The Best Laid Plans

by Jennifer White

 

Everything was set. The neighbor would bring in the mail for them. The bags were packed. Mora's mother would come over twice a week to water the lawn and the flower beds. The reservations were in place. Dan's sister would drop them off at the airport. And Mora's brother would pick them up.

Mora and Dan had been planning their vacation for months. Now, everything was ready to go, and the big day had finally arrived. They had been married for five years now, and they had been waiting for this since they promised each other on their honeymoon, that they would return to the Bahamas once they reached this point in their marriage.

Right on time, Dan's sister Becky pulled up into the driveway. Dan loaded the bags into the trunk, Mora double checked that everything was ready, and they got in. Traffic was smooth, and in just 45 minutes, they were at the departures level.

After unloading the bags, Mora kissed Becky good-bye, and Dan gave her a bear hug. They waved as she drove off, and turned towards the terminal.

"Lets use the sky-caps" said Dan, pointing to the uniformed men at the podiums outside. "It will be faster than standing in that long line."

"Sounds good" replied Mora.

Each had one large bag with their clothes, and a small carry-on bag. The sky-caps checked them in, tagged their bags, and put them on the belt. With boarding passes in hand, Dan and Mora waited in the long security line, and passed through without incident. They had planned on arriving early enough that even if things were slow, they wouldn't be pressed for time. And now their planning had paid off. They arrived at the gate, with lots of time to spare, so they went to the bar for a tropical drink before getting on the plane.

When the gate agent called the flight for boarding, they got into their assigned seats. The modern transport system was a wonder: in just a few hours, they were away from the cold and snow of the north. Now they were on a tropical island, with sunny skies, sandy beaches, and warm tropical breezes.

They waited for their bags, and Mora's was one of the first ones off the belt. Now they just needed Dan's bag. They watched as bag after bag came off the belt, but they didn't see Dan's bag yet. Dan had a sinking feeling in his stomach when the belt stopped, and no more bags appeared. The airline had lost his luggage!

 

He sighed. What incompetent idiots! How could they have lost his bag? He walked over to the airline luggage office, and stood in line to report his missing bag.

"Don't worry honey, the bag will turn up" said Mora, supportively.

"Humph" said Dan, his arms crossed.

Finally, it was their turn to speak to the agent.

"My bag didn't show up" said Dan.

"I'm so sorry sir" said Vicki, the airline luggage agent. "Let me check the computer."

She typed and typed, and kept shaking her head.

"I'm sorry sir, but I don't have a tracer on your bag yet. Hopefully, it will show up on the next flight, this afternoon. Write down your hotel address here, and we'll drop off the bag when it arrives."

"What if the bag doesn't show up?" said Mora.

"You can spend $100 today for clothes, then $50 a day after that, until your bag shows up, with a maximum of $450. Most hotels will give you toothbrushes and toiletries if you're missing them."

That soothed Dan's anger a bit. He could buy some things, and make the airline pay for them. They had wasted an hour of his vacation waiting for his bag, and he was determined to stick it to them.

 

Half an hour later, Dan and Mora reached their resort hotel. They checked into their room, and Mora unpacked her bags.

"I'll go downstairs, and pick out some clothes" said Dan.

"Sounds good" said Mora, trying to get the wrinkles out of the skirt she had pulled out from the suitcase. She shook her head. She was going to need to iron it. It bugged her to have it all wrinkled like that!

 

Dan went downstairs to the hotel shop. He returned just fifteen minutes later, as Mora was finishing her unpacking.

"That was fast" she said.

"Well, we're going to be at the beach all day, so I didn't need very much" said Dan, showing her a tropical shirt, and a swimsuit. "But this only cost me $40. We need to spend the other $60 today. Do you need anything?"

"I'm okay" she said.

"I know, but I want the airline to pay us every cent they owe us."

"You know me" said Mora. "I can't resist free shopping."

 

Down in the store, Mora insisted that Dan buy a pair of boxers, and a pair of flip-flops. That left her $50, with which she bought a tropical skirt. That left $7, which she used to buy a bra which was on sale. A girl can always use a spare!

