Now You Know How I Feel

by Jennifer White

 

Owen checked his dress, to make sure everything was just right. He didn't want Jan to get upset at him again for dressing in a sloppy manner. He sighed. How did things ever get this bad? Why did he have to be a girl now, and go by the name Caitlyn?

Jan was coming. He checked his makeup. He had to look pretty for her.

* * *

 

When Sue got divorced from her husband, there had been quite a battle over custody of their only child, Jan. He tried to use Jan purely as a bargaining chip, in order to pay less money in alimony. Never mind that it was his indiscretions with other women that led to the divorce.

Jan was really hurt. Although she was just 11 at the time, she knew what was going on. From then on, she never really trusted men again. Not after seeing what her own father was.

She was 16 now, and felt very close to her mom. But she was also hurting, because her mother had just remarried. Owen seemed nice enough, but as he spent more and more time with her mother, Jan received less and less attention. It was all his fault.

 

After the wedding, Sue and Jan moved in with Owen, in his nice house in the suburbs. On the surface, everything was normal. But Jan seethed inside with anger and resentment. How could they be living in the same house as a *man*?

But then a strange thing happened. Jan had never really been close with a male, but she was spending more and more time around Owen. And her hormones were kicking in. She started to look at him differently.

At breakfast, she look at him, and flash a playful smile. If he smiled back, she took it as a sign that even though he was with her mother, he really wanted *her*. Jan convinced herself that the only reason that Owen was with her mother at all, was to get close to her.

One day she saw him in his bathrobe, with his hairy chest exposed. Her heart started beating so fast! She got butterflies inside. She wanted him, and she was convinced now that he wanted her! It was just a matter of time.

Even at school, Jan couldn't stop thinking of Owen. She wrote his name and hers in hearts that she doodled in the margins of her schoolbooks. She imagined their life together.

Before she fell in love, Jan had brushed off all advances from the boys at school. And now, she really felt no use for them at all. Her life revolved around her new love.

* * *

 

"You've been very bad Caitlyn!" said Jan sternly. "You didn't coordinate your shoes with the rest of your outfit!"

"I'm sorry" said Owen meekly.

Jan always found something small to criticize him on. He didn't understand the finer points of women's fashion. Sure, Jan had him reading Glamour, Elle and Cosmo now, but there was so much to learn!

He felt so *aware* of the skirt encircling him. It felt at once both liberating (in how it flowed, compared to pants), and restricting (constantly reminding him that he was a woman now). Jan made him keep his knees together when he was dress up as a girl. It made him feel so weak and powerless to be like this.

"Today, several of my girlfriends are going to be online, in a private chat room. You are going to sign on to your new ID, and join in. We're talking about boys, which ones are cute, who we want, and stuff like that. You are going to act just like one of us."

"Please don't make me do this" said Owen.

"Now!"

He opened up his laptop computer, sat next to Jan on the bed where she had hers, and he signed on. His new ID was HotBabeCaitlyn46.

"I think that Andrew is really cute" wrote Jan. She elbowed Owen.

"Totally" he wrote back. "I want him."

* * *

 

Jan was sure that this would be the big day. It was valentine's day, and this was when she and Owen would really hook up. She spent so much time finding just the right card for him. She wrote a love poem, and wrote it in the card in red ink. Then she sprayed her favorite perfume on it before sealing it in the envelope.

She was so sure that Owen would buy her flowers, chocolates, then ask *her* to go out to dinner. She overheard him making reservations at Antonio's. Her favorite restaurant! Maybe he'd even let her drink some of his wine. It would be a perfect romantic evening.

 

Jan dressed up in her best outfit when she got home from school. She couldn't decide which pair of shoes to wear though, and had to try on three different ones before deciding.

But as she put them away, she realized that she should use the other ones. Yes, the platform shoes made her look taller, but the pumps made her look more adult. And that was what she needed tonight, to show him how mature she was.

 

"You're all dressed up nice" said Sue, when she arrived home. "Is one of the boys at school taking you out tonight? You didn't tell me anything about this. Who is he?"

"Its a surprise" said Jan.

She really would be surprised when she found out that Owen was going to take *her* out to dinner. Her heart leapt when she heard someone at the back door. Owen was home! He would be looking all handsome in his suit and tie from work. Jan went to get the card for him.

When she reached the kitchen, she was disgusted. Owen was kissing Sue! Why was he doing that? He loved *her*, didn't he?
"I have something for you" said Jan, handing over the card.

