Her Will by Jennifer White


Her Will

by Jennifer White


Emily sighed, as she watched her husband Will smoothed his skirt, then returned to putting on his makeup. It had been over a year into their marriage when she had walked in on him, fully dressed up as a woman. She had been so hurt that he had kept it hidden from her! She had wanted to marry a *man*, not a woman.

But after they had bought a new house together, tied their finances so closely together and everything, it would be hard to leave him. He did truly love her, but he seemed to love his cross-dressing even more sometimes. It frightened her to see just how feminine he became when he fully transformed.

He insisted that she call him “Alyssa” when he was dressed up, and he wanted her to treat him just like a girlfriend. He was so good at dressing up, that he could almost pass as a woman. They way he walked, the way he sat, the voice he used… all like a woman’s.

And over time Will kept adding more things for himself, always getting more and more elaborate. His latest purchase had been a pair of very realistic breast forms, which he proudly wore in his bra. It was bad enough that she had to play this game, but did he have to be so good at it? He was expert on putting on the makeup, and his face looked so pretty now that he was done.


When Emily had met Will, she thought he was so handsome, so kind, gentle, loving and sensitive. It was only when she found out his secret that she realized how strong of a feminine side he had. But Will only wanted her; he said he was completely devoted to her. She had tried to dissuade him from dressing up anymore, but it was futile.

“I married you to be my husband, not my wife” she said. “I don’t like you doing this!”

“But its a part of me” he said. “Whether I dress up or not, part of me *is* Alyssa. I need to let her out from time to time! Can’t you just play along? I want to fulfill your emotional needs too Emily, and if you can help me be a woman every now and then, I can learn how you feel inside, so I can do a better job of being there for you.”


And so, Emily had agreed to let him ‘become’ Alyssa a few times a month. Mostly, he would do it on a day when she was busy, so she wouldn’t have to see him. He swore to her that he would never go out of the house like that, even though shopping while dressed up as one of his favorite fantasies.

So he did his shopping on-line instead. Emily didn’t like how he was always buying something for his feminine self, although he would be thoughtful enough to buy her something pretty too, most of the time at least.


But it got to a point where it bothered her so much, that she decided she needed to scare him out of it. Her first attempt didn’t go very well though. She bought a pair of dildos, in a purple color, but very realistic, including balls, which you would hang onto as you inserted it into yourself.

“If you’re a woman” she said, “then you will need one of these for yourself. We can lie in bed together with these, and get each other off.”


She thought that the dld would be like a threat to him, and that he’d not want to go there. But unfortunately, he was *into* it. As she watched him sucking on his, her stomach turned so much that she couldn’t go through with her plan. She told him self felt ill, and left him alone. She didn’t want to know what he did to himself with it.


* * *


Emily did some careful planning, and came up with a second plan. This one was far more intense, far riskier, but also it seemed like the only way to really shock him out of his habit, once and for all. She did some shopping, she made some calls and some arrangements. And soon, her plans were all in place.

One Saturday afternoon, Emily spoke to will.

“I want you to go upstairs and become Alyssa for me” she said. “I have a new outfit for you. Put on your sexiest lingerie for me. Use your stockings and garters. Call me when you’re ready.”

Will was overjoyed. Emily had never *asked* him to become Alyssa before. When she had backed down from using her dld with him, he thought she was getting cold feet. But she seemed to be into it now! He kissed her, then hurried upstairs to undergo his transformation.

Emily sat on the couch, watching a movie on DVD, as she waited for the word from Will. It would take him over an hour to do everything. Right about on time, he called down to her, in his annoying voice, trying to sound female.

“I’ll be right up!!” she called out.

Emily went to the coat closet, and took down the suit-bag which contained the new things for Will. She went upstairs and looked at him. There he was, in all his lingerie, waiting for her. The breast forms on his bra looked so real! He had glued them in, and their tops were exposed, as he wore a demibra. But they looked real. She shuddered. A wife shouldn’t have to see her husband looking like that!

She unzipped the bag, and got ready to pull out his new clothes.

“As of now, everything between us is going to change Alyssa” she said.

