"Ugh... that's an awkward question I never thought I'd ever be asked by my best friend," he sighed out loud. His face slightly turned red as he answered, "Falsies." He followed her into the closet as she began to examine what he had. "You can try on anything if you like. We're kind of the same size and I could do your make up for you if you want to."

Wow, they seriously sound like a pair of girls, giving each other makeovers or something. "This is super gay..." he thought to himself. There were times when he thought about giving up his secret hobby. But there were other times when he just wanted to go out in public in a dress because he liked feeling feminine. Maybe his sister messed him up in the head when they were younger by making him wear her clothes. He'd always thought he was pretty when he crossdressed and it was kind of thrilling when other people thought he was too. He was a closet crossdresser as he had never told anyone before. Even those he met dressed as a girl had not figured out he was actually a guy yet.

When he thought about it, he and James/Jess made a weird pair. Maybe it was fate that they both had met and decided to be best friends. If so, life has a sick sense of humor. "Well, I'd rather be friends with her and be sick than to be normal and not know her." he decided in his head.

Jess smiled as Nathan offered to let her try on some of the dresses and skirts, even do her makeup. She picked a few cute pieces that she thought would look good together, and furrowed her brow for a moment. She grabbed a dress that came to her thigh as well as a cute denim jacket and made her way to the bathroom. She quickly closed the door behind her and stripped down to her underwear. She wasn't comfortable using her best friend's bra or falsies and had to improvise somehow. The shirt she wore over was thin enough that it should lay flat underneath the dress she was borrowing and large enough that she should be able to stuff it and position it to look right. She expertly tucked her undesirable bits underneath and a small piece of medical tape would keep it in place. She tied her shirt around her chest to hold tissue paper and began stuffing it till it was a large B-cup. She put the dress on and adjusted everything to keep it in place. The were small wrinkles where the makeshift bra sat but it was hardly noticeable. She only just recognised herself in the mirror as she slid the jacket on over the dress and she lightly bit her lower lip.



After taking a second to admire her reflection, she walked back out with a large smile on her face. She had to restrain herself from running at Nathan and hugging him, at speed. She cleared her throat slightly and spoke as clearly as she could, "Hi Nathan, I'm Jessica Alice Reese. I think I'd like to take you up on your offer to do my makeup, if it still stands? And are my nails included?" She asked as she approached her best friend. She wasn't set on it but if Nathan wanted to go out either as himself or as a girl, she was comfortable enough as long as she had Nathan by her side. She hadn't been this confident in a long time.

Nathan took a seat on his bed as he waited for his friend to finish changing. He was a bit anxious, to be honest, but he was also curious. He had spent a lot of his extra money on clothes and his older sister had generously donated a lot of her old clothes, so he had quite the collection in that closet. He wondered what kind of outfit James/Jess would put together.

It kind of took her a bit so Nathan rested on his back and began to flip through Facebook on his phone. But when she finally came out, Nathan did not recognize his friend. She looked pretty cute, and her features were actually quite girlish. He sat back up and gave her a smile as she formally introduced herself to him. "Nice to meet you, Miss Jessica," he said, taking her hand and planting a soft kiss on it. "Whatever you wish, Madamoiselle. Your wish is my command."

He then went inside his closet and pulled out a box that he had filled with make up and the works. He returned back to his room and began to search through the box. "Was there anything you wanted in particular? Or would you like me to surprise you," he asked.

He was rather confident in his abilities to do make up. He has been doing make up for his sister since he was in middle school, since she was bad at it putting it on herself. He also was good at contouring to disguise his more masculine face, not that Jess really needed it since her face was already pretty girly as it was.

Jessica smiled at Nathan's surprised look at her appearance. Did she truly look that different? However when her best friend took her hand so gently and kissed it softly, she couldn't help the intense blush that came to her face. She took a few deep breaths before she sat down on the bed next to Nathan. What would she look like with makeup on? Would anyone recognise her as James Reese? She watched as he agreed and went over to the closet and pulled out a box full of makeup. She took one last deep breath and said, "Surprise me." She shifted to face him more to allow him better access to her face.