Owen opened it, smiled at her, and put it down. He did it way too quick. There was no way he would have read through the poem she wrote. He didn't pause to sniff the perfume. She was so sure he would hold the card up to his nose, take a deep breath, and tell her how it smelled nice, like her.

"Did you see inside?" she said, starting to feel a tremble all over.

"Yes. Thanks Jan. Your mother and I are going out to dinner now. We have a reservation. When we get back, I'll sit down and read your little poem."

He put his arm around Sue, and they headed out together. Jan ran to her room, slammed the door, threw herself on her bed, and started crying.

How dare he say that! Her 'little poem'? After all the hard work she did, Owen didn't even notice! He didn't care! He was going out with Sue, and not her!

He didn't notice how she dressed up for him. He didn't notice the shoes! He didn't buy her flowers or chocolates, or anything for that matter!

Jan's heart was breaking. All that she had dreamed of was fading away. He had hurt her so much, and he didn't even care! Men. They really were no good. How stupid she had been to think that he might be different.

She vowed to never fall in love with a man again. She hated them. They needed to be eliminated.

* * *

 

"Don't forget the windows Caitlyn!" ordered Jan, as Owen scrubbed the floor on his hands and knees. Jan had bought a French Maid costume, and made him wear it when he cleaned the house.

He put the sponge back into the bucket, wrung it out, and worked on the next area of the linoleum. Sue was out of town again on business, so he would be stuck like this for two more days.

"Quit daydreaming Caitlyn" said Jan. "You're thinking about boys again, aren't you? You need to concentrate on your house work first. We can go to the mall later."

The mall! How he hated it when she made him take her shopping at the mall. He would have to buy a bunch of clothes for her, as well as for himself. And he would have to do it while dressed up. He hated how everyone stared at him when he went out in female clothes.

"As soon as you're done with the windows, you can take a shower to clean up, and shave your legs. Then after you get your makeup on, we'll go shopping. There's this really cute skirt on sale, and I think it would look great on you."

That was just about the worst, when he had to go into a women's store, and try something on. The looks he got from the clerks, and the other shoppers! Just about the only thing worse was when Jan would flirt with the guys when he was there. She kept telling him that she was going to set him up with one of them for a date. That was the worst thing.

He also had to endure the fact that Sue didn't know what was going on. One day, Sue complimented Jan on her housework.

"You've done a wonderful job of keeping the house clean lately dear" she said.

"No problem mom. All this house needed was a woman's touch."

She shot a knowing glance to Owen. A woman's touch? It had been *him* doing all the work. And she gave him credit *as a woman* for doing the work.

 

"Caitlyn, you missed a spot! Now you have to redo that whole side again. When I give you a job, you are to do it right. Understand?"

"Yes Jan. I'm sorry. I've been a bad girl" said Owen. That was what he had to say when he messed something up.

Jan stood over him and smiled. She liked her slave.

* * *

 

After the disaster on valentine's day, Jan mostly stayed in her room alone, rarely even joining her mother for meals. Her mom was having to travel more and more for business anyway, so two or three nights a week, she wasn't even there.

Meanwhile, Jan plotted. She went on the internet from her laptop computer, looking a different web sites, trying to think of what she could do to Owen. Almost by accident, she found one that made her smile and evil smile. She knew *exactly* what to do now. This was going to be so perfect! She did waiver a bit though, not sure if this was really something to follow through with. But Owen didn't help matters very much.

He was very distant from her now. They rarely talked or interacted. In fact, he was sometimes even mean to her now. Instead of letting her come along when he went out to dinner with Sue, he would make her stay behind. He made her do more chores around *his* house.

Perhaps it was to be less kind, so that she wouldn't want to love him anymore. Or perhaps it was because he really was a mean person. But either way, he kept getting worse and worse, which hardened Jan's heart. There was no way that she would reconsider now. She was going to go through with it.

 

It took a few weeks to get everything ready. Tonight, her mom was gone, but Owen was home It was time to begin.

Jan stripped down to just her panties. She admired her large, firm breasts in the mirror. She moved to the penny she had put on the floor to mark the optimal spot for the hidden camera to catch the action.

"Owen!!!" she screamed. "Help!!! Come quick!"

A few moments later, he dashed in the door.

"What's wrong?" he said, as she put her arms around him and gave him a deep passionate kiss.