Will shivered all over. She *never* called him by his female name before! He was overjoyed that she was getting into it now. His eyes bugged out, as she pulled from the suit-bag a sexy French maid uniform. It was black, with white lace trim. The skirt was dangerously short, and the front plunged down deep enough that his ‘cleavage’ would be exposed.

Also, there was a white apron that matched, along with a lacy cap for his head. There were also white gloves for his hands, which extended up to almost his elbows with lacy material.

“I also bought you this lace collar” said Emily. “It will hide your Adam’s apple, and it will also be a sign that you belong to me now.”

Will was so overjoyed at it all, that he allowed her to put on the collar, without thinking about becoming hers to command. That didn’t matter. He was just so happy that she was treating him like a girl now!

Next, Emily had purchased a pair of high heel shoes for him. The heels were five inches tall, much higher than he had ever worn. Will was almost drooling over the shoes, as he put them on, and strapped them up. He stood up, as Emily tied the apron on him.

“Now lets get some photos of you” she said. “I want you to always remember the day you became *mine*.”

Will gladly posed, as she snapped photo after photo of him from may different angles.

“Now get down on your knees Alyssa” she said. “Swear to me that you are mine, and you exist to serve me, and do my bidding.”

“I am yours” said Will. “I exist to do your bidding.”

“Tell me that you are *my* woman now, and that you belong to me.”

“I am your woman. I belong to you now.”

“Tell me that no matter what I order you to do, you will do it. Pledge total obedience to me!”

“No matter what you tell me to do, I will do it” he said. “I pledge my total obedience to you.”

“Very good Alyssa. You understand that you are mine now. I have the one thing you wish for more than anything in the world: a pussy. You are nothing, because you don’t have one. You don’t even have real boobs. Yet. But until you’ve got a pussy of your own, all you can do is to worship mine, and wish that you were like me. You are my slave now, to control as I please.”

Will just stared at her, his eyes wide open. She had never been assertive like this before. He liked it!

“You are just a lowly servant. You don’t have the right to use my name anymore. From now on, you will call me Ms. Taylor.”

It was her maiden name. Not his name. Her intention was to remove *all* of his power over her.

“Now get going Alyssa. I want the whole house vacuumed, the shelves dusted, the windows washed, and the laundry done. Go!!!”

Emily sat back now and enjoyed her movie, as ‘Alyssa’ went around cleaning the house. Not too bad! Every now and then she would ring bell, and call for her maid.

“Alyssa, go get a glass of an iced tea for me” she said.

“Yes Ms. Taylor” replied Will, as he scurried off to get it.

It was such a fun game for him to do the *woman’s* work of the house, and to serve Emily like she was his Mistress. How exciting for her to finally treat him like a girl! How joyful that she had finally accepted Alyssa as being part of him.

A few hours later, ‘Alyssa’ was in the kitchen, cooking dinner. ‘She’ had peeled and chopped the carrots, washed the lettuce, and all of the other prep work, before starting on the meal. Emily had reminded ‘her’ that ‘she’ would be cleaning up all of the dishes for after dinner.

Now ‘Alyssa’ set the table, using the fine china. A bottle of cold champagne was on ice, and all was ready. Will hoped that Emily would let him change into this blue dress he had, for dinner. It would be awkward to dine with her, dressed up as her maid!

He was rolling up the linen napkins, and threading them into the wooden rings, as Emily sat on the couch, reading her copy of Cosmo. He placed them by the silverware, and now the table was set. Almost as if on cue, moment he completed the table, the doorbell rang.

“Alyssa, would you get that please?” said Emily. “I’m busy right now.”

Will froze. He didn’t want for someone to see him in his maid’s outfit!

“Alyssa, now!!!” said Emily sternly, as the doorbell rang a second time. “Don’t keep our guest waiting! I gave you an order, and you are to obey me in all things. Now go!”

Will didn’t like this at all. Emily hadn’t said anything about inviting someone over. Maybe it was one of her girlfriends, so she could show him off to her. That might be fun, serving *two* women! Will walked over to the door, and opened it.

He was surprised to see a *man* standing there in the doorway. A tall, handsome man. The man paid him very little mind, other than to take off his jacket and hand it to him, as if he was a servant.

“It took you long enough” he grumbled. “Now where is the lady of the house?”

