The Ballad of Natalie and Chloe(Andrew) Chapter 1&2

The Ballad of Natalie and Chloe(Andrew) Chapter 1&2

Author's Note: I hope everyone enjoy me trying to write more of a happy story and thank you all for the help and support.

Chapter one

Walking down the street Andrew could feel everyone was looking at him. He wished that looking was all that the strangers were doing. Everyone he walked by either was staring, leering, ogling , or even pointing and laughing at him. He hated the snickering the most but kept his head up as he made his way to keep his meeting.

He arrived at the coffee shop with ten minutes to spare. He always made it a point to be early but it was vital for this meeting. This was for if he was late, the lady he was meeting with would have left right away. She warned him that for the first meeting there was no excuse for him being late. It will be cancelled and only if his explanation to her was satisfactory she would reschedule on her terms.

Meeting the terms for this meeting was hard enough, Andrew did not know if he could go through trying to meet her again with even more stipulations. Most people would have found the non negotiable term he agreed to for this meeting as unrealistic and the lady who made them as uncaring about others, not Andrew. He fully understood that Natalie was just protecting herself.

While waiting for the lady who scheduled this meeting, Andy nervously stood in the entrance of the coffee shop fidgeting with everything in his full hands. He was carrying his wallet, cell phone, pack of cigarettes, lighter and keys for his pockets were for decoration and not functional. He was hoping that he has not been catfished.

This young man has open up about his secret to this lady and now had doubts that she was ever sincere. The uncertainty came from the ridicule he heard from all the other patrons of the shop. He knew that all of the conversations in the cafe went from whatever they were talking about to him. He cannot blame them with what he has on. He would have done the same thing if someone else came into here looking like him..

He started to look around to try to see if when a burnette which fit the description the lady gave him walked up to him. She was dressed in jeans and t-shirt. She was walking towards him with a grin while inspecting what his outfit. Andrew thought “This must be Natalie.”

Natalie was a woman in her early thirties with short raven black hair in a short bob. She was cute, not beautiful and carried herself in a willful manner. Her style was elegant, even in t-shirt and jeans she comes off as posh. She had a certain charm, charisma, which grabbed the attention of any room she was in, even if it was a chat room.

Natalie greeted him by kissing him on his cheek. He turned red for how much more attention it drew onto him. She then commended him on being early and instructed him to join her at the table she pointed to. He greeted her back,,thank her for the compliment and acknowledged he was going to the table.

He waited for Natalie to be seated first and she motioned for him to sit. Natalie said “Sweetie, you sit dear. It is improper for the ladies in the group not to be seated first.”

Andrew went to apologize for what he believed was a perceived faux pas and Natalie immediately stopped him when she said “Darling it is fine, you are not used to being the woman in this situation.”

Andy notice that she has not used his name yet while talking to him. She called him sweetie or darling. That is nothing new for she never called him Andy or Andrew referred to him in anything which can construed as masculine. He actually liked that.

With how Andrew kept playing with his keys, Natalie knew he was nervous. The wooer wanted her potential love interest to calm down and she reached under the table to get the gift bag she has brought to give him. “Sweetie, I thought that you might had not realized that you would need a handbag so I picked one up for you”

The bearer of gift gave the bag to her friend and instructed him to open it. It was a nice simple black handbag. Andrew was really touched by the gift and thank the giver. Natalie said “Honey, you are welcome. I thought that you might not even of thought of how much you would need a handbag, for you are accustomed to being able to fit everything you need in your pockets.”

Getting the gift and hearing his suitor reassuring words in a gentle tone relaxed Andy. He told her he never realized how tight pockets are on women shorts. He then excused himself to get a drink. Natalie stopped him by putting her hand and his and said “Honey, I will get you your drink, you have and want the woman role in our friendship. We are both interested in each other and me having the man’s role I should get you your drink and I should had offer to do so before you even mention you were going to get a drink. Sorry this is also new to me.”

Andrew smiled; he knew the experince was also new for Natalie.The male who wanted to be the female in a relationship understood they both were going to stumble along as they found how to fill the roles which they both wanted. He gave his potential boyfriend his order “An Iced tea with some nutrasweet would be great!

