Part 2---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. It leads him down a road of self discovery.

-----------------------------------------------------------------------------------------------------------CHAPTER 3:

My mother was waiting for me in the Doctor's lobby. She was anxious to know how it went.

"Dr. Gordon is very nice. We had a good chat and she wants me back Wednesday at five."

"What did she say?"

"Well our sessions are very private, but we talked mostly about my background and our family. We hardly talked about how I was dressed or any of that kind of stuff."

"Nothing about how beautiful you looked?"

"She complimented me, but not much more than that."

"I guess its good she wants to see you again so soon."

"She's easy to talk to and very upbeat. Maybe she can help me for real to get through the mental aspects of this program. If I go forward and try and get into this group, it might be a good thing that I can talk to someone privately about it."

"You always have me Taylor."

"I know that, but Dr. Gordon has no vested interest and has helped others deal with their conflicts and stress."

"I'm just glad it went well. We still have a lot of territory to cover to get you into Northwestern."

"Can we go home now so I can shower?"

"What's your hurry. Let's take advantage of the opportunity."

"What opportunity?"

"You are going to need a few outfits for your followup sessions. You can't go back in the same clothes every time."

"I don't need more girly clothes. I made my point today."

"You didn't even discuss how it made you feel. Until you get her blessing, you are going to have to continue to emphasize and at a minimum express that part of your personality. "

"I am seeing her after school on Wednesday. I can't come back looking all made up."

I don't expect you too. Sometimes even girls are more casual. You just need a few mix and match items that will accent your gender-bender impression. When school is out it wouldn't hurt you to express yourself with a more colorful shirt or something else that looks cute. I am certainly not sending you off to Lulu's before each session. I just don't want you to waste the momentum."

"So what do you have in mind right now?"

"Lets go over to Woodfield Mall and pick out a few things. It is a 30 minute drive from here and I guarantee you won't run into anyone you know there. The place is huge and we can do some mother/daughter shopping. This way you can help pick things out."

"I think you like me this way."

"Well when I saw how stunning you turned out at Lulu's, I did kind of enjoy it. Most boys would not look so naturally pretty with such ease. As long as you are going to need to explore this side of you, I don't see why we can't do it right."

"Mom, you have read way too much into my past isolated dress-up experiences. I don't mind talking with the doctor about how this makes me feel, but I didn't just wake up this morning having turned into your daughter."

"I am only saying that this college strategy is going to take a long commitment to be successful. As long as you are going to have to subject yourself to new experiences, why not make the best of it. You have always been prided yourself with your fashion choices, so why not put some of that energy into selecting a few new things."

"Do we have to do it today? I have only seen the psychologist once."

"Today is the best day. We have nothing planned for the remainder of the day and thanks to Lulu you will almost completely blend in. It is certainly better to go shopping like this than in boy mode."

"That's true. I guess we could go today, but why do you say I only 'almost completely' blend in? I think I look and am dressed pretty convincingly."

"Honey, you look amazing. The only thing you lack is a little shape like your sister."

"And Nina sure likes to flaunt it."

"Don't make fun of your sister, Taylor. With just a little more on top we could drop the 'practically'."

"Sorry mom. I would help if I could. Those things just don't grow like my hair. You will have to settle for me being the flat chested daughter."

"Since you said you were willing, I think we should fix that."

"What? I know you are a nurse, but now you are scaring me."

"Settle down. As a nurse I often have to refer patients to a place to get medical breast prothesis. The best place to get them is Schwartz Intimates, and it is on our way.

What is a Medical Breast Prothesis?

"Don't play dumb now. You want to go to med school? A pair of small falsies will complete your appearance."

"Falsies! Are you serious?"

"A small understated pair will help your appearance and make it easier to find you a few tops for your upcoming appointments."

"How am I going to explain needing those at the store?"

"Do you think you are the first man or boy to shop there? Besides, the way you look, I bet they never even say a thing."

This day seemed to be spiraling out of control. I never could have imagined that I would get in this deep, but I was letting myself get pulled in. I should have put my foot down, but part of me was enjoying the day of feminine immersion. My makeover had erased my fear of getting spotted and mom's plan to drive all the way to Woodfield felt equally safe.

As my mother had observed, I did wonder from time-to-time what it would be like to dress-up like a girl. I had dressed a few times when I was younger, and I had not completely outgrown the urge. A couple of times when no one was home I had even put on some of my sisters lingerie. I was always careful to put it right back, but the experience only seemed to re-enforce my interest in dressing like a girl.