“She is in the livingroom” said Will, using his best female voice.

“Well hang up my jacket, so you can show me in” said the man.

Will was all flustered. This man was ordering him around, and he didn’t like it one bit. He hung up the coat, and told the man to follow him to the livingroom.

“Ah, Bradley” said Emily, as she stood up. “I am so delighted to see you.”

He walked over to her, and they hugged with familiarity, which sent a chill through Will’s body. She kissed him quickly, and Will saw his hand resting on her behind. He felt infuriated! Emily was his wife! Other men weren’t supposed to touch her like that!

But he didn’t act upon his anger. He just stood there.

“Don’t you have something to do besides stare at us?” asked Bradley.

“Go check on dinner Alyssa” said Emily, as she sat down right next to Bradley. He put his hand on her knee. Emily nodded and pointed again.

“She is very disobedient and slow” said Bradley. “I don’t see why you would keep a girl like that on. If she worked on my staff and she behaved so poorly, I’d send her back to the agency.”

“Oh, she’s not that bad” said Emily, as Will turned to go back to the kitchen.

“I have some good references, if you want to fire her, and get yourself a better maid.”

Will was almost in tears as he reached the kitchen. Why was Emily doing this to him? He stirred the soup, and checked the roast. Everything was almost ready. He took the roast out and carved it, then moved it to the serving dish. He filled two bowls up with the soup, placed it on his tray along with the roast, and carried it out to the dining room, where Emily and Bradley were already seated.

He put the soup bowls down in front of each of them, and put the roast in the middle of the table.

“She brings the main course with the soup, and she hasn’t even poured our champagne yet?” said Bradley. “Young lady, you need to learn your manners! Now pour our drinks!”

Will’s hands were almost shaking, as he uncorked the champagne, and poured some into two tall glasses.

“And I’ll have ice water as well” said Bradley.

Will had to return to the kitchen, get a pitcher down from the shelf, put ice cubes in it, fill it with water, and return with it, along with two more cups to the table. He poured them each ice water, then took a step back.

“Where’s the lemon?” demanded Bradley.

“Alyssa, go get him a lemon!” hissed Emily.

“But Emily, I don’t think we have any” replied Will.

“That does it!” said Bradley, standing up. “She call you by your name! This is just intolerable. After tonight, I’m going to take her home with me, and teach her some discipline.”

“Do you think that’s necessary, dear?” asked Emily.

“You don’t tell me what’s necessary” said Bradley. “I tell *you*. Is that clear?”

“Yes. I’m sorry I went against your judgment” she said, putting her head down.

Will was at a loss. Just a short time ago, Emily had been so strong, taking charge. Now she was being totally submissive to this horrible man! Will felt bad enough about Bradley ordering him around, but he was ordering Emily around too! And she was backing down to him, being submissive!

“Now lets try this again” said Bradley. “Your Mistress told you to go look for lemons. What do you tell her?”

“Sorry Ms. Taylor, but I think we have run out” said Will, his voice shaky.

“Very good” said Bradley. “You are just a servant. You don’t have the right to use her name. Now Emily, your servant cannot comply with your request. What do we do in this case?”

“I don’t know” said Emily. “Tell me what to do.”

“You will tell her to put it on the grocery list, and to do the shopping first thing in the morning. Then you will tell her not to ever let something like that happen again when you have guests.”

Emily nodded.

“Don’t nod to me. Tell *her*.” said Bradley.

“She heard you” replied Emily.

“I *told* you to do something” said Bradley.

“I’m so sorry dear” replied Emily. “It has been so long since I’ve been with a real man, that I forget my place.”

“Don’t let it happen again. I can see where your maid gets her poor attitude from. I would hate to have to teach *you* a lesson as well. Now do what I told you!”

“Alyssa?” said Emily.

“Yes Ms. Taylor” replied Will.

“Go put lemons on the grocery list. Tomorrow, first thing, I want you to go shopping. And don’t let something like this ever happen again when I have company! Do you understand me young lady?”

“Yes Ms. Taylor” said Will.

He was completely flustered now. Emily was letting this man order him around, and *her*! She was being so obedient to him, that it was scary. But maybe even worse, was the fact that she had just implied that he wasn’t really a man! Of course he was a man! He had always pleased her in bed. He had always loved her. Just because he liked to dress up as a woman didn’t mean he wasn’t a man anymore!