On her way get the drink she told him to put his things in his purse and think about why he picked the outfit. As he was filling his purse he thought about why he was wearing what he had on. He knew his answer has to be truthful and full of details. It has to meet her approval for her to stay after hearing it. That put pressure on him, but Andy knew he can handle it.

When he is honest with her she rewards him with her presence. The few times he was dishonest and said what he thought she wanted to hear the cost was her withdrawing until he told her the truth. She understood why he would do that sometimes, but told him that she expects it to happen less and less.

As Natalie waited in line she was thinking of how this first face to face encounter with Andrew was going. She knew that it was a little uncomfortable for both of them and she blamed herself. The nervous lady needed to be more relax and open up to that great person she was spending time with today. It was just hard for the lady who did not have lady luck when it came to romance.

Natalie always had a thing for effeminate men and only wanted to date them. She did not want to treat it as a fetish for she also wanted a close personal connection with whoever she was with. She always ended up meeting with guys who were not right for her. Like the late middle aged divorcee who claimed to be female and lived alone yet did not and would not dress, the married man who wife did not know about his true gender, the guy who only wanted to be the woman in the bedroom, or young man who wanted to be punished for expressing what the searcher of true love thought was the best part of who he was. They were not bad people, they just led her on and she was not going to be burn again. They wanted someone to act out their fantasy and Natalie was looking for the real thing, an everlasting love.

The lady who wanted somebody special to share the rest of her life knew that she needed to be more at ease. So far she saw so much potential with Andrew. The boy who wanted to become a lady was just starting the journey but he was so strong and determined to be who he should had been. Not only is there potential but when she let her guard down they both felt the chemistry while talking online, just think what it will be like in person. She started to tell herself she was not going to blow this.

Natalie got the tea and felt lighthearted after assessing the situation between those two and the little pep talk she gave herself. His date body language being more open made Andrew feel more easy going and he started right away to answer the question she asked him to ponder while she was getting his drink

In a strong confident matter of fact tone Andrew said “Thank you so much for the tea Natalie. While I went for the overall girl my age look for that is what you asked for. I thought about it and with it being a meeting between two people at a coffee shop, I went for the casual look. I got the black Nike’s with the purple swoop for I liked it the best with the outfit. I felt it show the personality I want of being cute and it fits me being athletic. Also the purple matches my top.

The ankle socks are just the right height for the shoes. You said a woman my age so I wanted to show that they are for a young woman so got the pom pom on the back of the sock. I am only 22 so I can pull of pom pom socks.

The shorts I went with for it is summer and hot. Jeans would be too hot and I am not confident enough yet to go with anything more feminine if I am out on my own. Tell the truth this is the first time I dressed in women's clothes in public.

The reasoning for the top again for it is summer. I looked at many tops and this one caught my eye. I love the color, eggplant purple, and lace trimming on spaghetti straps, waist and cleavage hem. This is the anchor of the outfit and I made the rest of my decisions based on it.

Natalie held back on making any remark on what she just heard. She also did not show the grin she had inside. While having a poker face In an inquisitive manner she said “Undergarments.”

Andy tensed up and looked around for he wanted to make sure no one was listening. When her date tensed back up Natalie knew she did not follow her own advice and quickly changed her stoneface to a big open smile. Seeing his date becoming more open again quickly relaxed the nervous man and he went back to being confident about who he was and went on to describe his choice of undergarments . “I went with pink lace panties for I like how they feel. I always imagine that they would give me confidence and they did. I was able to leave the house dressed like this without having a panic attack.

I went with no bra for multiple reasons. One, I hear women complain all the time about wearing them and if they could away without one they would. I do not need the support and the shirt material is heavy enough to cover my nipples. Plus. with most of my back exposed with the spaghetti straps criss crossing of the shirt, I would feel trashy with a bra on. I am not trashy. I certainly do not want to present myself as trashy to you”

Her grin inside and on her face got bigger; each one of Andrew’s responses was showing he had even more potential than the smitten lady thought he had. The happy lady said “personal grooming.”

Andy knew he was doing great so his confidence grew and he was not concerned if anyone heard his response of “While I did a quick shaving of my legs this morning. It did not take long for it has only been three days since I last shaved them. I put some lotion on them to help them be as smooth as possible. I also shaved my chest and armpits. I would had felt funny if I had hair there in this top. I used a little perfume, I did not want it to be overpowering. This is an afternoon meeting so I just want a light scent.

