Transitioning To College 1
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By NINA ADAMS
This is the story of how far a young High School boy and his mother will go to get into a great college and earn a scholarship. It follows the journey of a bright young boy Taylor as he learns more about himself while in the pursuit of his lifelong college dream. Part 1
Chapter 1:
To some kids college is just a consideration or pipe dream. In my family it was assumed that high school graduation would be just the kicking off point for my real education. My father had been a doctor, my mother graduated with honors from Michigan and my sister was in her first year at Duke. Going to college was a given. The only questions were to which school and what I would major in.
With my sister out of the house my mother and I lived alone in our modest home in the north suburbs of Chicago. My father had passed away when I was eight, but he was around long enough to teach me the importance of school and many of life's other lessons.
I was a pretty typical teenage boy in my junior year of high school. Besides my focus on school I was a dedicated lover of soccer. I played on the high school team and followed the professional game like a compulsion. I was a trim 5’8” tall, but was in excellent physical shape from all of my running and soccer workouts. Like many of the players from my favorite Italian team, I had long flowing hair. My mother’s family had been from Italy and I think I inherited her Italian passion and her thick dark hair.
Junior year is usually the time most students plan out their college strategies and begin to narrow down their college choices. My sister went off to college in pre-law, but I was leaning towards pre-med along my father’s footsteps. Mom had also considered becoming a doctor, but my sisters unscheduled early arrival caused her to shift into nursing. She is now head of nursing at Evanston Hospital, but I always thought she had a small chip on her shoulders because she wanted to go to medical school.
My grades and ACT college test scores were very good, but not eye-popping. I would be able to get into a very good college, but getting into a top 10 type program would be extremely difficult. Our family had no special connections or unusual affiliations. We were not minorities, our income was not exceptionally high, but too high for most financial aid scholarships, and while I was a good soccer player that was not going to get me into any of the top schools.
The cost of school was going to be an important deciding factor. We lived comfortably but not extravagantly. My dad did have a small life insurance policy and my mom made a decent living, but the cost of college was mind-boggling. My sister Nina’s college was costing nearly $60,000 a year and she had plans for law school after she finished her undergraduate degree.
The cost of her education would eat away virtually all of the money mom had put away for the two of us. Unless I could go to a less expensive school or get a scholarship, we were all going to end up in deep debt. I was destined for a low-cost state school unless we could come up with some sort of miracle. I would do almost anything to get into pre-med at one of the elite prestigious schools, but even if I did, I did not want to graduate with a mountain of debt.
Even before my sister went off to Duke we used to play games at dinner trying to come up with unique ways to get a scholarship or an edge getting into college. We looked into strange hobbies, clubs, our family tree and every academic programs under the sun. We considered oddball majors that could get us into the top schools and then we might change our majors after a year or so. It was all good for a few laughs, but never helped us make any real inroads.
My entire life began to change course one Friday morning when my mother was getting a perm. She was at her monthly Lulu appointment at the salon and the discussion turned to the ridiculous cost of higher education. Lulu perked mom’s attention when she talked about how one of her client's kids had gotten a full ride to Northwestern. The child was in her second year of college and majoring in sociology. As it turned out the student had a good but not phenomenal academic record and probably only got in because she was part of a small but unique minority.
Lulu had cut the girls hair on numerous occasions and it even done so before she was a girl. The girl named Jessica was transgendered and was able to obtain a full scholarship from a foundation that supported transgender students. So long as she was still classified as transgendered, all she had to do was participate in some minor study groups in the psychology department. Northwestern supported both the program and foundation and they even granted some favoritism to her application to encourage diversity on campus. She was able to select her own major and receive some preferential treatment with the admissions department.
When my mother heard about this girl it was like a light went off in her head. She convinced Lulu to give her the phone number of the girl's mother so that she could learn more. My mother wasted little time in a introducing herself to this complete stranger. She prepped her introduction on the premise that her only boy was experiencing some gender confusion. I was grateful I had not been aware of her early inquiries or I would have killed her.
The woman was very open and told her how her son announced as an early teen that he wanted to live as a woman. She explained how her husband and her had struggled with it for nearly 2 years before they came to terms and agree to support young Jessie’s desires. As a senior in high school he began to transition. He continued school as a boy while starting a regimen of hormone replacement therapy. Many of Jesse’s friends knew about his decision and before school was out he looked much more like a girl than a boy.
It was during one of the sessions with his psychologist that Jessica learned of Northwestern’s programs and the foundation that sponsored it. He had to go in for a couple of interviews and then submit his transcripts, but they quickly got on board with his application process. Once high school was over Jessie began to live full-time as a girl. Jessica has been doing well in school, but still had not set a date for her final gender reassignment surgery. She had a few minor cosmetic procedures, but most of the changes had been from the hormones.
Over the next week or so my mother did a lot of research and she looked into the foundation and its history. During her entire fact-finding mission she never said a word to me about it. I knew she had been researching some medical and academic subjects, but I just assumed it was for the hospital or nursing program. It was almost 2 weeks later at dinner on Thursday night that the discussion came to include me.
“Taylor, what would you say if I found a way to get you into Northwestern?”
“I would smile that asked how we would pay for it?”
“No seriously, what would you say?”
“You know how much I want to go there, but we have talked about this a zillion times. It’s a long shot at best to get in there and there is no way we can afford it.”
“But what if we could?”
“I would do anything to go there. Outside of Harvard or Princeton, it is square at the top of my college WishList. It has an outstanding pre-med program and the school has everything. It's hard to imagine anywhere else I would rather be.”
“How committed are you?”
“Mom, what’s up with you? You know how committed I am to going there. I have a Northwestern wildcat cheerleader poster on my bedroom wall.”
“You know I didn’t like you putting that up.”
“Okay, okay, but why are you teasing me about this?”
“Well honey, I have learned about an obscure program they offer at Northwestern that might just keep you from going to State U.”
“Really! Count me in.”
“The plan would assist much like an affirmative action program to get you into the school and it would probably provide a complete tuition scholarship.”
“Affirmative action? Mom we looked into this. We are too classically average. We are as white as a sheet of paper and we are a smorgasbord of ethnicity. I don’t see how we would possibly qualify.”
“Well it would require you to participate in activities of a unique minority group, both before you entered the school and as long as you were enrolled there.”
“That would count?”
“Well it’s a very small group of students and it’s not quite that simple.”
“I’m still listening, but I knew it was too good to be true.”
“Honey if you keep a very open-mind, it could be your steppingstone to Northwestern and eventually medical school.”
“Mom, cut to the chase. What is the group and what do I have to do?”
“I know this may sound a little crazy on the surface, but I know it can work. I think it might even be a great experience for you.”
“Spit it out already.”
“Well the group is called the TSA.”
“TSA?”
“The Transgendered Student Alliance.”
“I don’t understand.”
“You would apply as a transgendered student.”
“Transgendered! Isn’t that like transsexual?”
“Transgendered is a broad term that applies to all types of gender issues. In reality most transgendered people don’t have sex changes. Some just have personal gender issues that make it challenging for them to fit in.”
“You want me to apply as a transgendered student? That’s crazy!”
“I suspected that would be your initial feeling. However all you would have to do is explore your gender feelings and you could write your ticket to college.”
“Mom, they are not going to give me a golden ticket for just exploring my gender feelings. Besides, I am not transgendered. It wouldn’t be right.”
“Taylor, you just need to participate in some minor ongoing programs and at least honestly admit to having some cross gender feelings.”
