Part 3---In order to get into a top college program, Taylor will climb over a series of unusual hurdles. With the help of his mother he goes all in to get a scholarship. In this section the new Taylor becomes more social. His journey leads him down a road of self-discovery.
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Transitioning To College 3---

Chapter 7:

I had some nasty daydreams during the evening and I couldn’t completely shake my anxiety. Every time the phone rang I was scared that it was one of my friends calling to say they heard about my cross-dressing and wanted to tease me. I was grateful that none of those calls ever materialized.

I still couldn’t shake my anxiety and I was still petrified as I entered school on Monday morning. The day was going fine until right after third period when I once again ran into Julia.

“Hey Taylor, How you swinging today? I see you are dressing down today.”

“You promised to keep it between us.”

“You can trust me. I will keep my word. I promised that I will not tell anyone that I saw you at the Doctor’s office and I won’t.”

“Thank you. Please don’t tease me here. Someone might over hear you.”

“I’ll keep it between us girls.”

I walked down the hall feeling like all of my blood had just drained out. I was going to be her personal torture doll. There wasn’t much I could do, but at least she said she would still keep the secret. No one had said anything to me besides her, so maybe she was going to be reasonable.

Reality struck just before my last class. I was standing in front of my locker when a senior girl that I barely knew leaned up next to me. She was very attractive but part of a snotty click that I usually avoided.

“Hey Taylor. I understand that we have a lot in common. If you ever want to go shopping together I would love to hit all the trendy spots with you.”

"What? I'm not sure what you want, but I think you are mixed up."

Thankfully, I was saved by the bell. Reality was setting in and I knew that Julia had blabbed. If this girl now knew, the gossip mongers would be quickly spreading the word to many more. I was going to have to except it. So much for my social life....

That was my only confrontation at school Monday, but I knew it would not be the last. As the week moved along my embarrassment spread like a slow moving virus. At first it was obvious comments from a few girls or knowing smiles from some that I had never spoken with. By Wednesday, my male world was caving in on me.

My long hair had gotten me some derogatory comments in the past, but the fact I was a decent athlete and not a social recluse usually was enough to maintain a macho opinion from my casual friends. I was quick to find out which so called friends or classmates were jerks and which others were intolerant or hateful.

In front of other students one asshole in gym suggested that I was in the wrong class. "Girls gym is in the pool today."

There was no way I could defend myself in mass, so I basically kept to myself. I even tried to avoid my two best friends. The whole experience was hard for me to internally reconcile, so how was I going to explain it to my friends.

At home I tried to isolate myself from the outside world. Other than going for a daily run, I would stay at home, mostly in my room. I used to enjoy occasionally studying at the library, but now I would just stay at home. On Thursday, after school my friend Josh stopped by unannounced.

I really didn't want to see anyone, but my mother called to me and sent him up to my room.

"T, what’s going on with you? I'm hearing weird shit and don't know what to believe."

"Believe what ever you want. Everyone else does."

"That's not fair. I'm here. We go way back."

"Yeah, I know. It's not your fault. It still doesn't change things. I'm screwed."

"You can talk to me. I don't care what others say. Actually, after a while no one else does either. There are always some idiots out there, but they were never your friends in the first place."

"Thanks, I appreciate that. It's just kind of complex."

"It probably feels that way. You know you are hardly the only gay kid at school. Half our friends are probably gay."

"Gay?"

"Yeah that's what I heard."

"That bitch. I'm not gay. Like I say it's not that simple."

"It's no big deal. Gay, Bi, whatever it's cool."

"I'm not sure how to explain it, but she saw me acting like a broad and is spreading this gay bullshit."

"Why were you acting like a broad?"

"It was part of an attempt to get into a program at Northwestern. I'd rather not go into all the details."

"Kind of a hazing thing?"

"I wouldn't call it that, but I had to prove something to get consideration. So it was my choice."

"We will have to get back at her then. Lets start a rumor about her."

"That might be fun for a laugh, but that would bring us down to her level."

"What should we do then?"

"Nothing. I can live with this. I have friends like you and I don't care what morons think.

"You are going to let her get away with this?"

"I don't want to draw any more attention to myself. I will probably confront her directly or figure out some subtle way to turn the table. She has some issues of her own that she has to live with. I am not going to have a public battle. If people want to call me gay...fine. I am still the same person I was yesterday."

"Wow. I don't think I could be so calm."

"If we are cool, that's all I care about."

"Sure Taylor."

"Let's work on math and honors bio together after dinner."

"Great, why don't you come by my place at 7:30."

"See you then."

The school thing was a bit of a drag. It was not relentless, but every so often somebody would say something hurtful or treat me like an oddball. A couple of male classmates that I didn’t previously hang out with started to become more friendly with me. Their motives made me speculate about their orientation.

I finally confronted Julia on Friday morning and she was hardly apologetic. I called her a liar and lowlife for spreading the gossip.

"I didn't lie... I said I would not say I saw you at the psychologist office and I didn't. I never said I would not say I saw you."

"You are pathetic! I can see why you need help. You don't give a shit about others."

"At least I'm straight."

"With your attitude, you may be straight but I bet you are lonelier than me."

I could see that last comment hit home. As soon as I said it, I wished I could take it back. I was angry, but I knew she had personal issues and I felt I had stepped over the line. Before I could say another word, she just walked away from me.

I was happy that my real close friends didn’t seem to care that much. It wasn’t like any of us were in the popular social set to begin with. It probably ruined my opportunities with some of the cuter girls in school, but I tended to be kind of shy anyway. By the end of the week I had pretty much adjusted to being treated strangely. I was glad all of the abuse had been verbal and no one had taken it to a higher level.