He hurried to the kitchen to add lemons to the grocery list, before he got into any more trouble. He worked on getting desert ready, when the bell rang. He was wanted again. He went back to the dining room.

“I have dropped my napkin. Pick it up for me” said Bradley.

Will wanted to tell him to pick it up himself, but he knew what kind of trouble *that* would cause! He bent over, picked up the napkin, folded it nicely, and handed it to Bradley.

“Here you are” he said.

“Here you are *what*?” said Bradley, leadingly.

“Here you are sir” said Will.

“Not good enough. You may call me Mr. Thomas. If you need to be disciplined further, I may make you call me ‘Master’, so that you learn your proper place.”

“Yes Mr. Thomas” said Will.

Now Bradley turned to Emily again.

“You selected a wonderful menu” he said. “You have very good taste.”

“That is why I invited *you* over” said Emily.

Will didn’t know what hurt worse; Emily getting credit for *his* hard work in the kitchen, or Emily fawning over Bradley, making eyes at him, as if he was something special.

The next hour consisted of Will going back and forth to the kitchen, being ordered around by both Bradley, and sometimes by Emily. Get this. Do that. I need butter. Pour my water. Clean up these crumbs. Back and forth. He was miserable by the time he cleared the table, and served desert.

When that was over, Bradley ordered Emily around again.

“Go to the livingroom and wait for me” he said.

She smiled, got up without a word, and hurried there. Now Bradley turned to Will.

“As for you, go clean up everything. The kitchen had better be spotless when I come to inspect it!”

Inspect? He was going to inspect the kitchen?

“You have been insolent, rude, slow and sloppy. You could also loose a few pounds. You’ve got nice boobs, but a serving girl such as yourself should have a better figure, especially if you’re going to dress up in something so seductive. No dinner for you tonight. Now get to work! I’ll check in, so no slacking off!”

Will was frightened, and started to clear the table, wash the dishes, and clean the kitchen. Of course, several times during this the bell was rung, to summon him to the livingroom.

“Alyssa” said Bradley, “I want a drink.”

“What can I get for you Mr. Thomas?” he replied.

“What do you have?”

“We have beer, wine, vodka, tequila, rum and gin” he said.

“And 25 year old scotch” added Emily.

Will fumed. That was his special bottle, which he only drank on special occasions! How dare she just offer it up to this terrible man!

“That sounds excellent” he said. “I’ll have the scotch. Shame on you for not offering it to me in the first place. Sloppy. Very sloppy. I’ll remember that. Now take your Lady’s drink order.”

“What can I get for you Ms. Taylor?” said Will.

“I don’t know” she replied. “Bradley, why don’t *you* order for me too. I just can’t make up my silly mind.”

“Alyssa, bring vodka and cranberry for the lady. And my scotch.”

“Yes Mr. Thomas” said Will, who hurried off.

It was painful to pour out the last of his favorite scotch, into the man’s glass. He made his wife’s vodka and cranberry, and placed it on the tray as well. Oh how he wanted a drink for himself now. He carried the drinks to them. They were on the couch together. Bradley had his arm around Emily’s waist, and she was looking at him like he was the most interesting person on earth.

“Here are your drinks” said Will, as he served them.

“What shall we have her do now Bradley?” asked Emily, as if she couldn’t think for herself.

“Go finish the kitchen, so I can come in and inspect” said Bradley, sternly. “I expect to be able to eat off the floor. Do I make myself clear?”

“Yes Mr. Thomas” said Will.

“Good. Then get going.”

Will was almost crying, as he got on his knees to scrub the floor. This was all too much. He didn’t want to be a maid anymore. He didn’t want to be a woman. It was one thing to serve Emily, but quite another to be at the beck and call of a man! And this was a terrible man, who was very cruel to him.

How could Emily betray him by being with Bradley? She was acting like she needed a man. She had *him*. What did she need Bradley for? And why was she so meek and silly around him? She let him boss her around too. Will didn’t like it one bit. No, not in the least.