“Well I’m not going to lie.”
“I don’t want you to lie, but at least consider that you have some feminine feelings. It’s not going to hurt you to admit it.”
“But I don’t.”
“There’s nothing wrong with enjoying your feminine side. I even think it’s healthy for you.”
“Mom, I don’t want to pretend to be a feminine.”
“Taylor, I am not saying you are any less my boy, but I know you have a special side to you.”
But.... what are you saying?”
“Honey, even when you were little you liked to play with your sister like two girls. I remember many times you would dress up in Nina’s ballerina or princess costume. I always thought that was so adorable.”
“Mom I was just a little kid and it was usually Nina's idea.”
“Maybe, but you did it quite a lot and you were very convincing.”
“I grew out of that.”
“Well I know that it has been three years since your last Halloween dress-up, but I think your last three costumes were a witch, cowgirl and a zombie cheerleader. Am I wrong?”
“That was with friends and I didn’t have any other ideas. I also remember the cowgirl thing was your idea.”
“I think you are right, but you could have gone as a cowboy.”
“Even if I did enjoy some goofy role-playing, I am all boy now.”
“I’m not saying you are not. I just want you to open your mind to the fact that you enjoy playing the girls role.”
“That’s stretching things, but for the sake of discussion okay.”
“You are a great athlete and I am so proud of you, but you have always had a sensitive side. You care about your fashion choices more than most boys, and you even chose to get your ears pierced on your own.”
“I only asked to get one pierced. It was your idea to get both.”
“And you got both with no hesitation.”
“All those things don’t mean I want to be a girl!”
“I’m not saying that. All I am trying to say is that you can discuss honestly some gender related issues as part of your TSA college strategy. I wouldn’t want you to lie, only be open and admit that you have thought about gender role playing and have certain shared interests with girls.”
“You want me to talk with a stranger about playing dress-up?”
“The stranger would be a Doctor sworn to secrecy. As part of the application process, you need to get an endorsement from a qualified psychologist. Outside of the doctor’s recommendation, everything you say will be confidential.”
“What if the doctor doesn’t want to recommend me for the program? Then I have embarrassed myself for nothing.”
“Northwestern is not nothing. You have absolutely nothing to lose and it will almost certainly be a very cathartic experience for you. You can talk about any personal issues you like and it will be private.”
“Let’s say I am willing to try. A few dress-up tales will not likely convince a doctor that I would be of any real value to, or possibly benefit from, a transgender student program.”
I think we can and I help influence the impression you make by enhancing those attributes you possess that might stand out.”
“What attributes?”
I’m just saying that you are a beautiful boy and if you presented yourself in a way that brought out more of your natural beauty, then the doctor could appreciate your gender ambiguities.”
“I’m not completely following you.”
“I’m just saying that when you meet the doctor an even more androgynous appearance might help compensate enough to get some consideration. Just wear some gender neutral clothes, and brush out your very long hair in a way that shows how much you care for it. Don’t just wrap a rubber band in the back and look grungy .”
“You want me to pretend to be more effeminate?”
“I’m only suggesting that you bring to the surface more of what is already there. You have gorgeous hair, pierced ears, you take great care of your figure and you always like to wear stylish clothes. Those things are who you are and all I am suggesting is that we put those front and center and we use them to make a good impression.”
“It’s still seems a bit deceiving.”
“It would be for your friend Mac, but not so much for you. When you go to church you dress up nice out of respect and to make a good impression. This is the same thing. When you introduce yourself you will need to reflect the right attitude and appearance. A little extra effort would at least get you through the door.”
“As bad as I want to get into Northwestern this just sounds so drastic. If it works I will be stuck with a label.”
“You always told me that labels are for bigots and closed minded people. This is your chance to express that. Values only matter when standing up for them it is difficult.”
“True, but if I am successful I will need to be comfortable enough to follow through.”
“I suspect you will enjoy it more after the initial nervousness wears off. It’s not like you didn’t enjoy your past gender bending experiences. This will just be on a new level.”
“Let’s say I am willing, what would be necessary? You seem to have all the answers.”
“It starts with the psychologist. You would have to go to probably 4 to 6 sessions before we could ask for a recommendation. Assuming the doctor is on board, then we would submit your college application in April. The TSA at Northwestern have an interview process in late June on campus. If all goes well you would know before your senior year started.”
“How did you get all of this?”
“I will explain it all to you later, but it started with Lulu and one of her clients. It all came together from that. Without Lulu, I would never have known about this.”
“So weird. I have always liked Lulu. She's always been nice to me when she trims my hair.”
“See, you even like going to a salon to get your haircut.”
“Barbers don’t understand having long hair.”
“You don’t have to convince me.”
“Do I know Lulu’s client?”
“No, she went to Deerfield high school, but maybe someday you will meet her.”
“I guess for now you can count me in. If it gets too bizarre, then we will have to see.”
“I figured you would agree. In two weeks on Saturday you have an appointment with Dr. Ruth Gordon, and following that you will have a standing Saturday appointment with her until you get the recommendation or we decide to stop. She may want to meet you a couple of times during the week until she gets a good handle on your case.”
Wow, you have this all planned out. But Mom, let’s keep this our secret. I don’t want my friends to know I am seeing a psychologist.”
“Of course, Lulu is the only other person who knows anything about the subject. And she doesn’t know about our intentions.”
“This is a lot to take in and a very strange concept for me to absorb. May I be excused to finish up my homework?”
“Yes, you need to keep your grades up for this to be successful. For now that should be your focus. I will take care of the rest.”
CHAPTER 2:
My mother and I did not discuss our unconventional strategy again for over a week. It didn’t stop me from thinking about it quite a lot. I kept thinking about what she said about me and how I have some gender issues. I did enjoy the few experiences dressing up, but I never thought anyone really cared or paid attention. The discussion was making me second guess my own dressing up motivations and felt like a direct punch to my psyche.
A couple of days before my Saturday psychologist appointment my mother casually mention that I also had a hair appointment with Lulu. It would not have even registered, but I was not due to see her yet.
“Why so soon?”
“I want you to look nice for your appointment. We talked about this.”
“What is she going to do that I can’t do myself at home?”
“Chill out. She’s on our team. She is just going to help you present yourself in a stylish, but more androgynous way.”
“What did you tell her?”
“Questions, questions. She doesn’t know very much about your scholarship intentions, but in order to coax out all the information on the other girl, I had to at least clue her in on some of your gender issues.”
“What do you mean other girl?”
“Don’t be so sensitive.”
“There goes our secret.”
“You’ve known her for years, you can trust her. All she knows is that you are having some ambiguous feelings like her other client Jessica. I told her that after she finished up with you, that you would be going directly over to see Jessica’s doctor to sort them out. That’s all she also knows at this point. She knows you are sensitive to this getting out.”
I had a hard time focusing on my school work that evening and rapidly my anxiety level skyrocketed. I kept telling myself Northwestern was worth it.
Saturday morning arrived too quickly. When I emerged from the shower I found some new clothing on my bed.
“Mom, where did this clothes come from?”
“Taylor, I bought you some new jeans and a matching top for your appointment today.”
“I don't need anything new. I have nice jeans.”
“These are more stylish. We talked about you reflecting your fashion sense and range. At Macy's, the top was paired with the jeans on the display.”