I certainly had a lot I could discuss with Dr. Gordon on Saturday. So much had happen since the last moment I had last emerged from the Doctor's private lair. I had survived a traumatic encounter and had grown stronger as a result.
 
 
Chapter 8:

For the last few days I had not been daydreaming as much about woman’s fashion. The distractions had been great and I was now more focused on the eyes of everyone around me. I was torn about what I should wear. After having run into a classmate in the Doctor's waiting room, I felt like low-keying my androgynous style statement for my appointment. I settled on yellow slacks and a maroon V-neck sweater. The slacks had a boot cut so I wore the MaryJane shoes under them. I wore my hair in a ponytail, much like I always had. I did wear it a little higher on my head and instead of a rubber-band style tie, I used a thick scruntchie.

I could easily see the disappointment in my mom's eyes when she saw my appearance. Before she could say anything, I cut her off.

"After last week, I am taking a step back this week. I am not in the mood to go through that waiting room experience again today. Maybe another time, but not today."

"How about I just touch up your face with some light makeup?"

"Absolutely not. This is as far as I am going today. I probably shouldn't even wear these clothes today. I just need to be more perceptive to my environment. If I run into Julia or anyone else at the office today, I may be able to get away without any more damage to my reputation."

"Fine, but I know you enjoy your dressing opportunities."

"Maybe a little, but that doesn't change anything. Let's go."

The Doctor was slightly behind schedule and I hated the 10 minute wait in the lobby. Fortunately, the patient that left her office was a complete stranger and never even looked over at us.

I gave Dr. Gordon a watered down version of my stressful week. Dr. Gordon was surprised that my gender ambiguity had never before been an issue at school. At each of the appointments I had chosen to reflect that part of my personality and she had wrongfully assumed that some of that periodically bled over to my school fashion statements. It began a new direction in our discussions. She expressed empathy for how hard it must be for me to repress those feelings in my everyday life.

The result of the discussion led us to talk more about my real desires and where I saw myself down the road. This was a completely new area and a good segue to discussing Northwestern.

"More than anything in the world I want to go into a pre-med program at a good college. As you know, my dad was a Doctor and I really want to be one too. My first choice is to go to Northwestern, but it may not be realistic. I am getting ready to apply there, but even if I was lucky enough to get in, I don't think my family and I can afford it. If it's not Northwestern I have some decent fallback ideas, but cost will definitely come into play."

"You know Taylor, most kids your age are still trying to figure these things out. I think it is great that you have that as your goal."

"It's what I have wanted for a long time."

"Why Northwestern?"

"It has great programs, a phenomenal reputation, and for some reason I have always felt comfortable on their campus. We go down to Evanston frequently with my mom working at the Hospital there. I am sure there are a lot of other great schools, but it's my first choice."

"I think it is a great school too. I received my masters degree in Psychology there."

"I didn't know that you were a Wildcat alum."

"The school is why I opened my practice in this area. I like the way the town blends the big city feel with the community experience of the north suburbs. I am still involved in the psychology department there as an advisor and consultant."

"What do you do?"

"Not that much, but one program that I have some experience with, might be relevant to you."

"How so?"

"I don't know if this is to soon to talk about it, but I am indirectly involved in their Transgender Student Association. It helps students adjust to their gender issues and can even provides some scholarships and special admission consideration."

"I sure wish I could qualify for that kind of help or aid."

"When does your college application need to be submitted?"

"Well, I was planning to have it in for early admission consideration."

"That may not be enough time for my evaluation and recommendation for this program. I have to submit a thorough and very specific recommendation with the students admission application to be considered for TSA treatment and benefits. I am only allowed to support one new student each year. The pre-evaluation process has certain criteria that must be met."

"Have you recommended any one yet?"

"Not this year, but you have not yet met all of the per-qualifications yet. I think you might be a good candidate, but we would have to accelerate some therapy that to finish up some of the per-recommendation evaluations."

"I can come more often to your office if that would help."

"It might, but it is not all about our psychological discussions. Some of it has to do with your life experiences with your gender feelings."

"I've told you about a lot of those feelings."

"Yes, and I think it is wonderful how you are opening up and beginning to live out some of your deep inner personal emotions."

"Well, what more do I need to prove to you or the school?"

"It's mostly about experiencing some of these feelings in more open environments. To be in the program you need to show that you can be open about these personal issues and interact with the public. My evaluation requires me to discuss with you your experiences as a transgendered person in the real world."

"I told you about what happened at school this week... isn't that real world?"

"Yes, and you handled that well. However, that is a small sampling. You need to put yourself out there in a more visible way. At this point you may not be ready to move in that direction and that may be something you never want to do."

"What would I have to do to show my commitment to get considered?"

"As I said, time may be your biggest enemy. It's hard to fit a bunch of experiences in a small window of time."

"I know I am willing, if it can help me get into Northwestern."

"I don't know if you understand what would be necessary. You would have to reflect your alternative gender interests and spend time doing everyday regular activities. It would not require you to do this at school yet, but I would want you to spend a lot of your free time expressing and experiencing your feminine side. I need you to do this so that I can discuss with you how it felt. For you to get into their program, I need to endorsee your ability to handle the situation and contribute to other similar students."

"What do I need to do?"

"I may need to give this some additional thought, but I definitely would want you to dress to reflect your feminine side in a way that leaves no doubt about your feminine feelings. You could go all the way to looking completely like a girl or if you were more comfortable something slightly short of that. It is important that people need to relate to you and see you in this way. You could do this after school on some days, but I recommend you spend your weekends fully dressing to reflect this part of you. I would want you to do this until I have had enough time to thoroughly discuss the experiences with you. If you are all in, we might be able to complete this in time for your application."