"What are you doing? Why aren't you dressed?" he said. "This is crazy. I'm going."

He turned and walked out the door. Jan calmly put her bra back on, then threw on shorts and a long T-shirt. She went to the computer to check out the results from the camera in the corner.

It was perfect, just like she had hoped. You could see Owen rush in the door and run to her. You could clearly see that she was naked. You could see them kissing. And from the camera angle, you couldn't tell that she was the one doing it all. It looked like he was a willing participant. Perfect.

She edited down the file, cutting out Owen's exit. She put it on a CD, then made a second copy. She also emailed the file to a girlfriend, who had promised not to look at it, but to just save it.

Jan took one of the CDs, and carried it into the living room where Owen was.

"You need to see this" she said, handing it to him. Owen picked up his laptop computer from the table, opened the drawer, and put the CD in.

He saw the video of Jan standing nearly naked, and vulnerable looking in her room. Then the door burst open, he rushed in, and they kissed.

"What is this!" he said. It looked like *he* had been the initiator, when in fact it was all her!

"This are going to be different around here from now on" said Jan calmly. "I have multiple copies of the video, including one that I've sent off to a friend of mine over the internet. So even if you ransack my room, and find the other CDs, and throw out my computer, I still have the evidence on you."

"Evidence?" he said.

"You are going to do exactly as I say, from this moment on. Otherwise, I will release the video to mom, your boss, the police, and the newspapers."

"Jan, what's going on? What..."

She cut him off.

"*I* am talking! Be silent!" she said harshly. He never heard this tone of voice from here before. A commanding tone, with force and power. He stopped talking.

"I am going to tell them how you have taken advantage of me. How ever since we moved in, you've made love to me. I'm 16, so you're in big trouble. Its statutory you know. And I'll tell them how you forced me to be silent about it, until I used the camera to get evidence."

Owen was a 42 year old man, six feet in height. But this little *girl*, just 16 years old, was taking control of him. He felt completely powerless. Everything was starting to slip away from him, as he listened to her.

"If you ever so much as think of disobeying me, I can and will go to the authorities. With the video evidence, it will be an open and shut cast. You'll do hard time. Do you know what they do in jail to people who have committed that kind of crime with a minor? You'll be dead meat."

"Please!" said Owen. "What have I done to make you do this?"

"Silence! You have no right to talk, unless I tell you to. There are some new rules around here. Number one, *I* am in charge. Completely. Do you understand?"

"Yes" he said, unable to think of a way out of his steadily worsening situation.

"Second, to remind you that you are completely subservient to me, I am going to turn *you* into a girl. When mom is gone, you will dress up like a girl, act like a girl, and *think* like a girl. Your name will be Caitlyn."

Owen was stunned. What in the hell was she talking about?

"Now tell me that you're a girl!"

"Jan, please, don't do this" said Owen.

Jan took her cell phone out, hit a button, and held it up to her ear.

"Hi, Jan here. We have a code blue. Unless I give you the signal, send out the tape."

"No!" said Owen loudly.

Jan held the phone away from her ear.

"What did you say? You dare disobey me?"

"No, you win. All right? I'm a girl. I'm a girl!"

"All clear" said Jan into the phone, closing it and putting it back into her pocket. Now she turned back to Owen.

"Say it again. And tell me your new name."

"I am a girl. My name is Caitlyn."

"Very good Caitlyn. You are a very obedient little girl. Now listen carefully. You haven't been trained yet, so I allowed you this one exception. There will not be a next time. *Any* insubordination from you, even a hesitation in obeying an order, and poof! Your life will be gone. Do you understand?"

Owen bowed his head, defeated. She had him over a barrel. There was nothing he could do now.

"I understand" he said.

"Good. Now we can begin your training" said Jan, with a wicked smile on her face that sent a chill down Owen's spine.

* * *

 

As the drove back home from the mall, Owen thought back to that first day, when Jan had made him wear a dress. He hated it of course, which only encouraged her to make him look and act more and more feminine.

She had 'trained' him, teaching him how to walk, how to sit, how to talk and how to act like a girl. He was under constant threat from her, and he was never able to figure out how to get over the blackmail threat she held over his head.

A couple of times when she first started, and he was slow to obey, she would make him do something really awful. He learned to avoid that, by being 'a good girl', and precisely following any and all orders from her. She really did control his life now.