The jeans were hard to pull up my legs. There was a small zipper at the bottom of each leg that I had to loosen to get them to slide all the way up. These were a lot like skinny jeans, but fit me more like my running tights. The pockets were virtually useless. They were so small and tight that their was no way I could keep anything in them. These may have been a new style, but they were a radical design compared to anything I owned.
The T-shirt was also unconventional. It was a very pale purple with a thick black band at the oval neckline. The neckline had a flat silver beaded pattern mixed in. It was stylish, but not remotely masculine. I knew my mother had chosen this set so that I would appear more androgynous, but I thought it looked too feminine. I tried to complain by yelling down the hall. My barking fell on deaf ears.
“Please just get dressed and let me see you.”
“These clothes are so sissy-like, mom.”
They’re fine. It’s very important that you express more of your gender neutral side. Get dressed and let me see you.”
I reluctantly pulled the top over my head and it floated down my torso. It was very soft and was much longer than any of my other tops. The shirt covered my fake pockets which I was grateful for, however, the sleeves were only three quarter length. I couldn’t imagine wearing these clothes if there wasn’t so much on the line.
I had to idea what shoes to wear with this get up so I walked down to my mothers room in my bare feet.
“You look nearly perfect. I think that should do well for a first impression. I have some cute bracelets that would look great on you, but I don’t think you should over-dress for your first appointment. I bought you some basic clogs that will look great with that combo.”
Mom handed me a pair of black patent leather Dansko clogs. They were exactly like a brown pair I already owned, but mine were just brushed leather. These were very shiny and much more eye-catching.
“You don’t even need socks.”
I flipped them over my feet to complete my ensemble.
“Mom, where do I put my wallet and keys?”
“For now you can keep them in your coat pockets, but I will need to get you something for that. I haven’t had enough time to properly expand your wardrobe.”
“I think you have done plenty.”
“Before we head out, I want you to put your nice set of gold studs in your ears. I think some of my nicer earrings would look great on you, but for today it's only important to show a hint of your flexible gender expression.”
I was grateful to wear my heavy black leather jacket over my strange outfit. I guess my coat could be classified as gender neutral, but at least it didn’t scream sissy or girl.
I was very apprehensive when I got out of the car in Lulu's parking lot. I had been seeing her for my trims and cuts all the way back to when my father had passed away. She was only 30, and I always valued her opinions because I thought she had such a great sense of style. I remember having a crush on her when I was younger. She had never given me a hard time about my long hair and always gave me good tips to care for it. I only saw her every couple of months, but I considered her a friend.
Inside her small shop I had to wait about 10 minutes before she was free for my appointment. Normally, while waiting, I would flip through the entertainment or fashion magazines, but for the first time I was stressing out and sitting almost petrified. My mother left to run some errands and I felt like I was on a pedestal. There were four women getting cuts and treatments and I kept glancing at them to see if they were staring at me.
After what seemed like forever, Lulu called me over to her styling chair. Fortunately, it was the most remote area of the salon and the least visible to the other patrons.
“Take off your coat Taylor and have a seat.”
“Hi Lulu, how have you been?”
“Just fine. Your mother tells me you have been doing great at school.”
“I guess. Just a lot going on with school plans and other things.”
“That’s what I hear. Oh, that’s a lovely tunic you are wearing. Where did you get that?”
“Tunic?”
“Your top silly.”
“I have no idea. My mom bought it for me. She also got me the jeans and shoes.”
“I love all the new tight styles. It’s amazing all of the different looks you can create with them now. You really look very cute in that tunic and tights combo.”
“I have never gone out dressed like this before. I am having a real hard time getting comfortable with it. Please don’t tease me.”
“Honey I would never tease you. I think it is great that you are being open with your feelings and finally exploring your opportunities. To be honest with you I always suspected that you might have these desires.”
“I don’t know what my mom said, but I am only dressed this way to express my flexibility. It’s not what you think.”
“I am sorry if I made you uncomfortable. I know you have an appointment after we are done. This must be very challenging for you and it is a big step. I will try and help you however I can.”
“Thank you Lulu. I know you mean well.”
“You know I always wondered what I could do with your beautiful hair. It’s so long now and there are quite a few options we could choose.”
“Lulu, all I need is my trim. Mom wants my hair to look nice so it is obvious at my appointment that I take extra special care of it. That is really all I need, besides, I have to go back to school on Monday and I don't want to look like a weirdo.”
“I understand, I am not going to cut much or make any major permanent changes. It’s mostly how I will set it. I am going to give it more volume and bounce. Tomorrow you can wash your hair and it will return to almost normal. Your mom wanted me to add some style for today and soften your look a bit.
“Nothing crazy please. Okay?”
“Of course, trust me you will look fabulous. You have great bone structure and a little magic will make just the right impression. Just relax while I wash your hair.”
Lulu gave me a very relaxing wash and scalp massage. She covered me with a purple cape and began to comb out my hair.
“You know, I could give you a gorgeous trendy new look, but I understand that might be too much for you right now. Maybe another day we can be more adventurous, but for now I am going to just even off the lengths as best I can. As your hair continues to grow even longer, the uniform length will give us the most options. You will be able to style it as little or as much as your mood dictates.”
“Okay, just trim away.”
It didn’t take very long to trim my hair. She actually clipped slightly more in the back than in the front. When she put her scissors down she started sectioning my hair and rolling in a curler.
“What are you doing?”
“I want to give you some volume and put some wave in your hair.”
“Those are hair curlers. I can’t wear these.”
“You only have to wear them long enough for your hair to dry. As I said before, you can wash your hair later and the waves will fade away. Have I ever given you a bad cut?”
“No, but this is different.”
“Calm down, this is the best way for you to explore your gender feelings in a temporary, but attractive way. Remember I am in your corner.”
“I’m just so embarrassed.”
“No need to be. No one is paying much attention and anyone who looked back here would probably just assume you were a girl.”
“That’s what makes me nervous. Let’s just get it over with.”
It took Lulu almost 15 minutes to put in nearly 20 curlers. I felt very foolish, but after the first two or three I began to relax. Lulu had never spent so much time working on my hair. With all the effort Lulu had put into my mass of hair it finally had sunk in how long I had let it grow. I didn’t know any male classmates with hair as long as mine. I started thinking about why I had let it grow so long. I liked my hair long and it never seemed anything but normal to me to let it continue to lengthen.
When she was finished with the rolling. She sprayed a setting lotion on each roller.
I just need to let that set for a couple of minutes and I will put you under a dryer. In the meantime I am just going to clean up your face a little.”
“What's wrong with my face?”
“Just some wild hair growth.”
She removed what little fuzz that could be considered sideburns. I really didn’t have any facial hair at this point and she made certain I was smooth as a baby. She began plucking my eyebrows before I started to complain.
“I am just evening them out and giving them just a hint of shape. I have plucked some of these before and you never complained.”
“Okay, but not too many.”
She clearly plucked more that she had in the past.
“No one will notice anything other then how much better they frame your beautiful eyes. They are still bushy and all I did was move the peak over just a small fraction. It’s time to dry your hair.”
I wasn’t sure how long I was under the dryer, but I was happy to return to Lulu’s more private remote cubicle.
“I don’t want you to see yourself until I get all of the rollers out, so I’m going to turn your chair around.”
After removing the rollers she took a long wire tooth comb and brushed out each section. I could see the smile on her face growing with each stroke of the comb.
“You know a little makeup would be the perfect finishing touch.”
“No way.”
“Alright then, are you ready to see the new Taylor?”
“As much as I will ever be.”
“She removed the cape and turned the chair around.”