She closed her eyes and awaited the instructions on what she needed to do. While waiting she thought back on the sweet innocent little kiss that he had placed on the back of her hand. It clearly wasn't how he was with other girls, so maybe... she didn't want to ask and risk making things awkward, but at the same time she wanted to know. She didn't know exactly what colours Nathan would be using but knowing that his hands would be on her in any way made her feel warm and fuzzy inside. She really had it bad for her best friend and really didn't want to ruin it.

Nathan carefully grabbed Jess by the chin, and began to examine her features more carefully. Once he had figured out what he wanted to do, he grabbed a cool wipe to ensure that her face was clean. Then he picked up the makeup brush and began to lightly powder her face. He started with her forehead then worked his way down her cheek to her chin. Once he was done with the foundation, he reached for the slightly red-tinted blush. He placed some on her cheeks for a rosy, but natural look.

"Close your eyes, and don't open them until I say so," he said softly, as he grabbed the eye shadow kit. He applied some gold, shimmery eye shadow first, then started to add some darker shades of brown and black around the creases of her eyes. Then he added some black eyeliner to polish the look. "Now look up for me please," he said, before applying mascara onto her upper eyelashes. "And now down," he instructed, as he went to apply mascara onto her lower lashes.

For the final touch, he put on some soft pink lipstick. Satisfied with his work, he smiled. "Your makeover is complete, princess. Care to take a look?" he asked. He pulled out a mirror so she was able to look at her reflection. "I hope you like it..."

As Jessica felt Nathan move her head to inspect it, she couldn't help but wonder what he thought would best work for her. Soon she felt the cool wipe wash away any small pieces of dirt and then apply the foundation from the forehead down. Not long after the foundation was complete she felt a light touch on each cheek when Nathan added the blush. When Nathan began instructing her to close her eyes,she knew he meant to keep them closed to keep the makeup out of them. She was enjoying herself and was excited to see what she looked like when Nathan done as Nathan began applying the eye shadow. She wanted to peek so badly by the time the mascara was applied.

When Nathan finished applying the lipstick and told her to open her eyes and tell him if she liked his work, she opened her eyes slowly. Her eyes fell upon her reflection in the mirror and let out a soft gasp in surprise at the young woman she was staring at. She looked nothing like what she was expecting. She wasn't expecting a flawless face to be staring right back at her. Her skin looked as smooth as the calmest lake, with soft pink lips and then there were her eyes. She couldn't help but notice the eyes especially with how amazing the eyeshadow and eyeliner looked. She couldn't believe that the woman she was looking at was her until she reached out toward the mirror and the reflection reached out toward her.

"That's really me? I look amazing! You could probably do this professionally and make more than I do at the diner. I could probably walk up to any of the family and they wouldn't recognise me. Have you ever done that to me?" She asked with a joking accusation. "Thank you for doing this for me." She smiled and gave him a quick kiss on the cheek leaving a slight mark. "Now what kind of nail polish do you have that would work well with your artistry?"

Nathan was relieved that Jess had liked his work. This was his first time doing it on a person that wasn't himself or his sister, so he was actually pretty nervous. And she liked it so much that she planted a simple kiss on his cheek, which was quite unexpected but not necessarily unpleasant. "Hey, I never looked nearly as good as you in a dress," he said, rolling his eyes. "While I do look quite different, I wouldn't have taken the chance to try to fool you. Though I have considered it."

He went through the box and pulled out some different nail polish. "I'm not as good with nail polish as I am with make up. Just letting you know," Nathan warned as he looked through the different colors he had. "I think the glittery, gold one would look nice on you. Or I can do a basic, white French tip. Your choice."

Admittedly, he was having fun in a way that he did not expect. Maybe he should cross dress later after Jess was done with her makeover. But that would be a little too weird... right? Plus, it was way too much work at this point. He would have to take care of the wigs and everything. But it was nice, seeing how excited Jess was. It was hard to believe that less than an hour ago, she was still just James to him. Nathan was determined to ensure that her coming out did not affect their friendship though.

