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Mistaken Intentions

by Jennifer White

 

From the first time he met her, Matt was in love with Sarah. She was beautiful. She was smart. She was athletic. She was funny, adventurous, kind, gentle, graceful, and more. In short, she was everything he had ever dreamed of in a woman, and with all his heart, he wanted to be with her. In fact, she was so perfect, that she was god to him. He even prayed to her at night, hoping she'd hear his voice.

But there was one, ever so tiny problem: when he met her, it was because she was dating his best friend. That didn't deter Matt, he was bound and determined to have her at any costs. Best friend or not, he'd steal her away. But first he had to get to know her better, and let her naturally fall in love with him.

There was a close knit group of friends that hung out together. Five of them were in couples, but Matt was alone. There were some other friends that would join the group from time to time, but it was normally the same people going to each other's houses to party, going out to dinner together, and spending a lot of time as a group.

When the groups of friends got together, Matt would hang out with the girls, where Sarah was. He would drink wine with the girls, instead of doing beer and shots with the guys. Instead of getting wild with them, he'd listen to the girls talking about their babies, their relationships, their houses, and their lives. And that made some of the girls start to wonder.

 

* * *

 

"I wonder why Matt isn't dating anyone" said Nancy one day, as the five girls had lunch together, taking a break from their shopping trip. Nancy was short, but very well built, and very attractive. She was the newest to the group, and knew him the least.

"He seems more comfortable around us when we party, than he does the guys" noted Elsa, who had short hair, and deep eyes.

"He likes drinking wine with us, instead of beer with the guys" said Sarah, her long blonde hair gleaming in the sunlight.

"He borrowed some of my 'chick lit' books when he was over at our house last week" said Elsa. "Most guys don't read that!"

As they discussed the way he acted, they all wondered aloud if he really thought of himself as one of them. And they came up with a plan, to try and gently make him decide.

 

* * *

 

"A wine tasting party?" said Matt.

"That's right. At my house, on Friday night" said Elsa. "Everyone brings a bottle, we all have a glass, and write down our notes. The best rated wine wins. But don't go crazy and spend too much on your bottle."

"Okay" replied Matt. "That sounds fun. I'll see you there."

"Cool. Later" said Elsa, hanging up.

"He's going to come?" asked Sarah.

"Yes. He'll be there. Then we can find out" replied Elsa.

"Well, we have a lot of work to do. Lets get ready girls" said Sarah.

The girls all smiled. They were looking forward to Friday.

 

* * *

 

Matt arrived at Elsa's house. It was a nice one story white house, with big windows in the front. He rang the doorbell, and walked in. They were all friends, and they all felt like they could just walk into each other's houses, although it was nice to ring the bell first to let them know someone was entering.

He stepped inside and looked around. He saw Nancy placing glasses at the table. Emma had a tray of hot appetizers that she was setting out on a platter. He could hear Elsa and Sarah talking, off in the kitchen, while Debbi was pouring water into glasses on the table.

"Hi" said Matt.

"Hey!" said Elsa, as she walked out from the kitchen.

"Um, where's Terry? Where are the guys?" said Matt, looking puzzled.

"The wine party is only for girls" replied Elsa as she smiled warmly. She wasn't taunting him; she was just making him understand that he was welcome and accepted in their company, even though he was the only guy. Matt's thoughts raced as the implications set in. They were accepting him as one of their own.

Elsa studied Matt's face after she informed him. She was looking for subtle signs which might betray what he was feeling. If he thought of himself as one of the girls, there should be no problem. But if he was just a lonely guy in desperate need for female attention, being told that he was "one of the girls" should have sent off warning signs inside. He should have protested, or tried to excuse himself. But his calm face showed no such signs. Elsa looked at Sarah. They gave each other a subtle nod. Their ploy would continue.

Each of the girls was under strict orders to treat Matt as if he was a girl. They were to act as if there were no guys present at all, and just be their normal selves. Sarah and Elsa would take the lead in keeping an eye on Matt, looking for signs that would indicate how he felt inside. They would try to draw it out of him, but they didn't want to move too fast, and scare him off. An operation like this didn't need male bluntness; it would take special nurturing care and the subtle maneuverings, which could only be pulled off by a woman.

They started out by doing what women do when they're together: they talked! Sometimes as a group, and sometimes one on one, but it was a whir of conversation as everyone seemed to be talking at once. Elsa and Sarah had decided that if he was thrown into a situation where he could observe how they all acted, he could understand what to do if he wanted to fit in. If he was silent and just sat there, they'd know he was going into "man mode". But if he took part of the conversations, he was trying to be one of them. It was another subtle test, as well as a chance to let him learn how to act as a woman, if he truly wanted to become one (whether he realized it or not!).

Matt noticed how one thing was different than with the guys: if the guys had organized something (like a beer tasting party!), as soon as everyone arrived, they'd be ready to start drinking. But with the girls, the wine party was the excuse to get together; it wasn't the focus of why they were there. He saw how much they enjoyed all the gabbing they were doing. It struck him that this was the true reason for them to meet up. He also noticed that while it sometimes seemed chaotic, when one of the girls was speaking about something important to her, the others really seemed to listen, whereas the guys always interrupted each other. This was such a different, gentler way to converse!

Finally, they got to the wine tasting part of the party. They took sips of different wines, and wrote down their comments and opinions. Then they discussed the results as a group. There were no winners, no losers, just a good time. And unlike the guys who drank hard, trying to out-do each other, the girls only seemed to drink enough to have fun. They weren't in it to get trashed. Matt shuddered as he thought about what could happen to a woman if she over-did it. Someone could take advantage of her. It was with good reason that they were being moderate!

He was really enjoying himself. Not only was he getting a tremendous amount of female attention, he was hanging out with his beloved Sarah. He tried not to stare at her, but she made his heart leap. She was the one. He wanted to be with her more than anything in the whole world. He would have done anything to be with her. And now his heart raced, because she sat down beside him!

"Are you having fun?" she asked as she smiled at him.

"Yes" he said. "This has been just great."

"We're going to do something else now, and I wanted to ask if you wanted to join in, or if you thought it was time to go home."