They went out to the beach, and forgot their problems as they tanned in the sand...

 

* * *

 

Dan's luggage didn't show up that day, nor the next. He spent a few bucks to buy shorts, and Mora spent the rest on panties. On the third day, he bought socks, and she bought a tank top. The fourth day passed, and the fifth. Still, no bag! Eventually, they reached the $450 limit of replacement clothes, but that was just fine with Dan. He had a couple of new things, and Mora had a bunch of stuff.

And as luck would have it, the very next day his bag finally turned up! It had been put on a plane to Peoria, then had been misrouted to Chicago, where it sat for days. Finally, they brought it back to the airport where it had originated, then it was sent down to the islands. Dan was delighted when he showed up at his room, and his bag was on the bed!

The rest of their vacation was trouble free from that point.

 

 

When the vacation was over, and they were back home, Dan sent in the receipts along with the form from the luggage office. And two weeks later, he had a check in hand for $450 for the replacement clothes he had bought, along with Mora.

The lost luggage adventure was forgotten, and the loving couple settled down to their normal lives. Or so they thought. Dan was at work, and got a frantic call from Mora.

"Dan, we need a lawyer! I can't believe this. This is so terrible! What are we going to do?"

"What's wrong babe?" said Dan.

"This is just so bad. We're in such big trouble. I never thought they'd do this! Oh, what can we do?"

"Slow down honey. Take a deep breath. Just tell me what the problem is."

"The clothes we bought, when they lost your luggage."

"So? We got paid by the airline."

"I know. And that's the problem. They looked over all the receipts we sent it, and they want to charge you with fraud!"

"Fraud?" said Dan, stunned.

"Yes. They sent a legal document thingie to us, saying that you're being charged with fraud, because you used the money to buy clothes that weren't for you, but you charged the airline for them. You could go to jail! This is so terrible! What are we going to do?"

Fraud? Jail? Dan's mind was reeling. How could it have gone so horribly bad? Yes, he had tried to 'stick it to' them by buying things for Mora as well as for himself. But how could it have come to this?

Dan tried to calm Mora down, and told her that he'd leave work early, to go see their family lawyer. He was very nervous as he sat in the waiting area at 4:00 with Mora, reading the document the airline's attorney had sent them. It was even more nerve wracking to watch their lawyer read it, and shake his head.

"I'm afraid that they've got you" said Jack Feldman, their lawyer. "You committed fraud, and now we'll have to go to court. We can try to plead it out, and see if you can get off with probation and a fine. But if they won't take your plea, you could in fact do time."

"Isn't there some other way to get out of this?" asked Mora.

"Yes there is, but I'm sure you wouldn't like it" said Jack.

"Tell me! What can we do?" asked Mora, with a ray of hope for the first time since she received the document.

"We would need to prove to the court that the clothes weren't for you Mora. We would need to prove that they were for Dan."

"For me?" asked Dan. "What do you mean?"

"They are questioning the bras, panties, skirts, the bikini, and the women's tops. If we could prove that they were for *your* use, then they wouldn't have a case."

"And how could we do that?" asked Mora.

"We would need to establish in court, that your husband regularly wears those types of clothes."

Jack proceeded to tell them exactly what they would need to do in order to prove it. They would need witnesses. They would need receipts. They would need proof.

"Of course" added Jack, "as a lawyer, I can't give advice to you if it meant covering up a crime. I'm just stating what you would need to do, if those clothes really were for yourself."

"I understand" said Dan.

"So I need to know from you, how you want to proceed. Go to trial, or plead it out. And if we do go to trial, I need to know: are the women's clothes in questions *yours*?"

"Yes" said Mora. "Yes they are. They were for *him* to wear."

Dan elbowed her a bit, but she shot back with an intense look of anger that told him to back down.

 

In the car after they left, he turned to her.

"How could you tell him that?" he said. "That I wear women's clothes?"

"But Dan, it is going to be the only way out of this mess. Do you want to go to jail? Or to have a criminal record, even if you do plead out?"

"No..." he said.

"Then we need to stick to the plan."

"So what are we going to do?" he asked.

"We're going shopping. Now."