The events of today just kept falling into place like dominos. At any point I could have said NO and I know my mother would have stopped her persistent pushing. She had never been abusive and while I initially expressed more reluctance, nothing had truly been forced on me. I always showed some light resistance, but I ultimately complied. I wasn't sure why I wanted to do this, but I was more than a little curious to see how it would feel.

I contemplated that maybe I could get it out of my system by experiencing the full effect. If I didn't try at least once, I would continue to question myself. I was prepared to let my mom have her fun with me today, because it was in a strange way fun for me as well.

The idea of getting medical breast forms had never crossed my mind before. When I wore my sister bra, I pretended I had breasts by stuffing sox in them. However, I was still dumbfounded by her suggestion and almost speechless.

"You really think that's necessary?"

"No, but it will be worth it. You will feel more confident if you reflect more age appropriate development."

"They will really sell me falsies?"

"Honey they will not just sell them to you, they will properly fit you. Money is money and I have referred them a lot of cancer patients. It wouldn't surprise me if they gave me a discount."

I just let her drive to the Schwartz Intimates store without saying another word. I didn't want to sound happy about going there or say anything that might make her second guess her idea about stopping.

I felt the same level of anxiety entering the store as I had entering Lulu's earlier in the day. I didn't know what to expect and I would be opening myself up to strangers. We were not the only people in the store and I just wanted to stay out of eyesight. I had never gone shopping in a place like this. On a few occasions I had looked longingly into the Victoria Secrets windows, but never had the courage to walk through the store.

My mother spoke privately with a middle aged woman in the store before the two of them called me over. The woman's name tag said Sally. Sally gave me a small smile before directing me to a changing area.

“Young lady, please strip down to your panties please.”

I didn’t know why I needed to take off my tights, but I complied. I was actually shaking from nervousness or possibly a slight chill in the air when she returned with a tape measure. I didn’t say a word as she measured me in virtually every direction.

“Your mother said your name is Taylor. That is a very pretty name.”

“Thank you, it’s my real name.”

“Well Taylor, you certainly take good care of your body. We should be able to help you where nature has not. With a little padding and some enhancements, I think you will be a size 8 or maybe even a 6.”

“Can I put some clothes back on now?”

“First thing we need to do is make you a little smoother in front.”

I thought my mom wanted me to get falsies.”

“First things first.”

Sally handed me a lightweight black garment.

“This is a thong, but it should work as a gaff to hide your boy thing. Slip off your jockeys and pull this up your legs. Before you get it all the way up, tuck your penis up between your legs. It might help if you reclined on the bench so you can push it all the way back. This will hold everything in place.“

My thing was not that big and it easily disappeared between my legs.

“Now put on these panties. These are full briefs and even have a place for hip pads to give you a little more on the bottom. Your mother is in the other room picking out a few additional styles for more everyday situations.”

With the panties covering my lower section I was now missing my most manly aspect. I knew my flat chest was next to go.

“We don’t want to give you too much on top. Your mother is mostly concerned with you blending. You already look very sweet, we wouldn’t want to ruin that image. Based upon your measurements, I have some very realistic looking silicone breast forms that should look very nice on you. I think we will give you a modest ‘B’ cup size. If you ever want to look a little fuller on top, you can just wear a more padded bra style.”

I held my arms out as she slid a satin Bali bra over my chest. After hooking the two clasps in the back, she showed me how to properly position the forms in the full coverage cups.

“Now isn’t that better. You will look 100% better even in boy clothes.”

She was right. I now had a teen girl’s body to go with my facial makeover. I knew it was me, but even I could not see through the feminine facade. I felt my manhood getting uncomfortable under the restrictive garment. I was getting sexually turned on by my own reflection. The fantasy thoughts of dressing up had gotten me excited before, but I never expected to take those secret feelings out in public.

When my mother returned to the changing area with her hands full, she stared at me with a sly grin. “Taylor, doesn’t that make you feel so much prettier. There is something re-assuring about wearing a bra. Isn’t it wonderful to wear one for the very first time?”

The way she said that made me wonder if she somehow knew that I had previously tried on a couple of Nina’s bras.”

“Mom, it looks so real, but I can’t believe I am wearing one. This is so way beyond one of my Halloween costumes.”