He didn't want to leave! Not now. He was desperate to stay with Sarah, and to prove his love for her. This evening had been one of the best nights of his life. He didn't want for it to end.

"We're going to sit down now" said Sarah, "And we're going to paint each other's nails. Don't feel like you have to do this. Only if you want to. Nobody will be upset, or think less of you if you go home now."

Matt's mind raced. Paint his nails? Not only had they asked him to an all-girl event, but now Sarah was asking if he wanted his nails painted!

"Would you be doing it?" he asked her. He longed to feel the touch of her hand on his.

"If you want" she said. "And then you can paint mine for me."

Matt's mind raced. He'd never had an opportunity to get so intimate with Sarah before! How could he refuse?

"Then I'll say yes" he replied.

 

Sarah smiled warmly, as she nodded her head to him.

"I'm glad you're so open to new things. This is going to be fun! Come over to the table, and we'll help you pick out a color."

She took Matt by the hand, making his heart leap for joy. She sat him down at the table, where the girls were digging through piles of little jars, trying to find a cool color to try out. Everyone smiled at him kindly, as he joined in.

"I think you should go with a light pink" offered Elsa. "That way it won't be so noticeable. Try this one."

"Thanks" said Matt, as Elsa grinned at him.

For a moment, he had been afraid that this was some sort of trick, and that they'd make fun of him. But he completely trusted Sarah. He loved and worshiped her. She was like god to him. She would never betray him. But he wasn't as sure of some of the others. But nobody teased him. In fact, they all seemed happy that he was joining in.

Emma sat down with Elsa, Nancy with Debbi. It was only then that Matt noticed that none of the girls had nail polish on. They had planned on doing this all along. Sarah sat down at the table across from Matt, their knees almost touching. He stared at her long blonde hair, and her glowing perfect face, mesmerized. She was touching his hand!

"Lets start with your right hand" she said. "I'll explain what I'm doing, so when it's your turn, you can do my nails."

"Okay" said Matt, somewhat sheepishly, as Sarah dipped the brush into the nail polish, wiped off the excess on the top of the bottle, and applied the first brush stroke onto the nail of his pinkie. He felt a mixture of emotions as she gently explained what she was doing, and how she was doing it. It was shocking to see nail polish on his fingers, something he had never done before. It was so alien to have such a feminine thing done to him. But at the same time, he felt a mellow buzz from the wine, and an almost euphoric high from having Sarah hold his hand, as he sat so close to her.

For most men, having their nails done would have triggered the innate fear that males have of all things feminine. Most men would have felt the primal urge to get away from the women. Most men would have felt like they were being manipulated or controlled. All these things would make an ordinary man want to flee. But between Matt's overwhelming feelings of love and attraction for Sarah, along with the closeness he felt with her at the moment, and the fact that alcohol can lower one's inhibitions, Matt felt none of the typical male reactions. Instead, he was overwhelmed with pleasure. He felt so good as she moved on from his right hand to his left! He was in heaven, as she painted his nails.

"You have nice nails" she told him. "Fred's are all rough, but I can tell that you take care of yours."

"Thanks" he replied, feeling even more elated at her giving him a compliment. And one showing that he was better than her boyfriend too!

"Have you ever gone to get a manicure?" she asked.

"No" he said.

"You should try it sometime. I think you'd like it."

If she said he'd like it, then he knew he would. He put 'manicure' on his inner to-do list. Sarah wanted him to try one. And she had said she was glad that he was open to trying new things. He'd show her how right she was. He desperately wanted to please her, to show her that she should be with him.

Now it was Matt's turn to do Sarah's nails.

"I'll go with the same color you picked out. I like your taste in nailpolish."

"Thank you" he said, blushing. His hand was unsteady and trembling a bit, as he began. She kept talking to him as he worked carefully, trying his best to do as good of a job on her, as she had done on him. He held her hand, and applied the polish to her nails. Unlike his short nails, hers were longer, and nice filed into perfect ovals.

"Now our nails are the same" said Sarah, after Matt completed the last nail.

"Yes" he replied. It felt so strange to have this kind of closeness to her, to be like her in a way he had never imagined.

"Your nails look so pretty" continued Sarah. "But when I look at your face, it seems kind of plain. Can I do your makeup?"

"You mean..." said Matt, his voice trailing off.

"I mean I want to put just a little makeup on your face, so it can be pretty too. Nothing drastic. Just a little. Would you like it if I did your makeup for you, Matt?"

It was something that Elsa and Sarah had talked about at length. If he allowed her to do his nails, then they would test the waters further, and see if he was willing to wear makeup too. If so, they would know that he either already knew he was a woman on the inside, or else he was just discovering, and wanted to explore further. They decided that if he was a true man inside, he would reject the offer, and want to stop before they took him any further.

Matt started at Sarah, noting the light makeup that she wore. Just a little color on the lips and the cheeks, and something on her eyes. She wanted to put some on him. She wanted him to look pretty, like her. How could he ever say 'no' the woman who he looked at as god? How could he turn down a chance to have her close to him, touching him? There was only one option for Matt.

"Okay" he told Sarah. "Go ahead."

Sarah smiled gently. She took out a pouch that contained all sorts of makeup, and she went to work on Matt's face. True to her word, she kept things minimal, adding just a hint of color. Elsa brought a mirror so Matt could see what Sarah was applying, and all of the girls offered hints and tips on how they did their own makeup. Everyone made such a fuss over him, he felt overwhelmed with all the attention. But mostly, he could feel the warmth of Sarah's body, she was so close. Her hands were touching him! He was overjoyed, as the woman who was his god spent so much time with him, being so close and so friendly.

When Matt's makeup was done, everyone told him how wonderful he looked. They were all so kind to him.

"I like your face like that" said Elsa.

"Me too" added Emma. "Your eyes look so nice."

"Thanks" he said, blushing. "Sarah should get the credit. She did all the hard work."

"But it's your face looking so pretty" said Sarah, as she smiled at him again.

For the next hour, the girls all had one more glass of wine, and talked up a storm. As far as they were concerned, Matt was one of the girls now too, and they treated him no differently than they would any other girlfriend. But then at last Matt's wonderful night had to come to a close. One by one, everyone got ready to leave. Matt felt sad as he walked back to his car, although he was still talking to his beloved Sarah as he got in.

