Nervous Preparation

Nichole started her Saturday with a feeling of frustration. All week long she had been looking forward to spending time with Jacey. When he had reached out to her on Friday to confirm their date for Sunday, Nichole had been happy. It was shortly after that when the frustration had started to set in. She realized that she didn't have a plan for their time together.

Having lunch and watching movies together were nice date activities, Nichole freely admitted to herself. The problem wasn't with that. She was frustrated because she didn't know how she was going to get Jacey to... fully appear? To come out and play? The boy was sweet, and Nichole enjoyed talking with him, but she wanted Jacey, the feminine, cute girlfriend to spend time with her.

Since she hadn't needed it last time, Nichole felt confident that she could use the 'oops' attack to get Jacey to shower and put on the pajamas again. She was sure it would work, but that wasn't what she wanted. The last time, Jacey had played along so perfectly that Nichole wanted more of that. She was hoping that she could get him to go ahead and shower with only a little pushing. It shouldn't be hard, since he road a bicycle to get around. A shower to freshen up, because they were going to be so close to each other to do makeup just made sense.

Nichole realized that she was going to be creating a problem for herself. Jacey was smart, a person that could think and plan if given the chance. It would not take long for him to plan ahead for taking a shower at her house, and that would probably mean he would bring a change of clothes of his own. Nichole had to get him, not just used to the idea, but looking forward to it, to being dressed in women's underwear and clothes, before he got into the habit of bringing extra boy clothes with him.

Nichole didn't have anything against boys. She even thought boy Jacey was kind of cute. She just got excited at the thought of helping Jacey develop as a girl. It also fit her personal tastes better. There were plenty of men that wanted a woman like Nichole to take charge and dominate them, but that was not attractive to her. In her mind, the man had to be dominant, and a woman should only be dominant over a younger woman. They were old fashion ideas, she knew. But she liked the idea of a man in charge, and a woman being in charge of pleasing the man, and in charge of teaching the younger woman how to please.

Nichole also didn't want to be too dominant with Jacey for fear of chasing him off. She knew she had to lead him more than push him in the direction she wanted him to go. This brought her back to her current frustration. How to get Jacey to dress up as a girl on Sunday.

Nichole had actually been thinking about the problem all week. On Monday it had just been a question in her mind. A question that would float around as she sorted through her oldest clothes and accessories. Some of the things she had been wearing early in her own transition had been tossed out, or passed on to other beginners she had wanted to give a little help and encouragement to. Wednesday evening, Nichole had finally just gone out to buy some things for Jacey, and herself as long as she was shopping. Now she had a little section in her closet just for Jacey's things.

Nichole may have been getting ahead of herself, but she was having fun. Jacey didn't know it, but she now had a flirty sun dress, a light blue blouse with a short, dark blue skirt, a sexy black babydoll nightgown, and a must-have little black, short sleeved dress. There was a space reserved for shoes, once Nichole was able to take her shopping in public. Nichole had also picked up a cheep plastic set of drawers and put them in Jacey's section of the closet for underwear and accessories.

Nichole was getting ahead of herself with the shopping, but she was more frustrated by how she was forced to hold back. Everything she had bought so far had been in general sizes. Things like bras and shoes needed to be tried on, to make sure of the size and fit. And until she knew what Jacey's base bra size and other measurements were, she couldn't shop for anything more than just generic pads to help with shaping to fill out her clothes.

While considering the question of how to get Jacey into properly feminine underwear and clothing, without finding a good solution, Nichole did come up with a plan for 'makeup lesson' part of Jacey's visit. The idea came from trying to think of a way to keep Jacey from being put off by feminine clothes and looking sexy, or from how to help her look feminine and sexy in spite of masculine clothes. The answer was to work on gender neutral makeup, and then gender bending looks, such as the pretty man or the rugged woman.

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Looking back, Nichole realized that the problem had been that she had too much time to think about what she was hoping to do. She had given herself time to worry she had not had the weekend before. Because she had time to plan, and to worry, Nichole had everything ready for Jacey's visit hours ahead of time. That left her with free time to fill with anticipation and worry, so she decided to have a glass of wine. She was working on her third glass when Jacey arrived.

X

Jason had left his home early, as he had the weekend before. The only things he had done differently was how he had packed his bag for the day, and how directly he had headed towards Nichole's house. He had gone to her neighborhood first thing, and from there he had found a place to sit with his school books for a few hours. He wanted the distraction, and was afraid of the loss of freedom that would come with any drop in his grades. His parents didn't seem to notice when he kept solid A's and B's, but he was sure they would come down on him for any C's or below.