“Well honey, just let yourself enjoy it. Today is a learning experience and will provide you with emotions you can discuss with Dr. Gordon. Today is your girl day, and when it is over you can go back to being my boy. Until then, try and let yourself feel what it’s like to be my daughter.”

“I am more than a little scared how easy it has been for me to be transformed. I admit that the role-play thing is kind of fun, but I shouldn’t be doing this.”

“There is nothing wrong with you letting some of your repressed emotions emerge. Remember, those emotions are what may get you into Northwestern. I wouldn’t have suggested for you to have to taken it this far, if I didn’t think it would be beneficial on some level. You will be able to relate to the students in the program much better after today.”

“That’s true. I have never felt quite like I do right now.”

We remained in the store for another fifteen minutes or so as I tried on a few more bras and some additional lower body foundation enhancements. I even tried on a one piece lingerie item that had a built in bra and snapped between my legs. The clothing I wore into the store looked dramatically different with my new lingerie underneath. My tunic top now snuggly wrapped around the new enhanced cleavage and created much more of a stylish appearance. Though the clothing never could have been considered truly androgynous, it was now stylish chic.

When we left the store, we had a lot more than just a bra and a pair of falsies. I really didn’t think I would need more than a couple of items, but my mother had her mind set.

When I woke up this morning I never expected to be spending the afternoon like this. I was focused on my psychologist appointment and not much else. Now I was entering Woodfield Mall strutting around like a cute teenager. My mother was coaching me on the fly. She gave me tips on my posture, my stride and even how to hold my elbows in.

“Where to now, mom? I’m still a little nervous about being here. I know I look alright, but this is all so foreign.”

“I suggest we go to the places your sister always liked. I see an Anthropologie store across from us and I know there is an Urban outfitter here and also H & M. The H & M is very inexpensive and we can get you some stylish accessories and fun pieces there.”

“Those are fine, but lets not go overboard. I only need a couple of androgynous pieces so I don’t have to wear the same clothes to all the appointments.”

“I know you don’t need a full wardrobe, but you don’t have anything. Try and enjoy the experience. We may not have another great opportunity like this any time soon. I would rather get too much than not enough. If we don’t get you enough today, we will have to go back to one of our local malls.“

“You made your point. Let’s start in Anthropologie.”

Anthropologie was not what I expected. It had very nice clothing, but it was all extremely feminine. We picked out a couple of flouncy tops and my mother eyed a few delicate dresses. We headed to to next shop with only the two purchases. We had more success at Urban outfitters. I picked up two pairs of girls jeans that were not ridiculously feminine. The pocket design was more intricate than on my old jeans and the fit was different. The zipper was smaller and they seemed to lift my rounded bottom. One pair was a washed light blue and the other was a unique burgundy shade. I was just happy to find some jeans that fit that didn’t scream look at me.

I wasn’t sure what was next as my mother pulled me into Bebe. This was definitely not a place to buy androgynous styles. Everything in the store was overtly sexy and not a lot of it was everyday casual.

“I want to see you in something that shows off more of your lovely shape.”

“I don’t need anything like that.”

“Relax, today is as much for fun and fantasy as it is for practical. Here are a couple of dresses I am dying to see on you.

The first one was a faux leather style and the second one was a lace sheath dress in the color begonia. The leather dress looked amazing but my mother thought it was a little to racy for a 16 year old. The begonia dress was equally form fitting but more appropriate according to my mother. It was still very flirty, and I couldn’t imagine what I would need it for.

“It looks very flattering on you.”

“Thanks mom, but save your money.”

“I am just having some fun. Maybe we will come back and get it another time.”

We moved on to Lord & Taylor's where we made a beeline to the shoe department.

"You need to have to something besides clunky clogs. Lets look for a couple of pairs that can be worn with almost anything. Nothing fancy, if you need dressy shoes we can come back."

It felt strange having a man hold my foot as he measured me for size. He was probably in his thirties and I could feel him checking me out. When he went into the back to bring out some shoes in my size, I mentioned my uncomfortable sensation.

"You will need to get used to wondering eyes. You are after all, very pretty. The best way to handle it is eye contact. Don't look away. If you make eye contact you are less likely to get ogled. It's going to happen a lot, so don't think about it. As long as you are in a safe environment, it is probably a good sign."

"I don't want to attract guys, mom."

"Sorry Taylor, but it goes with your little fantasy. You will just have to live with that."