"Thanks for everything" he told her.

"Not a problem" she replied. "I had a good time tonight too."

"Good night" he said.

"Good night" she replied sweetly.

Matt drove home, feeling like he was floating on air. He didn't even think about the fact that he was out in public, wearing makeup, and polish on his nails. If the police had pulled him over, it would have been quite a difficult thing for him to handle! But he made it home without incident, and went right to bed after saying his prayers of thanks to Sarah. His head filled with the most wonderful dreams, all night long....

 

* * *

 

"You were so right about Matt" said Sarah into the phone, as she moved a pan onto the stove.

"I couldn't believe it when he let you paint his nails like that" said Elsa. Her tone wasn't scornful; there was no sense of ridicule in her voice. It was just a casual observation.

"And he seemed to enjoy it when I did his makeup" added Sarah. "He seemed so relaxed around us."

"He never freaked out about anything. Even when we told him it was a 'girls only' night."

Sarah stirred the soup in the pot on the stove, then shifted the phone to her other ear, as she wiped up a little bit that had dripped out.

"Well, I guess we should move on with the plan" said Sarah.

"Definitely" replied Elsa. "He seemed so happy. This will be for his own good."

"Are you going to call him, or should I?"

"I'll call him right now. You can do the shopping."

"Sounds good. Give my love to Terry. I'll see you tomorrow."

"Great. Bye-bye!"

 

* * *

 

Matt was eating his dinner of reheated pizza, when the phone rang.

"Hello?" he said, hoping it wasn't yet another solicitor calling to sell him something.

"Hi Matt, it's Elsa" said the cheery female voice on the phone.

"Elsa! How are you doing?"

"I'm wonderful. How about you?"

"I'm doing just fine" he replied.

"Did you enjoy the wine party?" asked Elsa.

"Oh yes. I had such a wonderful time" said Matt.

"I'm glad you did. How did you feel, being with just the girls."

"It felt awesome" he said. "I felt like I was glowing all night."

He didn't dare tell her that he was glowing because he was so close with Sarah. How could he tell Elsa that he was madly in love with her good friend? Just the thought of having spent so much time with her made him feel good all over again.

"Next week on Friday, the girls want to get together again. The guys are all going to see the game."

"Oh? They didn't ask me."

"That's because you're with us. Right?"

Another chance to spend time with the girls like before? Matt's heart leapt. He would be with Sarah again!

"Right" he replied. "I'm with you."

"Great. Listen. We take turns hosting. All the girls would like to come to your house. Is that okay?"

"Sure" said Matt.

"Great! So next Friday, 7:30. We'll see you then."

"Thank you so much" said Matt, as he hung up the phone. Sarah was coming to his house! He'd get to spend quality time with her, away from her boyfriend, and in his very own house. What a wonderful night it would be. Just Matt, the girls, and of course her. He looked around, and realized he had a lot of cleaning to do. Girls were fussy about things like that. He would make sure everything was just right for them, when they came over...

 

* * *

 

On Thursday night, Matt was putting some finishing touches on his place, having cleaned it carefully so it would be presentable for the girls. He was just putting the vacuum back into the hall closet, when the doorbell rang. He opened it, and his eyes almost bugged out of his head when he saw who it was. Sarah!

"Hello" he said. "I was just cleaning to get ready for tomorrow. Would you like to come in?"

"Just for a minute" said Sarah. "I have a lot of errands to attend to."

She walked in, holding a large red shopping bag, which she put on the table.

"So, what do you think?" he asked.

"It looks nicer than last time I was here" she said, nodding her head. "But if it was my party, I'd do a few more things."

"Like what?" asked Matt, wondering what he had missed.

"Well, I'd probably get some fresh cut flowers, and put them in a vase on the table there. And I'd get some nice scented candles, and set them around here, and here. Maybe a tray here with some nuts or candies. And I'd get some more flowers for the window over there."

"Wow, great ideas" said Matt, as he scribbled it down in a note. If that was what Sarah liked, he'd be sure to set things up that way. But now his attention turned to the shopping bag she had carried in.

"I bought a few things for you" she said.

"You did?" he asked. "Wow, thanks!"

"Don't mention it" she replied. "Don't take it wrong, but your wardrobe needs a little bit of an upgrade. You kind of stood out when you hung out with us at the wine party, because of how you dressed. I bought you a few things that will help you fit in better. You don't have to wear the outfit if you don't feel comfortable in fancier clothes, but I think you'd look great in it."

"Let me see it" said Matt, somewhat excited that she had bought him something, but also nervous that it was something he might not feel comfortable wearing. Why all the drama about it?

Sarah opened the bag, and first removed a white garment. It was a blouse, with frilly cuffs and lacy trim, along with embroidered white flowers. She laid it out on the table, then pulled out a pair of pants. But they weren't like any that Matt had ever worn before; they were women's pants. They were cropped style, and would only come down half way between his ankles and his knees. There was also a pair of shoes, black with a silver buckle, and just a slight bit of a heel.

"The top is a little transparent, so you'll need a layer Beneath it" said Sarah, as she pulled a lacy white cami top out of the bag. Lastly, there was a pair of white cotton panties, again all lacy and frilly. She smiled at Matt, and waited to see his reaction. These weren't just clothes, they were women's clothes. And she wanted him to wear them for the party!

"If this is too much, I'll take it back" she said. "You don't have to wear what I bought you if you don't want to."

The last thing that Matt wanted to do was to say 'no' to her in any way, or to insult her choice of clothing.

"They're just fine" he said. "I'll wear them for tomorrow."

"I'm so glad that you're willing to be open to things like this" said Sarah. "Oh, and I put together a little makeup kit for you. I just bought some things, and they gave me some free samples. I bought you some nail polish too. The same kind you wore at the wine party. Now you're all set. You've got a good start to your collection."

"Thank you so much" said Matt, who was so excited that she would buy something for him! He hated to see her leave, but she said she needed to run. He didn't shut the door or turn away until her car had driven out of sight down the road. Then he locked the door, closed the curtains, and turned his attention to the clothes that she had bought him.