"Wow. That is quite a big challenge."

"It would obviously be challenging, but it would also be a big step. You would learn a lot about yourself."

"I wouldn't have to do any of this at school, right?"

"Well not technically, but when you are fully experiencing something like this it tends to show up in little ways in all aspects of your life. Usually, not as planned. I think it would also be healthy if during this period you confided with a friend or friends about what you are going through. I don't specifically require that, but it goes a long way in showing how well you can adapt."

"I so want to get into Northwestern and I am willing to do almost anything to reach my goals. This is not something I had expected, but for a limited period of hardship, it could help me for a lifetime."

"Probably in ways you never thought possible."

"Okay then, I will give it my best."

"Taylor, this is a big commitment that shouldn't be taken lightly. I want you to give this some more thought before partaking in this crash course. I will also need to talk to your mother openly about this discussion and plans. She is still your guardian and I will need her to be on board."

"I am guessing that won't be hard."

"You can tell her about our conversation and I will call her later this afternoon."

"Dr. Gordon, I appreciate everything you are trying to do for me. I am really glad I came here. I will see you next Saturday, maybe by then we will have stepped things up a bit..."

"That is possible, but give this all some thought first. I look forward to seeing you then. Bye."
 
 
Chapter 9:

I had a lot to tell my mother. Even though she was fully on the gas peddle for this un-orthodox college strategy, the current turn of events was probably more involved than she was expecting. I was certain she would be on board, but I imagined she thought the path to Dr. Gordon's recommendation would be simpler.

We slipped out of the Doctor's office undetected and headed home. I began to fill in the details of my session. Despite the fact that she was driving the car, I could see her eyes dilate. While clearly flashing a surprised reaction, she also looked comfortable with the news.

"Dr. Gordon will call you later today to fill you in and get your approval. I already told her I would give it a try."

"Taylor, if you are going to do this, you will have to be all in."

"What do mean?"

"I'm just saying that this is not a half measure. You are not going to just comb your hair now and then to look prettier. You will have to learn all about being a girl. That includes personal hygiene and how to behave. I will be teaching you things your sister learned over many years and mostly out of necessity. I want you to consider this through, before you agree. If you decide to 'give it a try,' it will be without hesitation.

"I already said I was willing."

"Taylor, this will be a giant step up from the dress-up games you may be thinking about. Over the next stretch you will have to basically live and act like a girl whenever you are away from school. I will help you, but only if you do not fight it. You may quickly find this is more than you bargained for or can take. In that case you will have put in a lot of effort with little to show."

"Dr. Gordon did not say I had to live and act like a girl all of the time away from school. She just said to try and act outwardly feminine on the weekends and some days after school. I can live with her request."

"Honey, it will be too difficult to keep going back and forth when you feel like it. When you are not at school, you need to just think differently. It will be an easier adjustment if you always know how to act based upon your environment. With less confusion you will gradually be much more natural and as a result more comfortable. If there are special reasons that on some occasions you need to act more masculine, then we will make exceptions for those times."

"Do you really think that is absolutely necessary? I still want to have a life."

"I do. You still can have a life, it will just be a little different and that's the point."

"What about my friends?"

"That is your call, but based upon how Josh treated you, I am sure you could tell a few selected friends. Maybe the new Taylor will make friends as well."

"I doubt that. Let's talk again after you speak with Dr. Gordon. It will give us both a chance to sort out our thoughts."

"That is a good plan. I will take care of everything."

"I hope I shouldn't be worried about that."

"Just enjoy your time as a boy for now, because we are going to have to get started very soon."

Somewhere around 3:00 I could hear my mother was on the phone for an extended period of time with the doctor. She took quite a few notes and when it was over my mother looked pleasantly satisfied. I was certain she was going to approach me with an update, but she waited until dinner to discuss things with me.

"I had a nice conversation with Dr. Gordon. She was very informative and is hopeful about you being included in the Northwestern program. It's not a certainty, but if the next few weeks go smoothly, she said she would write you a sterling recommendation. She is leaving the spot open for you if she still feels by the deadline that the program and you would both benefit from your inclusion.

"That's great!"

"She also thinks my idea of you spending a majority of your non-school time exploring your feminine side would be effective. She thinks that is best, but did not want to back you into a corner or put too much pressure on you."

"Understood"

"I am going to give you one last time to reconsider. If you move forward, I don't want to hear any complaints. I know a lot of this will be fun for you, but this is a serious commitment and not all of it will be fun and games. It might also indirectly spill over onto school."

"How's that?"

"Nothing specific, but your grooming and behavior are likely to get blurred. It's not so much how you dress as much as the other little things that send out cues."

"Yeah, but I can control things at school."

"We'll see."

"If I get into pre-med at Northwestern, everything will be worth it."

"So your answer is?"

"I'm in!"

"After school Monday we will begin. I will give you a few days of lessons before your next Saturday appointment and that will be your coming out day for the Doctor."

"I hope I am ready."

"It won't happen all at once. You will adjust gradually. Your sister probably won’t recognize you when she comes home for a visit in three weeks.”

“Does she have to know?”

“She already does. I sort of filled her in on out college strategy. She is excited to see how you look.”

“Why did you tell her?"

"We talk all the time and besides she was going to find out eventually, one way or another.”

“You are probably right. On that note, I think I am going to go for a long run.”

"Good idea, that should be helpful to get your figure in better shape."

"MOM, I am in good shape and I run a lot."

“I know honey, and running is definitely good for your figure. You have a healthy lean body, but for a girl you could probably afford to shed another 5-10 pounds. A woman’s weight is spread out in different proportions than a man’s. If you drop a little, everything will look even better when we use foundation garments to build you up where you are lacking.”