The salesman returned with a mountain of boxes. When I shopped for male shoes, I never remembered them bring more than one or two pairs to try on. Now I had at least a half dozen styles to try. I felt bad for the guy I had only moments ago had felt squeamish around.

I had difficulty walking around in most of the shoes. None of them had huge heels, but for me it was challenging to walk in two or three inch heels. The higher the heel the more my feet felt squeezed into the narrower styles. I was grateful to put on a Mary Jane style that had almost no lift at all. All of the other pairs had a more defined heel which altered my posture and walking motion. I had to take smaller steps and my hips needed to be shifted slightly forward.

We ended up with three pairs. I chose the Mary Jane's and my mother selected a tall pair of black leather boots with a pronounced heel and a pair of two-toned leather ankle boots, that also had about a two inch heel.

I was ready to call it a day, but my mother still wanted to go to H & M. She had never shopped there before, but it was suggested by Lulu. Lulu had said that they had trendy clothes at inexpensive prices.

We arrived to a very busy store. It was much more chaotic than at our previous stops. The store was very popular with the teen set and they had racks of funky and edgy styles. My mother was not enamored with the quality of some of there merchandise, but she loved all of the selection. She made a large pile of things for me to try on.

Inside the dressing room I began a private show for my mom. Besides colorful tops, I found myself trying on short dresses and fashionable short skirts. Other than an overside purple sweater, everything I tried on was overtly teenage chic. The store had a young crowd and everything there I thought would be perfect for my female classmates.

The low prices were both good and bad. I was happy that the clothing was relatively inexpensive, but as a result, my mom bought virtually everything I tried on. She even bought some accessories, including belts, more tights, bracelets, necklaces and some dangly earrings. I strutted out the door after buying three large bags of outfits. Inside those bags were multiple skirts, dresses and very feminine blouses. I really couldn't picture myself wearing most of these items to my appointments in an effort to look androgynous. Most of the clothes was decidedly female.

My attempts to temper my mom's enthusiasm went unanswered. I now had a closet full of new things and with most of it, I had no idea when I could wear it. I thanked her for her generosity and informed her that I was tired and hungry. The whirlwind of activity had begun to catch-up to me. I could see my mother fading a little as well.

After loading the giant haull of apparel from our shopping excursion, we went to dinner at Francesca's Tavola in Arlington Heights. It was only about five minutes from Woodfield and we were familiar with their sister restaurants near our home. It was a nice way to end our Mother-daughter afternoon and gave us a chance to reflect on the day.

"Well Taylor, was it everything you expected it to be?"

"What do you mean?"

"I know you have always wanted to to dress up completely."

"Why do you say that?"

"Taylor, I am your mother. There is nothing wrong with you admitting that this was fun for you."

"I didn't ask to do this. We did this for the Scholarship and to get me into Northwestern."

"That's true, but I could tell that at least part of you enjoyed this."

"Some of this was kind of a rush. I did kind of wonder what I would look like if I went all out. Nina asked me last year on Halloween if I wanted to get all dressed up in one of her outfits. I told her no way, but in truth, I have wondered about that since then. I am not sure why, but I have been curious. I know I shouldn't feel this way."

"There is nothing wrong with feeling that way. We talked about this when you agreed to try and get into the TSA program. Lots of boys and even girls enjoy dressing up. You are lucky, you are a handsome boy and also look so natural as a girl. Most boys can not be such chameleons."

"It is weird that I look so real. I like that I look pretty good, but it makes it even more confusing. I guess it will give me something to talk to Dr. Gordon about. I know today was a special day and maybe it will help me get it out of my system. At a minimum, it will be useful in understanding others in the program. It was fun, but tomorrow I am your son again."

"Today was a special day. I think you have handled it very well. I am sure Nina would have loved to tag along today. We both understand that going forward all we need is for you to express an expectable level of feminine charm. We both know after today we will probably have to tone this down our fun."

"That's an understatement. After today, I go back to my old self."

"I agree, but don't forget part of what is on display is your old self. We will just have to keep it mostly under wraps."

"Absolutely, other than for the psychologist, this has to stay our secret."

"Of course."

Chapter 4:

Our dinner was fabulous and it was pleasurable having my first mother daughter experience. It all felt a little like a theatrical game, but I enjoyed playing my part. My mother even coached me on subtle mannerisms like how to hold my hands at the table and my overall posture. Knowing that my time as Ms. Taylor was winding down, motivated me to throw my self into the part. When we left the restaurant, I consciously threw a little extra into the swing of my hips. I was so much more confident in my new persona than I had been just eight hours ago.

