Becoming Sarah Part 1

Author's Notes: This is the first story which I ever try to write when I picked up this as a hobby. I finally went back and started to edit it. I know it is still a little clunky but like the story too much to try to major changes. I want to keep the same tone that I had while writing it.Changing too much would get rid of my mindset I had while I was writing this story.

James Young was walking into his last class of the day, Women Studies. He needed to take a culturally diverse class to meet the criteria to graduate from his university, so he signed up for this one. He figured that he would like the male to female ratio in the class. That is true and what he will tell his friends. The main reason he also did so for he always felt in touch with his feminine side and thought that will help make the class an easy A. If he could relate to how women feel and think then the concepts and ideology in the class should be easy for him to understand and articulate in papers and on tests. He did not share his feelings of empathy with women’s point of view with his friends for he did not care to explain to them those qualities are what made him who he was and made them befriend him.

James was gentle and caring, when growing up he would always be bringing home a stray dog, a wounded bird and and even once an orphaned raccoon. He was also kind, he volunteer and collect for charity, help people when he saw a chance and was always there for his friends. He was late for his first day at his first job for on his way there he changed a flat tire for a lady stranded on the side of the road. He was a great listener. He found that trait helpful when he was captain of his high school debate team, he easily dissected the opposing team’s stance by finding the inconsistency in what they said.

There was also more to James’ empathy to women,he loved their style. He thought nothing of it or he thought all men did also. In a manner he was right, most men love how women dress. It is just the reasoning behind the love was different. James knew that women clothing was not just functional.

James loved how women would use their clothes to express how they feel, how they wanted to be seen and show who they are. He loved how soft women garments are, how careful a women would be in putting together an outfit so matched and had the right accessories. While most other men love women style for how they make the women look. His deep understanding of why women dress the way they do was a part of his empathy he did not know he had.

As usual he was early for class, James always gave himself plenty of time to be where he needed to be just in case he got sidetracked by helping someone, and he sat in the back. He always picked a seat in the back so he could observe his fellow students. As the rest of his classmates wondered in, he smiled to himself thinking he was right about enjoying the female to male ratio. Finally the professor came in.

Once the professor got organized and went up to the podium the clatter in the class started to die down until it went silent once he introduced himself as Dr Allagi. He gave the syllabus to a couple of the students in the front and asked them to pass them back. While they were being pass out Dr Allagi started to go over the material inside the syllabus

It was a standard syllabus, stating time and place of the class, the objective of the class, the university code of conduct, topic cover for each class session and grading. The grading made James smile to himself again; he was right about it being an easy A. No test, class participate, 5 papers and a project. The project was to do something to help you better understand how women are perceived, seen and their place in society today then write a report on it. The teacher explain it can be anything to helping out at a women’s shelter to getting your grandmother to tell you her life story.

The rest of the class was smoothly for James, it was just a huge discussion. He loved discussions for they open up his mind and helped him better understand who he was talking to and also the world in general. The more James understood about the human condition, the closer he felt he was to seeing the world from also other people’s point of view.

James found it funny, not in the ha ha way, that he was the only man who enter into the discussion. To him if he did not know better, it was like they never even try to see the world from the point of view of the fairer sex. James did find how self conscious the other men were, at least they finding out what it is like to not be the dominant gender in a social situation.

James left the class wondering what he was going to do for his project. It did not help him that he heard his colleagues coming up with great ideas as they walked out of the building with him. He did not want to do the same project as someone else. He walked back to his dorm thinking about what his project should be..

James walked into his room and greeted his dormmate, Dillon and got a greeting back. They have been living in the same room together for the last two years. Those two got along well , their personality complemented each other’s and are good friends; both of their social circle do a huge overlap. Them being good friends, not best friends was what made them perfect roommates for each other. They get enough time away from each other so they do not get on each other’s nerves.

Dillon Roberts was an all around good guy. He is the type of person who would give you the shirt off of his back. In fact, James saw him do so. When one of James’ friends came to visit, Dillon had the Star Wars shirt which said who’s your daddy withe Darth Vader on it. .His friend made such a big deal about how awesome the shirt was, so Dillon took it off gave it to him and just went to his drawer to put on another shirt.

James sat down and they both started talking about their day. James enjoyed this part of the day for he would get into a good conversation with Dilon. The question they posed to each other was not just a pleasantry, they both wanted to know how each other’s day went. They both wanted to tell each other for if they have a issue they know they would get the perspective of someone else. It helped them in their personal and academic lives.