“My heart skipped a beat. It didn’t look like me. I looked like a cute girl. I was both attracted and startled by my image. This was not even close to androgynous. This was a girl style. It may not have been cut dramatically, but the waves of curly hair had beautifully feminized my face. I was certainly going to scream a boy with major gender issues when I saw the Doctor.”
“I look like a girl!”
“Yes you do. Don’t you love it?”
“I can’t go out like this. People will look at me funny.”
“They might look at you, but not in a funny way.”
“They will see through my hairstyle and know I am a boy.”
“Hardly, but just a touch of makeup and it would be impossible.”
“This is already too much.”
“A couple of strokes and no one would ever suspect a thing.”
”Fine, as long as I can wash it off when I get home.”
Lulu turned the chair around again. She worked on my eyes for a few minutes. Next she put some powder on my cheeks followed by some pinkish red lip gloss. I started to resist the last step, but she insisted it was the last thing.
I still had not seen the finished look when my mother walked over to the chair.
“Oh my goodness. Taylor you look stunning. I can’t believe how glamorous you look.”
Lulu turned the chair so I could see the full effect. I could have been a model on a magazine cover. What little boyish elements my face possessed were completely masked by Lulu's handiwork. I was at a loss for words. It didn’t stop Lulu and my mother from discussing my successful transformation.
“Lulu, this is more complete than I anticipated, but Taylor looks ravishing. He even resembles his sister. I would have been happy with just a fraction of this, but I am sure Taylor will make a bold impression with the therapist. I feel strange calling Taylor a ‘he’ right now.”
“You know Rachel, I would have to completely agree with you on that. At least while he is glowing so beautifully.”
“I'm sorry, but we need to run now. Taylor’s appointment is in only 10 minutes and I don’t want to be late. Thank you. I will settle up with you when I come in next Friday.”
Moments later I was being whisked out the door and off to the car. My mother couldn’t take her eyes off me.
“Taylor, I am sorry that this seems to have gotten a little out of hand. I told Lulu we were going to Jessica’s gender therapist and that you wanted to reflect on the inside and outside some of the same feelings that Jessie had expressed. I didn’t ask her to do a total makeover. I certainly didn’t say anything about makeup.”
“The makeup just happened. When I saw my hair, I sort of freaked out. I was afraid that I looked so girlish and I didn’t want anyone to suspect I was a boy. Lulu suggested a little make up to insure that no one would notice me and I went along. I didn’t realize it would be this dramatic.”
Taylor you look lovely. Other than a flat chest you look like you walked out of a 17 magazine. I’m sure you are as pretty as any other girl at your school.”
“Mom, there goes that ‘other girl’ thing again. I may look like one, but I am your son. I feel like I am dressed for Halloween again.”
“Well you always enjoy dressing then, so you must be enjoying it now.”
“Enjoy is not the first words that came to mind. I think stunned would be more appropriate.”
“Okay, but how do you feel about looking so beautiful?”
“I like that I turned out attractive, but I am extremely conflicted about that.”
“Well that’s part of the point. Just remember to tell the doctor that you like looking pretty. If the doctor accepts that as your honest feelings, I am sure we are on our way to getting his recommendation.”
“I just didn’t think I would be taking this so far.”
“It’s worth it and besides I know deep down that at least part of you is enjoying this.”
“Whatever. I just hope I don’t run into anyone I know.”
The appointment was less difficult than I anticipated, Dr. Gordon was very friendly and not at all judgmental. She managed to complement my appearance without me getting defensive or uncomfortable. Very little of the actual discussion turned out to be about my gender issues. She just wanted to know more about me and my family. We talked about things I’ve never spoken to anyone about. I was there for almost an hour and a half, but was surprised when our time was up. We scheduled a follow-up session for Wednesday after school. She felt that it would be better than waiting until our next standing appointment Saturday.
Transitioning To College 2
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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.
--My First Bra--
“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.”
Transitioning To College 3
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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….
Transitioning To College 4
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unusual strategy to get into Northwestern University, the pretending becomes so much more. Saturday night, as a guest at a wedding, Transitioning to College
Part 4
Copyright © 2013 Nina Adams
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Image Credits: Divider licensed for use in publishing from Photoshopgraphics.com ~Sephrena.
Chapter 12
It felt almost foreign to get ready for school Monday morning. I wore baggy jeans and a Nirvana long-sleeve jersey. I made sure there was no leftover makeup on my face and I removed the polish on my fingernails. I pulled my curly hair back and double banded it in the back. It still looked wavy, but not enough so to raise eyebrows. The hair in the back behind the ponytail was much fuller and so I added an extra rubber-band a little behind the first pair to reduce the volume. The only feminine articles adorning my body was the remaining toe polish and the pair of panties that I had underneath my jeans. I could have worn boy shorts, but I was getting to like the feel of the panties.
By the end of the weekend I had gained enough confidence in my in my appearance and performance to strut around without worrying about being singled out. However returning to my male world was much harder. I was walking to my classes scared stiff that my appearance or body movements were going to raise red flags. I had to catch myself on more than a few occasions from responding or sashaying around like a girl. It was more difficult than I expected to return to my boyish ways. I was concerned that I might be sending out subconscious signals.
Monday's school day seemed like 12 hours. I was so happy when the final bell rang and I was able to head out. I went straight home and stripped off my boy clothes and quickly changed to casual girl mode complete with some light makeup. I knew that was part of the plan, but it just seemed to relive my stress from the long day. Tuesday was much like Monday, but on Tuesday I chose to wear a skirt with a spring style tunic after school. I played with my hair a while and created a partially pulled back style like I saw on one of the girls at school. I borrowed a pair of long teardrop earrings from my mother to complete the look.
---I actually found it kind of fun to play around with my hair---
|
My world took a strange twist at school on Wednesday. A girl that I always liked, but never really had an opportunity to get to know, cornered me near my locker. Emily stopped me and asked if I had a minute.
"Taylor, I have known you for a long time and it's crazy that we haven't ever gotten together. I know there have been whispers about you, and I am cool no matter what. I was just wondering if you might want to go with me Saturday night to a party. Claire Ashford is having a party at their massive lakefront house. I think there is even going to be a band." "A band at her house, wow." "Claire’s is calling it a birthday party. It is her 17th Birthday and she was in California for her sweet 16th." "That sounds pretty spectacular." "Yah, I was wondering if you might like to go with me there.." "Would I, that sounds great." "Does eight work for you?" "I can't believe I am saying this, but I can't go with you." "Already have a date?" |
"Uh, it's not really that. I have a wedding I promised to go to."
"Someone in your family getting married?"
"It is more like a friend of the family and I promised to attend."
"Your loss."
"Maybe we could do something else."
"You never know. I hope you have fun at the wedding. I have to run to class now. Bye..."
I felt so dejected as she walked away. Any other time I would have jumped at going out with her, but instead I was going out as the date of a guy. It was a bizarre turn of events that was becoming almost the norm for my recent life. For a brief moment I had felt my testosterone re-emerge in my veins, before it all drained out. As soon as my Saturday night plans returned to my forethought, I realized how far I had fallen out of my male world.
I was still moping when I caught the bus home from school. I went directly up to my room when I got home, but decided to wait a while before changing. It was almost like I thought remaining a guy for an extra hour or so would prove something to myself. What little I knew about Emily I liked. I even picked up a couple of fashion tips from observing her. It just didn't seem fair and the twist of circumstances was almost impossible to imagine. I really had not had that many dates and my next one would be with a guy.