"She wants me to dress up like a girl" said Matt out loud, as he touched the soft fabrics, and felt the lacy trim. He decided to go and try everything on for size, and see how ridiculous he felt in it all. He went to his bedroom and changed into the new outfit. He felt really strange as he put it on. Never before had he worn women's clothes. But at the same time, he felt so aroused that he got as hard as a rock. These were clothes that Sarah had bought, for him. She had selected them! He felt so excited by it all.

Matt went and looked in the mirror. He felt kind of ridiculous in such an outfit, but he decided that maybe it wouldn't seem so bad if he had the makeup on. He knew he'd need practice, so he tried to put it on himself. He had to laugh at the results, which were less than optimal! Putting on makeup wasn't as easy as the girls all made it look!

Looking in the mirror, a couple of other things seemed very wrong. First of all, his legs. The part of his lower legs that you could see was full of hair, which looked so out of place. He shuddered as he realized that he was going to have to shave his legs, if he was to look presentable. And then there was the hair on his chest. Above the 'v' of the cami, there was a lot of dark hair on his chest, which showed right through the sheer fabric of the blouse. He was going to have to get rid of that too, so he wouldn't look like a fool.

And so Matt carefully removed all of his new clothes, and hung them up. Then he started the shower, jumped in, and shaved all of the hair off his legs, followed by his chest. He decided he might as well do it all, and he did under his arms too, while he was at it. Now, his entire body was hairless. He dried off, and got ready for bed. He had a lot of work to do the next day, to prepare for the girls coming over.

 

* * *

 

Matt left work early on Friday. There was much to be done! He first went to a florist, and picked up a couple dozen carnations, and a dozen roses. Lacking vases at home, he bought a pair of them too. He also found a couple of candles there, which included a holder, since he didn't own any candlesticks (what single guy ever did?). Then he went home, did some final cleaning, and set the flowers out, along with the candles.

Then it was off to the bedroom to put on the outfit that Sarah had bought him. He slipped on the cami and the white lacy panties, and immediately, he got as hard as a rock. He didn't want to be embarrassed in front of the girls, so he hurried off to the bathroom to "relieve" himself, so he wouldn't get hard again for a while.

Then he put on the blouse, followed by the pants. He slipped the shoes on his feet, and it felt funny to be standing at a bit of a slant, from the little heels on them! He walked into the bathroom, took out the makeup that Sarah had given him, and he went to work on his face. He applied a light coat of foundation, followed by some blush. He was careful not to use too much, or to get too much on the brush, as he had done the night before.

Then he put a little color around his eyes, followed by eyeliner and mascara. He put some sparkly pink lip gloss on, and a puff of perfume from the sampler bottle that Sarah had given him. Satisfied that he had done a much better job this time, he went back out to the kitchen, where he put on his nail polish, just like last time he was with the girls.

Now he was fully dressed up in women's clothes, including makeup! He paced nervously. What would the girls say when they arrived? He was so scared of being taunted! When the doorbell rang, he could feel it in his stomach, as fear coursed through his body. He turned to see Sarah walking the door, and all of his worries instantly melted away.

"Look at you!" she gushed. "You look so pretty!"

"As do you" said Matt, as he noted Sarah's tight top that showed off her impressive breasts, along with her short black skirt that gave him a good look at her long legs, which sat atop shoes with six inch heels. He had never seen her dressed so sexy before, as if she was going out on a date! She was here, alone with him, dressed like that. All of his worries about how he was dressed, just melted away. He was in heaven, with his god, Sarah.

Soon, Emma arrived with a tray of goodies, followed by Elsa and Nichole, who arrived together. When Diane (who lived the furthest away) finally showed up, the group was complete. All of the girls. They all gushed over Matt, telling him how pretty he looked, and how wonderful his clothes were. However, he again stood out from the others.

Elsa was wearing a plaid length skirt, and a white tank top. Emma had on a revealing top and a full red skirt, while Diane had on a black cami and a miniskirt. Only Matt wore pants. Only Matt was flat-chested. He noted how all of the other girls had one far more makeup than he did. They all had on high heels. They all had long hair. Although his outfit was all women's clothes, he was by far the least feminine of the group.

It didn't occur to him that they all might be dressing like that so that he wouldn't feel bad about what he wore. Or that they might be doing it to show him an even more feminine style of clothes. But there was also the real reason: Sarah and Elsa had decided to test him, to see if he felt an attraction to them. All of the girls were going to be on the lookout to see if Matt started at their boobs, or if he seemed like he wanted to make a move on any of them.

During their conversations, they all talked about how much they wanted sex with a man who could really please them. They all complained about how their boyfriends didn't do what they wanted in bed, and how they felt shortchanged. Matt was thankful that nobody pressed him about the topic; they let his silence go. He didn't realize that they were trying to get him going, to see what he would do.

But all night long, although they talked, watched a movie, had drinks, and talked some more, Matt never made a move on any of them. Of course, he was so in love with Sarah, that she was the only one he could possibly make a move on. And with the other girls there, he didn't feel like he could even try something with her. And so, he held back, waiting for the right time.

Elsa winked at Sarah, when she saw that Matt did nothing, even when she sat so that he could get a look up her skirt if he wanted to. He averted his eyes, which told her what she needed to know: Matt wasn't after pussy. He thought of himself as a woman. She looked around his house, as the fresh flowers, and the candles. Yes, he must have wanted to be a woman. That was the only possible reason he could be acting the way he was.

 

* * *

 

It was about two weeks later when the next "all girl" event was planned. Matt didn't have to be told that it would be at his place. He wouldn't want to go out of his house dressed up in full makeup and clothes that Sarah had given him. So the girls would be coming to see him. The day before they were due to arrive, he was cleaning again. This time, he had already bought new flowers, so Sarah would be pleased with him.

Almost as if on schedule, she showed up as he was dusting the shelves, carrying another shopping bag. She made some small talk with Matt, and complimented him on how nice the place was looking with all of the flowers.

"Of course, if this was my place, I'd look at replacing those old curtains. Maybe something white and lacy would work. Same for that old tablecloth of yours. I saw one on sale in the paper the other day. Its white, with lace trim. It would help lighten up things in here."