 

They drove to the mall, and Mora led Dan to the Victoria's Secret store. They went to the bra section, and stared at the myriad of sizes, shapes, and colors available.

"Would you like some help?" said the cute salesgirl.

"Yes" said Mora.

"What size are you?" she asked.

"Oh it's not for me. It's for *him*" said Mora, pointing to Dan.

"I see" replied the salesgirl, somewhat suspiciously. It wasn't every day that a man bought a bra for himself, with his wife there to look on!

"Can you fit him for a bra?" said Mora. "I think he's put on some muscle around the chest and in the shoulders, and his other bras aren't fitting as well as they used to."

The girl measured him, and then helped select three different bras. There was also a sale on panties, and they purchased four pairs for Dan, and two for Mora. Lastly, Mora helped Dan to pick out a nightie, and a set of sexy nylons. The salesgirl took them up front, and they rang up the purchase.

Next, Mora led Dan by the hand to The Gap, where they purchased two tank tops for him.

"Can I borrow your tape measure?" asked Mora, to the salesgirl there.

"I can measure you honey" she replied.

"Well, actually it's my husband who needs to be measured" said Mora. "He's looking for a nice skirt."

The girl looked stunned. She had never measured a man to fit into a skirt before. She did it gingerly, and kept her distance as she helped him to select a denim skirt, and a black one. They checked out, then walked to the end of the mall where the department store was located.

"They have the best selection of cosmetics in the place" said Mora.

She made Dan sit down at the counter for Clinique.

"My husband is dissatisfied with his current cosmetics, and he's looking to switch. Can you help him find some colors that are good for his skin tone, while I pick out a purse for him?"

"You want him to wear makeup?" said the lady.

"He already does. I'm just looking to get him into something of a higher quality. And he's no good with colors. You should have seen how his lipstick clashed with his eyeshadow! Help him out, and we'll buy a full set of everything today."

"Very well" said the lady, shaking her head.

Dan had to sit there, as she went through the color charts, and helped him pick out lipstick, lipgloss, eyeshadow, mascara, powders, creams, pencils and a compact for his purse. Mora interrupted twice to show Dan the purses she was considering for him, and to get his input. He was very embarrassed to be in such a spot, but he couldn't argue! It was all to save him from his legal mess.

 

Once they were home, Mora reminded him of something else that Jack had mentioned.

"Go take your bath, and use the lavender bath salts. Then you can shave your legs, your chest, and your armpits."

"Do I really have to do all this?" said Dan, exasperated.

"Yes dear, you do. Or would you rather go to prison?"

"Okay, okay, I'll do it" he said, moping. It had been a terrible day so far. Legal trouble, lawyers, and now all these feminine things he had to buy for himself in public. Shaving his legs was just one more humiliation on top of all that, as was Mora plucking his eyebrows a bit when he got out.

"You smell pretty" she said.

"Gee, thanks" he replied, as he put on his nightie for the first time.

 

 

The next morning, when Dan was getting ready for work, Mora helped him to get dressed. She handed him the red silky panties they had bought the night before.

"But when I go to the men's room, I'll have to sit down to pee! They don't have a fly" protested Dan.

"Big deal. *I* sit down to pee" said Mora. "Get over it."

"But what if someone looks under the stall, and sees that I'm wearing red silky panties?" he said.

"Then we have another witness to help us at trial."

Now she handed him the matching red bra, and helped him put it on. It was padded, so even with a shirt on, it would look like he had tiny little boobs under his shirt. To make matters worse, you could see an outline of the bra, once he had his polo shirt on.

"Remember dear" said Mora, "keep the buttons undone, so that your neckline is as open as possible. When you're sitting at your desk, pull it to one side, so that you're showing just a bit of your bra strap. We need people to see it."

"Do I really have to do this? I'm embarrassed" said Dan.

"Not as embarrassed as you'll be in jail, wearing a uniform, sleeping in the same cell as some criminal!"

"I get your point" sighed Dan.

Mora put just a light hint of makeup on him, then smiled as she checked him out.

"Have a nice day" she said. "Don't forget that we have an appointment at 4:30 for our manicures!"

"How can I forget that?" said Dan.