“I already workout a lot.”

“We will just watch our diets closer. I will do it with you. I could probably benefit from loosing a couple of pounds too. More salads and clear soups for both of us.”

“If you say so.”
 
 
Chapter 10:

The remaining part of the weekend I intentionally tried to be social with my friends. I made a point of calling my closest buds to see what was up with them. I even invited a couple of them over to watch the Sunday college basketball games. March madness had just begun and we ate some popcorn and bonded for a while. I wasn’t sure when we would be able to do something like that again. My biggest disappointment was that Northwestern had once again failed to make the NCAA tournament.

I knew Monday would begin my motherly guidance. I was not sure what to expect other than a change of clothes. It all began following dinner. I had worked on my homework before dinner and had completed most of it.

I was prompted to change into my panties and a bra. Instead of getting dressed mom gave me a light terry cloth robe to cover up body. She had me follow her to Nina’s bathroom where she had set up a series of makeup articles on Nina’s bedroom vanity.

“You are going to have to learn how to apply makeup by yourself. With your fashion sense this should come natural to you, but it takes a fare amount of skill to do it right. Too much and you look like a clown, too little and you might look butch. You have a lot of choices and it will depend on the look you need to achieve and what you are wearing. For the first few days I think we will focus on the very basics.

“Like lipstick?”

“That’s part of it, but basic foundation, concealers and especially eye makeup will be our focus. I want you to be able to put on mascara, and eyeliner with out making a mess. All of the skills will get better with practice. On the bed over there are two books about nothing but makeup application. Try and flip through them over the next few days. I have also stacked up a bunch of fashion magazines on your desk for you to look at. You can learn a lot from them, and keep up with what is trendy. I signed you up for your own subscription to InStyle Magazine and Teen Vogue.”

Over the next hour and a half I rotated from watching my mother put on makeup and trying to put on the same cosmetics on myself. I had a very rough time with even the simplest skills. That first night I don’t think I got anything completely correct. We repeated the lessons each night for the next three evenings. I never got fully dressed on any of those nights. It was all about cosmetic training. By the end of Thursday evening, I was beginning to get the hang of it. I was no expert, but I could make myself presentable.

On Friday I expected to continue my lesson, but when I got home I was told to get dressed in something casual and comfortable.

“Go put on some makeup, we have a stop to make before dinner.”

I was leaving the safe confines of home and heading somewhere unknown. I knew better than to resist. The stop was at Lulu’s.

“Why are we here?”

“Tomorrow you are getting your hair touched up and your first professional manicure. Today we are going to clean up your peach fuzz so your body will be nice a smooth all over.”

“What is she going to do?”

“It’s called a wax. It’s what girls have to do to look and feel smooth.”

“Why couldn’t she do it tomorrow when she touches up my hair?”

“All these things take time. This way tomorrow will be more of a pampering or spa like experience. The waxing is a lot less fun.”

She was so right. I was in great pain from the full body ripping. I also had red patches in many areas. I was told it gets a little easier the more often it is done. That was a very small consolation. Tomorrow morning after my 9:00 cut, I was scheduled for a mani-pedi.

We picked up salads from the Corner Bakery on the way home. In the car heading home my mother filled me in on some additional Saturday plans.

“After Lulu’s you will have your Doctor’s appointment. I am sure she will be pleased. I think we will also do a little light shopping.”

“More shopping already.”

“You need some of your own cosmetics and a couple of purses. After that I think we will have a little fun by walking around the Northwestern Campus. With all the effort you are putting in to going to school there, I thought it would be a good place for you to spend one of your first afternoons looking like a coed. Besides, it's going to be such a warm day and we can't waste it all indoors.”

“That should be fun and a safe place to go because I am unlikely to see any friends there.”

“Eventually you are probably going to run into some of your friends, but you are probably right about not seeing them on campus. If we have time we can eat dinner at Koi. I know it is one of your favorite Japanese restaurants.”

“That all sounds great. I just hope that this all impresses Dr. Gordon.”

“I am pretty sure you have already impressed her. Just relax, tomorrow should be enjoyable.”
 
 
Chapter 11

Saturday morning began a day that I will never forget. I woke up early with little prompting from my alarm clock. The bed sheets had felt so wonderful caressing my baby smooth skin. My mind was racing in anticipation of going back to Lulu's and seeing Dr. Gordon completely dressed as a girl. I was still scared that I was to extreme a step in the pursuit of my college dream, but another part of me remembered how good I felt after the first time Lulu had transformed me to my alter ego.

The last two days had been freakishly warm for late March in Chicago and today was predicted once again to make it into the low 70s. It was a nice change from the freezing temperatures that we had experienced less than a week ago.

My mother wanted my look to be unequivocally female and she helped me select a short flouncy teal skirt and a multicolored Free People brand baby-doll top. The top had a lace tie in the back, which helped the blouse hug my newly rounded chest. I wore a western styled jean jacket to cut the morning chill. The leather boots only covered part of my hairless legs. On my wrists were matching leather bracelets. My hair was left up in a ponytail, but that would not be for long. A dainty pair of drop earrings were easily visible on my lobes. I was wearing a minimal amount of makeup because Lulu's assistant would be touching that up after my styling.

I was Lulu’s first appointment Saturday morning. I could see her eagerness as our eyes first made contact. It was obvious that she was enjoying helping me create my new image.

“Taylor, I am so happy to see you growing up before my eyes. I can’t believe you are the same boy that I have had in my chair all of these years. You must be so thrilled to finally being you.”

