Nina was visiting her mother in Florida for the weekend, so he was alone. He called, and talked to her mom for fifteen minutes, then to her for an hour. He missed her so much! This was their first time apart for quite a while. He had wanted to travel to Florida with her, but it just didn't work out. But it was only a few days apart.

Andy went out and worked on the garden. Nina had planted flowers, and helped him spruce up the yard. He went out and weeded, fed the roses, and watered everything very well. Satisfied, he went back in for dinner. He used to order pizzas all the time when he was alone, but Nina had him hooked on eating better. He had a salad and a Lean Cuisine for dinner, then sat down with a bowl of lite popcorn to watch a movie.

* * *

The next morning, Andy was getting dressed to go out to the mall. He was going to surprise Nina by buying a new tennis outfit for her. She would be so surprised! They had started taking lessons together, and he thought she would love a cute outfit with one of those little skirts.

He felt so uncomfortable in his pants, so he tried in her jeans. They fit like a glove! He put on one of the tank tops, since it was so hot outside, and drove to the store. He drove around town a little, since it felt so good to cruise around and feel the wind in his face. With the tank top on, he felt cool and comfortable.

Finally, he made it to the store. He picked looked at outfits, and eventually he it narrowed down to two finalists. A white outfit with light blue trim, and a peach colored outfit with white trim. He just couldn't decide, so he just went ahead and bought both. They were so cute! How could he pick just one? The skirts were really nice looking, and the tops had built in bras. She would love them. He paid for them, and drove home.

* * *

On Sunday, Andy didn't have much to do, so he went for a cruise in his car. That really relaxed him, and made the day fly by. In the afternoon, Andy decided to lay out the outfits on the couch, so Nina would see them when she walked in the door that evening. He took them out of the bag, removed the tags, and laid them out carefully. He felt his hand running over the smooth material. They looked so comfortable and so cool. Much better than his heavy shorts and shirt. He wondered how it would feel to wear one? Her jeans fit him so well, so he was the same size as her. Plus, that would make sure these fit her well.

So he took the white outfit back to the bedroom, and put it on. He looked in the mirror, and stared at himself. It *was* such a cute outfit! He loved how the skirt felt. If he wore one on the court, he would feel the air moving under it, instead of the stifling shorts he normally wore. And the top! Without sleeves, it felt so cool! The built-in bra felt very comfortable. He liked having that little bit of support up top. He had lost weight, but he still had some fat to get rid of on his chest. The built in bra would keep him from jiggling as he ran.

He pretend to hit tennis shots, looking at himself in the mirror. He would need to get an outfit like this for himself! It fit so well, and it was so much better than his own outfits.

Nina arrived at 10:30pm, and ran into Andy's arms. They embraced, kissed and held each other tight. She just loved the outfits, and promised to wear one the next time they played.

"Aren't those my shorts?" she asked, looking at Andy's clothes.

"Yes. I put them on by accident, but look how well they fit! They are so much more comfortable than mine. I don't feel so fat in the hips when I wear these."

"They do look good on you, like they are just your size."

"I put them on by accident, and found that they fit me like a glove."

"And that's my top too, isn't it?"

"Yes. My shirts were too long if I wear these. Yours are shorter, and they fit me better anyway."

Nina stared at him for a moment. This was strange, how well he fit into her clothes. But she was tired, so she didn't really want to think about it. She and Andy went to the bedroom, and after making love, they went right to sleep.

* * *

As Andy drove to the customer on Monday morning, he reflected on how much more comfortable he had been over the weekend, when he had drove around in Nina's shorts or jeans. In his pants, he felt so uncomfortable. And neither of them felt as good as wearing the skirt had. He wished there was a way for him to get something so comfortable for himself.

What if he bought a ladies business suit? It would have pants that fit like Nina's did. Perhaps that would be the way to go. Some ladies suits had skirts too. It would be fun to get a suit that had matching separates, so he could mix and match. That might be a good idea. And women's clothes would have more colors available than the drab blues, grays and blacks of the men's suits. He would ask Nina to help him pick out a new suit for himself.

After a whole week of driving to customers, Andy was exhausted. He needed a few days to relax and unwind. He felt really tired. Friday night, he was even too tired to make love with Nina. He took care of her with his tongue, but he couldn't get himself hard. He was just too exhausted.