Will was sore all over from all of the housework. But now the kitchen was spotless. Bradley, true to his word, came in to inspect. He nodded with approval as he checked out some areas. But he also wrote down some comments on a piece of paper.

“If you worked for me” he said sternly, “you’d be fired. If it was up to me, I’d give you a good spanking for your sloppy work.”

Will almost started crying.

“What did I miss?”

“What! You dare to question *my* judgment? And you don’t address me properly? You *are* an insolent one.”

Will was in a daze, as he looked around, trying to see what at all might have set Bradley off like that. He had cleaned *everything*, and had done so much hard work! He was trying to find anything wrong, as he heard the bell ring to summon him again.

He walked into the livingroom. There was Bradley, smoking one of his cigars, finishing off the last of his 25 year old scotch, his arm around Emily.

“Alyssa” said Emily, “Go and turn down the bed in my bedroom. Bradley and I are going to retire there for the night. Get a robe out for him too. He would like that.”

Will stared at her with wide eyes. She was going to *sleep* with him now too?

Bradley rose, as if to chastise him.

“Yes Ms. Taylor” said Will, quickly.

He was relieved as Bradley sat back down. He hurried upstairs, and turned down *his* bed for his wife and another man. He got out one of his robes for them man as well. He returned downstairs, wondering why Emily was betraying him like this. He saw her in the livingroom, but not him.

“Where is he?” whispered Will.

“In the restroom. We only have a few moments before he returns” said Emily. “Don’t let him catch us talking like this, or *both* of us will get in trouble.”

“What are you doing with him!” hissed Will. “Get rid of him!”

“I can’t!” said Emily. “You see how he is! He won’t listen to me. I’m just a woman. He wants me, and I can’t stop him from taking me.”

Emily just looked at Will, as if she was scared. But inside, this was the moment that all her hard work had been building up to. Now was the moment that Will would become a man again.

She had set things up perfectly. She had arranged for a dominating man to come over, who she had heard of through a friend of a friend. She had put Will in the place of being a female maid. His masculinity was being insulted every second, as Bradley was taking what was rightfully *his*. His scotch. His cigar. His supper. And his wife.

She had just made it clear that Bradley wouldn’t take an order from a woman. So there was one, and only one way to get rid of him: Will needed to be a man. All he had to do was to go upstairs, get out of his ridiculous outfit, and come back downstairs as her *husband* instead of her maid. He could tell Bradley to get the h*ll out of there, and all would be set. He would have learned his lesson, and realized that he *didn’t* want to be a woman anymore.

“I think I hear him coming!” whispered Emily. “Do something!”

“Quick, sit down” said Will.

He looked around, then started talking loudly.

“Yes Ms. Taylor” he said. “And is there anything else that I can do for you this evening?”

“No Alyssa, just the one task we just talked about” replied Emily. “Now get out of my sight!”

“Yes Ms. Taylor” said Will.

He turned to Bradley, who had returned.

“And for you Mr. Thomas. Do you need anything more?”

“I have everything I need right here” said Bradley, putting his arm around Emily. “Just have breakfast ready for me at 7:30. I want my eggs over easy, and the bacon extra crispy.”

He leaned over and kissed her.

“Come on babe” he said. “You’ll come upstairs with me. Now.”

Emily went up the stairs, following Bradley. He was pulling her forward by the hand. She gave a worried look back over her shoulder to Will. She was really upset. Why wasn’t he acting? Why wasn’t he doing something to stop this? He was actually going to let this man sleep with her, and he wasn’t going to even *try* to do something?

She looked back for one last glance of her husband, standing there in a French maid uniform, looking like a woman, and doing nothing to keep another man from having his way with her. She went into the bedroom with Bradley, and he closed the door behind them.

* * *


The alarm in the guest room went off at 5:30am. Will got up, and hurried to get dressed up in his maid’s uniform again. He had hardly slept. Through the walls, he had heard Emily’s moaning and screaming as Bradley had her all night. They had been at it for *hours*. He was devastated.

He decided that he’d serve them breakfast, get Bradley out of there, then he’d sit down with Emily for a long talk. If she didn’t want him anymore, then perhaps he needed to look at ending everything between them. He sighed as he put on his makeup, and checked that everything was in place.