Jessica smiled as her best friend pulled out the nail polish for her. She always enjoyed doing her nails herself and wasn't going to ask Nathan if he wanted to do them for her. Makeup, he went and proved himself and she was likely to ask him to do it for her on occasion in the future but nails were something she'd never ask for from someone else. When Nathan admitted to not being the best at doing nails, she giggled softly, taking the recommended glittery gold polish and grabbing some paper towels that were sitting on the counter. Sitting back down near Nathan she laid the paper towels down to avoid getting the polish anywhere but her nails.

"I don't know. You might have tricked me if you tried, but now I'll know to keep an eye out." She shrugged slightly as she opened the nail polish. "I've had more practice with my nails than anything else makeup wise, so those I can do. The only part of the day I have to do anything is at night just before bed usually, not really any point to putting it on and having to take it right off." Jess explained with a sad smile. She had wanted a day to do this for a long time and she finally got it and got to keep her best friend which certainly boosted her mood as she smirked slightly for a moment. "Do you have any pictures of you dressed up? I'd love to see them." she asked as she slowly and steadily began painting her nails. She smiled as she scrutinised it. It worked really well with the makeup she had on and she began applying it to her other nails. The polish was coming out very smoothly on her nails and it made her smile.

As she finished her left hand nails, Jess looked up and added, "Or perhaps you want to join in?" Part of her was hoping Nathan would agree, the other was very nervous.

Nathan watched as Jess began to paint her nails, using his suggestion of gold. "I didn't really want to risk my best friend finding out that I was a perverted cross dresser," he replied simply. He didn't do it too often anyways. And he did his best to avoid people when he did. It was just the act of walking around in town, dressed as a girl that excited him sometimes. Not that he really knew how to explain it to other people. "Sorry, I don't have any pictures. Too risky." His eyes followed the motion of her brushing the polish onto her nails, rhythmically.

When she suggested that he joined her, he didn't know what to say at first. But then again, why not? "I guess I'll be a blonde this time," he mused to himself, making his way to his closet. He shut the door behind him, but he would still be able to hear her talk if she said anything. He stripped out of his normal clothes and began to put on the lingerie and falsies. "Why am I doing this?" he wondered to himself while adjusting the falsies to fit him more comfortably.

He hadn't cross dressed in a while since he began dating Rachel, so his legs were rather hairy. He opted for a long dress to hide that fact. He slipped on the dress and enjoyed the silky fabric rubbing against his skin. He tied the belt to create an illusion that he had some kind of a waist.



Once he was satisfied with his clothes, he went further back his closet where the wigs were stored on mannequin heads. He had tied the longer strands of his hair back and fixed the hair of a blonde, curly wig. He placed it over his head and pinned it down after adjusting it a little in the mirror.



His face was not yet made up, so he still had a masculine-ish face, but he at least removed his glasses. He took a deep breath and once last glance in the mirror before coming out of the closet. "...I look ridiculous don't I?" he asked as he looked towards his friend.

Jess was surprised when Nathan insisted that she would have noticed that it was him. But what bothered her about his initial statement was that he also insisted that his habit was perverted. It certainly was quirky and different and there were certainly going to be those who didn't understand, but it wasn't perverted, not in her eyes at least. The disappointment that came when Nathan told her that there were no pictures. She could understand, especially given his concerns but she still would have enjoyed seeing pictures of her best friend dressed up. When Nathan got up to enter the closet and get changed, Jess shifted around so she could paint her toenails as well. Her fingernails were dry enough to stay right as long as she was careful not to touch them to anything yet.

She managed to get her left foot done to a satisfactory level and was just starting her right when Nathan came back out. She was awestruck. Nathan was still recognisable behind the dress and wig and chest, but only barely. With makeup, Jessica wasn't sure she would recognise him if she ran into him on the street.

"Wow! You look so beautiful! I mean it's fairly clear you haven't done some of the maintenance work lately, but you look amazing! I'd definitely go on a date with you if you looked like that. Thank you for showing me." She smiled, looking Nathan up and down. "Would you like me to do your nails when I'm done with mine? Or are you going to change back? I'm not going to be offended or anything if that's the case. "

"What? You wouldn't date me with my usual manly charms?" Nathan said, rolling his eyes. He was surprised that Jess had thought that he looked good. While Nathan thought he looked good enough to pass as a girl, 'beautiful' wasn't the word he would have used to describe himself. "I guess I'll stay like this. Why not, right? Let me do my make up first and then you can do my nails," he answered while grabbing his make up kit. He normally liked to go for the standard dark eye make up, long false lashes, and deep red lipstick look. It was feminine and bold; a combination he liked to have when he crossdressed.