So James got to his little dilemma. It is little for it is not important, but James wanted to have the planning down for this class. He knows when he will work on the papers and just want to put in his schedule when he will do this project.

Dillon smiled and said. “ It is simple dress as a woman. I can escort you to a dance the LGBT Student Society. You will also get to know somewhat how it is to be treated like a woman”

If it was any other of his friends, James would think it was a bad joke, but not with Dillon. Dillon was gay. James actually enjoyed having a gay roommate, not so he could show that he was a good liberal with a wide variety of friends. It was for James got a better understanding of gay people, and people in general. He started to see that people are just people, the boxes we put them in should not define them. In fact all it does was limit who the other person could be in your eyes. Also, It was for when they do go out socializing together. Dillon was a great wingman. Girls were more open around a gay man, and James never had to worry about Dillon wanting the same girl as he did.

James thought, hey all guys wonder what it would be like to wear those soft pretty clothes. He also knew exactly how he would dress if he wore women clothing. James really believed all men wonder that question and knew there feminine wardrobe for he was in somewhat of denial of how intune he was to his feminine side.

James responded “Go on about the somewhat how it is to be treated like a women part, I am intrigued.”

Dillon with a shocked look on his face, said “Really, I was just joking, but if you are intrigued here it goes.” He paused for he had to think it through for it was a joke. “You know how once a month the LGBT Student Society has a dance in the ballroom of the student union. While some of the guys dress up as women. The other guys and girls there treat them as women. If you really want to do this then I will be more than happy to take you. I will make sure that no guy tries to treat you too much like a women. I say treat you too much like a women, for you will have to put up with guys hitting on you, and ogling you. I just want to stress you will be hit on, but want you to know If it gets too much for you to handle or they are getting too fresh then I will come to save you.”

That ogling and hitting on comment made James rethink it for a second. Could he take being pursued by a man? He then thought he will not have to worry about it for he will not be good looking as a woman and two if a man was drunk enough or had bad taste to hit on him, he knows that Dillon would be there for the save. That is what wingmen do also,get each other out of trouble.

Dillon went on and mention the he thought that the girls would love to help James with this project. The girls are four of their friends who rent a two bedroom apartment off campus. There was Audrey Salk, the de facto leader. She was a pre-med major. Her roommate, Lilith Rose, who was a sociology major. She was vocal and after graduation was going to be a great women’s right activist.

The two girls in the other room there was supportive Cara Ham and Lexie Lucas, Cara was an education major. She has a way to bring out the best in others. And lastly Lexie, a double major, theater and marketing. She wanted to work in show business to express herself so if she can’t make it as an actress she has a fall back plan of being in promotion.

James called the girls and Audrey answered the phone. He told her that he had a huge favor to asked from all of them. Audrey told her friend, he knew they would do anything for him and wanted to know what it was. James got a little embarrassed when he thought of the project and said it was better to tell them in person. Audrey invited him over for supper that night.

James got a nice chocolate cake on his way over to spend time with his friends. They had roasted chicken with carrots, potatoes and parsnips for dinner and caught up during supper. James offer to serve dessert , Lexie told him not to be silly, he was a guest so she will do it.

They were eating dessert and Audrey brought up James’ favor. James was a little surprise that he got nervous when she brought it up. Cara noticed it and told James not to be that they will love to help him. James said that he needed help with his Women Studies, project.

Lilith was ecstatic when she she found out James was taking that course. She thought that all men should have to take Women’s Studies so they better understand the plight of women in today’s society. She happily made the decision for all the girls “Of course we will help with this project. Oh I can tell you some great books to read so you can research what feminism really is before you pick your project. Start with:The Feminine Mystique, The Bell Jar.”

Audrey interrupted her and told James to continue.

James said “ I have to write a paper on a project which I do which will help me better understand how women are perceived, seen, their place, and role in society today.”

Lilith interjected again “I have some great charities you can volunteer at.”

Audrey was stern when she stop her friend from trying take over the project “Lilith, let James finish what he has to ask. It is his project and not yours.”

James took a second to continue. He wanted to gather his words and picked them carefully., James wanted to make sure that the girls know that he is not doing this as a lark. He knew that how hard it was to be a women in society and him dressing and being treated like one by a few people did paled in comparison to what a woman really has to deal with.. He knew it will only be really for that dance and a weekend in his dorm room. He wanted his friends to know he will take this serious.