Back at home I began the process of returning to my old normal. I stopped in the hall bathroom after bringing in all of the packages. Besides badly needing to use the bathroom I wanted to see my glamorous appearance for one last time. My makeup did not look as good as it had when we left Lulu's. My lipstick was virtually all gone. Despite that, I still looked all-girl and I mugged for myself in the mirror for one last time. I made a couple of girlish poses and I even rubbed my breast forms as if they were real... I heard my mother call and that shook me out of the momentary trance.

"I need to show you how to remove your makeup. Please come down to my bathroom."

It was a little more involved than I expected removing all signs of the makeup. The mascara was oil based and did not completely come off. After scrubbing off the makeup my mother insisted that I put on a moisturizer. When I looked at my stripped face, I thought I still looked very feminine. My curled hair with it's still wavy body gave me a new appreciation for how delicate my facial features really were.

"Taylor, there is no point in you changing before bed, so why don't you just wear those clothes until you turn in later. Lets just spend a few minutes to find a spot in your room for your new things and then you can just watch some TV or finish up your homework. Tomorrow morning you can wash your hair and remove the waves."

"Sure Mom. I still think we bought to much clothes. I don't know where it will all go."

As it turned out my mother cleaned out a lot of my old clothes that I rarely wore or had outgrown. I now had a drawer in my dresser devoted to only girls items. I also had a section of my closet now being adorned by bright colors and dainty apparel. My new shoes took up a big chunk of the floor in my closet as well. I realized that I would have to keep my closet doors closed if I had any friends over.

I felt ready for bed much earlier than on a typical Saturday night. I had experienced a day like no other and while I did enjoy many aspects of it, the emotional toll had left me very tired. I put my outfit from the day in the laundry bin and my breast forms with my new lingerie. I took off the the thong which released my manhood that had been hidden for most of the day. I was going to put on a pair of my jockey shorts and go to bed, but decided to just put the panties back on. I mentally justified it to cut down on dirty clothes.

Chapter 5:

I had slept very well and despite going to bed early, I still managed to sleep in. I woke up in a very aroused state. When I finally pulled myself out of bed it hit me that I was still adorned with the delicate panties. I was surprised by not just what I was wearing, but that there was a large stain in the front of them. I must have done that while dreaming during the night. I didn't have any strong recollections of my dreams, but my dressing experience from the day before was still fresh in my memory.

I immediately removed the panties and headed into my bathroom to shower. My hair looked like a tangled mass of headphone cables. The beautiful image from the previous day was now a fading memory. I took a long hot shower and washed my hair and conditioned it. I dressed in one of my old pair of jeans and a Hunger Games t-shirt.

I joined my mother down in the kitchen.

"How did you sleep last night Taylor?"

"Good."

"What do you have going today?"

"I have a lot of homework, since I didn't get to any yesterday."

"What was yesterday?"

We both had a little laugh after that comment.

"Before you get started you need to brush your hair thoroughly. Now that it is so long, you need to give it extra care. If you brush it more, it will be much more manageable and will have a nicer finish."

"Will do. I assume the curls will all be gone when my hair drys."

"Do you miss them?"

"That's not why I am asking. I want to go to the library."

"The bouncy waves should all be gone. You might have a small amount of wave left, but if you brush it enough it will be almost impossible to tell."

"That's good. I need to keep a lid on yesterday."

"You are only going to have an issue if you make it one. Just be yourself. Don't be so sensitive, you are going to need to loosen up."

"I know. I am just trying to separate myself from the activities of yesterday. I'll be fine."

"I won't say another word, unless you want to talk about it."

"No, I just need to get my work done."

The rest of Sunday and for the following couple of days I was able to return to my daily routine. I thought a lot about Saturday but tried to keep it mostly to myself. In school I found myself occasionally getting distracted. I would see a classmate wearing something similar to what I had purchased or tried on, and I wondered how I would look in it. I even started paying attention to the girls fashions and accessorizing. Rebecca a friend from french class caught me staring at her and it created a very awkward moment.

I told her she looked really nice today and asked her if her boots were new. She thanked me, but gave me a very confused and strange look. After that I was much more careful when I was trying to be observant. Like all my friends, I was checking out cute girls, but I was having trouble with the mind games that wouldn't go away. I was sure it was all a result of my Saturday makeover, but I found the day dreaming getting worse and not better.