The makeup I went with was just a natural look. Foundation to hide flaws in my skin, neutral color lipstick to bring them out yet not draw too much attention. I used a little blush to add color. I was going to do eye shadow but was not confident in my ability to apply it and thought it would clash with the look I am going for.

I feel like I cheated with putting my hair in a ponytail. I just do not have it layered right to do anything really feminine with it. I hope that it being a high ponytail is feminine enough.”

Natalie was impressed with the response again. He was just naturally in tune with being feminine, had modesty and best of all an innate understanding of what sort of female he should be. That cannot be taught, it can be nuture to help grow and she wants to see him bloom into being a her.

Natalie finally directly responded to his answers. “Dear those have been excellent responses, I am pleased with what I heard. I see that with a lot of work by both of us you have potential to be my girlfriend. That is of course, if you still want to be. Saying you want something which one believes is unattainable is different than actually wanting it when you can have it.

So if you want to be my girlfriend, you will follow the instructions Iwill be sending you tonight. Do not worry you will have time to think about it before you say yes or no.

If you have any questions you can ask them now before I leave.”

Andrew was happy that she was pleased with his responses. He knew he did well for she is allowing him questions right away. When they are directly talking about forming a relationship Natalie usually want to talk about his answers in more details.

Andy had one question on his mind which is more of a request. He wanted to be called something more than the terms of endearment Natalie had been using. He thought to word it right. When he was finally ready he asked. “Natalie, I would like to go out on a date with you. It is too soon for me to say I want to be your girlfriend. Can you please call me by my name once in awhile instead of just pet names?”

Natalie was so happy with Andy’s statement about needing to see if he wanted to be her girlfriend and him finally asking her to call him by a name. Andy was learning that she will lead the relationship if they got into one, but his say is vital. She did not want a yes girl at her side.

The lady sitting across from the the boy who should had born a lady said “I would. if you gave me a name which fits a girl. Please do not point out Andie from Pretty in Pink again. I understand your point, but you get to pick your name so embrace one which is feminine and does not have a tie to your male past. You asked me to call you by a name so tell me one which is fitting to what you want to be to me.”

Andy did not want to pick a name. Not for it would make him less of a man to do so. He just thinks that it is not fair for him to be able to pick a name while real women did not have the same opportunity. Andy also knew that she is right in telling him to pick one. He needed to break all ties to who people saw him as and make a strong connection to who he really was, a wonderful strong female.

He looks at her and said “Please call me Chloe.”

Natalie smiled at hearing that and wanted to with light pressure to press him into saying that is his name. This will be a big breakthrough. Andy is accepting who he is, but needs this to be done on his own. He needs to take on all the feminine qualities on his own, not have another force it on him. She just said why.

Andy looked at her and said “For my name is Chloe.”

Natalie commended him by saying “Chloe is such a pretty name. I am going to love using it when we are together. I will start pepper in pet names if and when the time is right, but from now you will be Chloe to me.

Chloe, you will need to use that name with me from now on also. I will understand if you slip up and refer to yourself as Andrew, but you need to start to see yourself as the wonderful young female who Chloe is.”

Andy told her he understood while Natalie got ready to leave. She would like to stay longer but wanted to make sure that this meeting was all about Chloe understanding being a woman. Natalie did not want him to think about more than that.

She got up and while giving Chloe a hug said “I am looking forward to seeing you again soon.”

Chloe watch Natalie leave, not caring about how he was dressed. The stares people were giving him did not bother him; The man who was being who he should had always been j felt right at that moment. This is who he is he thought , or is it this is who she is. It was she, yes from now on I will see myself as a female. She finished her drink and left more confident in who she was.

Chapter 2

Chloe got home from meeting Natalie and went straight to the computer. She knew it would be awhile before she got the instruction from Natalies. Chloe did not know what to call Natalie, she is not a friend, not a lover, not a mistress, nor a mentor. The lady who he share a little bit of time with today had potential to be a great friend, great lover, and great companion. He knew that if they both work hard at making this work they both could be the one for the other.