He said “ I will talk to my professor about this and if he likes my idea then we will do it. I do not see why not so I wanted to know that I had your help and support before I got the clearance from him. My project is that for a weekend I will live as a woman.

I need your help with getting the right clothes, accessories, makeup and hair. I want to do this right and make sure it is not disrespectful to women. I am asking you girls for I know I can trust you to not tell everyone about it. You know most guys will not understand this project, hell I get grief from them for just taking the Women Studies class. So will you please help me. I know, I will owe all of you a huge favor.”

They all said yes for different reasons. Audrey figured that James is a crossdresser and found an excuse to do so, good for him. Lilith wanted James to see how hard it was to be a woman, oh he was going to wish he never thought of this idea. Cara wants to be supportive to her friend, he should not have been nervous asking. Lexie thinks it is a great idea to help James get in touch with his feminine side, it was going to help him grow into a more well rounded person..

The girls started to talk about how they can better help James. Cara said if the others girls don’t mind he could stay there for the weekend. Lexie always spent the weekend at her boyfriends so those two could be, in her words, “roomies”. Plus he would not be stuck in your dorm room and not wait until halloween. Cara, was in the moment and wanted to use this project to become closer to her friend, and pleaded with Cara for James to be able to use her bed..

Lexie said “Of course he can use my bed that weekend. But I am not going to miss this. I want to be there for my friend. I will hang out with you girls on the Friday night and meet up with my boyfriend later.

I can get the hair extensions, breast forms, and silicone hip enhancers from the drama department.

Lilith had a plan brewing already in her head, how to make the weekend the worse one ever for her friend and was not going to let Lexie ruin it. “let me help also, I can borrow breast forms from the breast cancer survivor charity I volunteer at.”

Lilith thought that was the first way I am going to make James see how hard it was to be a woman. She was going to get him a nice big pair of breasts so men will stare at them. Plus those men would see he was just a man in drag, so they would just mock him. He was going to know how shallow men were and feel how much that hurts when dealing with them.

Audrey said “I can help you with the makeup and grooming. If we are going to do this, we are going to do this right. You will wear casual makeup around the apartment, do it up more for when we go out and then go the whole nine yards for when you are at the dance.”

James felt so relieved that the girls were happy to help. He was also happy that Cara thought about where he would stay when he was dressed. He was shocked that they are all taking ownership of the project. He did notice that it was communal with how they were helping, they volunteered to do what they would be the best at. They were working as a team and adding to each other ideas.

Audrey asked James where he was going to get the clothes and his answer was at thrift stores to save money. Audrey did not like that answer and knew it was only so he could afford doing this project. “If we are going to do this then we are doing this right. I know you want to do this right. I will buy one of your outfits to help you with the costs.

I know you want to look nice in public and also you need to experience shopping for clothing from a woman’s point of view. There is no way my friend is going to a dance to impress people in clothes from a second hand store. I want you to feel and look as fabulous as you can.”

James was touched by what Audrey said. “You are right. Thank you so much for the offer. I will just make sure that I budget my money better this semester so I can do the weekend right right.”

Lilith smiled for she thinks that Audrey is on her side to make James dread what he just signed up for.Lilith said she will pitch in to help with the shopping. Cara said she loved buying cute gifts for her girlfriends so she will help also. Lexie agreed with Cara and put a little emphasis on the word girlfriend in her reply. Lilith made eye contact with James and grinned. Those two were going to help also, this is going to be so great making him suffer.

James got a little unsettled how Cara and Lexie said girlfriend . He showed it by tilting his head down and frowning a little. Lilith said “Don’t get upset honey, put on your big girl panties.”

Cara said “That is not nice Lilith.” Then she looked at James “I am sorry, I was just ribbing you. I see how you took why you took it wrong and I did not mean it that way. That does not change the fact you took it that way. You know Lexi and I did not mean anything negative about that and would never question your manhood.”

Lexie quickly apologize also. She knew how inconsiderate she was in making that joke. She wanted to be supportive of her friend and instead put him down. She went for a laugh at his expense.

Lilith did not want to make James too uncomfortable about the weekend for then he would back out. She was not going to waste this chance of making a man feel how men made her feel. Sounding sincere she said “Sorry I just got a little carried away.”