Matt took mental notes. When the girls arrived tomorrow, he would be sure to have new curtains and the table cloth in place to impress Sarah with how well he listened to her, and how much he valued her advice. He watched as Sarah lifted up the bag, and placed it on the table.

"That looks heavy" he said.

"Yes" she replied. "There are a couple of things in here for you."

"Oh? What did you buy me this time?"

"Some accessories. I also put some of my old clothes in here, which I don't wear anymore. I hope you don't mind wearing something used" said Sarah.

Something that she had worn? Matt felt excited and honored to be able to put on something of hers!

"I've got to run" said Sarah, who still hadn't opened the bag.

"You're not going to show me what you bought?" asked Matt, sounding somewhat disappointed.

"You'll figure it out" she replied, giving him a wink, as she turned to go.

Matt wondered why she was so hesitant to show him the contents of the bag. It only made him more curious about what was inside. He watched her drive off, and only when she was out of sight did he finally go to the bag and open it up. On the top were several items of clothes, the used one's that Sarah used to wear.

First, there was an off-white sweater with long arms and a v-neck. It has been loose on her, but it would be tight on Matt. He held it, thinking how it had been wrapped around her arms and her torso, as he wished that he was. The sweater had touched her. He thought about how lucky it (the sweater) was! And how he was going to get to wear it. It made him tingle all over.

Next, there was a black skirt. He held it up to his waist, and saw that the hem line would fall down around his knees. A skirt! Sarah wanted him to wear one now. He realized that at the last party, he was the only one not wearing one. She was just trying to make him feel more included. He put down the skirt on top of the sweater, and looked in the bag to see what was next.

It was a shoe box. He opened it up, and looked inside. There, he found a pair of boots with high heels. He looked at the size, and realized that Sarah must have gone out and found a pair that would fit him. They would go wonderfully with the outfit she just gave him. He put the shoe box down, and dug further to see what was in the bag.

The next item he found was another box. He opened it up and discovered a bra and thong panty set. From the little bit of wear, he could tell that they were used. These were the undergarments that had been touching her. The bra had gently cupped Sarah's perfect breasts, supporting them, and shaping them. And the panties had been there, right over her pussy. Just touching these things sent shivers through him. He was going to wear the things that had touched her private areas!

Now there were two more boxes. He opened the larger one, which was the lighter of the two. Inside, he found a wig! It had medium length hair, that would come down to about his shoulder. It was about the same color as his, but slightly curly. When he put the wig on, it would make his face look better, just like the other girls, with long locks flowing down around it. He nodded, and put the wig back in the box.

There was just one box left. It was by far the heaviest box of all, and had accounted for most of the weight in the bag. Matt wondered what in the world it could be. He opened it up, and gasped when he saw what was inside. It looked like a pair of boobs, large round and full, including a realistic looking nipple on the top.

The box was labeled as "D-cup breast forms", and it included a card that explained how to use them, as well as how to care for them and clean them. Fake breasts, to fill out the bra that Sarah had given him to wear. She wanted him to look like he had boobs, just like all of the other girls. This was going to be hard to do. But he realized that with his flat chest, he would look so different from the others. He took a deep breath. This was just something he was going to have to do.

Matt put all of his new things away in his bedroom, then went back to cleaning. There was much work to do, and he couldn't stop right now to think about breasts.

 

* * *

 

It was just one hour before the party was going to start. Matt looked at the new lace curtains, and the new tablecloth that he had bought, based on Sarah's suggestions. She had been right; it did liven up the room and make things look brighter. He grabbed the wall as he teetered a bit, unsure of his footing in the high heel boots. All day, he had been wearing them around the house, trying to get used to walking in them. He was getting better, but he still stumbled a bit from time to time.

Now he went to the bedroom. Time to get ready. Already, he had Sarah's bra and panties on, having decided that if he wore them all day, it would help him get used to how they felt. The bra felt strange, with its constricting straps over his shoulder and the tight band around his chest. And the feeling of wearing a thong was totally alien for him too. At least he wouldn't have any pantylines when he put the skirt on!

And speaking of which, it was time to take off his T-shirt and jeans, and put on the rest of Sarah's things. It would be like a holy experience for him, to be wearing the clothes that she wore. But first there was one difficult thing to do: he removed the breast forms from their box, and inserted them into his bra. He shuddered as he looked in the mirror.

Instead of the bra cups hanging empty in front of him, they were now filled to capacity, stretching the bra even further. It seemed to make the band around him pull tighter to keep them in place. And with the weight in the cups, the straps of his bra now dug into his shoulders more, making him even more aware of the feeling of wearing one.

But the weirdest feeling was to look down and to see mounds on his chest, the same size and shape as Sarah. Her boobs had always been something that attracted him. Now he had the same thing on him. He quickly went to put on the sweater, so that he wouldn't think about his new breasts so much.

But wearing a tight sweater just made things worse. Ever since he was in school, and the girls started to develop breasts, the look of them in a tight sweater had been exciting. Now he saw the same thing in the mirror, which caused him to get hard again. Just as last time, he was afraid of embarrassing himself by getting hard in front of the girls. And with a skirt on, it would be far more noticeable. So he hurried off to the bathroom so he could stroke himself until he came. Now he'd be small and soft when the girls came.

After replacing his panties, he pulled on Sarah's skirt, and zipped it up in back, with a little bit of difficulty. Her waist was definitely smaller than his! He decided that he was going to need something else first: a girdle. Knowing that the skirt might be too small for him, he had bought one while he was out shopping. He put it on, and felt yet another strange constricting feeling, as the girdle worked to flatten his tummy and make his waist smaller, making it look like he had curves.

Now the skirt fit on better. But as he moved, he could feel it swishing on his smooth bare legs, which was something so different than anything he had experienced before. The skirt came down to just below his knees, leaving two inches of skin exposed between the hemline and the top of his boots. As he looked in the mirror, he shuddered. If a girl with boobs like his, dressed as he was, came into the room, he'd feel attracted to her. To see himself and feel the attraction a man has for a woman was quite disturbing.