Will went down to the kitchen, and started to cook breakfast. He made bacon, eggs, toast, coffee and fresh squeezed orange juice. He set the table, and waited for his wife and Bradley to come downstairs.


At 7:35, he heard footsteps. Bradley walked into the dining room, wearing Will’s own robe. Emily followed him, still wearing a baby doll nightie, her hair looking a mess.


“Good girl Alyssa” said Bradley. “I’m glad that you have done as I asked with breakfast. Otherwise, I would have to punish you.”


Will waited on them, as they ate. It was humiliating to do so. Bradley even made him go out to the mailbox in front, to pick up the newspaper. Now all of the neighbors had a chance to see Will in his maid’s uniform, dressed up as a woman.


At one point, Bradley got up to use the restroom for a moment. Will used this opportunity to talk to Emily.

“You’ve got to help me get rid of him!” he said.

Emily didn’t answer.

“Emily, aren’t you listening? We’ve got to do something!”


At that moment, Bradley walked back into the room. Will took a step back from Emily.

“Alyssa failed to address me properly” said Emily. “You are right dear. She does need to be disciplined.”


Bradley pointed a finger at Will.

“You will *never* do that again, when I get through with you” he steamed.

“Emily!!” said Will, as Emily calmly sipped her coffee. “Why did you do that!!!”

She put down her glass, and turned to him.

“I belong to Bradley now” she said. “And I would appreciate it if you addressed me properly! Bradley will have to punish you now. You won’t like his punishments.”

“Don’t do this!” said Will.

“You don’t understand” said Emily. “I can’t go against him! I am his now. As you will be too, when he is done with you.”


“What did you do to her!!” demanded Will.

“The same thing I will do to you” said Bradley. “I will make you mine too, *Will*.”


Will froze, and all of the color drained from his face.

“Oh yes, I know all about you now” said Bradley. “Emily has told me everything about you. How you like to be a woman. How you like her to use a strap-on with you in the bedroom. You’ll find that *I* am properly equipped, and I don’t need one of those to make you feel like a real woman.”


Will took a step back. His balance was uneven. He felt like he might faint.

“After I make you *mine*, I have plans for you” said Bradley. “Let me say first though, that your wife is very lovely, and I can’t understand how any man could not want to be with her. She is so accommodating and pleasing in bed. I think I will make you the same way, so that both of you can please me together.”


Will wanted to hit him, to do *something*, but he felt powerless.

“After I’m done with you, you’ll be completely mine, as your wife has become. I think I’ll keep you as the maid around here, so that Emily can spend more time in the sack with me. I am going to make an appointment for you. Tomorrow, you will go to see the doctor, to begin your first gender reassignment surgery. I’ll put you on hormones. I’ll have you buy yourself breast implants. Then you’ll have them cut off that little thing between your legs, so that I can do you any way I want. You’ll be a good lay. I’ll have them make your vagina nice and tight for me. But they’ll have to make it big, so that all of me will fit into you.”


“Emily!” said Will, desperately now. “Help me!”

“That’s Ms. Taylor to you” she said. “Soon to be Mrs. Thomas. As soon as you sign the divorce papers that Bradley is having drawn up. You’ll give everything to me, so I can give it to him when we marry. I’ll make you one of the bridesmaids.”

“No!!!” said Will.


“Enough of this insolence” said Bradley. “Now it is *your* turn to come with me. Emily, you can clean up with I teach Alyssa what it really means to be a woman. I will need to punish her, so it may be a while. You can ignore any screams you hear. When we’re done, your maid will be very compliant and obedient. She’ll be a good girl from now on.”


Will had enough. Something inside him snapped. He drew back his arm, and tried to hit Bradley. Bradley however was quick. He just laughed, and caught Will’s arm. He twisted it, forcing it behind Will’s back. His iron grip clamped down on Will’s wrist. Now he started to pull him, towards the stairs.


Will looked back helplessly at Emily, as Bradley dragged him off. Emily didn’t even look up. She was reading the paper and sipping her coffee. She didn’t want to do anything to anger her man. She wanted to be a good girl for him, so she didn’t get punished again as she had last night. She was Bradley’s now, in every way.

And soon, Will would be too. His life as man was over.