works. She paid for laser hair removal on his face, and she got him a prescription for female hormones, which he gladly started taking.

He went with her to the plastic surgeon, and picked his new boobs out of a the array of photos they showed him. He bought new dresses and blouses. He bought skirts and shoes. Sophia picked out a nice condo for him, bought it, and moved all of his things into it. He had a place of his own now, where he could do whatever he wanted.

 

Sophia held his hand, as the sedatives kicked in, and they prepared him for anesthetic. When he awoke, he would have a pair of beautiful breasts on his chest. He had just signed the papers legally changing his name to Taylor. He had signed the divorce papers too. And he was on the list for GRS, which had a required six month wait. Once he got through the counciling, they would do the rest, and he would be a woman, just like he had always dreamed of. And he would be free.

"I love you Taylor" whispered Sophia, into his ear. She kissed him on the cheek, as he faded out into blackness. His transition to full womanhood had begun.

  

  

  

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2004 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.