I was still in boy mode when my mother got home. She was surprised to see me doing my homework still dressed like I had been in the morning.
"Taylor, Why are you still dressed that way?"
"What way?"
"You are still in your male clothes. You know what I mean."
"It's because I am a guy."
"Yes honey, but you are supposed to be dressing as a girl when you get home."
"Mom, this is crazy. I am a guy and this scheme is ridiculous. Playing dress-up like a kid to get into college is for the birds. I can't believe I let you talk me into this."
"What's really going on? You were doing great. We are almost there."
"Where? The funny farm!"
"Tell me what happened at school today. This is not you talking."
"How am I supposed to have a life if I am dressed up like a girl most of the time?"
"Well honey, we had fun last weekend and you should have fun again this coming weekend."
"Fun! I am going to be some guy's trophy date. I should be the guy taking out a girl, not the other way around."
"Is that what this is about. Did you have a problem with someone at school today?"
"My problem is that this transgender crash course is creating chaos with my social life."
"Are you missing your friends?"
"It's more than that."
"I'm listening."
I proceeded to tell my mom about the girl at school. If it wasn't for temporarily putting all my effort into the college program, I would have jumped on the chance to go out with Emily.
"As soon as you get the recommendation you will have plenty of time to date whoever you like. This is the home stretch. Maybe you can call her and get together with her some other time."
"It sounded like a cool party."
"Give her a call later, maybe you can do something else with her. For a the time being your focus has to be on the program. If you don't put your best effort in, this could take longer to get the Doctor on board."
"I know. I am just a little down right now."
"It will be worth it."
"Assuming I get in."
"Be positive. Besides, I know this has not been all bad. This past weekend you were glowing. The girl with me at Northwestern was a happy and well balanced young woman. This all may seem unusual, but that was not a boy walking around in a Halloween costume."
"That was fun, but it is getting harder to draw the lines between my two worlds."
"You will figure it out soon enough."
"Or go crazy trying."
"Go get yourself dressed and we will have some dinner. I have a small surprise for you after dinner."
"For some reason, that scares me. I think I can wait."
Later after we shared a salmon fish fillet for dinner my mother went back out to her car to retrieve the so-called surprise. My suspicions were not far off base. The gift was in a garment bag with the words NeimenMarcus on the side.
"I bought two dresses at NeimenMarcus for you to choose between. I know that your sister Nina has some lovely Prom dresses, but this is your first formal event and I thought you should have your own beautiful dress."
"I should be buying a suit or tux for my first formal event."
"Let's not start that again."
"Okay, let me see."
Inside were two designer short dresses. The first was a blue sleeveless Jacquard cocktail dress by Nicole Miller. The second was a floral sheath dress by Lela Rose. Both looked gorgeous just dangling from their hangers. We had not even shopped at NeimenMarcus together, so I had not seen them before.
“Mom, these are beautiful, but I don’t need anything that nice for this one occasion.”
“Honey, I remember buying Nina’s first formal dress and you deserve something special too.”
“Thank you, even if it is illogical. How did you even know what size to get?”
“You tried on enough dresses at Bebe and the other shops for me to get a good idea.”
“I still can’t believe I am going to wear one of these to a wedding.”
“The bride will probably be jealous. Now let’s see you in them. You only get to keep one.”
The dresses were the ultimate in femininity. As much as I wanted to temper my excitement, I couldn’t resist trying them on. Both caressed my body and pulled me back deep into my desire to look pretty. The two dresses looked very different on me, but we liked them both. The Nicole Miller dress had a more sophisticated cocktail party look and the Lela Rose dress was more youthful and festive.
I tried them on with a pair of Nina’s off-white strapped pumps. I became infatuated with my own image in the full-length mirror. I was attracted to my appearance, but there was something more to it. I was fascinated by how each dress brought out the most in my natural femininity. It was so hard to decide on which one to keep. I asked my mother to choose, but she wanted me to make the choice.
“I want you to select how you want to look. Each dress is a kind of statement and reflection of your current personality.”
“Don’t make it even harder to pick.”
“Take your time.”
“I think I am going to go with the floral one. I love them both, but the sheath dress looks more appropriate for a wedding and makes me look more innocent. The blue dress is beautiful, I think it would look nicer for more of a New Years Eve cocktail party. It’s a tough choice, but I think the Lela Rose is more my style.”
“Your style... okay then, it's that dress...the decision has been made.”
“It’s so much easier to be a boy. The choices are so limited.”
“That’s part of the fun. Now take the dress off so you don’t ruin it. Your time to show it off is only a few days away.”
I hung the dress on the outside of my closet. I probably should have put it in the closet, but I enjoyed looking at it. It distracted me from focusing on my homework. I started to think about what accessories would look nice with it and what color I should put on my nails. I kept telling myself that I shouldn’t be going to the wedding, but then I would convince myself that as long as I had to go, I should look my best.
As I was preparing for bed I finally remembered that I was going to call Emily. It was now too late. I had been so distracted by my own vanity that I forgot to call the girl that only hours ago had gotten my attention.
At school Thursday, I saw Emily hanging with some guy in the cafeteria. I guess it didn't take her long to move on from my missed opportunity. I still was going to look for a chance to talk with her and make some alternative plans. With a new guy in the picture it might just have to wait. It still hurt a little, but I tried not to get upset over it.
Thursday evening my mother informed me that I had another Lulu appointment for Saturday afternoon. This was a more crowded time of day, but she wanted me to get a fresh polish change and have Lulu put my hair in a festive set. It would be a short visit and probably finish up about a half hour before Jake planned to pick me up. It would leave me just enough time to put on my party dress before he arrived.
Thursday evening after I had finished my homework I got bored and did a little web surfing. I am not sure what possessed me, but I Googled weddings. I clicked on the image search and immediately I was deluged with wedding dresses, bridesmaid dresses and all types of romantic celebrations. I was found myself transfixed on the bride and bridesmaid images.
When I was younger and had secretly tried on my sister’s bras, it had been an attempt to feel feminine and pretend to be a girl. Seeing these photos reminded me of that urge. These images were the ultimate in feminine splendor. There was nothing more female than seeing a beautiful woman in her wedding or bridesmaid dress. Here I was dressed as a girl getting turned on by the fantasy of looking even more feminine. I must have flipped through more than a hundred pages of wedding images. I started to pick up knowledge of styles for the bride and her wedding party. I abruptly quit my surfing when my mother told me I had a call.
"Who is it Mom?"
"Your boyfriend!"
"What?"
"Jake"
As if he could see me, I stood up and looked at myself in the mirror.
"Hello"
"Taylor, is that you?"
"Yes, Hi Jake."
"I just wanted to make sure you are good to go for Saturday."
"Yes, We found something I could wear, so I should be fine."
"I wouldn't care what you wore as long as you came."
"You're silly, I look forward to seeing you too."
"What are you doing now?"
"Just finished my homework and doing some girl things. Nothing you would be interested in."
"You are a girl and I am interested in you."
"You are funny. You have no idea how hard it is to be a girl. You should try it sometime."
"I'll leave that for you. I hope I am man enough for you."
"Well, I am going with you Saturday."
"That's all I needed to hear. We should have a great time."
"It's my first wedding in a long time."
"I'll have to keep you away from the bride so she doesn't get jealous."
"Now you are being crazy. Save some of your compliments for after you see me. Then maybe I will believe you."
"Okay then, see you at 5:30."