Before school on Wednesday my mother reminded me about my 5:00 appointment. I was actually happy to be going, because I wanted to talk about my building confusion. In the first session I was dressed for the occasion, but not much was said about that. I actually wanted to touch on that subject which was getting harder for me to understand.

"Taylor, after school why don't you go home and change. I will pick you up and take you to the appointment. It's too bad you won't look as made over, but it is still important to reflect some androgyny."

"What do you suggest?"

"School day casual. Put on one of your new pairs of jeans and one of the tops from Anthropologie or H & M. You pick. The Mary Jane shoes will add a nice touch to the simple outfit. Also take the rubber band out of your hair and brush it out so it looks presentable."

I nodded affirmatively, but also faked a slightly surprised expression back at her.

"We have to be careful that no one sees me. Even with just those items on, I would be a laughing stock."

"Honey, I understand, but you are going to have to get more comfortable with this. You will have to see Dr. Gordon for the time being. I will be careful, but remember if you try to hide, you are more likely to stick out. Just relax and you will blend better."

When I got home from school I went to my room to change. I spent about 10 minutes trying to figure out which top to wear. I kept holding them up to my chest and looking in the mirror. I realized that none of them would look the same without the breast forms, but I was not going to add that to my selection. My favorite top was a red blouse that was very shinny and oversized. I considered that, but thought it might be too flamboyant and more feminine than I was trying to convey. I settled on a dark blue cotton top that had a V-neck and was more form fitting.

I slipped that on and then put on the jeans. The jeans did not fit the same because my manhood did not have as much space as in my pants. When I originally had tried them on, I had my penis tucked under and the jeans fit more smoothly. I decided they would look better if I did that again. I changed out of my briefs and retrieved the the thong and a pair of my new panties. When I began to put them on I started to get erect. Eventually I managed to get everything in place and put the jeans back on.

The jeans looked better and under the circumstances I thought tucking was a good idea. I put on the Mary Jane shoes before I went into the bathroom to comb my hair. I first shook out my long hair before brushing it out. I pulled the left side back an tucked it behind my ear. A few loose strands fell forward and dangled near my face. I never wore my hair like that before, but it went with the look I was trying to express. The last item I added were studs in both of my ears. Even without makeup, my look was very soft and more than a little androgynous.

My mom picked me up at 4:45 and gave me a once over before I dashed into the car.

"You look sweet, but you know it would have been okay to wear a bra with that top."

"I understand I am seeing Dr. Gordon to get a recommendation and need to show her I have some feminine interests, but I think it would be over-the-top to show up wearing a bra and falsies. That's way past androgynous. I just want her to see that I have some issues that are in common with transgendered people. I don't need to hit her over the head with it."

"I was only saying it, because the t-shirt would look nicer that way. You look just fine, and the top looks very pretty with your jeans and shoes."

My second session focused more on why I was there in the first place. After some cursory hellos and a couple of shallow questions she came right out and asked me why I wanted to see her. The blunt question left me at a loss for words. I thought her questions would be more leading or simpler to answer, but this was such an open ended inquiry.

"I, I... to talk about things, I guess."

"What do you want to talk about?"

"Anything."

"Okay, talk."

There was a long silence.

"It's okay to say anything. Whatever you want to talk about is fair game. You must have something that you want to talk about."

"I just thought you were going to evaluate me."

"Why? I am here to help you."

"My mother suggested I come."

"There must be a reason."

"Because I am not like every other kid."

"Well that's a start. How so?"

"I just have some odd feelings and unusual likes."

"Tell me about them."

"It's not that easy."

"Take your time... I know it's hard sometimes to talk about personal feelings."

"Well, I used to like to dress up with my sister and on Halloween."

"What about now?

"My sister is off to college and I don't do Halloween anymore."

"Is that hard for you?"

"I do miss my sister being around, but we still talk."

"You know that is not what I mean. Is it hard for you not to have someone to dress up with or an excuse to feel like a girl?"

'I never thought about it that way. I do wonder about feeling that way every so often. Maybe that is why I like my hair is so long. I enjoy caring for it and like the way it looks."

"You could have short hair and still feel that way about it. A lot of girls have short hair that is very pretty. Does it make you feel pretty?"

"I don't know. Do you think my hair is pretty?"