He got his contouring kit out and began to work on his face with a brush in one hand and a mirror in his other. Then he put on his powder foundation, did his eye makeup, put on the false lashes and mascara, and finished his look with make up and blush. He had been too focused on his make up to talk but when he was done, he pursed his lips as he looked at his reflection. "Perfect," he said to himself with a smile.

"Call me Nadia," he said with a practiced feminine voice and a wink. "Please take good care of me." He held out his hands to Jess. "We might need to file my nails before we paint them though. Any recommendations on what I should do with them?"

Jessica blushed deeply when Nathan asked if she wouldn't date him with all his manly charms. She didn't know what to say, not without tipping Nathan off that she liked him. She definitely would date him though, but she wasn't ready to tell him that. It would only serve to inflate his ego, but at the same time his apparent self confidence was part of his charm. But with that idea firmly in her head, no thanks to Nathan, she couldn't help but imagine what it could be like. Going out to the movies, going out to dinner together, walking hand in hand, sharing an innocent kiss that becomes something more. If she wasn't flushed before, she certainly was at that point after where her mind went.

Looking back down at her toes, she got back to work on finishing her nails so she could help Nathan with his once he was done with his makeup. It didn't take her all that long to finish her nails and begin rifling through the remaining polishes. She was glancing up at Nathan fairly regularly and was in awe at the difference between his normal self and the beautiful young woman that stood before her. Jessica knew she was pretty beautiful right now but she felt like she barely held a torch to Nathan's beauty at the moment.

When Nathan was finished there was no hint that he was even a guy beyond his height. Nadia was quite beautiful and caused Jess to blush as she looked at her. She heard Nadia tell her that it might be a good idea to file her nails before painting them. Taking a closer look at them, she couldn't help but agree. She grabbed a nail file and methodically began filing the nails until they were smooth and shaped properly. "Okay, Nadia, would you just like French Tips or did you have something in mind for me to do to the nails?"

Nathan... or rather Nadia had smiled as Jess began to shape his nails with a nail file. "French tips work fine," he said, not feeling very picky about it. He was never that into doing his nails, even if it would be for crossdressing. It was a lot of work to put on and to take off. And if you had to let it dry or if you mess up, it gets really sloppy easily. It just wasn't something he was that into. But if Jess was doing it for him, he could trust her to do a good job and all he had to do was make sure he didn't screw it up.

As she began to work on his nails, he casually asked, "Should we hit the town like this? Of course, after I shave. It might be fun." It would be kind of interesting if the two of them went out in public like this. There were times when guys had hit on him because he was dressed like a girl, but he always turned them down. He was also kind of curious if Jess was into guys or girls. Back when she was still "James" to Nathan, she had expressed interests in girls, so maybe she was a lesbian? He wasn't sure how it worked. Would it be too weird to ask her directly? Regardless, he'll probably find out soon enough.

Jessica nodded as Nathan, or rather "Nadia", asked for French tips and quickly pulled out the polish and got to work. "Okay, try not to move your hands so I don't accidentally mess up." She told her best friend and worked as methodically as with herself. Regardless, as she went to move to the next nail, she was surprised to hear Nadia ask if they would like to hit the town after shaving. Jess looked over to the clock on the wall and noticed it was still very early, earlier than she expected. Zoey and Olivia would still be in school and Riley and Sophia would still be at the diner. Meaning that she would have time to stop back at the house and pick up a few things. Her own purse and some spare cash and proper underwear, including her own falsies.

"You know, that actually doesn't sound like to bad an idea. However, if we do, I'd like to stop by my house first, pick up some stuff. Purse, Cash, the right underwear. How much shaving do you need to do? Should I just head out and come back? Or should I just wait for you?" She asked, very nervous to be out on her own for her first time presenting as a girl.