"Look forward to it, bye...."
I was still standing when I hung up the phone. I had been unable to stop myself from playfully flirting with him. I kept digging myself deeper into a hole. I was going to have to try harder to think straight when I was with him at the wedding. Playing around like this could get me in a compromising position. I had to avoid that and politely end his infatuation.
Friday flew my quickly and the big day had arrived. I had not even thought about my appointment with Dr. Gordon. She was the reason I was doing all this and yet my mind was elsewhere. In the morning I dressed in tights and a sweater dress. I wore my shiny clogs and some hoop earrings. I put on some daytime makeup and combed my wavy hair so that it looked reasonably attractive. I liked my reflection on the closet mirror because I looked natural. It looked like how I felt and not like a disguise. I didn't even feel the need to add or subtract any items for the Doctors benefit. I was just presenting a version of me.
I am pretty sure the Doctor immediately picked up on how confident I was becoming in the girl role. She commented how much more at ease I seemed.
"Did you spend a majority of your time exploring your possibilities?"
"When I was not at school I was almost always pretending to be a girl."
"Pretending is an unusual choice of words. Do you feel like you are pretending right now?"
"It's easier now. It doesn't feel so foreign."
"Do you like how you feel?"
"It's not so bad."
"You still seem reluctant to be completely honest with yourself. I think you have done great for only one week. Most people have a tougher time at the beginning of their transition."
"Yes, the transition from boy clothes to girl clothes is very challenging, but I have worked hard at this all week. My mom has been teaching me all sorts of stuff I never knew. Pretending to be a girl is a lot tougher than just wearing girls clothes."
"Especially if you keep thinking of it as pretending. Tell me about what you did this week."
I am sure the Doctor did not often get surprised, but I know she was thrown for a loop when I told her I had an engagement with a boy coming up this evening. She was fascinated that I had already been comfortable enough around a boy to find myself out on a date. I tried to not describe it as a date, but rather as a get together. She probed me extensively about my emotional feelings about dating. She was interested in not just my pending rendezvous, but also how I felt on past dates. I did not have any juicy stories to relate to her. I had gone to homecoming and a few movies with girls, but I never really had anyone I would classify as a regular girlfriend. I slipped in a mention of Emily and how I planned to call her sometime soon. She gave me a quizzical look when I mentioned that.
I did a poor job of explaining how this wedding get together materialized. I tried to convince her that I didn't really want to go, but she was skeptical of my story. She also asked me if I was nervous. She smiled when I told her that I was kind of nervous because I did not have a lot of experience dating. She told me to just be myself.
When we were done discussing my evening plans she asked if I could come back Wednesday instead of waiting until next Saturday. She was anxious to hear how the wedding went. I agreed to see her again Wednesday at 5:00.
Chapter 13
When we returned home I wished that I didn't have so much time to kill. It wasn't my desire to go out, as much as the waiting seemed to build my anxiety. A big part of me was excited to get dressed to the nines, but this was dark territory for me. I had no clue how I was going to handle that environment.
After what seemed like forever, I began my preparation. I took a long shower and shaved the almost non-existent hair on my legs. Though I was not going to wear my new dress to the salon, I selected a very feminine sleeveless dress and did a nice job of applying makeup to my face and brushing out my long hair. I was going to get the full treatment, but I wanted to show up looking the part.
At the salon I received double barrel attention. While Lulu worked her magic on my hair, I had my nails done. My hands glistened a rosy pink shine. My hair was put into a formal and equally sexy cascading style. Both side were partially pulled up towards my crown with clips and the hair cascade down on the backsides and in the rear, I had just a few strands cascading down in the front. My makeup was replaced with a sophisticated evening look. My eyelashes were made extra long and thick to stand out from the heavy dose of blended eye shadow. My cheeks were aglow with blush and my lips perfectly matched my nail polish. With every stroke of makeup, I was made to look more desirable. Even in the less formal dress I was wearing now, I would have looked appropriate at the wedding.
When I sashayed out of the salon I had an extra bounce in my step. As much as I knew I had to keep my transformation hush hush, I was dying to go for a walk and put my new glamour on display. I couldn't believe how much I was enjoying my new image. It was probably good that I was under a tight schedule and needed to go home and make final preparations for the wedding.
My mother helped me get changed and she picked out some matching jewelry. The diamond earrings she inserted in my ears were the ones she wore at her wedding. They were a family heirloom and had a classic emerald cut. They probably were worth more than most women’s engagement rings. I had seen her wear them only a couple of times and I knew how much they meant to her.
"Taylor, I only take these out of the box for special occasions. This is a big night for you. My little girl is growing up."
I thought about rebutting her comment, but I knew she was trying to make this experience special for me so I smiled and gave her a hug. I could see what looked like a small tear in the corner of her eye.
"Mom thanks for helping me get ready."
"You look perfect. Are you ready?"
"On the outside I know I am ready. It's the inside that I am not so sure about. I feel wonderful right now, but the date thing scares me. What if he wants to touch me or something?"
"Honey, he's a boy, so of course he is going to want to touch you. You will probably have to dance with him. Just relax and let it come to you. If you get uncomfortable just remember the word...NO. He comes from good stock, so I am sure he won't be aggressive."
"God, I can't believe I am going out with a boy."
"I think I just heard him pull up. Go to your room. I want him to come in so I can see the expression on his face when he sees you."
"Really?"
"Go go... please do that for me."
I heard Jake enter the front door, but could not make out the conversation he had with my mother. A couple of minutes later she called for me to come. My heart was racing as I made one last check of my appearance. I painted a big smile on my face and worked my way down the hall.
Jake was looking at his shoes as I entered the room. As he began to look up I could see his expression turn to joy. I cocked my head slightly and said, "Do I look okay?"
"You are beautiful, no make that gorgeous, all I can think of is that you look amazing."
"Thank you, you look pretty good yourself."
"Right now I feel like the luckiest guy in the world."
"Stop, see if you still feel that way later."
"I know I will. I am so glad you were able to go with me."
"Just don't let me embarrass myself."
"I'll do my best.... Mrs. Dawson, it might be a little late, but I will bring your lovely daughter straight home from the wedding."
"Thank you Jake. Would you mind if I took a couple of pictures of you two together?"
I gave my mother a pursed look, but I stood next to Jake for about 4 or 5 photos.
"Mrs. Dawson, if it would not be too much trouble could you email a couple of them to me. I will write down my email."
"No problem Jake. Make sure you show them to your father. I would be curious what he thought."
"Gladly, he has been looking for an excuse to call you."
"I am only so happy to help him."
"Mom! We need to be on our way."
"Taylor dear, wrap this around yourself so you don't get too cold."
As we were prepared to leave the house Jake reached out for my hand in a very polite social gesture. I instinctively grabbed his hand as he walked me to the car. It was the first time anyone had ever walked me to a car door and opened it for me. This gentleman was treating me as his prize. Everything about this evening was a first and at this moment it did feel special.
In the car Jake filled me in on some of the people I would be meeting. Since this was the other side of his divorced parents, I would be meeting his mother. I had not thought about that, but I knew she would be giving me a very close once-over. If anyone would be able to see through my feminine appearance it would certainly be her. I was confident, but did squirm a little when he mentioned this.
I had practiced walking on heels, but I still felt a little awkward as we walked from the car into the Four Season's Hotel. This was a very luxurious place, which was obvious immediately upon entering the lobby. Jake once again held my hand tightly, which was a continual reminder that we were a pair. At the guest table we received our table assignment and we were placed at a table with 4 other young couples. I was grateful that we were not sitting with his mother. The schedule called for the wedding, followed by a cocktail hour and then dinner and dancing.