But these were Sarah's clothes he was in. She had worn this skirt before. She had worn the sweater. He was in her underwear. That calmed him down, and made him feel better, as he went to put on his makeup. He had already painted his nails, and he had practiced doing his face several times since the last party. He did it much better, particularly around his eyes, which looked sultry now.

There was one final touch: the wig. Matt put it on, and looked in the mirror. He just kept staring: it looked like a girl staring back at him. He had been almost completely transformed. Now he looked like one of the girls.

Matt's thoughts were interrupted by the doorbell ringing. He took a deep breath, and walked into the livingroom, his heels clicking on the hardwood floors. He smiled when he saw Elsa standing there, looking prettier than ever. She was smiling at him.

"Look at you!" she said, like a mother fawning over a daughter all dressed up for the prom. "Turn around! Let me see you!"

Matt twirled around for her. She came up to him and gave him a big hug.

"How does it make you feel inside?" she asked. "Do you like it?"

"Yes" replied Matt. "I feel.... special."

"Special. Yes. You are special, dear."

Their conversation was interrupted by Emma and Debbi, who had driven together. They too made a big fuss over Matt, and complimented him on his look, as did Nancy when she showed up a few minutes later. All that was left was for Sarah to arrive. Matt kept looking to the door, waiting for his beloved to show up.

Finally, Sarah made her entrance. She looked like a perfect angel to him, as she walked in the room. This day, she wore tight jeans with heels, along with a tight black sweater. Her face was glowing as she smiled.

"Wow" she said to Matt. "You're even prettier than I am!"

"I wouldn't go that far" he replied, blushing.

Everyone started talking, as Matt poured them all drinks.

"You've become quite the hostess" said Elsa, which made everyone laugh in appreciation.

"Seriously though," started Sarah, "I have a question for you. Now that you're with us, as one of the girls, I just don't feel right in calling you 'Matt' anymore. Its like you've left him behind. I think you need a name that suits you better."

"A girl's name" said Emma, helpfully.

Matt started at them. They wanted to call him be a female name now too?

"I don't know..." he said.

"How about Lisa?" asked Debbi.

"That's my sister's name" said Sarah. "And you've really been like a sister me lately."

Her sister? Sarah thought of him as a sister? He wanted to be her lover, not her sister. But now he had a special closeness to her that he never had before. She seemed to want him to take 'Lisa' as a name. How could he deny her?

"Okay" he said. "You can call me Lisa."

"I'm so happy for you, Lisa" said Elsa.

"Me too" added Sarah. "It's so great to see you looking so happy now."

Matt was happy. He was with Sarah.

 

* * *

 

 

Hanging out with the girls was becoming a regular thing for Matt. In fact, sometimes if they were in the area, each of them would stop by and say hello. If he got a phone call asking for Lisa, he'd know one of the girls was on the way. He'd hurry to put on something appropriate before they arrived. He had been online shopping, picking up a larger and larger wardrobe of clothes for "Lisa".

In addition, the girls would all give him things they no longer wore. One week, Elsa gave Matt a pink outfit of hers, including a tight sweater and a pleated skirt.

"I'd love it if you wore it to the wine party tomorrow" she said.

"For you, anything" he replied.

The next day when the girls came over, he was looking ultra-fminine in his new pink outfit, with pink heels, extra makeup and even jewelry now. He was growing his hair longer, but he still needed the wig for now. Even his nails were longer now, not quite like Sarah's, but definitely longer than before.

After talking and drinking wine for hours, Matt was seated next to Sarah on the couch, talking about her first pet, a little dog named Sue. As they talked, Elsa stood up.

"Everyone" she said, causing a silence to fall over the room. "I have an announcement to make. Terry and I are getting married."

"That is so wonderful!" said Emma.

Soon everyone was making a fuss over him, and of course this called for another round of drinks. As Matt was in the kitchen opening another bottle of wine, he heard the doorbell ring. All the girls were already there. This was somebody else. He froze, as he heard male voices. It was the guys!

"I invited them over to join the party" said Elsa, as she and Terry walked into the kitchen to help with the drinks.

"Hey Lisa" said Terry, as if he was used to seeing Matt as a girl.

"Hi" he replied sheepishly.

"Do you want a man to help you with that bottle?" he offered.

"Sure" said Matt, who's hands were trembling from the shock and fear of having the guys see him dressed as a girl.

Matt wasn't sure what to do, but Elsa was helpful as ever.

"Lets go talk to the guys" she said. "They're all excited about the announcement too."

She led Matt by the hand into the livingroom. There were all of his friends. They could all see him dressed up as a girl! He blushed, and got ready for everyone to tease him and make fun of him. But something strange happened: nobody blinked an eye. They all said hi to him, then returned to their conversations, as if it was normal for them to see him like that.

"You told them?" he said to Sarah.

"Yes" she said. "They're all happy for you too, that you've found your true self. Everyone here is your friend. Just relax. I can see that you're sweating. Take a seat, have a drink, and just have fun. This is the hardest part, your public debut. Everything is going to be all right Lisa. We're all here to support you."

"Thank you" said Matt, as he sat down, crossing his legs like the girls all did. There was quite a buzz, as everyone talked about Terry and Elsa being engaged. He wasn't even the center of attention. The guys all acted as if they were used to him being a girl. He had such mixed feelings. They accepted him as a girl so easily. And Sarah said this was his true self. She thought that he was really a girl on the inside. Her. The one he called god. She wanted him to be a girl. Something stirred inside him. For the first time, he wondered if he really was a girl inside. Could he really have such a strong inner feminine side, that it was his true self?

Matt had to excuse himself to go use the rest room. All of the wine was getting to him. He sat down to pee, since he had the skirt on, and he was afraid of getting some on it if he stood up. Then he looked in the mirror at his face. Was he really a girl inside?

He washed his hands, and opened the door. Elsa was standing there, waiting for him.

"Can we talk in private?" she asked.

"Sure" he said, leading her to his room. There, she sat on the bed, and patted the spot next to her, indicating for him to sit down next to her. She smiled sweetly as he sat down and crossed his legs.