Nathan did his best to keep his hands still as possible so Jess could paint them without any hassle. He watched, impressed by her skills as he never had the patience to really do his nails before. They looked nicer than anything he has ever done to them. He was going to say something along the lines of "Not bad" or "That looks nice", but decided to keep his mouth shut so she could focus. When she had finished, he glanced down at his hand. "Thanks Jess, I'll do my best not to touch anything until they dry," he said. This was the worst part, waiting for them to dry. He was really impatient, and felt restless if he didn't do anything for too long.

To distract himself, he continued on with their conversation about going out. "Yeah, that's a good idea. You should probably just head out and come back," he said after some thought. "It'd probably take about the time you get to your house and back if you leave right now. I have to wait for these to dry too..." He held up his hand carefully to demonstrate. "Where should we even go? The mall? I'm fine with whatever.

When Nadia told her to head home and grab her things, she felt her mouth go dry at the prospect of going back home on public transportation on her own. The town wasn't dangerous nor was the public transportation, but with all the stories she'd heard she was still quite nervous about the situation. Despite her concerns, she managed to work up enough courage based on the fact that she didn't even recognise herself and smiled, standing up. "I think it'll be nice to hit the mall. You already know you can pass, and just going on appearance, I will too, but I still need to know for sure. And if I don't for whatever reason, at least there will be a crowd and stores we can disappear into. Also then we can see a movie if we want. Go get ready, I'll be back." She said with a nervous smile especially toward the end.

She left and quickly made her way to the bus stop, too preoccupied with keeping an eye out for trouble to notice her unintentionally feminine gait. She was glad that she encountered no one on the way or at the bus stop as she sat down on the bench. She knew it would only be a few minutes until the bus arrived and so she began to look over herself. Her nails were almost entirely dry and wouldn't be ruined easily at this point. She carefully grabbed her bus fare from her wallet that was tucked into the makeshift bra. When the bus arrived she was overjoyed to see that it was mostly empty, meaning she was able to board, pay her fare and take a seat without feeling too uncomfortable. Looking out the window as she waited for her stop, she couldn't help but think about how spring weather was finally coming. She daydreamed about herself in a two piece swim suit at the local pool with her family and Nathan. Then the scene in her head changed, she was in the park wearing skinny jeans, a cute t-shirt and a light jacket. Sitting on the grass next to her was Nathan... she shook herself out of the line of thought, she fortunately realised she was coming up on her stop, stood up and walked toward the doorway.

As the bus came to a stop, she stepped off and began walking toward the house. The neighbours would be gone, except possibly officer Richman. That could pose a small problem if he was home and watching. Keeping her eyes open, she made the final turn onto her street and could see that Officer Richman was not home. Relief clearly etched on her face, she hurried to the front door and quickly unlocked it and stepped inside. Knowing exactly where everything was, she quickly glided down the stairs and entered her closet, undoing the makeshift bra and pulling the stuffed tissue out. With a level of ease that would be highly impressive, she grabbed a simple black bra as well as black gaff panties to hide the nuisance and slipped them on without getting fully undressed. After that it was simple for her to slide the falsies into place and adjust them to look right with all the practice she's had. After making sure the adhesive side would stay put (and loving the actual weight on her chest) she grabbed nearly $200 in cash and her purse and a can of pepper spray. That was certainly something she wouldn't leave home without once she was doing this full time. After she double checked to make sure nothing was out of place and that she wasn't forgetting anything, she began walking back to the bus stop, only pausing the lock the door behind her. As she got to the bus stop she pulled out her phone and texted Nathan, Hey I'm on my way back now, how far along are you? Did you lock the door behind me on my way out?

"You'll be fine. I think you should be more worried about getting hit on than getting found out," Nathan assured her with a slightly teasing voice. Though there were truth in his words. No matter how you looked at her, she definitely was a girl. He nodded as a silent goodbye as she went to go back to her place to get her things.