 

Work was terrible for Dan, and he felt like everyone was staring at him. He heard whispers and giggles as people walked by. They were seeing his bra. He had never felt so embarrassed in all his life. But it *was* better than the alternative.

Nobody sat with him at lunch. And when he got back, someone had left a copy of Cosmo on his desk. He shook his head, and put it into a drawer, out of sight. The last thing he wanted was for his coworkers to all be making fun of him. So it was almost a relief at 4:15, when he got up to leave for the day.

But as he pulled into the strip mall, and walked into the salon to get his nails done, he felt just as embarrassed as before. Mora was already there, and told him that everything was ready.

"We're both getting pedicures and manicures today" she said. "You'll love it!"

Dan sat there as the girl started on his hands, filing, and shaping. Then she led him to another chair, where his feet soaked in hot water, with jets of water like a Jacuzzi streaming onto them. It felt good actually, as did the foot and ankle massage she gave him. But then she started cutting his toenails, filing his calluses, and he felt really funny about it. He shifted uncomfortably in his chair. By now, she must have noticed that he was wearing a bra. He wondered what she thought of him.

Now she took our a bright red nailpolish which Mora had selected, and she painted his toenails. Now he felt *really* intimidated and scared. Anyone seeing his feet would think he was strange. It meant he couldn't work out at the gym and take a shower for example. Or go to the beach barefoot. Somehow, the little bits of red color on his toenails was so intimidating, that it made him feel less of a man.

Back at the first workstation, the girl applied nailpolish to Dan's fingernails. It was a light pink color, barely different from the color of his natural nail beds. At first, he didn't think it might be too bad, but after a second coat, and a clear sealer on the top, he was horrified at how shiny his nails were. The color might not give away the fact that he was wearing nailpolish, but the shine would!

"Thanks, see you next month. Make another appointment for the both of us" said Mora. "We like it here so much, that we're switching to your salon."

"Thank you!" said the girl.

 

Back home, Mora told Dan that it was time for him to put on a skirt and blouse. He went upstairs, and put them on. Mora inspected, but she didn't like something: the way his blouse laid so flat. She used extra socks to stuff his bra, to make it look like he had boobs.

"I'll have to buy you some realistic breast forms" she said. "But this will do for now."

They went downstairs, and Dan pulled the curtains shut.

"What are you doing?" said Mora.

"I don't want people to see me like this!" said Dan.

"Yes you do!" she replied. "They will be witnesses for you, silly. Now open those curtains wide, and lets go out on the back yard so the neighbors can see you."

"You want me to go out like this?" he said.

"No silly" she said. "You need to put on more makeup first."

She sat him down, and start to apply cosmetics to his face. She explained to him what each one was, and how she was putting it on.

"Soon, you'll have to do this for yourself" she said.

She then went to the bedroom, and returned with a box for him.

"I bought you a present" she said.

Dan opened it up, and had a puzzled look on his face.

"It's a hair extension" she said. "You put it on like this, and presto! It looks like you have your hair up in a loose bun."

She put it on, and Dan was horrified when he saw himself in the mirror. He was starting to look more and more like a girl.

 

They went out in back, sat on the porch swing, and talked as they sipped iced tea. Dan noticed how a little of his lipstick came off onto the rim of the glass. It was a different color from Mora's, so you could tell at a glance which glass belonged to which of them.

Their talk was interrupted by the doorbell ringing.

"I'll get it" said Mora, smiling.

She left, and Dan heard her talking to someone. He couldn't wait for her to send whoever it was away. But instead, when he heard footsteps approaching, it was *multiple* people he heard.

"Cindi, Kate, this is my husband Daniella" she said, as two women walked out of the back door.

"Nice to meet you Daniella" said Cindi, who was a tall thin blonde.

"Likewise" said Kate, who was a brunette with short perky hair. "I like your skirt. It's very pretty."

"Thank you" said Dan, as he shot a look that could kill towards Mora. How could she do this, showing him off all dressed up? And she was calling him Daniella! He was outraged. He hadn't known that she was going to do this to him!

"Kate and Cindi are from my golf league" said Mora, "and we've been talking about getting together one of these days. And that just turned out to be today!"