Inside the reception area many cousins quickly greeted Jake. They were very interested to see whom he had brought. I was thrust into the center of everyone's attention. I met so many people and couldn't keep up with all of their names. Everyone wanted to know how long we had been dating and how we met. It was uncomfortable to explain that we hardly knew each other. Jake just chimed in that despite our short courtship, he immediately knew there was something special about me.
I played along, as it seemed the path of least resistance. I gave him a giant smile and he returned my enthusiasm with a soft peck on the cheek. It was very innocent, but I could feel my blood rushing as the grip of our hands firmed. I also felt a slight stir between my legs.
After a few minutes of group conversation Jakes first-cousin Jana started to engage me directly. She was anxious to learn more about me and to find out if we had any mutual friends. She was very big into dance and theater and rattled off three names I knew from school. None were real friends, but it scared me that she knew people that might know me. She was very friendly, but her social geography was way out of my league.
"Jake is a really nice guy, but I was still surprised to see him show up with someone like you."
"Like me?"
“His last couple of girlfriends were real bitches.... I have no idea what he saw in them. You seem almost too nice. You are friendly and way cuter than his past girlfriends.”
“Jake seems nice too, but we really haven’t been going out. I only met him recently.”
“That may be, but he sure is smitten by you. I know that look in a guys eyes.”
“Thanks for the warning. By the way, I really love your dress.”
“I am the Maid of Honor. Too bad Jake didn’t meet you sooner, maybe you could have been a bridesmaid.”
“That’s kind of funny, but thanks.”
“What’s so funny?”
“Nothing really, I’m just nervous being here as a guest.”
“Don’t be. Have you met Jake’s mom yet?
“Not yet.”
“I am sure you will hit it off. Just don’t mention his Dad. That is still a sore point.”
“Thanks again for the advice.”
“I like you, I hope we can chat more later. I have to run now to get ready for the precession.”
“Bye for now. I should get back to Jake anyway.”
Jake was only about 10 feet away during the conversation with his cousin, but in the crowded room it seemed further. When I made my way back he put his arm around my shoulder and pulled me in closer. As Jana had indicated, there was no doubt how Jake was thinking about me. I liked the attention, but I knew it was a path I had to avoid.
"Taylor, you are being a good sport and everyone already seems to like you. Lets go find a seat for the ceremony."
"That's a good idea. I'm not used to wearing heels and sitting would feel good right now."
We sat near the front and before we could get settled in, Jake's Mother sat next to him.
"Well Jake, I think I am the only person who has not met your girlfriend."
"Sorry mom, we weren't avoiding you. This is Taylor."
"Hello Mrs. Franklin, I am very happy to meet you. It is so nice to be here with you and your family for such a joyous occasion."
"Weddings are always wonderful times." With a friendly smile she added, "My Jake is only 18, so the two of you should not get any strange ideas."
"Mom! Taylor is pretty enough to be a bride, but we are just getting to know each other. Please don't tease us."
"Sorry Taylor, but all week Jake has been talking about you. You certainly made an impression on him. So far you have made a nice one on me too. I am glad you could join us."
"Thank you. Everything tonight is like a new experience for me in so many ways. I don't know anyone other than Jake here, but everyone has treated me like family."
“I hope you enjoy the rest of the evening and I get to see you around.”
It had been a few years since I had attended a wedding and my memories of it were not that vivid. I did recall the bride with her long flowing gown, but not much else. This time I was already taking in the beautiful details of the room and all of the attendees. The men were all dressed in dark suits or tuxes and the woman were all dressed exquisitely. My dress fit in beautifully, but I was still somewhat intoxicated by seeing all of the other formal dresses and gowns. The women were all so lovely, but I was thinking more about how I measured up, than how hot they looked. I even had a momentary tinge of jealousy when I saw one particularly pretty woman catch a glance from Jake. I could understand why he might notice her, but for a millisecond I was upset. He did not linger on her distraction and quickly turned his attention back to me.
The wedding affected me more than I anticipated. I was moved from the moment the precession began. When the Bridesmaids and Maid of Honor came down the white runway, I actually did wish I were one of them. They wore matching red satin gowns that accentuated all of their natural girlish curves. I couldn’t take my eyes off the Bride as she slowly moved past us. She looked angelic and her dress was stunning in both detail and style. She was the star of the show and she looked the part. All eyes were transfixed on her, including the groom’s. I took a couple of extra deep breaths to relieve some of the emotion that had overcome me and to regain my grip.
When they were pronounced man and wife. I almost squealed. My enthusiastic smile came naturally and I was one of the last to stop applauding. All of the new stimulations were giving me an overload of hormones and I had very little experience managing them. I had held Jake’s hand during the ceremony and he commented to me later that his hand was sore from how firmly I had squeezed it as the Bride moved by.
We had about a 10-minute break before we had to make our way into the Ballroom for dinner. We just stayed in the chapel area and let the other guests work their way into the Ballroom. It was the first time I had been alone with Jake since we gave his car to the valet.
“So Taylor, are you glad you came this evening?”
“The wedding was magnificent. I was mesmerized my the ceremony. They looked so in love.”
“It was very beautiful, but then so are you.”
I was still feeling the rush from watching the pageantry, but I could still feel myself blush at his direct compliment.
“It’s hard not to be moved by seeing the love and romance on display. Jake, did it move you too?”
“It was inspiring.”
“How so?”
Jake then looked deep into my eyes and put his left hand behind my neck. In what felt like slow motion he tilted his head and softly pulled us together until our lips met. After a quick touching of the lips he looked again into my eyes to make certain I was ok. I was motionless as he moved back in for a much longer and passionate embrace. When he broke off from that kiss I could still taste him on my lips. I was not upset, but I could feel my body pulsating and at the same time experience an unusual numbness. I had kissed a couple of girls before, but this felt different. I was never overcome by the feeling before and this came very unexpectedly.
“Taylor, when I saw the bride and groom kiss, I could only think about doing the same thing with you. I hoped you felt the same way."
"Jake, you caught me by surprise."
"Was it a good surprise?"
"I am still trying to figure that out. I have never kissed anyone like that before."
"That's sounds like a good thing."
"It was nice, but you don't know anything about me. If you really knew me, I doubt you would feel the same about me."
"I can't imagine there is anything evil or bad that would make me feel otherwise. As long as you feel the same, that is all I care."
"It is not that simple."
Instead of responding with words, Jake stood me up, pulled me in, and then kissed me as passionately as we had just observed in the wedding ceremony. I found myself responding and not just complying. I was kissing back and moved my hands behind his back. There was no mistaking my affirmative response.
"It seems pretty simple to me."
"Jake, I shouldn't be doing this."
"You are confusing me, but I can handle whatever is bothering you. I know we both want this, so don't worry."
"It's complicated and that's all I can say now. I really like you, but let's slow down."
"I am in no rush as long as we eventually are together. There is something different about you that is just driving me crazy. You are such a special girl and I don't want to blow it."
"Let's go join everyone else at the tables."
"Whatever you want Taylor."