“Lulu, I appreciate your sentiment, but don’t get carried away. I am still that boy and I have to go back to school Monday as that boy.”

“That is truly a shame. I so want to give you a style that would be less gender flexible. You have such great hair and there are some stunning style that would look fabulous on you.”

“Sorry, but no can do.”

“How did you like the curls I gave you last time?”

“Those worked. I was able to go back to my old self when I washed them out. My hair never looked like that after the first day, but for that afternoon it did look pretty special.”

“We could do something similar that would last longer.”

“I have to go back to school.”

“If you pull your hair tightly back and put it in a firm ponytail the curls will hardly be visible. It will give you more flexibility for when you want it to look softer and have more volume. You also won’t have to come in every time to achieve that special look.”

“You really think I can make myself look masculine if I let you give me that style.”

“Well I always thought you were pretty, so masculine is not my first choice of description. I am sure the curls can mostly be hidden.”

“Okay then.”

Lulu cleaned up a few damaged split ends, but basically did not cut anything off. She began the process of weaving my hair around the rollers. This time she used slightly smaller rollers and put more of them in my hair. When she was done she added a smelling solution to all of the curls. This time she made me wait a longer time before beginning the drying process.

While my hair was setting she went to work on my brows. Instead of pulling a few odd loose growths she went to town on them. Every time I expressed my concern on the quantity she as plucking, all she would say is that they needed more shape.

My hands and feet were given their first manicures while my hair was drying. I was told the red polish could be removed easily with polish remover. It seamed silly to put it on for just the weekend, but my mother wanted me to have the total look for my Doctor appointment. She also suggested that I could leave on the pedicure polish because no one would see my feet at school.

Lulu was finally at work removing the rollers. It took her a long time to get them all out and to adjust the results. I was not allowed to see my reflection, but I could see the curls hanging on the sides of my face. These were more pronounced curls than the previous wavy curls I received in my last appointment.

Her assistant Tania went to work on my face. She was obviously a pro, because it only took her a few minutes to work her skills on me. She painted my face with speed and precision. She really didn't ask me any questions or make small talk. She was polite and gentle, but also all business.

My marathon appointment was finally nearing the end. Lulu was very much enjoying the suspense of my makeover and took my hand and walked me over to a full length mirror.

"Ready?"

"As much as I ever will be."

"I introduce Taylor the débutante!"

I opened my eyes and couldn't believe I was looking at my own image. Not one inch of the vision reflected anything remotely close to male. I knew I would look very feminine, but I looked every bit teen girl. I reached up to touch my mass of curled hair. It felt a little stiff and I couldn't get over how curly it looked.

"Taylor, in a couple of days your hair will feel softer and the tight curls stretch a small amount. Don't you just love it?"

"I'm stunned. I look amazing, but this is so over the top. Look at my eyes."

"They are beautiful, don't you think?"

"For a girl. My brows are so thin and arched."

"Exactly. You make a stunningly perfect girl."

"What about school, remember!"

"I thought you would be thrilled with them. I doubt that one little thing will change peoples view of you. You can always use an eyebrow pencil to fill them out if you feel the need."

"Lulu you did a mind blowing job, but I just never thought I would be so completely transformed."

"Isn't this so much better. You are certainly going to turn heads."

"That wasn't my plan."

"Just think of it as a side benefit."

When my mother saw the final results she looked thrilled. The satisfied look in her expression was unmistakable and she gave me a hug.

"I wish Nina was here now to see how gorgeous you look."

"She would probably be surprised just like me Mom."

"Maybe, but I think she would love to have been here."

Lulu interjected, "Can I take a picture. I really would like to have one for my portfolio."

"Will anyone else see it?"

"Occasionally people look at my portfolio, but you should feel honored to be in there. I only put in the most beautiful hair styles. Anyone who looks will just think you are a ravishing hair model. I won't put your name in there."

"Fine."

She snapped off about a dozen shots and even took a couple with me and my mother. She promised to email us copies of all of them.

It was time for Dr. Gordon so we paid the large bill and headed out to the Doctor's office.

I was very conscious of my environment as we made our way. I was less concerned about being recognized as I was what people thought of my new look. In the short walk to the car, I noticed a few glances in my direction. Nothing creepy, but I was drawing positive attention. It felt different than in my first excursion out. That time I was still concerned about getting found out, now I was just trying to take in the new sensations.

Dr. Gordon was briefly speechless when I entered her office. The magnitude of my changes were clearly beyond her expectations.

"Taylor, I would be lying if I said I wasn't surprised by how you look. I expected you to step things up after our discussion last week, but what I see before me is a lovely young woman. Is that how you feel?"

"The feelings are difficult to describe. I do feel pretty, but so many of my nerve endings are on fire."

"Does it feel good to you?"

"Yes, but I know it shouldn't. This is fun for me, but I am a boy."

"I don't see a boy. Do you feel like one right now?"

"You keep asking how I feel. I just don't know. A month ago I would never have thought this was possible. Now I am strutting around town like a chic. It's so surreal."

"That's why you came to me. You need to sort these emotions out. With some boys it is just a phase or sexual thing, for others it is something much more. I didn't expect you to figure it out so easily. That is why it is good for you to spend some quality time experiencing a range of female emotions. Only then, will you be able to adjust to your needs."

"What ever it takes to convince you that I am worthy of recommendation for Northwestern."

"Taylor that is important, but I am more concerned with your long-term emotional health. The school thing is just part of the picture."

"Yes, but we have a deadline."

"From what I see, the deadline should not be an issue. You are obviously committed to spending some quality time as a girl. Over the next few weeks while you are exploring your gender, we should be able to get a good picture of your viability to enter the University as a transgendered student."