"What a lovely yard" said Cindi.

"I'll give you a tour. Daniella, why don't you go get some iced tea for our guests? We'll meet you in the family room in a few minutes."

Dan refilled his glass, and poured new glasses for Mora's friends. He carried them to the family room on a tray, and felt like he wanted to run away. But they had already seen him dressed up all girly, and there was nothing he could do about it now, but to endure their company. He would talk to Mora about it all later.

 

After hours of chatting, the two ladies were ready to leave.

"I just wanted to tell you Daniella," started Kate, "that I think it is really wonderful that you have such a strong feminine side, and that you aren't afraid to let it show."

"I wish *my* husband would quit all his macho posturing" added Cindi. "It would do him good to spend some time in a skirt, and understand how *I* feel. Maybe some day you can get together with him, and try to convert him?"

"We'll see" said Dan.

The women left, and it was just Dan and Mora alone now.

"Daniella?" he said.

"Yes" she replied. "Your female name. Don't worry honey, I know you must feel terrible, but we really need to do this, so you don't get in trouble with the law."

"But you're making me feel like a woman!" said Dan.

Mora laughed, leaving him standing there speechless.

 

* * *

 

The next few months waiting for trial were no better for Dan. Every day, he wore bras and panties under his clothes at work. At home, most of the time he dressed up in women's clothes. He wore makeup. Went shopping with Mora, buying more and more things for his female wardrobe, which was now stored in the guest room.

He went with Mora when she got her polish change, or her manicure. He was growing his hair longer, and got it styled in a more feminine manner, when Mora got her hair cut. He wore his hair extension most of the time at home, along with women's shoes, nylons, and more and more accessories. He wore a necklace all the time now, and a diamond tennis bracelet, along with several rings. And Mora was talking about having him pierce his ears!

 

When it was finally time for the trial, Mora helped him pick out a new outfit. It was a woman's outfit of course, but one that was somewhat masculine. It was dark blue, with pinstripes. Underneath it all, Dan started out with padded panties, and a new girdle he had bought, which helped to control his tummy, and make it look a little bit like he had curves. Next, he wore his new, realistic looking, C cup sized breast forms glued onto his bare chest.

After putting on his knee high dark nylons, he put on a black corset. It left the tops of his breast forms exposed, while helping to shape him, and push up his fake boobs. Then he put on the pants, which were cut for a woman. They had a very wide belt, with a silver colored buckle in the front, which he fastened as tight as he could stand. Then came the jacket, which clinched in the middle with a single button. It only came to his elbows in the arms, while reaching down to just below his waistline at the bottom. The lapels were thinner than a man's jacket, and the top was opened wide enough to expose a bit of the black corset, and the top of his breast forms.

To compliment it all, he wore pointy toed black shoes, with a moderate heel. Mora made him carry in his new purse, which was small, with a long thin strap to put over his shoulder. He wore his usual compliment of jewelry, makeup, and his hair extension.

Mora had plucked his eyebrows the night before, to make them thinner than they had ever been before. He put on full makeup, and had on diamond stud earrings, since he had finally caved in and gotten his ears pierced. As a final touch, he wore new glasses, which were a style designed for a woman. They were black frames, cut into ovals, and they looked really cute. They helped hide some of the manliness in his face, and he had to admit that once fully dressed, it was the most feminine he had ever looked.

At work over the past few months, Mora had encouraged Dan to be more and more daring in his choice of clothes. He was scared the first time he had worn a blouse into work, or a tank top and blazer. But now, he was used to being seen like that in public, and he didn't blush at it anymore.

Everything was all set for the trial. Dan sat next to Jack, their lawyer, and looked back into the audience for moral support from Mora.

 

The prosecution started out by laying out the evidence. Dan was male. He bought women's clothes, fraudulently charging them to the airlines. The prosecutor made it sound like an open and shut case. But then jack went to work. And what a job he did!

First, he called the salesgirl from Victoria's Secret.

"Ms. Johanson, do you recognize the defendant?"

"Yes sir."

"Where do you recognize him from?"

"The store where I work selling lingerie."