James turned red from being embarrassed from his over reaction. “I understand and I took it wrong. I am now figuring out I am signing up for more that I thought I would be.”

With it sounding like James was rethinking this project, Lilith could not resist to get at least one last taunt in on him. Lilith, with a little condescending tone in her voice, said “ If you are not woman enough to do this we will understand.”

Audrey said “Enough joking around. Lilith sometimes you just do not know when to stop.”

Lilith was happy that Audrey was so logical, she jumped in to do damage control to make sure that James will go through with this.. In a sweet voice Lilith said “I am sorry James. Do not let our jokes at your expense make you back out of this weekend.”

James wanted to play back to show his was fine. He looked at Lilith with a smirk on his face and said. “Audrey it is fine. I might not be woman enough to do this project, but I am man enough to try and do my best.”

How James reacted made Audrey decide that she was going to start viewing James as a woman and treating him like one. It will help him transition for the weekend. He would feel more natural being seen as one of the girls when the time came

Audrey would not straight out say it to him, but she would always think of him as a her.while interacting with him. She thought it would be for the best if they all did the same, so she was going to tell the girls her plans after she left. It was not that she was trying to be mean, far from it. It is so he can feel more comfortable when other people are doing so. The girls would be more natural around him on that weekend also.

Audrey “What are your plans for that weekend dear?”

Lexie “Yeah I want to hear them.”

Cara with glee in her voice “We can have a slumber party!”

Lilith hated that it looked like her friends were actually trying to be supportive of James. She wanted to talk to them about how it was their chance to have a man be treated how they were and was planning to when she came back. She abruptly got up and said “Oh sorry I am out of here. I totally forgot, there are some things I need to do at Women’s Student Association.”

Lilith stormed out and slammed the door behind her. They all knew what she said was a lame excuse to leave. Audrey said “do not mind her, James dear. She is just mad you got the last word.”

James said “How about this for my plans. On Friday after I get ready we all can go out for a nice meal and see a movie. I know all four of you have a monthly girl’s night when you do that. Tell the truth it will also be nice to be around you for then not as many people would look at me. Then we could spend the night afterwards just chatting about the experience. I so want your input about how I acted. It will help me be able to better express how I felt about the weekend if I talk about it to close friends like you.”.

He paused after that to get the feel of how the girls felt about his plans so far. Cara said “I love it and I want to know how you feel about it. It will make us closer as friends.”

“Good thank you Cara, then I will do my normal Saturday morning routine of going for a jog. I would love it if you came with me Cara for support.”

“James, I would love that. Plus I can buy you a nice cute workout outfit,

James shaked his head and laughed again. He was happy that Cara was not beating herself up about that joke. Cara was so empathetic and hated when other people were hurt. James knew his friends were not being mean about and saw why James could had taken it the wrong way.

“Then after the jog just stay at home until I had to get ready for the dance. Nothing major just hang out. I would love to do some general girl talk, you know things women talk about without men around. I need to be part of that to better understand women.

Plus I just want some time to relax and be cozy. I like how women can be cozy.”

Lexie jumped in “I will buy you a nice cozy outfit. It will be comfy.”

“Thank you so much Lexie. Then Dillon will pick me up for the dance. Then if I do not get home too late and any of you girls are up talk again about my experience.

Then we can have a nice brunch on Sunday and then unwind and return to being the unfabulous James.”

Then Audrey said. “With it being a good groundwork You do need to work on it some other issues. First what will be your name”

James did not give that much consideration ablurtted out “Jamie Lee.”

Audrey with a little disappointment in her voice said. “Dear, it cannot be Jamie Lee. Think of it your name is James and Jamie is a nickname for it. It might work for people who do not know you, but we will still see you as James if you go by Jamie Lee. You will also just see yourself as James.”

James felt bad for she was right. He also did not notice she called him dear, Audrey only called girls dear. James replied “Sorry Audrey, I am taking it serious. I really did not give much thought to a name for people are given names.I do know that if I was born a girl my mom would have named me Sarah Marie. So I am going to go with Sarah.I will be Sarah Marie Young”

Audrey smiled. “It is fine James, I know you are being respectful, dear. It is just I wanted to let you know why I had an objection to that name. You do have the final say in this for you are doing this. We are just going to support and guide you dear. You will be a great Sarah.