That's great. I am very committed to becoming a Wildcat."

"Just focus on yourself and try and to experience the world from your new perspective. Let yourself be you and don't try and do things just because you think it is the right or wrong way to act. There are no correct feelings, just let yourself go."

The rest of the session was we jumped around about topics ranging from memories of my father to my relationships with my best friends. The next meeting would surely have more new territory to explore.

After the appointment we headed home for a light lunch before heading down to Old Orchard Mall. Old Orchard is an outdoor shopping mall and about half way from our house to the Northwestern campus. There were many options at the mall for cosmetics, but my mother parked the car just outside the entrance to Bloomingdales. She told me that Bloomy's was a little more expensive, but always had the best cosmetics and cosmologists.

Despite the complete transformation, I still felt like a foreigner as I walked through the bastion of the female world... the cosmetic department. It was an area no boy would ever find himself wondering through. I felt confident in my appearance, but I lacked a fraction of the knowledge of a girl my age. I had only been dabbling for about a week and that had been with the basics.

My mother tracked down a sales lady that she had worked with before. She primarily represented MAC and Clinique cosmetics. Sasha was about 30 and a very attractive woman with similar dark hair like mine. She remembered my mother's name and was happy that we had sought her out.

"My daughter has finally decided to breakout of her tomboy ways and needs to build a makeup set from scratch. Up until now she has shared my makeup, but she is finally trying to be a real woman, so it's time she had her own cosmetics."

I had to hold back a laugh when she uttered the last comment.

"Well Taylor, your makeup today appears very nicely done. You seem to know what you are doing."

"I had help today. I'm really just learning what goes with what. I don't need that much."

"Sasha, Taylor needs your help building a kit. I want her to have appropriate makeup for daytime and nighttime looks. She doesn't need anything too dramatic, but I want her look to have a classic young woman’s appearance. I want her to reflect feminine beauty, but not in a radical way. Some of the girls in her school look scary, I just want her to look pretty or maybe just a touch seductive. She needs to see herself as a desirable young lady. It's time she stopped acting like a boy."

The second time she made this comment about my fading manhood, I was not as amused.

Much of my current makeup was removed and replaced with samples from the store. She demonstrated multiple alternatives and color options. They all created looks I could never have dreamed possible. When she was finished she replaced my makeup with a combination that was just a little more dramatic than what I had come in with. It made me look a year or two older.

My mother even asked her if their was a fragrance that was now popular with teen and twenty-something set. She mentioned a new product that was the first from the Selena Gomez line. She directed us over to another agent to test that product. The perfume smelled like raspberries, vanilla, and chocolate. It was very enticing and pleasant to the nose. I was now not just looking like a woman, I was now smelling like one too.

When we departed the cosmetic department I had two large bags of products. The tab for these purchases were beyond belief. I argued with my mother about making such a large expenditure. The whole purpose of my dressing charade had been to get me a scholarship to save money. Now we were spending a small fortune on making me a convincing girl. I just didn't understand why I would need so much.

I was ready to depart, but we made one last stop. A few minutes later I had a Kipling purse hanging from my shoulder. It was probably just about the least expensive bag they sold, but it was both functional and casual and matched my outfit. It came in four colors and my mother had me pick the one I liked best. I selected a royal blue bag, which was very bright, but less so than some of the more neon options. I put my wallet and a few cosmetics in the bag. My mother took the brush from her bag and added it to my collection.

We were finally off to Northwestern. My energy level and enthusiasm spiked when the campus began to come into view. It was not a regular class day, but the campus was loaded with students scurrying about. With the warm weather there were many students camped out in all of the sunny areas. I had been here before, but that had been before I was seriously thinking I might go here.

I tried to visualize myself as a student, but it was hard to separate my feminine appearance from being a student. I looked mostly at the female students and wondered if I might be confused for one of them. It was never my intent to attend school as a coed, but I could not visualize myself as one of the male students. The intense emersion into the female gender was starting to play tricks on my thought process. I was afraid I was getting too comfortable in the roll-playing. It started as a secret fantasy that I had an opportunity to experience guilt free, but now I was starting to think like a girl as well.
 
 
We made stops in the union building, biology department and stuck our heads in and out of most of the buildings on the quad. Mostly we just walked around aimlessly. The time seemed to fly by, but I enjoyed strolling around in the warm spring sun. It was a new, but nice sensation feeling the breeze tickle my naked legs and occasionally blow up my skirt. The sun was fading when we made the decision to head to dinner at Koi. I had been there many times before with my sister and mother. We always managed to try something different on their fusion Japanese menu.

We probably should have gotten there earlier, because when we walked in there was already a crowd waiting for tables. Apparently there were two very large dinner parties that had taken up a good chunk of the normally available tables. The waiting time was estimated to be 30-45 minutes. We really wanted to eat there so we decided to wait.

We moved into the lounge area away from the reception desk. At least in there we had a chance of finding a temporary seat. When we entered the lounge my mother immediately made eye contact withy a Doctor she knew from Evanston Hospital. I had never met him before, but it was obvious my mother knew him pretty well.

"Taylor, I have to go over and say hello to Dr. Franklin. Why don't you come with."

"Mom, I think I will wait here."

"Honey, remember you are supposed to be social and interact."

"Okay, Okay."

We weaved our way over to say hello. I followed behind my mother nervous to meet one of her friends. It crossed my mind that if he knew her well enough, that he might know that Taylor was her son, not daughter.

I should have realized that Dr. Franklin was not there alone. No sooner than I was introduced to the Doctor, I was standing face-to-face with his son Jake. The Franklin's were doing a father-son dinner. As it turned out, Dr. Franklin was divorced and he was just meeting up with his son for dinner.