"He buys things there for his wife?"

"No sir. He buys them for himself."

"How can you be so sure?"

"I've fitted him for a bra. Or he came in to complain that one style of bra was irritating to his skin, so we traded it in for a different one. I've seen him wearing bras under his clothes. He is a regular customer."

"What else does he buy?"

"He buys panties, nylons, nighties, slips...all sorts of things."

"Thank you" said Jack.

Now it was time for the prosecution to cross-examine her.

"Ms. Johanson, when was the first time that the defendant bought something from you?"

"About four months ago" she said.

"Four months ago? That was when he was first charged with fraud" said the prosecutor.

"Objection! Is there a question here?" said Jack.

"Withdrawn" said the prosecutor smugly. He had just punched a hole in Jack's legal tactic. Or so he thought.

"Redirect your honor" said Jack. "Tell me, Ms. Johanson, how long have you been working at your present job?"

"Four months" she said.

"And so, the defendant could have been shopping there for years before you started, as far as you know."

"Yes, it's possible" she said.

"No more questions."

Jack had shot down any doubts that the prosecutor had raised. In fact, it had been one of his instructions to Mora, to make sure to find a salesclerk who was new to the store. Now that forethought had paid off.

 

One by one, Jack brought up coworkers who testified that they had seen Dan wearing a bra, a blouse, or women's shoes in the office. He brought up neighbors who saw him cleaning the windows, while wearing a skirt. Then he brought up Mora's friends, who testified about their tea parties.

"And when at these tea parties, what name did the defendant use for himself?" he asked to Cindi.

"He liked for us to call him Daniella" she replied.

"Daniella? Isn't that a woman's name?"

"Yes it is" said Cindi.

"So you drank tea with Daniella, who was wearing a dress, or a skirt every time?"

"That is correct sir" she replied.

 

By the time Jack was done, the closing arguments were very easy. He pointed out that there were dozens of witnesses who had testified that it was common knowledge that Dan dressed up in women's clothes. The prosecutor made a lot of noise and blustering in his closing argument, but he didn't have the evidence on his side. In under an hour, the jury came back with a not-guilty verdict.

Dan hugged Mora. The charges were dropped, and he was free!

 

"That was some performance" said the man from the airlines, wearing his smart three-piece suit. "We think you've been faking things to get out of the charges. We'll be keeping a close eye on you 'Daniella'. If we find out that this is all for show, and you stop dressing as a woman, then you'll find yourself right back here in court, and have to answer to some very serious charges. Airline fraud is one thing. Lying to the court, well that is quite a bit more serious. You'd be looking at considerable jail time if that were to happen."

The man walked away, and Dan stood there stunned. All this dressing like a woman was all supposed to be like a game, to get him out of prison and legal trouble. But now, it was dawning on him: it was going to have to become a way of life. He would *never* be able to go back to being a man, as he used to be.

He turned to Mora, to see what she had to say about it.

"Actually, I'm *glad* that you're going to have to stay as Daniella" she said. "I love you so much honey, but ever since you've become more feminine, you are so much better of a person. I love Dan, but I'm madly in love with Daniella. I hope that you'd consider being 'her' all the time, now that it's all in the open. Everyone knows you're a girl now, so why not go with it full time?"

"You mean, always dress and act as a woman?"

"Yes. I think that you should consider *becoming* Daniella, and leaving 'Dan' in the past. You're a much better person for being so feminine, and I'd hate to see you ever go back to being a man again."

"What are you saying?" asked Dan.

"I think you should consider getting breast implants, so you don't have to wear those breast forms anymore. I think you should go on female hormones, so your body can change even more. I think you should throw out all your man-clothes, and wear your skirts and dresses all the time now. I want you to be my girl, Daniella."

Dan stepped closer to Mora, and gave her a great big kiss.

"If that's what you want" he said.

"Yes. You're my girl now. Lets go, and set you up for an appointment. Who knows, maybe one day soon you can ever get that thing between your legs removed, so that you'll be a *real* woman, all the way."

Dan turned around, he was Dan no more. From then on, he was Daniella.

 

And the all lived happily ever after.

 

The End

  

  

  

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