"Lisa" she said, "I just wanted to say I'm sorry that we surprised you like this, having the guys just come over. I wanted everybody to be here, since we were announcing our engagement. I hope you weren't upset about the guys being here."

"When I heard them, I thought I was going to be humiliated and embarrassed" said Matt. "But everyone has been so kind to me. Sarah told me that you've all told your guys, and prepared them."

"Yes" she said. "The funny thing was that some of them weren't surprised. But they're all happy for you. Sarah says you've really found your true self. Look how well you've taken to being a girl! I think of you as a close female friend. And that's why I wanted to speak to you now."

"Yes?" asked Matt, unsure of where she was going.

"I know that today is your first time letting someone other than the girls all see the real you. And I know that you'd have a hard time going out in public. But because I value you as a friend so much, I really want you to be a part of my wedding party. I'd like for you to be one of my bridesmaids."

Matt was stunned. A bridesmaid? Him?

"If you're not ready, I'll understand. I'll get Terry to put you on his side of the aisle. You can go wearing a tux, and pretend to be a man, if that makes you more comfortable. You don't have to give me an answer today. Think about it. But I'd love to have you as a bridesmaid."

"I'm honored" said Matt. "I just don't know...."

"Think about it" said Elsa. "You can tell me next week. We have months until the wedding. Now lets go back out there and celebrate!"

"Its your special day" said Matt. "Come on girl. Lets party!"

They went back out into the group, and for a while, Matt was happy again, being close to Sarah.

 

* * *

 

In the end, Matt decided that he wasn't ready to be in a wedding party as a bridesmaid. Just as she promised, Elsa arranged it so that he would stand up on Terry's side, as a groomsman. By the time the wedding arrived, he was nervous putting on his tux with the other guys. They all thought of him as a girl now. What would they think as they all dressed together? He didn't want them of course, he wanted Sarah. But did they realize that he only went for girls?

His hair was much longer now, almost reaching his shoulders. He pulled it back and styled it as manly as possible. As he put on his bow tie, he felt somewhat embarrassed that he had plucked his eyebrows so much that you could really tell, even though he was in men's clothes. He had removed his nail polish, but his fingernails were far longer than the other guys.

The ceremony was wonderful, with Elsa looking prefect as the beautiful bride. The party was a blast too. The guys were all together drinking, which gave Matt an opportunity to hang out with Sarah most of the night. He drink with her, talked and laughed. It was one of the best nights of his life, with Sarah almost all to himself.

But then Sarah's boyfriend Fred came over, and asked her to dance. She smiled to Matt, stood up, and went onto the dance floor with her man. Matt felt crushed. His Sarah had just left him, to be with another man. He was so heartbroken that he felt that he would cry. She was the one. With all his heart, he loved her.

"If I can't have her, I'll never have anyone" he said to himself, as he wiped his eyes to keep them dry.

 

* * *

 

Matt put on his new little black dress, and went to work styling his long hair. It was longer than Sarah's now, falling down well below his shoulders. He loved how full and wavy it was. He pulled on his pumps, and went to the kitchen to check on the cake in the oven. It was just about done, so he waited for it so he could take it out of the oven.

He could see the soft skin of his face in the reflection from the metal. Ever since he had started using the creams, his skin had become much softer. He could see his earrings dangling down, swaying as he moved. They matched the pendant he wore around his neck. He wanted the party this day to be perfect. Sarah had told him that she had something special to share with the group.

When everyone arrived, Matt had everything ready. Drinks for all, except for Elsa who was pregnant now (he had a wonderful time at her baby shower). Little snacks and appetizers. Candles lit. Fresh flowers all over the newly redecorated livingroom. He was quite the hostess. It was all for Sarah still. If she wanted a special day, he'd give it to her.

The girls all came with their guys. Sarah had her sister Lisa with her too. The real Lisa. No matter; he'd make sure Sarah's sister had a good time too. He'd just have to be careful if someone said 'Lisa'!

Once everyone arrived, after some drinks and some food, Sarah stood up along with her boyfriend Fred.

"We have some news" he said.

"We're engaged!" she said, holding up her hand so that everyone could see the huge diamond he had bought her.

The girls all came over and gave her a hug. Matt did too, although he felt like someone had just punched him in the stomach. He knew this day would come, but he pretended it never would. He was about to lose her forever. She would belong to another man. If he didn't have her, he'd never have anyone.

"You're crying" said Sarah.

"Tears of joy for you" he lied.

Almost the same way that Elsa had, Sarah took Matt aside to have a talk in private talk. And in a manner that was eerily similar to Elsa, she too had a question for him.

"I've been so happy for you, now that you've found yourself" said Sarah. "I think of you like a sister. You are one of my closest girlfriends. I mean.. you even share my clothes. I'm asking my sister Lisa to be my maid of honor. But I'd like for you, Lisa, to be in my wedding party. Will you be one of my bridesmaids?"

Matt did not hesitate to answer. What Sarah wanted, Sarah got. Plus, if he couldn't have her, he'd never have anybody. It didn't matter anymore if people saw him as a woman. He was happier that way anyhow; he could be more like Sarah, and feel closer to her. In a flash, he realized that for the rest of his life, he would remain female. The old Matt was gone, dead and buried. He had become Lisa.

"Of course I will!" he said, smiling. "I would be honored to stand up for you."

"I'm so glad you'll do it" said Sarah, giving him a hug. "We have a very special friendship, and it won't end, just because I'm going to be married to Fred."

"I know" replied Matt. "I'm so happy for you. You're like a sister to me too. I can't wait to see what you'll look like in your gown!"

"Me too' she replied. "I'm going shopping next weekend. Elsa is going to come with me. Do you want to join us?"

"Sure!" said Matt, as he wiped a tear from his eye. This time, it really was a tear of joy.

 

* * *

 

On the day that Sarah went to pick out her gown, Elsa showed up at Matt's house. He was dressed up in a nice outfit with a white blouse, length navy blue skirt, and matching blazer. He had a purse over his arm, full of everything he might need.

"Are you ready?" he said. "Do you want to drive, or should I?"

"Lisa!" exclaimed Elsa. "You want to go out like that? You don't want to change into men's things first?"

"Men's things?" said Matt. "I don't have any of those anymore. I cleaned out my closet, and gave it all to the poor."