I was ill prepared to meet a boy close to my age. I didn't even know what to do. I had an awkward frozen moment before I said "Hi."

Jake's dad proudly told us that Jake was a senior at New Trier and would be heading to Michigan in the fall. It was clear that Jake was much more comfortable meeting me than I was him. Our parents seemed to dominate the small talk and I think my mother was happy that she ran into him. The nature of the conversation seemed to be more social than a typical co-worker contact.

After a couple of minutes of chatter, Dr. Franklin suggested that we join them. They had already waited close to a half hour, so they would be able to get seated very soon. My mother acknowledged my skittishness and looked to me for approval. She really wanted the opportunity to get to know the Doctor and the expression on her face almost looked begging.

"Mom, I know you wanted some quiet time to spend talking about a few things with me, but I guess it might save us some waiting time."

"Settled, you and your mother will be our guests for dinner."

When we sat down, Jake and I were paired up at one corner of the table and our parents were across from each of us. Before our beverages had even arrived my mother was calling Dr. Franklin by his first name Lester. Through most of dinner my mother chatted with Dr. Franklin. and left me to find conversation with Jake.

At first, I had no idea of what to talk about. I didn't know what to discuss, because most of my past life would make no sense. I tried to steer most of the early conversation to his story and his college plans. I was happy to learn he was also a big soccer fan. His favorite team was Spain, which was my Italian team's biggest rival. We got into a playful fight over which team was better. We both were amazed how much each of us new about world soccer. He loved playing soccer, but New Trier was so big that he didn't think he would play much if he had gone out for their team. He was a decent baseball player, so in the spring he played third base for that school team instead.

After my initial skittishness, I began to get more comfortable talking with him. We found we had other things in common. We both liked to run, we had similar music tastes and we even had a lot of the same colleges on our wish list. Jake was obviously pretty bright, because he got into over half the top schools he had applied to. He chose Michigan because it had a great business school and was just far enough from home. After his parents divorce three years ago, he wanted to temporarily find a little peace out of arms length of his folks. He was still close with both, but the bitterness was still lingering between them.

The conversation got a little uncomfortable when we started talking about our friends and social lives. I used my mother's line that I was always kind of a tomboy and now I am trying to come out of my shell. As a result I was not very experienced in the social world. He seemed both surprised and intrigued by my revelation. He even asked if I had anyone special in my life at the moment. He was now clearly flirting. I think I got flustered when the discussion turned in this direction.

"It's hard to imagine that someone as pretty as you could ever have been a tomboy. I could see you as an athlete, but you are way to refined to have boyish tendencies."

"Thank you, but I really have been very closeted. I have focused on mostly school activities and have not put any energy into dating. I've been happy, so I am okay with that."

"Me too. I am not trying to sound like a macho idiot. I did have a girlfriend for a while, but we split about two weeks ago. I have not seriously dated that much other than Grace. Until about 2 years ago I was overt 5 inches shorter. I sprouted a lot since I was a sophomore."

"How tall are you now?"

"I think about 5'11''. I am just about an inch or two taller than you in those heels you are wearing. Until I grew, I was always shorter than the most of the girls. Probably shorter than you. You are pretty tall."

"Am I too tall?"

"Not for me. I was not real popular until I sprouted a bit. I would never have had a chance with a girl like you."

I thought I was being cute when I said "Two years ago you would definitely not have been my type."

I was the only one who understood my humor. I could tell that he had no idea what I was saying. I think he must have thought I was implying that today maybe he is my type. I may have inadvertently turned a green light on in his mind.

"Taylor, this may sound ridiculous, but I was wondering if I could ask you a favor?"

"Sure, what do you need?"

"I understand if you can't do it, but next weekend I am going to my cousin's wedding. She is on my mother's side of the family and I originally RSVP that I was a plus one. I really don't want to go alone and would love to have you go with me. It's at the Four Seasons downtown and should be a first class affair."

I was startled by the directness of his question. It was one thing to be flattered by his attention, but it was a whole other thing to be asked out on a date. I had a hard time composing my next thoughts.

"Jake, you seem to be a really nice guy, but like I said, I am a social amateur. I am not good in those kind of environments, and besides it's only a week away and I don't have anything appropriate to wear for a downtown Saturday night wedding."

"I would make sure I never left your side. You wouldn't have to meet that many people."

"It sounds like a nice affair, but it's Saturday night at the Four Seasons. I really don't have a dress for something like that."

I thought our discussion had been private, but my mother temporarily interrupted her conversation with Dr. Franklin to jump into our discussion.

"Taylor, I think your sister has a beautiful formal dress that you could borrow if you would like to go."

I wanted to kick her under the table. I had told Jake it would be fun, but the dress was the big obstacle. Now my mom was removing that hurdle. Why would she want me to go out with a boy?

While feeling very uneasy, I reluctantly agreed to go with him. He was a nice guy, but then so was I. He was so excited that his father had to get into the discussion to calm his momentary euphoria.

We exchanged numbers and addresses. It was agreed that he would pick me up at 5:00. I was numb from the realization that I was now going to go through another ritual of life in the female world.
 
 
The dinner had actually been rather pleasant, until I was thrust into that intimate association. It was one thing to enjoy being feminine and attractive, but a completely different thing to be playing the part in a relationship. This boy had is sights on me and I was now going to be his date. I had hardly dated girls and I was already going out with a boy. I knew Dr. Gordon wanted me to experience a full range of female emotions, but this was off the charts of what I had signed up for.

When we finished eating and said our goodbyes I didn't no how to act. I ended up giving Jake a very casual hug. I could see his pleased smile as we parted and left.