"What I think is not as important, but I do think you have lovely hair. Last Saturday you seemed to have made it up for me to look very stylish. I saw that you were wearing makeup as well. Does looking like a girl make you happy?"

"Happy? I was just expressing myself."

"To who?"

"I guess to you."

"Is that what you wanted me to see. I mean do you want me to see you as a girl?"

"I think I just wanted you to see that part of me. I don't normally look like that."

"You looked pretty comfortable that way."

"It was okay... you are easy to talk to."

"Thank you. Does it get you excited or aroused when you dress up?"

"I don't really dress up like that. I did get aroused a little, but after a while I was fine."

"You are wearing some girls clothes now. Do you feel at all aroused."

"Not now. I feel normal."

"Do you feel normal when you are dressed like a boy?"

"Uh, yes, but lately I have been thinking about this more."

"I assume that is why you are here. I know it must be confusing to you, but you are not alone. It won't necessarily be easy, but we will learn to understand this more and help you adjust accordingly."

"I appreciate that."

"That's it for today. I will see you next Saturday. You can come however you like, don't worry about what I might think about your appearance."

"See you Saturday, bye..."

"Well Taylor how did it go today?"

"We just talked a lot. She is really getting into my head."

"That's what Psychologists do. Did you finally talk about your feminine side?"

"Yeah, but it was more of a discussion than an evaluation."

"What did she say about it?"

"She really didn't say anything. She asked a bunch of questions and just let me talk."

"What did you say?"

"Mom, I talked about a lot of personal things."

"And?"

"It was mostly good, can I just leave it at that. She says that it will all take time, but she can help me through it. That's probably a good sign for me to ultimately get her college recommendation."

"Do you want to go out to Dinner?"

"Mom, it's not like Saturday. I am not going to go prancing about looking like this...especially around here."

"Okay, I will re-heat some soup for dinner. We should both watch our figures."

Chapter 6

When we got home I stayed dressed as I was. I thought about changing back, but since we were home I didn't feel the need too. My mother never suggested that I change either. I found myself even playing with the loose strands of hair that hung from the side of my face. I started getting in the bad habit of twisting them around my finger.

At school on Thursday and Friday I continued to play mind games about the girls in my classes. I started grading them on their outfits and overall fashion sense. I wasn't just focused on the prettiest girls. I was evaluating the appearance of all the style conscious girls. I probably learned even more from girls that managed to look really nice, even if they did not have a lot of natural beauty. My compulsive day dreaming was getting me concerned and keeping me from engaging with most of my friends.

It was becoming harder to stay in my normal everyday routines. I would often scan my girl's wardrobe, but I generally avoided taking any of it out of the closet. I had more than a few urges to slip into some of the new items, but it still didn't seem like an appropriate thing to do. I had started jogging more to create some distraction and I also focused more on my schoolwork to keep my grade point high.

By Saturday, I was anxious to select clothes from the taboo section of my wardrobe. I was even tempted to wear my bra and breast forms. I even put one on, but thought that my shape might send out too strong a statement. I enjoyed feeling more feminine and pretty, but trying to physically alter my appearance for the Doctor just felt like overkill. All I needed was a recommendation to apply to the TSA program and I figured my basic dress up behavior should be sufficient. I removed the bra and forms, but did wear panties along with the thong. Whenever I had feminine clothing on, it just felt re-assuring to be flat and secure in the crotch area.

I wore a yellow sweater that was ultra soft and had a very wide neckline. It had a tendency to slip a little over one of my shoulders. The sweater matched nicely with my new jeans. I slipped a small pair of hoop earrings into my lobes. They were hardly visible under my mass of hair and I thought they complimented my look. I wore the same ankle boots I had worn the previous Saturday. I brushed my hair down the middle in an attempt to make it look more presentable. I was a little disappointed with my hairstyle and inability to do much with it.

I was still about a month away from getting my driver's license so my mother still had to take me to the appointment. She was glad I had selected my outfit on my own, but gave my hair a funny once over.

"I am going to have to show you how to fix your hair better. It probably would also be a good idea to give you some basic makeup skills. You look nice, but with just a little more effort you would look 100% better. It's too late for that now, but this week we have to find some time for me to show you a few things."

"Sorry Mom. I guess there is a reason I don't have Nina's skills. Sis has been doing this all her life. I am just trying to create a temporary more feminine appearance. "

"Still, if you are going to be leaving the house like this, you should look your best. There would be nothing wrong with you wearing some of the other things we bought for you to give your clothes better shape. That sweater would look nicer and slide around less if you had more in front."