Chloe went on to create a new Y-mail email account. If she is now Chloe, then her e-mail to and from Natalie should have a name which reflect it. After opening the account she went into Andy’s old account to write Natalie a quick e-mail. It thanked Natalie for the wonderful experience of today. Then explain that having her pick out her own outfit, be out in public, and then naming herself Chloe made her grow as a person. She also informed Natalie that she has a new email address [email protected] and asked her to send any mail there from now on. Then she went to her favorite chat room and actually was more assertive in it.

Natalie was doing some shopping for her next encounter with Andy, she meant Chloe when she gets notified she got an email. She checked it and saw Chloe sent her an email The content of the letter made her bright sunny day a little more brighter. It made her think that she needed to make sure she is able to naturally call Chloe by her name casually by their next encounter.

Bringing out Chloe’s feminine side was hard work for Natalie also. She wanted to do positive reinforcement on Chloe. Make him accept the female he was with pride and freely.

After shopping she went right to her computer to write a reply to Chloe’s letter. She was so happy that Chloe also referred to herself as a woman in it. She liked when Chloe made a breakthrough for then they can blend more of the transformation into normal everyday things.

Natalie wrote

My dearest Chloe,

I am so happy that we have finally meet, I can tell by your letter and your reaction you understand why it took so long to finally see each other face to face and it was a quick meeting. You are coming along so great and this needs to be taken in little steps.

I would love to take you out on a date. It will be this upcoming Saturday, a week from today .It will be at my place if you want, if you are not ready to dress even more feminine in public. If not you pick the restaurant we eat at. I want to make sure you are comfortable being Chloe.

I just got done picking out some gifts for you. They are for our date. Please do not say I do not have to get you anything. I know that. It is just I know how much money these things I want you to wear are; they are a little expensive and you do not make as much as me. It will also please me seeing you in them.

I will write you when the items come in and set up a time for me to come over. Remember you want me to call you Chloe so please look like a Chloe when I come over. Looking like an Andy does not fit you dear.


The newly christen Chloe was really enjoy being more vocal in the chatroom when her phone rang. Without looking to see who it was she answered it in Andrew mode “Hello Andrew speaking.”

Hearing Chole use her old name did not phase Natalie. She knew that the object of her affection was not expecting her to call. The woman with the plan to win the heart of Chloe was going to not let her bad experiences from the past hamper her plan to be more open, starting now. Natalie said “Dear to me you will always be Chloe and do not worry about using Andrew. I know you were not expecting me to call so soon.

I got your email and it was lovely. I was wondering I know our date is not until a week from today, but I would love to spend some time with you tonight. I can pick up a pizza on the way over and we can do whatever you want. I just want to spend some time with you and be more open with you starting right now.”

Hearing Natalie’s voice made Chloe's heart skip a beat. She was so happy hearing it that she forgot about using Andrew until Natalie brought it up. Then when Natalie said it was fine it made her at ease about not using her new real name.

Chloe enthusiastically said “I would love it if you came over, Natalie. What do you want me to wear.”

Natalie liked that Chloe wanted to please her, but knew that she has been wrong at keeping the girl she wanted at bay by giving instructions. “First please call me Talie or Nat, that is what all my friends call me. Also wear whatever you want. I would like it to be something feminine, but you still need to ease into it and this is not our first date, I want that to be special. Like I said before I will always see you as Chloe so just hanging out for now the clothes should not matter.”

Hearing Talie’s response made Chloe feel like she was floating. Chloe finally broke down some of the defenses which Talie had up. Chloe knew all the issues and bad luck that she had and understood why her potential girlfriend was cautious. She would had been the same way if her past attempts at relationship also worked out as horrible as her friend’s attempts did. Chloe wanted to make certain to the great lady on the line that she was the real deal. “Talie, just dress casual for I have a nice cute outfit I want you to see. I know I do not have to wear it, but I want to impress you and more importantly I love it. Come over at 7:00, I am so looking forward to see you.”

The lady caller like the sound of Talie coming from Chloe’s voice. She also was pleased with how confident Chloe was when she was open with Chloe. Talie wanted to make that lady she was going to see latter tonight a better person just by being in her life. Her response was ”I am looking forward to 7:00, see you then dear.”

They got off the phone and Chloe left the chatroom to start to get ready to spend some time with someone who she found special and hoped became her special someone.

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