Next question, what breast size will you want? Now, I know you might not have thought about this, but we will need to know for the outfits and also so Lilith will get the right size.”
James thought about it. He felt like Goldilocks for did he not want to go too big or too small, he wanted them to be just right.

Thinking back to his last girlfriend who was a little thick for a girl, he should go with her size. She was a B cup and looked natural on her body. James had the answer to Audrey’s question and gave it. “I think that B cups would be the right size for my body. So unless I am going too small I say B cups.”

Audrey smile hearing his answer. It is nice that he wants their input also “You are right about the size being right for your body. Now bra, panties and sleepwear I suggest just getting a pack of cotton panties, a bra and use those for everything other than the dance. The dance I suggest to get a matching set of bra and panties. Trust me you will just feel better about yourself at the dance in matching bra and panties. It gives a woman confidence.

Sleepwear you will just have to look up and see what you think is best, I would suggest something more feminine than female pajamas, they will feel like soft men pajamas on you. You will want something without pants legs. Remember the less you wear of something a man can the more you will feel like a woman”

James agreed again. He is a little taken back at how serious Audrey is taking this. He was appreciate it. She was really thinking about it and being so supportive. That was why she was such a dear friend.

“Now onto the makeup and perfumes. One reason I said that I will help you in this area is that we have the same skin complexion. Other than the eyeliner, mascara and eye shadow, I will share mine with you. In fact, we will go to the drugstore when the time is right and we will get those. My treat. I will just use it after that weekend.

You will have free range on my perfumes, deodorants, and bath gels, dear.”

James eyes became a little glazed from the overload of information.He never realized how much work was involved with being a woman. Audrey knew James needed to catch up with her so she took a little break.

After James soaked it all in Audrey started back up. “ Now the next area the accessories and shoes. You will need the right shoes for what you are doing. I already know the outfit I think you would like for Friday so we will need a pair of Mary Jane pumps for them. So if you like the outfit we will go with them. I also think that you will be able to use them for brunch on Sunday”

James looked a little confused so Audrey went on to explain them. “A Mary Jane shoe is low cut with a strap across the instep. A pump is a heel in the back which is an inch or two. The heels are also chunky, so they will be easier to walk in for you. You will need a pair of flats for around the house. The flats you will pick out after you decide on the outfit for lounging I think you can wear your normal running shoes for the jog, and after you pick your dresses for the dance we will pick the high heels.

We will supply you with purses, unless we do not have one which goes with the outfit.

Now Earings, You have both ears pierced. You can go to chain boutique, Claire’s and buy some costume earrings and maybe even a necklace if any of the outfits need one. You can also get some hairbands and clips for even without the extension you do have long hair.”

Cara jumped at the chance to go to Claire’s. Lexie suggest that they all go to the mall this weekend to start the shopping. Audrey said she thinks everything is covered. James agreed, in a little bit of a daze. He felt a little overwhelmed from everything which needed to be done. He never realized how much work it takes to just have the right outfits. Everything has to not only match but be right for the occasion, even if it is just lounging around.

The subject went back to catching up one what is new in everyone’s life, and it is mostly their new course work. Audrey talked about she is enjoying her new classes. Cara brought up about how great it feels auditing a real classroom twice a week. Lexie was excited about winning the role of Sandy in the musical Greece. She sang a little of Summer Loving. James never heard her sing and was amazed at how great her pitch is, she must be close to pitch perfect for how she just started to sing so well without warming up.

After talking for a while longer James got up to leave. They all said goodbye and Audrey walked him to the door. She kissed him and the cheek and hugged him well saying “ Now when you know which weekend it will be call us or if you think of anything else. Don’t worry about anything, we are going to have a fun weekend and you will learn so much about yourself and the fairer sex. Have a good night dear. ”

James did not notice that she treated him more like a girl leaving than a boy. As he left he thought Audrey’s farewell was a little strange. A hug, kiss on the cheek and calling me dear. James also notice that she used dear when referring to him. He swore she never did so before. It must be her way of showing her support or he was reading too much into nothing he thought so he just shrugged it off.

After he left Audrey told the other two how we were all going to be very supportive of Sarah. She said “For this to be a good experience for Sarah we need to see James as her until after that weekend. So from now until the end of that weekend I think it is best if all of us see her as Sarah. We also need to be extra nice well doing so to build up her confidence. Agreed girls?”

They agreed and was going to tell Lilith about their great plan when she came back.

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