"MOM, how could you do that to me?"

"You will have a great time. He is a nice boy and you both seemed to hit it off so nicely."

"He thinks I am a girl. This is not funny."

"Of course he does. You are just going to a wedding with him. That will be a perfect situation for you to learn what being a girl is all about in an environment with no concern for crossing paths with schoolmates. You are going as a guest, not the bride."

"How am I supposed to act around a guy that has eyes for me."

"You did fine tonight. A wedding with hundreds of guests will probably have even less opportunity for intimacy."

"I can't do it. This is too weird."

"Tell me you didn't think he was nice. You looked like you were enjoying his company as much as he was yours."

"He's cool, but that's not the point."

"Just be friendly and take the new feelings in stride. It will probably be enough to convince Dr. Gordon to sign off on your recommendation."

"What do I do if he wants to get extra friendly?"

"Why...is that something you are thinking about?"

"No way, I just know how guys think."

"I am sure he will be driving you straight home from the affair, so I wouldn't concerned your pretty little self."

"It's just..."

"One evening isn't going to change who you are. Relax and I bet you both have fun together."

"Are you doing this to me because you like his dad?"

"Honey, I would never do anything that I didn't think was good for you. The fact that his dad is also interesting, is a bonus. You focus on Jake, I will see about Lester."

When we arrived home I was just regaining my composure. My jitters were finally being replaced by the safety of home. I received one last surprise a short while later when I went to remove my makeup and get in my pajamas. All of my PJs had been replaced with girls pajamas and nightgowns. There wasn't even one old pair left in my drawer.

My mother was not bending and reminded me that for the next few weeks I am supposed to spend most of my non-school time roll-playing. That in her mind included sleeping.

I was still warm from the unseasonable weather and all of our activities. I selected a skimpy tap pant combo that had a spaghetti string cami top. It was pink and very silky. I would have chosen a less colorful alternative, but this looked to be the summeriest choice.

The first few times that I wore something so absolutely feminine it had brought me a degree of sexual excitement. Now I was just marveling at how nice it felt caressing my smooth skin and how almost normal it felt to be dressed this way.

I was thinking about the extreme range of activities I had traveled in this unusual day as l rested my head down onto my oversized bed pillow. My last thoughts were of my upcoming date as my consciousness faded to black.

I could not remember my dreams when I awoke early the next morning. My mind was thinking about weddings and wedding dresses when my fog cleared, but I could not recall any of the details. I decided to go for a run to clear my mind.

I put on my running clothes and shoes and headed down the stairs. My mother was already up and having coffee in the kitchen.

"Surprised to see you up already, Taylor."

"I slept well, but need to get in a run this morning. I think I might make it a long one."

"That's fine, but aren't you forgetting something."

"What?"

"You know. Over the weekend you need to express a certain look."

"While running?"

"Girls run too!"

"What can I do?"

"Your sister used to jog a lot. I am sure you can find a job bra and one of her sports tops. Put those on with your breast forms."

"Really?"

"Yes, You can wear your hair up in a high ponytail and put on a little of your new waterproof mascara on your eyes. I have some tinted Chapstick and that should be enough to give you the right look. I would hurry up if you want to avoid the late morning crowds on the trails."

She was right, I didn't want to see anyone I knew out there so I dashed up and made the quick changes.

"I bet you will be one of the fasted girls on the trail."

"That's funny mom. Hopefully fast enough that no one can keep up with me."

I was quickly making my way down the Greenbay running trail. At first I was looking all around to make sure I didn't see nearby neighbors or friends. A couple of miles into my run, I got into my groove and stopped fretting. I was moving along at a fast but not unusual pace for me. I found that I had to slightly adjust my running stride because of the breast forms. They added a significant amount of weight and bounced around more than I was used to. I ran in a more upright style with my shoulders slightly pulled back.

This made my breasts slightly more prominent, but it was much more comfortable.

I ran about six miles and passed the entrance to the Ravinia Music Pavilion along the way. I saw many other runners, but the jog went without incident. I am sure I probably pissed off some male runners as I flew by them at a faster pace. I always hated it when an occasional great woman runner would pass me when I was jogging. Now I was able to turn the table. The fun of passing guys even added a little extra enjoyment to the run.

I felt great when I got home. After cooling down, I took a soothing shower. I even washed my breast forms, which had gotten slightly sticky. I decided to dress in a very casual outfit. I wanted to just look like a typical girl of my age. I didn't want to appear like I was trying to prove anything; but rather, I wanted to look invisible in a cute way.

I put on my padded briefs and full coverage bra. I covered my foundation with a pair of high riding jeans and a clinging grey sweater. I parted down the middle my now wavy curls and I pulled the left side back behind my ear.

Before heading to the family room to work on my homework I added a small amount of makeup to brighten my face. I was pleased that I looked attractive, but not made up. It was an everyday look that I always admired on the cuter girls at school. I always hated when they overdressed or looked overly prissy. I was already beginning to establish my female style persona. So much of this intense immersion experiment was coming almost too easily for me.

The rest of the day I spent at home on schoolwork and catching up on a couple of my favorite shows that we had recorded on the DVR. I helped my mother make dinner, which I rarely had in the past. She told me with college around the corner that it was time I increased my skills in preparing food.

At every opportunity she coached me to improve my female presentation. Little things like choice of words, voice inflection and hand and body movements were force fed into my brain. She would compliment me when I naturally expressed myself in a girlish way or reacted in a way that the old Taylor would never have had. When this whole transgender strategy began I was initially shocked by my extraordinarily convincing physical makeover, but now I was almost as surprised by how easily the rest of me had changed.

To be continued….