"Really?" said Elsa, surprised.

"Yes. I finally took the big step. From now on, even in public, I'm going to let everyone know that I'm a girl. Think how surprised they'll be in the office on Monday when I show up in my new pants suit!"

He seemed genuinely excited about it, which made Elsa smile. Matt really was a woman inside, she decided. She took him by the hand, and led him to her car. They chatted as they drove to the bridal boutique, where Sarah was already looking at dresses. Elsa and Matt helped her pick out a few that were 'her'. She modeled them, drawing applause from Matt and Elsa, until she picked out just the right one.

"Now for the hard part" she said. "The bridesmaid dresses."

"No velvet!" said Elsa. "And no peach! I want something I can wear again."

After an hour, they still weren't sure what to get, so they took a catalog, and promised to return the following week. Then the three drove to a restaurant where they could dine together, and have a drink. Elsa had her baby weeks before, so she was able to drink with them again. As they sat in their booth in the corner, Elsa eyed the guys at the bar.

"What do you think of him?" she asked Matt, pointing to the one at the end.

"He's okay, I guess" he replied.

"He's yummy" said Sarah.

"You're engaged darling" said Elsa. "You're off the market my dear."

"A girl can still look" she said.

Then Sarah turned to Matt.

"Are you going to bring a guy with you to my wedding?" she asked.

"No, I don't think so" he replied.

"All of the other girls are" said Elsa.

"No, not for me" he said, looking down.

"You say that like you don't want a man" said Elsa.

Matt just nodded, sadly. Sarah and Elsa looked at each other. They had wondered if he was attracted to men. But even though he seemed perfectly suited to live as a woman, and he had committed to dressing as one full time, he still didn't want a man. They thought that was strange, but it didn't bother them. Whatever made their friend happy was fine with them. They quickly changed the conversation on to happier topics, and the three had a great time.

 

* * *

 

Sarah's wedding day was a special day for Matt too. Ever since he had committed to being a girl full time, he had been taking herbal supplements like black cohosh to put some plant based estrogen-like substances into his body. But now he found a doctor, and got a prescription for the real thing. He waited until Sarah's wedding day to take his first dose. He would be on the path to true womanhood now.

The day of the wedding, he accompanied the girls to the salon. The all got their hair done up in fancy French braids. Then they had their nails done, in a color that complimented their gowns. They all had their makeup professionally done. And then they put on their bridesmaid gowns. Sarah had chosen a strapless gown, shiny powder blue, with short sleeves and matching gloves. Matt put his on, along with the other girls. For all intents and purposes, he was one of them now, in every way (but one, between the legs).

He arrived in a limo with the other girls, to the church. The girls all congregated together, talking nervously as they waited for the signal to line up to start down the aisle. Matt got in line behind Lisa and Elsa. When the wedding director signaled, he stepped forward. Fred's brother Carl was paired up with him; he took Carl by the arm, and walked down the aisle, until the reached the altar. Then he turned to the bride's side, and stood next to Elsa, waiting for the other girls to join them.

Then at last the bride herself: Sarah in the most beautiful gown that Matt had ever seen. It was all he could do to hold back tears. Tears of joy for her happiness, but also tears of sorrow, knowing that he was about to lose her forever. He felt no fear or embarrassment of being a bridesmaid. He was a girl now, and everyone thought of him as such.

The wedding party was wonderful, except for when he had to dance one song with Carl. He had read that once he started taking estrogen heavily, he might start to develop feelings for men. He didn't care. If he did, he did. The moment that Sarah said "I do", he decided that he was going to go all the way, and get "the operation", so that he could be like her, in every way.

Before the end of the party, Sarah took Matt aside in the hallway.

"I have something for you" she said.

"Really?" he asked, excitedly.

"Yes" she said. "I'm going to try and get pregnant, right away. I have a six month supply of birth control pills here, as well as some that Elsa had left over. They're full of female hormones. I'll keep my prescription, if you run out and want more. I thought that you might want to start taking these."

"Sarah, thank you so much" said Matt, as he accepted the bag. "I have something to tell you. Today, I took my first estrogen pill. My doctor said that after a year of living like this, they can proceed with my operation. I'm going to become a real girl. Just like you. I wanted you to know that I look at you as my role model. You're like god to me. You are so perfect in every way. I am so happy that you're happy, and you've found the one you love. At one time, I had hoped it would be me. I'll never have you, so I'm going to do the next best thing, and become just like you. You're like a sister to me, and more. I love you, and I always will. When I adopt a baby, I'm going to name her after you."

Sarah was taken aback.

"I don't quite know what to say" she said.

"You don't have to say anything. Just go out and enjoy your special day. Don't worry about me. I'll be just fine. I've found true happiness as a woman, and it is all thanks to you. Instead of being a miserable lonely man, now I'm a happy woman, with lots of friends, and so much to look forward to. When you think of me, I hope it will be as a female. I'm going to become just like you Sarah, in every way. You've made me so happy with the time we've spent together. You're my best friend in all the world. I love you. Like a sister."

Sarah and Matt hugged.

"I was worried you'd be upset today" she said. "I knew you cared for me. I just never realized how much."

"I care for you enough that I want you to be happy. Your man is waiting for you. Go to him. I can't wait to see the pictures from your honeymoon when you get back! Get busy sister. I can't wait to see my niece or nephew nine months from now."

For the first and only time in her life, Sarah gave Matt a kiss on the lips. He stood there, savoring the feeling, as she turned and walked away. He stared at her flowing bridal gown.

"Some day, I will be a bride" he vowed, as she returned to the crowd. He clutched the bag full of birth control pills. They contained many powerful female hormones, which would help him in his transition to womanhood. He wasn't a man anymore. He wasn't Matt. He was a she now. And she was Lisa.

Lisa opened up the dispenser, and removed one pink pill. She gulped it down, and returned the dispense into the bag. She imagined that she could feel the hormones already absorbing into her bloodstream, altering her body and mind. She was going to be a woman. She took the bag back to her table, and set it down. Then she went and stood with the other "wallflower" girls, looking for guys to dance with.

  

  

  

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2007 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.