As they laid in bed, ready to fall asleep, he looked at her body. He felt jealous.

* * *

In the morning, Nina woke up and looked at Andy. He had worked so hard with her at the gym, but his hips just wouldn't get any smaller. He had lost most of his fat, but in his chest, he hadn't lost anything at all. It made it look like he had little breasts. As he lost more and more weight, it made them look larger and larger.

In fact, with his long hair, wide hips, and small breasts, he almost looked like a woman. The fact that he fit in her clothes better than his own had bothered her a little, but now as she stared at his naked body as he slept, she came to the startling conclusion that he almost looked like a woman.

Had he been that way when they first started going out? She didn't think so. This was all her fault, making him lose that weight. She had encouraged him to start exercising with her, and now look at him. He looked more and more like a woman.

But there was something else. His face. It seemed subtly different. She couldn't put her finger on what it was though. She got out of bed and cooked a good breakfast for him. When he joined her in the kitchen, they ate together, then he insisted on doing the dishes so she could go get ready for tennis.

Andy looked at Nina, in her cute peach tennis outfit. He felt so jealous!

"Nina, I have a question for you" he said shyly.

"Sure love, what is it?"

"Well, I've lost so much weight, thanks to you, but up here I haven't" he said, cupping his hands over his small breasts. "I hate how these jiggle when I run. Can I wear one of your sports bras today? That will hold them back, and stop them from jiggling."

"Sure Andy, you can if you want to. But you'll be able to see it under your shirt."

"Oh, I hadn't thought of that. What else can I do?"

"Well, this shirt has a built-in bra" she said. "Why don't we find you one at the store like that? Then it won't be so bad for you."

"We don't have the time. Listen, I'll just wear your white one today."

He went to the bedroom, put on her white top, and sighed. This felt so much better! But it didn't match his shorts at all.

"It would look so much better with the matching skirt" he said out loud.

"True, but do you want to wear a skirt in public?" she said.

"You're right" he sighed as he pulled his hair up into a ponytail, so it wouldn't get in his eyes as he played tennis. "Lets go."

* * *

After tennis, they came home and showered together. Riding in the car, Andy had thought of what Nina had told him about wearing a skirt in public. He had only worn one briefly, in private, and he had loved it. He couldn't get the thought out of his mind now.

Andy watched Nina take a bra out of her drawer, and put it on. He reached in, and grabbed one for himself, and put it on. He was amazed at how bit it made his boobs look, and how it pushed them together, giving him cleavage.

"You look good in a bra" laughed Nina.

"It feels so much better to have some support for them" he replied. "I feel naked without one."

Nina was suddenly worried. He liked wearing a bra? And she had to talk him out of wearing a skirt that morning. Something was seriously wrong. She decided to do something about it. She would try to scare him, and make him stop this, wanting to wear her clothes.

"Here" she said, handing him a pair of panties. He thought nothing of it, and put them on.

"Now lets see....ah, this one will do fine" she said, pulling a purple dress off a hanger. She handed it to him, and he put it on. It had a low cut low cut neck line, plunging down deep, with a cute little bow at the point of the 'v'. The pattern was a very feminine one, with flowers in different sizes, in different shades of purple, lilac and white. The hemline was midway between the knees and the hips, ending in a frilly ruffle. The shoulders puffed up slightly, with loose fitting ruffles and frills as well.

"You look pretty" said Nina.

"Thank you" said Andy. That wasn't what she expected to hear! This was going all wrong!

Andy went over to her shoe rack, and picked out a pair of white pumps, and put them on. They were perfect for that dress. How had he known to pick those? He went to the bathroom to blow-dry his hair. Instead of his usual straight hair, he used her hair products to give it some volume, some fullness, and some styling. His hair looked pretty! Prettier than hers even.

"Can I?" he said, pulling out her makeup kit.

"Knock yourself out babe" she replied. If he was going to do this, then let him do it all the way and get it out of his system. He put on foundation, a little blush, eyeshadow, mascara and lipstick. He sprayed himself with her perfume. He plucked his eyebrows a little! He even went to her jewelry box, and picked out a necklace for himself.

They went to the living room, and he sat on the sofa, with his legs crossed. Nina could not believe what she was seeing. If she had not known any better, she would have sworn that he was a woman. He was radiant! He was pretty! This was so wrong.

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