After she had left, Nathan continued to wait for his nails to dry. He didn't want to ruin Jess' hard work so he did his best to be patient. After a few good minutes, he went to the bathroom to shave his legs, arms, and pits. It has been a while since he had did any of this, so it was starting to get a bit hairy and unruly. Nathan sighed. As much as he was really into crossdressing, the maintenance for it was so much work. It took him a while to shave but once he was done, his body was silky smooth. He rubbed his skin gently and was satisfied by the feel of it.

When he went back to his room, he checked his phone and saw that he had gotten a text from Jess. It was a couple of minutes ago so she was probably already almost back. He quickly typed up his response and sent it to her. "I just finished. Also I didn't lock the door so feel free to come right in," he had texted.

He took the time to admire his appearance in the mirror. He looked good... Not as good as Jess and most girls out there, but he still looked pretty good. He ran his fingers through his blonde wig to fix any strands that may look out of place. He pursed his lips and winked at his reflection.

It was rather fortunate that the door wasn't locked as she left. As nervous as she was, she'd rather not be out in public alone as much as possible at the moment. She stepped onto the bus when it pulled up, and immediately noticed how much busier this one was. Not wanting to try her luck with waiting for the next one or walk, she paid the fare and reached for a hand hold near the front of the bus. She tried breathing normally but it felt like everyone was looking at her. Not many actually were, but to her it felt like everything was one step from ending in disaster. So naturally, nothing happened during the entire ride. People got on and people got off, but that was it. The instant she stepped off the bus, she let out a sigh of relief. That small torture was over, and she was back with her best friend, just as soon as she makes it back upstairs.

Quickly making her way back up to her friend's room, she slipped inside and urged herself to calm down. She made it home and back without being discovered. She was almost excited about it and was now more excited about going out with her friend. "Nathan, I'm back. Are you almost ready?"

Nathan heard the door open and close, which he assumed meant that Jess was back. His assumptions were confirmed true when he heard her voice. "Yeah, I'm done," he replied as he grabbed a purse to carry his stuff. He took a look at his friend, who seemed a bit razzled up. Probably because she was out in public for the first time. "So, how was your first time venturing the real world, Jessica?" he asked with a teasing smile.

He motioned for Jess to follow him out of his room and walked out of his apartment. After they were out, Nathan locked his apartment door and made his way to the bus stop. "Sorry you have to take the bus so much," he half-joked. "Maybe we should invest in a car... or at least a bike."

Eventually after waiting for the bus, getting on the bus, and getting off the bus again, they were at the mall. The ride was pretty uneventful aside from maybe a few looks they had received from a group of guys. In case Jess was nervous, Nathan had assured her by saying, "Don't worry. They just think we're hot... which we are so..."

They entered the mall in all its wonderful, vast glory. "So, dah'ling. What would you like to do first?" he asked with an overly dramatic gesture. He saw another guy staring at him and gave him a playful wink. The man blushed slightly and quickly walked away. "This is why this is way too much fun to quite," he thought to himself.

Jess smiled as Nathan came into view and was ecstatic that he was ready to go. "It was a little nerve wracking at first, but having survived, I think it won't be so bad this time," She answered as she took a few deep breaths to try to visibly calm down. 'Over thinking things will only cause you to accidentally out yourself. Relax and everything will be fine.' She told herself as she followed Nathan out to the bus stop, where he apologised for having to take the bus so often, and suggested investing in a car or at least a bike. This admittedly caught her off guard, and she turned to face Nathan.

"Invest in a car? Together? How would... how would that work?" She asked. One of the first things she thought was that he was taking a round about way of asking her to move in to avoid awkwardness with her family and share the car. She'd still have to tell them eventually and if she were being honest with herself knew that it would be better to say something sooner than later.

When she got on the bus with "Nadia", she couldn't help but notice how much busier the bus was than earlier and all the eyes that were on them. She had to remind her to breathe several times before they got back off. Several of the guys who were looking were pretty hot, but she was too nervous to talk to them, but she smiled at them and looked away. As they got off "Nadia" reassured her that the only reason people, especially guys, were looking was because they were hot. And they were, at least that's what she would tell herself if she weren't being so self conscious. She was quickly distracted however by her best friend asking her what she wanted to do first. "I don't know, why don't we go look around for a bit." she suggested, somewhat unsure of herself.