 

"Contraception" said Jan.

"What?" replied Owen.

"The Pill."

"What about it?"

"Sexually active girls need to be careful, so they don't get pregnant. And you are a teenage girl, right in the age group where you're starting to be sexually active. So I have decided that you're going to go on the pill."

"But doesn't it contain female hormones?"

"Yes. The hormones trick your body into thinking its pregnant, so you don't conceive, even if you have sex."

"But that will..."

"When you get pregnant, your boobs get bigger and stuff like that. But what girl doesn't want bigger boobs? Tell me Caitlyn, tell me again how you want big full breasts."

"I wish I had big full breasts" said Owen.

"See? So the pill will actually help you."

Owen was scared now. Up to this point, there hadn't been anything that she had made him do that was *damaging*. But this was different. It would alter his body. After some time, people would be able to tell. How could he do something like take a swim, if he had female breasts growing on his chest.

This was really upsetting. Before, it was like acting, or playing. But this was real. This was something physical. This would really start turning him into a woman.

 

Of course, there were no visible effects of the pill after just a week, but it made Owen feel utterly defeated. He started to get depressed. He really didn't care anymore. He was thinking of just packing up in the middle of the night, and leaving town.

"Put on your best dress tomorrow" said Jan. "It will be a special occasion."

Owen frowned. Jan's special occasions usually turned out to be torturous. He became more firm in his mind that after Sue returned from her trip, he'd run. It was the only viable alternative, and better than really being turned into a woman.

* * *

 

Owen got home from work a little early, just as Jan had ordered him to. He went through his process of transformation, putting on the clothes and makeup to 'become' Caitlyn. He had fake breasts, a wig, and padded panties to help with the illusion.

He checked in the mirror when he was done. He was wearing a white skirt, that had several cascading tiers. Almost like wearing a short skirt over a medium one, over a longer one, over an ankle length one. Each tier ended with lacy trim. He felt even weaker when he had to wear this one for some reason. The frilliness of it seemed to take away any manliness he still held within himself. Of course, that's why Jan loved it so much.

On top he wore a light pink blouse, with puffy shoulders, lacy cuffs and trim. Jan tied a ribbon in his hair too. And she made him put on lots of jewelry, and extra makeup. She sprayed him heavily with her perfume.

"What's the special occasion?" he asked as she painted his fingernails.

"Oh, you'll see soon enough."

 

Jan had rented a romance movie, and she sat right next to Owen as they watched it.

"This is what girlfriends like to do" said Jan. "Sit together, watch a chick flick, and talk."

Owen wasn't very happy about things. But at least she was treating him very nicely today, more like a friend than a slave.

 

Suddenly, the front door opened, and in walked Sue.

"Hello Jan, I'm home early, like I told you. Oh, you have a friend over"

Owen's face had been obscured by the hair of the wig. But when he turned to face her, Sue immediately recognized him.

"Mom, I was going to tell you, but I promised him I wouldn't say anything" said Jan, her voice shaky, her eyes filling with tears.

"How dare you!" said Sue, enraged. "Get the hell out of my house! Get away from my daughter you pervert!"

"Wait honey, it isn't what it looks like..." said Owen.

"Not what it looks like? I come home to find out that my husband likes to dress up like a teenage girl, and it's not what it looks like? Get the hell out of my house!"

"This is my house!" said Owen.

"Not anymore! Not when the lawyers are through with you. Now get out!"

"Let me change clothes first..." said Owen.

"No! Go now, or I'll call the cops!" she said, grabbing her cell phone.

Owen had no choice. He stood up, teetering a little in his high heels.

"Don't forget your purse Caitlyn" said Jan, helpfully.

"Caitlyn is it?" said Sue. "What a pretty name, for a *girl*."

Owen was ashamed. He walked to the front door, under the glare of the two girls.

"Here's your car keys" said Jan, handing them over. There was a piece of paper on the key ring, with a handwritten message: "Now you know how I feel."

Owen walked out, and got into his car. He had nowhere to go, and no idea of what to do next. Tears actually filled his eyes. It must be the hormones, making him like this. Perhaps he really was cut out to be a girl. He couldn't think straight. He was too emotional.

Jan went over and hugged her mother.

"I love you. Thank you for saving me from that monster. He was so mean to me" she said.

"There, there darling. Everything is going to be all right" said Sue. We'll forget all about him and get on with our lives.

  

  

  

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