"Slow down Mom!"

"I'm just saying, you would blend even better."

"Whatever.. we have to leave now."

"Hold on for just one second."

After dashing down the hall, my mother quickly emerged from her bedroom and ordered me to stand in front of her. She grabbed the front mass of hair on both sides of my head and pulled them back and up behind my head. When she was satisfied, she attached a giant sized hair clip to hold the two sections together and in place. The effect was to create a sort of high pony tail that cascaded down to my neck. The remaining hairs still hung on the sides from under the pulled back strands. The effect was much prettier than before and ultra feminine. I would never have thought of that look or known how to achieve it.

It was a big improvement, but once again my hair went way over the edge of being androgynous. The effect also made my hoop earrings much more visible. I was slightly apprehensive to go out this way, but our time was running out. We made our way to the Doctor's office.

Today’s appointment started off on a discussion of my fist memories of feeling a little different. We talked about my experiences with my sister and also my first sexual feelings. I had never equated the two, but I did recall early memories of getting excited when playing playing around with my sisters clothes. I could not pinpoint my first recollections of getting aroused without some associated female apparel. I knew that cute girls excited me, but I guess I always liked well dressed girls over sexually explicit images. I preferred to look at them in Glamour magazine rather than in Playboy.

The discussion was interesting but not what I expected. We hardly talked about what was going on in my life at the moment. It was almost all about the past. I seemed to be learning more about myself with each new discussion and revelation. Even though I didn’t directly discuss my current emotional confusion, I still was beginning to feel more comfortable as our time came to an end. It was a brief feeling of calm.

As I emerged from her office to greet my mother in the waiting area, I was shocked to see a girl I knew from school. I had gone to school with Julia since our elementary school days and though we were not particularly close, we both knew each other very well. To a stranger my appearance would hardly have registered, but in my partially transformed state it only took her a moment to recognize who I was. The grin on her face sent a chill down my spine. My mind alternated from wanting to scream and wanting to run.

With my heart pounding I greeted her.

“Julia, what are you doing here?”

“Same thing as you. I see Dr. Gordon on occasion. No big deal.”

“Yeah, I have only seen her for a short while. She seems nice.”

“I never saw you here before, but I guess I can see why you come.”

“Uh, it’s not that simple. I can explain.”

“Save it for the Doctor. You don’t have to explain it to me. We all have our issues.”

“Julia, I would really appreciate if our little meeting here was kept between you and me. I don’t want my friends knowing I see a psychologist.”

“You really have to get over it, but okay. I never saw you at the Doctors office. Feel better?”

“Yes. I do appreciate that.”

“By the way, I love that sweater.”

I wasn’t sure if she was being sarcastic, but I thanked her none the less.

My heart was still beating a mile a minute as we headed home. It was the first time I wanted to strip myself of the girl’s clothes in a violent way. I had a panicked feeling that the whole world would be soon laughing at me. My secret sessions were now not so secret. A classmate was now part of my ever changing drama. I didn’t know what to do, but I wanted to go straight home and lock myself in my room.

“Taylor, at some point you were going to have to face this.”

“Face this! My life is over.”

“Settle down. If you are planning to get into college on a TSA sponsored ride, you need to accept this.”

“I not in college yet and right now I am not ready to face the music.”

“Well I heard you two talking. Maybe she will respect your privacy.”

“She said she would keep our meeting private, but I’m not real sure I can trust her.”

“You’ll just have too. I wonder why she sees the Doctor.”

“I have never been all that close with her, but I know she is very moody. She has also missed a lot of school over the past few years and that's always been a mystery. As she admitted to me, we all have issues.”

“Well until you ran into her, How was your appointment?”

“I think it was good, but right now it is kind of a blur.”

“Hopefully soon you can ask the Doctor about a recommendation. I don’t want to push her, but any Northwestern plans are dependent on her putting in a good word.”

“I know, but right now I am having a hard time being motivated about this plan. After feeling this crummy, I am tempted to just pack my bags for the University of Illinois. It’s a good school and I could end this silliness.”

“Don’t get depressed. We are making good progress and I am still sure this strategy will help you get the most out of your education. Keep positive and after a few more sessions, I think things will start to fall into place.”

“You are probably right, but I don’t want to think about it right now.”

“Okay.”

“I am going for a long run when I get home.”