Even with the distraction, it had proven hard for him to wait. He ended up spending twenty minutes riding his bicycle around to burn off some of her nervous energy. He had made sure of his personal grooming before setting out that morning, so he would look clean, but was also hoping for another shower when he arrived. Right at 10 o'clock he dismounted from his bike in Nichole's driveway and started for her door.

It didn't take Nichole long to answer her door. Once again she was dressed in comfortable clothes. This time a loose pair of light gray sweat pants and a dark gray sweatshirt that was cut to show her waist and had the collar cut out to make for a cleavage displaying vee-neck, and the sleeves were cut off just above the elbows.

"Jacey," Nichole greeted him with a bright smile and a wine glass in her hand. "Come on in. I am glad you came."

"Thank you for inviting me," Jason said politely as he entered.

Nichole closed the door, then reached around him in a loose, single arm hug. She held him just close enough to be able to give him a kiss, her lips pressed against his for little more than a second.

"May I use your shower?" Jason rushed to ask before she could suggest that he needed one. He wanted to show that he was civilized and housebroken enough to be welcome in her home.

"Go right ahead," Nichole smiled in happy agreement to his request. "I set out some clothes for you already, if you want to wear them."

"Thank you."

Jason made his way to the master bathroom as calmly as he could. He closed the door carefully and started the shower before dropping his bag and undressing. He kept the shower short, to keep as much time free for anything else that Nichole might have in mind. Once out of the shower and dried off, he opened his bag and pulled out the things he had hidden under his school books.

Laid out on the counter for him were the clothes Nichole had mentioned. He saw the pajamas from last weekend neatly folded next to a pair of denim shorts and button up plaid shirt with short sleeves. He thought about his choices carefully. Remembering how things had gone before made the pajamas tempting, but seeing that Nichole had another choice laid out made him suspect that he had something planned out, and he didn't want to disappoint her. As an added benefit, Nichole's offerings of clothing would work well for the surprise for her he had packed.

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Out in the kitchen, Nichole had finished her glass of wine, and had laid out a healthy snack for Jacey and herself. She was just pouring the iced tea when Jacey appeared around the corner. Nichole felt her heart flutter with excitement at what she saw.

Jacey had clearly taken her lessons to heart. She was wearing the shirt and shorts that had been left out, including the belt. The shirt had been long in the torso, so Jacey had tucked it in to the shorts that were at least one size too big for her young hips. They were held in place by the belt cinched snugly around the waist, helping to create the illusion of fuller hips. But what really made Nichole excited was that Jacey had done her own hair and makeup.

"Oh, Jacey, you look fantastic," Nichole set the iced tea down and moved to embrace her guest.

"Thank you," Jacey accepted the praise and the hug, thankful for the snug panties under the short that were keeping a sudden erection at least partially restrained. And while he was enjoying the feeling her body against his own, he still pulled his head back a bit to protect his makeup.

"Let me take a look at you," Nichole shifted her hold on Jacey so she could examine the makeup work.

"I decided to practice, and this is the look I knew best," Jacey said with some embarrassment.

"You did a wonderful job of it," Nichole praised him. "You are a quick study." Even through the makeup, she could tell Jacey was blushing, because his ears were turning red. "Well, let's have a little snack. You can tell me what you did last week, and then we'll start on a new makeup lesson."

"Alright," Jacey nodded. And that is what they did.

Jacey told Nichole about how he had acquired his beginning makeup kit, and mentioned raiding the boxes in the garage for old clothes that nobody would miss that he could use for costume parts. He talked about his trial and error applications, and even brought out his phone to show Nichole some of the less successful makeup jobs, along with his first solo recreation of his feminine look.

Nichole listened attentively as they shared a snack tray of sliced vegetables and an assortment of dips. She looked at the offered pictures and made a gave some constructive advice. Mostly reassuring Jacey that she would just have to practice in order to get used to things like layering and shading.

"It took me a little while," Nichole took charge of the conversation as the snack was nearly empty. "But I finally settled on a lesson plan for today. That is why I put out those old clothes." She did not admit that she had spent hours going to, and going through, three different thrift stores to find just the right 'old clothes' in order to 'just happen have them around' for Jacey to use. "We are going to work on gender illusions, from androgynous out to hyper masculine and feminine."

"Huh?" Jacey blinked.

"After we clean up here, let's go to the bathroom and I'll show you what I mean."