Sitting at the table, the gravity of my situation began to sink in. I had kissed Jake and almost as importantly, I had liked it. I was no longer just living out my adolescent cross-dressing fantasy. It was also not a gay thing; rather, I truly felt like a girl and was attracted to a boy. I was so alive when Jake kissed me, but I knew we were ultimately doomed. My emotional high was now crashing and the adrenaline was now fading. I was now quickly becoming much more subdued and considerably less outgoing. I became stunted in my conversation and let Jake do most of the talking for us. I periodically looked into his eyes and smiled, but I tried not to get too emotional with him. I was fighting my internal desire to be Jake's girl.
When the meal and the speeches ended the Bride and Groom moved to center-stage for their fist official dance. Shortly after that many of the other guests made their way onto the dance floor.
In an attempt to be both formal and cute, Jake reached for my hand, then asked "May I have this dance with my Cinderella?"
I thought his question was sort of humorous, because I did feel a lot like Cinderella. I was dressed for the ball, unlike I had ever been before and I would soon be transforming back to my former secretive existence. I could not turn down his request even though it would take me further into his lair. I wanted him to hold me, but I was digging myself into an even deeper hole.
Our first dance was an old fashion waltz. Our bodies were intertwined as one, while we glided across the dance floor drinking in the music. My hand wrapped around his waist and I was certain he could feel my heart pounding. As hard as I resisted, I so wanted to feel his body against mine and feel the caress of his lips once again. I had lost any straggling ounce of my manhood and was caught up in our romantic embrace. The entire evening was like a giant epiphany. I had written a new chapter in my life that would never be able to be unwritten. My old gender paradigm would forever be altered.
With each beat of the music, I further lost my inhibitions. When we finally sat down, I thanked Jake and reached over and gave him a kiss across the lips. Jake's cousin Jana, which I had spoken with earlier, commented about my gesture "get a room."
I had never felt so romantic about anyone like this...boy or girl. I never wanted the feeling to go away, but the evening was coming close to the end. After tonight, I would be forever changed, even though this path was rapidly approaching a dangerous cliff. I wanted everything tonight to be real and at least for now, I wished I were truly a woman.
As we made our way to the valet, we walked with our arms around each others waist. Inside the car Jake began to express how wonderful it was spending the evening with me. He added that I was so beautiful and I made him feel so lucky. I was obviously not the only one that had experienced an amazing evening. We both felt the passion and romance, but my deception was impossible for me to completely erase from my mind. I wanted Jake as much as he wanted me, but we were destined for disaster.
"Taylor, I can't wait to see you again. I wish we went to the same school so I could see you everyday. We don't live that far apart, but I have never dated anyone from a different school."
"I haven't either Jake and I am not sure if we can do this."
"Do what? You do feel like I do, don't you?"
"Well yes, but as I said before it's complicated."
"Whatever is the problem, we can work it out together."
"Jake, let's just remember tonight and maybe we can go from there."
"As long as you promise for us to go from there...."
The drive home was quick and the conversation was minimal. We listened to some Demi Lavato and Jason Mraz music as I contemplated my situation. Every time I was close to saying something I lost the strength to spit it out. I never felt so appreciated or special as I did that evening, but I hated the truth that I wished was not so.
When we pulled into my driveway I felt like a different person than the naive teen that had left the safety of home only a few hour earlier. My path was no longer being driven by my college plans, but rather my heart. I may have been the last person to realize it, but the person that Jake desired was not in a disguise. This was the person I truly was meant to be.
The evening was coming to a close as Jake walked me to the door. We held both of our hands together as we stood under the dim night light on the front porch; before I slid through the door we shared one last slow lingering kiss. There was no mistaking the passion that we both felt as we gradually broke the seal of our lips. I wished him a good night and disappeared into the house. I stood almost frozen inside the door contemplating the circumstances. I could feel my lungs breathing.
"Welcome home Taylor. I don't think I need to ask if you had a good time."
"Mom, you scared me."
"Sorry Honey, I just wanted to wait up until you got home."
"Mom, I am so confused!"
"I know Honey. It must be challenging to experience all of these new emotions so quickly after discovering yourself. It's Okay to be confused."
I immediately embraced my Mom. It wasn't what she said, but I needed the comfort of her arms to stabilize my rush of emotions. Almost as quickly as our bodies met I began a flow of tears from my tired eyes.
"What's happening to me? I really want to be a girl... I'm so screwed up!"
"Nonsense... There is nothing wrong with you. If that's what you truly want, it's Okay."
"But Mom, I am a boy."
"Honey, if a girl is what you were meant to be, than you will just have to blossom into a girl."
"I should never have dressed up like this."
"Taylor, I always suspected that deep down inside you that this girl was screaming to emerge. This College program was just the right recipe for you to figure out if I was right."
"How did you know I felt so strongly about this? Even I didn't."
"I couldn't be sure, but I knew about your little hobbies and I always saw little clues. I thought letting you experience a little of this for alternate reasons would give you a chance to determine your fate on your own. With each passing day along this path I became more certain that you wanted this."
"I don't know what this all means or what to do."
"We will work it out as a family and your sister and I will support you all the way."
"I kissed a boy."
"I saw"
"And I liked it!"
We both began to smile after my last comment.
"Why don't you run off and get yourself ready for bed. Make sure you remove all of your makeup and moisturize. We will discuss this all tomorrow after some sleep and a chance to process it all."
"I think I am sleeping now... This is all like such a strange dream.... Tomorrow we have a lot to talk about...Good night Mom."
"Good night young lady."
Chapter 14:
Much like Cinderella, my life was forever altered. I had to return to being a boy, but the old life would never return to the same. The transition to college could not happen fast enough. Applying to the TSA program started as a strategy, but now was now something that would provide an important and lasting personal benefit.
The weeks and months ahead saw more changes to both my psychological and physical persona. Each day less and less of the masculine traits could be visible to schoolmates or in the mirror. I still attended school as boy, but by early summer after my junior year I began a program of HRT. The plan was that after graduation I would begin life full time as a girl that I now was certain that I was destined to be.
Initially, the chemical focus was to mostly retard testosterone production, but by early fall the hormones supplements were dramatically increased. The physical changes were quickly catching up to the now dominant psychological ones. Technically, I was still enrolled in High School as a boy, but pretty much everyone knew about the transition. To those who did not know me, I was pretty certain I "read' girl. The school even made a few special adjustments to acknowledge that I was not like other boys.
Most of my closer friends learned of my personal desires long before the school was brought in. The remaining spring of my junior year was life changing and not without challenges. Dr. Gordon became an important person in my life and helped me deal with many stressful and often painful emotions.
Jake had unwittingly been drawn into my story and the results were not all fairytale.
Taylor's first cousin Jana that I had met at the wedding discovered my true identity the day after the wedding. We had become friendly at the wedding, but her curiosity about me quickly uncovered the truth. She was not malicious, but Jake learned about my birth gender before I even had a chance to follow up on our romantic evening.
I spoke with Jake the next evening, but we were both at a loss for words. He treated me with respect, but the chill between us was the complete opposite of what we both experienced only a few hours earlier. My life had been riding a treacherous roller coaster and my first love was an unfortunate casualty. I had learned a lot about myself in such a short time, but reality had begun to expose some of the issues and potential heartache that would greet me along the road ahead.
Jake and I spoke again a few days later, but the romance never returned. It was probably a good thing that he went to a different school and we were able to avoid potential awkward interactions. Jake kept our evening between us and I was able to return to my life and slowly work through a longer-term strategy.
As I write these final words, I should add that I have gotten into Northwestern. A new chapter in my life is almost ready to begin. I am hopeful that some day I will become a Doctor and also find the romance that was kindled that special day...